Pesticidal Active Heterocyclic Derivatives with Sulfur-Containing Substituents - Patent application

Abstract

Formula (I) JPEG2026503577000083.jpg26160 (wherein the substituents are as defined in claim 1) Compound. Furthermore, the present invention relates to pesticidal compositions comprising compounds of formula (I), to the preparation of these compositions and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling animal pests, including arthropods and in particular insects, mollusks, nematodes or representatives of the order Acarina.

Description

[Technical Field]

[0001] The present invention relates to pesticidally active, in particular insecticidally active, heterocyclic derivatives containing sulfur substituents, processes for their preparation, compositions containing these compounds and their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina. [Background technology]

[0002] Pesticidal active heterocyclic derivatives having sulfur-containing substituents are described, for example, in WO 2012 / 012086848, WO 2013 / 018928, WO 2019 / 131575, WO 2020 / 174094. Summary of the Invention [Problem to be solved by the invention]

[0003] It has now surprisingly been found that certain novel pesticidally active heterocyclic dihydro-naphthyridinone derivatives having sulfur-containing substituents have favourable properties as pesticides. [Means for solving the problem]

[0004] The present invention therefore provides a compound of formula I [ka] (In the formula, G1 is CR 2a or N, R2 is halogen, C1-C6 haloalkyl, C1-C4 haloalkylsulfanyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyloxy or C3-C6 cycloalkyloxy; R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-; Q is a group of the formulas Qa, Qb, Qc, Qd and Qe [ka] is a group selected from the group consisting of wherein the arrow represents the point of attachment to the nitrogen atom of the bicyclic or tricyclic ring; and A represents CH or N; X is S, SO, or SO; R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, -N(R4)2, -N(R4)C(=O)R5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to a ring containing substituent A, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; and said ring system may contain 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein said ring system may not contain more than one ring oxygen atom and may not contain more than one ring sulfur atom; or Q1 is a 5-membered aromatic ring system linked via a ring nitrogen atom to a ring containing substituent A, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; and said ring system containing 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein said ring system contains at least one ring nitrogen atom and may not contain more than one ring oxygen atom and may not contain more than one ring sulfur atom; R3 is hydrogen, halogen, or C1-C4 alkyl; each R4 is independently hydrogen, C1-C4 alkyl, or C3-C6 cycloalkyl; R5 is C1-C6 alkyl, C1-C6 haloalkyl or C3-C6 cycloalkyl; R6 is C1-C4 alkyl, R7 is hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, -CO(NR4)2, -NR4COR5, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl monosubstituted with cyano-C1-C6 alkyl, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or R7 is a 5-6 membered saturated, partially saturated or aromatic ring system linked via a ring nitrogen atom to the imidazole ring containing the substituent R6, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; C3-C6 cyclo alkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl monosubstituted with cyano-C1-C6 alkyl, wherein the ring system contains 1, 2 or 3 ring heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and the ring system contains at least one ring nitrogen atom and may contain no more than one ring oxygen atom and may contain no more than one ring sulfur atom; or R7 is a 5-6 membered saturated, partially saturated or aromatic ring system linked via a ring carbon atom to the imidazole ring containing the substituent R6, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; C3-C6 cyclohexane C1-C6 cycloalkyl monosubstituted with cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, (C3-C6)cycloalkyl-(C1-C6)alkyl-, (C3-C6)cycloalkyl monosubstituted with cyano-(C1-C6)alkyl-, wherein the ring system may contain 1, 2 or 3 ring heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and the ring system may not contain more than one ring oxygen atom or more than one ring sulfur atom; R8 and R9 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R4)2 or -N(R4)C(=O)R5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or R8 and R9 are, independently of each other, hydrogen or a 5- to 6-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring carbon atom, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl, said ring system may contain 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, said ring system may not contain more than one ring oxygen atom and more than one ring sulfur atom, and one of R8 or R9 is hydrogen; or R8 and R9 are each independently hydrogen or a 5-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring nitrogen atom, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl, said ring system containing 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, said ring system containing at least one ring nitrogen atom and optionally containing no more than one ring oxygen atom and no more than two ring sulfur atoms, and one of R8 or R9 is hydrogen; R 10 and R 11are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R4)2 or -N(R4)C(=O)R5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, or R 10 and R 11 are each independently hydrogen or a 5- to 6-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring carbon atom, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl, said ring system may contain 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and said ring system may not contain more than one ring oxygen atom and more than one ring sulfur atom, R 10 or R 11 is hydrogen; or R 10 and R 11 are, independently from each other, hydrogen or a 5-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring nitrogen atom, said ring system being unsubstituted or mono- or polysubstituted with substituents independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl, said ring system containing 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, said ring system containing at least one ring nitrogen atom and optionally containing no more than one ring oxygen atom and no more than one ring sulfur atom; R 10 or R 11one of which is hydrogen) to provide a compound of formula (I).

[0005] The present invention also provides agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of compounds of formula I. DETAILED DESCRIPTION OF THE INVENTION

[0006] The compounds of formula I having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, for example, perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphorus-containing acids, hydrohalic acids, etc.; with strong organic carboxylic acids, for example, unsubstituted or halogen-substituted C1-C4 alkane carboxylic acids, such as acetic acid; saturated or unsaturated dicarboxylic acids, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, phthalic acid, etc.; hydroxycarboxylic acids, for example, ascorbic acid, lactic acid, malic acid, tartaric acid, citric acid, or benzoic acid; or with organic sulfonic acids, for example, unsubstituted or halogen-substituted C1-C4 alkane or aryl sulfonic acids, for example, methane or p-toluenesulfonic acid. Compounds of formula I having at least one acidic group can, for example, form salts with bases, for example mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl, diethyl, triethyl or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0007] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example in agriculturally usable salt form.

[0008] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic compounds, as described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0009] The compounds of formula I according to the present invention also include the hydrates which may be formed during salt formation.

[0010] When substituents themselves are described as being further substituted, this means that they have one or more of the same or different substituents, for example, 1 to 4 substituents. Typically, no more than three such optional substituents are present at the same time. Preferably, no more than two such substituents are present at the same time (i.e., the group is substituted with one or two of the listed substituents). When the additional substituent is a larger group such as cycloalkyl or phenyl, it is most preferred that only one of such optional substituents is present. When one group is described as being substituted (e.g., alkyl), this includes those groups that are part of other groups (e.g., alkyl in alkylthio).

[0011] As used herein, "C1-C n The term "alkyl" means a saturated straight or branched hydrocarbon group having 1 to n carbon atoms and bonded by any carbon atom, such as any one of methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0012] As used herein, "C1-C n The term "haloalkyl" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms bonded via any of the carbon atoms (as defined above), in which some or all of the hydrogen atoms may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, It is one of 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl. Thus, the term "C1-C2-fluoroalkyl" refers to a C1-C2-alkyl group having 1, 2, 3, 4 or 5 fluorine atoms, such as any one of difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.

[0013] As used herein, "C1-C nThe term "alkoxy" refers to a straight or branched saturated alkyl group having 1 to n carbon atoms attached via an oxygen atom (as defined above), i.e., any one of methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0014] As used herein, "C1-C n The term "haloalkoxy" refers to any of the above C1-C alkyl groups partially or fully substituted with fluorine, chlorine, bromine and / or iodine. n alkoxy groups, i.e., for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, or 4-bromobutoxy.

[0015] As used herein, "C1-C nThe term "alkylsulfanyl" refers to any one of a linear or branched saturated alkyl group (as defined above) having 1 to n carbon atoms attached via a sulfur atom, i.e., methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, or 1,1-dimethylethylthio.

[0016] As used herein, "C1-C n The term "alkylsulfinyl" refers to any one of the linear or branched saturated alkyl groups (as defined above) having 1 to n carbon atoms bonded via the sulfur atom of a sulfinyl group, i.e., for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethyl-sulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl or 1-ethylpropylsulfinyl.

[0017] As used herein, "C1-C n The term "alkylsulfonyl" refers to any one of a linear or branched saturated alkyl group (as defined above) having 1 to n carbon atoms attached through the sulfur atom of a sulfonyl group, i.e., for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, or t-butylsulfonyl.

[0018] As used herein, "C1-C n The term "haloalkylsulfanyl" refers to any of the above C1-C alkyls which are partially or fully substituted with fluorine, chlorine, bromine and / or iodine. nIt refers to an alkylthio group, such as, for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloro propylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, or 4-bromobutylthio.

[0019] "C1~C n Haloalkylsulfinyl" and "C1-C n The term "haloalkylsulfonyl" refers to the above groups but with sulfur in the 1 or 2 oxidation states, respectively.

[0020] As used herein, "C1-C n The term "haloalkylsulfonyloxy" refers to a C1-C alkyl group bonded through an oxygen atom. n refers to haloalkylsulfonyl (as defined above).

[0021] As used herein, "C1-C nThe term "cyanoalkyl" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms substituted by a cyano group (as defined above), such as cyanomethylene, cyanoethylene, 1,1-dimethylcyanomethyl, cyanomethyl, cyanoethyl, and 1-dimethylcyanomethyl.

[0022] As used herein, the term "C3-C6 cycloalkyl" refers to 3- to 6-membered cycloylalkyl groups such as cyclopropane, cyclobutane, cyclopropane, cyclopentane, and cyclohexane.

[0023] The suffix "-C1-C" following a term such as "C3-C6 cycloalkyl" n "Alkyl" (e.g., where n in the suffix is ​​an integer from 2 to 6), as used herein, refers to a straight-chain or branched saturated alkyl group substituted with a C3-C6 cycloalkyl. An example of a C3-C6 cycloalkyl-(C1-C6)alkyl is, for example, cyclopropylmethyl. An example of a C3-C6 cycloalkyl monosubstituted with a cyano-(C1-C6)alkyl is cyanocyclopropylmethyl.

[0024] The term "C3-C6 cycloalkyloxy" as used herein refers to a C3-C6 cycloalkyl group (as defined above) attached through an oxygen atom.

[0025] Halogen is generally fluorine, chlorine, bromine or iodine. This also applies equally to halogen in combination with other meanings, such as haloalkyl.

[0026] In the present invention, Q1 or R7 to R 11 The term "mono- or poly-substituted" in the definition of a substituent typically means mono- to penta-substituted, more preferably mono-, doubly or triply substituted, depending on the chemical structure of the substituent.

[0027] In the context of the present invention, Q, R, R, R as "a 5- to 6-membered aromatic ring system... linked via ring carbon atoms" 10 or R 11 Examples of are phenyl, pyrazolyl, triazolyl, pyridinyl and pyrimidinyl, preferably phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidin-2-yl, pyrimidin-4-yl and pyrimidin-5-yl.

[0028] In the context of the present invention, Q, R as "a five-membered aromatic ring system linked via a ring nitrogen atom..." 8、 R9, R 10 or R 11 Examples of are pyrazolyl, pyrrolyl, imidazolyl and triazolyl, preferably pyrrol-1-yl, pyrazol-1-yl, triazol-2-yl, 1,2,4-triazol-1-yl, triazol-1-yl and imidazol-1-yl.

[0029] As used herein, the phrase "R7 is a 5-6 membered saturated, partially saturated, or aromatic ring system linked through a ring nitrogen atom..." is exemplified by imidazolyl, imidazolinyl, isothiazolidinyl, isothiazolinyl, isoxazolidinyl, isoxazolinyl, morpholinyl, oxazolidinyl, oxazolinyl, phenyl, piperazinyl, piperidinyl, pyrazolinyl, pyrrolidinyl, pyrrolinyl, pyrazolyl, pyrrolyl, thiazinyl, thiazolidinyl, thiazolinyl, thiomorpholinyl, and triazolyl, preferably pyrrol-1-yl, pyrazol-1-yl, triazol-2-yl, 1,2,4-triazol-1-yl, triazol-1-yl, and imidazol-1-yl.

[0030] As used herein, the phrase "R7 is a 5-6 membered saturated, partially saturated, or aromatic ring system linked via a ring carbon atom..." includes cyclohexadienyl, cyclohexenyl, cyclopentenyl, dihydrofuranyl, dihydropyranyl, dihydrothienyl, dihydrothiopyranyl, imidazolinyl, isothiazolidinyl, isothiazolinyl, isoxazolidinyl, isoxazolinyl, morpholinyl, oxathiolanyl, oxazolidinyl, oxazolinyl, phenyl ... Exemplary are perazinyl, piperidinyl, pyranyl, pyrazolinyl, pyrazolyl, pyrrolidinyl, pyrrolinyl, pyridinyl, pyrimidinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiopyranyl, thiazinyl, thiazolidinyl, thiazolinyl, thiolanyl, thiomorpholinyl, thiopyranyl and triazolyl, preferably phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidin-2-yl, pyrimidin-4-yl and pyrimidin-5-yl.

[0031] Certain embodiments of the present invention are provided as described below.

[0032] Embodiment 1 provides a compound of Formula I, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, as defined above.

[0033] In embodiment 2, Q is Qa, and G1, R2, R 2a , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein preferred values ​​of A, X, R1, Q1, R3, R4, and R5, in any of their combinations, are as set forth below: Preferably, G1 is N or G1 is CR 2a where R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-, G1 is CR 2a It is also preferable if It is also preferred that G1 is CH, Most preferably, G1 is N; Preferably, R2 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyl or C1-C4 haloalkylsulfonyloxy, C3-C6 cycloalkoxy or halogen, or G1 is CR 2a If R 2a together with the --O--CF2--O-- group, It is also preferred that R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, More preferably, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, halogen, cyclopropyloxy, -OCH2CF2Cl-, OCH2CF2CF2H, -OCH2CF2CF3, -OCH2CCl2CF3, -OCH2CCl3 or CF3; Most preferably, R2 is CF3 or OCF3; Preferably, A is N or CH; Most preferably, A is N; Preferably, X is S or SO; Most preferably, X is SO; Preferably, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; More preferably, R1 is ethyl or cyclopropylmethyl; Most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, such as hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy; It is also preferred that Q1 is a 5-6 membered aromatic ring system linked via a ring carbon atom to the ring containing the substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms, for example phenyl, which may be monosubstituted with halogen or C-linked pyrimidinyl, It is also preferred that Q1 is a 5-membered aromatic ring system linked via a ring nitrogen atom to a ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system is an N-linked pyrazolyl or N-linked triazolyl containing two or three ring nitrogen atoms and which may be monosubstituted, for example, by chloro, cyano or trifluoromethyl; More preferably, Q1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro, cyano or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl; Even more preferably, Q1 is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, —NH(CH3), —N(CH3)COCH3, —N(CH3)COCH2CH3, —N(CH3)CO(cyclopropyl), —N(H)CONH(CH3), —N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyanopyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; Most preferably, Q1 is 1-cyanocyclopropyl.

[0034] Preferably, each R4 is independently hydrogen or C1-C4 alkyl; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl; Preferably, R3 is hydrogen or C1-C4 alkyl; More preferably, R3 is hydrogen or methyl; and Most preferably, R3 is hydrogen.

[0035] In embodiment 3, Q is Qb, and G1, R2, R 2a , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein preferred values ​​of A, X, R1, Q1, R3, R4, and R5, in any of their combinations, are as set forth below: Preferably, G1 is N or G1 is CR 2a where R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-, G1 is CR 2a It is also preferable if It is also preferred that G1 is CH, Most preferably, G1 is N; Preferably, R2 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyl or C1-C4 haloalkylsulfonyloxy, C3-C6 cycloalkoxy or halogen, or G1 is CR 2a If R 2a together with the --O--CF2--O-- group, It is also preferred that R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, More preferably, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, halogen, cyclopropyloxy, -OCH2CF2Cl, -OCH2CF2CF2H, -OCH2CF2CF3, -OCH2CCl2CF3, -OCH2CCl3 or CF3; Most preferably, R2 is CF3; Preferably, A is N or CH; Most preferably, A is N; Preferably, X is S or SO; Most preferably, X is SO; Preferably, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; More preferably, R1 is ethyl or cyclopropylmethyl; Most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, such as hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy; It is also preferred that Q1 is a 5-6 membered aromatic ring system linked via a ring carbon atom to the ring containing the substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms, for example phenyl, which may be monosubstituted with halogen or C-linked pyrimidinyl, It is also preferred that Q1 is a 5-membered aromatic ring system linked via a ring nitrogen atom to a ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, cyano and C1-C4 haloalkyl; and said ring system is an N-linked pyrazolyl or N-linked triazolyl containing two or three ring nitrogen atoms and which may be monosubstituted, for example, by chloro, cyano or trifluoromethyl; More preferably, Q1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro, cyano or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl; Even more preferably, Q1 is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, —NH(CH3), —N(CH3)COCH3, —N(CH3)COCH2CH3, —N(CH3)CO(cyclopropyl), —N(H)CONH(CH3), —N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyanopyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; Most preferably, Q1 is 1-cyanocyclopropyl.

[0036] Preferably, each R4 is independently hydrogen or C1-C4 alkyl; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl; Preferably, R3 is hydrogen or C1-C4 alkyl; More preferably, R3 is hydrogen or methyl; and Most preferably, R3 is hydrogen.

[0037] In embodiment 4, Q is Qc, and G1, R2, R 2a , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein preferred values ​​of X, R1, R4, R5, R5, and R6, in any of their combinations, are as set forth below: Preferably, G1 is N or G1 is CR 2a where R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-, G1 is CR 2a It is also preferable if It is also preferred that G1 is CH, Most preferably, G1 is N; Preferably, R2 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyl or C1-C4 haloalkylsulfonyloxy, C3-C6 cycloalkoxy or halogen, or G1 is CR 2a If R 2a together with the --O--CF2--O-- group, It is also preferred that R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, More preferably, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, halogen, cyclopropyloxy, -OCH2CF2Cl, -OCH2CF2CF2H, -OCH2CF2CF3, -OCH2CCl2CF3, -OCH2CCl3 or CF3; Most preferably, R2 is CF3; Preferably, X is S or SO; Most preferably, X is SO; Preferably, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; More preferably, R1 is ethyl or cyclopropylmethyl; Most preferably, R1 is ethyl; Preferably, R6 is C1-C4 alkyl, Most preferably, R6 is methyl; Preferably, R7 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, or -N(R4)CON(R4)2; It is also preferred that R7 is a 5-membered aromatic ring system linked via a ring nitrogen atom to the imidazole ring containing the substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms, It is also preferred that R7 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to an imidazole ring containing the substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl and C3-C6 cyclopropyl monosubstituted with cyano, said ring system optionally containing one or two ring nitrogen atoms; More preferably, R7 is N-linked pyrazolyl optionally monosubstituted with hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoroethoxy, chloro, or trifluoromethyl, or R7 is N-linked triazolyl, C-linked pyrimidinyl, phenyl optionally monosubstituted with halogen, trifluoromethyl, cyclopropyl, or cyano-cyclopropyl; or R7 is -N(R4)2, -N(R4)COR5, or -N(R4)CON(R4)2, where each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl; Most preferably, R7 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, 4-fluorophenyl, 4-chlorophenyl, 4-cyclopropyl-phenyl, 4-(cyano-cyclopropyl)-phenyl, Preferably, each R4 is independently hydrogen or C1-C4 alkyl; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl.

[0038] In embodiment 5, Q is Qd and G, R, R 2a , X, R1, R 4、10. A compound according to embodiment 1, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein preferred values ​​of R5, R8, and R9, in any of these combinations, are as set forth below: Preferably, G1 is N or G1 is CR 2a where R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-, It is also preferred that G1 is CH, Most preferably, G1 is N; Preferably, R2 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyl or C1-C4 haloalkylsulfonyloxy, C3-C6 cycloalkoxy or halogen, or G1 is CR 2a If R 2a together with the --O--CF2--O-- group, It is also preferred that R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, More preferably, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, halogen, cyclopropyloxy, -OCH2CF2Cl, -OCH2CF2CF2H, -OCH2CF2CF3, -OCH2CCl2CF3, -OCH2CCl3 or CF3; Most preferably, R2 is CF3; Preferably, X is S or SO; Most preferably, X is SO; Preferably, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; More preferably, R1 is ethyl or cyclopropylmethyl; Most preferably, R1 is ethyl; Preferably, R8 and R9 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, -N(R4)2, -N(R4)C(=O)R5 or -N(R4)CON(R4)2, wherein each R4 is independently hydrogen or methyl, and R5 is methyl, ethyl or cyclopropyl; It is also preferred that R8 and R9 are each independently hydrogen or a 5-6-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring carbon atom, said ring system being unsubstituted or monosubstituted with halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl and C3-C6 cyclopropyl monosubstituted with cyano, said ring system may contain one or two ring nitrogen atoms, wherein one of R8 or R9 is hydrogen, and the other of R8 or R9 is said 5-6-membered aromatic ring system; It is also preferred that R8 and R9 are each independently hydrogen or a 5-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl, said ring system containing 2 or 3 ring nitrogen atoms, one of R8 or R9 being hydrogen, and the other of R8 or R9 being said 5-membered aromatic ring system; It is further preferred that R8 and R9 are each independently hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; It is further preferred if R8 and R9 independently of one another are H, F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, when R8 is H and R9 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl; or when R8 is H; It is further preferred if R9 is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl; when R9 is H and R8 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl; or when R9 is H; It is further preferred if R8 is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, More preferably, R8 and R9 are each independently hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy or C1-C6 haloalkoxy; Even more preferably, R8 and R9 are each independently hydrogen, iodo, bromo, chloro, trifluoromethyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy; Most preferably, R8 is hydrogen and R9 is trifluoromethyl; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl.

[0039] In embodiment 6, Q is Qe and G1, R2, R 2a , X, R1, R 4、 10. A compound according to embodiment 1, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein preferred values ​​of R5, R8, and R9, in any of these combinations, are as set forth below: Preferably, G1 is N or G1 is CR 2a where R 2a is hydrogen or R 2a together with R2 form the group -O-CF2-O-, It is also preferred that G1 is CH, Most preferably, G1 is N; Preferably, R2 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 haloalkylsulfonyl or C1-C4 haloalkylsulfonyloxy, C3-C6 cycloalkoxy or halogen, or G1 is CR 2a If R 2a together with the --O--CF2--O-- group, It is also preferred that R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, More preferably, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, halogen, cyclopropyloxy, -OCH2CF2Cl, -OCH2CF2CF2H, -OCH2CF2CF3, -OCH2CCl2CF3, -OCH2CCl3 or CF3; Most preferably, R2 is CF3; Preferably, X is S or SO; Most preferably, X is SO; Preferably, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; More preferably, R1 is ethyl or cyclopropylmethyl; Most preferably, R1 is ethyl; Preferably, R 10 and R 11 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, -N(R4)2, -N(R4)C(=O)R5, or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl; R 10 and R 11 are each independently hydrogen or a 5- to 6-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring carbon atom, said ring system being unsubstituted or monosubstituted by halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl, and C3-C6 cyclopropyl monosubstituted by cyano, said ring system may contain one or two ring nitrogen atoms, wherein R 10 or R 11 is hydrogen and R 10 or R 11 the other is the 5- to 6-membered aromatic ring system; R 10 and R 11 are each independently hydrogen or a 5-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl, said ring system containing 2 or 3 ring nitrogen atoms, R 10 or R 11 is hydrogen and R 10 or R 11 the other is said 5-membered aromatic ring system; R 10and R 11 are each independently hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl; R 10 and R 11 are further preferred when, independently of one another, they are H, F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, R 10 is H and R 11 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, where each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl, or R 10 is H and R 11is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, R 11 is H and R 10 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, where each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl, or R 11 is H and R 10 is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, More preferably, R 10 and R 11are each independently hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy or C1-C6 haloalkoxy; Even more preferably, R 10 and R 11 are each independently hydrogen, iodo, bromo, chloro, trifluoromethyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy; Most preferably, R 10 is hydrogen and R 11 is trifluoromethyl, Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl.

[0040] Further embodiments according to the invention are provided as described below.

[0041] A preferred group of compounds of formula I is the compound of formula I-A1 [ka] wherein A, R1, R2, R3, X, Q1, R4 and R5 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-A1.

[0042] In one preferred group of compounds of formula I-A1, A is CH or N, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl, R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, R3 is hydrogen or C1-C4 alkyl, X is S or SO2, Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, where each R4 is independently hydrogen or C1-C4 alkyl, and R5 is C1-C6 alkyl or C3-C6 cycloalkyl.

[0043] In another preferred group of compounds of formula I-A1, A is CH or N, R1 is ethyl or cyclopropylmethyl, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3, R3 is hydrogen or methyl, X is S or SO2 and Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy.

[0044] In another more preferred group of compounds of formula I-A1, Q1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, for example, Q1 is phenyl which may be monosubstituted with halogen, or Q1 is C-linked pyrimidinyl, more preferably Q1 is C-linked pyrimidinyl.

[0045] Also preferred are compounds of formula I-A1 in which Q1 is a 5-membered aromatic ring system linked to the ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, for example, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro, cyano, or trifluoromethyl, or Q1 is N-linked triazolyl; more preferably, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro or trifluoromethyl, or Q1 is N-linked triazolyl.

[0046] In all of the compounds of formula I-A1 and preferred embodiments of compounds of formula I-A1 above, unless otherwise specified, A, R1, R2, R3, X, Q1, R4, and R5 are as defined under formula I above, preferably A is CH or N, more preferably A is N, preferably R1 is ethyl or cyclopropylmethyl, most preferably R1 is ethyl, preferably R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, or CF3, most preferably R2 is CF2CF3 or C F3, preferably X is S or SO2, most preferably X is SO2, preferably R3 is hydrogen, and preferably Q1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked phenyl optionally monosubstituted with chloro, cyano or trifluoromethyl. and R is independently either hydrogen or methyl, and R is either methyl, ethyl, or cyclopropyl; more preferably, Q is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-di ... Fluoropropoxy, -NH(CH), -N(CH)COCH, -N(CH)COCHCH, -N(CH)CO(cyclopropyl), -N(H)CONH(CH), -N(CH)CONH(CH), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0047] One further preferred group of compounds according to this embodiment is preferably wherein A is N, preferably wherein R1 is ethyl or cyclopropylmethyl, most preferably wherein R1 is ethyl, preferably wherein R2 is SO2CF3, -OCF3, CF2CF3 or CF3, most preferably wherein R2 is CF2CF3 or CF3, preferably wherein X is S or SO2, most preferably wherein X is SO2, preferably wherein R3 is hydrogen; preferably wherein Q1 is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, 2-pyridyl Compounds of formula (I-A1-1) are compounds of formula (I-A1), which are N-linked pyrazolyl optionally monosubstituted with lysyloxy, chloro, or trifluoromethyl, or -N(R4)COR5, where R4 is hydrogen and R5 is either methyl or ethyl, and more preferably, Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, -N(CH3)COCH3, 2-pyridyloxy, 3-chloro-pyrazol-1-yl, or 3-trifluoromethyl-pyrazol-1-yl. Most preferably, Q1 is 1-cyanocyclopropyl.

[0048] Another preferred group of compounds of formula I is the compound of formula I-A2 [ka] wherein A, R1, R2, R3, X, Q1, R4 and R5 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-A2.

[0049] In one preferred group of compounds of formula I-A2, A is CH or N, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl, R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, R3 is hydrogen or C1-C4 alkyl, X is S or SO2, Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, where each R4 is independently hydrogen or C1-C4 alkyl, and R5 is C1-C6 alkyl or C3-C6 cycloalkyl.

[0050] In another preferred group of compounds of formula I-A2, A is CH or N, R1 is ethyl or cyclopropylmethyl, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3, R3 is hydrogen or methyl, X is S or SO2 and Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy.

[0051] In another more preferred group of compounds of formula I-A2, Q1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, for example, Q1 is phenyl which may be monosubstituted with halogen, or Q1 is C-linked pyrimidinyl, more preferably Q1 is C-linked pyrimidinyl.

[0052] Also preferred are compounds of formula I-A2 in which Q1 is a 5-membered aromatic ring system linked to the ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, for example, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro, cyano, or trifluoromethyl, or Q1 is N-linked triazolyl; more preferably, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro or trifluoromethyl, or Q1 is N-linked triazolyl.

[0053] In all of the compounds of formula I-A2 and preferred embodiments of compounds of formula I-A2 above, unless otherwise specified, A, R1, R2, R3, X, Q1, R4, and R5 are as defined under formula I above, preferably A is CH or N, more preferably A is N, preferably R1 is ethyl or cyclopropylmethyl, most preferably R1 is ethyl, preferably R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3, or CF3, most preferably R2 is CF2CF3 or C F3, preferably X is S or SO2, most preferably X is SO2, preferably R3 is hydrogen, and preferably Q1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked phenyl optionally monosubstituted with chloro, cyano or trifluoromethyl. and R is independently either hydrogen or methyl, and R is either methyl, ethyl, or cyclopropyl; more preferably, Q is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-di ... Fluoropropoxy, -NH(CH), -N(CH)COCH, -N(CH)COCHCH, -N(CH)CO(cyclopropyl), -N(H)CONH(CH), -N(CH)CONH(CH), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0054] A further preferred group of compounds according to this embodiment preferably has A=N; preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; preferably, R2 is SO2CF3, -OCF3, CF2CF3 or CF3; most preferably, R2 is CF2CF3 or CF3; preferably, X is S or SO2; most preferably, X is SO2; preferably, R3 is hydrogen; and preferably, Q1 is hydrogen, cyclopropyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)C. OR or -N(R)CON(R), each of which R is independently hydrogen or methyl, and R is methyl, ethyl, or cyclopropyl; more preferably, Q is hydrogen, cyclopropyl, -NH(CH), -N(CH)COCH, -N(CH)COCHCH, -N(CH)CO(cyclopropyl), -N(CH)CONH(CH), 1,2,4-triazol-1-yl, or pyrimidin-2-yl. Most preferably, Q is 1-cyanocyclopropyl.

[0055] Another preferred group of compounds of formula I is the compound of formula I-A3 [ka] wherein R1, R2, X, R4, R5, R6 and R7 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-A3.

[0056] In one preferred group of compounds of formula I-A3, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, X is S or SO2, and R6 is C1-C4 alkyl; Preferably, R7 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, or -N(R4)CON(R4)2; Also preferred is where R7 is a 5-membered aromatic ring system linked via a ring nitrogen atom to an imidazole ring containing substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing 2 or 3 ring nitrogen atoms.

[0057] It is also preferred that R7 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to an imidazole ring containing substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl, and C3-C6 cyclopropyl monosubstituted with cyano, and said ring system may contain 1 or 2 ring nitrogen atoms.

[0058] More preferably, R7 is N-linked pyrazolyl optionally monosubstituted by hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoroethoxy, chloro or trifluoromethyl, or R7 is N-linked triazolyl, C-linked pyrimidinyl, phenyl optionally substituted by halogen, trifluoromethyl, cyclopropyl or cyanocyclopropyl; or R7 is -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl, preferably R5 is methyl.

[0059] Most preferably, R7 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl, 4-fluorophenyl, 4-chlorophenyl, 4-cyclopropyl-phenyl, 4-(cyano-cyclopropyl)-phenyl.

[0060] In another preferred group of compounds of formula I-A3, R1 is ethyl or cyclopropylmethyl; R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3; X is S or SO2; and R7 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy.

[0061] In another further preferred group of compounds of formula I-A3, R7 is also preferred as a 5- to 6-membered aromatic ring system linked via a ring carbon atom to the imidazole ring containing the substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl, and C3-C6 cyclopropyl monosubstituted with cyano, and said ring system may contain one or two ring nitrogen atoms. In this embodiment, R7 is more preferably C-linked pyrimidinyl, 4-fluorophenyl, 4-chlorophenyl, 4-cyclopropylphenyl, and 4-(cyanocyclopropyl)phenyl.

[0062] Also preferred are compounds of formula I-A3 in which R7 is a 5-membered aromatic ring system linked via a ring nitrogen atom to an imidazole ring containing substituent R6, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, more preferably, R7 is N-linked pyrazolyl, which may be monosubstituted with chloro or trifluoromethyl; or R7 is N-linked triazolyl.

[0063] In all of the compounds of formula I-A3 and preferred embodiments of compounds of formula I-A3 above, unless otherwise specified, R, R, X, R, R, R, R and R are as defined under formula I above, preferably R is ethyl or cyclopropylmethyl, most preferably R is ethyl, preferably R is -OSOCF, SOCF, -OCF, CFCF or CF, most preferably R is CFCF or CF, preferably X is S or SO; most preferably X is SO, preferably R is methyl, preferably R is C-linked pyrimidinyl, 4-fluorophenyl, 4-chloro-phenyl, 4-cyclo-propyl-phenyl and 4-(cyano-cyclopropyl)-phenyl or N-linked triazolyl.

[0064] Another preferred group of compounds of formula I is the compound of formula I-A4 [ka] wherein R1, R2, R4, R5, R8 and R9 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-A4.

[0065] In one preferred group of compounds of formula I-A4, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl, R2 is C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, and X is S or SO2; Preferably, R8 and R9 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, -N(R4)2, -N(R4)C(=O)R5 or -N(R4)CON(R4)2, wherein each R4 is independently hydrogen or methyl, and R5 is methyl, ethyl or cyclopropyl; More preferably, R8 and R9 are each independently hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy or C1-C6 haloalkoxy; Most preferably, R8 and R9 are each independently hydrogen, iodo, bromo, C1-C3 haloalkyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl.

[0066] In another preferred group of compounds of formula I-A4, R8 and R9 are each independently hydrogen or a 5- to 6-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring carbon atom, which ring system is unsubstituted or monosubstituted with halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl, and C3-C6 cyclopropyl monosubstituted with cyano, and which may contain one or two ring nitrogen atoms, wherein one of R8 or R9 is hydrogen and the other of R8 or R9 is the 5- to 6-membered aromatic ring system. In this embodiment, for example, one of R8 or R9 is hydrogen and the other of R8 or R9 is C-linked pyrimidinyl or phenyl, which may be monosubstituted with halogen.

[0067] In another preferred group of compounds of formula I-A4, R8 and R9 are each independently hydrogen or a 5-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring nitrogen atom, which is also preferred, and which is unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl, and which ring system contains 2 or 3 ring nitrogen atoms. In this embodiment, where one of R8 or R9 is hydrogen and the other of R8 or R9 is the 5-membered aromatic ring system, for example, one of R8 or R9 is hydrogen and the other of R8 or R9 is N-linked triazolyl or N-linked pyrazolyl which may be monosubstituted by chloro or trifluoromethyl.

[0068] In another preferred group of compounds of formula I-A4, R1 is ethyl or cyclopropylmethyl, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3; X is S or SO2, and R8 and R9 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R4)2, or -N(R4)C(=O)R5, where each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl.

[0069] In another more preferred group of compounds of formula I-A4, R8 is H and R9 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl. More preferably, R8 is H and R9 is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0070] In another more preferred group of compounds of formula I-A4, R8 is H and R9 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5 or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl and R5 is either methyl, ethyl or cyclopropyl. More preferably, R8 is H and R9 is F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0071] A further preferred group of compounds of formula I-A4 is where R8 and R9 are each independently hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2, -N(R4)COR5, or -N(R4)CON(R4)2, where each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl.

[0072] A further preferred group of compounds of formula I-A4 is when R8 and R9 are each independently H, F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0073] A further preferred group of compounds according to this embodiment are compounds of formula I-A4, wherein R8 and R9 are, independently of one another, hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, or C1-C6 haloalkoxy; preferably, R8 and R9 are, independently of one another, hydrogen, iodo, bromo, C1-C3 haloalkyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl, or C1-C6 haloalkoxy. Compounds of formula I-A4, wherein R8 and R9 are, independently of one another, hydrogen, iodo, bromo, chloro, trifluoromethyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl, or C1-C6 haloalkoxy, are even more preferred; most preferably, R8 is hydrogen and R9 is trifluoromethyl.

[0074] Another preferred group of compounds of formula I is the compound of formula I-A5 [ka] (In the formula, R1, R2, R4, R5, R 10 and R 11is as defined under formula I above), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A5.

[0075] In one preferred group of compounds of formula I-A5, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl, R2 is C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, and X is S or SO2; Preferably, R 10 and R 11 are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, -N(R4)2, -N(R4)C(=O)R5, or -N(R4)CON(R4)2, wherein each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl; More preferably, R 10 and R 11 are each independently hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy or C1-C6 haloalkoxy; Most preferably, R 10 and R 11 are each independently hydrogen, iodo, bromo, C1-C3 haloalkyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy; Most preferably, each R4 is independently hydrogen or methyl; Preferably, R5 is C1-C6 alkyl or C3-C6 cycloalkyl; More preferably, R5 is methyl, ethyl or cyclopropyl; Most preferably, R5 is methyl.

[0076] In another preferred group of compounds of formula I-A5, R 10 and R 11 are each independently hydrogen or a 5- to 6-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring carbon atom, said ring system being unsubstituted or monosubstituted by halogen, C1-C4 haloalkyl, C3-C6 cyclopropyl, and C3-C6 cyclopropyl monosubstituted by cyano, said ring system may contain one or two ring nitrogen atoms, wherein R 10 or R 11 is hydrogen and R 10 or R 11 The other is the 5- or 6-membered aromatic ring system. 10 or R 11 is hydrogen and R 10 Or the other of R11 is C-linked pyrimidinyl or phenyl which may be monosubstituted with halogen.

[0077] In another preferred group of compounds of formula I-A5, R 10 and R 11 are each independently hydrogen or a 5-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl, said ring system containing 2 or 3 ring nitrogen atoms, R 10 or R 11 is hydrogen and R 10 or R 11 and the other is the five-membered aromatic ring system. 10 or R 11 is hydrogen and R 10 or R 11The other is an N-linked triazolyl or an N-linked pyrazolyl which may be monosubstituted by chloro or trifluoromethyl.

[0078] A further preferred group of compounds of formula I-A5 are those in which R 10 and R 11 are each independently hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R)2, —N(R)COR5, or —N(R)CON(R)2, wherein each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl.

[0079] A further preferred group of compounds of formula I-A5 are those in which R 10 and R 11 are independently from one another H, F, Cl, Br, I, -CF3, 2,2,2-trifluoroethoxy, -NH(CH3), -NHCOCH3, -NHCOCH2CH3, -NHCOcycloC3, -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0080] In another preferred group of compounds of formula I-A5, R1 is ethyl or cyclopropylmethyl, R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3; X is S or SO2, And R 10 and R 11are each independently hydrogen, halogen, C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, cyano, C1-C4 alkoxy, C1-C6 haloalkoxy, -N(R4)2, or -N(R4)C(=O)R5, where each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl.

[0081] One further preferred group of compounds according to this embodiment is R 10 and R 11 are each independently hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy or C1-C6 haloalkoxy, preferably R 10 and R 11 are each independently hydrogen, iodo, bromo, C1-C3 haloalkyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy, and even more preferably R 10 and R 11 are each independently hydrogen, iodo, bromo, chloro, trifluoromethyl, cyclopropyl, cyclopropyl monosubstituted with cyano, C1-C3 cyanoalkyl or C1-C6 haloalkoxy, and most preferably R 10 is hydrogen and R 11 is trifluoromethyl.

[0082] Another preferred group of compounds of formula I is the compound of formula I-B1 [ka] wherein A, R1, R2, R3, X, Q1, R4 and R5 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-B1.

[0083] In one preferred group of compounds of formula I-B1, A is CH or N, R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl, R2 is C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 haloalkylsulfanyl, C1-C2 haloalkylsulfinyl or C1-C2 haloalkylsulfonyl, R3 is hydrogen or C1-C4 alkyl, X is S or SO2, Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy, where each R4 is independently hydrogen or C1-C4 alkyl, and R5 is C1-C6 alkyl or C3-C6 cycloalkyl.

[0084] In another preferred group of compounds of formula I-B1, A is CH or N, R is ethyl or cyclopropylmethyl, R is -OSOCF, SOCF, -OCF, CFCF or CF, R is hydrogen or methyl, X is S or SO and Q is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, -NH(CH), -N(CH)COCH, -N(CH)COCHCH, -N(CH)CO(cyclopropyl), -N(H)CONH(CH), -N(CH)CONH(CH), (oxazolidin-2-one)-3-yl or 2-pyridyloxy.

[0085] In another further preferred group of compounds of formula I-B1, Q1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, for example, Q1 is phenyl which may be monosubstituted with halogen, or Q1 is C-linked pyrimidinyl, more preferably Q1 is C-linked pyrimidinyl.

[0086] Also preferred are compounds of formula I-B1 in which Q1 is a 5-membered aromatic ring system linked to the ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, for example, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro, cyano, or trifluoromethyl, or Q1 is N-linked triazolyl; more preferably, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro or trifluoromethyl, or Q1 is N-linked triazolyl.

[0087] In the compounds of formula I-B1 and all of the preferred embodiments of the compounds of formula I-B1 above, unless otherwise specified, A, R1, R2, R3, X, Q1, R4 and R5 are as defined under formula I above, preferably A is CH or N, more preferably A is N, preferably R1 is ethyl or cyclopropylmethyl, most preferably R1 is ethyl, preferably R2 is -OSO2CF3, SO2CF3, -OCF3, CF2CF3 or CF3, most preferably R2 is OCF3 or CF 3, preferably X is S or SO2, most preferably X is SO2, preferably R3 is hydrogen, and preferably Q1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyridyl optionally monosubstituted with chloro, cyano or trifluoromethyl. and R is methyl, ethyl, or cyclopropyl; more preferably, Q is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-di ... Fluoropropoxy, -NH(CH), -N(CH)COCH, -N(CH)COCHCH, -N(CH)CO(cyclopropyl), -N(H)CONH(CH), -N(CH)CONH(CH), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0088] A further preferred group of compounds according to this embodiment preferably has A=N; preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; preferably, R2 is SO2CF3, -OCF3, CF2CF3 or CF3; most preferably, R2 is CF2CF3 or CF3; preferably, X is S or SO2; most preferably, X is SO2; preferably, R3 is hydrogen; and preferably, Q1 is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, 2-pyridyl ... N-linked pyrazolyl, which may be monosubstituted by lysyloxy, chloro or trifluoromethyl, or -N(R4)COR5, where R4 is hydrogen and R5 is either methyl or ethyl; more preferably, compounds of formula (I-B1) where Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, -N(CH3)COCH3, 2-pyridyloxy, 3-chloro-pyrazol-1-yl or 3-trifluoromethyl-pyrazol-1-yl.

[0089] Another preferred group of compounds according to this embodiment is a compound of formula (I-B1-2), where A is preferably N; preferably R is ethyl or cyclopropylmethyl; most preferably R is ethyl; preferably R is SOCF, -OCF, CFCF, or CF; most preferably R is CFCF or CF; preferably X is S or SO; most preferably X is SO; preferably R is hydrogen; preferably Q is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, 2-pyridyloxy, chloro, or trifluoromethyl monosubstituted N-linked pyrazolyl or -N(R)COR, where R is hydrogen and R is either methyl or ethyl; more preferably Q is hydrogen, 1-cyanocyclopropyl, or 1-cyano-1-methyl-ethyl. Most preferably Q is 1-cyanocyclopropyl.

[0090] Another preferred group of compounds of formula I is the compound of formula I-B2 [ka] wherein A, R1, R3, X, Q1, R4 and R5 are as defined under formula I above, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of the compound of formula I-B2.

[0091] In one preferred group of compounds of formula I-B2, A is CH or N; R1 is C1-C4 alkyl or C3-C6 cycloalkyl-C1-C4 alkyl; R3 is hydrogen or C1-C4 alkyl; X is S or SO2; Q1 is hydrogen, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl monosubstituted with cyano, C1-C6 cyanoalkyl, C1-C6 haloalkoxy, -N(R4)2, -N(R4)COR5, -N(R4)CON(R4)2, (oxazolidin-2-one)-3-yl, or 2-pyridyloxy; where each R4 is independently hydrogen or C1-C4 alkyl; and R4 is C1-C6 alkyl or C3-C6 cycloalkyl.

[0092] In another preferred group of compounds of formula I-B2, A is CH or N; R1 is ethyl or cyclopropylmethyl, R3 is hydrogen or methyl, X is S or SO2, and Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, —NH(CH3), —N(CH3)COCH3, —N(CH3)COCH2CH3, —N(CH3)CO(cyclopropyl), —N(H)CONH(CH3), —N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl or 2-pyridyloxy.

[0093] In another further preferred group of compounds of formula I-B2, Q1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to the ring containing substituent A, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system may contain one or two ring nitrogen atoms. In this embodiment, for example, Q1 is phenyl which may be monosubstituted with halogen, or Q1 is C-linked pyrimidinyl, more preferably Q1 is C-linked pyrimidinyl.

[0094] Also preferred are compounds of formula I-B2 in which Q1 is a 5-membered aromatic ring system linked to the ring containing substituent A via a ring nitrogen atom, said ring system being unsubstituted or monosubstituted with a substituent selected from the group consisting of halogen and C1-C4 haloalkyl; and said ring system containing two or three ring nitrogen atoms. In this embodiment, for example, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro, cyano, or trifluoromethyl, or Q1 is N-linked triazolyl; more preferably, Q1 is N-linked pyrazolyl which may be monosubstituted with chloro or trifluoromethyl, or Q1 is N-linked triazolyl.

[0095] In all of the preferred embodiments of the compounds of formula I-B2 and the compounds of formula I-C1 above, unless otherwise specified, A, R, R, X, Q, R, and R are as defined under formula I above, preferably A is CH or N, more preferably A is N, preferably R is ethyl or cyclopropylmethyl, most preferably R is ethyl, preferably X is S or SO, most preferably X is SO, preferably R is hydrogen, and preferably Q is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro, cyano, or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R), —N(R) )COR5 or -N(R4)CON(R4)2, where each R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; more preferably, Q1 is hydrogen, bromine, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -NH(CH3), - N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), -N(H)CONH(CH3), -N(CH3)CONH(CH3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, 4-fluorophenyl, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

[0096] A further preferred group of compounds according to this embodiment are compounds of formula (I-B2-1), which are compounds of formula (I-B2) in which A is preferably N; preferably R1 is ethyl or cyclopropylmethyl; most preferably R1 is ethyl; preferably X is S or SO2; most preferably X is SO2; preferably R3 is hydrogen; preferably Q1 is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, 2-pyridyloxy, chloro or trifluoromethyl monosubstituted N-linked pyrazolyl or -N(R4)COR5, where R4 is hydrogen and R5 is either methyl or ethyl; more preferably Q1 is hydrogen, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, -N(CH3)COCH3, 2-pyridyloxy, 3-chloro-pyrazol-1-yl or 3-trifluoromethyl-pyrazol-1-yl.

[0097] Another preferred group of compounds according to this embodiment is the compound of formula (I-B2-2), where A is preferably N; preferably R is ethyl or cyclopropylmethyl; most preferably R is ethyl; preferably X is S or SO; most preferably X is SO; preferably R is hydrogen; preferably Q is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, 2-pyridyloxy, chloro, or trifluoromethyl monosubstituted N-linked pyrazolyl or -N(R)COR, where R is hydrogen and R is either methyl or ethyl; more preferably Q is hydrogen, 1-cyanocyclopropyl, or 1-cyano-1-methyl-ethyl. Most preferably Q is 1-cyanocyclopropyl.

[0098] The compounds of the present invention may have any number of benefits, including, inter alia, advantageous levels of biological activity for protecting plants against insects or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous activity spectrum, high safety profile, improved physicochemical properties, or high biodegradability or environmental profile). In particular, it has been surprisingly found that certain compounds of formula (I) can exhibit favorable safety profiles with respect to non-target arthropods, particularly pollinators such as honeybees, colony bees, and bumblebees. Most particularly, the European honeybee (Apis mellifera).

[0099] In another aspect, the present invention provides a composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), as defined in embodiments by a compound of formula I, I-A1, I-A2, I-A3, I-A4, I-A5, I-B1, I-B2, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and optionally an adjuvant or diluent.

[0100] In a further aspect, the present invention provides a method for the control and extermination of insects, acaridae, nematodes or molluscs, which method comprises applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), as defined in any of the embodiments for a compound of formula I, I-A1, I-A2, I-A3, I-A4, I-A5, I-B1, I-B2 (above), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition as defined above.

[0101] In a further aspect, the present invention provides a method for protecting plant propagation material from attack by insects, mites, nematodes or mollusks, which method comprises treating the propagation material or the site where the propagation material is to be planted with a composition as defined above.

[0102] The process according to the present invention for preparing a compound of formula I is carried out by methods known to those skilled in the art. A compound of formula I-a3, in which X is SO and A, R, R, R, G, G, and Q are as defined under formula I above, can be prepared by oxidizing a compound of formula I-a1, in which X is S and A, R, R, R, G, G, and Q are as defined under formula I above, with a compound of formula I-a2, in which X is SO and A, R, R, R, G, G, and Q are as defined under formula I above. The reaction can be carried out using reagents such as peracids, e.g., peracetic acid and m-chloroperbenzoic acid, or hydroperoxides, e.g., hydrogen peroxide and tert-butyl hydroperoxide, or inorganic oxidants, e.g., monoperoxo-disulfate salts and potassium permanganate. Similarly, compounds of formula I-a2, where X is SO and A, R, R, R, G, G, and Q are defined under formula I above, can be prepared under similar conditions as above by oxidation of compounds of formula I-a1, where X is S and A, R, R, R, G, G, and Q are defined under formula I above. These reactions can be carried out in a variety of organic or aqueous solvents compatible with these conditions, at temperatures from below 0° C. to the boiling point of the solvent system. The conversion of compounds of formula I-a1 to compounds of formula I-a2 and I-a3 is depicted in Scheme 1a.

[0103] Scheme 1a: [ka] Similarly, as shown in Scheme 1b, compounds of formula I, wherein Q is Qb and X is SO and SO, represented by formulae I-b2 and I-b3, respectively, can be obtained by oxidation of compound I-b1, wherein Q is Qb, X is S, and A, R1, R2, R3, G1, Q1, R4 and R5 are defined under formula I.

[0104] Scheme 1b: [ka] Similarly, as shown in Scheme 1c, compounds of formula I, wherein Q is Qc and X is SO and SO, represented by formulae I-c2 and I-c3, respectively, can be obtained by oxidation of compound I-c1, wherein Q is Qc, X is S, and R, R, G, R, and R are defined under formula I.

[0105] Scheme 1c: [ka] Similarly, as shown in Scheme 1d, compounds of formula I, wherein Q is Qd and X is SO and SO, represented by formulas I-d2 and I-d3, respectively, can be obtained by oxidation of compound I-d1, wherein Q is Qd, X is S, and R, R, G, R, and R are defined under formula I.

[0106] Scheme 1d: [ka] Similarly, as shown in Scheme 1e, compounds of Formula I where Q is Qd and X is SO and SO, represented by Formulas I-e2 and I-e3, respectively, can be prepared by reacting Q with Qe, X is S, and R, R, G, R 10 and R 11 can be obtained by oxidation of the compound I-e1 of formula I as defined under formula I.

[0107] Scheme 1d: [ka] As shown in Scheme 2, compounds of formula I, wherein R2, G1 and Q are defined under formula I above, can be prepared by reacting a compound of formula VI, wherein R2 and G1 are defined under formula I above, Q is defined under formula I above, and LG1 is a halogen (or a pseudo-halogen leaving group such as triflate), with a compound of formula VII, wherein R2 and G1 are defined under formula I above, Q is defined under formula I above, and LG1 is a halogen (or a pseudo-halogen leaving group such as triflate), in a suitable solvent, such as tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, or acetonitrile, in the presence of a base, such as sodium carbonate, potassium carbonate, or cesium carbonate, or sodium hydride, at a temperature of 0 to 150°C, optionally under microwave irradiation. Alternatively, the reaction of a compound of formula VII, in which LG1 is preferably bromo, iodo or triflate, with a compound of formula VI can be carried out in the presence of a metal catalyst, such as copper(I) iodide, optionally with a ligand, such as a diamine ligand (e.g., N,N'-dimethylethylenediamine or trans-cyclohexyldiamine) or dibenzylideneacetone (dba) or 1,10-phenanthroline, at a temperature of 30 to 180°C, optionally under microwave irradiation, or with a palladium catalyst, such as palladium(II) acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) or tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, optionally in the form of the chloroform adduct) or a palladium precatalyst, such as tert-BuBrettPhos Pd G3 [(2-di-tert-butylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd G3 [(2-di-cyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, optionally in the presence of a ligand such as SPhos, t-BuBrettPhos, or Xantphos, at temperatures between 60 and 120°C, optionally under microwave irradiation.The reaction can be carried out by using a base such as sodium carbonate, potassium carbonate or cesium carbonate or potassium tert-butoxide in the presence of either of the above. The reaction can be carried out in the presence of solvents such as toluene, dimethylformamide (DMF), N-methylpyrrolidine (NMP), dimethylsulfoxide (DMSO), dioxane, tetrahydrofuran (THF) and the like, as widely described in the literature.

[0108] Compounds of formula VI, wherein R2 and G1 are defined under formula I above, are compounds of formula VI, wherein R2 and G1 are defined under formula I above, and R a Compounds of formula V, in which r is a C1-C4 alkyl group, preferably methyl or ethyl, can be prepared by reducing the nitrile group to the corresponding primary amine, followed by cyclization of the ester group. Such reduction reactions can be carried out using several sets of conditions, for example, using sodium borohydride in a polar solvent (methanol can be used). The reaction is advantageously carried out in the presence of a metal salt, for example CoCl2. Lactam formation (when the amine reacts with the adjacent ester with concomitant elimination of the alcohol) can be spontaneous under reducing conditions or can be promoted by heating.

[0109] Compounds of formula V are those in which R2 and G1 are defined above in formula I, and R a is a C1-C4 alkyl group, preferably methyl or ethyl, and C(=O)OR b can be prepared from compounds of formula IV, where R is an ester that can be selectively hydrolyzed in the presence of other ester groups. b (R) can be, for example, t-butyl (removable under acidic conditions) or benzyl (removable under catalytic reduction conditions). b as a result of the cleavage of R b Decarboxylation of compounds of formula IV where is H may be spontaneous at room temperature or may require some gentle heating.

[0110] The compound of formula IV in Scheme 2 is R bis as just defined above and R2 and G1 are as defined above in formula I, and R a is a halogen (or a pseudo-halogen leaving group such as triflate), as defined for compounds of formula IV and LG2. The reaction of compounds of formula III with compounds of formula II is carried out in the presence of a base such as sodium carbonate, potassium carbonate, or cesium carbonate or sodium hydride in a suitable solvent such as tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, or acetonitrile, optionally under microwave irradiation, at a temperature of 0-150°C.

[0111] Many compounds of formula II are commercially available or described in the literature, and many more can be accessed by analogous methods by those skilled in the art of organic synthesis.

[0112] Scheme 2: [ka] Scheme 3 shows another approach to compounds of formula I, where R2, G1 and Q are defined above under formula I. This differs from the approach previously described for accessing compounds of formula VI.

[0113] Compounds of formula VI, where R2 and G1 are defined under formula I above, can also be prepared by cyclizing the primary amide functionality of compounds of formula VIII, where R2 and G1 are defined under formula I above, to a vinyl group in the ortho position. This type of cyclization can be carried out in the presence of a base (e.g., K2CO3) in a polar aprotic solvent, such as dimethylformamide. The reaction can be preferably carried out at higher temperatures, and microwave irradiation in a closed vessel can be advantageous.

[0114] Compounds of formula VIII are those in which R and G are defined under formula I above, and R ais a C1-C4-alkyl group, preferably methyl or ethyl. The conversion of a compound of formula IX to a compound of formula VIII can be achieved by hydrolyzing the ester group and reacting with an acid (R), advantageously after activation (e.g., as an acid chloride or mixed anhydride). a can be obtained by converting the acid to a primary amide by reacting a compound of formula IX, where is hydrogen, with ammonia or its equivalent.

[0115] Compounds of formula IX are those in which R2 and G1 are defined under formula I above, and R a Compounds of formula II, in which LG is a C1-C4-alkyl group, preferably methyl or ethyl, and LG is a halogen atom capable of participating in cross-coupling reactions, such as bromine, can be accessed by a different method. a is a boronic acid functional group or derivative thereof that can be coupled under Suzuki-type conditions, or a metal derivative, such as a trialkyltin group (e.g., tributyltin), that can be coupled under Stille conditions. b In the case of compounds of formula XI, where Y is a protecting group such as trialkylsilyl (e.g., trimethylsilyl), Sonogashira reaction conditions can be applied and the protecting group Y b The various coupling conditions induced above are very common and widely used by modern organic chemists.

[0116] Access to compounds of formula II has already been discussed in Scheme 2.

[0117] Scheme 3: [ka] Scheme 4 shows another approach to compounds of formula I, where R2, G1, and Q are defined under formula I above. Compounds of formula XIV can be reacted with compounds of formula XIII at the aldehyde functionality via reductive amination. This type of reaction is commonly used in organic synthesis. Example reaction conditions include an aldehyde, an amino compound (XIV), a solvent that can be protic, such as acetic acid or an aliphatic alcohol, and a reducing agent, such as sodium cyanoborohydride. This results in a secondary amine that can be isolated and purified or cyclized in the process. Raising the temperature of the reaction medium after the reductive amination step, or isolating the intermediate amine and subjecting it to thermal treatment, can directly provide compounds of formula I with concomitant loss of the alcohol Ra-OH.

[0118] R2 and G1 are defined under Formula I above, and R a Compounds of formula XIII, in which R is a C1-C4-alkyl group, preferably methyl or ethyl, are those in which R and G are defined under formula I above and R a The compounds of formula XII can be obtained by oxidative cleavage of the olefin chain of a compound of formula XII, where R is a C1-C4-alkyl group, preferably methyl or ethyl. Various methods are commonly used for this type of transformation, one of which is ozonolysis followed by a mild reductive treatment. For ozonolysis, the reaction is best carried out in dichloromethane or a mixture of dichloromethane and methanol at low temperatures (e.g., below -50°C). Mild reducing agents that can be used after ozonolysis include, for example, dimethyl sulfide or triphenylphosphine. The compounds of formula XII can be obtained by Suzuki coupling of an aryl pinacarbonate with a compound of formula II, where R and G are as defined above under formula I, and R a is a C1-C4-alkyl group, preferably methyl or ethyl, and is also used in Schemes 2 and 3. This reaction can be carried out in THF at 70°C using cesium fluoride as the base and Pd(PPh3)4 as the catalyst.

[0119] An example of this reaction sequence can be seen in the analogous case of WO2018112842 (intermediate Q).

[0120] Scheme 4: [ka] Compounds of formula XIV, where Q is as defined above in formula I, can be prepared by deprotection (removal of the BOC group) of compounds of formula XVI, where Q is as defined above in formula I (Scheme 5).

[0121] Scheme 5: [ka] This reaction can be carried out in the presence of an acid such as, inter alia, trifluoroacetic acid, hydrochloric acid or sulfuric acid, under the conditions already mentioned above.

[0122] The compound of formula XVI (wherein Q is as defined in formula I above) can be prepared by reacting the compound of formula XV (wherein Q is as defined in formula I above) with an organic azide in the presence of a suitable base and tert-butanol (t-BuOH), in the presence of a coupling agent, optionally in the presence of a Lewis acid, and in the presence of an inert solvent, at a temperature between 50°C and the boiling point of the reaction mixture. The reaction can be carried out in the presence of a coupling agent such as T3P. Examples of organic azides include TMSN3, sodium azide, or tosyl azide, and suitable solvents can be toluene, xylene, THF, or acetonitrile. Examples of suitable Lewis acids can include, inter alia, Zn(OTf)2, Sc(OTf)2, or Cu(OTf)2.

[0123] The compound of formula XVI can also be prepared by reacting the compound of formula XV with diphenylphosphoryl azide in the presence of an organic base such as triethylamine or diisopropylethylamine, among others, in the presence of tert-butanol (t-BuOH), in an inert solvent such as a halogenated solvent, for example, dichloromethane or dichloroethane, or a cyclic ether, for example, tetrahydrofuran, at a temperature ranging from 50° C. to the boiling point of the reaction mixture. This reaction for converting a carboxylic acid to a BOC-protected amine is known to those skilled in the art and is known as the Curtius reaction, and has been reported, for example, in Org. Lett., 2005, 7, 4107-4110; Journal of Medicinal Chemistry, 49(12), 3614-3627; and 2006, J. Am. Chem. Soc., 1972, 94(17), pp. 6203-6205.

[0124] Compounds of formula XVI (wherein Q is as defined in formula I above) can also be prepared from compounds of formula XVII (wherein Q is as defined in formula I above) by the Hofmann rearrangement reaction. This reaction can be carried out in the presence of a base, for example, a metal hydroxide such as aqueous sodium hydroxide or potassium hydroxide, or an organic base such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene), in the presence of an electrophilic halogenating agent such as chlorine, bromine, or N-bromosuccinimide, at a temperature ranging from 20°C to the boiling point of the reaction mixture. This reaction is known as the Hofmann rearrangement and has been reported in the literature, for example, in Chem. Ber. 1881, 14, 2725.

[0125] Compounds of formula XVII (wherein Q is as defined in formula I above) can be prepared by reacting compounds of formula XV (wherein Q is as defined in formula I above) with ammonia (NH) or other ammonia substitutes, such as NHOH, in the presence of a carboxylic acid activating agent.

[0126] Compounds of formula XV, where Q is a group selected from the group consisting of formulas Qa and Qb, where A, Q1, R3, X and R1 are as defined in formula I above, are known, commercially available or can be prepared by one skilled in the art. In particular, the following subgroups of compounds of formula XV are known in the literature and are described below: 5-(1-cyano-1-methyl-ethoxy)-3-ethylsulfanyl-pyridine-2-carboxylic acid (CAS 2417036-66-7, described in WO 2020141136); 5-(1-cyano-1-methyl-ethyl)-3-ethylsulfanyl-pyridine-2-carboxylic acid (CAS 2225113-81-3, described in WO 2018077565); 5-(1-cyano-1-methyl-ethyl)-3-ethylsulfonyl-pyridine-2-carboxylic acid (CAS 2243224-65-7, described in WO 2018153778); 5-(1-cyanocyclopropyl)-3-ethylsulfanyl-pyridine-2-carboxylic acid (CAS 2225113-77-7, described in WO 2019234158; 5-(1-cyanocyclopropyl)-3-ethylsulfonyl-pyridine-2-carboxylic acid (CAS 1879106-82-7, described in WO 2016087265); 3-ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (CAS 1421952-02-4, described in WO 2016107831); 3-ethylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (CAS 1421953-19-6, described in Chinese Patent No. 110606828); 3-ethylsulfonyl-6-(1,2,4-triazol-1-yl)pyridine-2-carboxylic acid (CAS 2016034-28-7, described in WO 2019008115); 5-[acetyl(methyl)amino]-3-ethylsulfonyl-pyridine-2-carboxylic acid (CAS 2632239-16-6, described in WO 2021053110); 6-cyclopropyl-3-ethylsulfanyl-pyridine-2-carboxylic acid (CAS 1970134-21-4, described in WO 2016116338); 3-ethylsulfonyl-6-pyrimidin-2-yl-pyridine-2-carboxylic acid (CAS 1970134-19-0, described in WO 2016116338).

[0127] A compound of formula XV (wherein Q is a group of formula Qc, where X, R6, R7 and R1 are as defined in formula I above) may be defined as a compound of formula XV-c. [ka]

[0128] A few compounds of formula XV-c, where X is S (sulfide), are known in the literature (CAS 2234901-66-5, CAS 2236074-76-1) and are described in WO 2018130443 and WO 2018130437.

[0129] A subgroup of compounds of formula XVII (wherein Q is defined as Qa, X is SO, A is N, and R, R and Q are as defined in formula I) can be defined as compounds of formula XVII-a (Scheme 6).

[0130] Scheme 6: [ka] Compounds of formula XVII-a can be prepared, for example, by an amination reaction comprising reacting a compound of formula XVII-a1 (wherein R, R, and Q are as defined in formula I and LG is a halogen, preferably F, Br, or Cl) with ammonia or a salt thereof (such as a hydrohalide salt, preferably a hydrochloride or hydrobromide salt, or any other equivalent salt). The source of nitrogen can be ammonia (NH) itself or an ammonia equivalent, such as ammonium hydroxide (NHOH), ammonium chloride (NHCl), ammonium acetate (NHOAc), ammonium carbonate ((NH)CO), and other NH substitutes. This conversion is preferably carried out in a suitable solvent (or diluent) such as an alcohol, an amide, an ester, an ether, a nitrile, and water, particularly preferably methanol, ethanol, 2,2,2-trifluoroethanol, propanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water, or a mixture thereof, optionally in the presence of a base, at a temperature of 0 to 150°C, preferably at a temperature in the range from room temperature to the boiling point of the reaction mixture, and optionally under microwave irradiation.

[0131] Compounds of formula XVII-a1 (wherein R1, R3 and Q1 are as defined in formula I and LG4 is a halogen, preferably F, Br or Cl) can be prepared by oxidation of compounds of formula XVII-a2 (wherein R1, R3 and Q1 are as defined in formula I and LG4 is a halogen, preferably F, Br or Cl) under the conditions already described above.

[0132] Compounds of formula XVII-a2 (wherein R1, R3, and Q1 are as defined in formula I, and LG4 is a halogen, preferably F, Br, or Cl) can be prepared by reacting compounds of formula XVII-a3 (wherein R3 and Q1 are as defined in formula I, and LG4 is a halogen, preferably F, Br, or Cl) with a nitrite, such as tert-butyl nitrite t-BuONO, isoamyl nitrite, or sodium nitrite, under Sandmeyer-type reaction conditions in the presence of hydrohalic acid and a disulfide R1S-SR1 or alternatively a thiol R1SH (wherein R1 is as defined in formula I above). This transformation is preferably carried out in an inert solvent, such as acetonitrile or a halogenated solvent, such as 1,2-dichloroethane, at a temperature between 0 and 150°C, preferably between room temperature and the boiling point of the reaction mixture, optionally in the presence of a copper salt.

[0133] A subgroup of compounds of formula I, where Q is defined as Qb, where G1, R2, A, Q1, R3, X and R1 are as defined in formula I, may be defined as compounds of formula I-Qb (Scheme 7).

[0134] Scheme 7 [ka] In certain circumstances within Scheme 7, when Q1 is an optionally substituted triazole linked via a ring nitrogen atom to a ring containing group A, compounds of formula I-Qb (where X is SO or SO2) can be converted to compounds of formula XVIII-b (where G1, R2, A, R3 and R1 are as defined in formula I above, X is SO or SO2, by reaction with an optionally substituted triazole Q1-H (containing a suitable NH functionality) (XIXaa) (where Q1 is an N-linked triazolyl) in a solvent such as an alcohol (e.g., methanol, ethanol, isopropanol or a higher boiling point linear or branched alcohol), pyridine or acetic acid, optionally in the presence of an additional base such as potassium carbonate K2CO3 or cesium carbonate Cs2CO3, optionally in the presence of a copper catalyst, for example copper(I) iodide, at a temperature between 30 and 180 °C, optionally under microwave irradiation (CN bond formation). b can be prepared from a compound in which the leaving group is such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl or alkyl sulfonate such as trifluoromethanesulfonate.

[0135] In certain situations within Scheme 7, Q1 is -N(R4)C(=O)R5, -N(R4)CON(R4)2; wherein R4 and R5 are as defined in formula I, compounds of formula I-Qb (wherein X is SO or SO2) can be prepared from compounds of formula XVIII-b (wherein A, G1, R1, R2 and R3 are as defined in formula I, X is SO or SO2, and Xb is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or alkylsulfonate, such as trifluoromethanesulfonate) by reaction (CN bond formation) with a reagent Q1-H(XIXaa) equivalent to -N(R4)C(=O)R5, -N(R4)CON(R4)2 (wherein R4 and R5 are as defined in formula I). Such reactions can be carried out in the presence of a base such as potassium carbonate, cesium carbonate, or sodium hydroxide in an inert solvent such as toluene, dimethylformamide (DMF), N-methylpyrrolidine (NMP), dimethyl sulfoxide (DMSO), dioxane, or tetrahydrofuran (THF), optionally with a catalyst such as palladium(II) acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) or tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, optionally in the form of the chloroform adduct) or a palladium precatalyst such as tert-BuBrettPhos Pd G3 [(2-di-tert-butylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd G3 [(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, and optionally a ligand such as SPhos, t-BuBrettPhos, or Xantphos, are reacted in the temperature range of 60 to 120°C, optionally under microwave irradiation.

[0136] In certain circumstances within Scheme 7, when Q1 is -N(R4)2 and R4 is as defined in Formula I, compounds of Formula I-Qb (wherein X is SO or SO2) may be prepared from compounds of Formula XVIII-b (wherein A, G1, R1, R2 and R3 are as defined in Formula I, X is SO or SO2, and Xb is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkylsulfonate, such as trifluoromethanesulfonate), by reaction (CN bond formation) with a reagent Q1-H(XIXaa) equivalent to HN(R4)2, or a salt thereof (e.g., a hydrohalide, preferably a hydrochloride or hydrobromide, or a trifluoroacetate, or any other equivalent salt), where R4 is as defined in Formula I. Such reactions are generally carried out in inert solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferably methanol, ethanol, 2,2,2-trifluoroethanol, propanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, toluene, water or mixtures thereof, at temperatures between 0 and 150°C, optionally under pressure using microwave irradiation or an autoclave, optionally in the presence of a copper catalyst such as copper powder, copper(I) iodide or copper sulfate (optionally in the form of a hydrate) or mixtures thereof, optionally in the presence of a ligand such as a diamine ligand (for example N,N'-dimethylethylenediamine or trans-cyclohexyldiamine) or dibenzylideneacetone (dba) or 1,10-phenanthroline, and optionally in the presence of a base such as potassium phosphate.

[0137] The reagents HN(R4)2, HN(R4)COR5 or HN(R4)CON(R4)2, where R4 and R5 are as defined in Formula I, are known, commercially available, or can be prepared by methods known to those skilled in the art.

[0138] Alternatively, a compound of formula I-Qb (wherein A, G1, R1, R2 and R3 and X are SO or SO2) can be prepared, for example, by reacting a compound of formula XVIII-b (wherein A, G1, R1, R2 and R3 are as defined in formula I above, X is SO or SO2, and Xb is a leaving group, for example chlorine, bromine or iodine (preferably chlorine or bromine)) or an aryl or alkyl sulfonate, such as trifluoromethanesulfonate, with a compound of formula (XIX) (wherein Q1 is as defined in formula I and Y b1 is a boron-derived functional group, such as B(OH) or B(OR b1 )2(wherein, R b1 may be a C1-C4 alkyl group, or two groups OR b1 can be prepared by Suzuki reaction, which involves reacting a compound of formula (I) with a compound of formula (II) (which can combine with the boron atom to form a five-membered ring, e.g., pinacolboronic acid ester). This reaction can be catalyzed by a palladium-based catalyst, such as tetrakis(triphenylphosphine)palladium(0), (1,1'-bis(diphenylphosphino)ferrocene)dichloro-palladium-dichloromethane (1:1 complex), or chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (XPhos palladacycle), in the presence of a base, such as sodium carbonate, tripotassium phosphate, or cesium fluoride, in a solvent or solvent mixture, such as dioxane, acetonitrile, N,N-dimethylformamide, a mixture of 1,2-dimethoxyethane and water, or a dioxane / water mixture, or a toluene / water mixture, preferably under an inert atmosphere. The reaction temperature may preferably be in the range of room temperature to the boiling point of the reaction mixture, or the reaction may be carried out under microwave irradiation. Such Suzuki reactions are well known to those skilled in the art and are reviewed, for example, in J. Organomet. Chem. 576, 1999, 147-168.

[0139] Alternatively, compounds of formula I-Qb (wherein A, G1, R1, R2 and R3 and X are SO or SO2) can be prepared by the addition of a compound of formula (XIXa) (wherein Q1 is as defined above and Yb2 is a trialkyltin derivative, preferably tri-n-butyltin or trimethyltin, with a compound of formula XVIII-b (wherein A, G1, R1, R2, and R3 are as defined in formula I, X is SO or SO2, and Xb is a leaving group, such as chlorine, bromine, or iodine (preferably chlorine or bromine), or an aryl or alkylsulfonate, such as trifluoromethanesulfonate). Such a Stille reaction is typically carried out in the presence of a palladium catalyst, for example, tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) dichloride, in an inert solvent such as N,N-dimethylformamide, acetonitrile, toluene, or dioxane, optionally in the presence of an additive such as cesium fluoride or lithium chloride, or optionally in the presence of a further catalyst such as copper(I) iodide. Such Stille couplings are also well known to those skilled in the art and are described, for example, in J. Org. Chem., 2005, 70, 8601-8604, J. Org. Chem., 2009, 74, 5599-5602, and Angew. Chem. Int. Ed., 2004, 43, 1132-1136.

[0140] When Q1 is a 5-membered aromatic ring system linked to a ring containing the substituent A via a ring nitrogen atom, compounds of formula I-Qb (where A, G1, R1, R2 and R3 and X are SO or SO2) can be obtained by cleaving a heterocycle Q1-H (containing a suitable NH functional group) from a compound of formula XVIII-b (where A, G1, R1, R2 and R3 are as defined in formula I, X is SO or SO2, and Xb is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkyl sulfonate, such as trifluoromethanesulfonate). wherein Q1 is as defined above) (XIXaa) (wherein Q1 is as defined above) in the presence of a base such as potassium carbonate K2CO3 or cesium carbonate Cs2CO3, optionally in the presence of a copper catalyst, for example copper(I) iodide, with or without an additive, for example L-proline, N,N'-dimethylcyclohexane-1,2-diamine or N,N'-dimethyl-ethylene-diamine, in an inert solvent such as N-methylpyrrolidone NMP or N,N-dimethylformamide DMF, at a temperature of 30-150°C, optionally under microwave irradiation.

[0141] Oxidation of compounds of formula XVIII-b (wherein A, G1, R1, R2 and R3 are as defined in formula I, X is S and Xb is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkylsulfonate, such as trifluoromethanesulfonate) with a suitable oxidizing agent to compounds of formula XVIII-b (wherein A, G1, R1, R2 and R3 and X are SO or SO2) can be achieved under the conditions already described above.

[0142] Many compounds of formula (XIX), (XIXa) and (XIXaa) are commercially available or can be prepared by one skilled in the art.

[0143] Alternatively, compounds of formula I-Qb (wherein X is SO or SO) can be prepared from compounds of formula XVIII-b (wherein A, G1, R1, R2, and R3 and X is S (sulfide)) by the same chemistry as above but changing the order of steps (i.e., carrying out the sequence of XVIII-b (X is S) to I-Qb (X is S) via Suzuki, Stille, or C-N bond formation, followed by an oxidation step to form I-Qb (X is SO or SO)).

[0144] A subgroup of compounds of formula I, where Q is defined as Qa, where G, R, A, Q, R, X, and R are as defined in formula I, may be defined as compounds of formula I-Qa (Scheme 8). The chemical reactions previously described in Scheme 7 for accessing compounds of formula I-Qb from compounds of formula XVIII-b can be applied analogously for the preparation of compounds of formula I-Qa from compounds of formula XVIII-a (Scheme 8), where all previously described substituent definitions remain valid.

[0145] Scheme 8: [ka] A subgroup of compounds of formula I, where Q is defined as Qc, where G1, R2, X, R1, R6, and R7 are as defined in formula I, may be defined as compounds of formula I-Qc (Scheme 9). The chemical reactions previously described in Scheme 7 for accessing compounds of formula I-Qb from compounds of formula XVIII-b can be applied analogously for the preparation of compounds of formula I-Qc from compounds of formula XVIII-c (Scheme 9), where all previously described substituent definitions remain valid.

[0146] Scheme 9: [ka] Formulas (XX), (XXc) and (XXcc) (wherein each R7 is as defined in formula I and Y b1and Y b2 Many compounds of formula (wherein is as defined above in Scheme 7) are commercially available or can be prepared by one skilled in the art.

[0147] Alternatively, a compound of formula XV-c (wherein X is SO and R1, R6 and R7 are as defined in formula I above) can be converted to a compound of formula XXIV (wherein R1, R6 and R7 are as defined in formula I above) in the presence of a suitable base, for example sodium hydroxide (NaOH), lithium hydroxide (LiOH) or barium hydroxide Ba(OH) in the presence of a solvent such as ethanol, methanol, dioxane, tetrahydrofuran or water (or mixtures thereof) or under Krach-type conditions (e.g., NaCl in DMSO in the presence of water, typically at a temperature between 100°C and 160°C). x can be prepared by saponification of a C1-C6 alkyl, benzyl, or phenyl (Scheme 10).

[0148] Scheme 10: [ka] A compound of formula XXIV, wherein R6, R7, and R1 are as defined in formula I above, and Rx is C1-C6 alkyl, benzyl, or phenyl, can be reacted with a reagent of formula XXIII, XXIIIc, or XXIIICC, wherein R7 is as defined in formula I above, and Y b1 and Y b2 is as defined above in Scheme 8), to give a compound of formula XXII (where R and R are as defined above in formula I, and R x is C1-C6 alkyl, benzyl or phenyl, and X bcan be prepared from, for example, a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkylsulfonate such as trifluoromethanesulfonic acid.

[0149] A compound of formula XXII, wherein R and R are as defined above in formula I, and R x is C1-C6 alkyl, benzyl or phenyl, and X b is a leaving group such as, for example, chlorine, bromine, or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkylsulfonate such as trifluoromethanesulfonic acid, using a suitable oxidizing agent and under the conditions previously described to give a compound of formula XXI (where R and R are as defined in formula I above, and R x is C1-C6 alkyl, benzyl or phenyl, and X b can be prepared by oxidation of a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkylsulfonate such as trifluoromethanesulfonic acid.

[0150] A compound of formula XXII, wherein R and R are as defined above in formula I, and R x is C1-C6 alkyl, benzyl or phenyl, and X b is a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkylsulfonate such as trifluoromethanesulfonic acid) are known or can be prepared according to procedures found in the literature. For example, compounds of formula XXII (wherein R is ethyl, R is methyl, and X b is bromo and R x is ethyl) (CAS 2407490-49-5) is described in WO 2018130443, WO 2018130437 and WO 2020002082.

[0151] A subgroup of compounds of formula XV, where Q is Q, where R, R, X, and R are as defined in formula I, can be defined as compounds of formula XV-d (Scheme 11). Such compounds of formula XV-d are known in the literature or they can be prepared according to Scheme 11 using methods and conditions similar to those described, for example, in WO 2017 / 061497 and WO 2018 / 052136.

[0152] Scheme 11: [ka] A compound of formula XV, wherein Q is Qe, where R 10 , R 11 A subgroup of XV-e (X and R1 are as defined in formula I) can be defined as compounds of formula XV-e (Scheme 12). Such compounds of formula XV-e are known in the literature or they can be prepared according to Scheme 12, for example, using methods and conditions similar to those described in WO2019162174.

[0153] Scheme 12: [ka] Alternatively, a compound of formula XV-e, wherein R, X, R 10 , and R 11 is as defined in formula I) can be prepared according to Scheme 13 using methods and conditions similar to those described in the literature, for example in WO2009095253.

[0154] Scheme 13: [ka] A compound of formula XIV, wherein Q is Qe, where R 10 , R 11and R1 are as defined in formula I and X is SO2) is a subgroup of formula XIV-e (wherein R1, R 10 and R 11 is as defined in formula I and X is SO2 (Scheme 14). 10 and R 11 Compounds of formula I, where X is SO2, can be prepared according to Scheme 14.

[0155] Scheme 14: [ka] In Scheme 14, a compound of formula XIV-e (wherein R 10 , R 11 and R1 are as defined in formula I, and X is SO2) can be prepared by the compound of formula XXXXXI, where R 10 , R 11 and R1 are as defined in formula I, and X is SO2, via deprotection of the tert-butoxycarbonyl group. Such a reaction can be carried out in the presence of other acid catalysts, such as trifluoroacetic acid, hydrochloric acid, and optionally in the presence of a solvent such as dichloromethane, toluene, trifluorotoluene, among others. 10 , R 12 and R1 are as defined in formula I, and X is SO2), can be prepared by following a procedure similar to that described in Scheme 1, to give compounds of formula XXXXX, where R 10 , R 11 and R1 are as defined in formula I and X is S. 10 , R 11 and R1 are as defined in formula I, and X is S), can be prepared by the compound of formula XXXXVIII, where R 10 and R 11is as defined in formula I, PG1 is an amino protecting group such as acetyl, benzyl, benzoyl, and LG6 is a leaving group, preferably Cl, Br, or I, with a reagent of formula XXXXIX,R1-SH or a salt thereof, where R1 is as defined in formula I, optionally in the presence of a suitable base, such as an alkali metal carbonate, for example sodium carbonate and potassium carbonate, or an alkali metal hydride, for example sodium hydride, or an alkali metal hydroxide, for example sodium hydroxide and potassium hydroxide, or sodium or potassium tert-butoxide, in an inert solvent, preferably at a temperature of 25-120°C. Examples of solvents that can be used include ethers such as tetrahydrofuran (THF), ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, or polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidinone (NMP), dimethyl sulfoxide, etc. Examples of salts of compounds of formula XXXXIXa include compounds of the formula R1-SM(XXXXIXa) (wherein R1 is as defined above and M is, for example, sodium or potassium). Such a process for preparing a compound of formula XXXXIXa from a compound of formula XXXXIXa can be found, for example, in WO 16 / 091731.

[0156] Alternatively, this reaction of forming a compound of formula XXXXX from a compound of formula XXXXVIII using R1-SH(XXXXIX) or R1-SM(XXXXIXa) can be carried out in the presence of a palladium catalyst such as tris(dibenzylideneacetone)dipalladium(0), in the presence of a phosphine ligand such as xantphos, in the presence of a base such as N,N-diisopropylethylamine, and in the presence of an inert solvent such as xylene, at a temperature of 100-160° C., preferably 140° C., as described in Tetrahedron 2005, 61, 5253-5259. During the conversion of a compound of formula XXXXVIII to a compound of formula XXXXX, the amino protecting group PG1 is cleaved under the reaction conditions described above or can be subsequently cleaved using suitable reagents well known to those skilled in the art, for example, an acetyl protecting group can be cleaved under basic conditions using other bases, such as NaOH, KOH, CsCO, KCO, among others.

[0157] A compound of formula XXXXVIII, wherein R 10 and R 11 is as defined in formula I, PG is an amino protecting group, for example acetyl, benzyl, benzoyl, and LG is a leaving group, preferably Cl, Br, or I, optionally in the presence of a base, especially triethylamine, 4-dimethylaminopyridine, and in the presence of a solvent, such as dichloromethane, acetonitrile, toluene, tetrahydrofuran, etc., to afford a compound of formula XXXXVII, where R 10 and R 11 can be prepared by the reaction of a compound of formula XXXXVII (wherein R is as defined in formula I, PG is an amino protecting group such as acetyl, benzyl, benzoyl, and LG is a leaving group, preferably Cl, Br, or I) with di-tert-butyl decarbonate. 10 and R 11 is as defined in formula I, PG1 is an amino protecting group, for example, acetyl, benzyl, benzoyl, and LG6 is a leaving group, preferably Cl, Br, or I, can be prepared by reacting a compound of formula XXXVI (wherein R 10 and R11 is as defined in formula I and PG1 is an amino-protecting group, e.g., acetyl, benzyl, benzoyl, with a suitable halogenating reagent, such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, among others, in the presence of a solvent, such as dichloromethane, acetonitrile, tetrahydrofuran, DMF, among others. Such reactions are well known to those skilled in the art. Compounds of formula XXXVI (wherein R 10 and R 11 is as defined in formula I and PG1 is an amino protecting group such as acetyl, benzyl, benzoyl, for example, to prepare a compound of formula XXXXV, where R 10 and R 11 is as defined in Formula I) with a suitable amino protecting group reagent, for example, with acetyl chloride in the presence of pyridine.

[0158] A compound of formula XXXXV, wherein R 10 and R 11 is as defined in formula I) can be prepared by the reaction of a compound of formula XXXXIII with an aminating reagent such as, inter alia, hydroxylamine-O-sulfonic acid, O-(mesitylsulfonyl)hydroxylamine to give a compound of formula XXXXIV, where R 10 and R 11 is as defined in formula I), followed by N-amination reaction to form a compound of formula XXXXIV, where R is as defined in formula I, in the presence of a base such as sodium hydride, KOH, NaOH, potassium carbonate, cesium carbonate, among others, and in the presence of a solvent such as dichloromethane, dichloroethane, methanol, tetrahydrofuran, dimethylformamide, among others. 10 and R 11 is as defined in formula I) in two steps, including intramolecular cyclization of a compound of formula XXXXIII (wherein R 10 and R 11can be prepared from (as defined in formula I). ​​Such two-step reactions have been reported in the literature, for example as described in Tetrahedron Letters (2014), 55(43), 5963-5966.

[0159] A compound of formula XXXXIII, wherein R 10 and R 11 is as defined in formula I), upon reaction with an acetonitrile anion equivalent in the presence of a metal catalyst, gives a compound of formula XXXX, where R 10 and R 11is as defined in Formula I, and LG5 is a halogen (or a pseudohalogen leaving group such as triflate). A variety of acetonitrile anion equivalents can be used in such reactions. An example of such is tri-n-butylstannylacetonitrile, which may be coupled to compounds of formula (XXXX) under Stille reaction conditions as described by Mitiga ef. al (Chem. Lett. 1984, 15 11), or to trimethylsilylacetonitrile in the presence of a palladium catalyst such as tris(dibenzylideneacetone)dipalladium(0), XantPhos Pd G3 ([(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2'-amino-1,1'-biphenyl)]methanesulfonate palladium(II)) and a ligand such as Xantphos or P(i-Bu)3, a fluoride source such as ZnF2, in a dipolar aprotic solvent such as DMF at a temperature of 80-120°C; such reactions are also well documented in the literature, e.g. Hartwig (J. Am. Chem. Soc. 2002, 124, 9330, and J. Am. Chem. Soc. 2005, 727, 15824) (Scheme 9c). Metal cyanoacetates (XXXXIa), such as potassium cyanoacetate or sodium cyanoacetate, can also be used as acetonitrile anion equivalents, and the coupling reaction takes place in the presence of a palladium catalyst, such as [Pd2(dba)3] (tris(dibenzylideneacetone)dipalladium(0)), [Pd(allyl)Cl]2 (allylpalladium(II) chloride dimer), and in the presence of ligands such as SPhos, Xantphos, or P(i-Bu)3 or P(tert-butyl)3. Such reactions are known in the literature and are described, for example, in Angew. Chem. Int. Ed. 2011, 50, 4470-4474.

[0160] Alternatively, another method for preparing a compound of formula XXXXIII from a compound of formula XXXX comprises reacting a compound of formula XXXX (wherein R 10 and R 11 is as defined in Formula I and LG is a halogen (or a pseudohalogen leaving group such as triflate) with a reagent of Formula XXXXI where R is a C1-C6 alkyl to give a compound of Formula XXXXII where R 10 and R 11 is as described in Formula I above, and Ry is C1-C6 alkyl. Similar chemistry is described, for example, in Synthesis 2010, No. 19, 3332-3338.

[0161] Formula XXXXIII (wherein, R 10 and R 11 is as described above in formula I), can be obtained by the conversion of a compound of formula XXXXII (wherein R 10 and R 11can be prepared by saponification / decarboxylation of a compound of formula XXXXXII (as described above in Formula I, where Ry is C1-C6 alkyl). Alternatively, treatment of a compound of formula XXXXXII with a halide anion, preferably a chloride anion derived from, for example, lithium chloride or sodium chloride, in a solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or dimethyl sulfoxide (DMSO), optionally in the presence of additional water, can also produce a compound of formula XXXXIII. The reaction temperature for such a transformation (Krapko O-dealkylation / decarboxylation) is preferably in the range of 20°C to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Similar chemistry is described, for example, in Synthesis 2010, No. 19, 3332-3338.

[0162] An alternative conversion of compounds of formula XXXXIII, as seen in Scheme 14, to compounds of formula XXXXVI (both synthetic intermediates for the preparation of compounds of formula XIV-e) is shown in Scheme 15.

[0163] Formula XXXXVI (where R 10 and R 11 is as defined in formula I and PG1 is acetyl) can be prepared by the compound of formula XXXXIII (wherein R 10 and R 11 is as defined in formula I) via a four-step procedure including reaction with hydroxylamine to form a compound of formula XXXXXII, an acetylation reaction to form a compound of formula XXXXXIII, a base-catalyzed oxadiazole synthesis to form a compound of formula XXXXXIV, and finally an intramolecular cyclization / rearrangement to form a compound of formula XXXXVI. Such reactions have been reported in, for example, WO 2012146657, WO 2012146659 or the literature listed in Tetrahedron Letters (2017), 58(3), 202-205.

[0164] Scheme 15: [ka] Compounds of formula I (wherein Q is Qd, and G1, R2, R1, X, R8, and R9 are as defined in formula I above) can be defined as compounds of formula I-Qd. Such compounds of formula I-Qd can be prepared according to Scheme 16.

[0165] Scheme 16: [ka] In certain circumstances within Scheme 16, when R is —N(R)C(═O)R, and R and R are as defined in Formula I, compounds of formula I-Qd (where G, R, R, X, R, and R are as defined in Formula I, and X is SO or SO) can be converted to compounds of formula XVIII-d (where G, R, R, X, and R are as defined in Formula I, and X is SO or SO), bcan be prepared from a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkyl sulfonate such as trifluoromethanesulfonate, by reaction (CN bond formation) with a reagent R-H(XXXXXVa) equivalent to HN(R)C(=O)R, where R and R are as defined in formula I. Such reactions are carried out in an inert solvent such as toluene, dimethylformamide (DMF), N-methylpyrrolidine (NMP), dimethyl sulfoxide (DMSO), dioxane, tetrahydrofuran (THF), or the like, in the presence of a base such as potassium carbonate, cesium carbonate, sodium hydroxide, or in the presence of tris(dibenzylideneacetone)dipalladium(0), optionally in the presence of a catalyst such as palladium(II) acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) or tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, optionally in the form of the chloroform adduct), or a palladium precatalyst such as tert-BuBrettPhos Pd G3 [(2-di-tert-butylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd G3 [(2-di-cyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, optionally in the presence of a ligand such as SPhos, t-BuBrettPhos, or Xantphos, at a temperature of 60-120°C, optionally under microwave irradiation.

[0166] In certain circumstances within Scheme 16, when R is -N(R) and R is as defined in Formula I, a compound of formula I-Qd (where G, R, R, X, and R are as defined in Formula I, and X is SO or SO) can be reacted with a compound of formula XVIII-d (where G, R, R, X, and R are as defined in Formula I, and X is SO or SO), bcan be prepared from a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkylsulfonate, such as trifluoromethanesulfonate, by reaction (CN bond formation) with a reagent R8-H(XXXXXVa) equivalent to HN(R4)2, or a salt thereof (e.g., a hydrohalide, preferably a hydrochloride or hydrobromide, or a trifluoroacetate, or any other equivalent salt), where R4 is as defined in formula I. Such reactions are generally carried out in inert solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferably methanol, ethanol, 2,2,2-trifluoroethanol, propanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, toluene, water or mixtures thereof, at temperatures between 0 and 150°C, optionally under pressure using microwave irradiation or an autoclave, optionally in the presence of a copper catalyst such as copper powder, copper(I) iodide or copper sulfate (optionally in the form of a hydrate) or mixtures thereof, optionally in the presence of a ligand such as a diamine ligand (for example N,N'-dimethylethylenediamine or trans-cyclohexyldiamine) or dibenzylideneacetone (dba) or 1,10-phenanthroline and optionally in the presence of a base such as potassium phosphate.

[0167] The reagents HN(R4)2 or HN(R4)COR5 (wherein R4 and R5 are as defined in Formula I) are known, commercially available, or can be prepared by methods known to those skilled in the art.

[0168] Alternatively, a compound of formula I-Qd (wherein G1, R2, R1, X, R8 and R9 are as defined in formula I, and X is SO or SO2) can be prepared, for example, by the reaction of a compound of formula XVIII-d (wherein G1, R2, R1, X and R9 are as defined in formula I, and X is SO or SO2, and X bis a leaving group such as, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkyl sulfonate such as trifluoromethanesulfonate, with a compound of formula (XXXXXV) b1 is a boron-derived functional group, e.g., B(OH)2 or B(OR b1 )2(wherein, R b1 can be a C1-C4 alkyl group, or two groups OR b1 can be prepared by Suzuki reaction, which involves reacting a compound of formula (I) with a compound of formula (II) (which can combine with the boron atom to form a five-membered ring, e.g., pinacolboronic acid ester). This reaction can be catalyzed by a palladium-based catalyst, such as tetrakis(triphenylphosphine)palladium(0), (1,1'-bis(diphenylphosphino)ferrocene)dichloro-palladium-dichloromethane (1:1 complex), or chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (XPhos palladacycle), in the presence of a base, such as sodium carbonate, tripotassium phosphate, or cesium fluoride, in a solvent or solvent mixture, such as dioxane, acetonitrile, N,N-dimethylformamide, a mixture of 1,2-dimethoxyethane and water, a dioxane / water mixture, or a toluene / water mixture, preferably under an inert atmosphere. The reaction temperature may preferably be in the range of room temperature to the boiling point of the reaction mixture, or the reaction may be carried out under microwave irradiation. Such Suzuki reactions are well known to those skilled in the art and are reviewed, for example, in J. Organomet. Chem. 576, 1999, 147-168.

[0169] Formula XVIII-d (wherein G1, R2, R1, X and R9 are as defined in formula I, X is S, and X bis a leaving group, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl or alkyl sulfonate such as trifluoromethanesulfonate) with a suitable oxidizing agent to a compound of formula XVIII-d (wherein X is SO or SO) can be achieved under the conditions already described above.

[0170] Many compounds of formula (XXXXXV) and (XXXXXVa) are commercially available or can be prepared by one skilled in the art.

[0171] Alternatively, compounds of formula I (wherein X is SO or SO) can be prepared from compounds of formula XVIII-d (wherein X is S (sulfide)) with the same chemistry as above by changing the order of steps (i.e., performing the sequence of XVIII-d (wherein X is S) to Ia (wherein X is S) via Suzuki or C-N bond formation, followed by an oxidation step to form Ia (wherein X is SO or SO)).

[0172] Alternatively, compounds of formula I-Qd (wherein G1, R2, R1, X, R8 and R9 are as defined in formula I above) may be prepared according to Scheme 17.

[0173] Scheme 17: [ka] The chemical reactions previously described in Scheme 16 for accessing compounds of formula I-Qd from compounds of formula XVIII-d can be applied analogously for the preparation of compounds of formula I-Qd from compounds of formula XVIII-d (Scheme 17), where all previously described substituent definitions remain valid.

[0174] Formula I (wherein Q is Qe and G1, R2, R1, X, R 10 and R 11(wherein R is as defined in Formula I above) can be defined as compounds of formula I-Qe. Such compounds of formula I-Qe can be prepared according to Schemes 18 and 19. The chemistry described in Schemes 16 and 17 for the preparation of compounds of formula I-Qd is equally applicable to the preparation of compounds of formula I-Qe in Schemes 18 and 19.

[0175] Scheme 18: [ka]

[0176] Scheme 19: [ka] These reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide, and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0177] These reactants can react with each other as they are, i.e., without adding a solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture thereof. When the reaction is carried out in the presence of a base, a base such as triethylamine, pyridine, N-methylmorpholine, or N,N-diethylaniline, used in excess, can also serve as a solvent or diluent.

[0178] The reaction is advantageously carried out in the temperature range of about -80°C to about +140°C, preferably about -30°C to about +100°C, and often in the range of ambient temperature to about +80°C.

[0179] In conventional manner, compounds of formula I can be converted into other compounds of formula I in a manner known per se by replacing one or more substituents of the starting compound of formula I by other substituents according to the invention, and by subsequent modification of the compound by reactions such as oxidation, alkylation, reduction, acylation, and other methods known to those skilled in the art.

[0180] Depending on the reaction conditions and the choice of starting materials suitable in each case, it may, for example, only be possible in one reaction step to replace one substituent with another substituent according to the invention, or several substituents may be replaced with other substituents according to the invention in the same reaction step.

[0181] Salts of compounds of formula I can be prepared in a manner known per se: thus, for example, acid addition salts of compounds of formula I can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0182] Salts of compounds of formula I can be converted in a customary manner, for example into the free compounds I (acid addition salts) by treatment with suitable basic compounds or suitable ion exchange reagents, and can be converted into salts with bases, for example by treatment with suitable acids or suitable ion exchange reagents.

[0183] Salts of compounds of formula I can be converted into other salts (acid addition salts, e.g. other acid addition salts) of compounds of formula I in a manner known per se, for example by treating the salt of an inorganic acid, such as hydrochloric acid, with a suitable metal salt of the acid, such as sodium, barium or silver salt (e.g. silver acetate), in a suitable solvent (in which inorganic salts that form, for example, silver chloride, are insoluble and therefore precipitate from the reaction mixture).

[0184] Depending on the procedure or reaction conditions, compounds of formula I that have salt-forming properties may be available in the free form or in salt form.

[0185] The compounds of formula I and, where appropriate, their tautomers, in each free or salt form, may exist in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, such as racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or depending on the configuration of non-aromatic double bonds occurring in the molecule; the invention relates to the pure isomers and also to all possible isomeric mixtures, and is to be understood in this sense above and below, respectively, even if details of the stereochemistry are not specifically stated in each case.

[0186] Diastereomeric or racemic mixtures of compounds of formula I, in free or salt form, obtained depending on which starting materials and procedures are selected, can be separated in known manner on the basis of the physical chemical differences of the components into pure diastereomers or racemates, for example, by fractional crystallization, distillation, and / or chromatography.

[0187] Enantiomeric mixtures, such as racemates, obtainable in a similar manner can be resolved into their optical antipodes by known methods, for example recrystallization from optically active solvents, chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetylcellulose, cleavage with specific immobilized enzymes using suitable microorganisms, formation of inclusion compounds, the use of chiral crown ethers, for example, which complex with only one enantiomer, or conversion into diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, for example a carboxylic acid such as camphor, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixtures thus obtainable, for example, by fractional crystallization on account of their different solubilities, to give diastereomers from which the desired enantiomer can be liberated by the action of a suitable reagent, for example a basic reagent.

[0188] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomeric mixture, but also by generally known diastereoselective or enantioselective synthetic methods, e.g., by carrying out the process according to the invention using starting materials with the appropriate stereochemistry.

[0189] The N-oxides can be prepared by reacting the compounds of formula I with a suitable oxidizing agent, such as the H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32(12), 2561-73, 1989 or WO 2000 / 15615.

[0190] If the biological activity of the individual components differs, it may be advantageous to isolate or synthesize the respective biologically more effective isomers, e.g., enantiomers or diastereomers, or isomeric mixtures, e.g., enantiomeric or diastereomeric mixtures.

[0191] The compounds of formula I and, where appropriate, their tautomers, respectively, in free or salt form, can also be obtained, where appropriate, in the form of hydrates, and / or contain other solvents, for example solvents that may have been used for the crystallization of compounds present in solid form.

[0192] The following table shows certain compounds of the invention.

[0193] The compounds listed in Tables A-1 to A-48, B-1 to B-48, C-1 to C-48, D-1 to D-24, E-1 to E-24, F-1 to F-48, G-1 to G-48, H-1 to H-6, and J-1 to J-6 below can be prepared according to the above method. The following examples are intended to illustrate the present invention and to show preferred compounds of formula I.

[0194] The following Tables A-1 to A-48 illustrate specific compounds of the present invention. [ka]

[0195] Table A-1 provides 20 compounds A-1.001 to A-1.020 of formula I-A1a, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0196] [Table 1]

[0197] In Tables Y and A, "cycloC3" represents cyclopropyl.

[0198] For example, compound A-3.013 is [ka] is.

[0199] Table A-2 provides 20 compounds A-2.001 to A-2.020 of formula I-A1a, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0200] Table A-3 provides 20 compounds A-3.001 to A-3.020 of formula I-A1a, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0201] Table A-4 provides 20 compounds A-4.001 to A-4.020 of formula I-A1a, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0202] Table A-5 provides 20 compounds A-5.001 to A-5.020 of formula I-A1a, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0203] Table A-6 provides 20 compounds A-6.001 to A-6.020 of formula I-A1a, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0204] Table A-7 provides 20 compounds A-7.001 to A-7.020 of formula I-A1a, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0205] Table A-8 provides 20 compounds A-8.001 to A-8.019 of formula I-A1a, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0206] Table A-9 provides 20 compounds A-9.001 to A-9.020 of formula I-A1a, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0207] Table A-10 provides 20 compounds A-10.001 to A-10.020 of formula I-A1a, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0208] Table A-11 provides 20 compounds A-11.001 to A-11.020 of formula I-A1a, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0209] Table A-12 provides 20 compounds A-12.001 to A-12.020 of formula I-A1a, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0210] Table A-13 provides 20 compounds A-13.001 to A-13.020 of formula I-A1a, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0211] Table A-14 provides 20 compounds A-14.001 to A-14.020 of formula I-A1a, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0212] Table A-15 provides 20 compounds A-15.001 to A-15.020 of formula I-A1a, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0213] Table A-16 provides 20 compounds A-16.001 to A-16.020 of formula I-A1a, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0214] Table A-17 provides 20 compounds A-17.001 to A-17.020 of formula I-A1a, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0215] Table A-18 provides 20 compounds A-18.001 to A-18.020 of formula I-A1a, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0216] Table A-19 provides 20 compounds A-19.001 to A-19.020 of formula I-A1a, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0217] Table A-20 provides 20 compounds A-20.001 to A-20.020 of formula I-A1a, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0218] Table A-21 provides 20 compounds A-21.001 to A-21.020 of formula I-A1a, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0219] Table A-22 provides 20 compounds A-22.001 to A-22.020 of formula I-A1a, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0220] Table A-23 provides 20 compounds A-23.001 to A-23.020 of formula I-A1a, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0221] Table A-24 provides 20 compounds A-24.001 to A-24.020 of formula I-A1a, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0222] Table A-25 provides 20 compounds A-25.001 to A-25.020 of formula I-A1a, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0223] Table A-26 provides 20 compounds A-26.001 to A-26.020 of formula I-A1a, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0224] Table A-27 provides 20 compounds A-27.001 to A-27.020 of formula I-A1a, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0225] Table A-28 provides 20 compounds A-28.001 to A-28.020 of formula Ia-Qa, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0226] Table A-29 provides 20 compounds A-29.001 to A-29.020 of formula I-A1a, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0227] Table A-30 provides 20 compounds A-30.001 to A-30.020 of formula I-A1a, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0228] Table A-31 provides 20 compounds A-31.001 to A-31.020 of formula I-A1a, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0229] Table A-32 provides 20 compounds A-32.001 to A-32.020 of formula I-A1a, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0230] Table A-33 provides 20 compounds A-33.001 to A-33.020 of formula I-A1a, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0231] Table A-34 provides 20 compounds A-34.001 to A-34.020 of formula I-A1a, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0232] Table A-35 provides 20 compounds A-35.001 to A-35.020 of formula I-A1a, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0233] Table A-36 provides 20 compounds A-36.001 to A-36.020 of formula I-A1a, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0234] Table A-37 provides 20 compounds A-37.001 to A-37.020 of formula I-A1a, where R2 is C2F5, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0235] Table A-38 provides 20 compounds A-38.001 to A-38.020 of formula I-A1a, where R2 is C2F5, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0236] Table A-39 provides 20 compounds A-39.001 to A-39.020 of formula I-A1a, where R2 is C2F5, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0237] Table A-40 provides 20 compounds A-40.001 to A-40.020 of formula I-A1a, where R2 is C2F5, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0238] Table A-41 provides 20 compounds A-41.001 to A-41.020 of formula I-A1a, where R2 is C2F5, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0239] Table A-42 provides 20 compounds A-42.001 to A-42.020 of formula I-A1a, where R2 is C2F5, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0240] Table A-43 provides 20 compounds A-43.001 to A-43.020 of formula I-A1a, where R2 is OCH2CClF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0241] Table A-44 provides 20 compounds A-44.001 to A-44.020 of formula I-A1a, where R2 is OCH2CClF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0242] Table A-45 provides 20 compounds A-45.001 to A-45.020 of formula I-A1a, where R2 is OCH2CClF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0243] Table A-46 provides 20 compounds A-46.001 to A-46.020 of formula I-A1a, where R2 is OCH2CClF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0244] Table A-47 provides 20 compounds A-47.001 to A-47.020 of formula I-A1a, where R2 is OCH2CClF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0245] Table A-48 provides 20 compounds A-48.001 to A-48.020 of formula I-A1a, where R2 is OCH2CClF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0246] The following Tables B-1 to B-48 further illustrate specific compounds of the present invention. [ka]

[0247] Table B-1 provides 12 compounds B-1.001 to B-1.012 of formula I-A2a, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0248] [Table 2]

[0249] In Tables Z and B, "cycloC3" represents cyclopropyl.

[0250] For example, compound B-3.006 is [ka] is.

[0251] Table B-2 provides 12 compounds B-2.001 to B-2.012 of formula I-A2a, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0252] Table B-3 provides 12 compounds B-3.001 to B-3.012 of formula I-A2a, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0253] Table B-4 provides 12 compounds B-4.001 to B-4.012 of formula I-A2a, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0254] Table B-5 provides 12 compounds B-5.001 to B-5.012 of formula I-A2a, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0255] Table B-6 provides 12 compounds B-6.001 to B-6.012 of formula I-A2a, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0256] Table B-7 provides 12 compounds B-7.001 to B-7.012 of formula I-A2a, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0257] Table B-8 provides 12 compounds B-8.001 to B-8.012 of formula I-A2a, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0258] Table B-9 provides 12 compounds B-9.001 to B-9.012 of formula I-A2a, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0259] Table B-10 provides 12 compounds B-10.001 to B-10.012 of formula I-A2a, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0260] Table B-11 provides 12 compounds of formula I-A2a, B-11.001 to B-11.012, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0261] Table B-12 provides twelve compounds of formula I-A2a, B-12.001 to B-12.012, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0262] Table B-13 provides twelve compounds of formula I-A2a, B-13.001 to B-13.012, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0263] Table B-14 provides twelve compounds of formula I-A2a, B-14.001 to B-14.012, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0264] Table B-15 provides twelve compounds of formula I-A2a, B-15.001 to B-15.012, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0265] Table B-16 provides 12 compounds of formula I-A2a, B-16.001 to B-16.012, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0266] Table B-17 provides 12 compounds of formula I-A2a, B-17.001 to B-17.012, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0267] Table B-18 provides 12 compounds of formula I-A2a, B-18.001 to B-18.012, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0268] Table B-19 provides 12 compounds of formula I-A2a, B-19.001 to B-19.012, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0269] Table B-20 provides 12 compounds of formula I-A2a, B-20.001 to B-20.012, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0270] Table B-21 provides 12 compounds of formula I-A2a, B-21.001 to B-21.012, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0271] Table B-22 provides 12 compounds of formula I-A2a, B-22.001 to B-22.012, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0272] Table B-23 provides 12 compounds of formula I-A2a, B-23.001 to B-23.012, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0273] Table B-24 provides 12 compounds of formula I-A2a, B-24.001 to B-24.012, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0274] Table B-25 provides 12 compounds of formula I-A2a, B-25.001 to B-25.012, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0275] Table B-26 provides 12 compounds of formula I-A2a, B-26.001 to B-26.012, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0276] Table B-27 provides 12 compounds of formula I-A2a, B-27.001 to B-27.012, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0277] Table B-28 provides 12 compounds of formula I-A2a, B-28.001 to B-28.012, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0278] Table B-29 provides 12 compounds B-29.001 to B-29.012 of formula I-A2a, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0279] Table B-30 provides 12 compounds of formula I-A2a, B-30.001 to B-30.012, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0280] Table B-31 provides 12 compounds of formula I-A2a, B-31.001 to B-31.012, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0281] Table B-32 provides 12 compounds of formula I-A2a, B-32.001 to B-32.012, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0282] Table B-33 provides 12 compounds of formula I-A2a, B-33.001 to B-33.012, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0283] Table B-34 provides 12 compounds of formula I-A2a, B-34.001 to B-34.012, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0284] Table B-34 provides 12 compounds B-35.001 to B-35.012 of formula I-A2a, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0285] Table B-36 provides 12 compounds of formula I-A2a, B-36.001 to B-36.012, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0286] Table B-37 provides 12 compounds B-37.001 to B-37.012 of formula I-A2a, where R2 is C2F5, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0287] Table B-38 provides 12 compounds of formula I-A2a, B-38.001 to B-38.012, where R2 is C2F5, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0288] Table B-39 provides 12 compounds B-39.001 to B-39.012 of formula I-A2a, where R2 is C2F5, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0289] Table B-40 provides 12 compounds B-40.001 to B-40.012 of formula I-A2a, where R2 is C2F5, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0290] Table B-41 provides 12 compounds B-41.001 to B-41.012 of formula I-A2a, where R2 is C2F5, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0291] Table B-42 provides 12 compounds of formula I-A2a, B-42.001 to B-42.012, where R2 is C2F5, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0292] Table B-43 provides 12 compounds B-43.001 to B-43.012 of formula I-A2a, where R2 is OCH2CClF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0293] Table B-44 provides 12 compounds B-44.001 to B-44.012 of formula I-A2a, where R2 is OCH2CClF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0294] Table B-45 provides 12 compounds B-45.001 to B-45.012 of formula I-A2a, where R2 is OCH2CClF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0295] Table B-46 provides 12 compounds B-46.001 to B-46.012 of formula I-A2a, where R2 is OCH2CClF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0296] Table B-47 provides 12 compounds B-47.001 to B-47.012 of formula I-A2a, where R2 is OCH2CClF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0297] Table B-48 provides 12 compounds B-48.001 to B-48.012 of formula I-A2a, where R2 is OCH2CClF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0298] The following Tables C-1 to C-48 further illustrate specific compounds of the present invention. [ka]

[0299] Table C-1 provides 24 compounds of formula I-A3a, C-1.001 to C-1.024, where R2 is CF3, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0300] [Table 3]

[0301] In Tables S and C, "cycloC3" represents cyclopropyl.

[0302] Table C-2 provides 24 compounds of formula I-A3a, C-2.001 to C-2.024, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0303] Table C-3 provides 24 compounds of formula I-A3a, C-3.001 to C-3.024, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0304] Table C-4 provides 24 compounds of formula I-A3a, C-4.001 to C-4.024, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0305] Table C-5 provides 24 compounds of formula I-A3a, C-5.001 to C-5.024, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0306] Table C-6 provides 24 compounds of formula I-A3a, C-6.001 to C-6.024, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0307] Table C-7 provides 24 compounds of formula I-A3a, C-7.001 to C-7.024, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0308] Table C-8 provides 24 compounds of formula I-A3a, C-8.001 to C-8.024, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0309] Table C-9 provides 24 compounds of formula I-A3a, C-9.001 to C-9.024, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0310] Table C-10 provides 24 compounds of formula I-A3a, C-10.001 to C-10.024, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0311] Table C-11 provides 24 compounds of formula I-A3a, C-11.001 to C-11.024, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0312] Table C-12 provides 24 compounds of formula I-A3a, C-12.001 to C-12.024, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0313] Table C-13 provides 24 compounds of formula I-A3a, C-13.001 to C-13.024, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0314] Table C-14 provides 24 compounds of formula I-A3a, C-14.001 to C-14.024, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0315] Table C-15 provides 24 compounds of formula I-A3a, C-15.001 to C-15.024, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0316] Table C-16 provides 24 compounds of formula I-A3a, C-16.001 to C-16.024, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0317] Table C-17 provides 24 compounds of formula I-A3a, C-17.001 to C-17.024, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0318] Table C-18 provides 24 compounds of formula I-A3a, C-18.001 to C-18.024, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0319] Table C-19 provides 24 compounds of formula I-A3a, C-19.001 to C-19.024, where R2 is F, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0320] Table C-20 provides 24 compounds of formula I-A3a, C-20.001 to C-20.024, where R2 is F, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0321] Table C-21 provides 24 compounds of formula I-A3a, C-21.001 to C-21.024, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0322] Table C-22 provides 24 compounds of formula I-A3a, C-22.001 to C-22.024, where R2 is F, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0323] Table C-23 provides 24 compounds of formula I-A3a, C-23.001 to C-23.024, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0324] Table C-24 provides 24 compounds of formula I-A3a, C-24.001 to C-24.024, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0325] Table C-25 provides 24 compounds of formula I-A3a, C-25.001 to C-25.024, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0326] Table C-26 provides 24 compounds of formula I-A3a, C-26.001 to C-26.024, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0327] Table C-27 provides 24 compounds of formula I-A3a, C-27.001 to C-27.024, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0328] Table C-28 provides 24 compounds of formula I-A3a, C-28.001 to C-28.024, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0329] Table C-29 provides 24 compounds of formula I-A3a, C-29.001 to C-29.024, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0330] Table C-30 provides 24 compounds of formula I-A3a, C-30.001 to C-30.024, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0331] Table C-31 provides 24 compounds of formula I-A3a, C-31.001 to C-31.024, where R2 is Br, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0332] Table C-32 provides 24 compounds of formula I-A3a, C-32.001 to C-32.024, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0333] Table C-33 provides 24 compounds of formula I-A3a, C-33.001 to C-33.024, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0334] Table C-34 provides 24 compounds of formula I-A3a, C-34.001 to C-34.024, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0335] Table C-34 provides 24 compounds of formula I-A3a, C-35.001 to C-35.024, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0336] Table C-36 provides 24 compounds of formula I-A3a, C-36.001 to C-36.024, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0337] Table C-37 provides 24 compounds of formula I-A3a, C-37.001 to C-37.024, where R2 is C2F5, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0338] Table C-38 provides 24 compounds of formula I-A3a, C-38.001 to C-38.024, where R2 is C2F5, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0339] Table C-39 provides 24 compounds of formula I-A3a, C-39.001 to C-39.024, where R2 is C2F5, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0340] Table C-40 provides 24 compounds of formula I-A3a, C-40.001 to C-40.024, where R2 is C2F5, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0341] Table C-41 provides 24 compounds of formula I-A3a, C-41.001 to C-41.024, where R2 is C2F5, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0342] Table C-42 provides 24 compounds of formula I-A3a, C-42.001 to C-42.024, where R2 is C2F5, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0343] Table C-43 provides 24 compounds of formula I-A3a, C-43.001 to C-43.024, where R2 is OCH2CClF2, A is N, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0344] Table C-44 provides 24 compounds of formula I-A3a, C-44.001 to C-44.024, where R2 is OCH2CClF2, A is N, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0345] Table C-45 provides 24 compounds of formula I-A3a, C-45.001 to C-45.024, where R2 is OCH2CClF2, A is N, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0346] Table C-46 provides 24 compounds of formula I-A3a, C-46.001 to C-46.024, where R2 is OCH2CClF2, A is CH, X is S, R1 is CH2CH3, and R7 is as defined in Table S.

[0347] Table C-47 provides 24 compounds of formula I-A3a, C-47.001 to C-47.024, where R2 is OCH2CClF2, A is CH, X is SO, R1 is CH2CH3, and R7 is as defined in Table S.

[0348] Table C-48 provides 24 compounds of formula I-A3a, C-48.001 to C-48.024, where R2 is OCH2CClF2, A is CH, X is SO2, R1 is CH2CH3, and R7 is as defined in Table S.

[0349] The following Tables D-1 to D-24 further illustrate specific compounds of the present invention. [ka]

[0350] Table D-1 provides 24 compounds of formula I-A4a, D-1.001 to D-1.024, where R2 is CF3, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0351] [Table 4]

[0352] In Tables T and D, "cycloC3" represents cyclopropyl.

[0353] Table D-2 provides 24 compounds of formula I-A4a, D-2.001 to D-2.024, where R2 is CF3, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0354] Table D-3 provides 24 compounds of formula I-A4a, D-3.001 to D-3.024, where R2 is CF3, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0355] Table D-4 provides 24 compounds of formula I-A4a, D-4.001 to D-4.024, where R2 is OCHF2, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0356] Table D-5 provides 24 compounds of formula I-A4a, D-5.001 to D-5.024, where R2 is OCHF2, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0357] Table D-6 provides 24 compounds of formula I-A4a, D-6.001 to D-6.024, where R2 is OCHF2, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0358] Table D-7 provides 24 compounds of formula I-A4a, D-7.001 to D-7.024, where R2 is OCF3, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0359] Table D-8 provides 24 compounds of formula I-A4a, D-8.001 to D-8.024, where R2 is OCF3, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0360] Table D-9 provides 24 compounds of formula I-A4a, D-9.001 to D-9.024, where R2 is OCF3, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0361] Table D-10 provides 24 compounds of formula I-A4a, D-10.001 to D-10.024, where R2 is F, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0362] Table D-11 provides 24 compounds of formula I-A4a, D-11.001 to D-11.024, where R2 is F, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0363] Table D-12 provides 24 compounds of formula I-A4a, D-12.001 to D-12.024, where R2 is F, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0364] Table D-13 provides 24 compounds of formula I-A4a, D-13.001 to D-13.024, where R2 is Cl, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0365] Table D-14 provides 24 compounds of formula I-A4a, D-14.001 to D-14.024, where R2 is Cl, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0366] Table D-15 provides 24 compounds of formula I-A4a, D-15.001 to D-15.024, where R2 is Cl, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0367] Table D-16 provides 24 compounds of formula I-A4a, D-16.001 to D-16.024, where R2 is Br, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0368] Table D-17 provides 24 compounds of formula I-A4a, D-17.001 to D-17.024, where R2 is Br, X is SO, R1 is CH2CH3, and R9 is as defined in T.

[0369] Table D-18 provides 24 compounds of formula I-A4a, D-18.001 to D-18.024, where R2 is Br, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0370] Table D-19 provides 24 compounds of formula I-A4a, D-19.001 to D-19.024, where R2 is C2F5, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0371] Table D-20 provides 24 compounds of formula I-A4a, D-20.001 to D-20.024, where R2 is C2F5, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0372] Table D-21 provides 24 compounds of formula I-A4a, D-21.001 to D-21.024, where R2 is C2F5, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0373] Table D-22 provides 24 compounds of formula I-A4a, D-22.001 to D-22.024, where R2 is OCH2CClF2, X is S, R1 is CH2CH3, and R9 is as defined in Table T.

[0374] Table D-23 provides 24 compounds of formula I-A4a, D-23.001 to D-23.024, where R2 is OCH2CClF2, X is SO, R1 is CH2CH3, and R9 is as defined in Table T.

[0375] Table D-24 provides 24 compounds of formula I-A4a, D-24.001 to D-24.024, where R2 is OCH2CClF2, X is SO2, R1 is CH2CH3, and R9 is as defined in Table T.

[0376] The following Tables E-1 to E-24 further illustrate specific compounds of the present invention. [ka]

[0377] Table E-1 provides 24 compounds E-1.001 to E-1.024 of formula I-A5a, where R2 is CF3, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0378] [Table 5]

[0379] In Tables U and E, "cycloC3" represents cyclopropyl.

[0380] Table E-2 provides 24 compounds E-2.001 to E-2.024 of formula I-A5a, where R2 is CF3, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0381] Table E-3 provides 24 compounds E-3.001 to E-3.024 of formula I-A5a, where R2 is CF3, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0382] Table E-4 provides 24 compounds E-4.001 to E-4.024 of formula I-A5a, where R2 is OCHF2, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0383] Table E-5 provides 24 compounds E-5.001 to E-5.024 of formula I-A5a, where R2 is OCHF2, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0384] Table E-6 provides 24 compounds E-6.001 to E-6.024 of formula I-A5a, where R2 is OCHF2, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0385] Table E-7 provides 24 compounds E-7.001 to E-7.024 of formula I-A5a, where R2 is OCF3, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0386] Table E-8 provides 24 compounds E-8.001 to E-8.024 of formula I-A5a, where R2 is OCF3, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0387] Table E-9 provides 24 compounds E-9.001 to D-9.024 of formula I-A5a, where R2 is OCF3, X is SO2, R1 is CH2CH3, and R 11is as defined in Table U.

[0388] Table E-10 provides 24 compounds E-10.001 to E-10.024 of formula I-A5a, where R2 is F, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0389] Table E-11 provides 24 compounds E-11.001 to E-11.024 of formula I-A5a, where R2 is F, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0390] Table E-12 provides 24 compounds E-12.001 to E-12.024 of formula I-A5a, where R2 is F, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0391] Table E-13 provides 24 compounds E-13.001 to E-13.024 of formula I-A5a, where R2 is Cl, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0392] Table E-14 provides 24 compounds E-14.001 to E-14.024 of formula I-A5a, where R2 is Cl, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0393] Table E-15 provides 24 compounds E-15.001 to E-15.024 of formula I-A5a, where R2 is Cl, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0394] Table E-16 provides 24 compounds E-16.001 to E-16.024 of formula I-A5a, where R2 is Br, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0395] Table E-17 provides 24 compounds E-17.001 to E-17.024 of formula I-A5a, where R2 is Br, X is SO, R1 is CH2CH3, and R 11 is as defined in U.

[0396] Table E-18 provides 24 compounds E-18.001 to E-18.024 of formula I-A5a, where R2 is Br, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0397] Table E-19 provides 24 compounds E-19.001 to E-19.024 of formula I-A5a, where R2 is C2F5, X is S, R1 is CH2CH3, and R 11 is as defined in Table U.

[0398] Table E-20 provides 24 compounds E-20.001 to E-20.024 of formula I-A5a, where R2 is C2F5, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0399] Table E-21 provides 24 compounds E-21.001 to E-21.024 of formula I-A5a, where R2 is C2F5, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0400] Table E-22 provides 24 compounds E-22.001 to E-22.024 of formula I-A5a, where R2 is OCH2CClF2, X is S, R1 is CH2CH3, and R 11is as defined in Table U.

[0401] Table E-23 provides 24 compounds E-23.001 to E-23.024 of formula I-A5a, where R2 is OCH2CClF2, X is SO, R1 is CH2CH3, and R 11 is as defined in Table U.

[0402] Table E-24 provides 24 compounds E-24.001 to E-24.024 of formula I-A5a, where R2 is OCH2CClF2, X is SO2, R1 is CH2CH3, and R 11 is as defined in Table U.

[0403] The following Tables F1-F-48 further illustrate specific compounds of the present invention. [ka]

[0404] In Tables Y and F, "cycloC3" represents cyclopropyl.

[0405] Table F-1 provides 20 compounds F-1.001 to F-1.020 of formula IB-1a, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0406] Table F-2 provides 20 compounds F-2.001 to F-2.020 of formula IB-1a, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0407] Table F-3 provides 20 compounds F-3.001 to F-3.020 of formula IB-1a, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0408] Table F-4 provides 20 compounds F-4.001 to F-4.020 of formula IB-1a, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0409] Table F-5 provides 20 compounds F-5.001 to F-5.020 of formula IB-1a, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0410] Table F-6 provides 20 compounds F-6.001 to F-6.020 of formula IB-1a, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0411] Table F-7 provides 20 compounds F-7.001 to F-7.020 of formula IB-1a, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0412] Table F-8 provides 20 compounds F-8.001 to F-8.020 of formula IB-1a, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0413] Table F-9 provides 20 compounds F-9.001 to F-9.020 of formula IB-1a, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0414] Table F-10 provides 20 compounds F-10.001 to F-10.020 of formula IB-1a, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0415] Table F-11 provides 20 compounds F-11.001 to F-11.020 of formula IB-1a, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0416] Table F-12 provides 20 compounds F-12.001 to F-12.020 of formula IB-1a, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0417] Table F-13 provides 20 compounds F-13.001 to F-13.020 of formula IB-1a, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0418] Table F-14 provides 20 compounds F-14.001 to F-14.020 of formula IB-1a, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0419] Table F-15 provides 20 compounds F-15.001 to F-15.020 of formula IB-1a, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0420] Table F-16 provides 20 compounds F-16.001 to F-16.020 of formula IB-1a, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0421] Table F-17 provides 20 compounds F-17.001 to F-17.020 of formula IB-1a, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0422] Table F-18 provides 20 compounds F-18.001 to F-18.020 of formula IB-1a, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0423] Table F-19 provides 20 compounds F-19.001 to F-19.020 of formula IB-1a, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0424] Table F-20 provides 20 compounds F-20.001 to F-20.020 of formula IB-1a, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0425] Table F-21 provides 20 compounds F-21.001 to F-21.020 of formula IB-1a, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0426] Table F-22 provides 20 compounds F-22.001 to F-22.020 of formula IB-1a, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0427] Table F-23 provides 20 compounds F-23.001 to F-23.020 of formula IB-1a, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0428] Table F-24 provides 20 compounds F-24.001 to F-24.020 of formula IB-1a, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0429] Table F-25 provides 20 compounds F-25.001 to F-25.020 of formula IB-1a, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0430] Table F-26 provides 20 compounds F-26.001 to F-26.020 of formula IB-1a, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0431] Table F-27 provides 20 compounds F-27.001 to F-27.020 of formula IB-1a, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0432] Table F-28 provides 20 compounds F-28.001 to F-28.020 of formula IB-1a, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0433] Table F-29 provides 20 compounds F-29.001 to F-29.020 of formula IB-1a, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0434] Table F-30 provides 20 compounds F-30.001 to F-30.020 of formula IB-1a, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0435] Table F-31 provides 20 compounds F-31.001 to F-31.020 of formula IB-1a, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0436] Table F-32 provides 20 compounds F-32.001 to F-32.020 of formula IB-1a, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0437] Table F-33 provides 20 compounds F-33.001 to F-33.020 of formula IB-1a, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0438] Table F-34 provides 20 compounds F-34.001 to F-34.020 of formula IB-1a, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0439] Table F-35 provides 20 compounds F-35.001 to F-35.020 of formula IB-1a, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0440] Table F-36 provides 20 compounds F-36.001 to F-36.020 of formula IB-1a, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0441] Table F-37 provides 20 compounds F-37.001 to F-37.020 of formula IB-1a, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0442] Table F-38 provides 20 compounds F-38.001 to F-38.020 of formula IB-1a, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0443] Table F-39 provides 20 compounds F-39.001 to F-39.020 of formula IB-1a, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0444] Table F-40 provides 20 compounds F-40.001 to F-40.020 of formula IB-1a, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0445] Table F-41 provides 20 compounds F-41.001 to F-41.020 of formula IB-1a, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0446] Table F-42 provides 20 compounds F-42.001 to F-42.020 of formula IB-1a, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0447] Table F-43 provides 20 compounds F-43.001 to F-43.020 of formula IB-1a, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0448] Table F-44 provides 20 compounds F-44.001 to F-44.020 of formula IB-1a, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0449] Table F-45 provides 20 compounds F-45.001 to F-45.020 of formula IB-1a, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0450] Table F-46 provides 20 compounds F-46.001 to F-46.020 of formula IB-1a, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0451] Table F-47 provides 20 compounds F-47.001 to F-47.020 of formula IB-1a, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0452] Table F-48 provides 20 compounds F-48.001 to F-48.020 of formula IB-1a, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0453] The following Tables G-1 to G-48 further illustrate specific compounds of the present invention. [ka]

[0454] In Tables Z and G, "cycloC3" represents cyclopropyl.

[0455] Table G-1 provides 12 compounds G-1.001 to G-1.012 of formula IB-1b, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0456] Table G-2 provides 12 compounds G-2.001 to G-2.012 of formula IB-1b, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0457] Table G-3 provides 12 compounds G-3.001 to G-3.012 of formula IB-1b, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0458] Table G-4 provides 12 compounds G-4.001 to G-4.012 of formula IB-1b, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0459] Table G-5 provides 12 compounds G-5.001 to G-5.012 of formula IB-1b, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0460] Table G-6 provides 12 compounds G-6.001 to G-6.012 of formula IB-1b, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0461] Table G-7 provides 12 compounds G-7.001 to G-7.012 of formula IB-1b, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0462] Table G-8 provides 12 compounds G-8.001 to G-8.012 of formula IB-1b, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0463] Table G-9 provides 12 compounds G-9.001 to G-9.012 of formula IB-1b, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0464] Table G-10 provides 12 compounds G-10.001 to G-10.012 of formula IB-1b, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0465] Table G-11 provides 12 compounds G-11.001 to G-11.012 of formula IB-1b, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0466] Table G-12 provides twelve compounds G-12.001 to G-12.012 of formula IB-1b, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0467] Table G-13 provides twelve compounds G-13.001 to G-13.012 of formula IB-1b, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0468] Table G-14 provides twelve compounds G-14.001 to G-14.012 of formula IB-1b, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0469] Table G-15 provides twelve compounds G-15.001 to G-15.012 of formula IB-1b, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0470] Table G-16 provides twelve compounds G-16.001 to G-16.012 of formula IB-1b, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0471] Table G-17 provides 12 compounds G-17.001 to G-17.012 of formula IB-1b, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0472] Table G-18 provides 12 compounds G-18.001 to G-18.012 of formula IB-1b, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0473] Table G-19 provides 12 compounds G-19.001 to G-19.012 of formula IB-1b, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0474] Table G-20 provides 12 compounds G-20.001 to G-20.012 of formula IB-1b, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0475] Table G-21 provides 12 compounds G-21.001 to G-21.012 of formula IB-1b, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0476] Table G-22 provides twelve compounds G-22.001 to G-22.012 of formula IB-1b, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0477] Table G-23 provides twelve compounds G-23.001 to D-23.012 of formula IB-1b, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0478] Table G-24 provides 12 compounds G-24.001 to G-24.012 of formula IB-1b, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0479] Table G-25 provides 12 compounds G-25.001 to G-25.012 of formula IB-1b, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0480] Table G-26 provides 12 compounds G-26.001 to G-26.012 of formula IB-1b, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0481] Table G-27 provides 12 compounds G-27.001 to G-27.012 of formula IB-1b, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0482] Table G-28 provides 12 compounds G-28.001 to G-28.012 of formula IB-1b, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0483] Table G-29 provides 12 compounds G-29.001 to G-29.012 of formula IB-1b, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0484] Table G-30 provides twelve compounds G-30.001 to G-30.012 of formula IB-1b, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0485] Table G-31 provides 12 compounds G-31.001 to G-31.012 of formula IB-1b, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0486] Table G-32 provides twelve compounds G-32.001 to G-32.012 of formula IB-1b, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0487] Table G-33 provides twelve compounds G-33.001 to G-33.012 of formula IB-1b, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0488] Table G-34 provides twelve compounds G-34.001 to G-34.012 of formula IB-1b, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0489] Table G-35 provides 12 compounds G-35.001 to G-35.012 of formula IB-1b, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0490] Table G-36 provides 12 compounds G-36.001 to G-36.012 of formula IB-1b, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0491] Table G-37 provides 12 compounds G-37.001 to G-37.012 of formula IB-1b, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0492] Table G-38 provides 12 compounds G-38.001 to G-38.012 of formula IB-1b, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0493] Table G-39 provides 12 compounds G-39.001 to G-39.012 of formula IB-1b, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0494] Table G-40 provides 12 compounds G-40.001 to G-40.012 of formula IB-1b, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0495] Table G-41 provides 12 compounds G-41.001 to G-41.012 of formula IB-1b, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0496] Table G-42 provides 12 compounds G-42.001 to G-42.012 of formula IB-1b, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0497] Table G-43 provides 12 compounds G-43.001 to G-43.012 of formula IB-1b, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0498] Table G-44 provides 12 compounds G-44.001 to G-44.012 of formula IB-1b, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0499] Table G-45 provides 12 compounds G-45.001 to G-45.012 of formula IB-1b, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0500] Table G-46 provides 12 compounds G-46.001 to G-46.012 of formula IB-1b, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0501] Table G-47 provides 12 compounds G-47.001 to G-47.012 of formula IB-1b, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0502] Table G-48 provides 12 compounds G-48.001 to G-48.012 of formula IB-1b, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0503] The following Tables H-1 to H-6 further exemplify specific compounds of the present invention. [ka]

[0504] In Tables Y and H, "cycloC3" represents cyclopropyl.

[0505] Table H-1 provides 20 compounds H-1.001 to H-1.020 of formula IB-2a, where A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0506] Table H-2 provides 20 compounds H-2.001 to H-2.020 of formula IB-2a, where A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0507] Table H-3 provides 20 compounds H-3.001 to H-3.020 of formula IB-2a, where A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0508] Table H-4 provides 20 compounds H-1.001 to H-1.020 of formula IB-2a, where A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0509] Table H-5 provides 20 compounds H-2.001 to H-2.020 of formula IB-2a, where A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0510] Table H-6 provides 20 compounds H-3.001 to H-3.020 of formula IB-2a, where A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0511] The following Tables J-1 to J-6 further exemplify specific compounds of the present invention. [ka]

[0512] In Tables Z and J, "cycloC3" represents cyclopropyl.

[0513] Table J-1 provides 12 compounds J-1.001 to J-1.012 of formula IB-2b, where A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0514] Table J-2 provides 12 compounds J-2.001 to J-2.012 of formula IB-2b, where A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0515] Table J-3 provides 12 compounds J-3.001 to J-3.012 of formula IB-2b, where A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0516] Table J-4 provides 12 compounds J-1.001 to J-1.012 of formula IB-2b, where A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0517] Table J-5 provides 12 compounds J-2.001 to J-2.012 of formula IB-2b, where A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0518] Table J-6 provides 12 compounds J-3.001 to J-3.012 of formula IB-2b, where A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0519] The compounds of formula I according to the invention are preventively and / or therapeutically useful active ingredients in the field of pest control, even at low application rates, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded animal species, fish, and plants. The active ingredients according to the invention act not only against normally susceptible animal pests, such as insects or representatives of the order Acarina, but also against all or individual developmental stages of resistant animal pests. The insecticidal or acaricidal activity of the active ingredients according to the invention can be manifested directly (i.e., killing of the pest immediately or only after a certain period of time, for example during molting) or indirectly (e.g., by reducing egg production and / or hatching rate, a good activity corresponding to a killing rate (mortality) of at least 50-60%).

[0520] Examples of the animal pests mentioned above are: Acari (order Acarina), e.g. Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp., Eotetranychus spp. spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Olygonychus spp., Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp., Psoroptes spp., Rhipicephalus spp.), Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp., Tarsonemus spp. and Tetranychus spp.; Order Anoplura, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; Coleoptera (order Coleoptera), e.g. Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp.), Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa ​​decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera castanea, Megascelis spp. spp., Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp., Popillia spp.), Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabaeidae, Sitophilus spp., Sitotroga spp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.;. Diptera (order Diptera), e.g. Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, Fannia spp. spp.), Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp. spp.), Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; Hemiptera (order Hemiptera), e.g. Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp., Clavigrella tomentosicollis, Creontiades spp., Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp., Euschistus spp. spp.), Eurydema pulchrum, Eurygaster spp., Brown marmorated stink bugs (Halyomorpha halys), Horcias nobilellus, Leptocorisa spp., Mire bugs (Lygus spp.), Margarodes spp., Murgantia histrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp. spp.), Piezodorus spp., Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp., Thyanta spp., Triatoma spp.) and Vatiga illudens;. Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscena targionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp. spp.), Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp., Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariella aegopodii Scop., Ceroplaster spp.), Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp., Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp., Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp.), Neotoxoptera spp., Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Bayberry whitefly (Parabemisia myricae), Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Corn planthopper (Peregrinus maidis), Perkinsiella spp., Hop wart aphid (Phorodon humuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp. spp.), Schizaphis spp., Sitobion spp.), Sogatella furcifera, Spisstilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris; Hymenoptera (order Hymenoptera), e.g. Acromyrmex ants, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis ants, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta, Solenopsis spp. and Vespa spp.; Termites (order Isoptera), e.g. Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis geminate; Lepidoptera (order Lepidoptera), e.g. Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp.), Epinotia spp., Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp., Hyphantria cunea, Keiferia lycopersicella lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp., Orniodes indica indica), European corn borer (Ostrinia nubilalis), Pammene spp., Pandemis spp.), pine sawyer moth (Panolis flammea), Papaipema nebris, pink bollworm (Pectinophora gossypiela), coffee leafminer (Perileucoptera coffeella), Pseudaletia unipuncta, potato tuber moth (Phthorimaea operculella), cabbage white butterfly (Pieris rapae), Pieris spp., diamondback moth (Plutella xylostella), Prays spp., Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp.), Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta and Yponomeuta spp.;. Order Mallophaga, e.g. Damalinea spp. and Trichodectes spp.; Orthoptera (order Orthoptera), e.g. Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp. and Schistocerca spp.; Psocoptera (order Psocoptera), e.g. Liposcelis spp.; Order Siphonaptera, e.g. Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; Thrips (order Thysanoptera), e.g. Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.; Order Thysanura, for example, Lepisma saccharina.

[0521] The active ingredients according to the invention can be used to control, i.e. contain or destroy, pests of the above-mentioned types that occur in particular on plants, in particular on useful and ornamental plants in agriculture, horticulture and forestry, or on organs of such plants, such as fruits, flowers, leaves, stems, tubers or roots, in some cases plant organs that are formed even later and remain protected against these pests.

[0522] Suitable target crops are, in particular, cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beets, such as sugar or fodder beets; fruits, such as pome fruits, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; legumes, for example beans, lentils, peas or soybeans; oil crops, for example rapeseed, mustard, poppy, olives, sunflower, coconut, castor bean, cocoa or ground nuts; cucurbits. , for example pumpkin, cucumber or melon; fiber plants, for example cotton, flax, hemp or jute; citrus fruits, for example orange, lemon, grapefruit or tangerine; vegetables, for example spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato or bell pepper; Lauraceae, for example avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevine, hops, Plantaginaceae and latex plants.

[0523] The compositions and / or methods of the present invention may be used on any ornamental and / or vegetable crop, including flowers, shrubs, broadleaf trees and evergreen trees.

[0524] For example, the present invention can be used with any of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g., B. elatior, B. semperflorens, B. tubereux), Bougainvillea spp., Brachycome spp., Brassica spp. (ornamental), Calceolaria spp. spp.), Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp.), Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (I. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp.), Tagetes spp., Dianthus spp. (carnations), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp. (pansies), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp., Parthenocissus spp.) (P. quinquefolia, P. tricuspidata), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (roses), Rudbeckia spp., Saintpaulia spp., Salvia spp.), Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.

[0525] For example, the present invention can be used with any of the following vegetable species: Allium spp. (garlic (A. sativum), onion (A. cepa), shallot (A. oschaninii), leek (A. porrum), scallion (A. ascalonicum), green onion (A. fistulosum)), chervil (Anthriscus cerefolium), celery (Apium graveolus), asparagus (Asparagus officinalis), beet (Beta vulgarus), Brassica spp. (B. oleracea, Chinese cabbage (B. pekinensis), turnip (B. rapa)), pepper (Capsicum annuum), chickpea (Cicer arietinum), endive (Cichorium endivia), Cichorum spp. spp.) (chicory (C. intybus), endive (C. endivia)), watermelon (Citrillus lanatus), Cucumis spp. (saffron (C. sativus), melon (C. melo)), Cucurbita spp. (Cucurbita pepo, Cucurbita maxima), Cyanara spp. (artichoke (C. scolymus), cardoon (C. cardunculus)), carrot (Daucus carota), fennel (Foeniculum vulgare), Hypericum spp., lettuce (Lactuca sativa), tomato (Lycopersicon spp.) (tomato (L. esculentum), tomato (L. lycopersicum)), mint (Mentha spp.), basil (Ocimum basilicum), parsley (Petroselinum crispum), Phaseolus spp. (Phaseolus vulgaris, runner bean (P.coccineus), pea (Pisum sativum), radish (Raphanus sativus), rhubarb (Rheum rhaponticum), rosemary (Rosemarinus spp.), salvia (Salvia spp.), yellow rosemary (Scorzonera hispanica), eggplant (Solanum melongena), spinach (Spinacea oleracea), Valerianella spp. (V. locusta, V. eriocarpa) and broad bean (Vicia faba).

[0526] Preferred ornamental plant species include African violet, begonia, dahlia, gerbera, hydrangea, verbena, rosa, kalanchoe, poinsettia, aster, centaurea, coreopsis, delphinium, monarda, and phlox. , Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. John's wort, mint, peppers, tomatoes, and cucumbers.

[0527] The active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella, and Spodoptera littoralis in cotton, vegetable, corn, rice, and soybean crops. They are even more particularly suitable for controlling Mamestra (preferably on vegetables), codling moth (Cydia pomonella) (preferably on apples), Empoasca (preferably on vegetables and vineyards), Leptinotarsa ​​(preferably on potatoes), and Chilo supressalis (preferably on rice).

[0528] The active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella, and Spodoptera littoralis in cotton, vegetable, corn, rice, and soybean crops. The active ingredients according to the invention are particularly suitable for controlling Mamestra (preferably on vegetables), codling moth (Cydia pomonella) (preferably on apple), Empoasca (preferably on vegetables and vineyards), Leptinotarsa ​​(preferably on potato), and Chilo supressalis (preferably on rice).

[0529] In a further aspect, the present invention relates to plant parasitic nematodes (endoparasitic, semiendoparasitic and ectoparasitic nematodes), in particular root-knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, beet cyst nematode, Heterodera schachtii, black-bathed cyst nematode (Heterodera trifolii) and other Heterodera species; seed nematodes, Anguina species; stem and leaf nematodes, Aphelenchoides species; stinging nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematode, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species;Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; sheath and sheath-like nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; Root-knot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematode, Radopholus similis and other Radopholus species; Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematode, Trichodurus primitiveus primitivus and other Trichodurus species, Paratrichodorus species; Stunt nematode, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species;The present invention may also relate to a method of controlling damage to plants and parts thereof by plant-parasitic nematodes, such as Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant-parasitic nematode species, such as Subanguina, Hypsoperine, Macroposthonia, Melinius, Punctodera, and Quinisulcius.

[0530] The compounds of the present invention may also have activity against mollusks, examples of which include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena furticum); fruticum); Cepaea (C. hortensis, C. nemoralis); Ochrogyna; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euonphalia; Galba (G. trunculata); Heliceria (H. itala, H. obvia); Helicidae Helicigona albustrum arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0531] It should be understood that the term "crop plant" also includes crop plants that have been transformed using recombinant DNA techniques to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0532] Toxins that can be expressed by the transformed plants include, for example, insecticidal proteins, such as insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from bacteria, such as Photorhabdus spp. or Xenorhabdus spp., e.g., Photorhabdus luminescens, Xenorhabdus nematophilus, insecticidal proteins of nematode-symbiotic bacteria such as Azotoxins; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, ruffin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0533] In the context of the present invention, delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, are also understood to be, in particular, hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins in a new way (see, for example, WO 02 / 15701). For example, truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0534] Examples of such toxins or transformed plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0535] The process for preparing such transgenic plants is generally known to those skilled in the art and is described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0536] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0537] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, some of which are commercially available. Examples of such plants include YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) for tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0538] Further examples of such transgenic crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically modified maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenicly expresses the enzyme PAT, conferring tolerance to the herbicide glufosinate-ammonium. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. This genetically modified maize (Zea mays) is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of a truncated Cry1Ab toxin. Bt176 maize also transgenicly expresses the enzyme PAT, conferring tolerance to the herbicide glufosinate-ammonium. 3. MIR604 corn, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03 / 018810. 4. MON 863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. IPC 531 cotton from Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6. 1507 Maize, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the Cry1F protein for resistance to certain Lepidoptera insects and the PAT protein for resistance to the herbicide glufosinate ammonium. 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This conventional hybrid maize variety is a cross between the genetically modified varieties NK603 and MON 810. NK603 x MON810 maize transgenicly expresses the CP4 EPSPS protein from Agrobacterium sp. strain CP4, which confers resistance to the Roundup® herbicide (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0539] Transformed insect-resistant plants are also described in the BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003 (http: / / bats.ch).

[0540] The term "crop" should also be understood to include crop plants that have been transformed using DNA recombinant techniques so as to be able to synthesize antipathogenic substances with selective action, such as so-called "infection-specific proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transformed plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such transformed plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0541] Crops can also be modified for enhanced resistance to fungal (e.g., Fusarium, Anthracnose, or Phytophthora), bacterial (e.g., Pseudomonas), or viral (e.g., potato leaf curl virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

[0542] Crops also include those with enhanced resistance to nematodes, such as the soybean cyst nematode.

[0543] Crops that are tolerant to abiotic stress include, for example, those that have enhanced tolerance to drought, high salinity, high temperature, low temperature, frost, or light due to expression of NF-YB or other proteins known in the art.

[0544] Anti-pathogenic substances that can be expressed by such transformed plants include, for example, ion channel blockers, such as sodium and calcium channel blockers, for example viral KP1, KP4 or KP6 toxins, stilbene synthases, bibenzyl synthases, chitinases, glucanases, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP 0 392 225), anti-pathogenic substances produced by microorganisms, such as peptide or heterocyclic antibiotics (see, for example, WO 95 / 33818), or proteins or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes", as described in WO 03 / 000906).

[0545] Further areas of use of the compositions according to the invention are the protection of stored goods and storage rooms against pests of the types mentioned and the protection of raw materials such as wood, textiles, floor coverings or buildings and also in the hygiene sector, in particular the protection of humans, livestock and productive livestock.

[0546] The present invention also provides methods for controlling pests (e.g., mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests comprises applying a composition of the present invention to target pests, their habitats, or surfaces or substrates by brushing, rolling, spraying, dusting, or dipping. By way of example, IRS (indoor residual spray) application of surfaces, such as wall, ceiling, or floor surfaces, is contemplated by the method of the present invention. In another embodiment, it is contemplated to apply such compositions to substrates, such as nonwoven or woven materials, in the form of (or that can be used in the manufacture of) netting, clothing, bedding, curtains, and tents.

[0547] In one embodiment, a method for controlling such pests comprises applying a pesticidally effective amount of a composition of the present invention to target pests, their habitat, or a surface or substrate to achieve effective residual pesticidal activity on the surface or substrate. Such application may be by brushing, rolling, spraying, dusting, or dipping the pesticidal composition of the present invention. By way of example, IRS application of surfaces, such as wall, ceiling, or floor surfaces, is contemplated by the method of the present invention to achieve effective residual pesticidal activity on the surface. In another embodiment, application of such compositions for residual control of pests on substrates, such as fabric materials in the form of (or that can be used in the manufacture of) netting, clothing, bedding, curtains, and tents, is contemplated.

[0548] The substrates to be treated, including nonwovens, fabrics, or netting, can be made of natural fibers such as cotton, raffia, jute, flax, sisal, burlap, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile, etc. Polyester is particularly suitable. Methods for treating textiles are known, for example, WO 2008 / 151984, WO 2003 / 034823, U.S. Pat. No. 5,631,072, WO 2005 / 64072, WO 2006 / 128870, EP 1,724,392, WO 2005,113,886, or WO 2007 / 090739.

[0549] A further area of ​​use of the compositions according to the invention is in the field of trunk injection / trunk treatment for all ornamental trees and all fruit and nut trees.

[0550] In the field of trunk injection / trunk treatment, the compounds according to the invention are particularly suitable against wood-boring insects from the orders Lepidoptera and Coleoptera as mentioned above, in particular against the wood-boring organisms listed in Tables A and B below.

[0551] [Table 6]

[0552] [Table 7-1]

[0553] [Table 7-2]

[0554] [Table 7-3]

[0555] The present invention may also be used to control any pest that may be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, woodlice, mites, mole crickets, scale insects, mealybugs, mites, boxworms, long-legged bugs, and grubs. The present invention may be used to control pests at various stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0556] In particular, the present invention may be used to control grubs (e.g., Cyclocephala spp. (e.g., masked scarabs, C. lurida), Rhizotrogus spp. (e.g., European scarabs, R. majalis), Cotinus spp. (e.g., blue cockroach beetles, C. nitida), Popillia spp. (e.g., Japanese beetles, P. japonica), Phyllophaga spp. (e.g., May / June beetles), Ataenius spp. spp.) (e.g., black turfgrass Attaenius, A. spretulus), Maladera spp. (e.g., red-velvet beetle, M. castanea) and Tomarus spp.), ground pearls (Margarodes spp.), mole crickets (tan, southern and short-winged; Scapteriscus spp., Gryllotalpa africana) and crane fly larvae (European crane fly, Tipula spp.).

[0557] The present invention may also be used to control straw-dwelling turfgrass pests, including cutworms (e.g., the armyworm Spodoptera frugiperda and the common cutworm Pseudaletia unipuncta), cutworms, weevils (Sphenophorus spp., e.g., S. venatus verstitus and S. parvulus), and sod webworms (e.g., Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).

[0558] The present invention may also be used to control turfgrass pests that live above ground and feed on turfgrass leaves, including stink bugs (e.g., Blissus insularis), stag beetles (Eriophyes cynodoniensis), oak leafbugs (Antonina graminis), two-lined spittlebugs (Propsapia bicincta), leafhoppers, cutworms (Noctuidae), and greengrass aphids. The present invention may also be used to control other turfgrass pests, such as the red fire ant (Solenopsis invicta), which causes ant mounds in turf.

[0559] In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard mites, scorpion mites, scabies mites, chiggers, flies (stable flies and dentaries), parasitic fly larvae, lice, head lice, biting lice and fleas.

[0560] Examples of such parasites are: In the order Anoplurida, the genera Haematopinus, Linognathus, Pediculus, Phtirus and Solenopotes are included.

[0561] From the order Mallophagida, the genera Trimenopon, Menopon, Trinoton, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes and Felicola.

[0562] From the order Diptera and the suborders Nematocerina and Brachycerina, for example, the genera Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp.), Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.), Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0563] From the order Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., and Ceratophyllus spp.

[0564] From the order Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

[0565] From the order Blattarida, for example, the Asian cockroach, the American cockroach, Blattela germanica and Supella spp.

[0566] From the subclass Acaria (Acarida) and the orders Metastigmata and Mesostigmata, for example, the genera Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp. spp.), Pneumonyssus spp., Sternostoma spp. and Varroa spp.

[0567] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp. spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0568] The compositions according to the invention are suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and also buildings against insect infestation.

[0569] The compositions according to the invention can be used, for example, against the following pests: beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicolis. planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus species, Tryptodendron species, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon speciesand Dinoderus minutus, and also insects of the order Hymenopterans, for example Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites, for example Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and silverfish such as Lepisma saccharina.

[0570] Although the compounds according to the present invention can be used as pesticides in their native form, they are generally formulated into compositions using formulation aids such as carriers, solvents, and surfactants in various ways.The formulations can be in various physical forms, such as dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010).Such formulations can be used directly or diluted before use.Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological materials, oils, or solvents.

[0571] The formulations can be prepared by mixing the active ingredient with formulation adjuvants to obtain compositions in the form of, for example, finely divided solids, granules, solutions, dispersions or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surfactants or combinations thereof.

[0572] The active ingredient can also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules typically have diameters of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95 wt% of the capsule weight. The active ingredient can be in the form of a monolithic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulating membrane can comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers and starch xanthate, or other polymers known to those skilled in the art. Alternatively, fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of a base material, but the microcapsules themselves are not encapsulated.

[0573] The formulation auxiliaries suitable for preparing the compositions according to the invention are known per se. Examples of liquid carriers include water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abiet, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid Examples of suitable solvents include methyl alcohol, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone.

[0574] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed kernels, wheat flour, soybean flour, pumice, wood flour, ground walnut kernels, lignin and similar substances.

[0575] Many surface-active substances can be advantageously used in both solid and liquid formulations, especially in formulations that can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic, or polymeric and can be used as emulsifying agents, wetting agents, or suspending agents, or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters; and also, for example, McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New York, 1989. Contains additional substances described in Jersey (1981).

[0576] Further adjuvants that can be used in the pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0577] The composition according to the present invention may contain an additive comprising a vegetable oil or animal oil, a mineral oil, an alkyl ester of such oils, or a mixture of such oils and oil derivatives. The amount of oil additive in the composition according to the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or vegetable oils such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils, e.g., methyl derivatives, or animal oils such as fish oil or beef tallow. Preferred oil additives are C8 to C9 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively), are included. Many oil derivatives are listed in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0578] The compositions of the present invention generally comprise 0.1 to 99% by weight, especially 0.1 to 95% by weight, of a compound of the present invention and 1 to 99.9% by weight of formulation adjuvants, preferably including 0 to 25% by weight of a surfactant. Commercial products are preferably formulated as concentrates, although end users will typically utilize diluted formulations.

[0579] The application rate varies within wide limits and depends on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing climatic conditions, and other factors governed by the method, time of application and target crop. As a general guideline, the compounds may be applied at a rate of 1 to 2000 l / ha, especially 10 to 1000 l / ha.

[0580] A preferred formulation may have the following composition (% by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0581] Dust: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0582] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1-40%, preferably 2-30%

[0583] Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0584] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0585] The following examples further illustrate, but do not limit, the present invention.

[0586] [Table 8]

[0587] This combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder, which is diluted with water to obtain a suspension of the desired concentration.

[0588] [Table 9]

[0589] This combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly as a seed treatment.

[0590] [Table 10]

[0591] Emulsions of any desired dilution that can be used for plant protection are obtained from this concentrate by dilution with water.

[0592] [Table 11]

[0593] Ready-to-use dusts can be obtained by combining and mixing with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressing of seeds.

[0594] [Table 12]

[0595] This combination is mixed with an adjuvant and ground, the mixture is moistened with water, extruded, and then dried in a stream of air.

[0596] [Table 13]

[0597] This micronized combination is applied uniformly in a mixer to kaolin wetted with polyethylene glycol, thus obtaining coated granules that do not generate dust.

[0598] [Table 14]

[0599] The combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect them from microbial infestation.

[0600] [Table 15]

[0601] The combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect them from microbial infestation.

[0602] Sustained-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is reached. To this emulsion, a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by the addition of 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The media capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for that purpose.

[0603] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically preferred formulation in combination with agriculturally acceptable adjuvants. [Example]

[0604] Preparation Examples: "Mp" means melting point (°C). The free radical represents a methyl group. 1 H NMR measurements were recorded on a Brucker 400 MHz spectrometer and chemical shifts are given in ppm relative to a TMS standard. Spectra were measured in deuterated solvents as specified. Compounds were characterized using one of the following LCMS methods. The characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", reported in minutes) and the observed molecular ion (M+H). + or (MH) - It was.

[0605] Method 1: Spectra were recorded using a Waters mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: reversible polarity, capillary voltage: 0.8–3.00 kV, cone range: 25, source temperature: 120–150 °C, desolvation temperature: 500–600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass scan range: 110–850 Da) and a Waters Acquity UPLC: quaternary solvent manager, heated column compartment, diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm; Temperature: 40 °C; DAD wavelength range (nm): 200–400; Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH; Gradient: 10% B (0 min); 10–50% B (0–0.2 min); 50–100% B (0.2–0.6 min); 100% B (0.6–1.3 min); 100–10% B (1.3–1.4 min); 10% B (1.4–1.6 min); Flow rate (mL / min) 0.6.

[0606] Method 2: Spectra were recorded on an Agilent Technologies mass spectrometer (MSD-IQ mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary: 3.5 kV, fragmentor: 110 V, desolvation temperature: 325 °C, gas flow: 13 L / min, nebulizer gas: 55 psi, mass range: 110–850 Da) and an Agilent 1290 series HPLC: quaternary pump, heated column compartment, and diode array detector. Column: AGILENT POROSHELL 120 EC-C18, 1.9 μm, 50 × 2.1 mm; Temperature: 40 °C; DAD wavelength range (nm): 190–400; Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH; Gradient: 0–0.5 min: 10% B, 90% A; 1.2–1.5 min: 95% B, 0.5% A; 1.8–2.5 min: 10% B, 90% A; Flow rate (ml / min): 0.8

[0607] Method 3: Spectra were recorded using a mass spectrometer (6410 Triple Quadrupole Mass Spectrometer) from Agilent Technologies equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary voltage: 4.00 kV, fragmentor voltage: 100 V, desolvation temperature: 350 °C, gas flow rate: 11 L / min, nebulizer gas: 45 psi, mass scan range: 110-1000 Da) and a 1200 Series HPLC from Agilent: quaternary pump, heated column compartment and VWD detector, column: KINETEX EVO C18, 2.6 μm, 50 × 4.6 mm, temperature: 40 °C, detector VWD wavelength: 254 nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH HCOOH: Gradient: 10% B, 90% A (0 min); 100% B (0.9-1.8 min); 100-10% B (1.8-2.2 min); 10% B (2.2-2.5 min); flow rate (mL / min) 1.8.

[0608] Method 4: Spectra were recorded using an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive and negative ions, capillary voltage: 3.0 kV, cone voltage: 30 V, extractor voltage: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow rate: 60 L / hr, desolvation gas flow rate: 700 L / hr, mass scan range: 140-800 Da), and an ACQUITY UPLC from Waters Corporation equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 2.5 min; Flow rate (ml / min): 0.75.

[0609] Method 5: Spectra were recorded using a mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive and negative ions): capillary voltage: 0.8-3.00 kV, cone voltage: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass scan range: 110-950 Da and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Run time: 1.5 min; Solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; Flow rate (ml / min): 0.85; Gradient: 10% B isocratic (0.2 min), then 10–100% B (1.0 min), 100% B isocratic (0.2 min), 100–10% B (0.05 min), 10% B isocratic (0.05 min).

[0610] Example P1: Preparation of 6-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5-one (compound P.1) [ka] Step 1: Preparation of ethyl 2-(2-tert-butoxy-1-cyano-2-oxo-ethyl)-6-(trifluoromethyl)pyridine-3-carboxylate (Intermediate I1) [ka] To a solution of ethyl 2-chloro-6-(trifluoromethyl)pyridine-3-carboxylate (2.00 g, 7.89 mmol) in DMSO (10 mL) was added potassium carbonate (1.63 g, 11.8 mmol, 1.5 equiv.) followed by tert-butyl 2-cyanoacetate (1.34 g, 9.46 mmol, 1.2 equiv.) at room temperature. The reaction mixture was stirred at 100° C. for 4 hours. The reaction mixture was then quenched with ice-cold water, stirred for 10 minutes, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash (10% ethyl acetate in cyclohexane) to give 2.0 g of ethyl 2-(2-tert-butoxy-1-cyano-2-oxo-ethyl)-6-(trifluoromethyl)pyridine-3-carboxylate as a thick yellow oil. 1 H NMR(400MHz,CDCl3)δ ppm:1.41-1.50(m,3H),1.51(s,9H),4.46(q,2H),5.87(s,1H),7.83(d,1H),8.58(d,1H).

[0611] Step 2: Preparation of ethyl 2-(cyanomethyl)-6-(trifluoromethyl)pyridine-3-carboxylate (Intermediate I2) [ka] To a solution of ethyl 2-(2-tert-butoxy-1-cyano-2-oxo-ethyl)-6-(trifluoromethyl)pyridine-3-carboxylate (1.80 g, 5.02 mmol) in acetonitrile (36 mL) was added 4-methylbenzenesulfonic acid (874 mg, 5.02 mmol, 1.0 equiv.) at room temperature. The reaction was stirred at 87 °C for 2 hours. After completion of the reaction, the solvent was removed under reduced pressure. Ice-cold water (200 mL) was added, and the mixture was extracted with ethyl acetate (100 mL, twice). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by Combiflash (20% ethyl acetate in cyclohexane) to give 890 mg of ethyl 2-(cyanomethyl)-6-(trifluoromethyl)pyridine-3-carboxylate as a thick, colorless oil. 1 H NMR(400MHz,CDCl3)δ ppm:1.48(t,3H),4.44-4.53(m,4H),7.81(d,1H),8.57(d,1H).

[0612] Step 3: Preparation of 2-(trifluoromethyl)-7,8-dihydro-6H-1,6-naphthyridin-5-one (Intermediate I3) [ka] To a mixture of ethyl 2-(cyanomethyl)-6-(trifluoromethyl)pyridine-3-carboxylate (890 mg, 3.45 mmol) in methanol (10.7 mL) was added cobalt(II) chloride (2.24 g, 17.2 mmol, 5.0 equiv.) at 0° C. Sodium borohydride (408 mg, 1.62 mmol, 3.0 equiv.) was then added portionwise at 0° C. The reaction mixture was then allowed to reach room temperature and stirred at room temperature for 16 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (30 mL). The aqueous layer was extracted with EtOAc (50 mL, 3 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a solid that was purified on a Combiflash using 50% ethyl acetate in cyclohexane to give 350 mg of 2-(trifluoromethyl)-7,8-dihydro-6H-1,6-naphthyridin-5-one as an off-white solid. 1 H NMR(400MHz,CDCl3)δ ppm:3.32(t,2H).3.74(td,2H),6.55(br s,1H)7.73(d,1H)8.53(d,1H).

[0613] Step 4: Preparation of 3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine (Intermediate I4) [ka] Hydrochloric acid in 1,4-dioxane (25 mL, 4.0 mol / L, 101.7 mmol, 10 equivalents) was slowly added to a solution of tert-butyl N-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbamate, as disclosed in WO 2021 / 140122 (4.0 g, 10.17 mmol), in 1,4-dioxane (40.7 mL), and the mixture was heated to 50 °C. After 15 hours, the mixture was concentrated under reduced pressure. The residue was suspended in ethyl acetate, a saturated aqueous solution of sodium bicarbonate was added, and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to give 3.0 g of 3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine, which was used directly in the next step. 1 H NMR(400MHz,DMSO-d6)δ ppm:1.15(t,3H),3.36(q,2H),6.29(broad s,2H),7.25(dd,1H),7.83(d,1H),8.66(d,1H).

[0614] Step 5: Preparation of 2-bromo-3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Intermediate I5) [ka] 3-Ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine (2.5 g, 8.5 mmol) was dissolved in acetic acid (66 mL) under an argon atmosphere. Hydrobromic acid (1.9 mL, 17 mmol, 2 equiv.) was then added dropwise to the reaction mixture within 5 minutes. Sodium nitrite (0.55 mL, 17 mmol, 2 equiv.) was then added portionwise (exothermic). The resulting mixture was stirred at room temperature for 25 minutes. Copper(I) bromide (2.5 g, 17 mmol, 2 equiv.) was added portionwise, and the mixture was stirred at room temperature for 50 minutes. The mixture was poured into ice water, and the resulting aqueous phase was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Methanol was added to the residue and the suspension was filtered to give 1.64 g of 2-bromo-3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine as an orange solid. LCMS (Method 5): Rt=0.99 min, m / z 283 / 285 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm:1.36(t,3H),3.41(q,2H),7.20-7.30(m,1H),8.00(s,1H),9.20(d,1H).

[0615] Step 6: Preparation of 3-ethylsulfonyl-2-fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Intermediate I6) [ka] To a solution of 2-bromo-3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine (680 mg, 1.81 mmol) in DMSO (39.5 mL) was added cesium fluoride (781 mg, 4.88 mmol, 2.70 equiv.) under a nitrogen atmosphere. The reaction mixture was stirred at 105 °C for 2 h. The reaction mixture was cooled to room temperature, ice-cold water (100 mL) was added, and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash chromatography using 0-30% ethyl acetate in cyclohexane to give a solid, which was triturated with methyl tert-butyl ether. The solvent was removed under reduced pressure to give 350 mg of 3-ethylsulfonyl-2-fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine as a white solid. 1 H NMR(400MHz,CDCl3)δ ppm:1.37(t,3H),3.42(q,2H),7.26-7.28(m,1H),8.01(s,1H),9.21(d,1H).

[0616] Step 7: Preparation of 6-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5-one (Compound P.1) [ka] To a solution of 2-(trifluoromethyl)-7,8-dihydro-6H-1,6-naphthyridin-5-one (100 mg, 0.439 mmol) and 3-ethylsulfonyl-2-fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine (151 mg, 0.483 mmol, 1.10 equiv.) in N,N-dimethylformamide (1 mL) was added cesium carbonate (321 mg, 0.967 mmol, 2.20 equiv.), and the mixture was heated at 90° C. for 3 h. The reaction was quenched with ice-cold water (50 mL), and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash chromatography using 0 to 80% ethyl acetate in cyclohexane as eluent to give 103 mg of 6-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5-one as a white solid. LCMS (Method 1): Rt=1.08 min, m / z 493 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm:1.43-1.51(m,4H),3.52-3.67(m,4H),4.28(broad t,2H),7.29-7.32(m,1H),7.77(d,1H),8.05(s,1H),8.59(d,1H),9.04(d,1H).

[0617] [Table 16-1]

[0618] [Table 16-2]

[0619] [Table 16-3]

[0620] The activity of the compositions according to the invention can be significantly broadened and adapted to the prevailing conditions by adding other insecticidal, acaricidal, and / or fungicidal active ingredients. Mixtures of compounds of formula I with other insecticidal, acaricidal, and / or fungicidal active ingredients can also have surprising advantages, which can be broadly described as synergistic activity. For example, better plant resistance, reduced phytotoxicity, insects can be controlled during their production, e.g., during grinding or mixing, their storage, or their use, at different developmental stages, or better behavior. Suitable additives to the active ingredients herein are exemplified by the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thiourea, juvenile hormones, formamidine, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylurea, pyridylmethyleneamino derivatives, macrolides, neonicotinoids, and Bacillus thuringiensis preparations.

[0621] The following combinations of a compound of formula I and another active substance in a 1:1 weight ratio are preferred (the abbreviation "TX" means "one compound selected from the compounds listed in Tables A-1 to A-48, Tables B-1 to B-48, Tables C-1 to C-48, Tables D-1 to D-24, Tables E-1 to E-24, Tables F-1 to F-48 and Tables G-1 to G-48, Tables H-1 to H-6, Tables J-1 to J-6 and Table P of the present invention").

[0622] An adjuvant selected from the group of substances consisting of petroleum (alternative name) (628) + TX; Abamectin +TX, Acequinocyl +TX, Acetamiprid +TX, Acetoprole +TX, Acrinathrin +TX, Acinonapyr +TX, Afidopiropen +TX, Afoxolaner +TX, Alanycarb +TX, Allethrin +TX, α-Cypermethrin +TX, α-Methrin +TX, Amidoflumet +TX, Aminocarb +TX, Azocyclotine +TX, Bensultap +TX, Benzoximate +TX, Benzpyrimoxane +TX, β-Cyfluthrin +TX, β-Cypermethrin +TX, Bifenazate +TX, Bifenthrin +TX, Binapacryl +TX, Bioallethrin +TX, S-Bioallethrin +TX, Bioresmethrin +TX, Bistrifluron +TX, Brofuranilide +TX, Broflutrinate +TX, Bromophos-ethyl +TX, Buprofezin +TX, Butocarboxim +TX, Cadusafos +TX, Carbaryl +TX, Carbosulfan +TX, Cartap +TX, CAS Number: 1632218-00-8 +TX, CAS Number: 1808115-49-2 +TX, CAS Number: 2032403-97-5 +TX, CAS Number: 2044701-44-0 +TX, CAS Number: 212 8706-05-6+TX, CAS number:2095470-94-1+TX, CAS number:2377084-09-6+TX, CAS number:1445683-71-5+TX, CAS number:2408220-94-8+TX, CAS number:2408220-91-5+TX, C AS number: 1365070-72-9+TX, CAS number: 2171099-09-3+TX, CAS number: 2396747-83-2+TX, CAS number: 2133042-31-4+TX, CAS number: 2133042-44-9+TX, CAS number: 1445684-8 2-1+TX, CAS number:1445684-82-1+TX, CAS number:1922957-45-6+TX, CAS number:1922957-46-7+TX, CAS number:1922957-47-8+TX, CAS number:1922957-48-9+TX, CAS number:2 415706-16-8+TX, CAS number: 1594624-87-9+TX, CAS number: 1594637-65-6+TX, CAS number: 1594626-19-3+TX, CAS number: 1990457-52-7+TX, CAS number: 1990457-55-0+TX,CAS No.: 1990457-57-2+TX, CAS No.: 1990457-77-6+TX, CAS No.: 1990457-66-3+TX, CAS No.: 1990457-85-6+TX, CAS No.: 2220132-55-6+TX, CAS No.: 1255091-74-7+TX, CAS No.: 2719848-60-7+TX, CAS No.: 1956329-03-5+TX, Chlorantraniliprole+TX, Chlordane+TX, Chlorfenapyr+TX, Chlorprallethrin+TX, Chromafenozide+TX, Clempirin+TX, Chlorantraniliprole+TX, Chlordane+TX, Chlorfenapyr+TX, Chlorantraniliprole ... Ethocarb + TX, clothianidin + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, cyanofenphos + TX, cyantraniliprole + TX, cyclaniliprole + TX, cyclobutrifluram + TX, cycloprothrin + TX, cycloxapride + TX, cyenopyrafen + TX, cyetopyrafen (or ethopyrafen) + TX, cyflumetofen + TX, cyfluthrin + TX, cyhalodiamide + TX, cyhalothrin + TX, cypermethrin + TX, cyphenothrin + TX, cyprofuranilide + TX, cyromazine + TX, de Rutamethrin + TX, Diafenthiuron + TX, Dialifos + TX, Dibrom + TX, Dichloromethiaz + TX, Diflobidazin + TX, Diflubenzuron + TX, Dimpropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Emamectin (or Emamectin Benzoate) + TX, Empenthrin + TX, Epsilon-Morfluorotrin + TX, Epsilon-Metofluthrin + TX, Efenvalerate + TX, Ethion + TX, Ethiprole + TX, Etofenprox + TX, Etoxa Zol+TX, Famfur+TX, Fenazaquin+TX, Fenfluthrin+TX, Fenmezodithiaz+TX, Fenitrothion+TX, Fenobucarb+TX, Fenothiocarb+TX, Fenoxycarb+TX, Fenpropathrin+TX, Fenpyroximate+TX, Fensulfothion+TX, Fenthion+TX, Fenthion+TX, Fentin acetate+TX, Fenvalerate+TX, Fipronil+TX, Flumetoquin+TX, Flonicamid+TX, Fluacrypyrim+TX, Fluazaindolizine+TX, Frazuron+TX,Flubendiamide +TX, Flubenzimin +TX, Flucriprole +TX, Flucythrinate +TX, Flucycloxuron +TX, Flucythrinate +TX, Fluensulfone +TX, Flufenerim +TX, Flufenprox +TX, Flufiprole +TX, Fluhexafon +TX, Flumethrin +TX, Fluopyram +TX, Flupentiofenox +TX, Flupyradifurone +TX, Flupiroxystrobin +TX, Flupirimine +TX, Fluralaner +TX, Fluvalinate +TX, Fluxamethamide +TX, Fosthiazate +T X, gamma-cyhalothrin +TX, guadipyr +TX, halofenozide +TX, halfenprox +TX, heptafluthrin +TX, hexythiazox +TX, hydramethylnon +TX, imicyafos +TX, imidacloprid +TX, imiprothrin +TX, indazapiroxamet +TX, indoxacarb +TX, iodomethane +TX, iprodione +TX, isocycloceram +TX, isothioate +TX, ivermectin +TX, kappa-bifenthrin +TX, kappa-tefluthrin +TX, lambda-cyhalothrin +TX, redoprona +TX , Lepimectin +TX, Lotilaner +TX, Lufenuron +TX, Metaflumizone +TX, Metaldehyde +TX, Metam +TX, Methomyl +TX, Methoxyfenozide +TX, Metofluthrin +TX, Metolcarb +TX, Mexacarbate +TX, Milbemectin +TX, Mofluorotrin +TX, Niclosamide +TX, Nifluoroprole +TX; Nitenpyram +TX, Nithiazine +TX, Methoate +TX, Oxamyl +TX, Oxazosulfuryl +TX, Parathion-ethyl +TX, Permethrin +TX, Fenothrin +TX, Phosphocarcinoma Rub +TX, piperonyl butoxide +TX, pirimicarb +TX, pirimiphos ethyl +TX, pirimiphos methyl +TX, polyhedrosis virus +TX, prallethrin +TX, profenofos +TX, profluthrin +TX, propargite +TX, propetamphos +TX, propoxa +TX, prothiofos +TX, protrifenbut +, piflubumid +TX, pymetrozine +TX, pyraclofos +TX, pyrafluprole +TX, pyridaben +TX, pyridalyl +TX, pyrifluquinazon +TX, pyrimidifen +TX, pyriminostrobin +TX,Pyriprole +TX, pyriproxyfen +TX, resmethrin +TX, sarolaner +TX, selamectin +TX, silafluorofen +TX, spinetoram +TX, spinosad +TX, spirobudifen +TX; spirodiclofen +TX, spiromesifen +TX, spiropydione +TX, spirotetramat +TX, spidoxamat +TX, sulfoxaflor +TX, tebufenozide +TX, tebufenpyrad +TX, tebupir Miphos + TX, Tefluthrin + TX, Temephos + TX, Tetrachlorantraniliprole + TX, Tetradifon + TX, Tetramethrin + TX, Tetramethylfluthrin + TX, Tetranactin + TX, Tetraniliprole + TX, Theta-cypermethrin + TX, Thiacloprid + TX, Thiamethoxam + TX, Thiocyclam + TX, Thiodicarb + TX, Thiofanox + TX, Thiometon + TX, Thiosultap + TX, Zygo Lana+, thiolanthraniliprole+TX; thioxazaphen+TX, tolfenpyrad+TX, toxaphene+TX, tralomethrin+TX, transfluthrin+TX, triazamate+TX, triazophos+TX, trichlorophon+TX, trichlorophon+TX, trifluenfuronate+TX, triflumezopyrim+TX, tilopyrazofurol+TX, zeta-cypermethrin+TX, seaweed extract and fermentation product derived from Melase+TX, urea+TX, amino acids+TX, seaweed extract and fermentation product derived from Melase containing potassium and molybdenum and EDTA-chelated manganese+TX, seaweed extract and fermented plant product+TX, extract of seaweed and plant fermentation product containing plant hormone+TX, vitamins+TX, vitamins+TX, EDTA-chelated copper+TX, zinc+TX, and iron, azadirachtin+TX, Bacillus aizawaii (Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL accession number B-21664) + TX,Bacillus pumilus (NRRL accession number B-30087) + TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp. AQ178 (ATCC accession number 53522) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, Bacillus subtilis unspecified + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B-50455) + TX, Bacillus subtilis AQ713 (NRRL Accession No. B-21661) + TX, Bacillus subtilis AQ743 (NRRL Accession No. B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL Accession No. B-21530) + TX, Bacillus thuringiensis subspecies kurstaki BMP 123+TX, Beauveria bassiana+TX, D-limonene+TX, Granulovirus+TX, Harpin+TX, Helicoverpa armigera Nucleopolyhedrovirus+TX, Helicoverpa zea Nucleopolyhedrovirus + TX, Heliothis virescens Nucleopolyhedrovirus + TX, Heliothis punctigera Nucleopolyhedrovirus + TX, Metarhizium spp.) + TX, Muscodor albus 620 (NRRL Accession No. B-30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, Neem tree products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usuga usgae + TX, P-cymene + TX, Plutella xylostella Granulosis virus + TX, Plutella xylostella Nucleopolyhedrovirus + TX, Polyhedrosis virus + TX, Pyrethrum + TX, QRD 420 (Terpenoid Blend) + TX, QRD 452 (Terpenoid Blend) + TX, QRD 460 (Terpenoid Blend) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL Accession No. B-21663) + TX, Spodoptera frugiperda Nucleopolyhedrovirus Nucleopolyhedrovirus + TX, Streptomyces galbus (NRRL accession number 30232) + TX, Streptomyces sp. (NRRL accession number 30145) + TX, terpenoid blend + TX, and Verticillium spp. + TX;

[0623] an algicide selected from the group of substances consisting of bethoxadin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dichloron (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) + TX, and triphenyltin hydroxide (IUPAC name) (347) + TX;

[0624] an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, cyclobutrifluram + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, and thiophanate (1435) + TX;

[0625] an avian repellent selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) + TX, and strychnine (745) + TX;

[0626] 1-Hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + TX a fungicide selected from the group of substances consisting of TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX and thiomersal (alternative name) [CCN] + TX;

[0627] Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimiza aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis subsp. israelensis) (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (Bacillus thuringiensis subsp.tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternate name) (53) + TX, Beauveria brongniartii (alternate name) (54) + TX, Chrysoperla carnea (alternate name) (151) + TX, Cryptolaemus montrouzieri (alternate name) (178) + TX, Cydia pomonella GV (alternate name) (191) + TX, Dacnusa sibirica (alternate name) (212) + TX, Diglyphus isaea (alternate name) (254) + TX, Encarsia formosa formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternate name) (300) + TX, Helicoverpa zea NPV (alternate name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternate name) (433) + TX, Hippodamia convergens (alternate name) (442) + TX, Leptomastix dactylopii (alternate name) (488) + TX, Macrolophus caliginosus (alternate name) (491) + TX, Mamestra brassicae brassicae) NPV (alternate name) (494) + TX, Metaphycus helvolus (alternate name) (522) + TX, Metarhizium anisopliae var.acridum (scientific name) (523) + TX, Metarhizium anisopliae var anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternate name) (575) + TX, Orius spp. (alternate name) (596) + TX, Paecilomyces fumosoroseus (alternate name) (613) + TX, Phytoseiulus persimilis (alternate name) (644) + TX, Spodoptera exigua exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternate name) (742) + TX, Steinernema carpocapsae (alternate name) (742) + TX, Steinernema feltiae (alternate name) (742) + TX, Steinernema glaseri (alternate name) (742) + TX, Steinernema riobrave (alternate name) (742) + TX, Steinernema riobravis (alternate name) (742) + TX, Steinernema skapterischii (Steinernema a biological agent selected from the group of substances consisting of Steinernema spp. (alternate name) (742) + TX, Trichogramma spp. (alternate name) (826) + TX, Typhlodromus occidentalis (alternate name) (844) + TX, and Verticillium lecanii (alternate name) (848) + TX.

[0628] a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) + TX and methyl bromide (537) + TX;

[0629] an antisterilizing agent selected from the group of substances consisting of Afolate [CCN] + TX, Visadyl (alternative name) [CCN] + TX, Busulfan (alternative name) [CCN] + TX, Diflubenzuron (250) + TX, Dimatif (alternative name) [CCN] + TX, Hemel [CCN] + TX, Hempa [CCN] + TX, Metepa [CCN] + TX, Methiotepa [CCN] + TX, Methyl Afolate [CCN] + TX, Morzide [CCN] + TX, Penfluron (alternative name) [CCN] + TX, Tepa [CCN] + TX, Thiohempa (alternative name) [CCN] + TX, Thiotepa (alternative name) [CCN] + TX, Tretamine (alternative name) [CCN] + TX, and Uredepa (alternative name) [CCN] + TX;

[0630] (E)-Deca-5-en-1-ol with (E)-dec-5-en-1-yl acetate (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradec-4,10 -dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (436) + TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, ( (Z)-Hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-Eicos-13-en-10-one (IUPAC name) (448) + TX, (Z)-Tetradeca-7-en-1-al (IUPAC name) (782) + TX, (Z)-Tetradeca-9-en-1-ol (IUPAC name) (783) + TX , (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradec-9,12-Dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, Brevicomin (alternative name) [CCN] + TX, Codreria (alternative name) [CCN] + TX, Codlemone (alternative name) (167) + TX, Culer (alternative name) (179) + TX, Dispel (277) + TX, Dodec-8-ene 1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodec-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, Dominical (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, Gossypur® (alternative name; hexadeca-7,11-dien-1-yl acetate (Z, E) 1:1 mixture of (Z,Z) isomer and (Z,Z) isomer) (420) + TX, Granrua (421) + TX, Granrua I (alternative name) (421) + TX, Granrua II (alternative name) (421) + TX, Granrua III (alternative name) (421) + TX, Granrua IV (alternative name) (421) + TX, Hexalua [CCN] + TX, Ipsdienol (alternative name) [CCN] + TX, Ipsenol (alternative name) [CCN] + TX, Japo Nilua (alternative name) (481) + TX, Lineatin (alternative name) [CCN] + TX, Litsua (alternative name) [CCN] + TX, Roopua (alternative name) [CCN] + TX, Medule [CCN] + TX, Megtamoic acid (alternative name) [CCN] + TX, Methyleugenol (alternative name) (540) + TX, Muscalua (563) + TX, Octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, Octadeca-3,an insect hormone selected from the group consisting of 13-dien-1-yl acetate (IUPAC name) (589) + TX, orfalure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramon (alternative name) [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedur (839) + TX, trimedur A (alternative name) (839) + TX, trimedur B1 (alternative name) (839) + TX, trimedur B2 (alternative name) (839) + TX, trimedur C (alternative name) (839) TX, and trunk call (alternative name) [CCN] + TX,

[0631] an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methyl neodecanoamide [CCN] + TX, oxamate [CCN] + TX, and picaridin [CCN] + TX;

[0632] Bis(tributyltin)oxide (IUPAC name) (913) + TX, Bromoacetamide [CCN] + TX, Calcium arsenate [CCN] + TX, Cloetocarb (999) + TX, Copper acetarsenite [CCN] + TX, Copper sulfate (172) + TX, Fentin (347) + TX, Ferric phosphate (IUPAC name) (352) + TX, Metaldehyde (518) + TX, Methiocarb (530) + TX, Nicolasamide (576) + TX, Nicolasamide-olamine (576) + TX, Pentachlorophen a molluscicide selected from the group of substances consisting of benzoyl alcohol (623) + TX, pentachlorophenoxide sodium salt (623) + TX, thazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) + TX, triphenyltin hydroxide (IUPAC name) (347) + TX, and pyriprole [394730-71-3] + TX;

[0633] AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / CAS (chemical abstract name) (1045) + TX, 1,2-dichloropropane (IUPAC / chemical abstract name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, AZ60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloetocarb (999) + TX, cyclobutrifluram + TX, cytokinin (alternative name) (210) + TX, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidaphos (1044) + TX, Diclofenthion (1051) + TX, Diglychos (alternative name) + TX, Dimethoate (262) + TX, Doramectin (alternative name) [CCN] + TX, Emamectin (291) + TX, Emamectin Benzoate (291) + TX, Eprinomectin (alternative name) [CCN] + TX, Ethoprophos (312) + TX, Ethylenedibromide Do (316) + TX, Fenamiphos (326) + TX, Fenpyrad (alternative name) + TX, Fensulfothion (1158) + TX, Fosthiazate (408) + TX, Fostietan (1196) + TX, Furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, Heterofos [CCN] + TX, Iodomethane (IUPAC name) (542) + TX, Isoamidophos (1230) + TX, Isoazophos (1231) + TX, Iber Mectin (alternative name) [CCN] + TX, Kinetin (alternative name) (210) + TX, Mecarfone (1258) + TX, Metam (519) + TX, Metapotassium (alternative name) (519) + TX, Meta-sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alternative name) [CCN] + TX, Moxidectin (alternative name) [CCN] + TX, Myrothecium verrucariaverrucaria) Composition (alternative name) (565) + TX, NC-184 (compound code) + TX, Oxamyl (602) + TX, Phorate (636) + TX, Phosphoamidon (639) + TX, Phosphocarb [CCN] + TX, Cebufos (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbam (alternative name) + TX, Terbufos (773) + TX, Tetrachlorothiophene (IUP a nematicide selected from the group consisting of AC / Chemical Abstracts Name) (1422) + TX, Thiafenox (alternative name) + TX, Thionazine (1434) + TX, Triazophos (820) + TX, Triazuron (alternative name) + TX, Xylenol [CCN] + TX, YI-5302 (compound code) + TX, Zeatin (alternative name) (210) + TX, Fluensulfone [318290-98-1] + TX, and Fluopyram + TX;

[0634] a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] + TX and nitrapyrin (580) + TX;

[0635] a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) + TX, and Reynoutria sachalinensis extract (alternative name) (720) + TX;

[0636] 2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenic oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodiphasm (89) + TX, bromodiolone (including alpha-bromodiolone) + TX , Bromomethalin (92) + TX, Calcium cyanide (444) + TX, Chloralose (127) + TX, Chlorophacinone (140) + TX, Cholecalciol (alternative name) (850), Coumachlor (1004) + TX, Coumafuryl (1005) + TX, Coumatetralyl (175) + TX, Crimidine (1009) + TX, Difenacoum (246) + TX, Difethialone (249) + TX, Diphacinone (273) + TX, Ergocalciferol (301) + TX, Flocoumafen ( 357) + TX, fluoroacetamide (379) + TX, flupropazine (1183) + TX, flupropazine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, fosacetin (1336) + TX, phosphine (I a rodenticide selected from the group of substances consisting of (UPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) + TX, and zinc phosphide (640) + TX;

[0637] a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol and nerolidol (alternative names) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piperotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesamolin (1394) + TX, and sulfoxide (1406) + TX;

[0638] an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetate (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] + TX, and ziram (856) + TX;

[0639] antiviral agents selected from the group of substances consisting of Imanin (alternative name) [CCN] and Ribavirin (alternative name) [CCN] + TX;

[0640] a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) + TX, and thiophanate-methyl (802) + TX;

[0641] Bioactive substances selected from the following: 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenylsulfone + TX, acetoprole + TX, aldoxylcarb + TX, amidothione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic oxide + TX, azobenzene + TX, azothioate + TX, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromosylene + TX, bromophos + TX, Bromopropylate +TX, Buprofezin +TX, Butocarboxim +TX, Butoxycarboxim +TX, Butylpyridaben +TX, Calcium Polysulfide +TX, Camphechlor +TX, Carbanolate +TX, Carbophenothion +TX, Cimiazole +TX, Chinomethionate +TX, Chlorbeside +TX, Chlordimeform +TX, Chlordimeform Hydrochloride +TX, Chlorphenetole +TX, Chlorfenson +TX, Chlorphenesulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cineline I +TX, Cineline II+TX, Synerins+TX, Closantel+TX, Coumaphos+TX, Crotamiton+TX, Crotoxyphos+TX, Kufraneb+TX, Cyansoate+TX, DCPM+TX, DDT+TX, Demefion+TX, Demefion-O+TX, Demefion-S+TX, Demeton-methyl+TX, Demeton-O+TX, Demeton-O-methyl+TX, Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-Diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopen+TX, Dinosulfone+TX, Dinoterbon+TX Dioxathione +TX, Diphenylsulfone +TX, Disulfiram +TX, DNOC +TX, Dofenapine +TX, Doramectin +TX, Endothion +TX, Eprinomectin +TX, Ethoate Methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin Oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxone +TX, Furnetyl +TX, Fluobenside +TX, FMC 1137 +TX, Formetanate +TX, Formetanate Hydrochloride +TX, Folparanate +TX, Gamma-HCH +TX, Gliodin +TX, Halfenprox +TX, Hexadecylcyclopropanecarboxylate +TX, Isocarbofos +TX, Jasmolin I +TX, Jasmolin II+TX, Iodofenphos+TX, Lindane+TX, Malonoben+TX, Mecarbam+TX, Mefosfolan+TX, Mesulfen+TX, Metoacrifos+TX, Methylbromide+TX, Metolcarb+TX, Mexacarbate+TX, Milbemycin oxime+TX, Mipafox+TX, Monocrotophos+TX, Morphothion+TX, Moxidectin+TX, Naled+TX, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one+TX, Nifluridide+TX, Nikomicin+TX, Nitrilacarb+TX, Nitrilacarb 1:1 Zinc chloride complex +TX, omethoate +TX, oxydeprofos +TX, oxydisulfon +TX, PP'-DDT +TX, parathion +TX, permethrin +TX, fencapto +TX, phosalone +TX, phosphorane +TX, phosphamidon +TX, polychloroterpenes +TX, polynactin +TX, proclonol +TX, promacyl +TX, propoxur +TX, protidathion +TX, prothoate +TX, pyrethrin I +TX, pyrethrinsII+TX, pyrethrins+TX, pyridaphenthion+TX, pirimitate+TX, quinalphos+TX, quinthiophos+TX, R-1492+TX, phosglycine+TX, rotenone+TX, shladan+TX, cebufos+TX, selamectin+TX, sofamid+TX, SSI-121+TX, sulfiram+TX, sulfuramide+TX, sulfotep+TX, sulfur+TX, diflovidazin+TX, tau-fluvalic acid+TX, TEPP+TX, terbam+TX, tetradifon+TX, tetrasul+TX, thiafenox+TX, thiocarboxim+TX, thiofanox+TX, Thiometon + TX, Thioquinox + TX, Turingiensin + TX, Triamiphos + TX, Triaratene + TX, Triazophos + TX, Triazuron + TX, Trifenofos + TX, Trinactin + TX, Vamidothion + TX, Vaniliprole + TX, Bethoxazin + TX, Copper dioctanoate + TX, Copper sulfate + TX, Sibutrin + TX, Dichlorn + TX, Dichlorophen + TX, Endothal + TX, Fentin + TX, Hydrated lime + TX, Nabam + TX, Quinoclamine + TX, Quinonamide + TX, Simazine + TX, Triphenyltine Acetate + TX, Triphenyltine Hydroxide + TX, Clfomate + TX, Piperazine + TX, Thiophanate + TX, Chloralose + TX, Fenthion + TX, Pyridin-4-amine + TX, Strychnine + TX, 1-Hydroxy-1H-pyridine-2-thione + TX, 4-(Quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-Hydroxyquinoline Sulfate + TX, Bronopol + TX, Copper Hydroxide + TX, Cresol + TX, Dipyrithione + T X, Dojicin + TX, Fenaminosulf + TX, Formaldehyde + TX, Hydralgafen + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Nickel bis(dimethyldithiocarbamate) + TX, Nitrapyrin + TX, Octilinone + TX, Oxolinic acid + TX, Oxytetracycline + TX, Potassium hydroxyquinoline sulfate + TX, Probenazole + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Tecloftalam + TX, Thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp.) + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella pomonella)GV+TX, Dacnusa sibirica (Dacnusa sibirica)+TX, Diglyphus. Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopilae anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp.) + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii lecanii) + TX, afolate + TX, Visadil + TX, busulfan + TX, Dimatif + TX, Hemel + TX, Hemp + TX, Metepa + TX, methiotepa + TX, methyl afolate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohep + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, ( (Z)-Hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icosa-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX. , 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, α-multistritin + TX, Brevicomin + TX, Codrel + TX, Codlemone + TX, Curel + TX, Disparl + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8 + TX, 10-dien-1-yl acetate + TX, Dominicalule + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grand Rule + TX, Grand Rule I + TX, Grand Rule II + TX, Grand Rule III + TX, Grand Rule IV+TX, Hexalur+TX, Ipsidienol+TX, Ipsenol+TX, Japonirur+TX, Lineatin+TX, Littlea+TX, Loopa+TX, Medore+TX, Megatomoic Acid+TX, Methyleugenol+TX, Musca+TX, Octadeca-2,13-dien-1-yl Acetate+TX, Octadeca-3,13-dien-1-yl Acetate+TX, Olflaa+TX, Orictaa+TX, Ostramon+TX, Siglar+TX, Soldidine+TX, Sulcatol+TX, Tetradec-11-en-1-yl Acetate+TX, Trimedlar+TX, Trimedlar A+TX, Trimedlar B1+TX, Trimedlar B2+TX, Trimedlar C+TX, Trunkcoal+TX, 2-(octylthio)ethanol+TX, Butopyronoxy+TX, Butoxy(polypropylene glycol)+TX, Dibutyl adipate+TX, Dibutyl phthalate+TX, Dibutyl succinate+TX, Diethyl toluamide+TX, Dimethyl carbamate+TX, Dimethyl phthalate+TX, Ethyl hexanediol+TX, Hexamide+TX, Butyl methoxide+TX, Methyl neodecanoate+TX, Oxamate+TX, Picaridin+TX, 1-Dichloro-1-nitroethane+TX, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane+TX, 1,2-Dichloropropane and 1,3-Dichloropropene+TX, 1-Bromo-2-chloroethane+TX, 2,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetate+TX, 2,2-Dichlorovinyl2-Ethylsulfinylethylmethylphosphate + TX, 2-(1,3-dithiolan-2-yl)phenyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethylthiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxalan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyldiethylphosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(propynyl)aminophenylmethylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloropropylene + TX, 3-methyl-1-phenyl Nylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(propynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohexen-1-yldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixycarb + TX, alpha-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis deltaendotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartholin + TX, Bayer 22 / 190 + TX, Bayer22408+TX, beta-cyfluthrin+TX, beta-cypermethrin+TX, bioethanomethrin+TX, biopermethrin+TX, bis(2-chloroethyl)ether+TX, borax+TX, bromfenvinphos+TX, bromo-DDT+TX, bufencarb+TX, butacarb+TX, butathiophos+TX, butonate+TX, calcium arsenate+TX, calcium cyanide+TX, carbon disulfide+T X, carbon tetrachloride +TX, carthap hydrochloride +TX, sevadin +TX, chlorbicyclen +TX, chlordane +TX, chlordecone +TX, chloroform +TX, chloropicrin +TX, chlorfoxime +TX, chlorprazophos +TX, cis-resmethrin +TX, cismethrin +TX, clocitrin +TX, copper acetoarsenite +TX, copper arsenate +TX, copper oleate +TX, chmithofoate +TX, cryolite +TX, CS 708+TX, Cyanfenphos+TX, Cyanphos+TX, Cycloethrin+TX, Sithioate+TX, d-Tetramethrin+TX, DAEP+TX, Dazomet+TX, Decarbofluan+TX, Diamidaphos+TX, Dicafuton+TX, Diclofenthion+TX, Dicresyl+TX, Dicycloanil+TX, Dieldrin+TX, Diethyl 5-methylpyrazol-3-yl phosphate+TX, Dilor+TX, Dimefluthrin+TX, Dimethana+TX, Dimethrin+TX, Dimethylvinphos+TX, Dimethylan+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX, Diofenolan+TX, Dioxabenzophos+TX, Dicyclofos+TX, DSP+TX, Ecdysterone+TX, EI1642+TX, EMPC+TX, EPBP+TX, Ethaphos+TX, Ethiofencarb+TX, Ethyl Formate+TX, Ethylene Dibromide+TX, Ethylene Dichloride+TX, Ethylene Oxide+TX, EXD+TX, Fenchlorphos+TX, Fenetacarb+TX, Fenitrothion+TX, Fenoxacrim+TX, Fenpyrithrin+TX, Fensulfothion+TX, Fenthion Ethyl+TX, Flucofluron+TX, Fosmetilan+TX, Fospirate+TX, Fostietan+T X, Fluathiocarb +TX, Fluethrin +TX, Guazatine +TX, Guazatine acetate +TX, Sodium tetrathiocarbonate +TX, Halfenprox +TX, HCH +TX, HEOD +TX, Heptachlor +TX, Heterofos +TX, HHDN +TX, Hydrogen cyanide +TX, Hiquincarb +TX, IPSP +TX, Isazophos +TX, Isobenzane +TX, Isodrin +TX, Isofenphos +TX, Isolane +TX, Isoprothiolane +TX, Isosathion +TX, Juvenile hormone I +TX, Juvenile hormone II +TX, Juvenile hormone III+TX, Kelevan+TX, Kinoprene+TX, Lead arsenate+TX, Leptophos+TX, Lilimphos+TX, Ritidathion+TX, m-cumenyl methylcarbamate+TX, Magnesium phosphide+TX, Magidox+TX, Mecarfone+TX, Menasone+TX, Mercury chloride+TX, Mesulfenphos+TX, Metam+TX, Metam-potassium+TX, Metam-sodium+TX, Methanesulfonyl fluoride methionine + TX, methocrotophos + TX, methoprene + TX, methrin + TX, methoxychlor + TX, methyl isothiocyanate + TX, methyl chloroform + TX, methylene chloride + TX, methoxyazizone + TX, Mirex + TX, naphthalophos + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, nornicotine + TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-diethylO-6-Methyl-2-propylpyrimidin-4-yl phosphorothioate +TX, O,O,O',O'-Tetrapropyldithiopyrophosphate +TX, Oleic acid +TX, Paradichlorobenzene +TX, Parathion methyl +TX, Pentachlorophenol +TX, Pentachlorophenyl laurate +TX, PH 60-38 +TX, Fencapto +TX, Phosnichlor +TX, Phosphine +TX, Phoxim methyl +TX, Pyrimetaphos +TX, Polychlorodicyclopentadiene isomers +TX, Potassium arsenite +TX, Potassium thiocyanate +TX, Precocene I +TX, Precocene II +TX, PrecoceneIII+TX, Primidophos+TX, Profluthrin+TX, Promecarb+TX, Prothiofos+TX, Pyrazophos+TX, Pyresmethrin+TX, Quasia+TX, Quinalfos-methyl+TX, Quintion+TX, Lafoxanide+TX, Resmethrin+TX, Rotenone+TX, Cadetrin+TX, Llania+TX, Llanodine+TX, Sabadilla+TX, Shradan+TX, Cebufos+TX, SI-0009+TX, Tiapronil+TX, Sodium Al Senite +TX, Sodium Cyanide +TX, Sodium Fluoride +TX, Sodium Hexafluorosilicate +TX, Sodium Pentachlorophenoxide +TX, Sodium Selenate +TX, Sodium Thiocyanate +TX, Sulcofluron +TX, Sulcofluron Sodium +TX, Sulfuryl Fluoride +TX, Sulprofos +TX, Tall Oil +TX, Thazimcarb +TX, TDE +TX, Tebupirimfos +TX, Temephos +TX, Teraletrin +T X, tetrachloroethane +TX, cyclophos +TX, thiocyclam +TX, thiocyclam hydrogen oxalate +TX, thionazine +TX, thiosultap +TX, thiosultap sodium +TX, tralomethrin +TX, transpermethrin +TX, triazamate +TX, trichlormethaphos-3 +TX, trichloronath +TX, trimethocarb +TX, tolprocarb +TX, triclopyricarb +TX, triplenone +TX, veratridine +TX, veratrine +T X, XMC + TX, zetametrin + TX, zinc phosphide + TX, zolaprofos + TX, meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, iron phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-Methyl-6-thioxo-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, anicifluprine + TX, benclothiazine + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, Myrothecium verrucaria verrucaria) extract +TX, tetrachlorothiophene +TX, xylenol +TX, zeatin +TX, potassium ethylxanthate +TX, acebenzole +TX, acebenzole-S-methyl +TX, giant knotweed extract +TX, alpha-chlorohydrin +TX, antu +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafluyl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocumafen +TX, fluoroacetamide +TX, flupropazine +TX, flupropazine hydrochloride +TX, norbormide +TX, fosacetim +TX, lin +TX, pindone +TX, pyrinuron +TX, siriocide +TX, sodium fluoroacetate +TX, thallium sulfate +TX, warfarin +TX, -2-(2-butoxyethoxy)ethyl piperonylate +TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone +TX, farnesol and nerolidol +TX, berubutin +TX, MGK 264+TX, piperonyl butoxide+TX, piprotal+TX, propyl isomer+TX, S421+TX, sesamex+TX, sesamolin+TX, sulfoxide+TX, anthraquinone+TX, copper naphthenate+TX, copper oxychloride+TX, dicyclope...

Claims

1. Formula (I) 【Chemistry 1】 (In the formula, G 1 is C-R 2a or N, R 2 is a halogen, C 1 ~C 6 Haloalkyl, C 1 ~C 4 Haloalkylsulfanyl, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 4 Haloalkylsulfonyloxy or C 3 ~C 6 cycloalkyloxy; R 2a is hydrogen, or R 2a is R 2 together with the group —O—CF 2 forming —O—; Q is a group of the formula Qa, Qb, Qc, Qd and Qe 【Chemistry 2】 is a group selected from the group consisting of wherein the arrow represents the point of attachment to the nitrogen atom of the bicyclic or tricyclic ring; and A represents CH or N; X is S, SO, or SO 2 and R 1 is C 1 ~C 4 Alkyl or C 3 ~C 6 Cycloalkyl-C 1 ~C 4 is alkyl; Q 1 is hydrogen, halogen, C 1 ~C 6 Haloalkyl, C 3 ~C 6 C monosubstituted by cycloalkyl, cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 1 ~C 6 Cyanoalkoxy, C 1 ~C 6 haloalkoxy, —N(R 4 ) 2 , -N(R 4 ) C(=O)R 5 , -N(R 4 ) CON (R 4 ) 2 , (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q 1 is a 5- to 6-membered aromatic ring system linked via a ring carbon atom to a ring containing the substituent A, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; and the ring system may contain 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the ring system may contain no more than one ring oxygen atom and may contain no more than one ring sulfur atom; or Q 1 is a 5-membered aromatic ring system linked via a ring nitrogen atom to a ring containing a substituent A, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; and said ring system contains 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, wherein said ring system contains at least one ring nitrogen atom and optionally contains no more than one ring oxygen atom and optionally contains no more than one ring sulfur atom; R 3 is hydrogen, halogen or C 1 ~C 4 is alkyl; Each R 4 are independently hydrogen, C 1 ~C 4 Alkyl or C 3 ~C 6 is cycloalkyl; R 5 is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl or C 3 ~C 6 is cycloalkyl, R 6 is C 1 ~C 4 is alkyl, R 7 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C monosubstituted by cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, —CO(NR 4 ) 2 , -NR 4 COR 5 , C 3 ~C 6 Cycloalkyl-C 1 ~C 6 Alkyl, cyano-C 1 ~C 6 C monosubstituted by alkyl 3 ~C 6 cycloalkyl, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or R 7 is a substituent R 6 and a 5- to 6-membered saturated, partially saturated or aromatic ring system linked via a ring nitrogen atom to an imidazole ring comprising 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; 3 ~C 6 Cycloalkyl, C monosubstituted by cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 3 ~C 6 Cycloalkyl-C 1 ~C 6 Alkyl, cyano-C 1 ~C 6 C monosubstituted by alkyl 3 ~C 6 is cycloalkyl, wherein the ring system contains 1, 2, or 3 ring heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the ring system contains at least one ring nitrogen atom and may contain no more than one ring oxygen atom and may contain no more than one ring sulfur atom; or R 7 is a substituent R 6 and a 5- to 6-membered saturated, partially saturated or aromatic ring system linked via a ring carbon atom to an imidazole ring comprising 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl; 3 ~C 6 Cycloalkyl, C monosubstituted by cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 cyanoalkyl, (C 3 ~C 6 ) cycloalkyl-(C 1 ~C 6 ) alkyl-, cyano-(C 1 ~C 6 ) alkyl-monosubstituted (C 3 ~C 6 ) cycloalkyl, wherein the ring system can contain 1, 2, or 3 ring heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, and wherein the ring system can contain no more than one ring oxygen atom and can contain no more than one ring sulfur atom; R 8 and R 9 are each independently hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C monosubstituted by cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 1 ~C 6 Cyanoalkoxy, cyano, C 1 ~C 4 Alkoxy, C 1 ~C 6 haloalkoxy, —N(R 4 ) 2 or -N(R 4 ) C(=O)R 5 , -N(R 4 ) CON (R 4 ) 2 , (oxazolidin-2-one)-3-yl or 2-pyridyloxy, or R 8 and R 9 are each independently hydrogen or a 5- to 6-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring carbon atom, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl, wherein the ring system can contain 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and wherein the ring system can contain no more than one ring oxygen atom and no more than one ring sulfur atom; R 8 or R 9 is hydrogen; or R 8 and R 9 are, independently of one another, hydrogen or a 5-membered aromatic ring system linked to the imidazo[1,2-a]pyridine ring Qd via a ring nitrogen atom, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl, wherein the ring system contains 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and wherein the ring system contains at least one ring nitrogen atom and optionally contains no more than one ring oxygen atom and no more than one ring sulfur atom; 8 or R 9 one of which is hydrogen; R 10 and R 11 are each independently hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C monosubstituted by cyano 3 ~C 6 Cycloalkyl, C 1 ~C 6 Cyanoalkyl, C 1 ~C 6 Cyanoalkoxy, cyano, C 1 ~C 4 Alkoxy, C 1 ~C 6 haloalkoxy, —N(R 4 ) 2 or -N(R 4 ) C(=O)R 5 , -N(R 4 ) CON (R 4 ) 2 , (oxazolidin-2-one)-3-yl or 2-pyridyloxy, or R 10 and R 11 are, independently of one another, hydrogen or a 5- to 6-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring carbon atom, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl, wherein the ring system can contain 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and wherein the ring system can contain no more than one ring oxygen atom and no more than one ring sulfur atom; R 10 or R 11 is hydrogen; or R 10 and R 11 are, independently of one another, hydrogen or a 5-membered aromatic ring system linked to the pyrazolo[1,5-a]pyridine ring Qe via a ring nitrogen atom, said ring system being unsubstituted or substituted with halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl and C 1 ~C 4 alkylsulfonyl, wherein the ring system contains 1, 2, or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and wherein the ring system contains at least one ring nitrogen atom and optionally contains no more than one ring oxygen atom and no more than one ring sulfur atom; 10 or R 11 wherein one of is hydrogen, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.

2. Formula I-A1 【Transformation 3】 (In the formula, A, R 1 , R 2 , R 3 , X, Q 1 , R 4 and R 5 is as defined under formula I of claim 1), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A1.

3. Formula I-A2 【Chemistry 4】 (In the formula, A, R 1 , R 2 , R 3 , X, Q 1 , R 4 and R 5 is as defined under formula I of claim 1), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A2.

4. Formula I-A3 【Transformation 5】 (In the formula, R 1 , R 2 , X, R 4 , R 5 , R 6 and R 7 is as defined under formula I of claim 1), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A3.

5. Formula I-A4 【Transformation 6】 (In the formula, R 1 , R 2 , X, R 4 , R 5 , R 8 and R 9 is as defined under formula I of claim 1), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A4.

6. Formula I-A5 【Transformation 7】 (In the formula, R 1 , R 2 , X, R 4 , R 5 , R 10 and R 11 is as defined under formula I of claim 1), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-A5.

7. Formula I-B1 【Transformation 8】 (In the formula, A, R 1 , R 2 , R 3 , X, Q 1 , R 4 and R 5 is as defined under formula I of claim 1), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-B1.

8. Formula I-B2 【Chemistry 9】 (In the formula, A, R 1 , R 3 , X, Q 1 , R 4 and R 5 is as defined under formula I of claim 1), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I-B2.

9. A is N; X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; and Q 1 is hydrogen, halogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro, cyano or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 9. A compound of formula I according to any one of claims 1, 2, 3, 7 or 8, wherein is either methyl, ethyl or cyclopropyl.

10. R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 A compound of formula I according to any one of claims 1 to 7, wherein

11. X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 and R 6 is C 1 ~C 4 alkyl, preferably R 6 is methyl; and R 7 is an N-linked pyrazolyl optionally monosubstituted by hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoroethoxy, chloro or trifluoromethyl, or R 7 is N-linked triazolyl, C-linked pyrimidinyl, phenyl, optionally monosubstituted with halogen, trifluoromethyl, cyclopropyl, or cyano-cyclopropyl; or R 7 is -N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 5. A compound of formula I according to claim 1 or 4, wherein is either methyl, ethyl or cyclopropyl.

12. X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 and R 6 is C 1 ~C 4 alkyl, preferably R 6 is methyl; and R 8 is H and R 9 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 10. A compound of formula I according to claim 1 or 5, wherein is either methyl, ethyl or cyclopropyl.

13. X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 and R 6 is C 1 ~C 4 alkyl, preferably R 6 is methyl; and R 9 is H and R 8 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 10. A compound of formula I according to claim 1 or 5, wherein is either methyl, ethyl or cyclopropyl.

14. X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 and R 6 is C 1 ~C 4 alkyl, preferably R 6 is methyl; and R 10 is H and R 11 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 10. A compound of formula I according to claim 1 or 6, wherein is either methyl, ethyl or cyclopropyl.

15. X is S or SO 2 and R 1 is ethyl or cyclopropylmethyl; R 2 But, -OSO 2 CF 3 , S.O. 2 CF 3 , -OCF 3 , C.F. 2 CF 3 , halogen, cyclopropyloxy, —OCH 2 CF 2 Cl-, OCH 2 CF 2 CF 2 H, -OCH 2 CF 2 CF 3 , -OCH 2 CCl 2 CF 3 , -OCH 2 CCl 3 or CF 3 and preferably, R 2 is CF 3 or OCF 3 and R 6 is C 1 ~C 4 alkyl, preferably R 6 is methyl; and R 11 is H and R 10 is halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, (oxazolidin-2-one)-3-yl, 2-pyridyloxy, phenyl optionally monosubstituted with halogen, N-linked pyrazolyl optionally monosubstituted with chloro or trifluoromethyl, N-linked triazolyl, C-linked pyrimidinyl, —N(R 4 ) 2 , -N(R 4 ) COR 5 or -N(R 4 ) CON (R 4 ) 2 wherein R 4 are each independently either hydrogen or methyl, and R 5 10. A compound of formula I according to claim 1 or 6, wherein is either methyl, ethyl or cyclopropyl.

16. 6-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-5-one (Compound P1); 1-[5-ethylsulfonyl-6-[1-oxo-6-(trifluoromethyl)-3,4-dihydroisoquinolin-2-yl]-3-pyridyl]cyclopropane-carbonitrile (Compound P2); 1-[5-ethylsulfonyl-6-[5-oxo-2-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin -6-yl]-3-pyridyl]cyclopropane-carbonitrile (Compound P3); 1-[5-ethylsulfonyl-6-[1-oxo-6-(trifluoromethoxy)-3,4-dihydroisoquinolin-2-yl]-3-pyridyl]cyclopropane-carbonitrile (Compound P4); 1-[5-ethylsulfonyl-6-[5-oxo-2-(1,1,2,2,2-pentafluoroethyl)-7,8-dihydro-1,6-naphthyridin-6-yl]-3-pyridyl]cyclopropane-carbonitrile (Compound P5); 1-[6-(2,2 -difluoro-6-oxo-8,9-dihydro-[1,3]dioxolo[4,5-f]isoquinolin-7-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropane-carbonitrile (compound P6); 1-[6-[2-(cyclopropoxy)-5-oxo-7,8-dihydro-1,6-naphthyridin-6-yl]-5-ethylsulfonyl-3-pyridyl]cyclopropane-carbonitrile (compound P7); 1-[6-(2-chloro-5-oxo-7,8-dihydro-1,6-naphthyridin-6-yl)-5-ethylsulfonyl -3-pyridyl]cyclopropane-carbonitrile (compound P8); 1-[6-[2-(2-chloro-2,2-difluoro-ethoxy)-5-oxo-7,8-dihydro-1,6-naphthyridin-6-yl]-5-ethylsulfonyl-3-pyridyl]cyclopropane-carbonitrile (compound P9); 1-[5-ethylsulfonyl-6-[5-oxo-2-(2,2,3,3-tetrafluoropropoxy)-7,8-dihydro-1,6-naphthyridin-6-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P10);1-[5-ethylsulfonyl-6-[5-oxo-2-(2,2,2-trichloroethoxy)-7,8-dihydro-1,6-naphthyridin-6-yl]-3-pyridyl]cyclopropane-carbonitrile (compound P11); 1-[5-ethylsulfonyl-6-[5-oxo-2-(2,2,3,3,3-pentafluoropropoxy)-7,8-dihydro-1,6-naphthyridin-6-yl]cyclopropane-carbonitrile 1-[6-[2-(2,2-dichloro-3,3,3-trifluoro-propoxy)-5-oxo-7,8-dihydro-1,6-naphthyridin-6-yl]-5-ethylsulfonyl-3-pyridyl]cyclopropane-carbonitrile (compound P12); 1-[6-[2-(2,2-dichloro-3,3,3-trifluoro-propoxy)-5-oxo-7,8-dihydro-1,6-naphthyridin-6-yl]-5-ethylsulfonyl-3-pyridyl]cyclopropane-carbonitrile (compound P13);

17. 17. A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) according to any one of claims 1 to 16 or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, and optionally an auxiliary or diluent.

18. 19. A method for combating and controlling insects, acaridae, nematodes or molluscs, which method comprises applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 16 or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition as defined in claim 17.

19. 20. A method for protecting plant propagation material from attack by insects, mites, nematodes or mollusks, comprising treating the propagation material or the locus where the propagation material is planted with the composition of claim 17.

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