DESC:
FORM 2
THE PATENTS ACT, 1970
(39 of 1970)
&
The Patent Rules, 2003
COMPLETE SPECIFICATION
[See Section 10 and Rule 13]

1. TITLE OF THE INVENTION

“MESOIONIC HETEROCYCLIC COMPOUNDS”

2. APPLICANTS

(a) PI INDUSTRIES LTD
(b) an Indian company,
(c) of Udaisagar Road, Udaipur- 313001, Rajasthan, INDIA,

3. PREAMBLE TO THE DESCRIPTION

The following specification particularly describes the invention and the manner in which it is
to be performed.

FIELD OF THE INVENTION:
The present disclosure relates to novel mesoionic compounds of formula (Ia) or (Ib) and their salts, metal complexes, N-oxides, enantiomers, stereoisomers or polymorphs thereof; compositions and methods of use for controlling or preventing pests.

BACKGROUND OF THE INVENTION:
The control of invertebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause a significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, turf, wood products and public health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic and environmentally safer or have different sites of action.

The control of animal parasites in animal health is essential, especially in the areas of food production and companion animals. Existing methods of treatment and parasite control are being compromised due to growing resistance to many current commercial parasiticides. The discovery of more effective ways to control animal parasites is therefore imperative.

Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.

WO2009/099929, WO2011/017334, WO2011/017347, WO2011/017342, WO2011/017351, WO2012/092115 and WO2012/106495 disclose pesticides having a mesoionic pyrimidine structure. However, the known compounds are not completely satisfactory in many cases, in terms, for example, of application rate, spectrum of activity, duration of activity, tendency to form resistance or economic aspects of the preparation process.

It is therefore a continuing objective to provide further pesticidal mesoionic compounds which, at least in some aspects, offer advantages over the known compounds. Surprisingly, it is now found that the novel mesoionic compounds and its compositions thereof have the potential of overcoming prior art drawbacks and are suitable for protection against animal pests.

SUMMARY OF THE INVENTION:
The present invention relates to mesoionic compounds of formula (Ia)

or salts, metal complexes, N-oxides, isomers, or polymorphs thereof,
wherein Q1, Q2, G, W, A and Y have the meaning as defined in the following description and claims.

The present invention also relates to mesoionic compounds of formula (Ib)

or salts, metal complexes, N-oxides, isomers, or polymorphs thereof,
wherein Q1, Q2, G, W, A and Y have the meaning as defined in the following description and claims.

The present disclosure will now be described in detail in the following description.

The invention also relates to the use of mesoionic compounds and its salts composition for combating animal pests. Furthermore the invention relates to methods of applying such compounds.

DETAILED DESCRIPTION OF THE INVENTION:

DEFINITIONS:
The following definitions provided herein for the terminologies used in the present disclosure are for illustrative purposes only and in no manner limit the scope of the invention, disclosed in the present disclosure.

As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests. The term “arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term “nematode” refers to a living organism of the Phylum Nematoda. The term “helminthes” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala and tapeworms (Cestoda).

In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.

The term “agronomic” refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms “parasiticidal” and “parasiticidally” refers to observable effects on an invertebrate parasite pest to protect an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.

Compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.

The term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono-or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.

The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C1 to C24 alkenes, preferably C1 to C15 alkenes, more preferably C1 to C10 alkenes, most preferably C1 to C6 alkenes. Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l,-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl and the different isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.

Representative examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.

The term “cycloalkyl” means alkyl closed to form a ring. Representative examples include but are not limited to cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.

The term “cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Representative examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.

The term “cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Representative examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.

The terms “cycloalkoxy”, “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.

The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
The terms “haloalkenyl”, “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.

The term “haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.

The term “haloalkylthio” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and l,l,l-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere. Examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.

The term “hydroxy” means –OH, Amino means –NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(O)-, carbonyloxy means -OC(=O)-, sulfinyl means SO, sulfonyl means S(O)2.

The term “alkoxy” used either alone or in compound words included C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.

The term “alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.

The term “alkoxyalkoxy” denotes alkoxy substitution on alkoxy.

The term “alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and l-ethyl-2-methylpropylthio and the different isomers.

Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.

The term “alkylthioalkyl” denotes alkylthio substitution on alkyl. Representative examples of “alkylthioalkyl” include -CH2SCH2, -CH2SCH2CH2, -CH3CH2SCH2, -CH3CH2CH2CH2SCH2 and -CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.

The term “alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.

Examples of “alkylsulfinyl” include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1-dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. The term “arylsulfinyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.

Examples of “alkylsulfonyl” include but are not limited to methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and l-ethyl-2-methylpropylsulphonyl and the different isomers. The term “arylsulfonyl” includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.

“Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples.

The term “ring” or “ring system” as a component of formula (Ia) or formula (Ib) is carbocyclic or heterocyclic. The term “ring system” denotes two or more connected rings. The term “bicyclic ring system” denotes a ring system consisting of two rings sharing two or more common atoms.

A ring or a bicyclic ring system can be part of an extended ring system containing more than two rings wherein substituents on the ring or bicyclic ring system are taken together to form the additional rings, which may be in bicyclic relationships with other rings in the extended ring system.

The term “ring member” refers to an atom (e.g. C, O, N or S) or other moiety (e.g. C(=O), C(=S) or S(=O)n(=NR3)m forming the backbone of a ring or ring system. The term “aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n + 2) p electrons, where n is a positive integer, are associated with the ring to comply with Huckel's rule.

The term “carbocycle” includes “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (fused, bridged) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).

The term “aryl” as used herein is a group that contains any carbon-based aromatic group including, but not limited to, benzene, naphthalene, phenyl, biphenyl, anthracene, and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or comprise multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.

The term “hetero” in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.

When a radical (e.g., a 3 to 10 membered ring in the definition of R1) is optionally substituted with listed substituents with the maximum number of substituents possible, the radical may be unsubstituted or substituted with upto the maximum number of substituents possible and the attached substituents are independently selected from the substituents listed. When a substituent (e.g., R1) is a ring or ring system, it can be attached to the remainder of formula (Ia) or formula (Ib) through any available ring member, unless otherwise described.

As noted above, R1 is, inter alia, a 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members selected from carbon atoms and heteroatoms independently selected from O, S, and N, wherein carbon atom ring members are independently selected from C(=O) and C(=S) and the sulfur atom ring members are independently selected from S(=O)n(=NR3)m, each ring or ring system optionally substituted with the maximum number of substituents possible, independently selected from R1. When no heteroatom ring members are present, the ring or ring system is carbocyclic. If at least one heteroatom ring member is present, the ring or ring system is heterocyclic. The definition of S(=O)n(=NR3)m allows up to 2 sulfur ring members, which can be oxidized sulfur moieties (e.g., S(=O) or S (=O)n) or unoxidized sulfur atoms (i.e. when u and z are both zero). The nitrogen atom ring members may be oxidized as N-oxides, because compounds relating to formula (Ia) or formula (Ib) also include N-oxide derivatives. The carbon atom ring members selected from C(=O) and C(=S) are in addition to heteroatoms selected from O, S and N atoms. As the R1 substituents are optionally substituented with the maximum number of substituents possible.

The term “heteroaryl” or “Het” means 3 to 10 membered, 5 or 11-membered, or 7 to 11 membered fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, l,2,4-oxadiazol-3-yl, l,2,4-oxadiazol-5-yl, l,2,4-thiadiazol-3-yl, l,2,4-thiadiazol-5-yl, l,2,4-triazol-3-yl, l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl and l,3,4-triazol-2-yl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-l,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-l-yl, 1-imidazolyl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl.

6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl and l,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-l-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, 1-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, l-benzothiophen-4-yl, 1-benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, l,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, l,3-benzothiazol-5-yl, l,3-benzothiazol-6-yl, l,3-benzothiazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and l,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.

This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.

The term “aromatic” indicates that the Huckel rule is satisfied and the term “non-aromatic” indicates that the Huckel rule is not satisfied.

The term “heterocycle” means three to fifteen-membered, preferably three to tweleve-membered, saturated or unsaturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi-or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, l,2,4-triazolidin-3-yl, l,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-l-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-l-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl and l,2,4-hexahydrotriazin-3-yl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.

The term “trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. “Halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different.”Alkoxytrialkylsilyl” denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. “Trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen.

Examples of “alkylcarbonyl” include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of “alkoxycarbonyl” include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy -or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino -or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Examples of “alkoxyalkylcarbonyl” include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.

Examples of “alkylaminoalkylcarbonyl” include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).

The term “amide” means A-R'C=ONR''-B, wherein R' and R'' indicates substituents and A and B indicate any group.

The term “thioamide” means A-R'C=SNR''-B, wherein R' and R'' indicates substituents and A and B indicate any group.

The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix wherein i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of formula (Ia) or formula (Ib) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 the number of substituents may be selected from the integers between 0 and 4 inclusive.

When a group contains a substituent which can be hydrogen, for example R1 or R2, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being un-substituted.

The term “fragments and tautomeric forms thereof, having two double bonds inside the ring” means and includes the fragments capable of forming two double bonds inside the ring by tautomerization.

The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.

The following description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.

The numerical values mentioned in the description and the following claims though might form a critical part of the invention of the present disclosure, any deviation from such numerical values shall still fall within the scope of the present disclosure if that deviation follows the same scientific principle as that of the invention disclosed in the present disclosure.

The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects, rodents.

The term “plant” is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders’ rights.

Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Preferably, the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.

The term “plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes.

The term “locus thereof” includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.

Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

The term “applied” means adhered to a plant or plant part either physically or chemically including impregnation.

In one embodiment of present invention discloses the compound of formula (Ia)

wherein,
W is selected from O or S,
A is selected from O or S,
Y is selected from R1, -OR1, - N(R2)(R3), or -N(R2)(R3)-N(R2)(R3);
G is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, CHO, C(O)NR2R3, C(=S)NR2R3, SR2(O)n(=NR2), S(O)n(NR2R3), N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R3, NR3SO2NR2R3, C(=NR2)R3, NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, C(=NOR2)R3 C(=NNR2R3)R4, C(=NN(C(=O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(=O)(=NR2)R3, SO2NR3C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR3)R4, P(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR2)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 cycloalkylalkyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 is selected from C(R3)(R4)-, -C(R3)(R4)C(R3)(R4)-, -O-, -S(O)n, NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, or C4-C10 cycloalkynyl, wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q2 selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, OCN, SCN, CHO, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, C(O)R3R4, C(O)R2OR3, NR2R3, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, OC(O)R2, OC(O)OR3, OC(O)NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R4, NR2SO2NR4R5, Si(R3R4), C(=NR2)R3, C(=NOR2)R3, C(=NNR2R3)R4, C(=NN(C(O)R2)R3)R4, C(=NN(C(O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(O)(=NR3)R4, SO2NR2C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR2)R4, OP(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR3)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, SR2(O)n(=NR3), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl,C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl,, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1; or

Q1 and Q2 may form a 4 to 7 membered ring, taken together with the carbon and nitrogen of the imidazole ring in formula (Ia), wherein each remaining ring member is selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are independently selected from S(=O)m, wherein the ring is substituted with one or more Het;

Het is 3 to 10 membered heterocyclic ring or a 7 to 11 membered heterocyclic ring system, each ring or ring system member selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein each ring or ring system is optionally substituted with at least one substituent independently selected from R1;

W2 is selected from O or S;

wherein,
R1 is selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, SR2(O)n(=NR2), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 alkylsulfinylalkyl, C1-C8 alkylsulfonylalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R5;
or
R1 is 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, SR2(O)n(=NR2), S(O)n(NR2R3), S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R5;

R2, R3 and R4 are independently selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C3-C10 cycloalkylcycloalkyl, C3-C10 alkylcycloalkylalkyl or C3-C6 cycloalkenyl, which is optionally substituted by R1;
or
R2 and R3 are taken together with the contiguous linking nitrogen to form a 5 to 7 membered heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
or
R3 and R4 are taken together with the contiguous linking carbon atoms to form a 5 to 7 membered carbocyclic or heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
R5 is selected from halogen, cyano, nitro, SF5, SCN, amino, hydroxy, COOH, SH, C1-C6-alkyl, C2-C6-alkynyl, C1-C6-alkylamino, di-(C1-C6)-alkylamino, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyloxy, cyano-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6¬ alkylaminocarbonyl and di-(C1-C6)-alkylaminocarbonyl;
or
R5 is a 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, S(O)n, S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R1;
“m” is an integer ranging from 0 to 3;
“n” is an integer ranging from 0 to 2;
or salts, metal complexes, N-oxides, isomers, or polymorphs thereof.

In another embodiment of the present invention discloses the compound of formula (Ib)


wherein,
W is selected from O or S,
A is selected from O or S,
Y is selected from R1, -OR1, - N(R2)(R3), or -N(R2)(R3)-N(R2)(R3);
G is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, CHO, C(O)NR2R3, C(=S)NR2R3, SR2(O)n(=NR2), S(O)n(NR2R3), N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R3, NR3SO2NR2R3, C(=NR2)R3, NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, C(=NOR2)R3 C(=NNR2R3)R4, C(=NN(C(=O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(=O)(=NR2)R3, SO2NR3C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR3)R4, P(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR2)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 cycloalkylalkyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 is selected from C(R3)(R4)-, -C(R3)(R4)C(R3)(R4)-, -O-, -S(O)n, NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, or C4-C10 cycloalkynyl, wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q2 selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, OCN, SCN, CHO, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, C(O)R3R4, C(O)R2OR3, NR2R3, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, OC(O)R2, OC(O)OR3, OC(O)NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R4, NR2SO2NR4R5, Si(R3R4), C(=NR2)R3, C(=NOR2)R3, C(=NNR2R3)R4, C(=NN(C(O)R2)R3)R4, C(=NN(C(O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(O)(=NR3)R4, SO2NR2C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR2)R4, OP(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR3)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, SR2(O)n(=NR3), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl,C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl,, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 and Q2 may form a 4 to 7 membered ring, taken together with the carbon and nitrogen of the imidazole ring in formula (Ib), wherein each remaining ring member is selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are independently selected from S(=O)m, wherein the ring is substituted with one or more Het;

Het is 3 to 10 membered heterocyclic ring or a 7 to 11 membered heterocyclic ring system, each ring or ring system member selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein each ring or ring system is optionally substituted with at least one substituent independently selected from R1;

W2 is selected from O or S;

wherein,
R1 is selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, SR2(O)n(=NR2), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 alkylsulfinylalkyl, C1-C8 alkylsulfonylalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R5;
or
R1 is 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, SR2(O)n(=NR2), S(O)n(NR2R3), S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R5;

R2, R3 and R4 is independently selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C3-C10 cycloalkylcycloalkyl, C3-C10 alkylcycloalkylalkyl or C3-C6 cycloalkenyl, which is optionally substituted by R1;
or
R2 and R3 are taken together with the contiguous linking nitrogen to form a 5 to 7 membered heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
or
R3 and R4 are taken together with the contiguous linking carbon atoms to form a 5 to 7 membered carbocyclic or heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
R5 is selected from halogen, cyano, nitro, SF5, SCN, amino, hydroxy, COOH, SH, C1-C6-alkyl, C2-C6-alkynyl, C1-C6-alkylamino, di-(C1-C6)-alkylamino, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyloxy, cyano-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6¬ alkylaminocarbonyl and di-(C1-C6)-alkylaminocarbonyl;
or
R5 is a 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, S(O)n, S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R1;
“m” is an integer ranging from 0 to 3;“n” is an integer ranging from 0 to 2;
or salts, metal complexes, N-oxides, isomers, or polymorphs thereof.

In an embodiment, Q1 and Q2 taken together with the contiguous linking nitrogen and carbon atoms form a 3 to 10 membered ring or a 7 to 11 membered ring system selected from the group of compounds of formulae L-1 to L-90:

In a further embodiment, Het is selected from any one of the following ring systems F-1 to F-57:


Wherever used in a structure, # denotes the bond to join Het to ring system which is formed by joining of Q1 and Q2.

In a further embodiment of the present invention, Het is seleceted from the following ring systems F-2, F-9 or F-25:

wherein,
R1 is halogen; more preferably R1 is chloro.

Yet another embodiment of the present invention discloses the compound of formula (Ia) or formula (Ib) or salts, metal complexes, N-oxides, isomers, or polymorphs thereof, for preventing or controlling animal pests.

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.
The compounds of formula (Ia) and formula (Ib) are mesoionic inner salts. “Inner salts” also known in the art as “zwitterions”, are electrically neutral molecules but carry formal positive and negative charges on different atoms in each valence bond structure according to valence bond theory. Furthermore, the molecular structure of the compounds of formula (Ia) and formula (Ib) can be represented by the four valence bond structures shown below, each placing the formal positive and negative charges on different atoms. Because of this resonance, the compounds of formula (Ia) and formula (Ib) are also described as “mesoionic”. Although for sake of simplicity, the molecular structure of formula (Ia) and formula (Ib) are depicted as a single valence bond structure herein, this particular valence bond structures are to be understood as representative of all four valence bond structures relevant to bonding in molecules of compounds of formula (Ia) and formula Ib. Therefore reference to formula (Ia) and formula (Ib) herein relates to all four applicable valence bond structures and other (e.g., molecular orbital theory) structures unless otherwise specified.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

An anion part of the salt in case the compound of formula (Ia) or formula (Ib) is a cationic or capable of forming a cation can be inorganic or organic. Alternatively, a cation part of the salt in case the compound of formula (Ia) or formula (Ib) is anionic or capable of forming anion can be inorganic or organic. Examples of inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates, and hydrogen sulfate. Examples of organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.

Metal ions in metal complexes of the compound of formula (Ia) or formula (Ib) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume.

In one another embodiment of the present invention discloses the compound of formula (Ia) or formula (Ib) in the composition with one or more inert carriers for controlling or preventing against animal pests.

In one another embodiment of the present invention discloses the compound of formula (Ia) or formula (Ib) agriculturally acceptable salts, metal complexes, constitutional isomers, stereoisomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof composition with the excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.

Compounds selected from formula (Ia) or formula (Ib), (including all stereoisomers, N-oxides, and salts thereof), typically exist in more than one form, and formula (Ia) or formula (Ib) thus includes all crystalline and non-crystalline forms of the compounds that formula (Ia) or formula (Ib) represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments that represent essentially a single crystal type and embodiments that represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by formula (Ia) or formula (Ib) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (Ia) or formula (Ib). Preparation and isolation of a particular polymorph of a compound represented by formula (Ia) or formula (Ib) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

The present disclosure also relates to the compound of formula (Ia) or formula (Ib) in the composition comprising at least one active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertiliers and nutrients. The compounds used in the composition and combination with the compound of formula (Ia) or formula (Ib) are also termed as active compatible compounds.

The concentration of the compound of the present disclosure in the composition ranges from 0.01 % to 90% by weight concerning the total weight of the composition, preferably from 5 to 50% by weight concerning the total weight of the composition.

These present compounds and compositions are thus useful agronomically for protecting field crops from phytophagous invertebrate pests, and also nonagronomically for protecting other horticultural crops and plants from phytophagous invertebrate pests. This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits.

The compounds of formula (Ia) or formula (Ib), their N-oxides and their salts are especially suitable for efficiently combating the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ipsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittella, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Helicoverpa armigera, Helicoverpa virescens, Helicoverpa zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

Beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica undecimpunctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus; cockroaches (Blattaria Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa; fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera oleoptrata, millipedes (Diplopoda), e.g. Narceus spp., Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus and Solenopotes capillatus.Collembola (springtails), e.g. Onychiurus ssp.

They are also suitable for controlling Nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

The compounds of formula (Ia) or formula (Ib) and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.

Yet another embodiment of present invention provides the compound of formula (Ia) or formula (Ib) is useful for controlling insects selected form sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species:

Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, Diptera, e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantii and Viteus vitifolii.

In one another embodiment of the present invention involves the conversion of a compound of formula (Ia) or formula (Ib) or its N-oxides and salts into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, Tand F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to a high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earth, e.g. silicates, silica gels, talc, kaolin, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as an emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers and Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the formula (Ia) or formula (Ib) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, Tand F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and watersoluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)
5-25 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives dispersion.

iii) Emulsifiable concentrates (EC)
15-70 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)
5-40 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water using an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsion (ME) 5-20 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a dior triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(methyl acrylate) microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a Formula (Ia) or Formula (Ib) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS)
1-10 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.

xii) Granules (GR, FG)
0.5-30 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xiii) Ultra-low volume liquids (UL)
1-50 wt% of a formula (Ia) or formula (Ib) or an N-oxide or salt thereof are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.

The compositions types (i) to (xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.

In one another embodiment of present invention provides a agrochemical compositions compound of formula (Ia) or formula (Ib), which comprise active substance between 0.01 and 95% by weight, preferably between 0.1 and 90%, and more preferably between 1 and 70 %, in particular between 10 and 60 by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying or treating formula (Ia) or formula (Ib) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, formula (Ia) or formula (Ib) or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.

In one embodiment, the present invention provides a composition comprising a biologically effective amount of the compound of formula (Ia) or (Ib) and at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients. The compounds used in the composition and in combination with the compound of formula (Ia) or (Ib) are also termed as active compatible compounds.

The known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of the formula (Ia) or (Ib) of the present disclosure. For example, fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO2016156129 and/or WO2017153200 can be combined with at least one compound of formula (Ia) or (Ib) of the present disclosure.

The fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in WO2016156129 and or WO2017153200 are incorporated herein by way of reference as non-limiting examples to be combined with at least one compound of the formula (Ia) or (Ib) of the present disclosure.

Particularly, the compounds of the present invention can be mixed with at least one additional biological active compatible compound (mixing partner) which includes but is not limited to insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility.

Examples of such biologically active compounds or agents/mixing partners with which the compounds of formula (Ia) or (Ib) of the present invention can be combined/formulated are disclosed in the WO2019072906A1 (page 27 to 37).

In one embodiment, the biological agents for mixing with compounds of the present invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.

In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent having a similar spectrum of control but a different mode of action. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus of the plant with a biologically effective amount of a compound of the invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.

When applying formula (Ia) or formula (Ib) and a component 2 sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.

Applications: The animal pest, i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with compounds of formula (Ia) or formula (Ib), their N-oxides and salts or composition(s) containing them by any application method known in the art. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).

The compounds of the invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of at least one compound of the invention. The term “crop” refers both to growing and harvested crops.

The compounds of the invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

The compounds of the invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with a insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.

The invention also includes a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of the invention or a composition comprising such a compound.

Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of at least one compound of the invention. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of the invention may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of at least one compound of the invention. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant). “Locus” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.

The term “plant propagation material” is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

The term “cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligoor polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties(e.g. as disclosed in Biotechnol Prog. 2001 Jul-Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1):57-66, Nat Protoc. 2007;2(5): 1225-35., Curr Opin Chem Biol. 2006 Oct;10(5):487-91. Epub 2006 Aug 28, Biomaterials. 2001 Mar; 22(5):405-17, Bioconjug Chem. 2005 Jan-Feb; 16(1):113-21).

The term “cultivated plants” is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A 0242236, EP-A 242246) or oxynil herbicides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as a-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato).

In general, “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.

For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 1 g to 1000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

The compounds of the invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait or plant part).

The compounds of the invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non-crop pests, compounds of the invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fishor blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligoor polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5 weight % of active compound.

Formulations of compounds of the invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250 °C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

The compounds of the invention and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula (Ia) or formula (Ib) and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are ?,?-Diethyl-meta-toluamide (DEET), N,Ndiethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as (+/-)-3-allyl-2-methyl4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (-)-l-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.

The compounds of the invention and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electrie wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of the invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, a compound of the invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

Seed treatment
The compounds of the invention are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plant's roots and shoots against soil pests and foliar insects.

The compounds of the invention are particularly useful for the protection of the seed from soil pests and the resulting plant's roots and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.

The invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedlings' roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the invention thereof. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

The invention also comprises seeds coated with or containing the active compound.
The term “coated with and/or containing” generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the compounds of the invention may be used for treating seed from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

For example, the compound of the invention can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, US 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 142 924, EP-A 193 259).

Furthermore, the compound of the invention can be used for the treatment of seed from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, and WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).

The seed treatment application of the compound of the invention is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
Compositions which are especially useful for seed treatment are e.g.:
A. Soluble concentrates (SL, LS)
B. Emulsions (EW, EO, ES)
C. Suspensions (SC, OD, FS)
D. Water-dispersible granules and water-soluble granules (WG, SG)
E. Water-dispersible powders and water-soluble powders (WP, SP, WS)
F. Gel-Formulations (GF)
G. Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

Seed treatment formulations may additionally comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo and copolymers, polyethyleneamines, polyethyleneamides and polyethylenepyrimidines, polysaccharides like celluloses, tylose and starch, polyolefin homo and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

An example of a gelling agent is carrageen (Satiagel®).

In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed. The invention therefore also provides to seed comprising a compound of the formula (Ia) or formula (Ib), or an agriculturally useful salt of Ia or Ib, as defined herein. The amount of the formula (Ia) or formula (Ib) or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

Animal health
The compounds of formula (Ia) or formula (Ib), their N-oxides and/or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.

One object of the invention is therefore to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is to provide pesticides for animals that may be used in lower doses than existing pesticides. Another object of the invention is to provide pesticides for animals, which provide a long residual control of parasites.

The invention also relates to compositions containing a parasiticidally effective amount of at least one compound of formula (Ia) or formula (Ib), N-oxide or veterinarily acceptable salt thereof and an acceptable carrier, for combating parasites in and on animals.

The invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically, or parenteral administering or applying to the animals a parasiticidally effective amount of a compound of the invention or a composition comprising it.
The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the invention or a composition comprising it.

Activity of compounds against agricultural pests does not suggest their suitability for control of endoparasites and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly it has now been found that compounds of the invention are suitable for combating endoparasites and ectoparasites in and on animals.

Compounds of the invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh and salt-water fish such as trout, carp and eels.

Compounds of the invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of the invention and compositions comprising them are suitable for systemic and/or non-systemic control of ectoparasites and/or endoparasites. They can be active against all or some stages of development. The compounds of the invention are especially useful for combating ectoparasites.

The compounds of the invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,
flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pi pi ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp, Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus, Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp, Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:
Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp, Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp, Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp, Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp., and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The compounds of formula (Ia) or formula (Ib) and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of the compounds of formula (Ia) or formula (Ib) and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of the invention and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of the invention and compositions containing them for combating fleas is especially preferred.
The use of the compounds of the invention and compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The compounds of the invention also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

Administration of the compounds of the invention is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, compounds of the invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of the invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the invention, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of the invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the invention may be formulated into an implant for subcutaneous administration. In addition the compound of the invention may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the invention.

The compounds of the invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compound of the invention. In addition, the compounds of the invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are: Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels; Emulsions and suspensions for oral or dermal administration; semi-solid preparations; Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base; Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketones such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or noctylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, and tocopherol.

Suitable light stabilizers are, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin. Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are:
Liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C8-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono and diglycerides of the C8-C10 fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof. Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are: non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; Anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like. The compositions which can be used in the invention generally comprise from about 0.001 to 95% of the compound of the invention.

Generally it is favorable to apply the compounds of the invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day. Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight. Preparations are diluted before use contains the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight. Furthermore, the preparations comprise the compounds of the invention against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
In a preferred embodiment, the compositions comprising the compounds of the invention are applied dermally/topically.

In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release compounds of the invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of the invention. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 2003/086075.

The invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

CHEMISTRY EXAMPLES:
General Procedures:
The compound of formula (Ia) can be prepared by one or other of the following methods. The definitions of Q1, Q2, G, W, A and Y in the compounds of formulae (Ia) and 1–6 below are as defined above in the summary of the invention unless otherwise noted.
As shown in scheme 1, compounds of formula (Ia), wherein W and A are O involves coupling of an acid of formula 1 (or its acid salt) with an acid chloride of formula 2 in the presence of an organic base and or a solvent such as pyridine. These reactions are typically run at 0 °C to 25 °C. In a subsequent step, compound of formula (Ia) wherein A is O can be converted to compound of formula (Ia) wherein A is S using a variety of standard thiating reagents such as phosphorus pentasulfide or 2,4-bis(4-methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent).

Scheme 1

As shown in scheme 2, compounds of formula (Ia) can also be prepared by coupling of an acid of formula 1 (or its acid salt) with an acid anhydride of formula 3 in the presence of a base and or a solvent such as pyridine. These reactions are typically run at 0 °C to 25 °C.
Scheme 2

The acid of formula 1 can be prepared by acid or base mediated hydrolysis of corresponding ester of formula 6 which in turn can be synthesized by N-alkylation of an amine of formula 4 and alkyl bromo acetate of formula 5 using an inorganic base such as potassium carbonate in a solvent like acetonitrile at 25 °C. Amine of formula 4 can be prepared by a protocol reported in WO2018177970A1.

Scheme 3

Experimental procedure and data:
All 1H NMR spectra were recorded in the respectively indicated solvents, and the chemical shifts are
reported in d units downfield from the internal standard tetramethylsilane (TMS). Inter proton coupling constants are reported in Hertz (Hz).

Example-1
Preparation of 5-acetyl-3-(2-chlorothiazol-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate:
Step-A: Preparation of tert-butyl 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetate
To a stirred solution of tert-butyl 2-bromoacetate (0.84 g, 4.3 mmol) in acetonitrile (3 mL) at 25 °C, potassium carbonate (0.89 g, 6.4 mmol) was added followed by addition of 4-(2-chlorothiazol-5-yl)-N-methylthiazolidin-2-imine (1.0 g, 4.3 mmol) and resulting mixture was stirred at same temperature for 5 h and then at 80 °C for 16 h. Upon completion of the reaction, the volatiles were evaporated under reduced pressure and crude was purified by silica gel column chromatography using 0–5% acetone in hexane as an eluent to afford tert-butyl 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetate (1.03 g, 2.9 mmol, 69% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.72–7.78 (m, 1H), 5.25 (t, J = 6.5 Hz, 1H), 4.02 (d, J = 17.4 Hz, 1H), 3.70 (dd, J = 11.2, 6.6 Hz, 1H), 3.50 (d, J = 17.4 Hz, 1H), 3.24 (dd, J = 11.2, 6.6 Hz, 1H), 2.89–2.97 (m, 3H), 1.37 (s, 9H).

Step-B: 2-(4-(2-Chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid
To a stirred solution of tert-butyl 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetate (0.25 g, 0.7 mmol) in dichloromethane (4 mL), trifluoroacetic acid (1.1 mL, 20 mmol) was added at 0 °C. After stirring for 1 h at 0 °C, reaction temperature was raised to 25 °C and stirred for 16 h. After completion of reaction, volatiles were evaporated under reduced pressure and residue was azeotropically co-evaporated with toluene to isolate crude (2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid (0.21 g, 0.7 mmol, 97% yield). Crude acid thus obtained was used as such for further transformations.

Step-C: Preparation of 5-acetyl-3-(2-chlorothiazol-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
To a stirred solution of 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid (0.45 g, 1.5 mmol) in acetic anhydride (3 mL), pyridine (0.2 mL, 3.0 mmol) was added at 25 °C. After 4 h stirring at 25 °C, reaction temperature was raised to 80 °C and stirring was continued for 16 h. Upon completion of reaction, the reaction mixture was quenched by slow addition of saturated sodium bicarbonate solution (20 mL). The crude product was isolated twice with dichloromethane (10 mL). Combined dichloromethane layer was washed twice with water (5 mL) followed by brine solution (5 mL), dried over sodium sulphate and evaporated under reduced pressure. The residual material was purified by silica gel column chromatography using 0–10% acetone in hexane, followed by 0–10% methanol in dichloromethane as an eluent to afford 5-acetyl-3-(2-chlorothiazol-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate (0.08 g, 0.3 mmol, 17% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.72 (d, J = 1.0 Hz, 1H), 6.63 (d, J = 7.8 Hz, 1H), 4.39 (dd, J = 12.0, 7.6 Hz, 1H), 4.12 (d, J = 12.0 Hz, 1H), 3.22 (s, 3H), 2.17 (s, 3H); LC/MS (m/z) 315.95 [M]+

Example-2: Preparation of 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2,2,2-trifluoroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
To a solution of 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid (0.3 g, 1.0 mmol) and trifluoroacetic anhydride (2.9 mL, 20.6 mmol) in dichloromethane (4 mL), triethylamine (0.6 mL, 4.1 mmol) was added slowly at 0 °C. After stirring at 0 °C for 10 min, reaction temperature was raised to 25 °C and stirring was continued at same temperature for 18 h. After completion of reaction, the reaction mixture was diluted with dichloromethane (10 mL) and washed twice with saturated sodium bicarbonate solution (10 mL) followed by water (10 mL). The dichloromethane layer was dried over sodium sulphate and evaporated under reduced pressure. The resulting crude material was purified by silica gel column chromatography using 0–10% acetone in hexane followed by 0–10% methanol in dichloromethane as an eluent to afford 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2,2,2-trifluoroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate (0.16 g, 0.4 mmol, 42% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.73 (d, J = 0.6 Hz, 1H), 6.65 (dd, J = 22.8, 15.1 Hz, 1H), 4.44 (dd, J = 11.9, 7.6 Hz, 1H), 4.12 (d, J = 12.5 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 369.75 [M]+

Examples 3 and 4 were also prepared by reacting 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid with respective acid anhydrides using a similar process as described for example-2/step-C.

Example-3: 3-(2-Chlorothiazol-5-yl)-7-methyl-5-(2,2,2-trichloroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.12 g, 0.3 mmol, 39% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.74 (d, J = 0.6 Hz, 1H), 6.74 (d, J = 7.6 Hz, 1H), 4.46 (dd, J = 12.0, 7.6 Hz, 1H), 4.14 (d, J = 12.0 Hz, 1H), 3.26 (s, 3H); LC/MS (m/z) 419.60 [M]+

Example-4: 3-(2-Chlorothiazol-5-yl)-5-(2,2-difluoroacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.15 g, 0.4 mmol, 42% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.75 (d, J = 0.7 Hz, 1H), 6.78 (t, J = 54.5 Hz, 1H), 6.62 (d, J = 7.8 Hz, 1H), 4.46 (dd, J = 12.0, 7.8 Hz, 1H), 4.15 (d, J = 12.0 Hz, 1H), 3.25 (d, J = 4.2 Hz, 3H); LC/MS (m/z) 351.90 [M]+

Example-5: 3-(2-Chlorothiazol-5-yl)-7-methyl-5-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
To a solution of 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid (0.21 g, 0.7 mmol) in dichloromethane (8 mL), 2-(trifluoromethyl)benzoyl chloride (1.1 mL, 7.2 mmol) was added followed by slow addition of triethylamine (0.4 mL, 2.9 mmol) at 0 °C. After stirring for 10 min at 0 °C, reaction temperature was raised to 25 °C and stirring was continued for 16 h. After completion of the reaction, reaction mixture was diluted with dichloromethane (10 mL) and washed twice with saturated sodium bicarbonate solution (10 mL) followed by water (10 mL). Then dichloromethane layer was dried over sodium sulphate and evaporated under reduced pressure. Resulting crude material was purified by silica gel column chromatography using 0–60% ethyl acetate in hexane followed by 0–10% methanol in dichloromethane as an eluent to afford 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate (0.07 g, 0.2 mmol, 22% yield). 1H-NMR (400 MHz, DMSO-d6) 7.77 (d, J = 0.5 Hz, 1H), 7.70–7.72 (m, 1H), 7.54–7.64 (m, 2H), 7.29 (d, J = 7.6 Hz, 1H), 6.78 (d, J = 7.6 Hz, 1H), 4.50 (dd, J = 12.0, 7.6 Hz, 1H), 4.19 (d, J = 12.5 Hz, 1H), 3.17 (s, 3H); LC/MS (m/z) 445.95 [M]+

Examples 6 to 11 were also prepared by reacting 2-(4-(2-chlorothiazol-5-yl)-2-(methylimino)thiazolidin-3-yl)acetic acid with corresponding benzoyl chlorides using a similar process as described for example-5/step-C.

Example-6: 3-(2-Chlorothiazol-5-yl)-7-methyl-5-(4-nitrobenzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.15 g, 0.4 mmol, 30% yield). 1H-NMR (400 MHz, DMSO-d6) d 8.21 (dt, J = 9.0, 2.2 Hz, 2H), 7.89 (dt, J = 9.1, 2.1 Hz, 2H), 7.79 (d, J = 0.7 Hz, 1H), 6.83 (d, J = 7.6 Hz, 1H), 4.48 (dd, J = 12.0, 7.8 Hz, 1H), 4.20 (d, J = 12.0 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 422.95 [M]+

Example-7: 3-(2-Chlorothiazol-5-yl)-5-(3-fluoro-4-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.07 g, 0.1 mmol, 20% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.76–7.80 (m, 3H), 7.68 (d, J = 8.1 Hz, 1H), 6.82 (d, J = 7.6 Hz, 1H), 4.47 (dd, J = 12.0, 7.8 Hz, 1H), 4.19 (d, J = 12.0 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 463.85 [M]+

Example-8: 3-(2-Chlorothiazol-5-yl)-5-(4-fluoro-3-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.08 g, 0.2 mmol, 23% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.75–7.81 (m, 3H), 7.67 (d, J = 8.3 Hz, 1H), 6.81 (d, J = 7.6 Hz, 1H), 4.46 (dd, J = 11.9, 7.6 Hz, 1H), 4.18 (d, J = 12.2 Hz, 1H), 3.22 (s, 3H); LC/MS (m/z) 463.90 [M]+

Example-9: 3-(2-Chlorothiazol-5-yl)-7-methyl-5-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.13 g, 0.3 mmol, 29% yield). 1H-NMR (400 MHz, DMSO-d6) d 8.09 (s, 1H), 8.01 (d, J = 7.6 Hz, 1H), 7.79–7.83 (m, 2H), 7.63 (t, J = 7.8 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 4.48 (dd, J = 12.0, 7.6 Hz, 1H), 4.19 (d, J = 12.0 Hz, 1H), 3.24 (s, 3H); LC/MS (m/z) 445.95 [M]+

Example-10: 3-(2-Chlorothiazol-5-yl)-5-(2,4-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.07 g, 0. 2 mmol, 24% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.77 (s, 1H), 7.55 (d, J = 1.5 Hz, 1H), 7.38 (dd, J = 8.3, 1.5 Hz, 1H), 7.20 (d, J = 8.3 Hz, 1H), 6.74 (d, J = 7.3 Hz, 1H), 4.47 (dd, J = 11.9, 7.6 Hz, 1H), 4.19 (d, J = 12.2 Hz, 1H), 3.15 (s, 3H); LC/MS (m/z) 447.70 [M+H]+

Example-11: 3-(2-Chlorothiazol-5-yl)-5-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate: (0.06 g, 0.1 mmol, 20% yield). 1H-NMR (400 MHz, DMSO-d6) d 7.78 (s, 1H), 7.46–7.48 (m, 2H), 7.32–7.37 (m, 1H), 6.84 (d, J = 7.6 Hz, 1H), 4.47 (dd, J = 12.0, 7.8 Hz, 1H), 4.18 (d, J = 12.2 Hz, 1H), 3.24 (s, 3H); LC/MS (m/z) 413.75 [M]+

Table 1: Representative compounds of the present disclosure prepared according to the suitable methods as described in schemes and examples:

S.No. Name NMR Data
1 5-acetyl-3-(2-chlorothiazol-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.72 (d, J = 1.0 Hz, 1H), 6.63 (d, J = 7.8 Hz, 1H), 4.39 (dd, J = 12.0, 7.6 Hz, 1H), 4.12 (d, J = 12.0 Hz, 1H), 3.22 (s, 3H), 2.17 (s, 3H); LC/MS (m/z) 315.95 [M]+
2 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2,2,2-trifluoroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.73 (d, J = 0.6 Hz, 1H), 6.65 (dd, J = 22.8, 15.1 Hz, 1H), 4.44 (dd, J = 11.9, 7.6 Hz, 1H), 4.12 (d, J = 12.5 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 369.75 [M]+
3 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2,2,2-trichloroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.74 (d, J = 0.6 Hz, 1H), 6.74 (d, J = 7.6 Hz, 1H), 4.46 (dd, J = 12.0, 7.6 Hz, 1H), 4.14 (d, J = 12.0 Hz, 1H), 3.26 (s, 3H); LC/MS (m/z) 419.60 [M]+
4 3-(2-chlorothiazol-5-yl)-5-(2,2-difluoroacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.75 (d, J = 0.7 Hz, 1H), 6.78 (t, J = 54.5 Hz, 1H), 6.62 (d, J = 7.8 Hz, 1H), 4.46 (dd, J = 12.0, 7.8 Hz, 1H), 4.15 (d, J = 12.0 Hz, 1H), 3.25 (d, J = 4.2 Hz, 3H); LC/MS (m/z) 351.90 [M]+
5 3-(2-chlorothiazol-5-yl)-7-methyl-5-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.77 (d, J = 0.5 Hz, 1H), 7.70-7.72 (m, 1H), 7.54-7.64 (m, 2H), 7.29 (d, J = 7.6 Hz, 1H), 6.78 (d, J = 7.6 Hz, 1H), 4.50 (dd, J = 12.0, 7.6 Hz, 1H), 4.19 (d, J = 12.5 Hz, 1H), 3.17 (s, 3H); LC/MS (m/z) 445.95 [M]+
6 3-(2-chlorothiazol-5-yl)-7-methyl-5-(4-nitrobenzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 8.21 (dt, J = 9.0, 2.2 Hz, 2H), 7.89 (dt, J = 9.1, 2.1 Hz, 2H), 7.79 (d, J = 0.7 Hz, 1H), 6.83 (d, J = 7.6 Hz, 1H), 4.48 (dd, J = 12.0, 7.8 Hz, 1H), 4.20 (d, J = 12.0 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 422.95 [M]+
7 3-(2-chlorothiazol-5-yl)-5-(3-fluoro-4-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.76-7.80 (m, 3H), 7.68 (d, J = 8.1 Hz, 1H), 6.82 (d, J = 7.6 Hz, 1H), 4.47 (dd, J = 12.0, 7.8 Hz, 1H), 4.19 (d, J = 12.0 Hz, 1H), 3.23 (s, 3H); LC/MS (m/z) 463.85 [M]+
8 3-(2-chlorothiazol-5-yl)-5-(4-fluoro-3-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.75-7.81 (m, 3H), 7.67 (d, J = 8.3 Hz, 1H), 6.81 (d, J = 7.6 Hz, 1H), 4.46 (dd, J = 11.9, 7.6 Hz, 1H), 4.18 (d, J = 12.2 Hz, 1H), 3.22 (s, 3H); LC/MS (m/z) 463.90 [M]+
9 3-(2-chlorothiazol-5-yl)-7-methyl-5-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 8.09 (s, 1H), 8.01 (d, J = 7.6 Hz, 1H), 7.79-7.83 (m, 2H), 7.63 (t, J = 7.8 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 4.48 (dd, J = 12.0, 7.6 Hz, 1H), 4.19 (d, J = 12.0 Hz, 1H), 3.24 (s, 3H); LC/MS (m/z) 445.95 [M]+
10 3-(2-chlorothiazol-5-yl)-5-(2,4-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.77 (s, 1H), 7.55 (d, J = 1.5 Hz, 1H), 7.38 (dd, J = 8.3, 1.5 Hz, 1H), 7.20 (d, J = 8.3 Hz, 1H), 6.74 (d, J = 7.3 Hz, 1H), 4.47 (dd, J = 11.9, 7.6 Hz, 1H), 4.19 (d, J = 12.2 Hz, 1H), 3.15 (s, 3H); LC/MS (m/z) 447.70 [M+H]+
11 3-(2-chlorothiazol-5-yl)-5-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 1H-NMR (400 MHz, DMSO-d6) d 7.78 (s, 1H), 7.46-7.48 (m, 2H), 7.32-7.37 (m, 1H), 6.84 (d, J = 7.6 Hz, 1H), 4.47 (dd, J = 12.0, 7.8 Hz, 1H), 4.18 (d, J = 12.2 Hz, 1H), 3.24 (s, 3H); LC/MS (m/z) 413.75 [M]+

Table 2: These compounds of the present disclosure prepared according to the suitable methods as described in schemes and examples:

S.No. Name S.No. Name
1. 5-(2-cyanoacetyl)-7-methyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 25. 5-(2-(isobutylthio)acetyl)-7-methyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
2. 5-(2-ethoxy-2-oxoacetyl)-7-methyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 26. 5-(2-(2-methoxyethoxy)acetyl)-7-methyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
3. 7-methyl-5-(2-(methylthio)acetyl)-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 27. 5-(2-chloroacetyl)-7-methyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
4. 7-methyl-5-(3-(methylthio)propanoyl)-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 28. 7-methyl-5-pivaloyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
5. 5-(2-(isobutylthio)acetyl)-7-methyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 29. 5-acetyl-3-(6-chloropyridin-3-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
6. 5-(2-(2-methoxyethoxy)acetyl)-7-methyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 30. 3-(6-chloropyridin-3-yl)-7-methyl-5-(2,2,2-trifluoroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
7. 5-(2-chloroacetyl)-7-methyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 31. 3-(6-chloropyridin-3-yl)-7-methyl-5-(2,2,2-trichloroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
8. 7-methyl-5-pivaloyl-3-(2-chlorothiazol-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 32. 3-(6-chloropyridin-3-yl)-5-(2,2-difluoroacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
9. 5-acetyl-3-(pyrimidin-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 33. 3-(6-chloropyridin-3-yl)-7-methyl-5-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
10. 3-(pyrimidin-5-yl)-7-methyl-5-(2,2,2-trifluoroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 34. 3-(6-chloropyridin-3-yl)-7-methyl-5-(4-nitrobenzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
11. 3-(pyrimidin-5-yl)-7-methyl-5-(2,2,2-trichloroacetyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 35. 3-(6-chloropyridin-3-yl)-5-(3-fluoro-4-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
12. 3-(pyrimidin-5-yl)-5-(2,2-difluoroacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 36. 3-(6-chloropyridin-3-yl)-5-(4-fluoro-3-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
13. 3-(pyrimidin-5-yl)-7-methyl-5-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 37. 3-(6-chloropyridin-3-yl)-7-methyl-5-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
14. 3-(pyrimidin-5-yl)-7-methyl-5-(4-nitrobenzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 38. 3-(6-chloropyridin-3-yl)-5-(2,4-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
15. 3-(pyrimidin-5-yl)-5-(3-fluoro-4-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 39. 3-(6-chloropyridin-3-yl)-5-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
16. 3-(pyrimidin-5-yl)-5-(4-fluoro-3-(trifluoromethyl)benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 40. 3-(6-chloropyridin-3-yl)-5-(benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
17. 3-(pyrimidin-5-yl)-7-methyl-5-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 41. 5-(2-cyanoacetyl)-7-methyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
18. 3-(pyrimidin-5-yl)-5-(2,4-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 42. 5-(2-ethoxy-2-oxoacetyl)-7-methyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
19. 3-(pyrimidin-5-yl)-5-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 43. 7-methyl-5-(2-(methylthio)acetyl)-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
20. 3-(pyrimidin-5-yl)-5-(benzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 44. 7-methyl-5-(3-(methylthio)propanoyl)-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
21. 5-(2-cyanoacetyl)-7-methyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 45. 5-(2-(isobutylthio)acetyl)-7-methyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
22. 5-(2-ethoxy-2-oxoacetyl)-7-methyl-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 46. 5-(2-(2-methoxyethoxy)acetyl)-7-methyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
23. 7-methyl-5-(2-(methylthio)acetyl)-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 47. 5-(2-chloroacetyl)-7-methyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate
24. 7-methyl-5-(3-(methylthio)propanoyl)-3-(pyrimidin-5-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate 48. 7-methyl-5-pivaloyl-3-(6-chloropyridin-3-yl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-6-olate

Table 3: These compounds of the present disclosure prepared according to the suitable methods as described in schemes and examples:

S.No. Name S.No. Name
1. 3-(2-chlorothiazol-5-yl)-6-(2-ethoxy-2-oxoacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 11. 3-(pyrimidin-5-yl)-6-(2-ethoxy-2-oxoacetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
2. 3-(2-chlorothiazol-5-yl)-7-methyl-6-(3-(methylthio)propanoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 12. 3-(pyrimidin-5-yl)-7-methyl-6-(3-(methylthio)propanoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
3. 3-(2-chlorothiazol-5-yl)-6-(2-(isobutylthio)acetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 13. 3-(pyrimidin-5-yl)-6-(2-(isobutylthio)acetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
4. 3-(2-chlorothiazol-5-yl)-6-(2-(2-methoxyethoxy)acetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 14. 3-(pyrimidin-5-yl)-6-(2-(2-methoxyethoxy)acetyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
5. 3-(2-chlorothiazol-5-yl)-7-methyl-6-pivaloyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 15. 3-(pyrimidin-5-yl)-7-methyl-6-pivaloyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
6. 3-(2-chlorothiazol-5-yl)-7-methyl-6-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 16. 3-(pyrimidin-5-yl)-7-methyl-6-(3-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
7. 6-benzoyl-3-(2-chlorothiazol-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 17. 6-benzoyl-3-(pyrimidin-5-yl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
8. 3-(2-chlorothiazol-5-yl)-6-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 18. 3-(pyrimidin-5-yl)-6-(3,5-difluorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
9. 3-(2-chlorothiazol-5-yl)-6-(3,5-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 19. 3-(pyrimidin-5-yl)-6-(3,5-dichlorobenzoyl)-7-methyl-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
10. 3-(2-chlorothiazol-5-yl)-7-methyl-6-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate 20. 3-(pyrimidin-5-yl)-7-methyl-6-(2-(trifluoromethyl)benzoyl)-3,7-dihydro-2H-imidazo[2,1-b]thiazol-4-ium-5-olate
* Compound names generated using Chemdraw Professional 18.1

BIOLOGY EXAMPLES:
Example A: Plutella xylostella
Leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then diluted with 0.01% Triton-X solution to get the desired test concentration. Cabbage leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then transferred into the cells of bioassay trays. A single second instar larva was released into each cell and the tray was covered with a lid. The bio-assay trays were then kept under laboratory conditions at a temperature of 25 oC and a relative humidity of 70%. Observations on dead, moribund and alive larvae were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund larvae and comparing the result with untreated control. The compounds 2, 3, 9 and 11 were recorded = 70 per cent mortality @ 300PPM.

Example B: Bemisia tabaci
Leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then diluted with 0.01% Triton-X solution to get the desired test concentration. Brinjal leaves were dipped in the compound solution for 10 seconds; shade dried for 20 min and then placed, with the abaxial side of the leaf up, on 4 ml of a 1 % agar-agar solution in respective perforated container caps. Known numbers of freshly emerged whitefly adults were collected, using a modified aspirator, and released into a perforated container in which the cap containing the treated leaf was placed. The containers were kept in a plant growth chamber at a temperature of 25 oC and relative humidity of 70%. Observations on dead, moribund and alive adults were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund adults and comparing the result with untreated control. The compound 1 recorded = 70 per cent mortality @ 300PPM.

Example C: Myzus persicae
Leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then diluted with 0.01% Triton-X solution to the desired test concentration. Capsicum leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then placed, with the abaxial side of the leaf up, in single cells of a bio-assay tray containing 4 ml of a 1 % agar-agar solution. Known numbers of third instar nymphs, collected in petri plates, were released into the cell with the treated leaf and the cell was covered with a perforated lid for better aeration. The trays were kept in a plant growth chamber at a temperature of 25 oC and a relative humidity of 70%. Observations on dead, moribund and alive nymphs were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the result with untreated control. The compounds 1, 2, 8, 9 and 11 recorded = 70 per cent mortality @ 300PPM.

Example D: Nilaparvata lugens
Seedling dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, and then diluted with 0.01% Triton-X solution to the desired test concentration. Paddy seedlings were dipped in the compound solution for 10 seconds, shade dried for 20 min and then the seedlings were placed in glass test tubes with the roots kept in water. 15 third instar nymphs were released into each test tube and the tubes were kept in a plant growth chamber at a temperature of 25 oC and relative humidity of 75%. Observations on dead, moribund and alive nymphs were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the result with untreated control. The compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 11 recorded = 70 per cent mortality @ 300PPM.

Wholeplant Assay/Green house Experiments:
Example 1. Nilaparvatha lugens
A whole plant assay was conducted in the greenhouse, in which the required quantity of the compound was weighed & dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then diluted with 0.01% Triton-X solution to get the desired test concentration. Rice seedling, 20-25 days old, grown in the greenhouse were used for the treatments. For each dose 3 plants were taken. The application was done in the greenhouse by using a state of the art Generation-3 sprayer. The treated plants were allowed to dry and then moved to the laboratory. The plants were kept in containers with water to maintain humidity and the whole plant was covered with a mylar sheet for restricting the insect movement. Fifteen 3rd instar nymphs were released at the bottom of the plant. The caged plants were covered at the top with a muslin cloth for better air ventilation. The observation on dead, moribund and alive nymphs was recorded 72 hours after the treatment. Percent mortality was calculated by combining dead and moribund nymphs and comparing the result with untreated control. The compounds 1, 2, 3, 4, 5, 6, 10 and 11 recorded = 70 per cent mortality @ 200PPM.

,CLAIMS:WE CLAIM:
1. A compound of formula (Ia)

wherein,
W is selected from O or S,
A is selected from O or S,
Y is selected from R1, -OR1, - N(R2)(R3), or -N(R2)(R3)-N(R2)(R3);
G is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, CHO, C(O)NR2R3, C(=S)NR2R3, SR2(O)n(=NR2), S(O)n(NR2R3), N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R3, NR3SO2NR2R3, C(=NR2)R3, NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, C(=NOR2)R3 C(=NNR2R3)R4, C(=NN(C(=O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(=O)(=NR2)R3, SO2NR3C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR3)R4, P(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR2)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 cycloalkylalkyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 is selected from C(R3)(R4)-, -C(R3)(R4)C(R3)(R4)-, -O-, -S(O)n, NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, or C4-C10 cycloalkynyl, wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q2 is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, OCN, SCN, CHO, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, C(O)R3R4, C(O)R2OR3, NR2R3, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, OC(O)R2, OC(O)OR3, OC(O)NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R4, NR2SO2NR4R5, Si(R3R4), C(=NR2)R3, C(=NOR2)R3, C(=NNR2R3)R4, C(=NN(C(O)R2)R3)R4, C(=NN(C(O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(O)(=NR3)R4, SO2NR2C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR2)R4, OP(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR3)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, SR2(O)n(=NR3), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl,C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl,, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 and Q2 may form a 4 to 7 membered ring, taken together with the carbon and nitrogen of the imidazole ring in formula (Ia), wherein each remaining ring member is selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are independently selected from S(=O)m, wherein the ring is substituted with one or more Het;

Het is 3 to 10 membered heterocyclic ring or a 7 to 11 membered heterocyclic ring system, each ring or ring system member selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein each ring or ring system is optionally substituted with at least one substituent independently selected from R1;
W2 is selected from O or S;
wherein,
R1 is selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, SR2(O)n(=NR2), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 alkylsulfinylalkyl, C1-C8 alkylsulfonylalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R5;
or
R1 is 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, SR2(O)n(=NR2), S(O)n(NR2R3), S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R5;

R2, R3 and R4 is independently selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C3-C10 cycloalkylcycloalkyl, C3-C10 alkylcycloalkylalkyl or C3-C6 cycloalkenyl, which is optionally substituted by R1
or
R2 and R3 are taken together with the contiguous linking nitrogen to form a 5 to 7 membered heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
or
R3 and R4 are taken together with the contiguous linking carbon atoms to form a 5 to 7 membered carbocyclic or heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
R5 is selected from halogen, cyano, nitro, SF5, SCN, amino, hydroxy, COOH, SH, C1-C6-alkyl, C2-C6-alkynyl, C1-C6-alkylamino, di-(C1-C6)-alkylamino, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyloxy, cyano-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6¬ alkylaminocarbonyl and di-(C1-C6)-alkylaminocarbonyl;
or
R5 is a 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, S(O)n, S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R1;
“m” is an integer ranging from 0 to 3;
“n” is an integer ranging from 0 to 2;
or salts, metal complexes, N-oxides, isomers, or polymorphs thereof.

2. The compound of formula (Ia) as claimed in claim 1, in a composition with one or more inert carriers for controlling or preventing pests.

3. An agricultural and/or veterinary composition comprising at least one compound of formula (Ia) as claimed in claim 1.

4. A process for the preparation of a composition for treating or protecting animals against infestation or infection by parasites which comprises mixing a parasiticidally effective amount of at least one compound of formula (Ia) as claimed in claim 1.

5. A method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (Ia) as claimed in claim 1.

6. A method for protecting crops from attack or infestation by pests, which comprises contacting the crop with a pesticidally effective amount of at least one compound of formula (Ia) as claimed in claim 1, N-oxide or salt thereof.

7. A method for the protection of seeds from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of formula (Ia) as claimed in claim 1, N-oxide or salt thereof.

8. A method for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasitically effective amount of at least one compound of formula (Ia) as claimed in claim 1, N-oxide or veterinary acceptable salt thereof.

9. The compound of formula (Ia) according to any of above claims, in a composition comprising one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients.

10. The compound of formula (Ia) as claimed in claim 1, wherein the concentration of said compound in the composition ranges from 0.1 % to 99% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.

11. The method as claimed in claim 8, consists of applying effective dosages of compounds claimed in claims 1 to 2 in amounts ranging from 1 gai to 5000 gai per hectare in agricultural or horticultural crops.

12. The use of a compound of formula (Ia) as claimed in claim 1, N-oxide or veterinarily acceptable salt thereof for the preparation of a medicament for treating or protecting animals against infestation or infection by parasites.

13. Use of the compound of formula (Ia) as claimed in claim 1, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.

14. A treated seed comprising a compound of claim 1 in an amount of from about 0.0001% to 1% by weight of the seed before treatment.

15. The use of a compound of formula (Ia) as claimed in claim 1, N-oxide or veterinarily acceptable salt thereof for combating parasites in and on animals.

16. Seeds comprising at least one compound of formula (Ia) as claimed in claim 1, N-oxide or salt thereof.

17. The use of a compound of formula (Ia) as claimed in claim 1, N-oxide or salt thereof for combating pests.

18. A compound of formula (Ib)

wherein,
W is selected from O or S,
A is selected from O or S,
Y is selected from R1, -OR1, - N(R2)(R3), or -N(R2)(R3)-N(R2)(R3);
G is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, CHO, C(O)NR2R3, C(=S)NR2R3, SR2(O)n(=NR2), S(O)n(NR2R3), N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R3, NR3SO2NR2R3, C(=NR2)R3, NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, C(=NOR2)R3 C(=NNR2R3)R4, C(=NN(C(=O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(=O)(=NR2)R3, SO2NR3C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR3)R4, P(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR2)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 cycloalkylalkyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 is selected from C(R3)(R4)-, -C(R3)(R4)C(R3)(R4)-, -O-, -S(O)n, NR2R3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, or C4-C10 cycloalkynyl, wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q2 is selected from hydrogen, halogen, cyano, hydroxy, nitro, SF5, OCN, SCN, CHO, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, C(O)R3R4, C(O)R2OR3, NR2R3, C(O)NR2R3, C(=S)NR2R3, SO2NR2R3, OC(O)R2, OC(O)OR3, OC(O)NR2R3, N(R2)C(O)R3, N(R2)C(O)OR3, N(R2)C(O)NR2R3, OSO2R2, OSO2NR2R3, NR2SO2R4, NR2SO2NR4R5, Si(R3R4), C(=NR2)R3, C(=NOR2)R3, C(=NNR2R3)R4, C(=NN(C(O)R2)R3)R4, C(=NN(C(O)OR2)R3)R4, ON=CR3R4, ONR2R3, S(O)(=NR3)R4, SO2NR2C(O)NR2R3, P(=W2)R3R4, OP(=W2)R3R4, OP(=W2)(OR2)R4, OP(=W2)(OR2)OR3, N=CR3R4, NR2N=CR3R4, NR2NR2R3, NR2C(=W2)NR2R3, NR2C(=NR3)NR2R3, NR2NR3C(=W2)NR2R3, NR2NR3SO2NR2R3, SR2(O)n(=NR3), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl,C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl,, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R1;

Q1 and Q2 may form a 4 to 7 membered ring, taken together with the carbon and nitrogen of the imidazole ring in formula (Ib), wherein each remaining ring member is selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are independently selected from S(=O)m, wherein the ring is substituted with one or more Het;

Het is 3 to 10 membered heterocyclic ring or a 7 to 11 membered heterocyclic ring system, each ring or ring system member selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein each ring or ring system is optionally substituted with at least one substituent independently selected from R1;

W2 is selected from O or S;
wherein,
R1 is selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, SR2(O)n(=NR2), S(O)n(NR2R3), C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C4-C10 cycloalkynyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, C4-C10 halocycloalkynyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy, C1-C8 alkoxyalkyl, C1-C8 alkoxyalkoxy, C3-C8 cycloalkoxy, C3-C10 cycloalkoxyalkyl, C4-C10 cycloalkylalkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 haloalkoxylalkyl, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylthioalkyl, C1-C8 alkylsulfinylalkyl, C1-C8 alkylsulfonylalkyl, C1-C8 haloalkylthio, C1-C8 haloalkylsulfinyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylthio, C3-C8 cycloalkylsulf?nyl, C3-C8 cycloalkylsulfonyl, C4-C10 cycloalkylalkylthio, C4-C10 cycloalkylalkylsulfinyl, C4-C10 cycloalkylalkylsulfonyl, C2-C8 alkenylthio, C2-C8 alkenylsulf?nyl, C2-C8 alkenylsulfonyl, C2-C8 alkynylthio, C2-C8 alkynylsulfinyl, C2-C8 alkynylsulfonyl, C1-C8 alkylcarbonyl, C1-C8 haloalkylcarbonyl, or C3-C8 cycloalkylcarbonyl; wherein aforementioned groups may be optionally substituted with at least one substituent independently selected from R5;
or
R1 is 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, SR2(O)n(=NR2), S(O)n(NR2R3), S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R5;

R2, R3 and R4 is independently selected from hydrogen, halogen, cyano, nitro, SH, SF5, SCN, amino, hydroxy, COOH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C3-C10 cycloalkylcycloalkyl, C3-C10 alkylcycloalkylalkyl or C3-C6 cycloalkenyl, which is optionally substituted by R1
or
R2 and R3 are taken together with the contiguous linking nitrogen to form a 5 to 7 membered heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
or
R3 and R4 are taken together with the contiguous linking carbon atoms to form a 5 to 7 membered carbocyclic or heterocyclic ring, each ring contain ring members are selected from C, C=O, C=S, S(O)n, O and N, wherein each ring is optionally substituted by R1;
R5 is selected from halogen, cyano, nitro, SF5, SCN, amino, hydroxy, COOH, SH, C1-C6-alkyl, C2-C6-alkynyl, C1-C6-alkylamino, di-(C1-C6)-alkylamino, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyloxy, cyano-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6¬ alkylaminocarbonyl and di-(C1-C6)-alkylaminocarbonyl;
or
R5 is a 3 to 10 membered ring or a 7 to 11 membered ring system, each ring or ring system containing ring members are selected from C, C=O, C=S, S(O)n, S, O and N, wherein each ring or ring system is optionally substituted with one or more than one substituents independently selected from R1;
“m” is an integer ranging from 0 to 3;
“n” is an integer ranging from 0 to 2;
or salts, metal complexes, N-oxides, isomers, or polymorphs thereof.

Dated this 31st day of October, 2019.

VAIBHAV VUTTS
of VUTTS & ASSOCIATES LLP
AGENT FOR THE APPLICANT
IN/PA No. 1215