Abstract: The present invention relates to novel oxadiazoles of Formula (I),wherein, R1, L1, A, L2 and R10 are as defined in the detailed description. The oxadiazoles of Formula (I) are useful in controlling phytopathogenic fungi.
OXADIAZOLES FOR USE IN CONTROLLING PHYTOPATHOGENIC FUNGI FIELD OF THE The present invention relates to novel metal polymorphs or the agriculturally acceptable salts thereof and plurality of processes for preparing the the present invention relates to a combination and a composition comprising novel oxadiazoles of the present Still the present invention relates to a use of novel oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi and to a method for controlling or preventing phytopathogenic harmful Oxadiazoles have already been disclosed in the For example in WO2018187553 and WO2018202491 various oxadiazoles have be The oxadiazole compounds reported in the above literature have disadvantages in certain such as that they exhibit a narrow spectrum of application or they do not have satisfactory fungicidal particularly at low application it is an object of the present invention to provide having activity a broader activity spectrum against phytopathogenic This objective is achieved by the using oxadiazoles of the present invention for controlling or preventing phytopathogenic The present invention relates to novel oxadiazoles of Formula L2 and R10 are as defined in the detailed The compounds of formula I have now been found to be advantages over the compounds reported in the literature in either of improved fungicidal broader spectrum biological lower application biological or environmental or enhanced plant The present invention further relates to a combination comprising novel oxadizoles of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to control or The present invention still further relates to a composition comprising novel oxadizoles or novel oxadiazloes in combination with further pesticidally active The present invention still further relates to a method and use of novel combinations or compositions thereof for controlling and or preventing plant particularly phtopathogenic DETAILED DESCRIPTION OF THE The definitions provided herein for 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 As used the or any other variation are intended to cover a subject to any limitation explicitly For a 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 process or The transitional excludes any step or ingredient not If in the such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated When the appears in a clause of the body of a rather than immediately following the it limits only the element set forth in that other elements are not excluded from the claim as a The transitional essentially is used to define a composition or method that includes components or in addition to those literally provided that these additional components or elements do not materially affect the basic and novel of the claimed The essentially occupies a middle ground unless expressly stated to the refers to an and not to an exclusive For a condition B is satisfied by any one of the A is true and B is false not A is false not and B is true and both A and B are true the indefinite preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances of the element or should be read to include one or at least and the singular word form of the element or component also includes the plural unless the number is obviously meant to be As referred to in this the includes gastropods and nematodes of economic importance as The includes pill bugs and The includes slugs and other The refers to a living organism of the Phylum The includes phytophagous nematodes flukes acanthocephala and tapeworms In the context of this pest means inhibition of invertebrate pest development feeding mating and related expressions are defined The refers to the production of field crops such as for food and fiber and includes the growth of soybeans and other cereal leafy vegetables and other cole fruiting vegetables crucifers and sweet tree fruits stone and small fruit and other specialty crops The refers to other than field such as horticultural crops nursery or ornamental plants not grown in a commercial and industrial turf sod golf sports wood stored and vegetation public health and animal health domesticated animals such as livestock and undomesticated animals such as Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective biologically amount of a compound of the present typically in the form of a composition formulated for veterinary to the animal to be As referred to in the present disclosure and the and refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic Such effects on the pest include retarded diminished mobility or lessened ability to remain on or in the host reduced feeding and inhibition of These effects on invertebrate parasite pests provide control reduction or of parasitic infestation or infection of the 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 The various stereoisomers include chiral optical and geometric Any desired mixtures of these isomers fall within the scope of the claims of the present One skilled in the art will appreciate that one stereoisomer may be more active may exhibit beneficial effects when enriched relative to the other or when separated from the other the person skilled in the art knows processes or methods or technology to to selectively prepare said The meaning of various terms used in the description shall now be The used either alone or in compound words such or or alkylcarbonylalkyl or alkylsuphonylamino includes or branched C1 to C24 preferably C1 to C15 more preferably C1 to C10 most preferably C1 to C6 Non limiting examples of alkyl include and or the different If the alkyl is at the end of a composite for in the part of the composite substituent at the for example the may be or polysubstituted identically or differently and independently by The same also applies to composite substituents in which other for example carbonyloxy and the are at the The used either alone or in compound words includes or branched C2 to C24 preferably C2 to C15 more preferably C2 to C10 most preferably C2 to C6 Non limiting examples of alkenes include and and the different also includes polyenes such as and This definition also applies to alkenyl as a part of a composite for example haloalkenyl and the unless defined specifically Non limiting examples of alkynes include and and the different This definition also applies to alkynyl as a part of a composite for example haloalkynyl unless specifically defined The can also include moieties comprised of multiple triple bonds such as The means alkyl closed to form a Non limiting examples include cyclopentyl and This definition also applies to cycloalkyl as a part of a composite for example cycloalkylalkyl unless specifically defined The means alkenyl closed to form a ring including partially unsaturated hydrocarbyl Non limiting examples include cyclopentenyl and This definition also applies to cycloalkenyl as a part of a composite for example cycloalkenylalkyl unless specifically defined The means alkynyl closed to form a ring including partially unsaturated Non limiting examples include cyclopentynyl and This definition also applies to cycloalkynyl as a part of a composite for example cycloalkynylalkyl unless specifically defined The and the like are defined Non limiting examples of cycloalkoxy include cyclopentyloxy and This definition also applies to cycloalkoxy as a part of a composite for example cycloalkoxy alkyl unless specifically defined The either alone or in compound words such includes bromine or when used in compound words such said alkyl may be partially or fully substituted with halogen atoms which may be the same or limiting Examples of include and This definition also applies to haloalkyl as a part of a composite for example haloalkylaminoalkyl unless specifically defined The are defined analogously except instead of alkyl alkenyl and alkynyl groups are present as a part of the The means or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified examples of haloalkoxy include pentafluoroethoxy and This definition also applies to haloalkoxy as a part of a composite for example haloalkoxyalkyl unless specifically defined The means or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified examples of haloalkylthio include pentafluoroethylthio and This definition also applies to haloalkylthio as a part of a composite for example haloalkylthioalkyl unless specifically defined Non limiting examples of include and Examples of include and The Amino wherein R can be H or any possible substituent such as Carbonyl means carbonyloxy means sulfinyl means sulfonyl means The used either alone or in compound words included C1 to C24 preferably C1 to C15 more preferably C1 to C10 most preferably C1 to C6 Examples of alkoxy include and methylpropoxy and the different This definition also applies to alkoxy as a part of a composite for example unless specifically defined The denotes alkoxy substitution on Examples of include CH3CH2CH2CH2OCH2 and The denotes alkoxy substitution on The includes branched or alkylthio moieties such as and and the different The terms and the are defined analogously to the above The denotes alkylthio substitution on Non limiting examples of include CH3CH2CH2CH2SCH2 and denotes alkylthio substitution on The term denotes cycloalkyl substitution on alkyl The terms cycloalkylaminocarbonyl and the are defined analogously to or The is an alkoxy group bonded to a skeleton via a carbonyl group This definition also applies to alkoxycarbonyl as a part of a composite for example cycloalkylalkoxycarbonyl and the unless specifically defined The term denotes alkoxy carbonyl substitution on alkyl denotes alkyl carbonyl substitution on alkyl The terms cycloalkylalkylaminoalkyl and the like are defined Non limiting examples include and and the different The includes wherein Ar can be any carbocyle or This definition also applies to alkylsulphinyl as a part of a composite for example haloalkylsulphinyl unless specifically defined Non limiting examples include and and the different The includes wherein Ar can be any carbocyle or This definition also applies to alkylsulphonyl as a part of a composite for example alkylsulphonylalkyl unless defined The and the are defined analogously to the above The carbocyclic ring carbocylic ring or polycyclic or bicyclic ring compounds in which ring may be aromatic or aromatic indicates that the Huckel rule is satisfied and aromatic indicates that the Huckel rule is not The 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 oxygen and provided that each ring contains no more than 4 no more than 2 oxygens and no more than 2 The means 5 or fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of nitrogen and if the ring contains more than one oxygen they are not directly heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen heteroaryl groups in addition to carbon may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring for example not limited heteroaryl containing one to four nitrogen or benzofused heteroaryl containing one to three nitrogen heteroaryl groups in addition to carbon 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 group in which one or two carbon atoms may be replaced by nitrogen where these rings are attached to the skeleton via one of the nitrogen ring for example not limited and heteroaryl which contains one to four nitrogen heteroaryl groups in addition to carbon may one to three and one to four nitrogen atoms as ring for example not limited and benzofused heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur for example not limited and benzofused heteroaryl which contains one to three nitrogen for example not limited and This definition also applies to heteroaryl as a part of a composite for example heteroarylalkyl unless specifically defined The indicates that the Huckel rule is satisfied and the indicates that the Huckel rule is not The ring heterocycle ring or polycyclic or bicyclic ring compounds in which ring may be aromatic or wherein the heterocycle ring contains at least one heteroatom selected from and or C ring member of the heterocycle may be replaced by and indicates The means to preferably to saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of nitrogen and or tricyclic heterocycles which in addition to carbon ring one to three nitrogen atoms one oxygen or sulphur atom or one or two oxygen sulphur if the ring contains more than one oxygen they are not directly for example not limited or or or or or or or or or or or or or or or or or or or or or or or or and hexahydrooxepinyl such as or or or or or or or or or or or or or or or or or or and and and and and and This definition also applies to heterocyclyl as a part of a composite for example heterocyclylalkyl unless specifically defined The includes 3 branched alkyl radicals attached to and linked through a silicon atom such as triethylsilyl and The term denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or The denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or The denotes a trialkylsilyl moiety attached through Non limiting examples include and Examples of include and the different butoxy pentoxycarbonyl Examples of include and the different butylamino pentylaminocarbonyl Non limiting examples of include and Examples of include and Non limiting examples of include and The term alkoxycarbonylalkyl amino and the like are defined analogously Non limiting examples of include and The means wherein and indicates substituents and A and B indicate any The means wherein and indicates substituents and A and B indicate any The total number of carbon atoms in a substituent group is indicated by prefix where i and j are numbers from 1 to For alkylsulfonyl designates methylsulfonyl through C2 alkoxyalkyl designates C3 alkoxyalkyl for CH3OCH2CH2 or and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon examples including CH3CH2CH2OCH2 and In the above when a compound of Formula I is comprised of one or more heterocyclic all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed said substituents they exceed are independently selected from the group of defined when the subscript m in indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 When a group contains a substituent which can be when this substituent is taken as it is recognized that said group is being The embodiments herein and the various features and advantageous details thereof are explained with reference to the embodiments in the Descriptions of components and processing techniques are omitted so as to not unnecessarily obscure the embodiments The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments the examples should not be construed as limiting the scope of the embodiments The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others by applying current readily modify adapt for various applications such specific embodiments without departing from the generic such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of while the embodiments herein have been described in terms of preferred those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described Any discussion of articles and the like that has been included in this specification is solely for the purpose of providing a context for the It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this The numerical values mentioned in the description and the though might form a critical part of the present invention of the present any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present inventive compounds of the present invention if be present as mixtures of different possible isomeric especially of for example E and threo and and also optical but if appropriate also of Both the E and the Z and also the threo and erythro and the optical any desired mixtures of these isomers and the possible tautomeric forms are disclosed and The for the purpose of the present disclosure includes but is not limited to stramenopiles insects and The is understood here to mean all plants and plant such as desired and undesired wild plants or crop plants naturally occurring crop Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these including the transgenic plants and including the plant cultivars which are protectable and by plant For the purpose of the present disclosure the includes a living organism of the kind exemplified by and typically growing in a absorbing water and required substances through its and synthesizing nutrients in its leaves by Examples for the purpose of the present invention include but are not limited to agricultural crops such as oats or sugar beet or fodder fruits and fruit such as stone fruits or soft blackberries or leguminous such as alfalfa or oil such as cocoa castor oil oil ground nuts or such as cucumber or fiber such as hemp or citrus fruit and citrus such as grapefruits or any horticultural such as cucurbits or lauraceous such as cinnamon or oleaginous energy and raw material such as other leguminous sugar cane or oil vines grapes and grape juice grape sweet leaf called natural rubber plants or ornamental and forestry such as trees or and on the plant propagation such as and the crop material of these the plant for the purpose of the present invention include but is not limited to soybean and other leguminous fruits and fruit nuts and nut citrus and citrus any horticultural oleaginous sugar sugar peppers and any floricultural plants and other plants for use of human and The is understood to mean all parts and organs of plants above and below the For the purpose of the present disclosure the term plant parts includes but is not limited to roots including lateral root root root fruit auxillary nodes and The includes surroundings of plant or plant parts and equipment or tools used during or after a plant or a plant Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to injecting and The means adhered to a plant or plant part either physically or chemically including novel oxadizole compounds of the present invention are represent by Formula metal polymorphs or the agriculturally acceptable salts Formula I R1 is L1 is a direct an at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A is an aromatic or carbocyclic wherein the ring members of the carbocyclic ring are selected from and or A is an aromatic or heterocyclic wherein the heteroatom of the aromatic heterocyclic ring is selected from O and wherein heteroatom of the heterocyclic ring is selected from and and one or more C atoms of the aromatic heterocyclic ring may be optionally replaced by and and A is unsubstituted or is substituted with one or more identical or different RA RA is selected from the group consisting of or to membered spirocyclic and to membered carbocyclic or heterocyclic RA may be optionally substituted with one or more identical or different Ra selected from or to membered spirocyclic to membered carbocyclic or heterocyclic ring may be optionally substituted with one or more identical or different substituents selected from or or two RA together with the atoms to which they are attached may form a to membered aromatic or carbocyclic ring or ring or aromatic or heterocyclic ring or ring system which may be optionally substituted with one or more identical or different the C atom of the carbocyclic ring may be optionally replaced by and the heteroatom of the aromatic heterocyclic ring is selected from O and wherein heteroatom of the heterocyclic ring is selected from and and one or more C atoms of the heterocyclic ring may be optionally replaced by and and R6c are independently selected from the group of or Rb and Rc represent or Rd represents or and Re represents or L2 is a fragment selected from the group 0 k is an integer ranging from 0 to an on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to in Formula I when R1 is A is phenyl ring or carbocyclic ring or to membered heterocyclic L2 is L2c and 0 then R10 is not in Formula I when R1 is A is phenyl ring or to membered heteroaromatic ring L2 is L2d and 0 to 4 then R10 is not R11 and R11 is optionally substituted with a group selected from and phenyl ring optionally substituted with and R7 and R8 are independently selected from or or R2 and R2a and R2b and R2c and R2d and R2e and and or R7 and R8 together with the atoms to which they are attached may form to membered carbocylic ring or heterocyclic ring which may be optionally substituted with or R9 is independently selected from the group consisting of Rg and Rh independently represent or Ri represents and wherein Rj represents bicyclic fused or or bicyclic wherein one or more carbon atoms in cyclic ring system may be replaced by and R9 may optionally be substituted with one or more identical or different substituents selected from or di to membered spirocyclic to membered carbocyclic or heterocyclic R10 is selected from the group of SF5 or Z1 and Z2 are independently a direct or Q1 and Q2 are independently selected from a or aromatic an to aromatic ring an to aromatic fused ring a or heteroaromatic an to heteroaromatic ring system or an to heteroaromatic fused ring wherein the heteroatom of the heteroaromatic rings is selected from O or and each ring or ring system may be optionally substituted with one or more substituents independently selected from or Q1 and Q2 are independently selected from a to carbocyclic a or heterocyclic an to ring an to 15 membered spirocyclic ring or an to membered fused ring the heteroatom of the rings is selected from O or and C ring member of the carbocylic or aromatic heterocyclic rings or ring systems may be replaced with or and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17 is selected from SF5 or R9 and and or or R9 and RA together with the atoms to which they are attached may form a to membered carbocyclic ring or ring or heterocyclic ring or ring system which may be optionally substituted with R12 represents R13 and R14 independently represent R15 represents and R16 represents or a carbon atom of R1 from the oxadiazole ring bears at least two fluorine and the b carbon atom of R1 from the oxadiazole ring in case of bears at least one fluorine the present invention relates a compound of Formula R1 is L1 is a direct A is a phenyl ring or pyridyl wherein phenyl or pyridyl ring is unsubstituted or substituted with one or more identical or different RA RA is and wherein RA may be optionally substituted with one or more identical or different Ra selected from and L2 is a fragment selected from the group O k is an integer ranging from 0 to an on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to R7 and R8 are or R9 is selected from the group consisting of and R10 is selected from the group of cycloalkylsulfinyl or Z1 and Z2 are independently a direct and Q1 and Q2 are or aromatic a or heteroaromatic wherein the heteroatom of the heteroaromatic ring is selected from O and and each ring may be optionally substituted with one or more substituents independently selected from or R17 is selected from wherein R12 represents and and R9 and R10 together with the atoms to which they are attached may form a to membered heterocyclic ring or ring system which may be optionally substituted with wherein the heteroatom of the heterocyclic ring or ring system is selected from O and More the compound of Formula I is selected from the group consisting and The present invention also relates to intermediates useful in the preparation of the compounds of Formula Such intermediates include but are not limited to Ia and Ia and Ib wherein R10 are as defined herein The present invention relates to a process for preparing the compound claimed in claim The process of the present invention comprises one or more steps selected from a to p depending upon the definition of In step a compound of formula 1 is esterified into a compound of formula 2 using suitable esterifying reactant and In step the compound of formula 2 by reacting with hydroxyl amine hydrochloride in the presence of suitable base is converted into a compound of formula 3 or the compound of formula 1 by reacting with hydroxyl amine is converted into a compound of formula In step the compound of formula 3 and a compound of formula 8 are cyclized to obtain a compound of formula 4 or the compound of formula and a compound of formula 8 are cyclized to obtain a compound of formula In step the compound of formula 4 is hydrolyzed into a compound of formula In step the compound of formula 5 and a compound of formula 6 are reacted to obtain the compound of formula on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step a compound of formula 6 is reacted with a compound of formula 7 to obtain a compound of formula Ia 6 7 on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step the compound of formula Ia by reacting with hydroxyl amine hydrochloride is converted into a compound of formula Ia Ib L2 steps on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step the compound of formula Ib and a compound of formula 8 are cyclized to obtain a compound of formula or on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step a compound of formula 9 is reacted with ammonium carbamate to obtain a compound of formula Ammonium 9 In step the compound of formula 10 is reacted with a compound of formula 11 to obtain a compound of formula on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step the compound of formula Ia is reacted with hydroxyl amine hydrochloride to obtain a compound of formula on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step the compound of formula Ib and the compound of formula 8 are cyclized to obtain the compound of formula or on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to In step the compound of formula 9 is imidized to obtain a compound of formula In step the compound of formula 11 is cyclized with the compound of formula 8 to obtain a compound of formula or In step the compound of formula 12 is reacted with ammonium carbamate to obtain a compound of formula Ammonium O N carbamate O N R1 R1 N A A NH L1 S N L1 S O R9 R9 12 13 In step the compound of formula 13 is reacted with a compound of formula 14 to obtain the compound of formula R on the left side indicates the point of attachment to and an on the right side indicates the point of attachment to of the present invention can exist as one or more The various stereoisomers include atropisomers and geometric One skilled in the art will appreciate that one stereoisomer may be more active may exhibit beneficial effects when enriched relative to the other or when separated from the other the skilled artisan knows how to to selectively prepare said The of the present invention may be present as a mixture of individual stereoisomers or as an optically active An anion part of the salt in case the of Formula I is a cationic or capable of forming a cation can be inorganic or a cation part of the salt in case the of Formula I is an anionic or capable of forming anion can be inorganic or Examples of inorganic anion part of the salt include but are not limited to hydrogen hydrogen Examples of organic anion part of the salt include but are not limited to arylsulphonates and Examples of inorganic cation part of the salt include but are not limited to alkali and alkaline earth Examples of organic cation part of the salt include but are not limited to methyl tetramethyl choline and Metal ions in metal complexes of the of Formula I are especially the ions of the elements of the second main especially calcium and of the third and fourth main especially tin and and also of the first to eighth transition especially zinc and Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition the metals can be present in the various valencies that they can selected from Formula all and salts typically may exist in more than one Formula I thus includes all crystalline and forms of the that Formula I forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs different crystalline The term refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline these forms having different arrangements conformations of the molecules in the crystal Although polymorphs can have the same chemical they can also differ in composition due to the presence or absence of water or other which can be weakly or strongly bound in the Polymorphs can differ in such physical and biological properties as crystal chemical melting dissolution rate and biological One skilled in the art will appreciate that a polymorph of a compound represented by Formula I can exhibit beneficial effects suitability for preparation of useful improved biological relative to another polymorph or a mixture of polymorphs of the same compound represented by Formula Preparation and isolation of a particular polymorph of a compound represented by Formula I can be achieved by methods known to those skilled in the art for crystallization using selected solvents and In another embodiment the present invention relates to a composition comprising the of Formula I agriculturally acceptable metal constitutional chiral optical geometric or thereof optionally with one or more additional active ingredient with the auxiliary such as inert carrier or any other essential ingredient such as solid diluents and liquid The of Formula I and the compositions according to the are suitable as They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic including which derive especially from the classes of the Peronosporomycetes Basidiomycetes and Deuteromycetes Fungi Some are systemically effective and they can be used in crop protection as foliar fungicides for seed dressing and soil they are suitable for controlling harmful which inter alia occur in wood or roots of The of Formula I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated such as oats or sugar beet or fodder such as stone fruits or soft blackberries or leguminous such as alfalfa or oil such as cocoa castor oil oil ground nuts or such as cucumber or fiber such as hemp or citrus such as grapefruits or such as cucurbits or lauraceous such as cinnamon or energy and raw material such as sugar cane or oil vines grapes and grape juice grape sweet leaf called natural rubber plants or ornamental and forestry such as trees or and on the plant propagation such as and the crop material of these the of Formula I and the compositions according to the invention are important in the control of phytopathogenic fungi on soybeans and on the plant propagation such as and the crop material of the present invention also includes a composition comprising at least one compound of Formula I and The amount of the of Formula I in the composition ranges from gai per active to 10 kgai per active per 100 kg of of Formula I and compositions respectively are used for controlling a multitude of fungi on field such as potatoes sugar coffee or sugar or such as beans or The term propagation is to be understood to denote all the generative or reproductive parts of the plant such as seeds and vegetative plant material such as cuttings and tubers which can be used for the multiplication of the This includes and other parts of including seedlings and young which are to be transplanted after germination or after emergence from These young plants may also be protected before transplantation by a total or partial treatment by immersion or treatment of plant propagation materials with of Formula I and compositions is used for controlling a multitude of fungi on such as barley and cotton and The term is to be understood as including plants which have been modified by mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development see GM crop database Genetically modified plants are which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross mutations or natural one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the Such genetic modifications also include but are not limited to targeted modification of polypeptides by glycosylation or polymer additions such as acetylated or farnesylated moieties or PEG Plants that have been modified by mutagenesis or genetic have been rendered tolerant to applications of specific classes of such as auxin herbicides such as dicamba or bleacher herbicides such as hydroxylphenylpyruvate dioxygenase inhibitors or phytoene desaturase acetolactate synthase inhibitors such as sulfonyl ureas or synthase such as glutamine synthetase inhibitors such as oxidase lipid biosynthesis inhibitors such as acetyl CoA carboxylase or oxynil bromoxynil or herbicides as a result of conventional methods of breeding or genetic plants have been made resistant to multiple classes of herbicides through multiple genetic such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS HPPD auxin or ACCase These herbicide resistance technologies are described in Pest Weed Science 1 and references quoted Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding summer rape BASF being tolerant to or sunflowers being tolerant to sulfonyl Genetic engineering methods have been used to render cultivated plants such as beets and tolerant to herbicides such as glyphosate and some of which are commercially available under the trade names BASF and Bayer plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal especially those known from the bacterial genus particularly from Bacillus such as or vegetative insecticidal proteins VIP3 or insecticidal proteins of bacteria colonizing Photorhabdus or Xenorhabdus toxins produced by such as scorpion arachnid wasp or other toxins produced by such Streptomycetes plant such as pea or barley proteinase such as trypsin serine protease cystatin or papain inactivating proteins such as saporin or steroid metabolism such as cholesterol ecdysone inhibitors or ion channel such as blockers of sodium or calcium juvenile hormone diuretic hormone receptors stilbene bibenzyl chitinases or In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as hybrid truncated or otherwise modified Hybrid proteins are characterized by a new combination of protein Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are in EP427 EP451 und The methods for producing such genetically modified plants are generally known to the person skilled in the art and are in the publications mentioned These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of especially to beetles insects and moths and to nematodes Genetically modified plants capable to synthesize one or more insecticidal proteins described in the publications mentioned and some of which are commercially available such as cultivars producing the CrylAb Plus cultivars producing CrylAb and Cry3Bb1 cultivars producing the Cry9c RW cultivars producing Cry35Ab1 and the enzyme 33B cultivars producing the CrylAc I cultivars producing the Cry1 Ac II cultivars producing CrylAc and Cry2Ab2 cultivars producing a cultivars producing the Cry3A Bt1 1 and Bt176 from Syngenta Seeds cultivars producing the CrylAb toxin and PAT MIR604 from Syngenta Seeds France cultivars producing a modified version of the Cry3A WO MON 863 from Monsanto Europe Belgium cultivars producing the Cry3Bb1 IPC 531 from Monsanto Europe Belgium cultivars producing a modified version of the CrylAc and 1507 from Pioneer Overseas Belgium cultivars producing the Cry1 F toxin and PAT plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to viral or fungal Examples of such proteins are the plant disease resistance genes potato which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum or potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia The methods for producing such genetically modified plants are generally known to the person skilled in the art and are in the publications mentioned plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity bio mass grain starch oil content or protein tolerance to salinity or other environmental factors or tolerance to pests and bacterial or viral pathogens of those plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of specifically to improve human or animal oil crops that produce fatty acids or unsaturated fatty acids DOW Agro plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of specifically to improve raw material potatoes that produce increased amounts of amylopectin BASF The present invention also relates to a method for controlling or preventing infestation of plants by phytopathogenic in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula I or the combination of the present invention or the composition of the present is applied to the seeds of The and of the present invention can be used for controlling or preventing plant The of Formula I and compositions are particularly suitable for controlling the following plant Albugo on vegetables and sunflowers Altemaria leaf on rape brassicola or sugar beets potatoes solani or tomatoes solani or and Aphanomyces on sugar beets and Ascochyta on cereals and tritici on wheat and hordei on Bipolaris and Drechslera Cochliobolus Southern leaf blight or Northern leaf blight on spot blotch on cereals and oryzae on rice and Blumeria graminis on cereals on wheat or Botrytis cinerea Botryotinia grey on fruits and berries vegetables celery and forestry plants and Bremia lactucae on Ceratocystis or on trees and ulmi elm on Cercospora leaf on corn Gray leaf sugar beets sugar soybeans sojina or and Cladosporium on tomatoes leaf and herbarum on Claviceps purpurea on Cochliobolus Helminthosporium of on corn cereals and rice Colletotrichum on cotton corn Anthracnose stalk soft potatoes black beans and soybeans truncatum or Corticium sasakii on Corynespora cassiicola on soybeans and Cycloconium oleaginum on olive Cylindrocarpon fruit tree canker or young vine Nectria or Neonectria on fruit vines Neonectria Black Foot and Dematophora necatrix and stem on Diaporthe phaseolorum on Drechslera on such as barley net and wheat tan rice and Esca on caused by Formitiporia Phaeomoniella chlamydospora Phaeoacremonium Phaeoacremonium aleophilum Botryosphaeria Elsinoe on pome fruits soft fruits and vines Entyloma oryzae on Epicoccum on Erysiphe on sugar beets vegetables such as cucurbits rape Eutypa lata canker or Cytosporina Libertella on fruit vines and ornamental Exserohilum on corn Fusarium root or stem on various such as graminearum or culmorum scab or head on cereals wheat or oxysporum on solani glycines now and tucumaniae and brasiliense each causing sudden death syndrome on and verticillioides on Gaeumannomyces graminis on cereals wheat or and Gibberella on cereals and rice Bakanae Glomerella cingulata on pome fruits and other plants and gossypii on Grainstaining complex on Guignardia bidwellii on Gymnosporangium on rosaceous plants and sabinae on Helminthosporium on cereals and Hemileia vastatrix leaf on Isariopsis clavispora Cladosporium on Macrophomina phaseolina and stem on soybeans and Microdochium nivale snow on cereals wheat or Microsphaera diffusa on Monilinia fructicola and fructigena and twig brown on stone fruits and other rosaceous Mycosphaerella on soft fruits and ground such as graminicola Septoria Septoria on wheat or fijiensis Sigatoka on Peronospora on cabbage rape onions tobacco and soybeans Phakopsora pachyrhizi and meibomiae on Phialophora on vines tracheiphila and and soybeans stem Phoma lingam and stem on rape and cabbage and betae leaf spot and on sugar Phomopsis on vines can and leaf and soybeans stem Diaporthe Physoderma maydis on Phytophthora fruit and stem on various such as paprika and cucurbits soybeans potatoes and tomatoes late and trees sudden oak Plasmodiophora brassicae on radish and other Plasmopara viticola downy on vines and halstedii on Podosphaera on rosaceous pome and soft leucotricha on Polymyxa on such as barley and wheat and sugar beets and thereby transmitted viral Pseudocercosporella herpotrichoides Tapesia on wheat or Pseudoperonospora on various cubensis on cucurbits or humili on Pseudopezicula tracheiphila fire disease or on Puccinia on various triticina or leaf striiformis or yellow hordei graminis or black or recondita or leaf on such as barley or kuehnii on sugar cane and asparagi on Pyrenophora repentis on wheat or teres on Pyricularia oryzae Magnaporthe rice on rice and grisea on turf and Pythium on sugar vegetables and various other plants ultimum or Ramularia leaf Physiological leaf on barley and beticola on sugar Rhizoctonia on sugar vegetables and various other solani and stem on solani on rice or cerealis spring on wheat or Rhizopus stolonifer soft on vines and Rhynchosporium secalis on rye and Sarocladium oryzae and attenuatum on Sclerotinia rot or white on vegetables and field such as sunflowers and soybeans rolfsii or Septoria on various glycines on tritici on wheat and nodorum on Uncinula necator Oidium on Setospaeria on corn Helminthosporium and Sphacelotheca on head sorghum und sugar Sphaerotheca fuliginea on Spongospora subterranea on potatoes and thereby transmitted viral Stagonospora on nodorum Leptosphaeria on Synchytrium endobioticum on potatoes wart Taphrina deformans curl on peaches and pruni on Thielaviopsis root on pome soybeans and basicola Chalara Tilletia bunt or stinking on such as tritici wheat and controversa on Typhula incarnata snow on barley or Urocystis occulta on Uromyces on such as beans and sugar beets Ustilago on cereals nuda and corn corn and sugar Venturia on apples and and Verticillium on various such as fruits and soft vegetables and field dahliae on potatoes and The compounds of formula the combinations or the compositions thereof may be used to treat several fungal examples of pathogens of fungal diseases which can be treated in accordance with the invention Ustilaginales such as Ustilaginoidea Ustilago Ustilago Ustilago rusts for example those caused by Pucciniales such as Cerotelium Chrysomyxa Coleosporium Hemileia Puccinia Puccinia Puccinia Puccinia Puccinia Puccinia Puccinia striiformis Puccinia striiformis Pucciniastrum or Uredinales such as Cronartium Gymnosporangium Melampsora Phakopsora Phragmidium Physopella Tranzschelia discolor and Uromyces and other rots and diseases such as those caused by Cryptococcus Exobasidium Marasmiellus Mycena Sphacelotheca Typhula Urocystis ltersonilia Corticium Laetisaria Waitea Rhizoctonia Thanetephorus Entyloma Entylomella Neovossia moliniae and Tilletia such as Physoderma such as Choanephora Mucor and Rhizopus In another embodiment diseases caused by rust disease for example Gymnosporangium for example Gymnosporangium Hemileia for example Hemileia Phakopsora for example Phakopsora pachyrhizi or Phakopsora Puccinia for example Puccinia Puccinia graminis oder Puccinia Uromyces for example Uromyces In Cronartium ribicola pine blister Gymnosporangium Hemileia vastatrix Phakopsora meibomiae and pachyrhizi Puccinia coronata Rust of Oats and Puccinia graminis rust of wheat and Kentucky or black rust of Puccinia hemerocallidis Puccinia persistens triticina rust or or red Puccinia sorghi in Puccinia striiformis in Uromyces appendiculatus of Uromyces phaseoli Puccinia melanocephala in Puccinia kuehnii in Plants which can be treated in accordance with the invention include the such as Rosaceae sp example pome fruits such as almonds and Ribesioidae Juglandaceae Betulaceae Anacardiaceae Fagaceae Moraceae Oleaceae Actinidaceae Lauraceae Musaceae example banana trees and Rubiaceae example Theaceae Sterculiceae Rutaceae example oranges and Vitaceae example Solanaceae example Liliaceae Asteraceae example Umbelliferae Cruciferae Chenopodiaceae Cucurbitaceae example Alliaceae example Papilionaceae example major crop such as example cereals such as millet and Asteraceae example Brassicaceae example white red Brussels pak and oilseed horseradish and Fabacae example Papilionaceae example soya Solanaceae example Chenopodiaceae example sugar fodder swiss Malvaceae example useful plants and ornamental plants for gardens and wooded and genetically modified varieties of each of these More preference is given to controlling the following diseases of soya Fungal diseases on pods and seeds for by Altemaria leaf spot atrans Anthracnose gloeosporoides dematium brown spot glycines cercospora leaf spot and blight Cercospora choanephora leaf blight infundibulifera trispora dactuliophora leaf spot downy mildew drechslera blight frogeye leaf spot leptosphaerulina leaf spot phyllostica leaf spot pod and stem blight powdery mildew pyrenochaeta leaf spot rhizoctonia and web blight rust Phakopsora scab stemphylium leaf blight target spot Fungal diseases on roots and the stem base for by black root rot charcoal rot fusarium blight or root and pod and collar rot Fusarium Fusarium Fusarium mycoleptodiscus root rot neocosmospora pod and stem blight stem canker phaseolorum phytophthora rot brown stem rot pythium rot Pythium Pythium Pythium Pythium rhizoctonia root stem and sclerotinia stem decay sclerotinia southern blight thielaviopsis root rot The present invention also relates to the use of compounds of formula the combinations or the compositions thereof for controlling or preventing the following plant Puccinia on various for but not limited to triticina or leaf striiformis or yellow hordei graminis or black or recondita or leaf on such as barley or rye and Phakopsoraceae on various in particular Phakopsora pachyrhizi and meibomiae on Hemileia vastatrix Uromyces Uromyces fabae and Uromyces phaseoli of The present invention further relates to the use of compounds of formula the combinations or the compositions thereof for controlling or preventing against phytopathogenic fungi such as Phakopsora Phakopsora of agricultural crops and or horticultural The of Formula the combinations and the compositions are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of The term of is to be understood to denote the protection of technical and such as paper and paint cooling fiber or against the infestation and destruction by harmful such as fungi and As to the protection of wood and other the particular attention is paid to the following harmful Ascomycetes such as Ophiostoma Ceratocystis Aureobasidium Sclerophoma Chaetomium Humicola Petriella Trichurus Basidiomycetes such as Coniophora Coriolus Gloeophyllum Lentinus Pleurotus Serpula and Tyromyces Deuteromycetes such as Aspergillus Cladosporium Penicillium Trichoderma Altemaria Paecilomyces and Zygomycetes such as Mucor and in addition in the protection of stored products and harvest the following yeast fungi are worthy of Candida and Saccharomyces In one embodiment the of Formula the combinations and the compositions are particularly suitable for controlling the following plant Phakopsora pachyrhizi and meibomiae on The present invention further relates to a method for controlling or preventing phytopathogenic The method comprises treating the fungi or the plant locus soil or seeds to be protected against fungal with an effective amount of at least one compound of Formula I or the combinations or the compositions comprising at least one compound of Formula The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and According to the present the term is understood to denote natural substances of plant or animal origin and their processed which have been taken from the natural life cycle and for which protection is Stored products of crop plant such as plants or parts for example fruits or can be protected in the freshly harvested state or in processed such as pressed or which process is also known as Also falling under the definition of stored products is whether in the form of crude such as construction electricity pylons and or in the form of finished such as furniture or objects made from Stored products of animal origin are hairs and the The combinations according the present invention can prevent disadvantageous effects such as discoloration or Preferably is understood to denote natural substances of plant origin and their processed more preferably fruits and their processed such as stone soft fruits and citrus fruits and their processed The of Formula the combinations and the compositions may be used for improving the health of a The invention also relates to a method for improving plant health by treating a its propagation material the locus where the plant is growing or is to grow with an effective amount of I and compositions The term is to be understood to denote a condition of the plant its products which is determined by several indicators alone or in combination with each other such as yield increased biomass increased content of valuable plant vigor improved plant growth greener leaves quality improved content or composition of certain and tolerance to abiotic biotic The above identified indicators for the health condition of a plant may be interdependent or may result from each The of Formula I can be present in different crystal modifications or polymorphs whose biological activity may They are likewise subject matter of the present The of Formula I are employed as such or in the form of compositions for treating the fungi or the plant propagation such as materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active The application can be carried out both before and after the infection of the plant propagation such as materials or rooms by the Plant propagation materials may be treated with of Formula the combinations and the compositions thereof protectively either at or before planting or The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of Formula An agrochemical composition comprises a fungicidally effective amount of a compound of Formula The term denotes an amount of the composition or of the of Formula which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated Such an amount can vary in a broad range and is dependent on various such as the fungal species to be the treated cultivated plant or the climatic conditions and the specific compound of Formula I The of Formula their metal polymorphs or the agriculturally acceptable salts thereof can be converted into customary types of agrochemical and mixtures Examples for composition types are suspensions emulsifiable concentrates emulsions capsules wettable powders or dusts pressings granules insecticidal articles as well as gel formulations for the treatment of plant propagation materials such as seeds These and further compositions types are defined in the of pesticide formulation types and international coding Technical Monograph 6th May CropLife The compositions are prepared in a known such as described by Mollet and Formulation Wiley 2001 or New developments in crop protection product Agrow Reports Suitable auxiliaries are liquid solid carriers or penetration protective adhesion feeding tackifiers and Suitable solvents and liquid carriers are water and organic such as mineral oil fractions of medium to high boiling diesel oils of vegetable or animal cyclic and aromatic alkylated benzyl fatty acid fatty fatty acid dimethyl and mixtures Suitable solid carriers or fillers are mineral silica diatomaceous calcium magnesium magnesium ammonium ammonium ammonium products of vegetable cereal tree bark wood nutshell and mixtures Suitable surfactants are such as nonionic and amphoteric block and mixtures Such surfactants can be used as penetration protective or Examples of surfactants are listed in Emulsifiers Glen 2008 or North American Suitable anionic surfactants are alkaline earth or ammonium salts of and mixtures Examples of sulfonates are alkylaryl diphenyl lignin sulfonates of fatty acids and sulfonates of ethoxylated sulfonates of alkoxylated sulfonates of condensed sulfonates of sulfonates of naphthalenes and alkyl sulfosuccinates or Examples of sulfates are sulfates of fatty acids and of ethoxylated of of ethoxylated or of fatty acid Examples of phosphates are phosphate Examples of carboxylates are alkyl and carboxylated alcohol or alkylphenol Suitable nonionic surfactants are fatty acid amine polymeric and mixtures Examples of alkoxylates are compounds such as fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 Ethylene oxide propylene oxide may be employed for the preferably ethylene Examples of fatty acid amides are fatty acid glucamides or fatty acid Examples of esters are fatty acid glycerol esters or Examples of surfactants are ethoxylated sucrose and glucose esters or Examples of polymeric surfactants are or copolymers of vinyl vinyl or vinyl Suitable cationic surfactants are quaternary for example quaternary ammonium compounds with one or two hydrophobic or salts of primary Suitable amphoteric surfactants are alkylbetains and Suitable block polymers are block polymers of the or type comprising blocks of polyethylene oxide and polypropylene or of the type comprising polyethylene oxide and polypropylene Suitable polyelectrolytes are polyacids or Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb Examples of polybases are polyvinyl amines or polyethylene Suitable adjuvants are which have a negligible or even no pesticidal activity and which improve the biological performance of the compounds of Formula I on the Examples are mineral or vegetable and other Further examples are listed by Adjuvants and Agrow Reports Informa chapter Suitable thickeners are polysaccharides xanthan carboxymethyl inorganic clays modified or and Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and Suitable agents are ethylene propylene urea and Suitable agents are long chain and salts of fatty Suitable colorants in or are pigments of low water solubility and Examples are inorganic colorants iron titan iron and organic colorants and phthalocyanine Suitable tackifiers or binders are polyvinyl polyvinyl polyvinyl biological or synthetic and cellulose Examples for composition types and their preparation concentrates of a compound of Formula I and wetting agent alcohol are dissolved in water in a solvent ad 100 The active substance dissolves upon dilution with Dispersible concentrates of a compound of Formula I and dispersant polyvinyl are dissolved in organic solvent ad 100 Dilution with water gives a Emulsifiable concentrates of a compound of Formula I and emulsifiers calcium dodecylbenzenesulfonate and castor oil are dissolved in organic solvent aromatic ad 100 Dilution with water gives an Emulsions of a compound of Formula I and emulsifiers calcium dodecylbenzenesulfonate and castor oil are dissolved in organic solvent aromatic This mixture is introduced into water ad 100 by means of an emulsifying machine and made into a homogeneous Dilution with water gives an Suspensions In an agitated ball of a compound of Formula I are comminuted with addition of dispersants and wetting agents sodium lignosulfonate and alcohol thickener xanthan and water ad 100 to give a fine active substance Dilution with water gives a stable suspension of the active For FS type composition up to 40 binder polyvinyl is granules and granules of a compound of Formula I are ground finely with addition of dispersants and wetting agents sodium lignosulfonate and alcohol ad 100 and prepared as dispersible or granules by means of technical appliances spray fluidized Dilution with water gives a stable dispersion or solution of the active powders and powders of a compound of Formula I are ground in a mill with addition of dispersants sodium wetting agents alcohol and solid carrier silica ad 100 Dilution with water gives a stable dispersion or solution of the active Gel In an agitated ball of a compound of Formula I are comminuted with addition of dispersants sodium thickener carboxymethyl and water ad 100 to give a fine suspension of the active Dilution with water gives a stable suspension of the active Microemulsion of a compound of Formula I are added to organic solvent blend fatty acid dimethyl amide and surfactant blend alcohol ethoxylate and arylphenol and water ad 100 This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable Microcapsules An oil phase comprising of a compound of Formula water insoluble organic solvent aromatic acrylic monomers methacrylic acid and a or are dispersed into an aqueous solution of a protective colloid polyvinyl Radical polymerization results in the formation of an oil phase comprising of a compound of Formula I according to the water insoluble organic solvent aromatic and an isocyanate monomer are dispersed into an aqueous solution of a protective colloid polyvinyl The addition of a polyamine results in the formation of polyurea The monomers amount to The relate to the total CS Dustable powders of a compound of Formula I are ground finely and mixed intimately with solid carrier finely divided ad 100 Granules of a compound of Formula I are ground finely and associated with solid carrier ad 100 Granulation is achieved by or fluidized volume liquids of a compound of Formula I are dissolved in organic solvent aromatic ad 100 The compositions types to may optionally comprise further such as and The agrochemical compositions generally comprise between and preferably between and and in particular between and by weight of active ingredient The active ingredients are employed in a purity of from to preferably from to to NMR For the purposes of treatment of plant propagation particularly solutions for seed treatment Suspoemulsions flowable concentrates powders for dry treatment powders for slurry treatment powders emulsions emulsifiable concentrates and gels are usually The compositions in question after active substance concentrations of from to by preferably from to in the Application can be carried out before or during Methods for applying of Formula the combinations and the compositions onto plant propagation especially include and soaking as well as application of Formula the combinations and the compositions are applied on to the plant propagation material by a method such that germination is not by seed coating and When employed in plant the amounts of active substances applied depending on the kind of effect from to 2 kg per preferably from to 2 kg per more preferably from to kg per and in particular from to kg per In treatment of plant propagation materials such as by coating or drenching amounts of active substance of from to 1000 preferably from 1 to 1000 more preferably from 1 to 100 g and most preferably from 5 to 100 per 100 kilogram of plant propagation material are generally When used in the protection of materials or stored the amount of active substance applied depends on the kind of application area and on the desired Amounts customarily applied in the protection of materials are g to 2 preferably g to 1 of active substance per cubic meter of treated Various types of or and further pesticides growth may be added to the active substances or the compositions comprising them as premix if appropriate not until immediately prior to use These agents can be admixed with the compositions according to the invention in a weight ratio of to preferably to A pesticide is generally a chemical or biological agent as pesticidally active antimicrobial or that through its effect kills or otherwise discourages Target pests can include plant nematodes and microbes that destroy cause spread disease or are vectors for The term includes also plant growth regulators that alter the expected or reproduction rate of defoliants that cause leaves or other foliage to drop from a usually to facilitate desiccants that promote drying of living such as unwanted plant plant activators that activate plant physiology for defense of against certain safeners that reduce unwanted herbicidal action of pesticides on crop and plant growth promoters that affect plant physiology to increase plant yield or any other quality parameter of the harvestable goods of a crop The user applies the composition according to the invention usually from a predosage a knapsack a spray a spray or an irrigation the agrochemical composition is made up with further auxiliaries to the desired application concentration and the spray liquor or the agrochemical composition according to the invention is thus 20 to 2000 preferably 50 to 400 of the spray liquor are applied per hectare of agricultural useful According to one individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications seed treater seed pelleting knapsack and further auxiliaries may be if one embodiment of the invention is a kit for preparing a usable pesticidal the kit comprising a composition comprising component as defined herein and at least one and a composition comprising component as defined herein and at least one and optionally a composition comprising at least one auxiliary and optionally a further active component as defined The of Formula the combinations and the compositions thereof comprising them in the use as fungicides with other fungicides may result in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance in many extraordinary effects are The present invention also relates to the combination comprising at least one compound of Formula I and at least one further pesticidally active substance selected from the group of plant growth fertiliers and The pesticidally active substances reported in WO2015185485 pages and WO2017093019 pages can be used in conjunction with which the of Formula The active substances referred to as component their preparation and their activity against harmful fungi is known these substances are commercially The compounds described by IU PAC their preparation and their pesticidal activity are also known Plant EP428941 WO0154501 WO WO13092224 and The present invention furthermore relates to agrochemical mixtures comprising at least one compound of Formula I and at least one further active substance useful for plant selected from the groups to in particular one further one or more fungicide from the groups to as described and if desired one suitable solvent or solid combating harmful fungi with a mixture of of Formula I and at least one fungicide from groups to as described is advantageous than combating those fungi with individual of Formula I or individual fungicides from groups to By applying of Formula I together with at least one pesticidally active substance from groups to an enhanced effect can be This can be obtained by applying the of Formula I and at least one further pesticidally active substance either jointly as or or in wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further pesticidally active The order of application is not essential for working of the present When applying of Formula I and a pesticidally active substance sequentially the time between both applications may vary between 2 hours to 7 Also a broader range is possible ranging from hour to 30 preferably from hour to 14 particularly from 1 hour to 7 days or from hours to 5 even more preferred from 2 hours to 1 In the binary mixtures and compositions according to the invention the weight ratio of the component and the component generally depends from the properties of the active components usually it is in the range of to regularly in the range of to preferably in the range of to more preferably in the range of to even more preferably in the range of to and in particular in the range of to According to a further embodiment of the binary mixtures and compositions the weight ratio of the component and the component usually is in the range of to often in the range of to regularly in the range of to preferably in the range of to more preferably in the range of to even more preferably in the range of to and in particular in the range of to In the ternary compositions according to the invention comprising the component and component and a compound III the weight ratio of component and component depends from the properties of the active substances usually it is in the range of to regularly in the range of to preferably in the range of to more preferably in the range of to and in particular in the range of to and the weight ratio of component and component usually it is in the range of to regularly in the range of to preferably in the range of to more preferably in the range of to and in particular in the range of to Any further active components if added in a ratio of to to the component These ratios are also suitable for inventive mixtures applied by seed The present invention also relates to a process for preparing the of the present The process for preparing the of the present invention is described in the experimental section in more The invention disclosed in the present disclosure shall now be elaborated with the help of schemes and CHEMISTRY General Synthetic Scheme L2 is L2b N R9 I Iodobenzene diacetate R10 R10 HS R9 S NH Ammonium O carbamate 18h Step 5 Step 6 Scheme L2 is L2a and K is H Iodobenzene diacetate R10 R HS R9 S NH Ammonium O K2CO3 carbamate MeI 18h Step 5 Step 6 Scheme L2 is L2a and K is 0 H Iodobenzene diacetate R10 HS Ammonium carbamate MeI 18h Step 5 Step 6 Example Preparation of Methyl N To a stirred solution of acid 170 in formamide potassium carbonate 255 was added at 25 oC and cooled to 0 To the resulting reaction methyl iodide 255 was slowly The resulting reaction mixture was stirred at for 2 After completion of the the reaction mixture was cooled to 25 oC and crushed ice was poured into it with Stirring was continued for 10 minutes to obtain a The precipitate was washed with water and dried under reduced pressure to obtain methyl 153 90 To a stirred solution of methyl in methanol sodium bicarbonate and hydroxylamine hydrochloride were The resulting reaction mixture was heated to reflux for 4 After completion of the the reaction mixture was cooled to 25 oC and The filtrate was concentrated under reduced pressure to obtain 83 Methyl H To a stirred solution of in tetrahydrofuran trifluoroacetic anhydride was added at 0 under nitrogen The resulting reaction mixture was stirred at 25 oC for 16 h and diluted with ethyl acetate Ethyl acetate layer was washed three times with Sodium bicarbonate dried over anhydrous sodium sulphate and concentrated under reduced The crude residue was purified by column chromatography ethyl acetate in on silica gel to obtain methyl 44 Step To a stirred solution of methyl in tetrahydrofuran a solution of sodium hydroxide 99 in water was added dropwise by a dropping funnel at 0 The resulting reaction mixture was stirred for 16 h at 25 After completion of the the solvent was removed by evaporation under reduced Water was added to the residue and cooled to 0 and acidified to pH 3 with 3N aqueous hydrochloric The precipitate was collected by washed with and dried to obtain acid 79 To a stirred solution of in acetonitrile potassium carbonate was added at 0 Ice bath was removed and the reaction mixture was stirred for 30 min at 25 The reaction mixture was cooled again to 0 and methyl iodide was added The reaction mixture was stirred at 25 oC for 4 After completion of the the reaction mixture was diluted with ethyl acetate and washed three times with water The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 73 The crude product was used as such in the next step without To a stirred solution of in methanol was added ammonium carbamate Then diacetoxy iodobenzene was slowly added portion wise at 0 The resulting reaction was stirred at 25 oC for 12 After completion of the methanol was evaporated under reduced diluted with ethyl acetate and washed with water The ethyl acetate layer was washed two times with saturated sodium bicarbonate solution dried over anhydrous sodium sulphate and concentrated under reduced The crude residue was purified using column chromatography on silica gel to obtain 61 Step Preparation of To a stirred solution of acid in dry dichloromethane hydrochloride and were added at 5 under nitrogen Then was and the reaction mixture was stirred at 25 oC for 16 After completion of the product was extracted by dichloromethane The dichloromethane layer was washed two times with brine solution dried over anhydrous sodium sulphate and The residue was purified by column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain 16 Table The following compounds were prepared by the procedure analogous to that of the Compound 3 using appropriate starting 9 9 9 9 9 9 9 9 9 Compound 12 Step The reaction mixture containing and cesium carbonate in toluene was purged with nitrogen for 10 The racemic BINAP and were added and the reaction mixture was stirred at 105 for 18 After completion of the the reaction mixture was cooled to 25 and was extracted with ethyl acetate the ethyl acetate layer was washed by water dried over anhydrous sodium sulphate and The crude product Step hydroxybenzimidamide To a stirred solution of in ethanol sodium bicarbonate and hydroxylamine hydrochloride were added and stirred at 65 for 16 After completion of the reaction the reaction mixture was cooled to 25 and The filtrate was concentrated to obtain a crude product hydroxybenzimidarnide 99 Step To a stirred solution of hydroxybenzimidarnide in tetrahydrofuran trifluoroacetic anhydride was added at 0 and stirred at 25 for 16 After completion of the the reaction mixture was filtered The filtrate was concentrated to obtain the crude The crude product was purified by column chromatography on silica gel using eluent hexane to Ethyl acetate in hexane to obtain pure 60 Table The following compounds were prepared by the procedure analogous to that of the compound 12 using appropriate starting Preparation of 3 Compound 29 Step To a stirred solution of in dimethyl formamide potassium was added at 0 under nitrogen The resulting reaction mixture was stirred at 25 for 15 minutes and again cooled to 0 Then added and reaction mixture was stirred at 25 for 30 Saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and stirred at 0 oC for 10 The ethyl acetate layer was washed with water dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 96 Step hydroxybenzimidamiden F O F O S To a stirred solution of in ethanol hydroxylamine hydrochloride and sodium bicarbonate were added at 25 The resulting reaction mixture was heated to 65 for 12 After completion of the the reaction mixture was filtered through sintered The filtrate was evaporated under reduced pressure to obtain hydroxybenzimidamide Step 3 To a stirred solution of hydroxybenzimidamide in tetrahydrofuran trifluoroacetic acid was added at 0 under nitrogen The resulting reaction mixture was stirred at 25 oC for 16 After completion of the the reaction mixture was diluted with ethyl acetate and washed three times with water The ethyl acetate layer was washed with aqueous saturated sodium bicarbonate dried over anhydrous sodium sulphate and concentrated under reduced The crude residue was purified by column chromatography hexane to ethyl acetate in on silica gel to obtain as a gum 28 Table The following compounds were prepared by the procedure analogous to that of the compound using appropriate starting Compound IUPAC Name Structure Yield Example Preparation of compound 155 To a stirred solution of aqueous ammonia in tetrahydrofuran fluorobenzenesulfonyl chloride was added at The resulting reaction mixture was stirred at 25 oC for 16 Sodium bicarbonate was added and stirred at 25 for 10 The reaction mixture was concentrated to obtain 98 F To a stirred solution of acid in dry under nitrogen ethylcarbodiimide hydrochloride was added followed by the addition of dimethylaminopyridine and at 25 The resulting reaction mixture was stirred for 12 h at 25 After completion of the the reaction mixture was diluted with dichloromethane and washed thrice with water Dichloromethane layer was dried over anhydrous sodium The volatiles were evaporated under Crude residue was purified by preparative HPLC to obtain 35 Table The following compounds were prepared the procedure analogous to that of the Compound 155 using appropriate starting Example Preparation of F Step F To a stirred solution of in dimethyformamide potassium was added at 0 and allowed to stirr at 25 for 10 The reaction mixture was cooled again to 0 and difluorobenzonitrile was The stirring was continued at 25 for 4 The reaction mixture was diluted with ethyl acetate and washed twice with water The obtained crude product was purified by flash column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain pure Step hydroxybenzimidamide To a stirred solution of in ethanol sodium bicarbonate and hydroxylamine hydrochloride were added at 25 The resulting reaction mixture was stirred at 70 for 16 The reaction mixture was filtered and the filtrate was evaporated under vacuum to obtain 90 F To a stirred solution of hydroxybenzimidamide in tetrahydrofuran trifluoro acetic anhydride was added slowly at 0 under nitrogen atmosphere and then stirred at 25 for 16 The resulting reaction mixture was diluted with ethyl acetate The ethyl acetate layer was washed twice with aqueous sodium bicarbonate solution dried over anhydrous sodium sulphate and evaporated under Crude product was purified by flash column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain Table The following compounds were prepared by the procedure analogous to that of the Compound 165 using appropriate starting Example Preparation of Step was prepared by the procedure described in step 2 of example Step F was prepared by the procedure described in of example Step Synthesis of sulfanone was prepared by the procedure described in of example Step Synthesis of O N To a stirred solution of sulfanone and triethylamine in dichloromethane chloride was added at 0 The resulting reaction mixture was stirred for 2 h at 25 The volatiles were evaporated and the residue was extracted by ethyl acetate Ethyl acetate layer was washed thrice with water dried over anhydrous sodium sulphate and concentrated under Crude product was purified by flash column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain pure 79 Table The following compounds were prepared by the procedure analogous to that of the compound 172 using appropriate starting Example Preparation of F Compound 182 Step was prepared by the procedure described in of example Step was dissolved in followed by addition of at 0 0C and stirred for 15 minutes at bromide was added and allowed to stirr for 3 After completion of the ethyl acetate and saturated ammonium chloride solution were added to the reaction Ethyl acetate layer was isolated and washed twice with water dried over anhydrous sodium sulphate and concentrated under vacuum to obtain Step was prepared by procedure as described in of example Step sulfanone N O To a stirred solution of in tetrahydrofuran trifluoroacetic anhydride was added slowly at 5 under nitrogen The resulting reaction mixture was stirred for 18 h at 25 After completion of the the reaction mixture was diluted with ethyl acetate The ethyl acetate layer was washed with saturated sodium bicarbonate solution dried over anhydrous sodium sulphate and concentrated under The crude product was purified by column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain sulfanone 38 Table The following compounds were prepared by the procedure analogous to that of the compound 182 using appropriate strating Com ound IUPAC Name Structure Yield Example Preparation of Compound 186 acid OH To a stirred solution of acid in ethanol of aqueous hydroxylamine solution 155 was added at 0 and stirred at 65 oC for 4 The reaction mixture was concentrated under vacuum to obtain acid Preparation of acid F To a stirred solution of acid in tetrahydrofuran trifluoroacetic anhydride was added at 0 under nitrogen atmosphere and stirred at 25 oC for 16 After completion of the the reaction mixture was concentrated and purified by column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain pure acid Preparation of F To a stirred solution of acid in dichloromethane hydrochloride and were added at under nitrogen mmol was added and stirred at 25 oC for 16 The resulting reaction mixture was diluted with dichloromethane and washed twice with water Dichloromethane layer was collected and dried over anhydrous sodium sulphate and concentrated under Crude product was purified by preparative HPLC to obtain Table The following compounds were prepared by the procedure analogous to that of the compound 186 using appropriate starting Example Preparation of O Step Synthesis of acid OH To a stirred solution of acid in ethanol 50 of aqueous hydroxylamine solution was The resulting reaction mixture was stirred at 65 for 4 After completion of the the volatiles were evaporated under vacuum to obtain acid Step acid 3 O N To a stirred solution of acid 33 in tetrahydrofuran trifluoroacetic anhydride was added slowly at under nitrogen The resulting reaction mixture was stirred for 18 h at 25 Solvent was removed under reduced Crude residue was stirred with water at 25 Obtained precipitate was filtered and solid was dried under vacuum to obtain acid Step Synthesis of Compound 196 23 was synthesized by the procedure as described in of example Table The following compounds were prepared by the procedure analogous to that of the Compound 196 using appropriate starting Compound IUPAC Name Structure Yield Example Preparation of compound Step Preparation of H To a solution of methyl in ethanol hydroxylamine hydrochloride 98 and sodium bicarbonate 98 were The resulting reaction mixture was stirred at 65 oC for 18 The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain 99 Step Preparation of methyl F To a solution of in tetrahydrofuran trifluoroacetic anhydride 81 was added at and stirred at 25 for 16 h The resulting reaction mixture was poured into ice cold mixture of ethyl acetate and saturated sodium bicarbonate solution with stirring pH must remain The ethyl acetate layer was washed twice with saturated sodium bicarbonate solution dried over anhydrous sodium sulphate and The crude product was purified by flash column chromatography on silica gel using ethyl acetate in hexane as an eluent to obtain pure methyl 58 O To a stirred solution of methyl and toluene trimethylaluminium in hexane was added at and stirred at 65 for 16 The resulting reaction mixture was cooled to 25 and poured into a mixture of acetic acid and ethyl acetate stirred at 25 for 10 organic layer was Aqueous layer was again extracted into ethyl acetate Ethyl acetate layer was washed by water dried over anhydrous sodium sulphate and concentrated under reduced Purification was done by column chromatography on silica gel using hexane to ethyl acetate in hexane as an eluent to obtain 78 Table The following compound was prepared by the procedure analogous to that of the compound using appropriate starting BIOLOGY Biological Test Examples for fungal pathogens Example Pyricularia oryzae Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 60 relative humidity for seven days and radial growth was Compounds 3 13 14 15 17 18 19 20 22 23 27 29 96 97 106 114 117 122 124 127 130 133 134 137 138 139 141 143 144 145 146 147 148 149 151 151 152 152 165 166 167 169 171 181 182 183 184 185 at 300 ppm gave more than control in these tests when compared to the untreated check which showed extensive disease Example Rhizoctonia solani sheath black Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 60 relative humidity for seven days and radial growth was Compounds 15 50 90 128 133 at 300 ppm gave more than control in these tests when compared to the untreated check which showed extensive disease Example Botrytis cinerea Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 90 relative humidity for seven days and radial growth was Compounds 14 15 17 23 48 90 108 109 133 138 139 140 153 156 157 at 300 ppm gave more than in these tests when compared to the untreated check which showed extensive disease Example Alternaria solani blight of Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 60 relative humidity for seven days and radial growth was Compounds 13 14 15 17 18 20 23 33 47 48 52 56 59 62 71 73 75 94 96 99 108 109 117 137 148 157 158 162 163 at 300 ppm gave more than control in these tests when compared to the untreated check which showed extensive disease Example Colletotrichum capsici Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 60 relative humidity for seven days and radial growth was Compounds 13 15 17 18 22 23 133 156 181 at 300 ppm gave more than control in these tests when compared to the untreated check which showed extensive disease Example Septoria lycopersici spot of Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 70 relative humidity for seven days and radial growth was Compound 134 at 300 ppm gave more than control in these tests when compared to the untreated check which showed extensive disease Example Fusarium culmorum rot of Compounds were dissolved in DMSO then added to Potato Dextrose Agar medium just prior to dispensing it into petri 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile After each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture Plates were incubated in growth chambers at temperature and 60 relative humidity for seven days and radial growth was Example Phakopsora pachyrhizi test in Soybean Compounds were dissolved in then mixed with water to the calibrated spray volume of 50 mL and poured into the spray bottles for further To test the preventive activity of healthy young soybean plants raised in the greenhouse were sprayed with active compound preparation at the stated application rates inside the spray cabinets using hallowcone One day after the plants were inoculated with spore suspension containing Phakopsora pachyrhizi The inoculated plants were then kept in greenhouse chamber at 250C temperature 90 relative humidity for disease A visual assessment of performance was carried out by rating the disease severity on treated plants on 10 15 days after Efficacy of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated The sprayed plants were also assessed for plant compatibility by recording symptoms like chlorosis Compounds 1 2 3 4 5 6 7 9 10 12 14 15 16 17 18 19 20 21 22 23 25 26 27 28 30 31 36 38 40 42 47 48 50 51 52 53 54 56 57 58 59 62 71 75 85 89 91 92 96 99 108 109 110 showed at 500 ppm control in these tests when compared to the untreated check which showed extensive disease insufficientOCRQuality
We Claim:
1. A compound of For l I
R1 A R10
N L1 L2
Formula I
wherein:
R1 is C1-C2-haloalkyl;
L1 is a direct bond, -CR2R3-, -C(=O)-, -O-, -S(=O)0-2-, -NR4-, -CR2R3C(=O)-, -S(=O)0-2(-NR4)-, -SR5(=O)0-1(=N)-, -S(=O)0-1(=NR4)-, -SR5(=O)0-1(=N)-CR2R3-, wherein, an expression“-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(=O), C(=S), C(=CR2aR3a) and C=NR6; or
A is an aromatic or non-aromatic heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(=O)0-2, and S(=O)0-1(=NR6) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(=O), C(=S), C(=CR2aR3a) and C=NR6; and
wherein, A is unsubstituted or is substituted with one or more identical or different RA groups,
wherein, RA is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8- cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6- haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6- haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6- alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, or C1-C6-dialkylaminocarbonyloxy, 5- to 11- membered spirocyclic ring, and 3- to 6- membered carbocyclic or heterocyclic ring, wherein, RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C1-C6-alkoxy- C1-C4-alkyl, C3-C8- halocycloalkyl, C1-C6-alkylamino, di-C1-C6-alkylamino or C3-C8-cycloalkylamino;
wherein, 5- to 11- membered spirocyclic ring, 3- to 6- membered carbocyclic or heterocyclic ring may be optionally substituted with one or more identical or different substituents selected from halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3- C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxyalkyl, C1-C6- hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1- C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C6- cycloalkylamino, C1-C6-alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6- alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6- alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, or di-C1-C6-alkylaminocarbonyloxy, or two RA together with the atoms to which they are attached may form a 3- to 10- membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different Ra,
wherein, the C atom of the non-aromatic carbocyclic ring may be optionally replaced by C(=O), C(=S), C(=CR2bR3b) and C=NR6a or,
wherein, the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(=O)0-2, and S(=O)0-1(=NR6a) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(=O), C(=S), C(=CR2bR3b) and C=NR6a;
R4, R6, R6a, R6b, and R6c are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C=O)-Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, tri-C1-C6-alkylamino or C3-C8-cycloalkyl;
Rb and Rc represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl or C3-C8-halocycloalkyl,
Rd represents hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl or C3-C8-halocycloalkyl, and
Re represents hydrogen, halogen, cyano, C1-C
haloalkoxy, C3-C8-cycloalkyl or C3-C8-halocycl
R9 R7 R8 (O)0-1
S
(O)0-1
N
# k * * O
, L2b ,
R9 R8 R7 O
0-1(O) R8 R7 O
0-1(O) S S
S N # NR4
# k *
N k *
# *
O O
L2c , L2d , and L2e ;
wherein, k is an integer ranging from 0 to 4; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10; wherein, in Formula I when R1 is CF ;
3 A is phenyl ring or C3-C7 carbocyclic ring or 5- to 6- membered heterocyclic ring; L2 is L2c and k= 0 then R10 is not hydrogen, cyano, nitro, C1- C3alkyl, C1-C3 haloalkyl;;
wherein, in Formula I when R1 is CF3; A is phenyl ring or 5- to 6- membered heteroaromatic ring L2 is L2d and k= 0 to 4 then R10 is not cyano, nitro, R11 and OR11; wherein, R11 is hydrogen, C1-C6-alkyl optionally substituted with a group selected from halogen, cyano, nitro, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and phenyl ring optionally substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6- haloalkoxy,
R2, R3, R2a, R3a, R2b, R3b, R2c, R3c, R2d, R3d, R2e, R3e, R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, or
R2 and R3; R2a and R3a; R2b and R3b; R2c and R3c; R2d and R3d; R2e and R3e; and or R7 and R8 together with the atoms to which they are attached may form 3- to 5- membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;
R9 is independently selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rh independently represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C3- C8-cycloalkyl; (C=O)-Ri, wherein, Ri represents hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-
alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy; C1-8-alkyl-S(O)0-2Rj, wherein Rj represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl; C1-C6-alkyl-(C=O)-Ri, CRi=NRg, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C5-C8-cycloalkynyl, C7-C19-aralkyl, bicyclic C5-C12-alkyl, C7-C12-alkenyl, fused or non-fused or bicyclic C3-C18-carbocyclic; wherein one or more carbon atoms in cyclic ring system may be replaced by N, O, S(=O)0-2, S(=O)0-1(=NR6c), C(=O), C(=S), C(=CR2eR3e) and C=NR6c,
wherein, R9 may optionally be substituted with one or more identical or different substituents selected from hydrogen, halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6- alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1- C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6- alkylamino, di- C1-C6-alkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6- alkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, or di C1-C6- alkylaminocarbonyloxy, 5- to 11- membered spirocyclic ring, 3- to 6- membered carbocyclic or heterocyclic ring;
R10 is selected from the group of hydrogen, halogen, hydroxy, cyano, -OR12, -NR13R14, nitro, -SH, -SCN, -COR15, -C(=O)OR12, -C(=O)NR13R14, -NR13C(=O)R15, -O(C=O)R15, -O(C=O)NR13R14, -C(=NOR13)R15, -NR13SO2R16, -CSR16, -C(=S)OR12, -C(=S)NR13R14, -NR13C(=S)R15, -O(C=S)R15, -O(C=S)NR13R14, -O(C=S)SR16, -N=C(R15)2, -NHCN, -SO2NHCN, -C(=O)NHCN, -C(=S)NHCN, -C(=S(O))NHCN, -SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di- C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 or Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(=CR2dR3d) or S(O)0-2; Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered
heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17; or
Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15- membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non- aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(=CR2cR3c) or C(=NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
wherein, R17 is selected from hydrogen, halogen, hydroxy, cyano, -OR12, -NR13R14, nitro, -SH, -SCN, -COR15, -C(=O)OR12, -C(=O)NR13R14, -NR13C(=O)R15, -O(C=O)R15, -O(C=O)NR13R14, -C(=NOR13)R15, -NR13SO2R16, -CSR16, -C(=S)OR12, -C(=S)NR13R14, -NR13C(=S)R15, -O(C=S)R15, -O(C=S)NR13R14, -O(C=S)SR16, -N=C(R15)2, -NHCN, -SO2NHCN, -C(=O)NHCN, -C(=S)NHCN, -C(=S(O))NHCN, -SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-
cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di- C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 or Z2Q2;
R9 and R10; and or or R9 and RA together with the atoms to which they are attached may form a 3- to 10- membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
wherein,
R12 represents C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl,
R13 and R14 independently represent hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl,
R15 represents hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-cycloalkyl, and
R16 represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6- haloalkoxy, C3-C8-cycloalkyl, or C3-C8-cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof. The compound claimed in claim 1, wherein; a carbon atom of R1 from the oxadiazole ring bears at least two fluorine atoms; and the b carbon atom of R1 from the oxadiazole ring in case of C2-haloalkyl bears at least one fluorine atom.
The compound claimed in claim 1,
wherein:
R1 is trifluoroalkyl;
L1 is a direct bond;
A is a phenyl ring or pyridyl ring; wherein phenyl or pyridyl ring is unsubstituted or substituted with one or more identical or different RA groups,
wherein, RA is halogen, cyano, C1-C6-alkyl and C1-C6- wherein RA may be optionally substituted with one
from halogen, cyano, and amino;
R9 R7 R8 R9 R7 R8 O
S O N
S # k * k
N
* O
L2 is a fragment selected from the group of L2a , L2b ,
R9
O
R9 R8 R7 R8 O
R7 O
O S S N
S # NR4
# k * *
N k *
# O O
L2c , L2d , and L2e ;
wherein, k is an integer ranging from 0 to 1; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10; R7 and R8 are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, or C1-C4-alkoxy;
R9 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, and C3-C8-cycloalkyl;
R10 is selected from the group of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl or Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, and O;
Q1 and Q2 are phenyl, benzyl, 5- or 6-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein the heteroatom of the heteroaromatic ring is selected from N, O and S; and each ring may be optionally substituted with one or more substituents independently selected from R17; or
wherein, R17 is selected from halogen, cyano, -OR12; wherein R12 represents C1-C6-alkyl, C1- C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl; C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8- cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl and Z2Q2;
R9 and R10 together with the atoms to which they are attached may form a 3- to 10- membered heterocyclic ring or ring system which may be optionally substituted with R17; wherein the heteroatom of the heterocyclic ring or ring system is selected from N, O and S(O)0-2.
The compound of Formula 1 as claimed in claim 1, is selected from the group consisting of N-(methyl(oxo)(p-tolyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,3-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxybenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-bromobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(2-methylbenzyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-
oxadiazol-3-yl)benzamide; N-((3,5-dimethylphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxidotetrahydro-2H-1l6-thiopyran-1-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(m-tolyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(3-methylbenzyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(thiazol-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(4-(trifluoromethyl)benzyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-dichlorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-ylmethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(4-methylthiazol-2-yl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(5-methyl-1,3,4-thiadiazol-2-yl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-dichlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-dimethoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3,4-difluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)benzamide; N-(methyl(oxo)(pyridin-4-ylmethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chloro-3-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(4-(trifluoromethyl)phenyl)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(phenyl)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxybenzyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(thiazol-2-yl)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxidotetrahydro-2H-1l6-thiopyran-1-ylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorophenyl)(isopropyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(4-methoxyphenyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(isopropyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(oxo)(phenyl)- l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-bromophenyl)(ethyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(2-phenoxyethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; (2,6-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,6-difluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,4-difluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,3-difluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(2-methylbenzyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-(trifluoromethyl)benzyl)-l6-sulfanone; (2,6-dichlorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-bromobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(pyridin-2-ylmethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (3-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,4-dimethoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (3,4-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-chlorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-chloro-3-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (3-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; 1-((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)hexahydro-1l6-thiopyran 1-oxide; (2,4-dimethoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (3-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,5-dichlorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; methyl(phenyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; methyl(pyridin-2-yl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (2,6-difluorobenzyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (4-chlorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(pyridin-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(m-tolyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(thiazol-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-(trifluoromethyl)pyridin-2-yl)-l6-sulfanone; methyl(4-methylthiazol-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(thiazol-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-chlorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (2,6-difluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (3,4-difluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-fluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; methyl((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)(4-(trifluoromethyl)phenyl)- l6-sulfanone; (2-fluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (4-fluorobenzyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; (3-methoxyphenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-l6-sulfanone; 1-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)hexahydro-1l6-thiopyran 1-oxide; 4-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-1,4l6-oxathiane 4-oxide; methyl(p-tolyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2,4-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(5-(trifluoromethyl)pyridin-2-yl)-l6-sulfanone; 4-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-1,4l6-oxathiane 4-oxide; 1-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)hexahydro-1l6-thiopyran 1-oxide; methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(p-tolyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2,4-dimethoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (3,4-difluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)(4-((4-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)-l6-sulfanone; (4-chlorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(thiazol-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (4-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2-bromo-5-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; 4-fluoro-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)benzenesulfonamide; (4-bromo-2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; 4-((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-1,4l6-oxathiane 4-oxide; isopropyl(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; isopropyl(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (4-chlorophenyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; N-tosyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((5-chloro-2-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-dichlorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((4-(trifluoromethyl)phenyl)sulfonyl)benzamide; N-(pyridin-3-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-difluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-bromophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-dichlorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl)-l6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(phenyl)-l6-sulfanone; (4-chlorophenyl)((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-l6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(pyridin-2-yl)-l6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(3-
fluorophenyl)(methyl)-l6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-fluorophenyl)(methyl)-l6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(methyl)-l6-sulfanone; 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 3-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 3-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 4-chloro-2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 2-chloro-6-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)-2-phenylacetamide; 4-chloro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)pivalamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)cyclopropanecarboxamide; ((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((4-fluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((2,4-difluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((3-fluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; N-((4-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide; ((2,4-difluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((2-fluoro-4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((2-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(methyl)-l6-sulfanone; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(phenyl)-l6-sulfanone; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(pyridin-2-yl)-l6-sulfanone; ((2-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorobenzyl)(trifluoromethyl)-l6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(trifluoromethyl)-l6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(trifluoromethyl)-l6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(phenyl)(trifluoromethyl)-l6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(pyridin-2-yl)(trifluoromethyl)-l6-sulfanone; ((3-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((4-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; ((5-methoxypyridin-2-yl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; (2-(dimethylamino)ethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (2-(dimethylamino)ethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2,4-difluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (2-fluoro-4-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (2-fluoro-4-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2-fluorobenzyl)((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-l6-sulfanone; (2-fluorobenzyl)((3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-l6-sulfanone; (2-fluorobenzyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-fluorobenzyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-l6-sulfanone; (2-fluorobenzyl)(methyl)((5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-l6-sulfanone; (2-fluorobenzyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-fluorophenyl)((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-l6-sulfanone; (2-fluorophenyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-l6-sulfanone; (2-fluorophenyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (2-methoxyethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (2-methoxyethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (2-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (3-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (3-fluoropyridin-4-yl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (3-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (3-methoxypyridin-4-yl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (3-methoxypyridin-4-yl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (4-(difluoromethyl)phenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (4-fluoro-2-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (4-fluoro-2-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (4-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-l6-sulfanone; (4-methoxyphenyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (cyclobutylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; (cyclobutylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (cyclobutylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (cyclohexylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; (cyclopentylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; (cyclopentylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (cyclopentylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (cyclopropylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; (cyclopropylmethyl)(2-fluorobenzyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (cyclopropylmethyl)(2-fluorophenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone;
(cyclopropylmethyl)(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (cyclopropylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; (cyclopropylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; (cyclopropylmethyl)(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (cyclopropylmethyl)(pyridin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; (furan-3-ylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; 1-methyl-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)-1H-imidazole-4-carboxamide; 1-methyl-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)-1H- imidazole-5-carboxamide; 2,4-difluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 2-fluoro-4-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 2-fluoro-N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 2-methoxy-N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((trifluoromethyl)sulfonyl)benzamide; 4-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 4-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)benzamide; 5-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)picolinamide; allyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; allyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; allyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; cyclopentyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; cyclopropyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; cyclopropyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; cyclopropyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; isobutyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; isobutyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; isobutyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; isopropyl(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; isopropyl(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; isopropyl(pyridin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl((1-methyl-1H-imidazol-4-yl)imino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl((1-methyl-1H-imidazol-5-yl)imino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(oxazol-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(oxazol-4-yl)((4- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(oxazol-5-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(oxazol-5-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(oxazol-5-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(perfluoroethyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(perfluoroethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(phenyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(phenyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-l6-sulfanone; methyl(phenyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-l6-sulfanone; methyl(phenylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(prop-2-yn-1-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(prop-2-yn-1-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(prop-2-yn-1-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; methyl(pyridin-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(pyridin-2-yl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-l6-sulfanone; methyl(pyridin-2-yl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-l6-sulfanone; methyl(pyridin-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(pyridin-3-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(pyridin-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone;
methyl(pyrimidin-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(pyrimidin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(pyrimidin-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(pyrimidin-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(pyrimidin-4-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(pyrimidin-4-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(thiazol-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(thiazol-4-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(thiazol-5-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(thiazol-5-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(thiazol-5-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(thiophen-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(thiophen-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(thiophen-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(thiophen-3-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(thiophen-3-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; methyl(thiophen-3-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfanone; methyl(trifluoromethyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-l6-sulfanone; methyl(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-l6-sulfanone; N-(((1-methylazetidin-3-yl)methyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-(dimethylamino)ethyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-(dimethylamino)ethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-(dimethylamino)ethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-fluoro-4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((2-fluorobenzyl)(methyl)(oxo)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((2-fluorobenzyl)(oxo)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((2-fluorophenyl)(oxo)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyethyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-methoxyethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-fluoropyridin-4-yl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-methoxypyridin-4-yl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-(difluoromethyl)phenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(cyclopropylmethyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((4-chlorophenyl)(oxo)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluoro-2-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-
methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((4-methoxyphenyl)(oxo)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclobutylmethyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclobutylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclobutylmethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopentylmethyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclopropylmethyl)(2-fluorobenzyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(2-fluorophenyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(4-methoxyphenyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclopropylmethyl)(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((oxetan-3-ylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((perfluoroethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxido-1l6-thietan-1-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(1-oxidotetrahydro-1l6-thiophen-1-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(1-oxidotetrahydro-2H-1l6-thiopyran-1-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(4-oxido-1,4l6-oxathian-4-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(4-oxido-1,4l6-oxathian-4-ylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(4-oxido-1,4l6-oxathian-4-ylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(4-oxido-1,4l6-oxathian-4-ylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(allyl(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(allylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(allylsulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopentyl(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopropyl(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(cyclopropyl(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopropylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(ethylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutyl(methyl)(oxo)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(isobutyl(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutylsulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(methyl)(oxo)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)cyclobutanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)cyclohexanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)cyclopentanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)furan-3-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)oxazole-5-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)picolinamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)pyrimidine-2-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)pyrimidine-4-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-
1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)thiazole-5-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)thiophene-2-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-l6-sulfaneylidene)thiophene-3-carboxamide; N-(methyl(oxo)(perfluoroethyl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(phenyl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(prop-2-yn-1-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(prop-2-yn-1-yl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(propyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(pyridin-2-yl)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(methyl(oxo)(pyridin-3-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(methyl(oxo)(pyrimidin-2-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyrimidin-4-yl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(trifluoromethyl)-l6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(oxo(pyridin-2-yl)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(oxo(pyridin-4-yl)(trifluoromethyl)-l6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(prop-2-yn-1-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(propylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((trifluoromethyl)sulfonyl)benzamide; N-methyl-N-(((1-methylazetidin-3-yl)methyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-((oxetan-3-ylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-((perfluoroethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-(prop-2-yn-1-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; phenyl(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone; and pyridin-2-yl(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-l6-sulfanone.
A combination comprising a compound of Formula I claimed in claim 1 and at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients.
A composition comprising at least one compound of Formula I claimed in claim 1 and at least one agrochemically acceptable auxiliary.
The composition according to claim 6, further comprising at least one pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients.
A composition comprising at least one compound of Formula I claimed in claim 1 and seed, wherein the amount of the compound of Formula I claimed in claim 1, is from 0.1 gai to 10 kgai per 100 kg of seeds.
A method for controlling or preventing phytopathogenic fungi, wherein the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of compound of formula I claimed in claim 1 or the combination claimed in claim 5 or the composition claimed in claims 6-7.
A method for controlling or preventing infestation of plants by phytopathogenic micro-organisms in agricultural crops, floricultural crops and or horticultural crops wherein an effective amount of compound of formula I claimed in claim 1 or the combination claimed in claim 5 or the composition claimed in claims 6-7, is applied to the seeds of plants.
. Use of the compound claimed in claim 1, the combinations claimed in claim 5 and the composition claimed in claims 6-7 for controlling or preventing plant diseases.
. Use as claimed in claim 11, wherein the plant diseases are selected from Puccinia spp. (rusts), comprising P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) and P. recondita (brown or leaf rust) on cereals viz., wheat, barley or rye; and Phakopsora spp. comprising Phakopsora pachyrhizi and P. meibomiae on soybeans, Hemileia vastatrix (Coffee rust), Uromyces spp., comprising U fabae (rust of beans).
. A process for preparing prising at least one of the steps selected
a. esterifying a com
pound of formula 1 into a compound of formula 2 using suitable esterifying reactant and reagent:
R7R8
R7R8 C1-C6 alkyl
NC
L1 A ( )k OH ( )k O
NC A O L1
O
1 2 ;
b. convert e in the presenc und of formula
R7R8 NH
( ) 2OH R7R8
k L1
NC A OH H2N A ( )k OH L1
O N O HO
c. cyclizing pound of formula ompound of formul
O O R7R8 C1-C6 alkyl
R7R8 8 N L1
A ( )k O
O
d. hydrolyz
R7R8 C1-C6 alkyl R7R8
N L1 N L1
A ( )k O A ( )k OH
O O N O N O
R1 R1
4 5 ; and e. reacting the compound of formula 5 and a compound of formula 6 to obtain the compound of formula I:
R1
R1 I
,
O O
wherein, L2 is L2b or L2e ; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10;
or
f. reacting a compound of formula 6 with a compound of formula 7 to obtain a compound of formula Ia:
Ia
7 ;
*
wherein, L2 is L2a ; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10;
g. converting the compound of formula Ia by reacting with hydroxyl amine hydrochloride into a compound of form
NC A R10
N HO
Ia Ib ;
*
wherein, L2 steps f to is L2a
; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10; and
h. cyclizing the compound of formula Ib and a compound of formula 8 to obtain a compound of formula I:
R1CO(OH)
I
;
*
wherein, L2 is L2a
; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10; or
i. reacting a compound of formula 9 with ammonium carbamate to obtain a compound of formula 10:
Ammonium
NC A carbamate
L1 S
O
R9 R9
9 10
;
j. reacting the compound of formula 10 with a compound of formula 11 to obtain a compound of formula Ia:
Ia
10 ;
#
wherein, L2 is L2c
; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10;
k. reacting the compound of formula Ia with hydroxyl amine hydrochloride to obtain a compound of for
N
I HO
Ib ;
#
wherein, L2 is L2c
; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10; and
l. cyclizing the compound of formula Ib and the compound of formula 8 to obtain the compound of formula I:
1
HO
I ;
#
wherein, L2 is L2c
; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10;
or
m. imidizing the compound of formula 9 to obtain a compound of formula 11:
A
A NH2OH.HCl H2N L1 S
L1 S
NC R9
R9 N
HO
9 11 ;
n. cyclizing the compound of formula 11 with the compound of formula 8 to obtain a compound of formula 12:
R1CO(OH)
or
R1 O R1
O N A H R1
2N L1 S O O A
8 N L1 S
R9
N R9
HO
11 12
;
o. reacting the compound of formula 12 with ammonium carbamate to obtain a compound of formula 13:
Ammonium
O N carbamate O N
R1 A R1
N L1 N A
L1 NH
S S O
R9 R9
12 13 ; and
p. reacting the compound of formula 13 with a compound of formula 14 to obtain the compound of formula I:
R8 7
R8 7 R
R Cl ( )
HO ( ) k 10
k R
R10
or O
O N O O N
R1 14 R1
H R1
N A N A 0
L1 S N L1 L2
O
R9 I
13
R9
0-1(O) R8 R7
S
N
# k *
O
wherein, L2 is L2d ; an expression“#” on the left side indicates the point of attachment to A, and an expression“*” on the right side indicates the point of attachment to R10;
wherein, R1, L1, A, R7, R8, R9 and R10 are as defined in claim 1.
. Compounds of Formulae Ia and Ib;
OH N NC A R10
A R10
L1 L2
H2N L1 L2
Ia , and Ib , wherein L1, A, L2, R10 are as defined in claim 1.
| Section | Controller | Decision Date |
|---|---|---|
| # | Name | Date |
|---|---|---|
| 1 | 202017033946-IntimationOfGrant05-03-2024.pdf | 2024-03-05 |
| 1 | 202017033946-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [07-08-2020(online)].pdf | 2020-08-07 |
| 2 | 202017033946-PatentCertificate05-03-2024.pdf | 2024-03-05 |
| 2 | 202017033946-STATEMENT OF UNDERTAKING (FORM 3) [07-08-2020(online)].pdf | 2020-08-07 |
| 3 | 202017033946-Written submissions and relevant documents [29-02-2024(online)].pdf | 2024-02-29 |
| 3 | 202017033946-PRIORITY DOCUMENTS [07-08-2020(online)].pdf | 2020-08-07 |
| 4 | 202017033946-FORM 1 [07-08-2020(online)].pdf | 2020-08-07 |
| 4 | 202017033946-Correspondence to notify the Controller [12-02-2024(online)].pdf | 2024-02-12 |
| 5 | 202017033946-US(14)-ExtendedHearingNotice-(HearingDate-14-02-2024).pdf | 2024-01-25 |
| 5 | 202017033946-DECLARATION OF INVENTORSHIP (FORM 5) [07-08-2020(online)].pdf | 2020-08-07 |
| 6 | 202017033946-Written submissions and relevant documents [11-01-2024(online)].pdf | 2024-01-11 |
| 6 | 202017033946-COMPLETE SPECIFICATION [07-08-2020(online)].pdf | 2020-08-07 |
| 7 | 202017033946-FORM 3 [22-10-2020(online)].pdf | 2020-10-22 |
| 7 | 202017033946-Correspondence to notify the Controller [26-12-2023(online)].pdf | 2023-12-26 |
| 8 | 202017033946-FORM-26 [28-10-2020(online)].pdf | 2020-10-28 |
| 8 | 202017033946-Correspondence to notify the Controller [22-12-2023(online)].pdf | 2023-12-22 |
| 9 | 202017033946-FORM-26 [22-12-2023(online)].pdf | 2023-12-22 |
| 9 | 202017033946-Proof of Right [30-11-2020(online)].pdf | 2020-11-30 |
| 10 | 202017033946-FORM 3 [14-01-2021(online)].pdf | 2021-01-14 |
| 10 | 202017033946-US(14)-ExtendedHearingNotice-(HearingDate-27-12-2023).pdf | 2023-12-22 |
| 11 | 202017033946-US(14)-HearingNotice-(HearingDate-26-12-2023).pdf | 2023-11-23 |
| 11 | 202017033946.pdf | 2021-10-19 |
| 12 | 202017033946-CLAIMS [19-08-2022(online)].pdf | 2022-08-19 |
| 12 | 202017033946-Power of Attorney-051120.pdf | 2021-10-19 |
| 13 | 202017033946-FER_SER_REPLY [19-08-2022(online)].pdf | 2022-08-19 |
| 13 | 202017033946-OTHERS-120121.pdf | 2021-10-19 |
| 14 | 202017033946-Correspondence-120121.pdf | 2021-10-19 |
| 14 | 202017033946-OTHERS [19-08-2022(online)].pdf | 2022-08-19 |
| 15 | 202017033946-Correspondence-051120.pdf | 2021-10-19 |
| 15 | 202017033946-FORM 3 [18-08-2022(online)].pdf | 2022-08-18 |
| 16 | 202017033946-FORM 18 [17-12-2021(online)].pdf | 2021-12-17 |
| 16 | 202017033946-FORM-26 [18-08-2022(online)].pdf | 2022-08-18 |
| 17 | 202017033946-Information under section 8(2) [18-08-2022(online)].pdf | 2022-08-18 |
| 17 | 202017033946-FER.pdf | 2022-02-21 |
| 18 | 202017033946-FER.pdf | 2022-02-21 |
| 18 | 202017033946-Information under section 8(2) [18-08-2022(online)].pdf | 2022-08-18 |
| 19 | 202017033946-FORM 18 [17-12-2021(online)].pdf | 2021-12-17 |
| 19 | 202017033946-FORM-26 [18-08-2022(online)].pdf | 2022-08-18 |
| 20 | 202017033946-Correspondence-051120.pdf | 2021-10-19 |
| 20 | 202017033946-FORM 3 [18-08-2022(online)].pdf | 2022-08-18 |
| 21 | 202017033946-Correspondence-120121.pdf | 2021-10-19 |
| 21 | 202017033946-OTHERS [19-08-2022(online)].pdf | 2022-08-19 |
| 22 | 202017033946-FER_SER_REPLY [19-08-2022(online)].pdf | 2022-08-19 |
| 22 | 202017033946-OTHERS-120121.pdf | 2021-10-19 |
| 23 | 202017033946-CLAIMS [19-08-2022(online)].pdf | 2022-08-19 |
| 23 | 202017033946-Power of Attorney-051120.pdf | 2021-10-19 |
| 24 | 202017033946.pdf | 2021-10-19 |
| 24 | 202017033946-US(14)-HearingNotice-(HearingDate-26-12-2023).pdf | 2023-11-23 |
| 25 | 202017033946-FORM 3 [14-01-2021(online)].pdf | 2021-01-14 |
| 25 | 202017033946-US(14)-ExtendedHearingNotice-(HearingDate-27-12-2023).pdf | 2023-12-22 |
| 26 | 202017033946-FORM-26 [22-12-2023(online)].pdf | 2023-12-22 |
| 26 | 202017033946-Proof of Right [30-11-2020(online)].pdf | 2020-11-30 |
| 27 | 202017033946-Correspondence to notify the Controller [22-12-2023(online)].pdf | 2023-12-22 |
| 27 | 202017033946-FORM-26 [28-10-2020(online)].pdf | 2020-10-28 |
| 28 | 202017033946-Correspondence to notify the Controller [26-12-2023(online)].pdf | 2023-12-26 |
| 28 | 202017033946-FORM 3 [22-10-2020(online)].pdf | 2020-10-22 |
| 29 | 202017033946-COMPLETE SPECIFICATION [07-08-2020(online)].pdf | 2020-08-07 |
| 29 | 202017033946-Written submissions and relevant documents [11-01-2024(online)].pdf | 2024-01-11 |
| 30 | 202017033946-DECLARATION OF INVENTORSHIP (FORM 5) [07-08-2020(online)].pdf | 2020-08-07 |
| 30 | 202017033946-US(14)-ExtendedHearingNotice-(HearingDate-14-02-2024).pdf | 2024-01-25 |
| 31 | 202017033946-FORM 1 [07-08-2020(online)].pdf | 2020-08-07 |
| 31 | 202017033946-Correspondence to notify the Controller [12-02-2024(online)].pdf | 2024-02-12 |
| 32 | 202017033946-Written submissions and relevant documents [29-02-2024(online)].pdf | 2024-02-29 |
| 32 | 202017033946-PRIORITY DOCUMENTS [07-08-2020(online)].pdf | 2020-08-07 |
| 33 | 202017033946-STATEMENT OF UNDERTAKING (FORM 3) [07-08-2020(online)].pdf | 2020-08-07 |
| 33 | 202017033946-PatentCertificate05-03-2024.pdf | 2024-03-05 |
| 34 | 202017033946-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [07-08-2020(online)].pdf | 2020-08-07 |
| 34 | 202017033946-IntimationOfGrant05-03-2024.pdf | 2024-03-05 |
| 1 | Search-337E_18-02-2022.pdf |
| 1 | SearchHistory-337-convertedE_18-02-2022.pdf |
| 2 | Search-337E_18-02-2022.pdf |
| 2 | SearchHistory-337-convertedE_18-02-2022.pdf |