Abstract: The present invention disclosed fluoralkenyl compounds of general formula (I), wherein; R, R1, R2, R3, A and integers n, m and k are as defined in description. The present invention further discloses use of the compounds of general formula (I) to protect crops by controlling or preventing against undesired phytopathogenic microorganisms such as nematodes and phytopathogenic fungi.
TITLE: FLUORALKENYL COMPOUNDS, PROCESS FOR PREPARATION AND USE
THEREOF
FIELD OF THE INVENTION
The present invention relates to novel fluoralkenyl compounds and their use as crop protection agents.
BACKGROUND OF THE INVENTION
WO200102378, US 3,518,172 describes trifluorobutenyl compounds which have nematicidal activity. JP500037/1988 (WO 86/07590) describes polyhaloalkene compounds which have nematicidal activity. WO95/24403 describes that 4,4-difluorobutenyl compounds have nematicidal activity. JP176141/1997 mentions thiazole compounds having insecticidal and acaricidal activity. WO2017002100, WO2004095930, WO2004095929, DE10254876,
WO2004005268, WO2003049541, WO2003029231, WO2002006259, WO2002006257, WO2002006256, WO2001066529, US354979, US3891662, US3780050, US3700668, US3697536, US3692912, US3666818, US3654293 also describe polyhaloalkene compounds which have nematicidal activity. WO94/06782 discloses benzthiazoles and benzoxazoles having nematicidal, insecticidal, acaricidal and fungicidal properties. WO94/06777 discloses pyrimidine derivatives having nematicidal, insecticidal, acaricidal and fungicidal properties.
The control of damages to crops caused by phytopathogenic microorganisms and pests is extremely important in achieving high crop efficiency. For instance, plant disease damage to ornamental, vegetable, field, cereal and fruit crops can cause significant reduction in productivity and thereby result in increased cost to the consumer. Many products are commercially available to control such damages. The need continues for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action.
The effectiveness of the diflurobutenes, trifluorobutenes and other compounds described in the prior art is good, but are not fully satisfactory in various cases. Therefore, it is always of high interest in agriculture to find novel pesticidal compounds in order to avoid and/or control the development of microorganisms such as fungal or bacterial pathogens or pests being resistant to known active ingredients. It is therefore of high interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compound to be used, whilst at the same time maintaining an effectiveness at least equivalent to the already known compounds.
The present invention describes compounds of formula (I) which possess the above mentioned effects or advantages. Such compounds of formula (I), namely fluoralkenyl compounds wherein the heterocyclic ring is substituted according to the invention, show unexpected and significantly higher activity against undesired microorganisms such as fungal or bacterial pathogens or against pests such as nematodes or insects.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides a fluoralkenyl compound of the general formula (I),
Wherein; R, R1, R2, R3, A and integers n, m and k are as defined in detailed description and their use for controlling or preventing agricultural crops and/or horticultural crops against nematodes and phytopathogenic fungi.
DESCRIPTION
DEFINITIONS
The terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present 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.
The transitional phrase “consisting essentially of" is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of" occupies a middle ground between “comprising” and “consisting of".
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 present 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 “pesticide” in each case also always comprises the term “crop protection agent”.
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 “helminths” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Trematoda), acanthocephala and tapeworms (Cestoda).
The term “undesired microorganisms” or “phytopathogenic microorganisms” such as fungal or bacterial pathogens includes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae respectively.
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 present 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 provide protection of 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.
The 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 meaning of various terms used in the description shall now be illustrated:
In the above description, 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. Non limiting 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 1-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 C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6 alkenes. Non limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1 -methyl ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1-propenyl, 2-methyl-1-propenyl, 1-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, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-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, 1-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, 1-
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,
1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-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-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and the different isomers. The term “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.
The term “alkynyl”, used either alone or in compound words includes branched or straight-chain C2 to C24 alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, most preferably C2 to C6 alkynes. Non limiting 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, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,
1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-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. The term“ Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
The term “cyclic alkyl” or “cycloalkyl” means alkyl closed to form a ring. Non limiting examples include but are not limited to cyclopropyl, cyclobutyl, 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. Non limiting examples include but are not limited to 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. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
The term “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 “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-dimethyl ethoxy, 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 1-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 “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 1-ethyl-2-methylpropylthio and the different isomers.
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 “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.
Non-limiting 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” and “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 1,1,1-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 terms “haloalkylthio” or “haloalkylsulfanyl” 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, dichloro fluoromethylthio, 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 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
Non limiting examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non limiting examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.
The term “alkylthioalkyl” denotes alkylthio substitution on alkyl. Non limiting examples of “alkylthioalkyl” include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. The term “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.
The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to “alkylthioalkyl” or cycloalkylalkylamino.
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.
The term “alkoxycarbonylalkylamino” denotes alkoxy carbonyl substitution on alkyl amino.
The term “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino.
The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously. Non limiting examples of “alkylsulfinyl” include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methyl ethylsulphinyl, 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.
Non limiting 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 1-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.
The term “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples. The term “ring” or “ring system” or “Cy” as a component of formula I is carbocyclyl or heterocyclyl. The term “ring system” denotes one or more rings.
The term “bicyclic ring or ring system” denotes a ring system consisting of two or more common atom.
The term “aromatic” indicates that the Hueckel rule is satisfied and the term “non-aromatic” indicates that the Hueckel rule is not satisfied.
The terms “carbocycle” or “carbocyclic” or “carbocyclyl” include “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the 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 satisfied).
Non limiting examples of non-aromatic carbocyclic ring system are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl and the like.
Non limiting examples of aromatic carbocyclic ring system are phenyl, naphthyl and the like.
The term “aryl” as used herein is a group that contains any carbon-based aromatic group including, but not limited to phenyl, naphthalene, 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 “aralkyl” refers to aryl hydrocarbon radicals including an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-napthylhexyl. As used herein, the term “aralkenyl” refers to aryl hydrocarbon radicals including an alkenyl portion, as defined above, and an aryl portion, as defined above. Examples include styryl, 3-(benzyl) prop-2-enyl, and 6-napthylhex-2-enyl.
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.
The terms “heterocycle” or “heterocyclic” includes “aromatic heterocycle” or “heteroaryl ring system” and “nonaromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.
The terms “non-aromatic heterocycle” or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-membered, saturated 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, oxetanyl, azetidinyl, thietanyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-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, pyrrolinyl, 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-1-yl,
2.3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,
3.4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl,
4.5-dihydropyrazol-1-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, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2, 3, 4, 5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or-7-yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2- or -3- or -4-or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2, 3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
The term “heteroaryl” means 5 or 6-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) furyl, thienyl, pyrrol yl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; 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-1,3-diene-1,4-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-triazolyl, 1-imidazolyl, 1,2,3-triazolyl and 1,3,4-triazolyl.
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, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-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-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran- 6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1- benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3- benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-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-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.
Non-limiting examples of fused 6-5-membered heteroaryl include Indolizinyl; pyrazolo[1,5-ajpyridinyl; imidazo[1,2-a]pyridinyl; pyrrolo[1,2-a]pyrimidinyl; pyrazolo[1,5-a]pyrimidinyl; imidazo[1,2-a]pyrimidinyl; pyrrolo[1,2-a]pyrazinyl; pyrazolo[1,5-a]pyrazinyl; imidazo[1,2-a]pyrazinyl and the like.
This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl 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. The term“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. The term“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. The term “Trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen. Non limiting 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 haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.
Non limiting 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 where i and j are numbers from 1 to 21. For example, C1-C3 alkoxy designates methoxy through propoxy. In the above recitations, when a compound of formula (I) 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 indicates a range, e. g. (R)i-j, then the number of substituents may be selected from the integers between i and j inclusive.
When a group contains a substituent which can be hydrogen, for example R1 or R2, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Accordingly, the present invention provides a compound of general formula (I);
wherein;
A represent O, NR4 or S;
n, m and k represent integers, wherein n=0-2, m=0-1 and k=0-2;
R is selected from the group consisting of hydrogen, halogen and C1-C3-alkyl;
R1 is selected from the group consisting of R1a, SCN, SF5, NO2, C1-C8-alkyl-S(O)0-2R4, C1-C6-alkyl- OR4, C1-C8-alkyl-(C=O)-R4, C(R4a)=NR4, S(O)0-2C5-C12-aryl, S(O)0-2C7-C19-aralkyl, C3-C10- halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C1-C8-alkyloxy-C3-C10-cycloalkyl, C1-C8- alkylthio-C3-C10-cycloalkyl, C6-C10-aryl, C7-C19-aralkyl, C5-C12-bicycloalkyl and C7-C12- bicycloalkenyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
wherein R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O)O-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12- haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CO (R4a)2;
R2 represent following fragment G
wherein R5 is selected from the group consisting of hydrogen, X, CN, C1-C12-alkyl, C2-C12- alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10- cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C4-C10- halocycloalkylalkyl, C6-C10-aryl and C7-C19-aralkyl; R5 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R6 is selected from the group consisting of hydrogen, OR4, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0- 2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, S(O)0-2C5-C19-aryl, S(O)0-2C7-C19-aralkyl, C1-C 12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12- haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl C4-C10-cycloalkenyl, C5-C10- cycloalkynyl, C3-C10-cycloalkyloxy, C3-C10-cycloalkylthio, C6-C10-aryl, C7-C19-aralkyl, C5- C12-bicycloalkyl, C7-C12-bicycloalkenyl and C3-C10-heterocyclyl; or
R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2, may form a four to seven membered ring, which for its part may be substituted by one or more R7;
R7 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R4, OR4, NO2, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl,
C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C6-C10- aryl, C7-C19-aralkyl and C3-C10-heterocyclyl; each of R6 and R7 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C4-C10-cycloalkenyl and C5-C10-cycloalkynyl; R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C12-cycloalkenyl, C5-C12-cycloalkynyl, C6-C10-aryl, C7-C19-aralkyl and C3-C12-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; wherein; when m=1 then R2 may or may not be present;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
In a preferred embodiment, the compound of formula (I) is represented by formula Ia;
wherein;
A represent O or S;
n and m represent integers wherein n=0-2 and m=0-1;
R1a is selected from the group consisting of hydrogen, X, CN, OR4, N(R4)2, (C=O)-R4, S(O)0-2R4, C(R4a)=NR4, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl and C7-C19-aralkyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C 12-alkenyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C3-C10-cycloalkyl and C4-C10-cycloalkylalkyl;
R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C12-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C12-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl;
R5 is selected from the group consisting of hydrogen, X, CN, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkylalkyl, C6-C10-aryl and C7-C19-aralkyl; R5 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R6 is selected from the group consisting of hydrogen, OR4, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, S(O)0-2C5-C19-aryl, S(O)0-2C7-C19-aralkyl, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl C4-C10-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl, C5-C12-bicycloalkyl, C7-C12-bicycloalkenyl and C3-C10-heterocyclyl; or
R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2, may form a four to seven membered ring, which for its part may be substituted by one or more R7;
R7 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R4, OR4, NO2, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8- alkyl-(C=O)-R4, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C 10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C6-C10- aryl, C7-C19-aralkyl and C3-C10-heterocyclyl; R6 and R7 are may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
In another preferred embodiment, the compound of formula (I) is represented by formula Ib;
wherein
A represent O, NR4 or S;
n, m and k represent integers wherein n=0-1, m=1 and k=0-2;
R1 is selected from the group consisting of R1a, SCN, SF5, NO2, C1-C8-alkyl-S(O)0-2R4, C1-C6-alkyl-OR4, C1-C8-alkyl-(C=O)-R4, C(R4a)=NR4, S(O)0-2C5-C12-aryl, S(O)0-2C7-C19-aralkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C1-C8-alkyloxy-C3-C10-cycloalkyl, C1-C8-alkylthio-C3-C10-cycloalkyl, C6-C10-aryl, C7-C19-aralkyl, C5-C 12-bicycloalkyl and C7-C12-bicycloalkenyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C 12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl and C4-C10-cycloalkenyl; R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen; OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C6-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
In yet another preferred embodiment, the compound of formula (I) is represented by formula Ic;
wherein;
A represent O, NR4 or S;
n represents integers of 0-2;
R1 is selected from the group consisting of CN, C2-C12-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C1-C6-haloalkyloxy, C1-C6-haloalkylthio, C1-C6-haloalkylamino, C1-C6-dihaloalkylamino, C1-C6-haloalkyloxy-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C1-C6-dihaloalkylamino-C1-C6-alkyl and C1-C6-haloalkylthio-C1-C6-alkyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a )3, COOR4a, CN and CON(R4a)2;
R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl and C4-C10-cycloalkenyl; R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C6-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
In more preferred embodiment, the compound of formula (I) is selected from (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en- 1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((((2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methylene)amino)oxy)acetonitrile, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5 -carbaldehyde O-ethyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5 -carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclohexyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclohexyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1- yl)sulfonyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, N-((5-((Z)- (methoxyimino)methyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ4 -sulfaneylidene)cyanamide, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole- 5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, N-((E)-(4-((E)-(methoxyimino)methyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-14-sulfaneylidene)cyanamide, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopropyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-isopentyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-isopentyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-
yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-l-yl)sulfinyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en- l-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, N-((5-chlorolhiazol-2-yl)(3,4,4-trifluorobut-3-en-1 -yl)-λ4-sulfaneylidene)cyanamide, N-(thiazol-2-yl(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((5-chlorothiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, N- (oxo(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ6-sulfaneylidene)cyanamide, N-((5-bromothiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, imino(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (ethylimino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, 2,2,2-trifluoro-N-(oxo(thiazol-2-yl)(3,4,4-trifluorobut-3-en- 1-yl)- λ6-sulfaneylidene)acetamide, (5-chlorothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-chlorothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (methylimino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (propylimino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1 -yl)- λ6-sulfanone, ((cyclopropylmethyl)imino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-bromothiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfancylidene)cyanamide, (5-bromothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-(difluoromethyl)thiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, 2-(3,4,4-trifluorobut-3-en-1-ylsulfonimidoyl)thiazole-5-carbonitrile, (5-bromothiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1 -yl)- λ6-sulfanone, (5-chlorothiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-(difluoromethyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ4-sulfaneylidene)cyanamide, N-((4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((4-methylthiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, N-((5-chloro-4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ4-sulfaneylidene)cyanamide, N-((5-chloro-4-methylthiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, (5-chloro-4-methylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4-(tert-butyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfancylidene)cyanamide, (4-(tert-butyl)thiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)thiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, imino(4-phenylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1- yl)- λ6-sulfanone, (5-bromo-4-phenylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-chloro-4-phenylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4-(tert-butyl)-5-chlorothiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (4-(tert-butyl)-5-chlorothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)-5-chlorothiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)-5-chlorothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-bromo-4-(tert-butyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (5-bromo-4-(tert-butyl)thiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromo-4-(tert-butyl)thiazol-2-
yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromo-4-(tert-butyl)thiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4,5-dimethylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, imino(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (methylimino)(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (ethylimino)(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ6-sulfanone, (5-bromo-4-phenylthiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4,5-dimethylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4 -sulfaneylidene)cyanamide, 5-(2-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-4,5-dihydroisoxazole, 5-phenyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-4,5-dihydroisoxazole, 5-(2-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-4,5-dihydroisoxazole, 5-(2-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-4,5-dihydroisoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-phenyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-4,5-dihydroisoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)isoxazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole,
3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)isoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)-1,2,4-oxadiazole, N-((4-(5-methyl-1,2,4-oxadiazol-3-yl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((3,4,4-trifluorobut-3-en-1-yl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiazol-2-yl)-λ4-sulfaneylidene)cyanamide, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)- 4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-methyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-5-((2-phenylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, (E)-5-((2-methylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-benzyl oxime, (E)-5-((2-phenylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-benzyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-benzyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, 2-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, 3-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)butan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, 5-(thiophen-2-yl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclobutyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-(thiophen-2-yl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclopropyl-3-(2- ((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isobutyl oxime, (E)-2-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)propan-1-one O-methyl oxime, 3-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)butan-1-one O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, 5-cyclopropyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclobutyl-3-(2-((3,4,4- trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 4-cyclopropyl-2-((3, 4, 4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, 4-cyclopropyl-2-((3, 4, 4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, 5-cycloprop yl-3-(2-((3, 4, 4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, 5-cyclobutyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, 2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-(3,4-difluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(3,4-difluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5- (2-chloro-6-fluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 5-(2-bromo-6-fluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, 4-(methylamino)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbonitrile, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl- 2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut- 3-en-1-yl)thio)oxazole, 4-(tert-butyl)-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole,
4-(tert-butyl)-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole, 4-methyl-2- ((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbonitrile, 4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole, 4-cycloprop yl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-cyclopropyl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-cyclopropyl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbonitrile, (E)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-ethyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-l-yl)thio)-1H-imidazole-5-carbaldehyde O-ethyl oxime, (E)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-
yl)thio)-1H-imidazole-5-carbaldehyde O-methyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-methyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)-1H-imidazole-5-carbaldehyde O-methyl oxime, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde and (4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanol.
It can be advantageous to isolate or synthesize in each case the biologically more effective isomer, for example enantiomer or diastereomer, or isomeric mixture, for example enantiomeric mixture or diastereomeric mixture, if the individual components have a different biological activity.
The compounds of formula (I) and wherever appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
In one embodiment, the present invention provides use of compound of general formula (I), stereoisomers, agriculturally acceptable salts, tuatomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites.
In preferred embodiment, the present invention provides use of compound of general formula (I), stereoisomers, agriculturally acceptable salts, tuatomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against nematodes and phytopathogenic fungi.
The agricultural crops are selected from cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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, other vegetables or ornamentals.
CLAIMS
1. A compound of general formula (I);
wherein;
A represent O, NR4 or S;
n, m and k represent integers, wherein n=0-2, m=0-1 and k=0-2;
R is selected from the group consisting of hydrogen, halogen and C1-C3-alkyl;
R1 is selected from the group consisting of R1a, SCN, SF5, NO2, C1-C8-alkyl-S(O)0-2R4, C1-C6-alkyl- OR4, C1-C8-alkyl-(C=O)-R4, C(R4a)=NR4, S(O)0-2C5-C12-aryl, S(O)0-2C7-C19-aralkyl, C3-C10- halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C1-C8-alkyloxy-C3-C10-cycloalkyl, C1-C8- alkylthio-C3-C10-cycloalkyl, C6-C10-aryl, C7-C19-aralkyl, C5-C12-bicycloalkyl and C7-C12- bicycloalkenyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
wherein R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O)O-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2- C12-haloalkenyl, C2-C12-haloalkynyl and C3-C10-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R2 represent following fragment G
R5 is selected from the group consisting of hydrogen, X, CN, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl,C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C4-C10-halocycloalkylalkyl, C6-C10-aryl and C7-C19-aralkyl; R5 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R6 is selected from the group consisting of hydrogen, OR4, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0- 2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8alkyl-(C=O))-R4, S(O)0-2C5-C19-aryl, S(O)0-2C7-C19-aralkyl, C1-C 12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12- haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl C4-C10-cycloalkenyl, C5-C10- cycloalkynyl, C3-C10-cycloalkyloxy, C3-C10-cycloalkylthio, C6-C10-aryl, C7-C19-aralkyl, C5- C12-bicycloalkyl, C7-C12-bicycloalkenyl and C3-C10-heterocyclyl; or
R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2, may form a four to seven membered ring, which for its part may be substituted by one or more R7;
R7 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R4, OR4, NO2, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C6-C10- aryl, C7-C19-aralkyl and C3-C10-heterocyclyl; R6 and R7 are may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C4-C10-cycloalkenyl and C1-C10-cycloalkynyl ; R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C12-cycloalkenyl, C5-C12-cycloalkynyl, C6-C10-aryl, C7-C19-aralkyl and C3-C12-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; when m= 1 then R2 may or may not be present;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
2. The compound as claimed in claim 1, wherein said compound of formula (I) is represented by formula Ia;
wherein;
A represent O or S;
n and m represent integers wherein n=0-2 and m=0-1;
R1a is selected from the group consisting of hydrogen, X, CN, OR4, N(R4)2, (C=O)-R4, S(O)0-2R4, C(R4a)=NR4, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl and C7-C19-aralkyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C 12-alkenyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C3-C10-cycloalkyl and C4-C10-cycloalkylalkyl;
R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C12-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C12-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl;
R5 is selected from the group consisting of hydrogen, X, CN, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkylalkyl, C6-C10-aryl and C7-C19-aralkyl; R5 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R6 is selected from the group consisting of hydrogen, OR4, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, S(O)0-2C5-C19-aryl, S(O)0-2C7-C19-aralkyl, C1-C12-alkyl, C2-C 12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl C4-C10-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl, C5-C12-bicycloalkyl, C7-C12-bicycloalkenyl and C3-C10-heterocyclyl; or
R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2, may form a four to seven membered ring, which for its part may be substituted by one or more R7;
R7 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R4, OR4, NO2, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C8-alkyl-(C=O)-R4, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C6-C10- aryl, C7-C19-aralkyl and C3-C10-heterocyclyl; R6 and R7 are may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
X represents halogen;
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
3. The compound as claimed in claim 1, wherein said compound of formula I is represented by formula Ib;
wherein;
A represent O, NR4 or S;
n, m and k represent integers wherein n=0-1, m=1 and k=0-2;
R1 is selected from the group consisting of R1a, SCN, SF5, NO2, C1-C8-alkyl-S(O)0-2R4, C1-C6-alkyl-OR4, C1-C3-alkyl-(C=O)-R4, C(R4a)=NR4, S(O)0-2C5-C12-aryl, S(O)0-2C7-C19-aralkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C5-C10-cycloalkynyl, C1-C8-alkyloxy-C3-C10-cycloalkyl, C1-C8-alkylthio-C3-C10-cycloalkyl, C6-C10-aryl, C7-C19-aralkyl, C5-C12-bicycloalkyl and C7-C12-bicycloalkenyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
X represents halogen;
R3 is selected from the group consisting of hydrogen, CN, (C=O)-R4, OR4, N(R4)2, S(O)0-2R4, Si(R4)3, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl and C4-C10-cycloalkenyl; R3 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, OR4a, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C6-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
4. The compound as claimed in claim 1, wherein said compound of formula I is represented by formula Ic;
wherein;
A represent O, NR4 or S;
n represents integers of 0-2;
R1 is selected from the group consisting of CN, C2-C12-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C1-C6-haloalkyloxy, C1-C6-haloalkylthio, C1-C6-haloalkylamino, C1-C6-dihaloalkylamino, C1-C6-haloalkyloxy-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C1-C6-dihaloalkylamino-C1-C6-alkyl and C1-C6-haloalkylthio-C1-C6-alkyl; wherein one or more carbon atoms of the cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
R1a is selected from the group consisting of hydrogen, X, CN, (C=O)-R4, OR4, N(R4)2, S(O) )0-2R4, Si(R4)3, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1a may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2;
X represents halogen;
R4 is selected from the group consisting of hydrogen; N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C6-C10-aryl, C7-C19-aralkyl and C3-C6-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof.
5. The compound as claimed in claim 1, wherein said compound of formula (I) is selected from (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en- 1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((((2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methylene)amino)oxy)acetonitrile, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-ethyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-phenyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-
yl)sulfonyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclohexyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclohexyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopentyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-methyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-4-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-
yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, N-((5-((Z)- (methoxyimino)methyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ4 -sulfaneylidene)cyanamide, (E)- 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole- 5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, N-((E)-(4-((E)-(methoxyimino)methyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-14-sulfaneylidene)cyanamide, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-methyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-ethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isopropyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-cyclopropylmethyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanone O-isopentyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en- 1-yl)sulfinyl)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-propyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)methanone O-isopentyl oxime, (E)-phenyl(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)methanone O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-cyclopropylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en- 1-yl)thio)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl) thio) thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (E)- 1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopropyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (Z)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazol-5-yl)ethan-1-one O-methyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)ethan-1-one O-ethyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)ethan-1-one O-ethyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (Z)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)ethan-1-one O-isopentyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-
yl)thio)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-1-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)ethan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en- 1-yl)sulfinyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut- 3-en-1-yl)sulfonyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-4-(trifluoromethyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, N-((5-chlorothiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-(thiazol-2-yl(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((5-chlorothiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, N- (oxo(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ6-sulfaneylidene)cyanamide, N-((5-bromothiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, imino(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (ethylimino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, 2,2,2-trifluoro-N-(oxo(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)acetamide, (5-chlorothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-chlorothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (methylimino)(thiazol- 2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (propylimino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en- 1 -yl)- λ6-sulfanone, ((cyclopropylmethyl)imino)(thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-bromothiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (5-bromothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-(difluoromethyl)thiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, 2-(3,4,4-trifluorobut-3-en-1-ylsulfonimidoyl)thiazole-5-carbonitrile, (5-bromothiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-chlorothiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-(difluoromethyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ4-sulfaneylidene)cyanamide, N-((4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((4-methylthiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)-λ6-sulfaneylidene)cyanamide, N-((5-chloro-4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((5-chloro-4-methylthiazol-2-yl)(oxo)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfaneylidene)cyanamide, (5-chloro-4-methylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4-(tert-butyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (4-(tert-butyl)thiazol-2-
yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)thiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, imino(4-phenylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromo-4-phenylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-chloro-4-phenylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4-(tert-butyl)-5-chlorothiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (4-(tert-butyl)-5-chlorothiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)-5-chlorothiazol- 2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4-(tert-butyl)-5-chlorothiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((5-bromo-4-(tert-butyl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, (5-bromo-4-(tert-butyl)thiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromo-4-(tert-butyl)thiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (5-bromo-4-(tert-butyl)thiazol-2-yl)(ethylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (4,5-dimethylthiazol-2-yl)(imino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, imino(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (methylimino)(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, (ethylimino)(4-methylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ6-sulfanone, (5-bromo-4-phenylthiazol-2-yl)(methylimino)(3,4,4-trifluorobut-3-en-1-yl)- λ6-sulfanone, N-((4,5-dimethylthiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4 -sulfaneylidene)cyanamide, 5-(2-chlorophenyl)- 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-4,5-dihydroisoxazole, 5-phenyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-4,5-dihydroisoxazole, 5-(2-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-4,5-dihydroisoxazole, 5-(2-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-4,5-dihydroisoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-phenyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-4,5-dihydroisoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)isoxazole, 5-methyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 5-(2H-tetrazol-5-yl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole,
3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazol-5(4H)-one, 5-(4-chlorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)isoxazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-methyl-3-(2-((3,4,4- trifluorobut-3-en-1-yl)thio)thiazol-4-yl)-1,2,4-oxadiazole, N-((4-(5-methyl-1,2,4-oxadiazol-3-yl)thiazol-2-yl)(3,4,4-trifluorobut-3-en-1-yl)-λ4-sulfaneylidene)cyanamide, N-((3,4,4-trifluorobut-3-en-1-yl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)thiazol-2-yl)-λ4-sulfaneylidene)cyanamide, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-ethyl oxime, (E)-5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-4-carbaldehyde O-methyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-5-((2-phenylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, (E)-5-((2-methylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-benzyl oxime, (E)-5-((2-phenylhydrazineylidene)methyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-benzyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-benzyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, (E)-1-(4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)ethan-1-one O-ethyl oxime, (E)-4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, 2-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)propan-1-one O-methyl oxime, 3-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazol-5-yl)butan-1-one O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-cyclopropylmethyl oxime, 5-
(thiophen-2-yl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclobutyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-(thiophen-2-yl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclopropyl-3-(2- ((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-isobutyl oxime, (E)-2-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)propan-1-one O-methyl oxime, 3-methyl-1-(4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazol-5-yl)butan-1-one O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, 5-cyclopropyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-cyclobutyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-ethyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, 5-cyclopropyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-ethyl oxime, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-methyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-ethyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-isopropyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-isopropyl oxime, 5-cyclobutyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, 2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-ethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbaldehyde O-methyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (Z)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-
yl)sulfonyl)thiazole-5-carbaldehyde O-cyclopropylmethyl oxime, (E)-2-((4,4-difluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-cyclobutylmethyl oxime, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-ethyl-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, 5-(3,4-difluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)-1,2,4-oxadiazole, (E)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbaldehyde O-cyclobutylmethyl oxime, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(tert-butyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(3,4-difluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazol-5-yl)-1,2,4-oxadiazole, 5-(2-chloro-6-fluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 5-(2-bromo-6-fluorophenyl)-3-(2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)isoxazole, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbaldehyde O-methyl oxime, (E)-4-(methoxymethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbaldehyde O-methyl oxime, 4-(methylamino)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde O-methyl oxime, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole, 2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbonitrile, 5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl- 2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut- 3-en-1-yl)thio)oxazole, 4-(tert-butyl)-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole,
4-(tert-butyl)-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole, 4-methyl-2- ((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)oxazole-5-carbonitrile, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-methoxy-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)oxazole-5-carbonitrile, 4-(tert-butyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbonitrile, 5-(difluoromethyl)-4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole, 4-cyclopropyl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-cyclopropyl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-cyclopropyl-5-(difluoromethyl)-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole-5-carbonitrile, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbonitrile, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)thiazole, 4-cyclopropyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole, 4-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)oxazole-5-carbonitrile, (E)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-ethyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-ethyl oxime, (E)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-methyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)thio)-1H-imidazole-5-carbaldehyde O-methyl oxime, (Z)-1-methyl-2-((3,4,4-trifluorobut-3-en-1-yl)sulfinyl)-1H-imidazole-5-carbaldehyde O-methyl oxime, 4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazole-5-carbaldehyde and (4-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)thio)thiazol-5-yl)methanol.
6. A process for preparing a compound of formula (I) and/or a salt thereof as claimed in claim 1, wherein said process comprises at least one of the following steps (a) to (p):
a) converting substituted thioether compound of formula (4) to afford compound of formula (2) followed by alkylating or acylating the compound of formula (2) to afford compound of formula (1) according to reaction scheme as depicted below:
b) converting sulfoxide compound of formula (5) to sulfoximine compound of formula (2) followed by alkylating or acylating the compound of formula (2) to afford compound of formula (1) according to reaction scheme as depicted below:
c) reacting substituted thioether compound of formula (4) with cyanamide compound to afford compound of formula (3) followed by oxidizing the compound of formula (3) to afford compound of formula (1) according to reaction scheme as depicted below:
d) oxidizing substituted thioether of formula (4) to afford compound of formula (5) or (6) according to reaction scheme as depicted below:
e) reducing ester compound of formula (15) to alcohol compound of formula (16) followed by oxidizing the compound of formula (16) to afford corresponding aldehyde compound of formula (4a or 4b) according to reaction scheme as depicted below:
f) formylating thio compound of formula (18) to afford aldehyde compound of formula (4b) according to reaction scheme as depicted below:
g) converting halide compound of formula (21) to thio compound of formula (22) followed by alkylation with compound of formula (14) to afford compound of formula (4a or 4b) according to reaction scheme as depicted below:
h) reacting aldehyde compound of formula (4a or 4b) with Grignard reagent to afford compound of formula (9) followed by oxidizing the compound of formula (9) to afford corresponding ketone compound of formula (10) according to reaction scheme as depicted below:
i) reacting aldehyde compound of formula (4a or 4b) with (un) substituted hydroxyl amine optionally followed by reaction with alkyl halide to afford compound of formula (8) which is then converted to compound of formula la following step (a) according to reaction scheme as depicted below:
j) reacting ketone compound of formula (10) with substituted hydroxyl amine to afford compound of formula (11) followed by reaction with alkyl halide to afford compound of formula (12) which is then converted to compound of formula la following step (a) according to reaction scheme as depicted below:
k) reacting substituted thioether compound of formula (18) with cyanamide compound to afford compound of formula (21) followed by oxidizing the compound of formula (21) to afford compound of formula (1a) according to reaction scheme as depicted below:
l) reacting compound of formula (4a or 4b) with suitable fluorinating agent to afford compound of formula (32) which is then converted to compound of formula (1b) following step (a) according to reaction scheme as depicted below:
m) reacting compound of formula (7) with substituted styrene of formula (23) to afford compound of formula (24) which is then converted to compound of formula (1a) following step (a) respectively according to reaction schemes as depicted below:
n) reacting compound of formula (7) with substituted alkyne of formula (25) to afford compound of formula (26) which is then converted to compound of formula (1a) following step (a) according to reaction scheme as depicted below:
o) reacting oxime compound of formula (7) with phosphonic anhydride compound and further reacting with hydroxyl amine to afford compound of formula (28) followed by reaction with acid chloride/acid anhydride (29 or 29a) to afford compound of formula (30) which is then converted to compound of formula (1a) using step (a) according to reaction schemes as depicted below:
p) reacting compound of formula (28) with carbonylating agent to afford compound of formula (31) followed by converting the compound of formula (31) to compound of formula (1a) following step (a) according to reaction schemes as depicted below:
7. A composition for controlling or preventing phytopathogenic microorganisms comprising a compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof as claimed in claim 1 and one or more inert carriers.
8. The composition as claimed in claim 7, wherein said composition may additionally comprises one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
9. The composition as claimed in claim 7 or 8, wherein the concentration of the compound of general formula (I) ranges from 1 to 90% 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.
10. A combination comprising the compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof as claimed in claim 1 and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and fertilizers.
11. Use of compound of general formula (I), stereoisomers, agriculturally acceptable salts, tuatomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10, for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes, mites.
12. The use of compound of general formula (I) as claimed in claim 11, for controlling or preventing agricultural crops and/or horticultural crops against nematodes and phytopathogenic fungi.
13. The use of the compounds of general formula (I) as claimed in claim 11 or 12, wherein said agricultural crops are selected from cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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, other vegetables and ornamentals.
14. A seed comprising compound of formula (I) and/or stereoisomers or agriculturally acceptable salts or tuatomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or
10, wherein the amount of the compound of the formula (I) or an N-oxide or an agriculturally acceptable salt thereof is ranging from 0.1 g to 10 kg per 100 kg of seed.
15. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tuatomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10, is applied to the plants, to parts thereof or a locus thereof.
16. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tuatomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10 is applied to the seeds of plants.
17. A method of controlling or preventing phytopathogenic microorganisms in agricultural crops and or horticultural crops using the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tuatomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10 comprises a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops.
18. A compound of general formula (II),
wherein;
A represent O, NR4 or S;
n, m, and k represents integers wherein n=0-2, m=0-1 and k=0-2;
R is selected from the group consisting of hydrogen, halogen and C1-C3-alkyl;
R1 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, OR4, NO2, N(R4)2, Si(R4)3, (C=O)-R4, S(O)0-2R4, C1-C8-alkyl-S(O)0-2R4, C1-C6-alkyl-OR4, C1-C8-alkyl-(C=O)-R4, C(R4a)=NR4, S(O)0-2C5-C12-aryl, S(O)0-2C7-C19-aralkyl, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C10-cycloalkenyl, C3-C10-cycloalkynyl, C1-C8-alkyloxy-C3-C10-cycloalkyl, C1-C8-alkylthio-C3-C10-cycloalkyl, C7-C19-aralkyl, C5-C12-bicycloalkyl and C7-C12-bicycloalkenyl; wherein the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R4)2; R1 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a )3, COOR4a, CN and CON(R4a)2;
R4 is selected from the group consisting of hydrogen, N(R4a)2, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C4-C12-cycloalkenyl, C5-C12-cycloalkynyl and C3-C12-heterocyclyl; R4 may be optionally substituted by one or more groups selected from the group consisting of X, R4a, OR4a, SR4a, N(R4a)2, Si(R4a)3, COOR4a, CN and CON(R4a)2,
R4a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl;
X represents halogen.
| # | Name | Date |
|---|---|---|
| 1 | 202017028350-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [03-07-2020(online)].pdf | 2020-07-03 |
| 2 | 202017028350-STATEMENT OF UNDERTAKING (FORM 3) [03-07-2020(online)].pdf | 2020-07-03 |
| 3 | 202017028350-PRIORITY DOCUMENTS [03-07-2020(online)].pdf | 2020-07-03 |
| 4 | 202017028350-FORM 1 [03-07-2020(online)].pdf | 2020-07-03 |
| 5 | 202017028350-DECLARATION OF INVENTORSHIP (FORM 5) [03-07-2020(online)].pdf | 2020-07-03 |
| 6 | 202017028350-COMPLETE SPECIFICATION [03-07-2020(online)].pdf | 2020-07-03 |
| 7 | 202017028350-FORM 3 [28-09-2020(online)].pdf | 2020-09-28 |
| 8 | 202017028350.pdf | 2021-10-19 |
| 9 | 202017028350-FORM 18 [07-12-2021(online)].pdf | 2021-12-07 |
| 10 | 202017028350-FER.pdf | 2021-12-23 |
| 11 | 202017028350-FORM-26 [04-01-2022(online)].pdf | 2022-01-04 |
| 12 | 202017028350-Proof of Right [23-06-2022(online)].pdf | 2022-06-23 |
| 13 | 202017028350-PETITION UNDER RULE 137 [23-06-2022(online)].pdf | 2022-06-23 |
| 14 | 202017028350-OTHERS [23-06-2022(online)].pdf | 2022-06-23 |
| 15 | 202017028350-Information under section 8(2) [23-06-2022(online)].pdf | 2022-06-23 |
| 16 | 202017028350-FORM 3 [23-06-2022(online)].pdf | 2022-06-23 |
| 17 | 202017028350-FER_SER_REPLY [23-06-2022(online)].pdf | 2022-06-23 |
| 18 | 202017028350-CORRESPONDENCE [23-06-2022(online)].pdf | 2022-06-23 |
| 19 | 202017028350-CLAIMS [23-06-2022(online)].pdf | 2022-06-23 |
| 20 | 202017028350-PatentCertificate07-02-2023.pdf | 2023-02-07 |
| 21 | 202017028350-IntimationOfGrant07-02-2023.pdf | 2023-02-07 |
| 22 | 202017028350-RELEVANT DOCUMENTS [27-09-2023(online)].pdf | 2023-09-27 |
| 1 | 202017028350patseersearchE_22-12-2021.pdf |