Heterocyclic derivatives containing sulfur substituents that are biologically active in harm control.

Abstract

Equation (I) [Formula 1] JPEG2026510442000063.jpg32150 (wherein the formula, the substituents are as defined in claim 1) The present invention relates to a compound of formula (I), a pesticide composition comprising the compound of formula (I), the preparation of these compositions, and the use of the compound or composition in agriculture or horticulture for the control, prevention or control of animal pests, including arthropods and especially insects, mollusks, nematodes, or representative mites (Acarina).

Description

Technical Field

[0001] The present invention relates to pesticidally active, especially insecticidally active heterocyclic derivatives containing a sulfur substituent, a process for their preparation, compositions containing these compounds and their use for controlling animal pests including arthropods and especially insects or representative Acarina.

Background Art

[0002] Heterocyclic derivatives containing a sulfur substituent are known and are described, for example, in WO 2019 / 131575, WO 2019 / 131587, WO 2020 / 158889, WO 2020 / 171077, WO 2020 / 203763, WO 2021 / 141106, WO 2020 / 178789 and WO 2021 / 033141.

[0003] Surprisingly, it has now been found that certain novel sulfur-containing phenyl and pyridyl derivatives attached to the (aza)chromenone moiety have favorable properties as pesticidal agents.

Summary of the Invention

Means for Solving the Problems

[0004] The present invention thus relates to a compound of formula I

Chemical Formula

[0005] The present invention also provides agriculturally acceptable salts, stereoisomers, enantiomers, tautomers, and N-oxides of the compound of formula I. [Modes for carrying out the invention]

[0006] Compounds of formula I having at least one basic center can, for example, form acid addition salts with strong inorganic acids, such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrite, phosphorus-containing acids, and hydrohalic acids; with strong organic carboxylic acids, such as unsubstituted or halogen-substituted C1-C4 alkane carboxylic acids, such as acetic acid; with saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, and phthalic acid; with hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, and citric acid; or with organic sulfonic acids, such as unsubstituted or halogen-substituted C1-C4 alkanes or aryl sulfonic acids, such as methane or p-toluenesulfonic acid. Compounds of formula I having at least one acidic group can form salts with a base, 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 compound of formula (I) according to the present invention is in the form of a free form, an oxidized form as an N-oxide, or a salt form such as an agriculturally usable salt form.

[0008] N-oxides are oxidation forms of tertiary amines or nitrogen-containing heteroaromatic compounds. These are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0009] The compound of formula I according to the present invention also includes hydrates that may be formed during salt formation.

[0010] When it is stated that a substituent itself is further substituted, this means that it has one or more identical or different substituents, e.g., 1 to 4 substituents. Typically, three or fewer such substituents are present simultaneously. Preferably, two or fewer such substituents are present simultaneously (i.e., the group is substituted with one or two of the described substituents). If the additional substituent is a larger group such as a cycloalkyl or phenyl, it is most preferable that only one of these substituents is present. When it is indicated that one group is substituted (e.g., alkyl), this includes these groups that are part of the other group (e.g., alkyl in alkylthio).

[0011] As used herein, the term "aryl" refers to an unsaturated aromatic carbocyclic group containing 6 to 10 ring carbon atoms, having a single ring (e.g., phenyl) or multiple condensed (fused) rings, at least one of which is aromatic (e.g., indanyl, naphthyl). Preferred aryl groups include phenyl, naphthyl, etc., which may be optionally substituted with up to three substituents.

[0012] As used herein, "C1~C n The term "alkyl" refers to any one of the following saturated linear or branched hydrocarbon groups having 1 to n carbon atoms and bonded by any of the carbon atoms, such as 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.

[0013] 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 described above), where some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., 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. Therefore, the term "C1-C2-fluoroalkyl" refers to a C1-C2-alkyl group having 1, 2, 3, 4, or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl.

[0014] As used herein, "C1~C nThe term "alkoxy" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms bonded via an oxygen atom (as described above), namely, for example, one of methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0015] As used herein, "C1~C n The term "haloalkoxy" refers to the above C1-C atoms that are partially or completely substituted with fluorine, chlorine, bromine, and / or iodine. n This refers to alkoxy groups, namely, 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 It is one of the following: 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.

[0016] As used herein, "C1~C nThe term "alkylsulfanyl" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as described above) bonded through a sulfur atom, i.e., for example, any one of methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio.

[0017] As used herein, "C1-C" n The term "alkylsulfinyl" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as described above) bonded through the sulfur atom of a sulfinyl group, i.e., for example, any one of methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl or 1-ethylpropylsulfinyl.

[0018] As used herein, "C1-C" n The term "alkylsulfonyl" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as described above) bonded through the sulfur atom of a sulfonyl group, i.e., for example, any one of methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or t-butylsulfonyl.

[0019] As used herein, "C1-C" n The term "haloalkylsulfanyl" refers to the above C1-C which is partially or completely substituted with fluorine, chlorine, bromine and / or iodine. nThis refers to alkylthio groups, such as 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, and 2-chloro It is one of the following: 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.

[0020] "C1~C n "Haloalkylsulfinyl" and "C1~C n The term "haloalkylsulfonyl" refers to the above-mentioned groups, but each having sulfur in oxidation state 1 or 2.

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

[0022] "C1~C nThe term "cyanoalkoxy" refers to the above-mentioned group, but one that is bonded via an oxygen atom.

[0023] "C3~C n The suffix "-C1~C" follows terms such as "cycloalkyl". n Alkyl (where n is an integer from 1 to 6) is used herein as C3 to C n This refers to linear or branched saturated alkyl groups substituted with cycloalkyl groups. C3~C n Cycloalkyl-C1~C n An example of an alkyl group is cyclopropylmethyl.

[0024] As used herein, the term "C3-C6 cycloalkyl" refers to a 3- to 6-membered cycloalkyl group such as cyclopropane, cyclobutane, cyclopropane, cyclopentane, and cyclohexane.

[0025] As used herein, "C3-C" is monosubstituted with cyanoside. n The term "cycloalkyl" refers to saturated or partially unsaturated monocyclic, bicyclic, or tricyclic hydrocarbons (as described above) having 3 to n carbon atoms substituted by a cyano group.

[0026] Halogens generally refer to fluorine, chlorine, bromine, or iodine. This also applies to halogens combined with other meanings, such as haloalkyls.

[0027] In relation to the present invention, the term "monosubstituted or polysubstituted" in the definition of the Q1 substituent typically means monosubstituted to 5-substituted, more preferably monosubstituted, disubstituted, or trisubstituted, depending on the chemical structure of the substituent.

[0028] In connection with the present invention, the phrases "Q1 is a 5-6 member aromatic or aromatic heterocyclic system linked via a ring carbon atom,..." and "Q1 is a 5 member aromatic heterocyclic system linked via a ring nitrogen atom,..." may refer to a specific embodiment of the bonding method of substituent Q1 to a group Q represented by either formula Qa or formula Qb (where Q is also substituted by the above-mentioned X-R1 and R3), which can be pyridyl or phenyl, respectively, when A represents N or CH.

[0029] In connection with the present invention, examples of "Q1 is a 5-6 member aromatic or aromatic heterocyclic system bonded via a ring carbon atom... and the ring system may contain 1, 2, or 3 heteroatoms..." are, but are not limited to, phenyl, pyrazolyl, triazolyl, pyridinyl, and pyrimidinyl; preferably phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidine-2-yl, pyrimidine-4-yl, and pyrimidine-5-yl.

[0030] In relation to the present invention, examples of "Q1 is a five-membered aromatic heterocyclic system bonded via a cyclic nitrogen atom... and the cyclic system contains one, two, or three heteroatoms..." are, but are not limited to, pyrazolyl, pyrrolyl, imidazolyl, and triazolyl; preferably pyrrole-1-yl, pyrazole-1-yl, triazole-2-yl, 1,2,4-triazole-1-yl, triazole-1-yl, and imidazole-1-yl.

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

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

[0033] Embodiment 2 provides a compound according to Embodiment 1, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein Q is Qa and has preferred values ​​for R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 as described below.

[0034] Embodiment 3 provides a compound according to Embodiment 1, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, wherein Q is Qb and has preferred values ​​for R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 as described below.

[0035] With respect to Embodiments 1 to 3, the preferred values ​​of R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 in any combination thereof are as follows. Preferably, R2 is a phenyl substituted with 1 to 3 substituents independently selected from the group consisting of halogens, cyanos, C1 to C4 alkyls, C1 to C4 haloalkyls, C1 to C4 alkoxys, C1 to C4 haloalkoxys, C1 to C4 alkylsulfanyls, C1 to C4 alkylsulfinyls, and C1 to C4 alkylsulfonyls; More preferably, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms.

[0036] More preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl.

[0037] Most preferably, R2 is -CF3, fluoro, chloro, bromo, iodine, or 4-fluorophenyl.

[0038] Preferably, G is CH or N.

[0039] Most preferably, G is CH.

[0040] Preferably, X1 is O, S, or N (C1-C2 alkyl).

[0041] More preferably, X1 is O, S, or NCH3.

[0042] Most preferably, X1 is O.

[0043] Preferably, R6 is a C1-C2 alkyl group.

[0044] More preferably, R6 is methyl or ethyl.

[0045] Most preferably, R6 is methyl.

[0046] Preferably, A is N or CH.

[0047] Most preferably, A is N.

[0048] Preferably, X is S or SO2.

[0049] Most preferably, X is SO2.

[0050] Preferably, R1 is a C1-C4 alkyl or cyclopropyl-C1-C4 alkyl.

[0051] More preferably, R1 is ethyl or cyclopropylmethyl.

[0052] Most preferably, R1 is ethyl.

[0053] When Q is Qa, preferably Q1 is hydrogen, a C1-C6 haloalkyl, a C3-C6 cycloalkyl, a C3-C6 cycloalkyl that is single-substituted with cyano, a C1-C6 cyanoalkyl, a C1-C6 cyanoalkoxy, a C1-C6 haloalkoxy, -N(R4)COR5, or 2-pyridyloxy.

[0054] It is also preferable that Q1 is a 5-6 member aromatic or aromatic heterocyclic system bonded to a ring containing substituent A via a ring carbon atom, wherein the ring system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos and C1-C4 haloalkyls; and the ring system may contain one or two ring nitrogen atoms.

[0055] It is also preferable that Q1 is a five-membered aromatic heterocyclic system bonded to a ring containing substituent A via a cyclic nitrogen atom, wherein the cyclic system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system contains two or three cyclic nitrogen atoms.

[0056] More preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is any of methyl, ethyl, or cyclopropyl; or Q1 is an N-linked pyrazolyl that can be monosubstituted with 2-pyridyloxy, chloro, cyano, or trifluoromethyl; or Q1 is an N-linked triazolyl or a C-linked pyrimidinyl.

[0057] Most preferably, Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0058] When Q is Qb, preferably Q1 is hydrogen, C3-C6 cycloalkyl, -N(R4)2, or -N(R4)COR5.

[0059] It is also preferable that Q1 is a 5-6 member aromatic or aromatic heterocyclic system bonded to a ring containing substituent A via a ring carbon atom, wherein the ring system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos and C1-C4 haloalkyls; and the ring system may contain one or two ring nitrogen atoms.

[0060] It is also preferable that Q1 is a five-membered aromatic heterocyclic system bonded to a ring containing substituent A via a cyclic nitrogen atom, wherein the cyclic system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system contains two or three cyclic nitrogen atoms.

[0061] More preferably, Q1 is hydrogen, cyclopropyl, -N(R4)2, or -N(R4)COR5, where in each of these, R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl, or cyclopropyl; or Q1 is N-linked triazolyl or C-linked pyrimidinyl.

[0062] Most preferably, Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0063] Preferably, R3 is hydrogen or a C1-C4 alkyl group.

[0064] More preferably, R3 is hydrogen or methyl.

[0065] Most preferably, R3 is hydrogen.

[0066] Preferably, each R4 is independently hydrogen or a C1-C4 alkyl group.

[0067] Most preferably, each R4 is independently hydrogen or methyl.

[0068] Preferably, R5 is a C1-C6 alkyl or C3-C6 cycloalkyl group.

[0069] More preferably, R5 is methyl, ethyl, or cyclopropyl.

[0070] Most preferably, R5 is methyl.

[0071] Further embodiments of the present invention are provided as described below.

[0072] The preferred group of compounds of formula I is formula I-1 [ka] (In the formula, R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 are as defined under Formula I above.) It is represented by a compound of formula I-1 or by an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide.

[0073] In one preferred group of compounds of formula I-1, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with 1-2 halogen atoms. G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl which is single-substituted with cyano, C1-C6 cyanoalkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, 2-pyridyloxy or -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is methyl, ethyl or cyclopropyl; and R3 is either hydrogen or methyl.

[0074] In other preferred groups of compounds of formula I-1, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy or -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is any of methyl, ethyl or cyclopropyl; and R3 is either hydrogen or methyl.

[0075] In other preferred groups of compounds of formula I-1, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; preferably, R2 is -CF3, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl) or 2-pyridyloxy; and R3 is either hydrogen or methyl.

[0076] In other preferred groups of compounds of formula I-1, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; preferably, R2 is -CF3, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is CH; X1 is O; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl) or 2-pyridyloxy; and R3 is hydrogen.

[0077] In other, more preferred groups of compounds of formula I-1, Q1 is a 5-6 member aromatic or aromatic heterocyclic system bonded via a ring carbon atom to a ring containing substituent A, wherein the cyclic system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system may contain one or two ring nitrogen atoms. In this embodiment, Q1 is more preferably a C-bonded pyrimidinyl.

[0078] A preferred compound of formula I-1 is a five-membered aromatic heterocyclic system in which Q1 is bonded to a ring containing substituent A via a ring nitrogen atom, wherein the cyclic system is unsubstituted or monosubstituted with substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system also contains two or three ring nitrogen atoms. In this embodiment, more preferably, Q1 is an N-linked pyrazolyl that can be monosubstituted with chloro, cyano, or trifluoromethyl, or Q1 is an N-linked triazolyl.

[0079] In other preferred groups of compounds of formula I-1, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; preferably, R2 is -CF3, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is an N-linked triazolyl, C-linked pyrimidinyl, or N-linked pyrazolyl, which can be monosubstituted with chloro, cyano, or trifluoromethyl; and R3 is either hydrogen or methyl.

[0080] In other preferred groups of compounds of formula I-1, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is CH; X1 is O; A is N; X is SO2; R1 is ethyl; Q1 is pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl or pyrimidine-2-yl; and R3 is hydrogen.

[0081] In all compounds of formula I-1 and preferred embodiments of the compounds of formula I-1 described above, unless otherwise specified, R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 are as defined in formula I above; Preferably, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, or halogen-substituted phenyl; most preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodo, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodo, or 4-fluorophenyl; Preferably, G is CH or N; most preferably, G is CH; Preferably, X1 is O, S, or NCH3; most preferably, X1 is O; Preferably, A is N or CH; most preferably, A is N; Preferably, X is S or SO2; most preferably, X is SO2; Preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, N-linked triazolyl, C-linked pyrimidinyl, or N-linked pyrazolyl which can be monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is any of methyl, ethyl, or cyclopropyl; more preferably, Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl Q1 is 1-cyanocyclopropyl, 1-cyano-1-methylethyl, 1-cyano-1-methylethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl; most preferably, Q1 is 1-cyanocyclopropyl or 1-cyano-1-methylethyl; Preferably, R3 is hydrogen or methyl; most preferably, R3 is hydrogen.

[0082] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-1), where, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, or N-linked pyrazolyl, which can be monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is N-linked triazolyl, C-linked pyrimidinyl, or -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is any of methyl, ethyl, or cyclopropyl; and R3 is either hydrogen or methyl.

[0083] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-2), which is a compound of formula (I-1-1), where, Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0084] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-3), which is a compound of formula (I-1-1), where, Q1 is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, or cyanoisopropoxy.

[0085] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-4), which is a compound of formula (I-1-1), where, Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, or 1-cyano-1-methyl-ethoxy.

[0086] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-5), where, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodo, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodo, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl or 1-cyano-1-methyl-ethoxy; and R3 is hydrogen.

[0087] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-6), which is a compound of formula (I-1-5), where, G is CH; and X1 is O.

[0088] A more preferred group of compounds according to this embodiment is a compound of formula (I-1-7), which is a compound of formula (I-1-5), where, G is N; and X1 is O.

[0089] Other preferred groups of compounds of formula I include those of formula I-2. [ka] (In the formula, R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 are as defined under Formula I above.) It is represented by a compound of formula I-2 or by an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide.

[0090] In one preferred group of compounds of formula I-2, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, C3-C6 cycloalkyl, -N(R4)2 or -N(R4)COR5, where in each of these, R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; and R3 is either hydrogen or methyl.

[0091] In other preferred groups of compounds of formula I-2, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, -N(R4)2 or -N(R4)COR5, where in each of these, R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; and R3 is either hydrogen or methyl.

[0092] In other preferred groups of compounds of formula I-2, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); and R3 is either hydrogen or methyl.

[0093] In other preferred groups of compounds of formula I-2, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is CH; X1 is O; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl); and R3 is hydrogen.

[0094] In other, more preferred groups of compounds of formula I-2, Q1 is a 5-6 member aromatic or aromatic heterocyclic system bonded via a ring carbon atom to a ring containing substituent A, wherein the cyclic system is unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system may contain one or two ring nitrogen atoms. In this embodiment, Q1 is more preferably a C-bonded pyrimidinyl.

[0095] A preferred compound of formula I-2 is a five-membered aromatic heterocyclic system in which Q1 is bonded to a ring containing substituent A via a ring nitrogen atom, wherein the cyclic system is either unsubstituted or monosubstituted by substituents selected from the group consisting of halogens, cyanos, and C1-C4 haloalkyls; and the cyclic system also contains two or three ring nitrogen atoms. In this embodiment, Q1 is more preferably an N-bonded triazolyl.

[0096] In other preferred groups of compounds of formula I-2, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is an N-linked triazolyl or a C-linked pyrimidinyl; and R3 is either hydrogen or methyl.

[0097] In other preferred groups of compounds of formula I-2, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodine, or 4-fluorophenyl; G is CH; X1 is O; A is N; X is SO2; R1 is ethyl; Q1 is 1,2,4-triazole-1-yl or pyrimidine-2-yl; and R3 is hydrogen.

[0098] In all compounds of formula I-2 and preferred embodiments of the compounds of formula I-2 described above, unless otherwise specified, R2, G, X1, R6, A, X, R1, Q1, R3, R4, and R5 are as defined in formula I described above; Preferably, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, or phenyl, and is a phenyl substituted with one or two halogen atoms; most preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodo, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodo, or 4-fluorophenyl; Preferably, G is CH or N; most preferably, G is CH; Preferably, X1 is O, S, or NCH3; most preferably, X1 is O; Preferably, A is N or CH; most preferably, A is N; Preferably, X is S or SO2; most preferably, X is SO2; Preferably, R1 is ethyl or cyclopropylmethyl; most preferably, R1 is ethyl; Preferably, Q1 is hydrogen, cyclopropyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2 or -N(R4)COR5, where in each of these, R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; most preferably, Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3 or -N(CH3)CO(cyclopropyl), 1,2,4-triazole-1-yl or pyrimidine-2-yl; Preferably, R3 is hydrogen or methyl; most preferably, R3 is hydrogen.

[0099] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-1), where, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; G is either CH or N; X1 is O, S, or NCH3; A is either N or CH; X is either S or SO2; R1 is ethyl or cyclopropylmethyl; Q1 is hydrogen, cyclopropyl, N-linked triazolyl, C-linked pyrimidinyl, -N(R4)2 or -N(R4)COR5, where in each of these, R4 is independently either hydrogen or methyl, and R5 is either methyl, ethyl or cyclopropyl; and R3 is either hydrogen or methyl.

[0100] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-2), which is a compound of formula (I-2-1), where, Q1 is hydrogen, cyclopropyl, -NH(CH3), -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), or 1,2,4-triazole-1-yl or pyrimidine-2-yl.

[0101] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-3), which is a compound of formula (I-2-1), where, Q1 is hydrogen, cyclopropyl, N-linked triazolyl, or C-linked pyrimidinyl.

[0102] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-4), which is a compound of formula (I-2-1), where, Q1 is hydrogen, cyclopropyl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0103] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-5), where, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodo, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodo, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; A is N; X is SO2; R1 is ethyl; Q1 is hydrogen, cyclopropyl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl; and R3 is hydrogen.

[0104] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-6), which is a compound of formula (I-2-5), where, G is CH; X1 is O.

[0105] A more preferred group of compounds according to this embodiment is a compound of formula (I-2-7), which is a compound of formula (I-2-5), where, G is N; and X1 is O.

[0106] The excellent group of compounds according to the present invention is formula I-3 [ka] (In the formula, R2 is a C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, halogen, cyano, or phenyl, and is a phenyl substituted with one or two halogen atoms; preferably, R2 is -CF3, -CF2CF3, -CHF2, -OCF3, -OCHF2, cyano, fluoro, chloro, bromo, iodo, 3,5-difluorophenyl, or 4-fluorophenyl; more preferably, R2 is -CF3, -OCF3, -OCHF2, fluoro, chloro, bromo, iodo, or 4-fluorophenyl; G is either CH or N; X1 is O, S, or NCH3; Q' is derived from equations Qa1 and Qb1. [ka] A group selected from the group consisting of, In the equation, the arrows indicate the bonding points to the biring ring; Q1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, or N-linked pyrazolyl, which can be monosubstituted with chloro, cyano, or trifluoromethyl; or Q1 is N-linked triazolyl, C-linked pyrimidinyl, or -N(R4)COR5, where R4 is hydrogen or methyl, and R5 is methyl, ethyl, or cyclopropyl. The compounds are those described above, or agriculturally chemistry-acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides of the compounds of formula I-3.

[0107] A further excellent group of compounds according to this embodiment is a compound of formula (I-3), which is a compound of formula (I-3-1), where, Q1 is hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH3)COCH3, -N(CH3)COCH2CH3, -N(CH3)CO(cyclopropyl), 2-pyridyloxy, pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0108] A further excellent group of compounds according to this embodiment is a compound of formula (I-3), which is a compound of formula (I-3-2), where, Q1 is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, N-linked triazolyl, or C-linked pyrimidinyl.

[0109] A further excellent group of compounds according to this embodiment is the compound of formula (I-3), which is the compound of formula (I-3-3), where, Q1 is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

[0110] A further excellent group of compounds according to this embodiment is the compound of formula (I-3-3), the compound of formula (I-3-4), in which, G is CH; and X1 is O.

[0111] A further excellent group of compounds according to this embodiment is the compound of formula (I-3-3), the compound of formula (I-3-5), in which, G is N; and X1 is O.

[0112] The compounds according to the present invention may have any number of advantages, including, in particular, advantageous levels of biological activity for protecting plants from insects or excellent properties for use as agricultural chemical active ingredients (e.g., high biological activity, advantageous activity range, high safety profile, improved physicochemical properties, or high biodegradability or environmental profile). In particular, it has been unexpectedly found that certain compounds of formula (I) may exhibit an advantageous safety profile, especially for non-target arthropods such as honeybees, solitary honeybees, and bumblebees. Most specifically, the European honeybee (Apis mellifera).

[0113] In other embodiments, the present invention provides a composition comprising an insecticidal, acaricidal, nematodetic, or molluscicidal amount of a compound of formula (I) as defined in embodiments of the compounds of formulas (I-1), (I-2), and (I-3) (above), or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, and optionally an auxiliary agent or diluent.

[0114] In a further embodiment, the present invention provides a method for controlling and eliminating insects, mites, nematodes, or mollusks, comprising applying an insecticidal, acaricidal, nematodetic, or molluscicidal amount of a compound of formula (I) as defined in any embodiment of the compounds of formulas (I-1), (I-2), and (I-3) (above), or an agriculturally acceptable salt thereof, stereoisomer, enantiomer, tautomer, or N-oxide, or a composition defined above, to a pest, a pest habitat, or a plant susceptible to attack by a pest.

[0115] In a further embodiment, the present invention provides a method for protecting plant propagation material from attack by insects, mites, nematodes, or mollusks, comprising treating the propagation material or the place where the propagation material is planted with the composition defined above.

[0116] The preparation process for the compounds of formula I according to the present invention is basically carried out by methods known to those skilled in the art. More specifically, as described in schemes 1 and 2, the subgroup of compounds of formula I (wherein X is SO (sulfoxide) and / or SO2 (sulfone)) can be obtained by the corresponding oxidation reaction of the sulfide compounds of formula I where X is S, involving reagents such as metachloroperbenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite, or tert-butyl hypochlorite, among other oxidizing agents. The oxidation reaction is generally carried out in the presence of a solvent. Examples of solvents used in this reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of oxidizing agent used in this reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, based on 1 mole of sulfide compound I to produce sulfoxide compound I, and preferably 2 to 2.2 moles of oxidizing agent based on 1 mole of sulfide compound I to produce sulfone compound I. Such oxidation reactions are disclosed, for example, in International Publication No. 2013 / 018928. Scheme 1 (All substituents are as defined in Formula I) [ka]

[0117] The chemistry described above in Scheme 1 for obtaining compounds of formula I-a2 and I-a3 from compound of formula I-a1 can be similarly applied to the preparation of compounds of formula I-a5 and I-a6 from compound of formula I-a4 (Scheme 2), and all previously stated substituent definitions remain valid. Scheme 2 [ka]

[0118] A subgroup of compounds of formula I (wherein R2, G, and X1 are as defined in formula I, and Q is defined as Qa, and Q1, R3, X, A, and R1 are as defined in formula I) can be defined as compounds of formula I-Qa.

[0119] Scheme 3 [ka] Such compounds of formula I-Qa include, for example, compounds of formula II-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, iodine, or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) and compounds of formula III (wherein R2, G, and X1 are as defined in formula I, and Ya is, for example, B(OH)2 or B(OR b1 )2(wherein, R b1 This can be a C1-C4 alkyl group, or two groups OR b1The reaction can be prepared by a Suzuki cross-coupling reaction, which involves reacting a boron-derived functional group (such as pinacol boronic acid ester, which can combine with a boron atom to form a five-membered ring, for example) (Scheme 3). This reaction can be catalyzed by a palladium-based catalyst, such as tetrakis(triphenylphosphine)-palladium or (1,1'bis(diphenylphosphin)-ferrocene)dichloropalladium-dichloromethane (1:1 complex), in a solvent or solvent mixture, such as a mixture of 1,2-dimethoxyethane and water, or a mixture of dioxane and water, or a mixture of acetonitrile and water, preferably in an inert atmosphere, in the presence of a base such as sodium carbonate, potassium carbonate, or cesium fluoride. The reaction temperature can preferably be in the range of ambient temperature to the boiling point of the reaction mixture. Such Suzuki reactions are well known to those skilled in the art and have been reviewed, for example, in J. Orgmet. Chem. 576, 1999, 147-168.

[0120] Alternatively, compounds of formula I-Qa can be prepared by a Still-cross coupling reaction between a compound of formula III (wherein Ya is a trialkyltin derivative, preferably tri-n-butyltin) and a compound of formula II-Qa (wherein Xa is a leaving group such as chlorine, bromine, or iodine, or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid). Such Still reactions are usually carried out in an inert solvent such as DMF, acetonitrile, or dioxane, in the presence of a palladium catalyst such as tetrakis(triphenylphosphine)palladium(O) or (1,1'bis(diphenylphosphino)-ferrocene)dichloropalladium-dichloromethane (1:1 complex), optionally in the presence of additives such as cesium fluoride or lithium chloride, and optionally in the presence of a further catalyst such as copper(I) iodide. Such still 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.

[0121] Compound of formula III (wherein R2, G and X1 are as defined in formula I, and Ya is, for example, B(OH)2 or B(OR) b1 )2(wherein, R b1 This can be a C1-C4 alkyl group, or two groups OR b1 (These are boron-derived functional groups that can combine with a boron atom to form a five-membered ring, such as pinacol boronic acid ester.) Scheme 4 [ka] This can be prepared by reacting the compound of formula IV (wherein R2, G, and X1 are as defined in formula I, and Xb is a leaving group such as chlorine, bromine, or iodine) under the boration conditions detailed in Scheme 5 (Scheme 4).

[0122] Alternatively, the compound of formula III (wherein R2, G, and X1 are as defined in formula I, and Ya is a trialkyltin derivative, preferably tri-n-butyltin) may be prepared by a stanylation step, which includes reacting the compound of formula IV with an organometallic species such as an organomagnesium compound (e.g., isopropylmagnesium chloride) to produce an intermediate species by metal-halogen exchange carried out at a low temperature, preferably -78°C to 0°C, preferably in an anhydrous aprotic solvent such as tetrahydrofuran, and quenching the intermediate species with a tin reagent of formula (alkyl)3SnCl, for example tri-n-butyltin chloride (n-butyl)3SnCl.

[0123] Similarly, compounds of formula IIIa (subgroup of compounds of formula III) (wherein R2, G and X1 are as defined in formula I, and Ya is B(OR) b1 )2(wherein, R b1 (It is a C1-C4 alkyl group.) Scheme 5 [ka] This involves reacting a compound of formula IV (wherein R2, G, and X1 are as defined in formula I, and Xb is a leaving group such as chlorine, bromine, or iodine) with an organometallic species such as an organomagnesium compound (e.g., isopropylmagnesium chloride or isopropylmagnesium chloride lithium chloride complex) to produce an intermediate species by metal-halogen exchange carried out at a low temperature, preferably -78°C to 0°C, in an anhydrous aprotic solvent such as tetrahydrofuran, and then converting the intermediate species to formula B (OR b1 )3 trialkylborate reagent (wherein R b1 It can be prepared by reacting it with a C1-C4 alkyl group (Scheme 5). Depending on the properties of the trialkyl borate, the reaction conditions and workup conditions, dialkylboronate IIIa can be formed and isolated, or the boronic acid compound of formula IIIc (another subgroup of compounds of formula III) (wherein R2, G and X1 are as defined in formula I) can be obtained directly. Such conditions are described in the literature, e.g., International Publication 2017 / 122722.

[0124] Compounds of formula IIIb (another subgroup of compounds of formula III) (wherein R2, G and X1 are as defined in formula I, and Ya is pinacol boronic acid (also known as the Bpin group, with two OR groups) b1The compound of formula IV (wherein R2, G, and X1 are as defined in formula I, and Xb is a leaving group such as chlorine, bromine, or iodine) can be prepared by reacting it with bis(pinacolato)diborane of formula V under palladium-catalyzed conditions. Typically, such conditions include 1,1'bis(diphenylphosphino)ferrocene)dichloropalladium(II) (optionally as a dichloromethane adduct) in an inert solvent, such as dioxane, N,N-dimethylformamide, or acetonitrile, in the presence of a base, such as potassium acetate or potassium carbonate, preferably in an inert atmosphere, at a temperature preferably in the range from ambient temperature to the boiling point of the reaction mixture. Such conditions are described in the literature, e.g., Bioorg. Med. Chem. 15, 7138-7143 (2007). Depending on the reaction and post-treatment conditions, pinacol ester IIIb boronic acid can be formed in situ, and the boronic acid compound of formula IIIc can be obtained directly. Such conditions are described in the literature, for example, Chem. Pharm. Bull. 68(8):797-801 (2020).

[0125] Hydrolysis of a compound of formula IIIa or IIIb to a compound of formula IIIc (all substituents as defined above) can be carried out by methods known to those skilled in the art, for example, using water, optionally in the presence of a cosolvent such as pentane, tetrahydrofuran or methanol, and optionally in the presence of an aqueous acid (such as hydrochloric acid) or an aqueous base (such as lithium hydroxide, sodium hydroxide or potassium hydroxide), preferably at a temperature of 0 to 40°C, more preferably about 10 to 30°C.

[0126] Compounds of formula II-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, or iodine). Scheme 6 [ka] This can be prepared by reacting a compound of formula VI-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I) with a nitrite such as tert-butyl t-BuONO nitrite or isoamyl nitrite (example under non-aqueous conditions) or sodium nitrite, in the presence of a hydrohalogen HXa and a copper salt Cu(I)Xa (wherein Xa is a leaving group such as chlorine, bromine, or iodine) in water (aqueous conditions) under Sandmeyer-type conditions (Scheme 6). This conversion is preferably carried out in an inert solvent, such as acetonitrile or a halogenating solvent such as 1,2-dichloroethane or 1,2-dibromoloethane (under non-aqueous conditions) or in water, at a temperature of 0 to 150°C, preferably in the range from room temperature to the boiling point of the reaction mixture.

[0127] Instead, a compound of formula II-Qa (wherein X is S, Q1, R3, A and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine or iodine or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) is a compound of formula VII-Qa (wherein Q1, R3 and A are as defined in formula I, and Xa is a leaving group such as chlorine, bromine or iodine or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid, and Xc is a leaving group such as fluoro or nitro) is a compound of formula VIII R1-SH(VIII) (In the formula, R1 is as defined in formula I.) It can be prepared by reacting the reagent or a salt thereof with an optionally suitable base, such as alkali metal carbonates, such as sodium carbonate and potassium carbonate, or alkali metal hydrides, such as sodium hydride, or alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide, or sodium or potassium tert-butoxide, in an inert solvent, preferably at a temperature of 25 to 120°C. Examples of solvents 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, and dimethyl sulfoxide. An example of a salt of the compound of formula VIII is formula VIIIa R1-SM(VIIIa) (In the formula, R1 is as defined above, and M is, for example, sodium or potassium.) Examples of compounds of formula VIII include the following. A process for preparing such compounds of formula VIII can be found, for example, in International Publication No. 16 / 091731.

[0128] Alternatively, this reaction to form II-Qa can be carried out at a temperature of 100-160°C, preferably 140°C, in the presence of a palladium catalyst such as tris(dibenzylideneacetone)dipalladium(0), a phosphine ligand such as xanthophos, and an inert solvent such as xylene, as described in Tetrahedron 2005, 61, 5253-5259.

[0129] The oxidation of a compound of formula II-Qa (wherein X is SO or SO2) with a suitable oxidizing agent (wherein X is S, Q1, R3, A and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine or iodine or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) can be achieved under the conditions described above.

[0130] Certain compounds of formula II-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine) are publicly known and described in International Publication No. 2019 / 131587. Other compounds of formula II-Qa can be prepared in a manner similar to the preparation instructions found in the aforementioned literature.

[0131] Certain compounds of formula VI-Qa (wherein Q1, R3, X, A, and R1 are as defined in formula I) are publicly known and described in International Publication No. 2020 / 174094. Other compounds of formula VI-Qa may be prepared in a manner similar to the preparation instructions found in the aforementioned document, or by methods known to those skilled in the art.

[0132] Compounds of formula VII-Qa (wherein Q1, R3, and A are as defined in formula I, Xa is a leaving group such as chlorine, bromine, or iodine, or an aryl- or alkyl sulfonate such as trifluoromethanesulfonate, and Xc is a leaving group such as fluoro or nitro); and reagents or salts thereof of formulas VIII and VIIIa (wherein R1 is as defined in formula I) are known, commercially available, or can be prepared by methods known to those skilled in the art.

[0133] Compounds of formula IV (wherein R2, G, and X1 are as defined in formula I, and Xb is a leaving group such as chlorine, bromine, or iodine). Scheme 7 [ka] The compound of formula IX (wherein R2, G, and X1 are as defined in formula I) is subjected to electrophilic halogen source Xb in an inert solvent such as dichloromethane, chloroform, acetonitrile, dimethylacetamide, methanol, ethanol, or pyridine at a temperature of 0 to 50°C. +It can be prepared by reacting it with a reagent (e.g., bromine Br2, N-bromosuccinimide NBS, iodine I2, or t-butyl hypochlorite tBuOCl) (where Xb is chlorine, bromine, or iodine) (Scheme 7).

[0134] The compound of formula IX (wherein R2, G, and X1 are as defined in formula I) can be prepared by reacting the compound of formula X (wherein R2, G, and X1 are as defined in formula I) with the reagent of formula XI under heating conditions, optionally in the presence of a diluent such as N,N-dimethylformamide, dimethylacetamide, toluene, or xylene, at a temperature of 50 to 180°C, preferably in the range of 80°C to the boiling point of the reaction mixture. Typically, the reagent of formula XI is, for example, N,N-dimethyl-formamide dimethylacetal DMF-DMA, which is commercially available or can be prepared according to known procedures. These conditions (for both steps of Scheme 7) are described in the literature, e.g., Synthesis 901-903 (1979), Bioorg. Med. Chem. Lett. 25, 2510-2513 (2015), or Eur. J. Org. Chem. 6440-6446 (2020).

[0135] Instead, a compound of formula IV (wherein R2, G, and X1 are as defined in formula I, and Xb is a leaving group such as chlorine, bromine, or iodine). Scheme 8 [ka] The compound of formula XII (wherein R2, G, and X1 are as defined in formula I) can be prepared by carrying out a halogenation reaction (Scheme 8). Preferred conditions may include reacting the compound of formula XII with pyrrolidine or piperidine in an alcohol (such as methanol or ethanol) at a temperature of 30°C to 100°C, preferably in the range of 60°C to the boiling point of the reaction mixture, to form an enaminoketone intermediate. The enaminoketone intermediate can then be treated with a halogenating reagent of formula (Xb)2 (wherein Xb is chlorine, bromine, or iodine) in an inert solvent (e.g., chloroform) at a temperature of 0 to 40°C to obtain the compound of formula IV. Alternatively, the oxidative halogenation conditions may also be suitable for forming the compound of formula IV by reacting the compound of formula XII with a hydrohalic acid HXb (wherein Xb is chlorine, bromine, or iodine) in the presence of an oxidizing agent such as oxone (Synthesis (2004), 2641-2644, preferably Xb is chlorine or bromine) or m-chloroperbenzoic acid (Synthesis (1993), 283-4; preferably Xb is chlorine) in an inert solvent (e.g., dichloromethane or N,N-dimethylformamide, etc.) at a temperature of 0 to 40°C. Other oxidative halogenation conditions may include cerium ammonium nitrate (CAN) and iodine (where Xb is iodine) at a temperature of 50–90°C in an inert solvent (e.g., acetonitrile), as described in Tetrahedron Letters 72(2021) article 153070 (https: / / doi.org / 10.1016 / j.tetlet.2021.153070).

[0136] Compound XII (wherein R2, G, and X1 are as defined in Formula I) can be prepared by cyclizing compound XIII (wherein R2, G, and X1 are as defined in Formula I, and Ra is hydrogen or a C1-C4 alkyl group) in an inert solvent such as acetic acid, methanol, ethanol, dimethyl sulfoxide, or water (or a mixture thereof) in the presence of an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, p-toluenesulfonic acid, or polyphosphate, at a temperature of 0 to 100°C, preferably from room temperature to 80°C. Such conditions are described in the literature, e.g., J.Med.Chem.33,1859-1865(1990). In certain situations where Ra is a C1-C4 alkyl group, cyclization can be achieved by using optionally catalytic amounts of potassium carbonate in an inert solvent such as N,N-dimethylformamide or dimethylacetamide at a temperature of 80-180°C, as described in Organic Letters 14, 2710-2713 (2012).

[0137] Compounds of formula XIII (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group) Scheme 9 [ka] These can typically be prepared by Claisen condensation chemistry from starting materials of either formula X-1 or XIV under conditions known to those skilled in the art (Scheme 9). For example, the compound of formula XIII can be prepared by combining the compound of formula X-1 (wherein R2, G and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group) with HC(O)OR b The reagent (in the formula, R bThe compounds are obtained by condensation with a C1-C4 alkyl group (preferably methyl or ethyl) in an inert solvent such as tetrahydrofuran, diethyl ether, or t-butyl ethyl ether, in the presence of a base such as sodium hydride, sodium methoxide, sodium ethoxide, or potassium t-butoxide. The compounds of formula X (Scheme 7) described above form a specific subgroup of the compounds of formula X-1 (wherein Ra is hydrogen).

[0138] Instead, the compound of formula XIII is the compound of formula XIV (wherein R2, G and X1 are as defined in formula I, Ra is hydrogen or C1-C4 alkyl, R c (The reagent is chloro or C1-C4 alkoxy (preferably methoxy or ethoxy)) and HC(O)CH3 or HC(O)CH2C(O)R d The reagent (in the formula, R d It is obtained by condensation with methyl or C1-C4 alkoxy (preferably methoxy or ethoxy). Such conditions are described in the literature, e.g., J.Med.Chem.33,1859-1865(1990).

[0139] Compounds of formula X-1 (wherein R2, G and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) (including compounds of formula X, wherein R2, G and X1 are as defined in formula I); and compounds of formula XIV (wherein R2, G and X1 are as defined in formula I, Ra is hydrogen or C1-C4 alkyl, R c The compound (which is chloro or C1-C4 alkoxy (preferably methoxy or ethoxy)) is known, commercially available, or can be prepared by methods known to those skilled in the art.

[0140] A subgroup of compounds of formula I (wherein R2, G, and X1 are as defined in formula I above, Q is defined as Qb, and Q1, R3, X, A, and R1 are as defined in formula I) can be defined as compounds of formula I-Qb. Scheme 10 [ka] The chemical reactions described in Scheme 3 for obtaining the compound of formula I-Qa from the compound of formula III and the compound of formula II-Qa can be similarly applied to preparing the compound of formula I-Qb from the compound of formula III and the compound of formula II-Qb (Scheme 10), and all previously described definitions of substituents remain valid.

[0141] The chemical reaction described in Scheme 6 for obtaining the compound of formula II-Qa from either the compound of formula VI-Qa or the compound of formula VII-Qa can similarly be applied to prepare the compound of formula II-Qb from either the compound of formula VI-Qb or the compound of formula VII-Qb (Scheme 11), and all previously described definitions of substituents remain valid. Scheme 11 [ka]

[0142] Alternatively, compounds of formula I-Qb (wherein Q1, R3, X, A, R1, R2, G, and X1 are as defined in formula I) can be prepared as shown in scheme 12. Scheme 12 [ka]

[0143] In certain situations within Scheme 12, if Q1 is an optionally substituted triazole bonded to a ring containing group A via a ring nitrogen atom, then the compound of formula I-Qb (wherein X is SO or SO2) is optionally sterilized in a solvent such as an alcohol (e.g., methanol, ethanol, isopropanol, or high-boiling 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, e.g., copper(I) iodide, at a temperature of 30-180°C. A compound of formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) can be prepared by reaction (CN bond formation) with optionally substituted triazole Q1-H (containing a suitable NH functional group) (XVIaa) (wherein Q1 is an N-triazolyl) under Chlorophyll irradiation.

[0144] In certain situations within Scheme 12, when Q1 is -N(R4)COR5 (wherein R4 and R5 are as defined in Formula I), the compound of Formula I-Qb (wherein X is SO or SO2) can be prepared by reacting the compound of Formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in Formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) with reagent Q1-H(XVIaa) which corresponds to HN(R4)COR5 (wherein R4 and R5 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, or tetrahydrofuran THF, with the optional catalyst being, for example, palladium(II) acetate, bis(dibenzylideneacetone)palladium(O)(Pd(dba)2) or tris(dibenzylideneacetone)-dipalladium(O)(Pd2(dba)3, optionally in the form of a chloroform adduct), or, for example, 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 The procedure is carried out at a temperature of 60-120°C, optionally under microwave irradiation, in the presence of a palladium precatalyst such as G3[(2-di-cyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate and optionally in the presence of a ligand, such as SPhos, t-BuBrettPhos, or xanthophos.

[0145] In certain situations within Scheme 12, when Q1 is -N(R4)2 (wherein R4 is as defined in Formula I), the compound of Formula I-Qb (wherein X is SO or SO2) can be prepared by reaction (CN bond formation) from the compound of Formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in Formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl- or alkyl sulfonate such as trifluoromethanesulfonate) to the reagent Q1-H(XVIaa) or a salt thereof (such as a hydrohalide, preferably hydrochloride or hydrobromide, or trifluoroacetate or any other corresponding salt) (wherein R4 is as defined in Formula I). Such reactions are typically carried out in an inert solvent such as alcohols, amides, esters, ethers, nitriles, and water (particularly preferred are 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 a temperature of 0 to 150°C, optionally under pressurized conditions using microwave irradiation or autoclaving, optionally in the presence of a copper catalyst, such as copper powder, copper(I) iodide, or copper sulfate (optionally in hydrate form), or mixtures thereof, optionally in the presence of a ligand, such as a diamine ligand (e.g., 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.

[0146] 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.

[0147] Instead, a compound of formula I-Qb (wherein X is SO or SO2) is, for example, a compound of formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl sulfonate or alkyl sulfonate such as trifluoromethanesulfonate) is a compound of formula (XVI) (wherein Q1 is as defined in formula I, Y b1 For example, B(OH)2 or B(OR b1 )2 and other boron-derived functional groups, R b1 This can be a C1-C4 alkyl group, or two groups OR b1 This can be prepared by a Suzuki reaction, which involves reacting it with a boron atom (which can form a five-membered ring, such as pinacol boronic acid ester). This reaction can be catalyzed, preferably in an inert atmosphere, in the presence of a base such as sodium carbonate, tripotassium phosphate, or cesium fluoride, and 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. 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 have been reviewed, for example, in J. Organomet. Chem. 576, 1999, 147-168.

[0148] Instead, the compounds of formula I-Qb (wherein X is SO or SO2) are compounds of formula (XVIa) (wherein Q1 is as defined above, and Yb2 The compounds can be prepared by a Still reaction between a trialkyltin derivative (preferably tri-n-butyltin or tri-methyltin) and a compound of formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl sulfonate or alkyl sulfonate such as trifluoromethanesulfonate). Such Still reactions are usually carried out in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)palladium(O) or bis(triphenylphosphine)palladium(II) dichloride, in an inert solvent such as N,N-dimethylformamide, acetonitrile, toluene or dioxane, optionally in the presence of additives such as cesium fluoride or lithium chloride, and optionally in the presence of further catalysts such as copper(I) iodide. Such still 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.

[0149] If Q1 is a five-membered aromatic ring system bonded to a ring containing substituent A via a ring nitrogen atom, then the compound of formula I-Qb (wherein X is SO or SO2) can be prepared in the presence of a base such as potassium carbonate K2CO3 or cesium carbonate Cs2CO3, optionally in the presence of a copper catalyst such as copper(I) iodide, with or without additives such as 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). In particular, at a temperature of 30 to 150°C, a compound of formula XVb (wherein R3, X, A, R1, R2, G and X1 are as defined in formula I above, X is SO or SO2, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) can be prepared by reaction with a heterocyclic Q1-H (containing a suitable NH functional group) (XVIaa) (wherein Q1 is as defined above) at an optional microwave irradiation temperature.

[0150] The oxidation of a compound of formula XVb (wherein X is SO or SO2) with a suitable oxidizing agent (wherein R3, X, A, R1, R2, G and X1 are as defined in formula I above, X is S, and Xd is a leaving group such as chlorine, bromine or iodine (preferably chlorine or bromine) or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) can be achieved under the conditions described above.

[0151] Numerous compounds of formulas (XVI), (XVIa), and (XVIaa) are commercially available or can be prepared by those skilled in the art.

[0152] Alternatively, compounds of formula I-Qb (wherein X is SO or SO2) can be prepared from compounds of formula XVb (wherein X is S (sulfide)) by altering the order of steps, but with the same chemical reactions as described above (i.e., performing the sequence from XVb (where X is S) to I-Qb (where X is S) via Suzuki, Still, or CN bond formation, followed by an oxidation step to form I-Qb (where X is SO or SO2)).

[0153] The chemistry described in Scheme 12 for obtaining compounds of formula I-Qb from compounds of formula XVb can similarly be applied to the preparation of compounds of formula I-Qa from compounds of formula XVa (Scheme 13), and all the previously described substituent definitions remain valid. Scheme 13 [ka]

[0154] Instead, a compound of formula I (wherein Q, R2, G, and X1 are as defined in formula I) Scheme 14 [ka] The compound of formula XVIII (wherein Q (in this scheme 14, the arrow in Qa, and each Qb, indicate a bond site to the ortho carbon atom relative to the carbonyl group), R2, G, and X1 are as defined in formula I) can be prepared by reacting it with the reagent of formula XI under similar conditions to those described in scheme 7 for converting the compound of formula X to the compound of formula IX (Scheme 14). Typically, the reagent of formula XI is, for example, N,N-dimethylformamide dimethylacetal DMF-DMA. Process XVIII+XI under such conditions allows for the direct formation of the compound of formula I without isolating the possible intermediate compound of formula XVII (wherein Q, R2, G, and X1 are as defined in formula I). ​​Such cyclization conditions are described in the literature, e.g., International Publication 2015 / 047113.

[0155] Similarly, the compound of formula I (wherein Q, R2, G and X1 are as defined in formula I) is used to obtain the compound of formula XVIII (wherein Q, R2, G and X1 are as defined in formula I), and the reagent of formula XIX (wherein R f The reagent can be prepared by reacting a C1-C4 alkyl group with an additive (optionally catalytically) preferably pyridine, piperidine, morpholine, or 4-dimethylaminopyridine (DMAP), and optionally a diluent such as N,N-dimethylformamide, dimethylacetamide, toluene, or xylene, at a temperature of 50-180°C, preferably in the range of 80°C to the boiling point of the reaction mixture (Scheme 14). Typically, the reagent of formula XIX is, for example, triethyl orthoformate (R f ( is ethyl). Process XVIII+XIX under these conditions yields a possible intermediate compound of formula XX (wherein Q, R2, G and X1 are as defined in formula I, and R f This allows for the direct formation of compounds of formula I without isolating the C1-C4 alkyl group. Such cyclization conditions are described in the literature, e.g., J. Chem Research (12), 683-685 (2008).

[0156] Instead, a compound of formula I (wherein Q, R2, G, and X1 are as defined in formula I) Scheme 15 [ka] This can be prepared by cyclizing the compound of formula XXI (wherein Q (in this scheme 15, the arrow in Qa, and each Qb indicates a bond point to the ortho carbon atom relative to the carbonyl group), R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl) under similar conditions to those previously described in scheme 8 for the conversion of the compound of formula XIII to the compound of formula XII) (Scheme 15). Other such cyclization conditions are also described in the literature, e.g., International Publication No. 2007 / 065888 or Eur.J.Org.Chem.2971-2983(2019).

[0157] Compounds of formula XVIII (wherein Q (in scheme 18, the arrow in Qa and each Qb indicate the bond site to the ortho carbon atom relative to the carbonyl group), R2, G, and X1 are as defined in formula I) Scheme 16 [ka] This can be prepared by dealkylating the compound of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra is a C1-C4 alkyl) in a solvent such as dichloromethane or 1,2-dichloroethane in the presence of a reagent such as boron tribromide or aluminum chloride at a temperature in the range of -78°C to room temperature under conditions known to those skilled in the art and described, for example, in J Med Chem 61,7917-7928 (2018) (Scheme 16).

[0158] Compounds of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) (including compounds of formula XVIII, wherein Q, R2, G, and X1 are as defined in formula I) are compounds of formula X-1 (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or C1-C4 alkyl) (including compounds of formula X, wherein R2, G, and X1 are as defined in formula I) are compounds of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is For example, it can be prepared by reacting any of the leaving groups (such as chlorine, bromine, iodine, or aryl- or alkyl sulfonates such as trifluoromethanesulfonic acid) with a base, such as potassium carbonate or cesium carbonate, sodium hydride, sodium methoxide, sodium ethoxide, or potassium t-butoxide, in an inert solvent, such as tetrahydrofuran, t-butyl ethyl ether, acetonitrile, dimethyl sulfoxide, or N,N-dimethylformamide, at a temperature of 0 to 80°C, preferably from 20°C to the boiling point of the reaction mixture. Such conditions are described in the literature, for example, Tetrahedron Letters 54, 402-405 (2013). By reacting X-1 with II-Qa, XVIII-1 is obtained where Q is Qa; similarly, by reacting X-1 with II-Qb, XVIII-1 is obtained where Q is Qb.

[0159] Instead, the compound of formula XVIII-1 (wherein Q, R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group) is combined with the compound of formula X-1 (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group) and either the compound of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, iodine, or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) and a catalyst, such as palladium acetate ( II) can be prepared by reacting in the presence of palladium(II) chloride, bis(dibenzylideneacetone)palladium(O)(Pd(dba)2) or tris(dibenzylideneacetone)-dipalladium(O)(Pd2(dba)3, optionally in the form of a chloroform adduct), in the presence of a ligand, e.g., triphenylphosphine, BINAP or xanthophos, in the presence of a base, e.g., sodium or potassium t-butoxide, cesium carbonate or potassium carbonate, in an inert solvent, e.g., tetrahydrofuran, toluene or dioxane, and optionally under microwave irradiation at a temperature of 60–120°C. Such conditions are described in the literature, e.g., International Publication No. 2016 / 097073, Chinese Patent No. 109956928, or Angew Chem Int Ed 53, 1529–1533 (2014).

[0160] Compounds of formula XXI (wherein Q (in this scheme 17, the arrow in Qa and each Qb indicate a bond point to the ortho carbon atom relative to the carbonyl group), R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group). Scheme 17 [ka] This can be prepared by reacting a compound of formula XIII (wherein R2, G, and X1 are as defined in formula I, and Ra is hydrogen or a C1-C4 alkyl group) with either a compound of formula II-Qa or II-Qb (wherein Q1, R3, X, A, and R1 are as defined in formula I, and Xa is a leaving group such as chlorine, bromine, iodine, or an aryl- or alkyl sulfonate such as trifluoromethanesulfonic acid) in the presence of a base, such as lithium diisopropylamide, potassium bis(trimethylsilyl)amide, sodium methoxide, sodium ethoxide, potassium t-butoxide, or sodium hydride, optionally under a copper or palladium catalyst, in an inert solvent, such as tetrahydrofuran, t-butyl ethyl ether, or N,N-dimethylformamide, at a temperature of 0-80°C (Scheme 17). By reacting XIII with II-Qa, XXI is obtained where Q is Qa; similarly, by reacting XIII with II-Qb, XXI is obtained where Q is Qb.

[0161] These reagents can be reacted in the presence of a base. Suitable bases include 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 hydroxides, and carbocyclic amines. Examples that may be listed 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]undeca-7-ene (DBU).

[0162] These reagents can react with each other as they are, i.e., without the addition of a solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent, or a mixture thereof. If the reaction is carried out in the presence of a base, the base, used in excess, such as triethylamine, pyridine, N-methylmorpholine, or N,N-diethylaniline, can also act as a solvent or diluent.

[0163] This reaction is favorably carried out in a temperature range of approximately -80°C to approximately +140°C, preferably approximately -30°C to approximately +100°C, and often within the range of ambient temperature to approximately +80°C.

[0164] In the conventional method, by substituting one or more substituents of the starting compound of formula I with other substituents according to the present invention, and by post-modification of the compound by reactions such as oxidation, alkylation, reduction, acylation, and other methods known to those skilled in the art, the compound of formula I can be converted into other compounds of formula I by methods known per se.

[0165] Depending on the selection of suitable reaction conditions and starting materials in each case, for example, in one reaction step, it may only be possible to replace one substituent with another substituent according to the present invention, or in the same reaction step, multiple substituents can be replaced with other substituents according to the present invention.

[0166] The salts of the compounds of formula I can be prepared in a manner known per se. Thus, for example, the acid addition salts of the compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchange reagent, and the salts with bases are obtained by treatment with a suitable base or a suitable ion exchange reagent.

[0167] The salts of the compounds of formula I can be converted into the free compound I (acid addition salt) in a conventional manner, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, and can be converted into salts with bases, for example, by treatment with a suitable acid or a suitable ion exchange reagent.

[0168] The salts of the compounds of formula I can be converted into other salts (acid addition salts, for example, other acid addition salts) of the compounds of formula I in a manner known per se, for example, in a suitable solvent (for example, an inorganic salt that forms silver chloride is insoluble and thus precipitates from the reaction mixture), by treating the salt of an inorganic acid such as hydrochloric acid with a suitable metal salt of an acid (for example, silver acetate) such as sodium, barium or silver salt.

[0169] Depending on the method or reaction conditions, the compounds of formula I having salt-forming properties can be obtained in free form or in salt form.

[0170] The compounds of formula I and, where appropriate, their tautomers, may exist in free or salt form, in one form of a possible isomer or as a mixture thereof, depending on the number, absolute and relative configuration of chiral carbon atoms present in the molecule and / or the configuration of non-aromatic double bonds present in the molecule, in the form of pure isomers such as enantiomers and / or diastereomers, or as a mixture of enantiomers such as racemic compounds, diastereomer mixtures, or racemic compound mixtures, and the present invention relates to pure isomers and to all possible mixtures of isomers, and should be understood in this sense above and below, respectively, even if stereochemical details are not specifically described for each.

[0171] A diastereomer or racemic mixture of compounds of formula I can be separated into pure diastereomers or racemic compounds based on physicochemical differences of the components, for example by fractional crystallization, distillation and / or chromatography, in the free or salt forms obtained depending on the selected starting materials and procedure.

[0172] Enantiomer mixtures such as racemates, which can be obtained by a similar method, can be separated into optically active enantiomers by known methods, such as recrystallization from an optically active solvent, chromatography on a chiral adsorbent, such as high-performance liquid chromatography (HPLC) on acetylcellulose, cleavage with specific immobilized enzymes using appropriate microorganisms, formation of inclusion compounds, for example, using a chiral crown ether that complexes with only one enantiomer, or conversion to a diastereomer salt. For example, a racemate, which is a basic final product, can be reacted with an optically active acid, such as a carboxylic acid, such as camphor, tartaric acid, or malic acid, or a sulfonic acid, such as camphorsulfonic acid. The diastereomer mixture thus obtained can then be separated to obtain diastereomers, for example, by fractional crystallization based on their different solubility (from which the desired enantiomer can be liberated by the action of an appropriate reagent, such as a basic reagent).

[0173] Pure diastereomers or enantioisomers can be obtained not only by separating a suitable mixture of isomers according to the present invention, but also by diastereoselective or enantioselective synthesis, which is a generally known method, for example, by carrying out the process according to the present invention using starting materials having suitable stereochemistry.

[0174] N-oxides can be prepared by reacting the compound of formula I with a suitable oxidizing agent, such as H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidation is known from the literature, e.g., J.Med.Chem., 32(12), 2561-73, 1989 or International Publication No. 2000 / 15615.

[0175] When individual components have different biological activities, it is advantageous to isolate or synthesize biologically more effective isomers, such as enantiomers or diastereomers, or mixtures of isomers, such as mixtures of enantiomers or diastereomers.

[0176] The compounds of formula I and, optionally, their tautomers may also be obtained in free form or salt form, and optionally in hydrate form, and / or in other solvents, such as solvents that have been used to crystallize compounds existing in solid form.

[0177] The compounds in Tables A-1 to A-48, B-1 to B-48, C-1 to C-48, and D-1 to D-48 below can be prepared according to the methods described above. The following examples are intended to illustrate the present invention and to show preferred compounds of formula I.

[0178] Tables A-1 to A-48 below illustrate specific compounds of the present invention. [ka]

[0179] Table A-1 provides 20 compounds A-1.001 to A-1.020 of formula Ia-Qa, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0180] [Table 1]

[0181] In Table Y and Table A, "cycloC3" represents cyclopropyl.

[0182] For example, compound A-10.018 is as follows. [Chemical Structure]

[0183] Table A-2 provides 20 compounds A-2.001 to A-2.020 of formula Ia-Qa, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0184] Table A-3 provides 20 compounds A-3.001 to A-3.020 of formula Ia-Qa, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0185] Table A-4 provides 20 compounds A-4.001 to A-4.020 of formula Ia-Qa, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0186] Table A-5 provides 20 compounds A-5.001 to A-5.020 of formula Ia-Qa, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0187] Table A-6 provides 20 compounds A-6.001 to A-6.020 of formulas Ia-Qa, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0188] Table A-7 provides 20 compounds of formulas Ia-Qa, A-7.001 to A-7.020, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0189] Table A-8 provides 20 compounds of formulas Ia-Qa, A-8.001 to A-8.019, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0190] Table A-9 provides 20 compounds of formulas Ia-Qa, A-9.001 to A-9.020, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0191] Table A-10 provides 20 compounds of formulas Ia-Qa, A-10.001 to A-10.020, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0192] Table A-11 provides 20 compounds of formulas Ia-Qa, A-11.001 to A-11.020, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0193] Table A-12 provides 20 compounds of formulas Ia-Qa, A-12.001 to A-12.020, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0194] Table A-13 provides 20 compounds A-13.001 to A-13.020 of formulas Ia-Qa, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0195] Table A-14 provides 20 compounds of formulas Ia-Qa, A-14.001 to A-14.020, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0196] Table A-15 provides 20 compounds of formulas Ia-Qa, A-15.001 to A-15.020, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0197] Table A-16 provides 20 compounds of formulas Ia-Qa, A-16.001 to A-16.020, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0198] Table A-17 provides 20 compounds of formulas Ia-Qa, A-17.001 to A-17.020, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0199] Table A-18 provides 20 compounds of formulas Ia-Qa, A-18.001 to A-18.020, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0200] Table A-19 provides 20 compounds A-19.001 to A-19.020 of formulas Ia-Qa, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0201] Table A-20 provides 20 compounds of formulas Ia-Qa, A-20.001 to A-20.020, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0202] Table A-21 provides 20 compounds of formulas Ia-Qa, A-21.001 to A-21.020, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0203] Table A-22 provides 20 compounds of formulas Ia-Qa, A-22.001 to A-22.020, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0204] Table A-23 provides 20 compounds of formulas Ia-Qa, A-23.001 to A-23.020, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0205] Table A-24 provides 20 compounds of formulas Ia-Qa, A-24.001 to A-24.020, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0206] Table A-25 provides 20 compounds of formulas Ia-Qa, A-25.001 to A-25.020, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0207] Table A-26 provides 20 compounds of formulas Ia-Qa, A-26.001 to A-26.020, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0208] Table A-27 provides 20 compounds of formulas Ia-Qa, A-27.001 to A-27.020, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0209] Table A-28 provides 20 compounds of formulas Ia-Qa, A-28.001 to A-28.020, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0210] Table A-29 provides 20 compounds of formulas Ia-Qa, A-29.001 to A-29.020, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0211] Table A-30 provides 20 compounds of formulas Ia-Qa, A-30.001 to A-30.020, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0212] Table A-31 provides 20 compounds of formulas Ia-Qa, A-31.001 to A-31.020, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0213] Table A-32 provides 20 compounds of formulas Ia-Qa, A-32.001 to A-32.020, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0214] Table A-33 provides 20 compounds of formulas Ia-Qa, A-33.001 to A-33.020, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0215] Table A-34 provides 20 compounds of formulas Ia-Qa, A-34.001 to A-34.020, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0216] Table A-35 provides 20 compounds of formulas Ia-Qa, A-35.001 to A-35.020, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0217] Table A-36 provides 20 compounds of formulas Ia-Qa, A-36.001 to A-36.020, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0218] Table A-37 provides 20 compounds of formulas Ia-Qa, A-37.001 to A-37.020, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0219] Table A-38 provides 20 compounds of formulas Ia-Qa, A-38.001 to A-38.020, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0220] Table A-39 provides 20 compounds of formulas Ia-Qa, A-39.001 to A-39.020, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0221] Table A-40 provides 20 compounds of formulas Ia-Qa, A-40.001 to A-40.020, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0222] Table A-41 provides 20 compounds of formulas Ia-Qa, A-41.001 to A-41.020, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0223] Table A-42 provides 20 compounds of formulas Ia-Qa, A-42.001 to A-42.020, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0224] Table A-43 provides 20 compounds of formulas Ia-Qa, A-43.001 to A-43.020, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0225] Table A-44 provides 20 compounds of formulas Ia-Qa, A-44.001 to A-44.020, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0226] Table A-45 provides 20 compounds of formulas Ia-Qa, A-45.001 to A-45.020, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0227] Table A-46 provides 20 compounds of formulas Ia-Qa, A-46.001 to A-46.020, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0228] Table A-47 provides 20 compounds of formulas Ia-Qa, A-47.001 to A-47.020, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0229] Table A-48 provides 20 compounds of formulas Ia-Qa, A-48.001 to A-48.020, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0230] Tables B-1 to B-48 below further illustrate specific compounds of the present invention. [ka]

[0231] Table B-1 provides 12 compounds B-1.001 to B-1.012 of formulas Ia-Qb, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0232] [Table 2]

[0233] In Tables Z and B, "cycloC3" represents cyclopropyl.

[0234] Table B-2 provides 12 compounds B-2.001 to B-2.012 of formulas Ia-Qb, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0235] Table B-3 provides 12 compounds B-3.001 to B-3.012 of formula Ia-Qb, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0236] Table B-4 provides 12 compounds B-4.001 to B-4.012 of formulas Ia-Qb, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0237] Table B-5 provides 12 compounds B-5.001 to B-5.012 of formulas Ia-Qb, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0238] Table B-6 provides 12 compounds B-6.001 to B-6.012 of formulas Ia-Qb, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0239] Table B-7 provides 12 compounds B-7.001 to B-7.012 of formulas Ia-Qb, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0240] Table B-8 provides 12 compounds B-8.001 to B-8.012 of formulas Ia-Qb, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0241] Table B-9 provides 12 compounds B-9.001 to B-9.012 of formulas Ia-Qb, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0242] Table B-10 provides 12 compounds B-10.001 to B-10.012 of formulas Ia-Qb, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0243] Table B-11 provides 12 compounds B-11.001 to B-11.012 of formulas Ia-Qb, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0244] Table B-12 provides 12 compounds B-12.001 to B-12.012 of formulas Ia-Qb, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0245] Table B-13 provides 12 compounds of formulas Ia-Qb, 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.

[0246] Table B-14 provides 12 compounds of formulas Ia-Qb, 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.

[0247] Table B-15 provides 12 compounds B-15.001 to B-15.012 of formula Ia-Qb, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0248] Table B-16 provides 12 compounds B-16.001 to B-16.012 of formulas Ia-Qb, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0249] Table B-17 provides 12 compounds B-17.001 to B-17.012 of formulas Ia-Qb, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0250] Table B-18 provides 12 compounds of formulas Ia-Qb, 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.

[0251] Table B-19 provides 12 compounds of formulas Ia-Qb, 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.

[0252] Table B-20 provides 12 compounds of formulas Ia-Qb, 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.

[0253] Table B-21 provides 12 compounds B-21.001 to B-21.012 of formula Ia-Qb, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0254] Table B-22 provides 12 compounds B-22.001 to B-22.012 of formulas Ia-Qb, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0255] Table B-23 provides 12 compounds B-23.001 to B-23.012 of formulas Ia-Qb, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0256] Table B-24 provides 12 compounds of formulas Ia-Qb, 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.

[0257] Table B-25 provides 12 compounds of formulas Ia-Qb, 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.

[0258] Table B-26 provides 12 compounds of formulas Ia-Qb, 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.

[0259] Table B-27 provides 12 compounds of formulas Ia-Qb, 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.

[0260] Table B-28 provides 12 compounds of formulas Ia-Qb, 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.

[0261] Table B-29 provides 12 compounds of formulas Ia-Qb, B-29.001 to B-29.012, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0262] Table B-30 provides 12 compounds B-30.001 to B-30.012 of formula Ia-Qb, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0263] Table B-31 provides 12 compounds of formulas Ia-Qb, 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.

[0264] Table B-32 provides 12 compounds B-32.001 to B-32.012 of formulas Ia-Qb, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0265] Table B-33 provides 12 compounds of formulas Ia-Qb, 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.

[0266] Table B-34 provides 12 compounds of formulas Ia-Qb, 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.

[0267] Table B-34 provides 12 compounds of formulas Ia-Qb, B-35.001 to B-35.012, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0268] Table B-36 provides 12 compounds of formulas Ia-Qb, 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.

[0269] Table B-37 provides 12 compounds of formulas Ia-Qb, B-37.001 to B-37.012, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0270] Table B-38 provides 12 compounds of formulas Ia-Qb, B-38.001 to B-38.012, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0271] Table B-39 provides 12 compounds of formulas Ia-Qb, B-39.001 to B-39.012, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0272] Table B-40 provides 12 compounds B-40.001 to B-40.012 of formula Ia-Qb, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0273] Table B-41 provides 12 compounds B-41.001 to B-41.012 of formula Ia-Qb, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0274] Table B-42 provides 12 compounds B-42.001 to B-42.012 of formulas Ia-Qb, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0275] Table B-43 provides 12 compounds of formulas Ia-Qb, B-43.001 to B-43.012, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0276] Table B-44 provides 12 compounds of formulas Ia-Qb, B-44.001 to B-44.012, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0277] Table B-45 provides 12 compounds of formulas Ia-Qb, B-45.001 to B-45.012, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0278] Table B-46 provides 12 compounds of formulas Ia-Qb, B-46.001 to B-46.012, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0279] Table B-47 provides 12 compounds of formulas Ia-Qb, B-47.001 to B-47.012, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0280] Table B-48 provides 12 compounds of formulas Ia-Qb, B-48.001 to B-48.012, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0281] Tables C-1 to C-48 below further illustrate specific compounds of the present invention. [ka]

[0282] In Tables Y and C, "cycloC3" represents cyclopropyl.

[0283] Table C-1 provides 20 compounds of formula Ib-Qa, C-1.001 to C-1.020, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0284] Table C-2 provides 20 compounds of formula Ib-Qa, C-2.001 to C-2.020, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0285] Table C-3 provides 20 compounds of formula Ib-Qa, C-3.001 to C-3.020, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0286] Table C-4 provides 20 compounds of formula Ib-Qa, C-4.001 to C-4.020, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0287] Table C-5 provides 20 compounds of formula Ib-Qa, C-5.001 to C-5.020, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0288] Table C-6 provides 20 compounds of formula Ib-Qa, C-6.001 to C-6.020, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0289] Table C-7 provides 20 compounds of formula Ib-Qa, C-7.001 to C-7.020, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0290] Table C-8 provides 20 compounds of formula Ib-Qa, C-8.001 to C-8.020, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0291] Table C-9 provides 20 compounds of formula Ib-Qa, C-9.001 to C-9.020, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0292] Table C-10 provides 20 compounds of formula Ib-Qa, C-10.001 to C-10.020, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0293] Table C-11 provides 20 compounds of formula Ib-Qa, C-11.001 to C-11.020, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0294] Table C-12 provides 20 compounds of formula Ib-Qa, C-12.001 to C-12.020, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0295] Table C-13 provides 20 compounds of formula Ib-Qa, C-13.001 to C-13.020, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0296] Table C-14 provides 20 compounds of formula Ib-Qa, C-14.001 to C-14.020, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0297] Table C-15 provides 20 compounds of formula Ib-Qa, C-15.001 to C-15.020, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0298] Table C-16 provides 20 compounds of formula Ib-Qa, C-16.001 to C-16.020, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0299] Table C-17 provides 20 compounds of formula Ib-Qa, C-17.001 to C-17.020, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0300] Table C-18 provides 20 compounds of formula Ib-Qa, C-18.001 to C-18.020, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0301] Table C-19 provides 20 compounds of formula Ib-Qa, C-19.001 to C-19.020, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0302] Table C-20 provides 20 compounds of formula Ib-Qa, C-20.001 to C-20.020, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0303] Table C-21 provides 20 compounds of formula Ib-Qa, C-21.001 to C-21.020, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0304] Table C-22 provides 20 compounds of formula Ib-Qa, C-22.001 to C-22.020, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0305] Table C-23 provides 20 compounds of formula Ib-Qa, C-23.001 to C-23.020, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0306] Table C-24 provides 20 compounds of formula Ib-Qa, C-24.001 to C-24.020, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0307] Table C-25 provides 20 compounds of formula Ib-Qa, C-25.001 to C-25.020, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0308] Table C-26 provides 20 compounds of formula Ib-Qa, C-26.001 to C-26.020, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0309] Table C-27 provides 20 compounds of formula Ib-Qa, C-27.001 to C-27.020, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0310] Table C-28 provides 20 compounds of formula Ib-Qa, C-28.001 to C-28.020, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0311] Table C-29 provides 20 compounds of formula Ib-Qa, C-29.001 to C-29.020, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0312] Table C-30 provides 20 compounds of formula Ib-Qa, C-30.001 to C-30.020, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0313] Table C-31 provides 20 compounds of formula Ib-Qa, C-31.001 to C-31.020, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0314] Table C-32 provides 20 compounds of formula Ib-Qa, C-32.001 to C-32.020, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0315] Table C-33 provides 20 compounds of formula Ib-Qa, C-33.001 to C-33.020, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0316] Table C-34 provides 20 compounds of formula Ib-Qa, C-34.001 to C-34.020, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0317] Table C-35 provides 20 compounds of formula Ib-Qa, C-35.001 to C-35.020, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0318] Table C-36 provides 20 compounds of formula Ib-Qa, C-36.001 to C-36.020, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0319] Table C-37 provides 20 compounds of formula Ib-Qa, C-37.001 to C-37.020, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0320] Table C-38 provides 20 compounds of formula Ib-Qa, C-38.001 to C-38.020, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0321] Table C-39 provides 20 compounds of formula Ib-Qa, C-39.001 to C-39.020, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0322] Table C-40 provides 20 compounds of formula Ib-Qa, C-40.001 to C-40.020, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0323] Table C-41 provides 20 compounds of formula Ib-Qa, C-41.001 to C-41.020, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0324] Table C-42 provides 20 compounds of formula Ib-Qa, C-42.001 to C-42.020, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0325] Table C-43 provides 20 compounds of formula Ib-Qa, C-43.001 to C-43.020, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0326] Table C-44 provides 20 compounds of formula Ib-Qa, C-44.001 to C-44.020, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0327] Table C-45 provides 20 compounds of formula Ib-Qa, C-45.001 to C-45.020, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0328] Table C-46 provides 20 compounds of formula Ib-Qa, C-46.001 to C-46.020, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0329] Table C-47 provides 20 compounds of formula Ib-Qa, C-47.001 to C-47.020, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0330] Table C-48 provides 20 compounds of formula Ib-Qa, C-48.001 to C-48.020, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Y.

[0331] Tables D-1 to D-48 below further illustrate specific compounds of the present invention. [ka]

[0332] In Tables Z and D, "cycloC3" represents cyclopropyl.

[0333] Table D-1 provides 12 compounds D-1.001 to D-1.012 of formula Ib-Qb, where R2 is CF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0334] Table D-2 provides 12 compounds D-2.001 to D-2.012 of formula Ib-Qb, where R2 is CF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0335] Table D-3 provides 12 compounds D-3.001 to D-3.012 of formula Ib-Qb, where R2 is CF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0336] Table D-4 provides 12 compounds D-4.001 to D-4.012 of formula Ib-Qb, where R2 is CF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0337] Table D-5 provides 12 compounds D-5.001 to D-5.012 of formula Ib-Qb, where R2 is CF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0338] Table D-6 provides 12 compounds D-6.001 to D-6.012 of formula Ib-Qb, where R2 is CF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0339] Table D-7 provides 12 compounds D-7.001 to D-7.012 of formula Ib-Qb, where R2 is OCHF2, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0340] Table D-8 provides 12 compounds D-8.001 to D-8.012 of formula Ib-Qb, where R2 is OCHF2, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0341] Table D-9 provides 12 compounds D-9.001 to D-9.012 of formula Ib-Qb, where R2 is OCHF2, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0342] Table D-10 provides 12 compounds D-10.001 to D-10.012 of formula Ib-Qb, where R2 is OCHF2, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0343] Table D-11 provides 12 compounds D-11.001 to D-11.012 of formula Ib-Qb, where R2 is OCHF2, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0344] Table D-12 provides 12 compounds D-12.001 to D-12.012 of formula Ib-Qb, where R2 is OCHF2, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0345] Table D-13 provides 12 compounds of formula Ib-Qb, D-13.001 to D-13.012, where R2 is OCF3, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0346] Table D-14 provides 12 compounds of formula Ib-Qb, D-14.001 to D-14.012, where R2 is OCF3, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0347] Table D-15 provides 12 compounds of formula Ib-Qb, D-15.001 to D-15.012, where R2 is OCF3, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0348] Table D-16 provides 12 compounds D-16.001 to D-16.012 of formula Ib-Qb, where R2 is OCF3, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0349] Table D-17 provides 12 compounds D-17.001 to D-17.012 of formula Ib-Qb, where R2 is OCF3, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0350] Table D-18 provides 12 compounds D-18.001 to D-18.012 of formula Ib-Qb, where R2 is OCF3, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0351] Table D-19 provides 12 compounds of formula Ib-Qb, D-19.001 to D-19.012, where R2 is F, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0352] Table D-20 provides 12 compounds of formula Ib-Qb, D-20.001 to D-20.012, where R2 is F, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0353] Table D-21 provides 12 compounds D-21.001 to D-21.012 of formula Ib-Qb, where R2 is F, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0354] Table D-22 provides 12 compounds D-22.001 to D-22.012 of formula Ib-Qb, where R2 is F, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0355] Table D-23 provides 12 compounds of formula Ib-Qb, D-23.001 to D-23.012, where R2 is F, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0356] Table D-24 provides 12 compounds of formula Ib-Qb, D-24.001 to D-24.012, where R2 is F, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0357] Table D-25 provides 12 compounds of formula Ib-Qb, D-25.001 to D-25.012, where R2 is Cl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0358] Table D-26 provides 12 compounds of formula Ib-Qb, D-26.001 to D-26.012, where R2 is Cl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0359] Table D-27 provides 12 compounds of formula Ib-Qb, D-27.001 to D-27.012, where R2 is Cl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0360] Table D-28 provides 12 compounds of formula Ib-Qb, D-28.001 to D-28.012, where R2 is Cl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0361] Table D-29 provides 12 compounds of formula Ib-Qb, D-29.001 to D-29.012, where R2 is Cl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0362] Table D-30 provides 12 compounds D-30.001 to D-30.012 of formula Ib-Qb, where R2 is Cl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0363] Table D-31 provides 12 compounds of formula Ib-Qb, D-31.001 to D-31.012, where R2 is Br, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0364] Table D-32 provides 12 compounds of formula Ib-Qb, D-32.001 to D-32.012, where R2 is Br, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0365] Table D-33 provides 12 compounds of formula Ib-Qb, D-33.001 to D-33.012, where R2 is Br, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0366] Table D-34 provides 12 compounds of formula Ib-Qb, D-34.001 to D-34.012, where R2 is Br, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0367] Table D-35 provides 12 compounds of formula Ib-Qb, D-35.001 to D-35.012, where R2 is Br, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0368] Table D-36 provides 12 compounds of formula Ib-Qb, D-36.001 to D-36.012, where R2 is Br, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0369] Table D-37 provides 12 compounds of formula Ib-Qb, D-37.001 to D-37.012, where R2 is CN, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0370] Table D-38 provides 12 compounds of formula Ib-Qb, D-38.001 to D-38.012, where R2 is CN, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0371] Table D-39 provides 12 compounds of formula Ib-Qb, D-39.001 to D-39.012, where R2 is CN, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0372] Table D-40 provides 12 compounds D-40.001 to D-40.012 of formula Ib-Qb, where R2 is CN, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0373] Table D-41 provides 12 compounds of formula Ib-Qb, D-41.001 to D-41.012, where R2 is CN, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0374] Table D-42 provides 12 compounds D-42.001 to D-42.012 of formula Ib-Qb, where R2 is CN, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0375] Table D-43 provides 12 compounds of formula Ib-Qb, D-43.001 to D-43.012, where R2 is 4-F-phenyl, A is N, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0376] Table D-44 provides 12 compounds of formula Ib-Qb, D-44.001 to D-44.012, where R2 is 4-F-phenyl, A is N, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0377] Table D-45 provides 12 compounds of formula Ib-Qa, D-45.001 to D-45.012, where R2 is 4-F-phenyl, A is N, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0378] Table D-46 provides 12 compounds D-46.001 to D-46.012 of formula Ib-Qb, where R2 is 4-F-phenyl, A is CH, X is S, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0379] Table D-47 provides 12 compounds D-47.001 to D-47.012 of formula Ib-Qb, where R2 is 4-F-phenyl, A is CH, X is SO, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0380] Table D-48 provides 12 compounds of formula Ib-Qb, D-48.001 to D-48.012, where R2 is 4-F-phenyl, A is CH, X is SO2, R1 is CH2CH3, and Q1 is as defined in Table Z.

[0381] The compound of Formula I according to the present invention is an active ingredient that is beneficial preventively and / or therapeutically in the field of pest control even at low application rates, and it has a very favorable biocidal spectrum and exhibits good tolerance by warm-blooded animal species, fish, and plants. The active ingredient according to the present invention acts not only on commonly susceptible animal pests such as insects or representative examples of mites (Acarina), but also on all or individual developmental stages of resistant animal pests. The insecticidal or acaricidal activity of the active ingredient according to the present invention may manifest directly (i.e., killing of pests immediately or only after a certain period of time, such as during molting) or indirectly (e.g., reduction of oviposition and / or hatching rate, good activity corresponding to at least 50-60% euthanasia rate (mortality rate)).

[0382] Examples of the animal pests mentioned above are as follows: Acari (Acarina), for example, Acaritus 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.) 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.), genus Rhizoglyphus, genus Sarcoptes, genus Steneotarsonemus, genus Tarsonemus, and genus Tetranychus; Lice (Anoplura), for example, The genera Haematopinus, Linognathus, Pediculus, Pemphigus, and Phylloxera; Coleoptera, for example, Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Atenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Connoderus 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., Maledra castanea, Megascelis spp.) Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp., Popillia spp.), Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabaeidae family, Sitophilus spp., Sitotroga spp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp., and Trogoderma spp.; Diptera, for example, Genus Aedes, Anopheles, Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia, Calliphora erythrocephala, Ceratitis, Chrysomyia, Culex, Cuterebra, Dacus, Delia, Drosophila melanogaster, Fannia 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.), Rhagoletis spp., Riveria quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp., and Tipula spp.; Hemiptera, for example, Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp., Clavigralla tomentosicollis, Creontiades spp., Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp., Euschistus spp.), Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp., Margarodes spp., Murgantia histrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp.), Piezodorus spp., Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp., Thyanta spp., Triatoma spp.) and Vatiga illudens; Acyrthosium pisum, Adalges spp., Agalliana ensigera, Aganoscena targionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella (spp.), Aphididae family, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp.), Chrysomphalus aonidium, Greenhouse scale insect (Chrysomphalus dictyospermi), Cicadella spp., White leafhopper (Cofana spectra), Cryptomyzus spp., Cicadulina spp., Flat scale insect (Coccus hesperidum), Dalbulus maidis, Dialeurodes spp., Citrus psyllid (Diaphorina citri), Diuraphis noxia, Dysaphis spp., Empoasca spp., Apple woolly aphid (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 sp., Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp., Phorodon humuli), Phylloxera spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Cotton flea beetle (Pseudatomoscelis seriatus), Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Lightning leafhopper (Recilia dorsalis), Rhopalosiphum spp., Saissetia spp., Scaphoideus (spp.), Schizaphis spp., Sitobion spp.), Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris; Hymenoptera, for example, The genera Acromyrmex, Arge, Atta, Cephus, Diprion, Diprionidae, Gilpinia polytoma, Hoplocampa, Lasius, Monomorium pharaonis, Neodiprion, Pogonomyrmex, Slenopsis invicta, Solenopsis, and Vespa; The order Isoptera, for example, Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis gemminate; Lepidoptera, for example, 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 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 lycopersella Lycopersicella, Sorghum 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), corn borer (Ostrinia nubilalis), Pammene spp., Pandemis spp.), pine moth (Panolis flammea), Papaipema nebris, cotton beetle (Pectinophora gossypiela), coffee leafminer (Perileucoptera coffeella), Pseudaletia unipuncta, potato 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.), genera Sparganothis, Spodoptera, Sylepta derogate, Synanthedon, Thaumetopoea, Tortrix, Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.); The order Mallophaga, for example, The genera Damalinea and Trichodectes; Orthoptera, for example, The genera Blatta, Blattella, Grillosa, Leucophaea maderae, Locusta, Neocurtilla hexadactyla, Periplaneta, Scapteriscus, and Schistocerca; Psocoptera, for example, Liposcelis genus (Liposcelis spp.) Chirps (Siphonaptera), for example, The genera Ceratophyllus, Ctenocephalides, and Xenopsylla cheopis; Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinotothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp. Silverfish (Thysanura), for example, the European silverfish (Lepisma saccharina).

[0383] The active ingredients of the present invention can be used to control, contain, or destroy, the above-mentioned types of pests that occur particularly on plants, particularly on useful and ornamental plants in agriculture, horticulture and forestry, or on organs of such plants, such as fruits, flowers, leaves, stalks, tubers or roots, and in some cases on plant organs that are formed at a later time and remain protected from these pests.

[0384] Suitable target crops include, in particular, cereals such as wheat, barley, rye, oats, rice, maize, or sorghum; beets such as sugar or fodder beets; fruits such as pome, stone fruit, or soft fruits such as apples, pears, plums, peaches, almonds, cherries, or berries such as strawberries, raspberries, or blackberries; legumes such as kidney beans, lentils, peas, or soybeans; oil crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor beans, cocoa, or ground nuts; and cucurbits. Plants, such as pumpkins, cucumbers, or melons; fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as oranges, lemons, grapefruit, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or peppers; the Lauraceae family, such as avocado, cinnamon, or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, the Plantaginaceae family, and latex plants.

[0385] The compositions and / or methods of the present invention may also be used with any ornamental and / or vegetable crops, including flowers, shrubs, broad-leaved trees and evergreen trees.

[0386] For example, the present invention can be used for 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 (Ornamental), Calceolaria 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, Dorotheanthus (spp.), Eustoma 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. (African balsam (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. (carnation), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (ivy geranium (P. peltatum), honeysuckle (P. Zonale)), Viola spp. (pansy), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp., Parthenocissus spp. (American ivy (P. quinquefolia), ivy (P. tricuspidata)), Primula spp. Ranunculus spp., Rhododendron spp., Rosa spp., 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.

[0387] For example, the present invention can be used for 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. (wild cabbage (B. Oleracea), Chinese cabbage (B. Pekinensis), turnip (B. rapa)), chili pepper (Capsicum annuum), chickpea (Cicer arietinum), endive (Cichorium endivia), Cichorum genus (spp.) (Chicory (C. intybus), Endive (C. endivia)), Watermelon (Citrillus lanatus), Cucumis spp. (Saffron (C. sativus), Melon (C. melo)), Cucurbita spp. (Pumpkin (C. pepo), European pumpkin (C. 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)), Mentha spp., Basil (Ocimum basilicum), Parsley (Petroselinum crispum), Phaseolus spp. (Pinguicula vulgaris, Red bean (P.Coccineus, pea (Pisum sativum), radish (Raphanus sativus), round-leaved rhubarb (Rheum rhaponticum), rosemarinus spp., salvia spp., yellow rose lily (Scorzonera hispanica), eggplant (Solanum melongena), spinach (Spinacea oleracea), Valerianella spp. (Valerianella locusta, Valerianella eriocarpa), and broad bean (Vicia faba).

[0388] Preferred ornamental plant species include African violet, begonia, dahlia, gerbera, hydrangea, verbena, rose, kalanchoe, poinsettia, aster, cornflower, coreopsis, delphinium, monarda, and phlox. Examples include Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, Rosemary, Sage, St. John's wort, Mint, Bell pepper, Tomato, and Cucumber.

[0389] The active ingredient according to the present invention is particularly suitable for controlling bean aphids (Aphis craccivora), Diabrotica balteata, Heliothis virescens, Myzus persicae, diamondback moth (Plutella xylostella), and Egyptian armyworm (Spodoptera littoralis) in cotton, vegetables, corn, rice, and soybean crops. The active ingredient according to the present invention is particularly suitable for controlling armyworms (Mamestra) (preferably in vegetables), codling moths (Cydia pomonella) (preferably in apples), Empoasca species (preferably in vegetables and vineyards), Leptinotarsa ​​species (preferably in potatoes), and rice stem borer (Chilo supressalis) (preferably in rice).

[0390] The active ingredient according to the present invention is particularly suitable for controlling bean aphids (Aphis craccivora), Diabrotica balteata, Heliothis virescens, Myzus persicae, diamondback moth (Plutella xylostella), and Egyptian armyworm (Spodoptera littoralis) in cotton, vegetables, corn, rice, and soybean crops. The active ingredient according to the present invention is particularly suitable for controlling armyworms (Mamestra) (preferably in vegetables), codling moths (Cydia pomonella) (preferably in apples), Empoasca species (preferably in vegetables and vineyards), Leptinotarsa ​​species (preferably in potatoes), and rice stem borer (Chilo supressalis) (preferably in rice).

[0391] In a further embodiment, the present invention relates to plant parasitic nematodes (endoparasitic, semi-endoparasitic, and ectoparasitic nematodes), particularly root-knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria, and other Meloidogyne species: cyst-forming nematodes, potato cyst nematodes (Globodera rostochiensis), and other Globodera species; Heterodera avenae, soybean cyst nematodes (Heterodera glycines), and sugar beet cyst nematodes (Heterodera schachtii), black cyst nematode (Heterodera trifolii) and other Heterodera species; seed nematodes, Anguina species; stem and leaf nematodes, Aphelenchoides species; bristly nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, pine wood nematode (Bursaphelenchus xylophilus) and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor 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 and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; root-knot nematodes, Nacobbus species; needle-shaped nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; lesion nematodes, Pratylenchus neglecttus * 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's root nematode*, *Trichodorus primitives* *Trichodorus primitivus* and other *Trichodorus* species, *Paratrichodorus* species; *Stunt* nematodes, *Tylenchorhynchus claytoni*, *Tylenchorhynchus dubius* and other *Tylenchorhynchus* species;This may also relate to methods for controlling damage to plants and parts thereof caused by plant parasitic nematodes, such as the citrus nematode (Citrus nematodes), the Tylenchulus species; the dagger nematode (Xiphinema species); and other plant parasitic nematode species such as Subanguina, Hypsoperine, Macroposthonia, Melinius, Punctodera, and Quinisulcius.

[0392] The compounds of the present invention may also be active against mollusks. Examples include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fluticum). fruticum); Cepaea (C. hortensis, C. nemoralis); Oclodina; Deroceras (D. agrentis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. truncata); Heliceria (H. itala, H. obvia); Helicidae; Helicigona albumum Examples include arbustorum, helicodiscus, helix (H. aperta), limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus), lymnaea, milax (M. gagates, M. marginatus, M. sowerbyi), opia, pomacea (P. canaticulata), vallonia, and zanitoides.

[0393] The term "crop" should be understood to include crop plants transformed using recombinant DNA technology so that they can synthesize one or more selectively acting toxins, such as known toxin-producing bacteria belonging particularly to the genus Bacillus.

[0394] Toxins that may be expressed by transgenic plants include, for example, insecticidal proteins, such as those derived from Bacillus cereus or Bacillus popilliae; or insecticidal proteins derived from Bacillus thuringiensis, such as δ-endotoxins like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C; or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or species such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc., such as species of the genus Photorhabdus (Photorhabdus spp.) or species of the genus Xenorhabdus (Xenorhabdus nematophilus) Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp (wasp) toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxin, plant lectins such as pea lectin, barley lectin or snowdrop lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, papain inhibitors; lysine, Examples include ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid xidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium blockers; larval hormone esterases; diuretic hormone receptors; stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0395] In connection with the present invention, it should be understood that δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3, or Vip3A, are also hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are generated by recombinant synthesis through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). For example, cleavage toxins such as cleavage Cry1Ab are known. In the case of modified toxins, one or more amino acids of the natural toxin are substituted. In such amino acid substitutions, a protease recognition sequence that does not naturally exist 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 International Publication No. 03 / 018810).

[0396] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in European Patent Publication No. 0374753, International Publication No. 93 / 07278, International Publication No. 95 / 34656, European Patent Publication No. 0427529, European Patent Publication No. 451878, and International Publication No. 03 / 052073.

[0397] The process for preparing such transformed plants is generally known to those skilled in the art and is described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acid and its preparation are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0398] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can belong to any of the insect taxonomic groups, but are commonly found in beetles (coleoptera), diptera (diptera), and moths (lepidoptera).

[0399] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrycin N-acetyltransferase (PAT) for resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).

[0400] Further examples of such transformed crops are as follows: 1. Bt11 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) resistant to attacks by the European pine borer (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of the cleavage Cry1Ab toxin. Bt11 maize has also achieved resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0401] 2. Bt176 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) resistant to attacks by the European pine borer (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of the Cry1Ab toxin. Bt176 maize has also achieved resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0402] 3. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, MIR604 maize, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in International Publication No. 03 / 018810.

[0403] 4. MON 863 maize, from Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0404] 5. IPC 531 Cotton, Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0405] 6. 1507 maize, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize to express the protein Cry1F to achieve resistance to certain lepidopteran insects and the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0406] 7. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. NK603×MON810 corn, registration number C / GB / 02 / M3 / 03. This is a conventional hybrid corn variety created by crossing the genetically modified varieties NK603 and MON 810. NK603×MON810 corn transgenically expresses the protein CP4 EPSPS obtained from the CP4 strain of Agrobacterium sp., thereby conferring resistance to the herbicide Roundup® (containing glyphosate). It also transgenically expresses the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain lepidopteran insects, including the corn borer.

[0407] Transgenic crops of insect-resistant plants are also described in the BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003 (http: / / bats.ch).

[0408] The term “crop” should be understood to include crop plants transformed using DNA recombination technology so that selectively active antipathogenic substances, such as so-called “infection-specific proteins” (PRP, see, for example, European Patent Application Publication No. 0392225), can be synthesized. Examples of such antipathogenic substances and transformed plants capable of synthesizing such antipathogenic substances are known, for example, from European Patent Application Publication No. 0392225, International Publication No. 95 / 33818, and European Patent Application Publication No. 0353191. Methods for producing such transformed plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications.

[0409] Crops may also be modified for enhanced resistance to fungal pathogens (e.g., Fusarium, Anthracnose, or Phytophthora), bacterial pathogens (e.g., Pseudomonas), or viral pathogens (e.g., potato leaf curl virus, tomato yellow necrosis virus, cucumber mosaic virus).

[0410] The crops also include varieties that have enhanced resistance to nematodes, such as soybean cyst nematodes.

[0411] Crops that are abiotically tolerant include, for example, those that have enhanced tolerance to drought, high salinity, high temperature, low temperature, frost, or light due to the expression of NF-YB or other proteins known in the art.

[0412] Examples of antipathogenic substances that may be expressed by such transgenic plants include ion channel blockers, such as sodium and calcium channel blockers, such as viral KP1, KP4, or KP6 toxins, stilbenzyl synthase, bibenzyl synthase, chitinase, glucanase, so-called "pathogenicity-associated proteins" (PRPs, see, for example, European Patent Application Publication No. 0392225), antipathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, International Publication No. 95 / 33818), or proteins or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes," as described in International Publication No. 03 / 000906).

[0413] Further areas of use of the compositions according to the present invention include the protection of stored articles and storage rooms from the types of pests described, as well as the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also the protection of humans, livestock and productive animals in particular in the sanitation sector.

[0414] 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, a method for controlling pests includes applying a composition of the present invention to target pests, their habitats, or surfaces or substrates by brushing, rolling, spraying, scattering, or dipping. For example, IRS (Indoor Residual Spray) application to surfaces, such as walls, ceilings, or floor surfaces, is intended by the method of the present invention. In another embodiment, such a composition is intended to be applied to substrates in the form of nets, clothing, bedding, curtains, and tents (or which may be used in the manufacture thereof), such as nonwoven or fabric materials.

[0415] In one embodiment, a method for controlling such pests involves applying an effective amount of the composition of the present invention to target pests, their habitats, or surfaces or substrates to achieve effective residual pesticidal activity on a surface or substrate. Such application can be carried out by brushing, rolling, spraying, scattering, or dipping the pesticidal composition of the present invention. For example, IRS application to surfaces, such as walls, ceilings, or floor surfaces, is intended by the method of the present invention to achieve effective residual pesticidal activity on the surface. In another embodiment, such a composition is intended for residual control of pests on substrates, such as textile materials in the form of nets, clothing, bedding, curtains, and tents (or materials that may be used in the manufacture thereof).

[0416] The base material, including the nonwoven fabric, cloth, or net to be treated, may be made of natural fibers such as cotton, raffia, jute, flax, sisal, burlap, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, or polyacrylonitrile. Polyester is particularly suitable. Methods for treating textiles are publicly known, for example, in International Publication 2008 / 151984, International Publication 2003 / 034823, U.S. Patent No. 5631072, International Publication 2005 / 64072, International Publication 2006 / 128870, European Patent No. 1724392, International Publication 2005113886, or International Publication 2007 / 090739.

[0417] A further area of ​​application for the compositions according to the present invention is the field of trunk injection / trunk treatment for all ornamental trees as well as all fruit trees and nut trees.

[0418] In the field of tree trunk injection / tree trunk treatment, the compounds according to the present invention are particularly suitable for wood-boring insects from the orders Lepidoptera and Coleoptera, as described above, and especially for the wood-boring organisms listed in Tables A and B below.

[0419] [Table 3]

[0420] [Table 4-1]

[0421] [Table 4-2]

[0422] [Table 4-3]

[0423] The present invention can also be used to control any pests that may be present in turfgrass, including, for example, rhinoceros beetles, caterpillars, fire ants, ground pearls, millipedes, woodlice, mites, mole crickets, scale insects, mealybugs, ticks, spittlebugs, golden long-horned bugs, and ground insects. The present invention can also be used to control pests at various stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0424] In particular, the present invention can be used to control ground insects (e.g., Cyclocephala spp. (e.g., masked beetle, C. lurida), Rhizotrogus spp. (e.g., European beetle, R. majalis), Cotinus spp. (e.g., blue-spotted beetle, C. nitida), Popillia spp. (e.g., bean beetle, P. japonica), Phyllophaga spp. (e.g., may / June beetle), and Ataenius). It can control turfgrass root-feeding pests, including turfgrass spp. (e.g., black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., red velvet beetle, M. castanea, and Tomarus spp.), ground pearl (Margarodes spp.), mole crickets (yellowish-brown, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana), and crane fly larvae (European crane fly, Tipula spp.).

[0425] The present invention can also be used to control turfgrass pests that inhabit straw, including armyworms (e.g., the fall armyworm Spodoptera frugiperda and the common armyworm Pseudaletia unipuncta), cutworms, weevils (Sphenophorus spp., e.g., S. venatus verstitus and S. parvulus), and sodweb worms (e.g., Crambus spp. and tropical sodweb worms, Herpetogramma phaeopteralis).

[0426] The present invention can also be used to control turfgrass pests that live on the ground and feed on turfgrass leaves, including stink bugs (e.g., the golden stink bug, Blissus insularis), the barnyard mite (Eriophyes cynodoniensis), the Japanese grass mealybug (Antonina graminis), the two-striped spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae), and the wheat aphid.

[0427] The present invention can also be used to control other pests of turfgrass, such as the red imported fire ant (Solenopsis invicta), which builds ant mounds in turfgrass.

[0428] In the field of hygiene, the compositions according to the present invention are active against external parasites such as mites, dust mites, scabies mites, chiggers, flies (stable flies and slug flies), parasitic fly larvae, lice, head lice, biting lice, and fleas.

[0429] Examples of such parasites are as follows: The order Anoplurida includes the genera Haematopinus, Linognathus, Pediculus, Phtirus, and Solenopotes.

[0430] The order Mallophagida includes the genera Trimenopon, Menopon, Trinoton, Bobicola, Werneckiella, Lepikentron, Damalina, Trichodectes, and Felicola.

[0431] Within the order Diptera and the suborders Nematocerina and Brachycerina, for example, there are genera such as Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., and Haematopota spp.), Philippomyia 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.), botflies (Hypoderma spp.), horseflies (Gasterophilus spp.), louse flies (Hippobosca spp.), Lipoptena spp., and sheep lice (Melophagus spp.).

[0432] Within the order Siphonapterida, for example, there are genera such as Pulex spp., Ctenocephalides spp., Xenopsylla spp., and Ceratophyllus spp..

[0433] Examples of true bugs in the order Heteropterida include the genera Cimex, Triatoma, Rhodnius, and Panstrongylus.

[0434] Examples of cockroaches in the order Blattaridae include the Eastern cockroach, the American cockroach, Blattela germanica, and the genus Supella.

[0435] The subclass Acaria (Acarida) and the orders Mesostigmata (opposchiloids and mesostigmata) include, for example, the genera Argas, Ornithodorus, Otobius, Ixodes, Amblyomma, Boophilus, Dermacentor, Haemophysalis, Hyalomma, Rhipicephalus, Dermanyssus, and Railietia. The genera include Pneumonyssus spp., Sternostoma spp., and Varroa spp..

[0436] In the suborders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, there are genera such as Acarapis, Cheyletiella, Ornithocheyletia, Myobia, Psorergates, Demodex, Trombicula, Listrophorus, Acarus, Tyrophagus, and Caloglyphus. spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp..

[0437] The compositions according to the present invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cards, leather, floor coverings and buildings from insect infestation.

[0438] The composition according to the present invention can be used, for example, against the following pests: rhinoceros 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, species of the genus Xyleborus, species of the genus Tryptodendron, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, species of the genus Sinoxylon.) and the long-horned beetle (Dinoderus minutus) and also Hymenoptera insects, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, as well as termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis and Reticulitermes lucifugus *Lucifugus*, *Mastotermes darwiniensis*, *Zootermopsis nevadensis*, and *Coptotermes formosanus*, as well as cornflowers, such as *Lepisma saccharina*.

[0439] The compounds according to the present invention can be used as pesticides in their unmodified form, but they are generally incorporated into compositions using various methods with additives such as carriers, solvents, and surfactants. The formulations may be in various physical forms, such as sprays, gels, wettable powders, water-dispersible granules, water-dispersible tablets, foamed pellets, emulsifying concentrates, microemulsifying concentrates, oil-in-water emulsions, oil-flowable formulations, aqueous dispersions, oily dispersions, sasporumulons, capsule suspensions, emulsifying granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as a carrier), 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 may be used directly or diluted before use. Dilution may be carried out, for example, with water, liquid fertilizers, trace elements, biological substances, oils, or solvents.

[0440] The formulations can be prepared, for example, by mixing an active ingredient with a formulation aid to obtain compositions in the form of micronized solids, granules, solutions, dispersions, or emulsions. The active ingredient may also be formulated with other aids, such as micronized solids, mineral oils, vegetable or animal-derived oils, modified vegetable or animal-derived oils, organic solvents, water, surfactants, or combinations thereof.

[0441] The active ingredient may also be contained in extremely small microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slow-release). Microcapsules typically have a diameter of 0.1 to 500 microns. They contain the active ingredient in an amount of approximately 25 to 95% by weight of the capsule. The active ingredient may be in the form of a solid whole, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulation membrane may include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and xanthogenic starch 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 fine particles in a solid matrix of a base material, but the microcapsules themselves are not encapsulated.

[0442] The compounding aids suitable for preparing the composition according to the present invention are known in themselves. Suitable liquid carriers include water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl ester of acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, 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, Ethyl Lactate, Ethylene Glycol, Ethylene Glycol Butyl Ether, Ethylene Glycol Methyl Ether, γ-Butyrolactone, Glycerol, Glycerol Acetate, Glycerol Diacetate, Glycerol Triacetate, Hexadecane, Hexylene Glycol, Isoamyl Acetate, Isobornyl Acetate, Isooctane, Isophorone, Isopropylbenzene, 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 High molecular weight alcohols such as oleic acid, 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 amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone may be used.

[0443] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, porous diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed, wheat flour, soybean flour, pumice, wood flour, walnut flour, lignin, and similar substances.

[0444] Numerous surfactants can be advantageously used in both solid and liquid formulations, particularly in formulations that can be diluted with a carrier before use. Surfactants can be anionic, cationic, nonionic, or polymeric, and these can be used as emulsifiers, wetting agents, or suspending agents or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, e.g., diethanolamine lauryl sulfate; salts of alkylaryl sulfonates, e.g., calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, e.g., nonylphenol ethoxylate; alcohol / alkylene oxide addition products, e.g., tridecyl alcohol ethoxylate; soaps, e.g., sodium stearate; salts of alkylnaphthalene sulfonates, e.g., sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates, e.g., sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, e.g., sorbitol oleate; quaternary amines, e.g., lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, e.g., polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters; as well as further substances described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).

[0445] Further auxiliary agents that may be used in insecticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoaming agents, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, flow enhancers, lubricants, dispersants, thickeners, antifreezes, fungicides, and liquid and solid fertilizers.

[0446] The composition according to the present invention may contain additives comprising vegetable oil or animal oil, mineral oil, alkyl esters of such oils, or mixtures 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 a desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or vegetable oil such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oil, alkyl esters of vegetable oils such as methyl derivatives, or animal oils such as fish oil or beef tallow. Preferred oil additives include C8 to C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 This includes methyl derivatives of fatty acids, such as methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are found in Compendium of Herbicide Adjuvants, 10 th This information is publicly available from Edition, Southern Illinois University, 2010.

[0447] The compositions of the present invention generally comprise 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound of the present invention, and 1 to 99.9% by weight of a formulation aid, preferably containing 0 to 25% by weight of a surfactant. Commercial products may preferably be formulated as concentrates, but end users typically utilize diluted formulations.

[0448] Application rates vary widely and depend on soil properties, application method, crop plants, pests being controlled, major weather conditions, and other factors influenced by the application method, timing, and target crop. As a general guideline, compounds can be applied at rates of 1 to 2000 l / ha, particularly 10 to 1000 l / ha.

[0449] A preferred formulation may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactants: 1-30%, preferably 5-20% Liquid carrier: 1-80%, preferably 1-35%

[0450] Powder: Active ingredient: 0.1-10%, preferably 0.1-5% Solid carrier: 99.9-90%, preferably 99.9-99%

[0451] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactants: 1-40%, preferably 2-30%

[0452] Wettable powder: Active ingredient: 0.5-90%, preferably 1-80% Surfactants: 0.5-20%, preferably 1-15% Solid support: 5-95%, preferably 15-90%

[0453] Granules: Active ingredient: 0.1-30%, preferably 0.1-15% Solid carrier: 99.5-70%, preferably 97-85%

[0454] The following examples further illustrate, but are not limiting, the present invention.

[0455] [Table 5]

[0456] This combination is thoroughly mixed with an auxiliary agent, and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder, which is then diluted with water to obtain a suspension of the desired concentration.

[0457] [Table 6]

[0458] This combination, when thoroughly mixed with the auxiliary agent and the mixture is thoroughly ground in a suitable mill, yields a powder that can be used directly for seed treatment.

[0459] [Table 7]

[0460] Emulsions of any required dilution ratio, which can be used for plant protection, can be obtained from this concentrate by dilution with water.

[0461] [Table 8]

[0462] Ready-to-use powders are obtained by mixing them with a carrier and grinding the mixture in a suitable mill. Such powders can also be used as dry fertilizers for seeds.

[0463] [Table 9]

[0464] This combination is mixed with an auxiliary agent, ground, and the mixture is wetted with water. This mixture is then extruded and dried with an airflow.

[0465] [Table 10]

[0466] The finely ground mixture is uniformly applied to kaolin moistened with polyethylene glycol in a mixer. In this way, dust-free coated granules are obtained.

[0467] [Table 11]

[0468] A finely ground combination is densely mixed with an auxiliary agent to obtain a suspension concentrate, from which a suspension of any desired dilution ratio can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial parasitism by spraying, pouring, or immersion.

[0469] [Table 12]

[0470] A finely ground combination is densely mixed with an auxiliary agent to obtain a suspension concentrate, from which a suspension of any desired dilution ratio can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial parasitism by spraying, pouring, or immersion.

[0471] Sustained-release capsule suspension Mix 28 parts of the combination with 2 parts of aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of defoamer, and 51.6 parts of water until the desired particle size is achieved. Add a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water to this emulsion. Stir the mixture until the polymerization reaction is complete. Stabilize the resulting capsule suspension by adding 0.25 parts of thickener and 3 parts of dispersant. This capsule suspension formulation contains 28% of the active ingredient. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for this purpose.

[0472] Examples of formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifying 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), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically preferred formulations combined with agriculturally acceptable auxiliaries. [Examples]

[0473] Preparation Examples: "Mp" stands for melting point (°C). Free radical represents a methyl group. 1 ¹H NMR measurements were recorded using a Brucker 400 MHz spectrometer, and chemical shifts are expressed in ppm relative to the TMS standard. Spectra were measured in deuterated solvents as described. Compounds were characterized using one of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound are retention time ("Rt", recorded in minutes) and measured molecular ion (M+H). + or (MH) - That was the case.

[0474] LCMS method and GCMS method: Method 1: Spectra were recorded using a Waters Corporation mass spectrometer equipped with an electrospray source (SQD, SQDII, or QDA single quadrupole mass spectrometer) (polarity: cation or anion, capillary: 0.8~3.00kV, cone: 5~30V, source temperature: 120~150°C, desolvation temperature: 350~600°C, cone gas flow rate: 50~150 l / h, desolvation gas flow rate: 650~1000 l / h, mass range: 110~950 Da) and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD. Column: Waters ULC 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 at constant composition for 0.2 min, then 10~100% B for 1.0 min, 100% B at constant composition for 0.2 min, 100~10% B for 0.05 min, 10% B at constant composition for 0.05 min.

[0475] Method 2: Spectra were recorded using a Waters Corporation mass spectrometer equipped with an electrospray source (SQD, SQDII, or QDA single quadrupole mass spectrometer) (polarity: cation or anion, capillary: 0.8~3.00kV, cone: 5~30V, source temperature: 120~150°C, desolvation temperature: 350~600°C, cone gas flow rate: 50~150 l / h, desolvation gas flow rate: 650~1000 l / h, mass range: 110~950 Da) and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD. Column: Waters ULC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Run time: 3.0 min; Solvent: A = Water + 5% MeOH + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH; Flow rate (ml / min): 0.85, Gradient: 10% B at constant composition for 0.2 min, then 10~100% B for 2.5 min, then 100% B at constant composition for 0.3 min.

[0476] Method 3: Spectra were recorded using a Waters mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) with an electrospray source (polarity: positive and negative polarity switch), capillary: 0.8~3.00kV, cone range: 25, source temperature: 120~150℃, desolvation temperature: 500~600℃, cone gas flow rate: 50 L / h, desolvation gas flow rate: 1000 L / h, mass range: 110~850 Da), and a Waters Acquity UPLC (Quaterary Solvent Manager), heated column compartment, and diode array detector. Column: Acquity UPLC HSS T3 C18 1.8 μm, 30 × 2.1 mm, temperature: 40℃, DAD wavelength range (nm): 200~400, solvent gradient: A = water + 5% acetonitrile + 0.05% HCOOH, B = acetonitrile + 0.1% HCOOH. Gradient: 10% B for 0 minutes; 10-50% B for 0-0.2 minutes; 50-100% B for 0.2-0.6 minutes; 100% B for 0.6-1.3 minutes; 100-10% B for 1.3-1.4 minutes; 10% B for 1.4-1.6 minutes; Flow rate (mL / min) 0.6.

[0477] Method 4: Spectra were recorded using an Agilent Technologies 6410 triple quadrupole mass spectrometer with an electrospray source (polarity: cation or anion, MS2 scan, capillary: 4.00kV, fragmenter: 100V, desolvation temperature: 350℃, gas flow rate: 11L / min, nebulizer gas: 45psi, mass range: 110~1000Da) and an Agilent 1200 series HPLC with quaternary pump, heated column compartment, and VWD detector. Column: KINETEX EVO C18 2.6μm, 50×4.6mm, temperature: 40℃, detector VWD wavelength: 254nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH. Gradient: 10% B for 0 minutes, 90% A; 100% B for 0.9-1.8 minutes; 100-10% B for 1.8-2.2 minutes; 10% B for 2.2-2.5 minutes; Flow rate (mL / min) 1.8.

[0478] Method 5: Spectra were recorded using an Agilent Technologies mass spectrometer (MSD-IQ mass spectrometer) equipped with an electrospray source (polarity: cation or anion, MS2 scan, capillary: 3.5kV, fragmenter: 110V, desolvation temperature: 325℃, gas flow rate: 13L / min, nebulizer gas: 55psi, mass range: 110~850Da) and an Agilent 1290 series HPLC: quaternary pump, heated column compartment and diode array detector. Column: AGILENT POROSHELL 120 EC-C18, 1.9μm, 50×2.1mm, temperature: 40℃, DAD wavelength range (nm): 190~400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH. Gradient: 0-0.5 minutes 10% B, 90% A; 1.2-1.5 minutes 95% B, 0.5% A; 1.8-2.5 minutes 10% B, 90% A: Flow rate (ml / min) 0.8.

[0479] Example 1: Preparation of 1-[5-ethylsulfonyl-6-[4-oxo-6-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P.1) [ka] Step 1: Preparation of (E)-3-(dimethylamino)-1-[2-hydroxy-5-(trifluoromethyl)phenyl]propa-2-en-1-one (intermediate I-1) [ka] A mixture of 1-[2-hydroxy-5-(trifluoromethyl)phenyl]ethenone (5.0 g, 24.49 mmol) and N,N-dimethyl-formamide dimethylacetal (4.24 mL, 31.83 mmol) was stirred at 100°C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain (E)-3-(dimethylamino)-1-[2-hydroxy-5-(trifluoromethyl)phenyl]propa-2-en-1-one. The crude material was used directly without purification. LC-MS (Method 3): Rt = 1.07 minutes, m / z 260 [M+H] + .

[0480] Step 2: Preparation of 3-iodo-6-(trifluoromethyl)chromen-4-one (intermediate I-2) [ka] Iodine (7.26 g, 28.6 mmol) was added to a solution of (E)-3-(dimethylamino)-1-[2-hydroxy-5-(trifluoromethyl)phenyl]propa-2-en-1-one (intermediate I-1 prepared as described above) (6.34 g, 24.5 mmol) in methanol (63.4 mL) cooled to 0°C. The reaction mixture was stirred at room temperature for 17 hours. The mixture was diluted with aqueous sodium thiosulfate, concentrated under reduced pressure, and then dissolved in ethyl acetate. The organic phase was washed twice with brine, dried over magnesium sulfate, and concentrated under reduced pressure using an isolute. The crude material was purified by flash chromatography using silica gel (0-30% ethyl acetate in cyclohexane) to obtain 3-iodo-6-(trifluoromethyl)chromen-4-one. 1 H NMR(400MHz,CDCl3)δ ppm 7.62(d,1H)7.94(dd,1H)8.35(s,1H)8.56(d,1H).

[0481] Step 3: Preparation of [4-oxo-6-(trifluoromethyl)chromen-3-yl]boronic acid (intermediate I-3) [ka] To a solution of 3-iodo-6-(trifluoromethyl)chromen-4-one (intermediate I-2 prepared as described above) (2.0 g, 5.9 mmol) in THF (10 mL) cooled to -78°C, isopropyl magnesium chloride lithium chloride complex (1.3 M in THF) (6.3 mL, 8.2 mmol) was added dropwise. The reaction mixture was stirred at -78°C for 15 minutes, after which trimethyl borate (1.7 mL, 15 mmol) was added. The reaction mixture was then warmed to room temperature and stirred for 2 hours. The mixture was diluted with aqueous ammonium chloride, the product was extracted twice with ethyl acetate, and the combined organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude material was used directly without purification. LC-MS (Method 3): Rt = 1.00 min, m / z 259 [M+H] + .

[0482] Step 4: Preparation of 1-(6-bromo-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrine (intermediate I-4) [ka] To a solution of 1-(6-amino-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitride (prepared as described in International Publication No. 2020 / 174094) (6.95 g, 31.7 mmol) in ethylene dibromide (69.5 mL), copper(II) bromide (10.7 g, 47.5 mmol, 1.5 equivalents) was added. The reaction mixture was stirred at room temperature for 10 minutes, after which isoamyl nitrite (6.52 mL, 47.5 mmol, 1.5 equivalents) was added dropwise. The mixture was further stirred at room temperature for 4.5 hours. The reaction mixture was diluted with aqueous sodium bicarbonate and ethyl acetate, and then filtered through Celite. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with water and aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure using an isolute. The crude material was purified by flash chromatography with silica gel (ethyl acetate in cyclohexane) to obtain the desired product as a yellow solid. LCMS (method 1): Rt=0.99 min, m / z 283 / 285[M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.44(t,3H),1.47(m,2H),1.83(m,2H),3.01(q,2H),7.45(d,1H),7.94(d,1H).

[0483] Step 5: Preparation of 1-(6-bromo-5-ethylsulfonyl-3-pyridyl)cyclopropanecarbonitride (intermediate I-5) [ka] At 0°C, 3-chloroperbenzoic acid (7.83 g, 34 mmol, 2.3 equivalents) was added in several portions to a solution of 1-(6-bromo-5-ethylsulfanyl-3-pyridyl)cyclopropanecarbonitrile (intermediate I-4 prepared as described above) (4.19 g, 14.8 mmol) in ethyl acetate (59 mL), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched dropwise by the addition of aqueous sodium bisulfite solution and stirred for 10 minutes, then diluted with aqueous sodium bicarbonate solution, and the product was extracted with ethyl acetate. The organic phase was washed with aqueous sodium hydroxide solution, then with aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude material was used directly without purification. LCMS (Method 1): Rt = 0.77 minutes, m / z 315 / 317 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.34(t,3H),1.55(m,2H),1.94(m,2H),3.56(q,2H),8.17(d,1H),8.67(d,1H).

[0484] Step 6: Preparation of 1-[5-ethylsulfonyl-6-[4-oxo-6-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P.1) [ka] To a solution of 1-(6-bromo-5-ethylsulfonyl-3-pyridyl)cyclopropanecarbonitride (intermediate I-5 prepared as described above) (0.311 g, 0.988 mmol) and [4-oxo-6-(trifluoromethyl)chromen-3-yl]boronic acid (intermediate I-3 prepared as described above) (0.255 g, 0.988 mmol) in acetonitrile (5.1 mL) degassed with argon, 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex was added at 0°C along with dichloromethane (0.084 g, 0.098 mmol), water (1.9 mL), and potassium carbonate (0.314 g, 2.27 mmol). The mixture was stirred at 60°C for 20 minutes. The reaction mixture was cooled to room temperature, diluted with water, and the product was extracted twice with ethyl acetate. The combined organic phases were washed with aqueous sodium hydroxide solution and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography using silica gel (0-70% ethyl acetate in cyclohexane) to obtain 1-[5-ethylsulfonyl-6-[4-oxo-6-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P.1) as a solid. LCMS (Method 3): Rt = 1.13 minutes, m / z 449 [M+H] + . 1 H NMR(400MHz,CDCl3)1.38(t,3H)1.61-1.65(m,2H)1.99(d,2H)3.36-3.53(m, 2H)7.70(d,1H)7.99(dd,1H)8.13(s,1H)8.20(d,1H)8.58(d,1H)8.95(d,1H).

[0485] Example 2: Preparation of 1-[6-(6-bromo-4-oxochromen-3-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile (compound P.5) [ka] Step 1: Preparation of 1-[6-[2-(5-bromo-2-hydroxyphenyl)-2-oxo-ethyl]-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitride (intermediate I-6) [ka] Potassium carbonate (4.82 g, 34.877 mmol) was added to a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (3.0 g, 13.951 mmol) and 1-(6-bromo-5-ethylsulfonyl-3-pyridyl)cyclopropane carbonitride (intermediate I-5 prepared as described above) (5.05 g, 16.044 mmol) in dimethyl sulfoxide (13.5 mL). The mixture was heated at 60°C for 21 hours. The aqueous layer was extracted with ethyl acetate (twice), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography using silica gel (10-40% ethyl acetate in cyclohexane) to obtain 1-[6-[2-(5-bromo-2-hydroxyphenyl)-2-oxo-ethyl]-5-ethylsulfonyl-3-pyridyl]cyclopropane carbonitride and tautomer enols. LCMS (method 3): Rt=1.08 min, m / z 449 / 451[M+H] + .

[0486] Step 2: Preparation of 1-[6-(6-bromo-4-oxochromen-3-yl)-5-ethylsulfonyl-3-pyridyl]-cyclopropanecarbonitride (compound P.5) [ka] 1-[6-[2-(5-bromo-2-hydroxyphenyl)-2-oxo-ethyl]-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitri and a tautomer enol (intermediate I-6 prepared as described above) (0.0.25 g, 0.528 mmol) were suspended in N,N-dimethylformamide (1.2 mL), and N,N-dimethylformamide dimethylacetal (0.179 mL, 1.32 mmol) was added. The reaction mixture was stirred at 120°C for 2 hours. The reaction mixture was concentrated under reduced pressure, and the crude material was purified by flash chromatography using silica gel (ethyl acetate in cyclohexane) to obtain 1-[6-(6-bromo-4-oxo-chromen-3-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitriri (compound P.5) as a brown solid. LCMS (method 3): Rt=1.09 min, m / z 459 / 461[M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.35(t,3H),1.52-1.62(m,2H),1.97(br d,2H),3.33-3.47(m,2H),7.46(d,1H),7.83(dd,1H),8.09(s,1H),8.18(d,1H),8.39(d,1H),8.93(d,1H).

[0487] Example 3: Preparation of 1-[5-ethylsulfonyl-6-[6-(4-fluorophenyl)-4-oxo-chromen-3-yl]-3-pyridyl]-cyclopropanecarbonitride (compound P.8) [ka] To a solution of 1-[6-(6-bromo-4-oxochromen-3-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile (compound P.5) (0.083 g, 0.1717 mmol) in toluene (3.4 mL) and water (0.68 mL), sodium carbonate (0.045 g, 0.4292 mmol) and (4-fluorophenyl)boronic acid (0.084 g, 0.6009 mmol) were added. The reaction mixture was purged with nitrogen for 30 minutes, and then tetrakis(triphenylphosphine)palladium (0) (0.020 g, 0.01717 mmol) was added to the reaction mixture. The resulting reaction was stirred at 90°C for 6 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography using silica gel (10-50% ethyl acetate in cyclohexane) to obtain 1-[5-ethylsulfonyl-6-[6-(4-fluorophenyl)-4-oxo-chromene-3-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P.8) as a brown solid. LC-MS (Method 3): Rt = 1.30 minutes, m / z 475 [M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 1.35(m,3H),1.59-1.69(m,2H),1.97(br d,2H),3.40-4.43(m,2H),7.18(t,2H),7.61-7.66(m,3H),7.94(dd,1H),8.12(s,1H),8.20(d,1H),8.41(d,1H),8.95(d,1H)

[0488] [Table 13-1]

[0489] [Table 13-2]

[0490] The activity of the compositions according to the present invention can be considerably broadened by the addition of other insecticidal, acaricidal, and / or fungicidal active ingredients to suit general situations. Mixtures of the compound of Formula I with other insecticidal, acaricidal, and / or fungicidal active ingredients may also have even more remarkable advantages, which can be described in a broader sense as synergistic activity. For example, better resistance by plants, reduced plant toxicity, and control over insects during their production, e.g., during grinding or mixing, during storage or use, at different stages of development or with better behavior.

[0491] Suitable additives to the active ingredients in this specification include, for example, the following types of active ingredients: organophosphorus compounds, nitrophenol derivatives, thiourea, juvenile hormones, formamidine, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids, and Bacillus thuringiensis preparations.

[0492] The following combinations of the 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 defined in Tables A-1 to A-48, B-1 to B-48, C-1 to C-48, D-1 to D-48 and P of the present invention"): Auxiliary agent selected from the group of substances consisting of petroleum (alternative name) (628) + TX; Abamectin + TX, Acexinosil + TX, Acetamiprid + TX, Acetoprol + TX, Acrinatrin + TX, Acinonapir + TX, Afidopiropen + TX, Afoxolaner + TX, Alanicarb + TX, Arethrin + TX, α-Cypermethrin + TX, α-Methrin + TX, Amidoflumet + TX, Aminocarb + TX, Azocyclotin + TX, Bensultap + TX, Benzoximate + TX, Benzpyrimoxane + TX, β-Cyfluthrin + TX, β-Cypermethrin + TX, Bifenazate + TX, Bifenthrin + TX, Binapacril +TX, Biorethrin+TX, S-Biorethrin+TX, Violethmetrin+TX, Bistriflurone+TX, Broflanilide+TX, Broflutrinate+TX, Bromophos-ethyl+TX, Buprofezin+TX, Butocarboxim+TX, Kazusaphos+TX, Carbaryl+TX, Carbosulfan+TX, Cartap+TX, CAS No.: 1632218-00-8+TX, CAS No.: 1808115-49-2+TX, CAS No.: 2032403-97-5+TX, CAS No.: 2044701-44-0+TX, CAS No.: 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 number: 1990457-57-2+TX, CAS number: 1990457-77-6+TX, CAS number: 1990457-66-3+TX, CAS number: 1990457-85-6+TX, CAS number: 2220132-55-6+TX, CAS number: 1255091-74-7+TX, CAS number: RNA (Leptinotarsa ​​desemlinator) Decemlineata-specific recombinant double-strand interference GS2) + TX, CAS No.: 2719848-60-7 + TX, CAS No.: 1956329-03-5 + TX, Chlorantraniliprole + TX, Chlordan + TX, Chlorfenapyr + TX, Chloroprallethrin + TX, Chromafenozide + TX, Clenpyrin + TX, Chloetocarb + TX, Clothianidin + TX, 2-Chlorophenyl N-methylcarbamate (CPMC) + TX, Cyanophene phosphatidyl S+TX, Cyantraniliprole+TX, Cyclaniliprole+TX, Cyclobtrifluram+TX, Cycloprothrin+TX, Cycloxapride+TX, Cyenopyrafen+TX, Cyetopyrafen (or etopyrafen)+TX, Cyflumetofen+TX, Cyfluthrin+TX, Cyhalodiamide+TX, Cyhalothrin+TX, Cypermethrin+TX, Cyphenothrin+TX, Cyprofuranilide+TX, Cyromazine+TX, Deltamethrin+TX, Diafene Nthiuron + TX, Dialiphos + TX, Dibrom + TX, Dichloromezothiaz + TX, Diflovidazine + TX, Diflubenzuron + TX, Dimepropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Emamectin (or Emamectin benzoate) + TX, Empenthrin + TX, ε-Monfluorothrin + TX, ε-Metofluthrin + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole +TX, etofenprox+TX, etoxazole+TX, Funfar+TX, phenazaquin+TX, fenfluthrin+TX, fenmezoditiaz+TX, fenitrothion+TX, phenobucarb+TX, phenothiocarb+TX, phenoxycarb+TX, fenpropathrin+TX, fenpyroximate+TX, fensulfothione+TX, fenthion+TX, triphenyltin acetate+TX, fenvalerate+TX, fipronil+TX,Frometoquin + TX, flonicamide + TX, fluacrypyrim + TX, fluazindolin + TX, fluazuron + TX, flubendiamide + TX, flubendimine + TX, flulchlordiniliprole + TX, flucitrinate + TX, flucicolone + TX, flucitrinate + TX, fluensulfone + TX, flufenelim + TX, flufenprox + TX, flufiprole + TX, fluhexaphon + TX, Flumethrin + TX, Fluopyram + TX, Flupenthiofenox + TX, Flupyradiflon + TX, Flupyrimin + TX, Flularaner + TX, Fluvalinate + TX, Fluxamethamide + TX, Fostiazate + TX, γ-Cyhalotrin + TX, Guadipyr + TX, Halofenozide + TX, Halfenprox + TX, Heptafluthrin + TX, Hexithiazox + TX, Hydramethylnon + TX, Imiciaphos + T X, Imidacloprid + TX, Imiprothrin + TX, Indazapiroxameth + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Isocycloceram + TX, Isothioate + TX, Ivermectin + TX, κ-Bifenthrin + TX, κ-Tefluthrin + TX, λ-Cyhalotrin + TX, Lepimectin + TX, Lotilaner + TX, Lufenuron + TX, Metaflumizone + TX, Metaldehyde + TX Metam+TX, Methomyl+TX, Methoxyphenozide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalbate+TX, Milbemectin+TX, Monfluorothrin+TX, Niclosamide+TX, Nicofluprole+TX; Nitenpyram+TX, Nichiazine+TX, Omethoate+TX, Oxamyl+TX, Oxazosulfyl+TX, Parathion-ethyl+TX, Permethrin+TX, Phenothrin+TX, Phosphocarb + TX, Piperonyl butoxide + TX, Pyrimicarb + TX, Pyrimiphos-ethyl + TX, Pyrimiphos-methyl + TX, Polyhedra disease virus + TX, Prallethrin + TX, Profenofos + TX, Profluthrin + TX, Propargit + TX, Propetamphos + TX, Propoxar + TX, Prothiofos + TX, Protrefene bute + TX, Piflubmid + TX, Pymetrozine + TX, Piraclofos + TX, Pirafluprole + TX, Pyridaben + TX, Pyridaryl + TX, Pyrifluquinazon + TX, Pyrimidifen + TX, Pyriminos Trobin + TX, Pyriprole + TX, Pyriproxyfen + TX, Resmethrin + TX, Saloraner + TX, Selamectin + TX, Silafluofen + TX, Spinetoram + TX, Spinosad + TX, Spirobudiphen + TX; Spirodiclofen + TX, Spiromesifen + TX, Spiropidione + TX, Spirotetramato + TX, Spidoxamato + TX, Sulfoxaflor + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimifos + TX, Tefluthrin + TX, Temephos + TX, Tetrachlorantraniliprole + TX, Tetradi Hon+TX, Tetramethrin+TX, Tetramethylfluthrin+TX, Tetranactin+TX, Tetraniliprole+TX, θ-Cypermethrin+TX, Thiacloprid+TX, Thiamethoxam+TX, Thiocyclam+TX, Thiodicarb+TX, Thiofanox+TX, Thiometon+TX, Thiosultap+TX, Tigoraner+TX, Thiolantraniliprole+TX; Thioxazafen+TX, Tolfenpyrad+TX, Toxafen+TX, Tralomethrin+TX, Transfluthrin+TX, Triazamate+TX, Triazophos+TX, Tri Chlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Trifluenfuronate + TX, Triflumezopyrim + TX, Cyclopyrazoflor + TX, ζ-Cypermethrin + TX, Fermented products derived from seaweed extract and Melasse + TX, Fermented products derived from seaweed extract and Melasse containing urea + TX, Amino acids + TX, Potassium and molybdenum and EDTA-chelated manganese + TX, Seaweed extract and fermented plant products + TX, Fermented plant products containing seaweed extract and plant hormones + TX, Vitamins + TX, EDTA-chelated copper + TX, Zinc + TX and Iron + TX,Azadirachtin + TX, Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL acceptance number B-21 618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL acceptance number B-21664) + TX, Bacillus pumilus (NRRL acceptance number B-30087) + TX, Bacillus pumilus AQ717 (NRRL acceptance number B-21662) + TX, Bacillus genus sp.)AQ178 (ATCC acceptance number 53522) + TX, Bacillus sp. AQ175 (ATCC acceptance number 55608) + TX, Bacillus sp. AQ177 (ATCC acceptance number 55609) + TX, unspecified Bacillus subtilis + TX, Bacillus subtilis AQ153 (ATCC acceptance number 55614) + TX, Bacillus subtilis AQ30002 (NRRL acceptance number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL acceptance number B-50455) + TX, Bacillus subtilis Bacillus subtilis AQ713 (NRRL acceptance number B-21661) + TX, Bacillus subtilis AQ743 (NRRL acceptance number B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL acceptance number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL acceptance number B-21530) + TX, Bacillus thuringiensis subspec. kurstaki BMP 123 + TX, Beauveria bassiana + TX, D-limonene + TX, Granulovirus + TX,Harpin + TX, Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa zea nuclear polyhedrosis virus + TX, Heliothis virescens nuclear polyhedrosis virus + TX, Heliothis punctigera nuclear polyhedrosis virus + TX, Metarhizium spp. + TX, Muscodor albus 620 (NRRL acceptance number 30547) + TX, Muscodor roseus A3-5 (NRRL acceptance number 30548) + TX, Neem tree products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lyracinus lilacinus)+TX, Pasteuria nishizawae+TX, Pasteuria penetrans+TX, Pasteuria ramosa+TX, Pasteuria thornei+TX, Pasteuria usgae+TX, P-cymene+TX, Plutella xylostella granuloma virus+TX, Plutella xylostella nuclear polyhedra virus+TX, polyhedra virus+TX, pyrethrum+TX, QRD 420 (terpenoid blend)+TX, QRD 452 (terpenoid blend)+TX, QRD 460 (terpenoid blend)+TX, Quillaya saponaria saponaria)+TX, Rhodococcus globerulus AQ719 (NRRL acceptance number B-21663)+TX, Spodoptera frugiperda nuclear polyhedrosis virus+TX, Streptomyces galbus (NRRL acceptance number 30232)+TX,Streptomyces sp. (NRRL acceptance number B-30145) + TX, terpenoid blend + TX, and Verticillium spp. + TX; Algaecides selected from the group consisting of bethoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, diclon (1052) + TX, dichlorophen (232) + TX, endotar (295) + TX, fenthin (347) + TX, slaked lime [CCN] + TX, nabam (566) + TX, quinoclamin (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347), and triphenyltin hydroxide (IUPAC name) (347) + TX; Anthelmintics 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), and thiophanate (1435) + TX; A birdicide selected from the group consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridine-4-amine (IUPAC name) (23), and strychnine (745) + TX; 1-H-pyridine-2-thion (IUPAC name) (1222) + TX, 4-(quinoxaline-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, dichlorophene (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + A bactericide selected from the group of substances consisting of TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrine (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecrophthalam (766) + TX, and thiomersal (alternative name) [CCN] + TX; 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. islaensis 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.tenebryonis(scientific name)tenebrionis) (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa) (scientific name) (293) + TX, desert parasitic wasp (Eretmocerus eremicus) (alternative name) (300) + TX, American tobacco budworm (Helicoverpa zea) NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, ladybug (Hippodamia convergens) (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, cutworm (Mamestra brassicae)NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name)(522)+TX, Metarhizium anisopliae var.acridum (scientific name)(523)+TX, Metarhizium anisopliae var.anisopliae (scientific name)(523)+TX, Neodiprion sertifer NPV and N. reconti (N.lecontei)NPV (alternative name)(575)+TX, Orius spp. (alternative name)(596)+TX, Paecilomyces fumosoroseus (alternative name)(613)+TX, Phytoseiulus persimilis (alternative name)(644)+TX, Spodoptera exigua polycapsid nucleus polyhedrosis virus (scientific name)(741)+TX, Steinernema bibionis (alternative name)(742)+TX, Steinernema carpocapsae (alternative name)(742)+TX, Steinernema felthiae (Steinernema feltiae) (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus osidentalis A biological agent selected from the group of substances consisting of *Occidentalis* (alternative name) (844) and *Verticillium lecanii* (alternative name) (848) + TX. A soil sterilizer selected from the group consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX, A sterilizing agent selected from the group of substances consisting of aphorate [CCN]+TX, bisadil (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 aphorate [CCN]+TX, molzide [CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine (alternative name) [CCN], and uredepa (alternative name) [CCN]+TX; (E)-deca-5-en-1-yl acetate and (E)-deca-5-en-1-ol (IUPAC name)(222)+TX, (E)-trideca-4-en-1-yl acetate (IUPAC name)(829)+TX, (E)-6-methylhepta-2-en-4-ol (IUPAC name)(541)+TX, (E,Z)-tetradeca-4,1 0-diene-1-ylacetate (IUPAC name)(779)+TX, (Z)-dodeca-7-ene-1-ylacetate (IUPAC name)(285)+TX, (Z)-hexadeca-11-enal (IUPAC name)(436)+TX, (Z)-hexadeca-11-ene-1-ylacetate (IUPAC name)(437)+TX, (Z)-hex Sadeca-13-en-11-in-1-ylacetate (IUPAC name) (438) + TX, (Z)-icosa-13-en-10-on (IUPAC name) (448) + TX, (Z)-tetradeca-7-en-1-ar (IUPAC name) (782) + TX, (Z)-tetradeca-9-en-1-ol (IUPAC name) (783) + TX, ( Z)-Tetradeca-9-ene-1-ylacetate (IUPAC name)(784)+TX, (7E,9Z)-Dodeca-7,9-diene-1-ylacetate (IUPAC name)(283)+TX, (9Z,11E)-Tetradeca-9,11-diene-1-ylacetate (IUPAC name)(780)+TX, (9Z,12E)-Tetradeca-9,12-Diene-1-yl acetate (IUPAC name) (781) + TX, 14-Methyloctadeca-1-ene (IUPAC name) (545) + TX, 4-Methylnonan-5-ol and 4-Methylnonan-5-one (IUPAC name) (544) + TX, α-Multistriatin (alternative name) [CCN] + TX, Brevicomin (alternative name) [CCN] + TX, Chodrelua (alternative name) [CCN] + TX, Chodremon (alternative name) (167) + TX, Kyurua (alternative name) (179) + TX, Dispa Lua (277) + TX, Dodeca-8-en-1-ylacetate (IUPAC name) (286) + TX, Dodeca-9-en-1-ylacetate (IUPAC name) (287) + TX, Dodeca-8 + TX, 10-dien-1-ylacetate (IUPAC name) (284) + TX, Dominicala (alternative name) [CCN] + TX, 4-methyloctanoate ethyl (IUPAC name) (317) + TX, Eugenol (alternative name) [CCN] + TX, Frontalin (alternative name) [CCN] + TX, Goss yplure(registered trademark) (alternative name: 1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) (420)+TX, (420)+TX, Grandlua(421)+TX, Grandlua I(alternative name)(421)+TX, Grandlua II(alternative name)(421)+TX, Grandlua III(alternative name)(421)+TX, Grandlua IV(alternative name)(421)+TX, Hexalua[CCN]+TX, Ipsdienol(alternative name)[CCN ]+TX, Ipsenol (alternative name) [CCN]+TX, Japonilua (alternative name) (481)+TX, Lineatin (alternative name) [CCN]+TX, Littleua (alternative name) [CCN]+TX, Lupulua (alternative name) [CCN]+TX, Medruua [CCN]+TX, Megatomoic acid (alternative name) [CCN]+TX, Methyl eugenol (alternative name) (540)+TX, Muscarua (563)+TX, Octadeca-2,13-diene-1-yl acetate (IUPAC name) (588)+TX, Octadeca-3,Insect pheromones selected from the group of substances consisting of 13-diene-1-ylacetate (IUPAC name)(589)+TX, olflurua (alternative name)[CCN]+TX, orictalua (alternative name)(317)+TX, ostramon (alternative name)[CCN]+TX, sigurua[CCN]+TX, solzidine (alternative name)(736)+TX, sulcatol (alternative name)[CCN]+TX, tetradeca-11-ene-1-ylacetate (IUPAC name)(785)+TX, trimedlua(839)+TX, trimedlua A (alternative name)(839)+TX, trimedlua B1 (alternative name)(839)+TX, trimedlua B2 (alternative name)(839)+TX, trimedlua C (alternative name)(839), and trunk-col (alternative name)[CCN]+TX, Insect repellents selected from the group consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyrronoxyl (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, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethylhexanediol (1137) + TX, hexaamide [CCN] + TX, methquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN], and picaridin [CCN] + TX; Bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloetocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachloro A molluscicide selected from the group of substances consisting of lophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tadimucarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, and pyriprole [394730-71-3] + TX; AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / chemical abstract name) (1045) + TX, 1,2-dichloropropane (IUPAC / chemical abstract name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / chemical abstract name) (IUPAC name)(1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine(IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiadinane-3-ylacetic acid(IUPAC name)(1286)+TX, 6-isopentenylaminopurine(alternative name)(210)+TX, abamectin(1)+TX, acetoprole[CCN]+TX, aranicarb(15)+TX, aldicarb(16)+TX, aldoxycarb(863)+TX, AZ60541 (compound code) + TX, bencrotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, kazusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, chloetocarb (999) + TX, cyclobutriflurum + TX, cytokinin (alternative name) (210) + T X, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidaphos (1044) + TX, Diclofenthion (1051) + TX, Diclifos (alternative name) + TX, Dimethoate (262) + TX, Doramectin (alternative name) [CCN] + TX, Emamectin (291) + TX, Emamectin benzoate (291) + TX, Eprinomectin (alternative name) [CCN] + TX, Etoprofos (312) + TX, Ethyl dibromide Len(316)+TX, Fenamifos(326)+TX, Fenpyrad(alternative name)+TX, Fensulfothione(1158)+TX, Fosthiazate(408)+TX, Fosthiethane(1196)+TX, Furfural(alternative name)[CCN]+TX, GY-81(development code)(423)+TX, Heterophos[CCN]+TX, Iodomethane(IUPAC name)(542)+TX, Isamidophos(1230)+TX, Isazofos(1231)+TX, Ibe Lumectin (alternative name) [CCN] + TX, Kinetin (alternative name) (210) + TX, Mecarphone (1258) + TX, Metam (519) + TX, Metam-potassium (alternative name) (519) + TX, Metam-sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alternative name) [CCN] + TX, Moxidectin (alternative name) [CCN] + TX, Mulberry dark spot disease fungus (MyrotheciumVerrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidone (639) + TX, phosphocarb [CCN] + TX, sebuphos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbuphos (773) + TX, tetrachlorothiophene (IU Nematicidals selected from the group consisting of substances comprising PAC / chemical abstract name)(1422)+TX, thiafenox(alternative name)+TX, thionazine(1434)+TX, triazophos(820)+TX, triazurone(alternative name)+TX, xylenol[CCN]+TX, YI-5302(compound code), and zeatin(alternative name)(210)+TX, fluensulfone[318290-98-1]+TX, and fluopyram+TX. A nitrification inhibitor selected from the group consisting of potassium ethylxanthogenicate [CCN] and nitrapyrine (580) + TX; A plant activator selected from the group of substances consisting of acibenzolar(6)+TX, acibenzolar-S-methyl(6)+TX, probenazole(658), and Japanese knotweed (Reynoutria sachalinensis) extract (alternative name)(720)+TX; 2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(Quinoxaline-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodiphacomum (89) + TX, bromadiolon (containing alpha-bromadiolon) (mu) + TX, Bromethaline (92) + TX, Calcium cyanide (444) + TX, Chloralose (127) + TX, Chlorophacinone (140) + TX, Cholecalciferol (alternative name) (850) + TX, Coumacrole (1004) + TX, Coumafuryl (1005) + TX, Coumatetralyl (175) + TX, Crimidine (1009) + TX, Diphenacome (246) + TX, Difethialone (249) + TX, Diphacinone (273) + TX, Ergocalciferol (301) + TX, Furocumafen (357) + TX, Fluoroacetamide (379) + TX, Flupropadine (1183) + TX, Flupropadine hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, Hydrogen cyanide (444) + TX, Iodomethane (IUPAC name) (542) + TX, Lithodan (430) + TX, Magnesium phosphide (IUPAC name) (640) + TX, Methyl bromide (537) + TX, Norbormid (1318) + TX, Fosacetim (1336) + TX, Ho A rodenticide selected from the group of substances consisting of sphing (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pidocroline (1341) + TX, potassium arsenite [CCN] + TX, pyrinulone (1371) + TX, siriloside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851), and zinc phosphide (640) + TX. Synergistic agents selected from the group consisting of 2-(2-butoxyethoxy)ethylpiperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone (IUPAC name) (903) + TX, farnesol and nerolidol (alternative name) (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) and sulfoxide (1406) + TX; Animal repellents selected from the group consisting of substances comprising anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatin (422) + TX, guazatin acetate (422) + TX, methiocarb (530) + TX, pyridine-4-amine (IUPAC name) (23) + TX, thyram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN], and thyram (856) + TX; A virucidal agent selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX; A wound protectant selected from the group consisting of mercuric(512)+TX, octylinone(590), and thiophanate-methyl(802)+TX; 1,1-Bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-Dichlorophenylbenzenesulfonate + TX, 2-Fluoro-N-methyl-N-1-cinnamaldehyde + TX, 4-Chlorophenylphenylsulfone + TX, Acetoprole + TX, Aldoxycarb + TX, Amidithione + TX, Amidothioate + TX, Amitone + TX, Amitone Hydrogen Oxalate + TX, Amitraz + TX, Aramite + TX, Arsenic Trioxide + TX, Azobenzene + TX, Azothoate + TX, Benomyl + TX, Benoxaphos + TX, Benzylbenzoate Fragrance salt + TX, Bixafen + TX, Brofenvalerate + TX, Bromocyclene + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxime + TX, Butoxycarboxime + TX, Butylpyridaben + TX, Calcium polysulfate + TX, Canfechlor + TX, Carbanolate + TX, Carbophenothion + TX, Simiazole + TX, Tinomethionate + TX, Chlorbenside + TX, Chlordimeform + TX, Chlordimeform hydrochloride + TX, Chlorphenetol + TX, Chlorfensone + TX Chlorofensilfide + TX, Chlorobenzilate + TX, Chloromebform + TX, Chloromethirone + TX, Chloropropylate + TX, Chlorthiophos + TX, Synerin I + TX, Synerin II + TX, Synerin + TX, Closantel + TX, Coumaphos + TX, Crotamiton + TX, Clothoxyphos + TX, Cuflaev + TX, Cyanthoate + 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, Diclofluanide+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Dynex+TX, Dynexdicrexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinoctone+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervon+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX, Endothion+TX,Epilinomectin + TX, Ethoate-methyl + TX, Etrimophos + TX, Phenazaflor + TX, Fenbutatin oxide + TX, Phenothiocarb + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentriphanil + TX, Flubenzimin + TX, Flucycloxurone + TX, Fluenetil + TX, Fluolbenside + TX, FMC 1137 + TX, Formethanate + TX, Formethanate hydrochloride + TX, Formparanate + TX, γ-HCH + TX, Gliodin + TX, Halfenprox + TX, Hexadecylcyclopropane carboxylate + TX, Isocarbofos + TX, Jasmolin I + TX, Jasmolin II + TX, Jodofenphos + TX, Lindan + TX, Malonoben + TX, Mecarbam + TX, Mephosphoran + TX, Mesulfen + TX, Methacryphos +TX, Methyl bromide +TX, Methylcarb +TX, Mexacalbate +TX, Milbemycin oxime +TX, Mipahox +TX, Monoclotophos +TX, Morphothion +TX, Moxidectin +TX, Nared +TX, 4-Chloro-2-(2-Chloro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one +TX, Niflulidide +TX, Nikcomycin +TX, Nitrilacarb +TX, Nitrilacarb 1:1 salt Zinc complex + TX, Omethoate + TX, Oxydeprophos + TX, Oxydisulfon + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fencapton + TX, Phosalone + TX, Phosphamide + TX, Polychloroterpene + TX, Polynactin + TX, Proclonol + TX, Promacil + TX, Propoxul + TX, Protidathion + TX, Protoate + TX, Pyrethrin I + TX, Pyrethrin II +TX, Pyrethrin+TX, Pyridafenthion+TX, Pyrimitate+TX, Quinalphos+TX, Quinthiophos+TX, R-1492+TX, Phosglycine+TX, Rotenone+TX, Shuradan+TX, Sebuphos+TX, Selamectin+TX, Sofamide+TX, SSI-121+TX, Sulfiram+TX, Sulfuramide+TX, Sulfotep+TX, Sulfur+TX, Diflovidazine+TX, τ-Fulvalinate+TX, TEPP+TX, Terbam+TX,Tetradiphon + TX, Tetrasul + TX, Thiafenox + TX, Thiocarboxim + TX, Thiofanox + TX, Thiometon + TX, Thioquinox + TX, Turingiencin + TX, Triamiphos + TX, Triatene + TX, Triazophos + TX, Triazurone + TX, Triphenophos + TX, Trinactin + TX, Bamidthion + TX, Vaniliprole + TX, Bethoxazine + TX, Copper nioctanonate + TX, Copper sulfate + TX, Sibutrin + TX, Diclofen + TX, Dichlorophene + TX, Endotal + TX, Fetin + TX, Disinfectant Lime + TX, Nabam + TX, Quinoclamine + TX, Quinonamide + TX, Simazine + TX, Triphenyltin Acetate + TX, Triphenyltin Hydroxide + TX, Clufomate + TX, Piperazine + TX, Thiophanate + TX, Chloralose + TX, Fenthion + TX, Pyridine-4-amine + TX, Strychnin + TX, 1-H-Pyridine-2-Thion + TX, 4-(Quinoxaline-2-ylamino)benzenesulfonamide + TX, 8-Hydroxyquinoline Sulfate + TX, Bronopol + TX, Copper Hydroxide + TX, Cresol + TX, Dipyrithione + TX, Doditin + TX, Phenaminosulf + TX, Formaldehyde + TX, Hydralgafen + TX, Kasugamycin + TX, Kasugamycin Hydrochloride Hydrate + TX, Nickel Bis(dimethyldithiocarbamate) + TX, Nitrapyrine + TX, Octylinone + TX, Oxolinic Acid + TX, Oxotetracycline + TX, Hydroxyquinoline Potassium Sulfate + TX, Probenazole + TX, Streptomycin + TX, Streptomycin Sesquisulfate + TX, Tecrophthalam + TX, Thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha farcifera 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 GV+TX, Dacnusa sibirica)+TX, 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 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, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema genus (Steinernema) spp.)+TX, Trichogramma spp.+TX, Typhlodromus occidentalis+TX, Verticillium lecanii+TX, Aphorate+TX, Bisadily+TX, Busulfan+TX, Dimatif+TX, Hemel+TX, Hempa+TX, Metepa+TX, Methiotepa+TX, Methyl aphorate+TX, Morzide+TX, Penfluron+TX,Tepa+TX, Thiohempa+TX, Thiotepa+TX, Tretamine+TX, Uredepa+TX, (E)-Deca-5-en-1-ylacetate and (E)-Deca-5-en-1-ol+TX, (E)-Trideca-4-en-1-ylacetate+TX, (E)-6-methylhepta-2-en-4-ol+TX, (E,Z)-Tetradeca-4,10-dien-1-ylacetate+TX, (Z)-Dodeca-7-en-1-ylacetate+TX, (Z)-Hexadeca-11-enal+TX, (Z)-Hexadeca-11-en-1-ylacetate+TX, (Z) -Hexadeca-13-en-11-in-1-ylacetate+TX, (Z)-Icosa-13-en-10-one+TX, (Z)-Tetradeca-7-en-1-al+TX, (Z)-Tetradeca-9-en-1-ol+TX, (Z)-Tetradeca-9-en-1-ylacetate+TX, (7E,9Z)-Dodeca-7,9-diene-1-ylacetate+TX, (9Z,11E)-Tetradeca-9,11-diene-1-ylacetate+TX, (9Z,12E)-Tetradeca-9,12-diene-1-ylacetate+TX, 14-Methyloctadeca-1 -En+TX, 4-methylnonan-5-ol and 4-methylnonan-5-one+TX, α-multistriatin+TX, Brevicomin+TX, Kodrelle+TX, Kodremon+TX, Querelle+TX, Disperla+TX, Dodeca-8-en-1-ylacetate+TX, Dodeca-9-en-1-ylacetate+TX, Dodeca-8+TX, 10-dien-1-ylacetate+TX, Dominicala+TX, Ethyl 4-methyloctanoate+TX, Eugenol+TX, Frontalin+TX, Grandlua+TX, Grandlua I+TX, Grandlua II+TX, Grandlua III+TX, Grandlua IV+TX, Hexalua+TX, Ipsdienol+TX, Ipsenol+TX, Japonilua+TX, Lineatin+TX, Littleua+TX, Lupulua+TX, Medruua+TX, Megatomoic acid+TX, Methyl eugenol+TX, Muscarua+TX, Octadeca-2,13-diene-1-ylacetate+TX, Octadeca-3,13-diene-1-ylacetate+TX, Orfuralua+TX, Orictalua+TX, Ostramon+TX, Siglua+TX, Solzidine+TX, Sulcatol+TX,Tetradeca-11-en-1-yl acetate + TX, Trimedolua + TX, Trimedolua A + TX, Trimedolua B1 + TX, Trimedolua B2 + TX, Trimedolua C + TX, Trunk-col + TX, 2-(octylthio)ethanol + TX, Butapyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Diethyltoluamide + TX, Dimethyl carbate + TX, Dimethyl phthalate + TX, Ethyl hexanediol + TX, Hexam Do+TX, Methquine-butyl+TX, Methylneodecanamide+TX, Oxamate+TX, Picalidine+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-Dichlorovinyl 2-ethylsulfinylethylmethylphosphate+TX, 2-(1,3-Dithiolan-2-yl)phenyl Nyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethylthiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyldiethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-inyl)aminophenylmethylcarbamate + TX, 2-thiocyanate ethyl laurate + TX, 3-bromo-1-chloro Prop-1-ene + TX, 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate + TX, 4-methyl(prop-2-inyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohexa-1-enyldimethylcarbamate + TX, acetylone + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixicarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasin + TX, atidathion + TX, azamethiphos + TX,Bacillus thuringiensis δ-endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, sodium borate + TX, bromfenbinphos + TX, bromo-DDT + TX, bufencarb + TX, butacarb + TX, butathiophos + TX, butonate + TX, calcium arsenate + TX, calcium cyanide + TX, carbon disulfide + TX, carbon tetrachloride + TX, cartap hydrochloride + TX, sebadin + TX, Chlorbicylene + TX, Chlordan + TX, Chlordecone + TX, Chloroform + TX, Chloropicrin + TX, Chlorphoxime + TX, Chlorprazophos + TX, Cis-resmethrin + TX, Cysmethrin + TX, Crocitrin + TX, Copper acetoarsenite + TX, Copper arsenate + TX, Copper oleate + TX, Cumithoate + TX, Cryolite + TX, CS708 + TX, Cyanophenphos + TX, Cyanophos + TX, Ciclethrin + TX, Cithioate + TX, d-Tetramethrin + TX, DAEP + TX, Dazomet + TX, De Carbofuran + TX, Diamidaphos + TX, Dikapton + TX, Dichlorophenthion + TX, Dicresyl + TX, Dicyclanil + TX, Dieldrin + TX, Diethyl 5-methylpyrazole-3-yl phosphate + TX, Dirol + TX, Dimefluthrin + TX, Dimethane + TX, Dimethrin + TX, Dimethylvinphos + TX, Dimethilane + TX, Dinoprop + TX, Dinosam + TX, Dinoseb + TX, Diofenolan + TX, Dioxabenzophos + TX, Diticlophos + TX, DSP + TX, Ecdysterone + TX, EI 1642+TX, EMPC+TX, EPBP+TX, Etaphos+TX, Ethiofencarb+TX, Ethyl Formate+TX, Ethylenedibromide+TX, Dichloroethane+TX, Ethylene Oxide+TX, EXD+TX, Fenchlorphos+TX, Phenetacarb+TX, Fenitrothion+TX, Phenoxacrim+TX, Fenpyritrin+TX, Fensulfothione+TX, Fenthion-ethyl+TX, Flucoflon+TX, Fosmethilane+TX, Fosspire+TX, Fosthitane+TX, Frathiocarb+TX, Frethrin+TX, Guazatin+TX, Guazatin Acetate+TX , sodium tetrathiocarbonate + TX, halfenprox + TX, HCH + TX, HEOD + TX, heptachlor + TX, heterophos + TX, HHDN + TX, hydrogen cyanide + TX, hikincarb + TX, IPSP + TX, isazofos + TX, isobenzan + TX, isodrine + TX, isofenphos + TX, isolane + TX, isoprothiolane + TX, isoxathion + TX, larval hormone I + TX, larval hormone II + TX, larval hormone III + TX, kerebane + TX, quinoprene + TX, lead arsenate + TX, leptophos + TX, lilimphos + TX, lithidathion + TX,m-Cumenylmethylcarbamate + TX, Magnesium phosphide + TX, Magidox + TX, Mecarfone + TX, Menazone + TX, Mercurous chloride + TX, Mesulfenphos + TX, Metam + TX, Metam-potassium + TX, Metam-sodium + TX, Methanesulfonyl fluoride + TX, Metochlortophos + TX, Methoprene + TX, Methotrin + TX, Methoxychloride + TX, Methylisothiocyanate + TX, Methylchloroform + TX, Methylene chloride + TX, Methoxadiazone + TX, Milex + TX, Naphthalophos + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nico Tin sulfate + TX, Nichiazine + TX, Nornicotine + TX, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidine-4-yl phosphorothioate + TX, O,O,O',O'-tetrapropyldithiopyrophosphate + TX, Oleic acid + TX, Para-dichlorobenzene + TX, Parathion-methyl + TX, Pentachlorophenol + TX, Pentachlorophenyl laurate + TX, pH 60-38+TX, Fenkapton+TX, Fosnichlor+TX, Phosphine+TX, Foxime-methyl+TX, Pyrimethophos+TX, Polychlorodicyclopentadiene isomer+TX, Potassium arsenite+TX, Potassium thiocyanate+TX, Precosen I+TX, Precosen II+TX, Precosen III+TX, Pyrimidophos+TX, Profluthrin+TX, Promecarb+TX, Prothiophos+TX, Pyrazofos+TX, Pyrethmetrin+TX, Cassia+TX, Quinalphos-methyl+TX, Quinothion+TX, Lafuxanide + TX, Resmethrin + TX, Rotenone + TX, Cadetrin + TX, Lianya + TX, Lianodine + TX, Sabajira + TX, Shuradan + TX, Cebuphos + TX, SI-0009 + TX, Thiapronil + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium hexafluorosilicate + TX, Sodium pentachlorophenoxide + TX, Sodium selenite + TX, Sodium thiocyanate + TX, Sulcoflon + TX, Sulcoflon-sodium + TX,Sulfurylfluoride + TX, Sulprophos + TX, Tar oil + TX, Thionadin + TX, TDE + TX, Tebupyrimphos + TX, Temephos + TX, Terarethrin + TX, Tetrachloroethane + TX, Cyclophos + TX, Thiocyclam + TX, Thiocyclam hydrogen oxalate + TX, Thionadin + TX, Thiosultap + TX, Thiosultap-sodium + TX, Tralomethrin + TX, Transpermethrin + TX, Trizamate + TX, Trichlormetaphos-3 + TX, Trichloronat + TX, Trimetacarb + TX, Tolprocarb + TX, Triclopyricarb + TX, Triprene + TX, Veratridine + TX, Veratrin + TX, XMC + TX, Zetamethrin + TX, Zinc phosphide + TX, Zolaprophos + TX, Meperfluthrin + TX, Tetramethyl Fluthrin + TX, Bis(tributyltin) oxide + TX, Bromoacetamide + TX, Ferric phosphate + TX, Nicrossamide-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-thiadiadinane-3-ylacetic acid + TX, 6-Isopentenylaminopurine + TX, Anisifurupurine + TX, Bencrotiaz + TX, Cytokinin + TX, DCIP + TX, Furfural + TX, Isamidophos + TX, Kinetin + TX, Mulberry dark spot fungus (Myrothecium) Verrucaria composition + TX, tetrachlorothiophene + TX, xylenol + TX, zeatin + TX, potassium ethylxanthogenicate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, Japanese knotweed (Reynoutria sachalinensis) extract + TX, α-chlorohydrin + TX, ant + TX, barium carbonate + TX, bisthiosemi + TX, brodifacum + TX, bromadiolon + TX, bromethalin + TX, chlorofacinone + TX, cholecalciferol + TX, coumafluryl + TX, coumatetralyl + TX, crimidine + TX, diphenacum + TX, difethiaron + TX, difacinone + TX,Ergocalciferol + TX, fulocumafen + TX, fluoroacetamide + TX, flupropazine + TX, flupropazine hydrochloride + TX, norbolmid + TX, fosacetim + TX, phosphorus + TX, pidocroline + TX, pyrinulone + TX, siriloside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, farnesol and nerolidol + TX, berbutin + TX, MGK 264+TX, piperonyl butoxide+TX, piprotal+TX, propyl isomer+TX, S421+TX, sesamex+TX, sesasmorin+TX, sulfoxide+TX, anthraquinone+TX, copper naphthenate+TX, copper oxychloride+TX, dicyclopentadiene+TX, thyram+TX, zinc naphthenate+TX, ziram+TX, imanin+TX, ribavirin+TX, chloroinconazide+TX, mercury(II) oxide+TX, thiophanate-methyl+TX, azaconazole+TX, vitertanol+TX, bromconazole+TX, cyproconazole+TX, difenoconazole+TX, diniconazole+TX, Epoxyconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafole + TX, flametopyr + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, mycrobutanil + TX, paclobutrazol + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrisoxazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimephon + TX, Triadimenol + TX, Triflumizole + TX, Triticonazole + TX, Ancimidor + TX, Fenalimol + TX, Nualimol + TX, Bupirimate + TX, Dimethirimol + TX, Ethyrimol + TX, Dodemorph + TX, Fenpropidine + TX, Fenpropimorph + TX, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fludioxonil + TX, Benalaxil + TX, Flalaxil + TX, Metalaxil + TX, R-Metalaxil + TX, O Fress + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazole + TX, Clozolinate + TX, Diclozolin + TX, Microzolin + TX, Procymidone + TX, Vinclozolin + TX, Boscalid + TX, Carboxyne + TX, Fenflam + TX, Flutolanil + TX, Mepronil + TX, Oxycarboxyne + TX, Penthiopyrad + TX, Tifluzamide + TX, Dozin + TX, Iminoctadine + TX, Azoxystrobin + TX, Dimoxystrobin + TX, Enestrobrin + T X, Phenaminestrobin+TX, Fluphenoxystrobin+TX, Fluoxastrobin+TX, Kresoxim-methyl+TX, Metominostrobin+TX, Trifloxystrobin+TX, Oryzastrobin+TX, Picoxystrobin+TX, Pyraclostrobin+TX, Pyramethostrobin+TX, Pyramoxystrobin+TX, Ferubam+TX, Mancozeb+TX, Maneb+TX, Methylam+TX, Propineb+TX, Zineb+TX, Captahol+TX, Captan+TX, Fluorimide+TX, Holpet+TX, Trilfluanide +TX, Bordeaux mixture +TX, copper oxide +TX, mankapper +TX, copper oxin +TX, nitrotal-isopropyl +TX, edifenphos +TX, iprobenphos +TX, phosdiphen +TX, turcophos-methyl +TX, anilazine +TX, benthiavalicarb +TX, blastosidine-S +TX, chloroneb +TX, chlorothalonil +TX, cyflufenaamide +TX, cymoxanil +TX, diclosimene +TX, diclomazine +TX, dichloran +TX, diethofencarb +TX, dimethomorph +TX, flumorph +TX, dithianone +TX,Etaboxam + TX, Etridiazole + TX, Famoxadone + TX, Fenamidom + TX, Phenoxanil + TX, Felimzon + TX, Fluazinam + TX, Flumethylsulfolim + TX, Fluopicolide + TX, Fluoxythioconazole + TX, Flusulfamide + TX, Fluxapiroxad + TX, Fenhexamide + TX, Fosetyl-aluminum + TX, Himexazole + TX, Iprovalicarb + TX, Cyazofamide + TX, Metasulfocarb + TX, Metraphenone + TX, Pencyclon + TX, Phthalide + TX, Polio Xin+TX, Propamocarb+TX, Pyribencarb+TX, Proquinazide+TX, Pyrroquilon+TX, Pyriophenone+TX, Quinoxifen+TX, Quintozene+TX, Thiazinyl+TX, Triazoxide+TX, Tricyclazole+TX, Triforine+TX, Validamycin+TX, Valifenarate+TX, Zoxamide+TX, Mandipropamide+TX, Isopyrazam+TX, Sedaxane+TX, Benzovindiflupir+TX, Pidiflumetofen+TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3' ,4',5'-trifluorobiphenyl-2-yl)amide + TX, isoflucipram + TX, isothianil + TX, dipimethitron + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazol-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-carbonitrile + TX, (R)-3-(difluoro (Methyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, Fluindapyr + TX, Cumethoxystrobin (diaxiangjunzhi) + TX,Rubenmixianan + TX, Diclobentiazox + TX, Mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinoline-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, Oxathiapiproline + TX, t-butyl N-[6-[[[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl] Rubamate + TX, Pyraziflumid + TX, Impilfluxam + TX, Turolprocarb + TX, Mefentrifluconazole + TX, Ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX, N'-[4-(4,5-dichlorothiazole-2-yl)oxy-2,5-dimethylphenyl ]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole-4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]methanesulfonic acid + TX, buta-3-inyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimeth [Difluorophenyl)triazole-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazole-5-one + TX,1-Methyl-4-[3-Methyl-2-[[2-Methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazole-5-one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethylpenta-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, methallylpicoxamide + TX, tebufloxin + TX, ipuprphenoquine + TX, Quinofumeline + TX, isofetamide + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (may be prepared by the method described in International Publication No. 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-propa-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (International Publication No. 202 Methyl N-[[4-[1-(4-cyclopropyl-2,6-difluorophenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate + TX (may be prepared by the method described in International Publication No. 0 / 056090), Methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate + TX (may be prepared by the method described in International Publication No. 2020 / 097012), Methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate + TX (may be prepared by the method described in International Publication No. 0 / 056090). (Can be prepared by the method described in International Publication No. 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide + TX (Can be prepared by the method described in International Publication No. 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl Ropyrus-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide+TX (may be prepared by the method described in International Publication No. 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide+TX (may be prepared by the method described in International Publication No. 2020 / 109391), N-[2-[2,4-Dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, Benzothiostrobin + TX, Phenamacryl + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram + TX, Phenoxadiazam + TX, Fluthianil + TX, Fluopimomide + TX, Pyrapropoin + TX, Picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethicone (Lu-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-Biphenyl]-4-yl]-5-pyrimidine methanol + TX, fluoxapiproline + TX, enoxastrobin + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]prop-2-enoate + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazole-2-yl)phenoxy]prop-2-enoate + TX, methyl(Z)-2-[5-(3-yl] Sopropylpyrazole-1-yl)-2-methylphenoxy]-3-methoxypropa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]propa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]propa-2-enoate + TX (These compounds are from International Publication No. 2020 / 079111) (These compounds may be prepared by the method described in International Publication No. 2020 / 193387), methyl(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropa-2-enoate + TX, methyl(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxypropa-2-enoate + TX (These compounds may be prepared by the method described in International Publication No. 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydro Xy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-Triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Trinexapac + TX, Acromoxystrobin + TX, Zhongshengmycin + TX, Thiodiazole copper + TX, Zinc thiazole + TX, Amectotractin + TX, Iprodione + TX, Seboctylamine + TX; N-Octyl-N'-[2-(octylamino)ethyl]ethane-1,2-dia Min + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl N'-N-methylformamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine + TX (These compounds can be prepared by the method described in International Publication No. 2015 / 155075); N '-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (These compounds can be prepared by the method described in International Publication No. 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoro [(1R)- methyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (These compounds can be prepared by the method described in International Publication No. 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)- 1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide+TX, N-[(1S)1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquino Phosphorus-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-Dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoroquinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoroquinoline-3-carboxamide + TX (These compounds can be prepared by the method described in International Publication No. 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,6-trifluoro-3,3-dimethylisoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridine-3- Isoquinoline (Iyl) + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridine-3-yl)isoquinoline + TX, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (These compounds were prepared by the method described in International Publication No. 2017 / 025510) (These compounds may be prepared by the methods described in International Publication No. 2016 / 156085); 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4-difluoro-3,3-dimethylisoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazole-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazole-1-yl)-3,3-dimethylisoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (These compounds may be prepared by the methods described in International Publication No. 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl] [phenyl]methyl]propanamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- Xadiazole-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2 ,4-Oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine + TX. The compounds in this paragraph can be prepared by the methods described in International Publication No. 2017 / 055473, International Publication No. 2017 / 055469, International Publication No. 2017 / 093348 and International Publication No. 2017 / 118689;2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol + TX (This compound may be prepared by the method described in International Publication No. 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol + TX (This compound may be prepared by the method described in International Publication No. 2017 / 029179); 3 -[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitriel + TX (This compound may be prepared by the method described in International Publication No. 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitriel + TX (This compound may be prepared by the method described in International Publication No. 2016 / 156290); (4-phenoxyph (Ethyl)methyl 2-amino-6-methylpyridine-3-carboxylate + TX (This compound may be prepared by the method described in International Publication No. 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron + TX (This compound may be prepared by the method described in International Publication No. 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benz N-carbothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX (this compound can be prepared by the method described in International Publication No. 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX;N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine + TX (This compound may be prepared by the method described in International Publication No. 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX (This compound may be prepared by the method described in International Publication No. 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl (Tyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX (These compounds can be prepared by the method described in International Publication No. 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX (This compound can be prepared by the method described in International Publication No. 2018 / 06 It can be prepared by the method described in publication 5414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared by the method described in International Publication 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-( Bioactive substances selected from ()(1,2,4-oxadiazole-3-yl)benzamide+TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide+TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide+TX (these compounds may be prepared by the method described in International Publication No. 2018 / 202428); Microorganisms including the following: Acinetobacter lwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia (Alternaria cassia)+TX, Alternaria destruens (Smolder®)+TX, Ampelomyces quisqualis (AQ10®)+TX, Aspergillus flavus AF36 (AF36®)+TX, Aspergillus flavus NRRL 21882 (Aflaguard®)+TX, Aspergillus spp.)+TX, Aureobasidium pullulans+TX, Azospirillum+TX, (MicroAZ(registered trademark)+TX, TAZO B(registered trademark))+TX, Azotobacter+TX, Azotobacter chroocuccum (Azotomeal(registered trademark))+TX, Azotobacter cysts (Bionatural Blooming Blossoms(registered trademark))+TX, Bacillus amyloliquefaciens+TX, Bacillus cereus+TX, Bacillus chitinosporus strain CM-1+TX, Bacillus Bacillus chitinosporus strain AQ746+TX, Bacillus licheniformis strain HB-2 (Biostart®, Rhizoboost®)+TX, Bacillus licheniformis strain 3086 (EcoGuard® +TX, Green Releaf®)+TX, Bacillus circulans+TX, Bacillus firmus (BioSafe® +TX, BioNem-WP® +TX, VOTiVO®)+TX, Bacillus firmus strain I-1582+TX, Bacillus macerans+TX, Bacillus marismortzii (Bacillus marismortui)+TX, Bacillus megaterium+TX, Bacillus mycoides strain AQ726+TX, Bacillus papillae (Milky Spore Powder®)+TX, Bacillus pumilus spp.)+TX, Bacillus pumilus strain GB34 (Yield Shield®)+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain QST 2808 (Sonata® +TX, Ballad Plus®)+TX, Bacillus spahericus (VectoLex®)+TX, Bacillus spp.+TX, Bacillus spp. strain AQ175+TX, Bacillus spp. strain AQ177+TX, Bacillus spp. strain AQ178+TX, Bacillus Bacillus subtilis strain QST 713 (CEASE(R)+TX, Serenade(R)+TX, Rhapsody(R))+TX, Bacillus subtilis strain QST 714(JAZZ(R))+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciens.amyloliquefaciens) strain FZB24 (Taegro(registered trademark)+TX, Rhizopro(registered trademark))+TX, Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensis Cry1Ab+TX, Bacillus thuringiensis aizawai GC 91 (Agree(registered trademark))+TX, Bacillus thuringiensis israelensis (BMP123(registered trademark)+TX, Aquabac(registered trademark)+TX, VectoBac(registered trademark))+TX, Bacillus thuringiensis krustaki (Bacillus thuringiensis Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bondide® + TX, Scutella WP® + TX, Turilav WP® + TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis Bacillus thuringiensis) strain AQ52+TX, Bacillus thuringiensis var. aizawai (XenTari(registered trademark)+TX, DiPel(registered trademark))+TX, Bacteria spp.)(GROWMEND(registered trademark)+TX, GROWSWEET(registered trademark)+TX, Shootup(registered trademark))+TX, Clavipacter michiganensis bacteriophage (AgriPhage(registered trademark))+TX, Bakflor(registered trademark)+TX, Beauveria bassiana (Beaugenic(registered trademark)+TX, Brocaril WP(registered trademark))+TX, Beauveria bassiana GHA (Mycotrol ES(registered trademark)+TX, Mycotrol O(registered trademark)+TX, BotaniGuard(registered trademark))+TX, Beauveria brongniartii (Engerlingspilz(registered trademark)+TX, Schweizer Beauveria(registered trademark)+TX, Melocont(registered trademark))+TX, Beauveria genus (Beauveria spp.)+TX, Botrytis cineria+TX, soybean rhizobia (Bradyrhizobium japonicum) (TerraMax®)+TX, Brevibacillus brevis+TX, Bacillus thuringiensis tenebrionis (Novodor®)+TX, BtBooster+TX, Burkholderia cepacia (Deny®)+TX, Intercept®+TX, . Blue Circle (registered trademark) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide (registered trademark)) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida olephylla (Candida Candida oleophila) strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima+TX, Candida reukaufii+TX, Candida saitoana (Bio-Coat®+TX, Biocure®)+TX, Candida sake+TX, Candida spp.)+TX, Candida tenius+TX, Cedecea dravisae+TX, Cellulomonas flavigena+TX, Chaetomium cochliodes (Nova-Cide®)+TX, Chaetomium globosum (Nova-Cide®)+TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®)+TX, Cladosporium cladosporioides+TX, Cladosporium oxysporum+TX, Cladosporium chlorocephalum chlorocephalum)+TX, Cladosporium spp.+TX, Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine®)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG®)+TX, Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS(registered trademark))+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex(registered trademark))+TX, Cupriavidus campinensis+TX, Cydia pomonella granulovirus (CYD-X(registered trademark))+TX, Cydia pomonella granulovirus (Cydia Pomonella granulovirus (Madex® + TX, Madex Plus® + TX, Madex Max / Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophthora virulenta (Vektor®) + TX, Epicoccum nigram nigrum)+TX, Epicoccum purpurascens+TX, Epicoccum spp.)+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean® / Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®+TX, Prestop®)+TX, Gliocladium roseum roseum)+TX, Gliocladium spp. (SoilGard®)+TX, Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedra virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedra virus (Gemstar®)+TX, Isoflavone-formononetin (Myconate®)+TX, Kloeckera apiculata+TX, Kloeckera spp.)+TX, Lagenidium giganteum (Laginex®)+TX, Greenhouse whitefly (Lecanicillium longisporum) (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, Gypsy moth (Lymantria dispar) nuclear polyhedron virus (Disparvirus®)+TX, Marinococcus halophilus+TX, Meira geulakonigii+TX, Metalhizium anisopliae (Met52®)+TX, Metalhizium anisopliae (Destruxin WP(registered trademark))+TX, Metschnikowia fruticola (Shemer(registered trademark))+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot(registered trademark))+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus 620 (Muscudor(registered trademark))+TX, Muscodor roseus strain A3-5+TX, Mycorrhizae spp. (AMykor(registered trademark))+TX, . Root Maximizer (registered trademark) + TX, Mulberry dark spot disease fungus (Myrothecium verrucaria) strain AARC-0255 (DiTera (registered trademark)) + TX, BROS PLUS (registered trademark) + TX, Ophiostoma piliferum strain D97 (Sylvanex (registered trademark)) + TX, Paecilomyces farinosus + TX, Paecilomyces fumosoroseus (PFR-97 (registered trademark) + TX, PreFeRal (registered trademark)) + TX, Paecilomyces linacinus (Biostat WP (registered trademark)) + TX, Paecilomyces lilacinus strain 251 (MeloCon WG(registered trademark))+TX, Paenibacillus polymyxa+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea spp.+TX, Pasteuria spp. (Econem(registered trademark))+TX, Pasteuria nishizawae+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart(registered trademark)+TX, TagTeam(registered trademark))+TX, Penicillium brevicompactum+TX, Penicillium phlequentans (Penicillium Penicillium frequentans) + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.)+TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop®)+TX, Phosphollytic bacteria (Phosphomeal®)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX, Pichia guilermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites+TX, Pseudomonas Pseudomonas aeruginosa) + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp.)+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, fluorescent bacterium (Pseudomons fluorescens) (Zequanox®)+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®)+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior®)+TX, Pythium paroecandrum+TX, Pythium oligandrum (Pythium oligandrum)(Polygandron(registered trademark)+TX, Polyversum(registered trademark))+TX, Pythium periplocum+TX, Rhanella aquatilis+TX, Rhanella spp.+TX, Rhizobia (Dormal(registered trademark)+TX, Vault(registered trademark))+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX, Rhodotorula spp.)+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor+TX, Sclerotinia minor (SARRITOR®)+TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX, Spodoptera exigua) Nuclear Polyhedron Disease Virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp.)+TX, Sordaria fimicola+TX, Spodoptera littoralis nuclear multinuclear virus (Littovir®)+TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces ahygroscopicus+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces glyceoplanus (Streptomyces *griseoplanus* + TX, *Streptomyces griseoviridis* (Mycostop®) + TX, *Streptomyces lydicus* (Actinovate®) + TX, *Streptomyces lydicus* WYEC-108 (ActinoGrow®) + TX, *Streptomyces violaceus* + TX, *Tilletiopsis minor* + TX, *Tilletiopsis spp.* + TX, *Trichoderma asperellum* (T34 Biocontrol®) + TX, *Trichoderma gamsii* (Tenet®) + TX, . Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii (Trichoderma koningii)+TX, Trichoderma spp. LC 52 (Sentinel(registered trademark))+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum (Binab T(registered trademark))+TX, Trichoderma taxi+TX, Trichoderma virens+TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard(registered trademark))+TX, Trichoderma viride+TX, Trichoderma viride (Trichoderma viride) strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon genus (Trichosporon spp.) + TX, Trichothecium genus (Trichothecium spp.))+TX, Trichothecium roseum+TX, Typhula phacorrhiza strain 94670+TX, Typhula phacorrhiza strain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii (Botry-Zen®)+TX, Ustilago maydis+TX, various bacteria and auxiliary micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium+TX, Verticillium lecanii * *lecanii* (Mycotal® + TX, Vertalec®) + TX, *Vip3Aa20* (VIPtera®) + TX, *Virgibaclillus marismortui* + TX, *Xanthomonas campestris pv. Poae* (Camperico®) + TX, *Xenorhabdfus bovienii* + TX, *Xenorhabdus nematophilus*; Plant extracts including the following: Pine oil (Retenol®) + TX, Azadirachtin (Plasma Neem Oil® + TX, AzaGuard® + TX, MeemAzal® + TX, Molt-X®) + TX, Botanical insect growth regulators (Neemazad® + TX, Neemix®) + TX, Rapeseed oil (Lilly Miller Vegol®) + TX, American antlion (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, Neem oil extract (Trilogy®) + TX, Lamiaceae plant essential oil (Botania®) + TX, Clove, rosemary, peppermint and thyme oil extracts (Garden insect Killer® + TX, Glycine Betaine (Greenstim®) + TX, Garlic + TX, Lemongrass Oil (GreenMatch®) + TX, Neem Oil + TX, Catnip Oil (Nepeta cataria) + TX, Catnip Oil (Nepeta catarina) + TX, Nicotine + TX, Oregano Oil (MossBuster®) + TX, Pedaliaceae Oil (Nematon®) + TX, Pyrethrum + TX, Soap Tree (Quillaja saponaria) (NemaQ®) + TX, Japanese Knotweed (Reynoutria sachalinensis) (Regalia® + TX, Sakalia®) + TX, Rotenone (Eco Roten®) + TX, Rutaceae Extract (Soleo®) + TX, Soybean Oil (Ortho ecosense(registered trademark))+TX, tea tree oil (Timorex Gold(registered trademark))+TX, thyme oil+TX, AGNIQUE(registered trademark) MMF+TX, BugOil(registered trademark)+TX, mixture of rosemary, sesame, peppermint, thyme and cinnamon extracts (EF)300 (registered trademark)) + TX, a mixture of clove, rosemary, and peppermint extracts; EF 400 (registered trademark)) + TX, a mixture of clove, peppermint, garlic oil, and mint; Soil Shot (registered trademark)) + TX, kaolin; Screen (registered trademark) + TX, brown algae storage glucan; Laminarin (registered trademark); Pheromones including the following: Blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Codling Moth pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Grape Berry Moth pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, Leafroller moth pheromone (3M MEC-LR Sprayable Pheromone®) + TX, Muscamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone®) + TX, Peachtree moth pheromone (Selaginellaidae) Borer pheromone (Isomate-P®) + TX, Tomato pinworm pheromone (3M Sprayable pheromone®) + TX, Entostat powder (extract from palm trees) (Exosex CM®) + TX, (3E,8Z,11Z)-3,8,11-tetradecatrieninyl acetate + TX, (7Z,11Z,13E)-7,11,13-hexadecatrienal + TX, (E,Z)-7,9-dodecadiene-1-yl acetate + TX, 2-methyl-1-butanol + TX, calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, Lavandulyl senecioate + TX; Macrovials containing the following: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus californicus) (Amblyline(registered trademark)+TX, Spical(registered trademark))+TX, Amblyseius cucumeris (Thripex(registered trademark)+TX, Bugline cucumeris(registered trademark))+TX, Amblyseius fallacis (Fallacis(registered trademark))+TX, Amblyseius swirskii (Bugline swirskii(registered trademark)+TX, Swirskii-Mite(registered trademark))+TX, Amblyseius womersleyi (WomerMite(registered trademark))+TX, Amitus hesperidum+TX, Anagrus atomus+TX, Anagyrus fussiventris Anagyrus fusciventris) + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococcus (Anagyruspseudococci) (Citripar(registered trademark))+TX, Anicetus benefices+TX, Anisopteromalus calandrae+TX, Anthocoris nemoralis (Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark)+TX, Aphiline(registered trademark))+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphidius matricariae)(Aphipar-M(registered trademark))+TX, Aphidoletes aphidimyza(Aphidend(registered trademark))+TX, Aphidoletes aphidimyza(Aphidoline(registered trademark))+TX, Aphytis lingnanensis+TX, Aphytis melinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria(Staphyline(registered trademark))+TX, Bombus spp.+TX, European bumblebee (Bombus terrestris)(Natupol Beehive (registered trademark) + TX, Bombus terrestris (Beeline (registered trademark) + TX, Tripol (registered trademark)) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperlacarnea) (Chrysoline(registered trademark))+TX, Yamato lacewing (Chrysoperla carnea) (Chrysopa(registered trademark))+TX, Chrysoperla rufilabris+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus+TX, Citrostichus phyllocnistoides+TX, Closterocerus chamaeleon+TX, Closterocerus spp.+TX, Coccidoxenoides perminutus (Planopar(registered trademark))+TX, Coccophagus cowperi)+TX, Coccophagus lycimnia+TX, Cotesia flavipes+TX, Cotesia plutellae+TX, Cryptolaemus montrouzieri (Cryptobug®+TX, Cryptoline®)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica+TX, Dacnusa sibirica (Minusa®)+TX, Diglyphus isaea (Diminex®)+TX, Delphastus catarinae catalinae)(Delphastus(registered trademark))+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata+TX, Diaparsis jucundajucunda)+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaea+TX, Diglyphus isaea (Miglyphus(registered trademark)+TX, Digline(registered trademark))+TX, Dacnusa sibirica (DacDigline(registered trademark)+TX, Minex(registered trademark))+TX, Diversinervus spp.+TX, Encarsia citrina+TX, Encarsia formosa (Encarsia max(registered trademark)+TX, Encarline(registered trademark)+TX, En-Strip(registered trademark))+TX, Eretmocerus eremicus)(Enermix(registered trademark))+TX, Encarsia guadeloupae+TX, Encarsia haitiensis+TX, Ebisyrphus balteatus(Syrphidend(registered trademark))+TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX, Eretmocerus eremicus(Ercal(registered trademark)+TX, Eretline e(registered trademark))+TX, Eretmocerus eremicus(Bemimix(registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus(Eretmocerus mundus) (Bemipar (registered trademark) + TX, Eretline m (registered trademark)) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisgaacarisuga)(Spidend(registered trademark))+TX, Feltiella acarisuga(Feltiline(registered trademark))+TX, Fopius arisanus+TX, Fopius ceratitivorus+TX, formononetin(Wirless Beehome(registered trademark))+TX, Franklinothrips vespiformis(Vespop(registered trademark))+TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis (HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield) HB(registered trademark)+TX, Nemaseek(registered trademark)+TX, Terranem-Nam(registered trademark)+TX, Terranem(registered trademark)+TX, Larvanem(registered trademark)+TX, B-Green(registered trademark)+TX, NemAttack(registered trademark)+TX, Nematop(registered trademark))+TX, Heterorhabditis megidis (Nemasys H(registered trademark)+TX, BioNem H(registered trademark)+TX, Exhibitline hm(registered trademark)+TX, Larvanem-M(registered trademark))+TX, Hippodamia convergens+TX, Hypoaspis aculeifer (Aculeifer-System(registered trademark)+TX, Entomite-A(registered trademark))+TX, Hypoaspis miles (Hypoline m(registered trademark)+TX, Entomite-M(registered trademark))+TX, Lbalia leucospoides+TX, Lecanoideus floccissimus+TX, Lemophagus errabundus+TX, Leptomastidea abnormis+TX, Leptomastix dactylopii (Leptopar(registered trademark))+TX, Leptomastix epona (Leptomastixepona)+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly(registered trademark))+TX, Lysiphlebus testaceipes+TX, Macrolophus caliginosus (Mirical-N(registered trademark)+TX, Macroline c(registered trademark)+TX, Mirical(registered trademark))+TX, Mesoseiulus longipes+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromus angratus angulatus) (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis tenuis)(NesidioBug(registered trademark)+TX, Nesibug(registered trademark))+TX, Ophyra aenescens(Biofly(registered trademark))+TX, Orius insidiosus(Thripor-I(registered trademark)+TX, Oriline i(registered trademark))+TX, Orius laevigatus(Thripor-L(registered trademark)+TX, Orilinel(registered trademark))+TX, Orius majusculus (Oriline m(registered trademark))+TX, Orius strigicollis (Thripor-S(registered trademark))+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita (Nemaslug(registered trademark))+TX, Phymastichus coffea+TX, Phytoseiulus macropilus+TX, Phytoseiulus persimilis (Spidex(registered trademark))+TX, Phytoline p(registered trademark))+TX, Podisus maculiventris (Podisus(registered trademark))+TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp.+TX, Rhyzobius lophantae lophanthae)+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenaeavenae)(Ervibank(registered trademark))+TX, Steinernema carpocapsae(Nematac C(registered trademark)+TX, Millenium(registered trademark)+TX, BioNem C(registered trademark)+TX, NemAttack(registered trademark)+TX, Nemastar(registered trademark)+TX, Capsanem(registered trademark))+TX, Steinernema feltiae(NemaShield(registered trademark)+TX, Nemasys F(registered trademark)+TX, BioNem F(registered trademark)+TX, Steinernema-System(registered trademark)+TX, NemAttack(registered trademark)+TX, Nemaplus(registered trademark)+TX, Exhibitline sf(registered trademark)+TX, Scia-rid(registered trademark)+TX, Entonem(registered trademark))+TX, Steinernema kraussei(Nemasys L(registered trademark)+TX, BioNem L(registered trademark)+TX, Exhibitline srb(registered trademark))+TX, Steinernema riobrave (BioVector(registered trademark)+TX, BioVektor(registered trademark))+TX, Steinernema scapterisci (Nematac S(registered trademark))+TX, Steinernema spp.+TX, Steinernematid spp. (Guardian Nematodes(registered trademark))+TX, Stethorus punctillum (Stethorus(registered trademark))+TX, Tamarixia radiate+TX, Tetrastichus setifer)+TX, Thripobius semiluteus+TX, Torymus sinensis+TX, Egg parasitic wasp (Trichogramma brassicae) (Tricholineb(registered trademark))+TX, egg parasitic wasp (Trichogramma brassicae) (Tricho-Strip(registered trademark))+TX, armyworm egg parasitoid wasp (Trichogramma evanescens)+TX, Trichogramma minutum+TX, corn borer egg parasitoid wasp (Trichogramma ostriniae)+TX, Trichogramma platneri+TX, Trichogramma pretiosum+TX, yellow-legged flat wasp (Xanthopimpla stemmator); Other biological products including: Abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct® + TX, Ni-HIBIT Gold CST®) + TX, Fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER®) + TX, Ferric phosphate (Ferramol®) + TX, Funnel Trap (Trapline y(registered trademark))+TX, Gallex(registered trademark)+TX, Grower's Secret(registered trademark)+TX, Homo-brassonolide+TX, Iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait(registered trademark))+TX, MCP hail trap (Trapline f(registered trademark))+TX, Microctonus hyperodae+TX, Mycoleptodiscus terrestris (Des-X(registered trademark))+TX, BioGain(registered trademark)+TX, Aminomite(registered trademark)+TX, Zenox(registered trademark)+TX, Pheromone trap (Thripline ams(registered trademark)) + TX, potassium bicarbonate (MilStop(registered trademark)) + TX, potassium salt of fatty acid (Sanova(registered trademark)) + TX, potassium silicate solution (Sil-Matrix(registered trademark)) + TX, potassium iodide + potassium thiocyanate (Enzicur(registered trademark)) + TX, SuffOil-X(registered trademark) + TX, spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper)Control(registered trademark))+TX, sticky traps (Trapline YF(registered trademark)+TX, Rebell Amarillo(registered trademark))+TX, and traps (Takitrapline y+b(registered trademark))+TX; (1) Antimicrobial agents selected from the following group: (1.1) Examples include: Bacteria: Bacillus mojavensis strain R3B (acceptance number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX from Certis USA LLC, a subsidiary of Mitsui & Co.; Bacillus pumilus, in particular strain BU F-33 with NRRL acceptance number 50185 (available as part of the CARTISSA® product from BASF, EPA registration number 71840-19) + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with NRRL acceptance number B21661, U.S. Patent No. 6,060,051) + TX; Bacillus subtilis Bacillus subtilis) strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA) +TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) +TX; Bacillus subtilis CX-9060 +TX from Certis USA LLC, a subsidiary of Mitsui & Co.; Bacillus sp., particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), acceptance number FERM A species of the genus Paenibacillus having BP-8234, U.S. Patent No. 7,094,592+TX; acceptance number NRRL B-50972 or acceptance number NRRL B-67129 (Paenibacillus sp.)) strains, International Publication No. 2016 / 154297+TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.)+TX; Pantoea agglomerans, in particular strain E325 (acceptance number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL® FD BIOPESTICIDE from Northwest Agri Products)+TX; Pseudomonas proradix from Sourcon Padena (e.g., PRORADIX®)+TX; and. (1.2) Examples include the following fungi: Aureobasidium pullulans, in particular spores of strain DSM14940, spores of strain DSM14941, or mixtures of spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae cerevisiae), particularly strains CNCM numbers 1-3936, 1-3937, 1-3938, or 1-3939 (disclosed in International Publication No. 2010 / 086790 from Lesaffre et Compagnie, FR) + TX; (2) Biological fungicides selected from the following groups: (2.1) Examples include the following bacteria: Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX; Agrobacterium radiobacter strain K1026 (e.g., NOGALL® from BASF SE) + TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) with acceptance number DSM 10271 + TX; Bacillus amyloliquefaciens, in particular strain D747 (acceptance number FERM Kumiai Chemical Industry Co., Ltd. possesses BP-8234.Available as Double Nickel (trademark), U.S. Patent No. 7,094,592 (+TX); Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL acceptance number B-50768, International Publication No. 2014 / 028521) (STARGUS (trademark) from Marrone Bio Innovations) (+TX); Bacillus amyloliquefaciens strain FZB42, acceptance number DSM 23117 (available as RHIZOVITAL (trademark) from ABiTEP, DE) (+TX); Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN (trademark) from University of Pretoria) (+TX); acceptance number ATCC Bacillus licheniformis, particularly strain SB3086, containing 55406, International Publication No. 2003 / 000051 (available from Novozymes as ECOGUARD® Biofungicide and GREEN RELEAF®) +TX +TX; Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) +TX; Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) +TX; Bacillus mojavensis from Certis USA LLC, a subsidiary of Mitsui & Co. Bacillus mycoides (mojavensis) strain R3B (acceptance number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX; acceptance number B-30890, isolate (Mitsui&Co.)Bacillus pumilus, in particular strain QST2808 (with acceptance number NRRL B-30087, described in U.S. Patent No. 6,245,551, available from Bayer CropScience LP, US as SONATA®) +TX; Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as Yield Shield®) +TX; Bacillus pumilus with NRRL acceptance number 50185, in particular strain BU F-33 (available as part of CARTISSA products from BASF, EPA registration number 71840-19) +TX; Bacillus Bacillus subtilis), particularly strain QST713 / AQ713 (with NRRL acceptance number B21661, listed in U.S. Patent No. 6,060,051, available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US) + TX; Bacillus subtilis Y1336 (registered in Taiwan as a biological fungicide and mycicide under registration numbers 4764, 5454, 5096 and 5277, available as BIOBAC® WP from Bion-Tech, Taiwan) + TX; Bacillus subtilis strain MBI 600 (with acceptance number NRRL B-50595, available as SUBTILEX from BASF SE), U.S. Patent No. 5,061,495 + TX; Bacillus subtilis strain GB03 (Bayer (Available from AG, DE as Kodiak®) + TX; Bacillus subtilis strain BU1814, (Available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA) + TX; Mitsui & Co.Bacillus subtilis CX-9060+TX from Certis USA LLC, a subsidiary of BASF; Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys)+TX; Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies, PORTENTO® from Idai Nature)+TX; Bacillus subtilis strain Y1336 (registered as a biological fungicide and mycicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277, available as BIOBAC® WP from Bion-Tech, Taiwan)+TX; Paenibacillus epiphyticus from BASF SE (International Publication No. 2016 / 020371)+TX; BASF Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371) + TX; Paenibacillus sp. with acceptance number NRRL B-50972 or acceptance number NRRL B-67129.) strain, International Publication No. 2016 / 154297+TX; Pseudomonas chlororaphis strain AFS009, International Publication No. 2017 / 019448, with acceptance number NRRL B-50897 (e.g., HOWLER® and ZIO® from AgBiome Innovations, US)+TX; Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON®, CERALL® and CEDRESS® by Bioagri and Koppert)+TX; fluorescent bacterium (Pseudomonas fluorescens) strain A506 (e.g., BLIGHTBAN® A506 by NuFarm)+TX; Pseudomonas proradix (e.g., Sourcon PRORADIX® from Padena + TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (acceptance number DSM 7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, cf. Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON® and ACTINOOVATE® from Novozymes) + TX; and. (2.2) Examples include the following fungi: Ampelomyces quisqualis, in particular strain AQ 10 (e.g., AQ 10® by IntrachemBio Italia) + TX; Ampelomyces quisqualis strain AQ10 (e.g., AQ 10® by IntrachemBio Italia) + TX with acceptance number CNCM 1-807; Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular budding spores of strain DSM14940 + TX; Aureobasidium pullulans Aureobasidium pullulans, particularly budding spores of strain DSM 14941 + TX; Aureobasidium pullulans, particularly a mixture of budding spores of strains DSM14940 and DSM 14941 (e.g., Botector® by bio-ferm, CH) + TX; Chaetomium cupreum (acceptance number CABI 353812) (e.g., BIOKUPRUM® by AgriLife) + TX; Chaetomium globosum (available as RIVADIOM® by Rivale) + TX; Cladosporium cladosporioides, strain H39, U.S. Patent Application Publication No. 2010 / 0291039 (Stichting Coniothyrium minitans, particularly strain CON / M / 91-8 (acceptance number DSM9660, e.g., Contans® registered trademark from Bayer CropScience Biologics GmbH) +TX;Cryptococcus flavescens, strain 3C (NRRL Y-50378), (B2.2.99) + TX; Dactylaria candida + TX; Dilophosphora alopecuri (available as TWIST FUNGUS®) + TX; Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® by Natural Plant Protection) + TX; Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulata) f. catenulate) strain J1446 (e.g., Prestop® by Lallemand) + TX; Gliocladium roseum (also known as Clonostachys rosea f. rosea), particularly strain 321U from Adjuvants Plus, strain ACM941 or strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australas Plant Pathol. 2007, 36:95-101) + TX;Conidia of Lecanicillium lecanii (formerly known as Verticillium lecanii) strain KV01 (e.g., Vertalec® by Koppert / Arysta) + TX; Metschnikowia fructicola, especially strain NRRL Y-30752, (B2.2.3) + TX; Microsphaeropsis ochracea + TX; Muscodor roseus, especially strain A3-5 (acceptance number NRRL 30548) + TX; Penicillium steckii from BASF SE (DSM) 27859, International Publication No. 2015 / 067800)+TX; Penicillium vermiculatum+TX; Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment)+TX; Pichia anomala; Strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX; Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., CA) + TX; Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives), strain LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF SE), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM from Lesaffre et Compagnie, FR No.1-3939 (International Publication No. 2010 / 086790) +TX; Simplicillium lanosoniveum +TX; Talaromyces flavus, strain V117b +TX; Trichoderma asperelloides JM41R (Acceptance No. NRRL B-50759) (TRICHO PLUS® from BASF SE) +TX; Trichoderma asperellum, especially strain kd (e.g., T-Gro from Andermatt Biocontrol) +TX; Trichoderma asperellum with Acceptance No. FERM P-16510, especially strain SKT-1 (e.g., Kumiai Chemical ECO-HOPE® from Industry, strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies SL,ES), or strain ICC 012+TX from Isagro;Trichoderma atroviride, particularly strain SC1 (with acceptance number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited) + TX; Trichoderma atroviride, strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX; Trichoderma atroviride, strain number V08 / 002387 + TX; Trichoderma atroviride Trichoderma atroviride), strain NMI number V08 / 002388+TX; Trichoderma atroviride, strain NMI number V08 / 002389+TX; Trichoderma atroviride, strain NMI number V08 / 002390+TX; Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Limited)+TX; Trichoderma atroviride, strain ATCC 20476 (IMI 206040)+TX; Trichoderma atroviride Trichoderma atroviride), strain T11 (IMI352941 / CECT20498) +TX; Trichoderma atroviride, strain SKT-1 (FERM P-16510), Japanese Patent Publication No. 11-253151 +TX; Trichoderma atroviride, strain SKT-2 (FERM P-16511), Japanese Patent Publication No. 11-253151 +TX; Trichoderma atroviride, strain SKT-3 (FERM P-17021), Japanese Patent Publication No. 11-253151 +TX;Trichoderma fertile (e.g., product TrichoPlus from BASF) + TX; Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., BioDerma by AGROBIOSOL DE MEXICO, SADE CV) + TX; Trichoderma gamsii (formerly T. viride), strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) + TX; Trichoderma harmatum + TX; Trichoderma harmatum with acceptance number ATCC 28012 Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (from Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim, US) + TX; Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) + TX; Trichoderma harzianum Trichoderma harzianum), strain TH35 (e.g., Root-Pro by Mycontrol) + TX; Trichoderma harzianum, strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab) + TX;Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX; Trichoderma stromaticum with acceptance number Ts3550 (e.g., Tricovab by CEPLAC, Brazil) + TX; Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US) + TX; Trichoderma virens strain G-41 (formerly known as Gliocladium virens) (acceptance number ATCC) 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + TX; Trichoderma viride, strain TV1 (e.g., Trianum-P by Koppert) + TX; Trichoderma viride, especially strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX; Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012) with acceptance number CABI CC IMI 392716 and acceptance number IMI A mixture of Trichoderma gamsii (formerly known as T. viride) strain ICC 080 containing 392151 (e.g., BIO-TAM® from Isagro USA, Inc. and BIODERMA® by Agrobiosol de Mexico, SAde CV) + TX;Ulocladium oudemansii strain U3 with acceptance number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® by BioWorks, Inc.) + TX; Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with acceptance number WCS850 deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) + TX; Verticillium chlamydosporium + TX; (3) A biological control agent selected from the following group that has the effect of improving plant growth and / or plant health: (3.1) Examples of bacteria include: Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX; Azospirillum lipoferum (e.g., VERTEX-IF® from TerraMax, Inc.) + TX; Azorhizobium caulinodans, especially strain ZB-SK-5 + TX; Azotobacter chroococcum, especially strain H23 + TX; Azotobacter vinelandii, especially strain ATCC 12837 + TX; Azotobacter vinelandii and Clostridium pasteurianum A mixture of pasteurianum (available as INVIGORATE® from Agrinos) + TX; Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX; Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542, International Publication No. 2017 / 205258) + TX; Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX; Bacillus amyloliquefaciens, in particular strain IN937a + TX; Bacillus amyloliquefaciens Bacillus amyloliquefaciens), particularly strain FZB42 (e.g., RHIZOVITAL® from ABiTEP, DE) + TX; Bacillus amyloliquefaciens BS27 (acceptance number NRRL B-5015) + TX;Bacillus cereus family member EE128 (NRRL number B-50917) + TX; Bacillus cereus family member EE349 (NRRL number B-50928) + TX; Bacillus cereus, in particular strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides BT155 (NRRL number B-50921) + TX; Bacillus mycoides Bacillus mycoides EE118 (NRRL number B-50918) + TX; Bacillus mycoides EE141 (NRRL number B-50916) + TX; Bacillus mycoides BT46-3 (NRRL number B-50922) + TX; Bacillus pumilus, especially strain QST2808 (with acceptance number NRRL number B-30087) + TX; Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, DE) + TX; Bacillus siamensis, especially strain KCTC 13613T + TX; Bacillus Bacillus subtilis), particularly strain QST713 / AQ713 (with NRRL acceptance number B-21661, described in U.S. Patent No. 6,060,051, available from Bayer CropScience LP, US as SERENADE® OPTI or SERENADE® ASO) + TX; Bacillus subtilis, particularly strain AQ30002 (with acceptance number NRRL B-50421, described in U.S. Patent Application No. 13 / 330,576) + TX;Bacillus subtilis, particularly strain AQ30004 (and NRRL B-50455, as described in U.S. Patent Application No. 13 / 330,576) + TX; Bacillus subtilis strain BU1814 (available as TEQUALIS® from BASF SE); Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX; Bacillus thuringiensis BT013A (NRRL number B-50924), also known as Bacillus thuringiensis 4Q7 + TX; Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (FMC Mixture of QUARTZO® (WG) and PRESENCE® (WP) from the Corporation + TX; Bacillus subtilis, especially strain MBI 600 (e.g., SUBTILEX® from BASF SE) + TX; Bacillus tequilensis, especially strain NII-0943 + TX; Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes) + TX; Delftia acidovorans, especially strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds) + TX; Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX; Lactobacillus sp.) (e.g., LACTOPLANT® from LactoPAFI) + TX; Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) + TX;Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX; Pseudomonas aeruginosa, especially strain PN1 + TX; Rhizobium leguminosarum, especially bv. viceae strain Z25 (acceptance number CECT 4585) + TX; Paenibacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX; Serratia marcescens, especially strain SRM (acceptance number MTCC 8708) + TX; Sinorhizobium meliloti strain NRG-185-1 (Bayer NITRAGIN® GOLD from CropScience + TX; Thiobacillus sp. (e.g., CROPAID® from Cropaid Ltd UK) + TX; and; (3.2) Fungi, e.g., Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) 251 strains (AGAL 89 / 030550, e.g. BioAct from Bayer CropScience Biologics GmbH) + TX; Penicillium bilaii, ATCC 22348 strain (e.g. JumpStart® from Acceleron BioAg); Talaromyces flavus, strain V117b + TX; Trichoderma atroviride strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR); Trichoderma viride viride), for example, strain B35 (Pietr et al., 1993, Zesz. Nauk.AR w Szczecinie 161:125~137)+TX; Trichoderma atroviride LC52 strain (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies Limited)+TX; Trichoderma atroviride strain SC1 (described in International Application No. PCT / IT2008 / 000196)+TX; Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX; Trichoderma asperellum strain Eco-T (Plant Health Products, ZA), Trichoderma harzianum T-22 strain (e.g., Andermatt Trianum-P from Biocontrol or Koppert + TX; Myrothecium verrucaria AARC-0255 strain (e.g., DiTera® from Valent Biosciences) + TX; Penicillium bilaii ATCC ATCC20851 + TX; Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, CZ) + TX; Trichoderma virens strain GL-21 (e.g., SoilGard® from Certis, USA) + TX; Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276).92, e.g., Dutch Trig)+TX from Tree Care Innovations; Trichoderma atroviride, especially strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390+TX; Trichoderma harzianum strain ITEM 908, Trichoderma harzianum, TSTh20+TX; Trichoderma harzianum strain 1295-22+TX; Pythium oligandrum strain DV74+TX; Rhizopogon amylopogon (e.g., Helena Chemical) (Contained in Myco-Sol from Helena Chemical Company) +TX; Rhizopogon fulvigleba (for example, contained in Myco-Sol from Helena Chemical Company) +TX; Trichoderma virens strain GI-3 +TX; (4) Insecticide biological control agents selected from the following: (4.1) Examples of bacteria include: Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.) + TX; Bacillus amyloliquefaciens, in particular strain PTS-4838 (e.g., AVEO from Valent Biosciences, US) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC., a subsidiary of Mitsui & Co.) + TX; Bacillus sphericus Bacillus sphaericus), particularly serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US) + TX; Bacillus thuringiensis subsp. aizawai, particularly strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX; Bacillus thuringiensis subsp. aizawai, particularly serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., Becker Microbial Products) AQUABAC(registered trademark) by IL) + TX; Bacillus thuringiensis subsp. islaerensis.Bacillus israelensis (serotype H-14) strain AM65-52 (acceptance number ATCC 1276) (e.g., VECTOBAC® by Valent BioSciences, US) +TX; Bacillus thuringiensis subsp. aizawai strain GC-91 +TX; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory) +TX; Bacillus thuringiensis var. japonensis strain Buibui +TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (Becker Microbial) Bacillus thuringiensis subsp. kurstaki strain BMP 123 (BARITONE from Becker Microbial Products, IL, e.g., Bayer CropScience) +TX; Bacillus thuringiensis subsp. kurstaki strain HD-1 (DIPEL® ES from Valent BioSciences, US) +TX; Bacillus thuringiensis var. kurstaki strain EVB-113-19 (BIOPROTEC® from AEF Global) +TX; Bacillus thuringiensis subsp. kurstaki strain ABTS 351+TX; Bacillus thuringiensis subsp. crustakiBacillus thuringiensis subsp. kurstaki strain PB 54+TX; Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN from Certis, US)+TX; Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE from Certis, US)+TX; Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US)+TX; Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US)+TX; Bacillus thuringiensis subsp. tenebryonis * thuringiensis subsp. tenebrionis) strain NB 176 (SD-5428, e.g., NOVODOR® FC from BioFa DE) + TX; * Brevibacillus laterosporus (LATERAL from Ecolibrium Biologicals) + TX; * Burkholderia spp.), in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (acceptance number NRRL B-50319+TX; International Publication No. 2011 / 106491 and International Publication No. 2013 / 032693+TX; e.g., MBI206 TGAI and ZELTO® from Marrone Bio Innovations)+TX; Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203+TX; e.g., GRANDEVO® from Marrone Bio Innovations)+TX; Lecanicillium musculatum Muscarium)Ve6 (MYCOTAL from Koppert) + TX; Paenibacillus popilliae (formerly Bacillus popilliae) + TX; e.g., MILKY SPORE POWDER (trademark) and MILKY SPORE GRANULAR (trademark) from St. Gabriel Laboratories) + TX; Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX; Serratia entomophila (e.g., INVADE (registered trademark) by Wrightson Seeds) + TX; Serratia marcescens, especially strain SRM (acceptance number MTCC 8708) + TX; Trichoderma asperelum Asperellum (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX; and. (4.2) Examples of fungi are as follows: Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain GHA (acceptance number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX; Beauveria bassiana strain ATP02 (acceptance number DSM24665) + TX; Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain Apopka 97)SePRO PREFERAL + TX; Metarhizium anisopriae anisopliae)3213-1 (deposited under NRRL receipt number 67074) (International Publication No. 2017 / 066094 + TX; Pioneer Hi-Bred International) + TX; Metarhizium robertsii 15013-1 (deposited under NRRL receipt number 67073) + TX; Metarhizium robertsii 23013-3 (deposited under NRRL receipt number 67075) + TX; Paecilomyces lilacinus strain 251 (MELOCON from Certis, US) + TX; Zoohtora radicans + TX; (5) Viruses selected from the following group: Adoxophyes orana (apple leafroller) granuloma virus (GV) + TX; Cydia pomonella (codlinga) granuloma virus (GV) + TX; Helicoverpa armigera (tobacco budworm) nuclear polyhedrosis virus (NPV) + TX; Spodoptera exigua (white armyworm) mNPV + TX; Spodoptera frugiperda (sold armyworm) mNPV + TX; Spodoptera littoralis (Egyptian armyworm) NPV + TX; (6) Bacteria and fungi selected from the following which may be added to plants, plant parts, or plant tissues as “inoculated strains” and which promote plant growth and plant health due to their specific characteristics: Agrobacterium spp. + TX; Azorhizobium caulinodans + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX; Gigaspora spp.) or Gigaspora monosporum + TX; Glomus spp. + TX; Laccaria spp. + TX; Lactobacillus buchneri + TX; Paraglomus spp. + TX; Pisolithus tinctorus + TX; Pseudomonas spp. + TX; Rhizobium spp., especially clover rhizobia (Rhizobium trifolii) + TX; Rhizopogon spp. + TX; Scleroderma spp. + TX; Suillus spp. + TX; Streptomyces (spp.)+TX; (7) Plant extracts and products formed by microorganisms containing proteins and secondary metabolites that can be used as biological control agents selected from the following: Allium sativum (NEMGUARD+TX from Eco-Spray; BRALIC from ADAMA)+TX; Armour-Zen+TX; Artemisia absinthium+TX; Azadirachtin (e.g., AZATIN XL from Certis, US)+TX; Biokeeper WP+TX; Brassicaceae plant extracts, especially rapeseed powder or mustard powder+TX; Cassia nigricans+TX; Celastrus angulatus+TX; Chenopodium anthelminticum+TX; Chitin+TX; Dryopteris filix-mas)+TX; Equisetum arvense+TX; Fortune Aza+TX; Fungastop+TX; Heads Up (Chenopodium quinoa saponin extract)+TX; PROBLAD (natural Blad polypeptide from lupine seeds), Certis EU+TX; FRACTURE (natural Blad polypeptide from lupine seeds), FMC+TX; Pyrethrin+TX; Quassia amara+TX; Quercus+TX; Quillaja extract (QL AGRI 35 from BASF)+TX; Reynoutria sachalinensis extract (REGALLIA / REGALIA from Marrone Bio) MAXX)+TX; "Requiem (trademark) insecticide"+TX; Rotenone+TX; Lianya / Ryanodine+TX; Symphytum officinale+TX; Tansy (Tanacetum vulgare)+TX; Thymol+TX; Thymol mixed with geraniol (CEDROZ from Eden Research)+TX; Thymol mixed with geraniol and eugenol (MEVALONE from Eden Research)+TX;Triact 70+TX; TriCon+TX; Tropaeulum majus+TX; Tea tree (Melaleuca alternifolia) extract (TIMOREX GOLD from STK)+TX; Urtica dioica+TX; Veratrin+TX; and Mistletoe (Viscum album)+TX; and; Toxicity mitigating agents, such as benoxacol + TX, cloquintocet (containing cloquintocet-mexyl) + TX, cyprosulfamide + TX, dichloramide + TX, fenchlorazole (containing fenchlorazole-ethyl) + TX, fenchlorim + TX, fluxofenim + TX, flirazole + TX, isoxadifen (containing isoxadifen-ethyl) + TX, mefenpyr (containing mefenpyr-diethyl) + TX, metcamifen + TX, and oxavethrinil + TX.

[0493] For example, a reference in parentheses following an active ingredient, such as [3878-19-1], refers to a Chemical Abstracts Registry number. The aforementioned mixing partners are publicly known. Where an active ingredient is included in “The Pesticide Manual” [The Pesticide Manual-A World Compendium; Thirteenth Edition; Editor: CDSTomLin; The British Crop Protection Council], it is listed therein under the entry number indicated in parentheses above for the specific compound; for example, the compound “abamectin” is listed under entry number (1). Where "[CCN]" is appended to a specific compound mentioned above, the compound in question is included in the “Compendium of Pesticide Common Names,” which is accessible via the internet under [A. Wood; Compendium of Pesticide Common Names, Copyright 1995-2004]; for example, the compound “acetoprole” is listed at the internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0494] Most of the active ingredients listed above are referred to by their so-called "generic names," with the relevant "ISO generic names" or other "generic names" used in individual cases. If a designation is not a "generic name," the nature of the designation used instead is indicated in parentheses for the specific compound; in such cases, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name," "common name," "compound name," or "development code" may be used, or if none of these designations are used and neither is the "generic name," an "alternative name" may be used. "CAS Registry Number" refers to the Chemical Abstract Registry Number.

[0495] The active ingredient mixture of a compound of formula I selected from Tables A-1 to A-48, Tables B-1 to B-48, Tables C-1 to C-48, Tables D-1 to D-48 and Table P, and the above active ingredient, preferably contains the compound s...

Claims

1. Equation (I) 【Chemistry 1】 (In the formula, R 2 is an aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of C 1 to C 6 haloalkyl, C 1 to C 4 haloalkylsulfanyl, C 1 to C 4 haloalkylsulfinyl, C 1 to C 4 haloalkylsulfonyl or C 1 to C 6 haloalkoxy, halogen, cyano, cyclopropyl or aryl, wherein the halogen, cyano, C 1 to C 4 alkyl, C 1 to C 4 haloalkyl, C 1 to C 4 alkoxy, C 1 to C 4 haloalkoxy, C 1 to C 4 alkylsulfanyl, C 1 to C 4 alkylsulfinyl and C 1 to C 4 alkylsulfonyl; G is either CH or N; X 1 is O, S or NR 6 And R 6 C 1 ~C 4 It is alkyl; Q is expressed in equations Qa and Qb 【Chemistry 2】 A group selected from the group consisting of, In the equation, the arrows indicate the bonding points to the biring ring; A represents CH or N; X is S, SO, SO 2 And; R 1 C 1 ~C 4 Alkyl or C 3 ~C 6 Cycloalkyl-C 1 ~C 4 It is alkyl; Q 1 is hydrogen, halogen, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyl, and C is single-substituted with 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 ) COR 5 or 2-pyridyloxy; or Q 1 This is a 5-6 member aromatic or aromatic heterocyclic system bonded to the ring containing substituent A via a ring carbon atom, wherein the ring system is unsubstituted or contains halogens, cyanocarbons, or carbon atoms. 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkyl sulfanyl, C 1 ~C 4 Alkyl sulfinyl and C 1 ~C 4 It is monosubstituted or polysubstituted by substituents selected from the group consisting of alkylsulfonyls; and the ring system may contain one, two or three ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the ring system may not contain two or more ring oxygen atoms and may not contain two or more ring sulfur atoms; or Q 1 This is a five-membered aromatic heterocyclic system bonded to the ring containing substituent A via a ring nitrogen atom, wherein the ring system is unsubstituted or contains halogen, cyano, or C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkyl sulfanyl, C 1 ~C 4 Alkyl sulfinyl and C 1 ~C 4 The ring system is monosubstituted or polysubstituted by substituents selected from the group consisting of alkylsulfonyls; and the ring system contains one, two or three ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; the ring system contains at least one ring nitrogen atom and cannot contain two or more ring oxygen atoms and cannot contain two or more ring sulfur atoms; R 3 is hydrogen or C 1 to C 4 alkyl; Each R 4 These are, independently, hydrogen, C 1 ~C 4 Alkyl or C 3 ~C 6 It is cycloalkyl; and R 5 is C 1 to C 6 alkyl, C 1 to C 6 haloalkyl or C 3 to C 6 cycloalkyl). Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides of the compound of formula I.

2. Formula I-1 【Transformation 3】 (In the formula, R 2 G, X 1 , R 6 A, X, R 1 Q 1 , R 3 , R 4 and R 5 (This is as defined under Formula I of Claim 1.) Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides of the compound of formula I or formula I-1 described in claim 1, represented by the compound of formula I-1.

3. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is either CH or N; X 1 is O, S, or NCH 3 And; A is either N or CH; X is S or SO 2 And; R 1 is ethyl or cyclopropylmethyl; Q 1 Hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 ) CO (cyclopropyl) or 2-pyridyloxy; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen or methyl.

4. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is CH; X 1 is O; A is N; X is SO 2 And; R 1 It is ethyl; Q 1 Hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 ) CO (cyclopropyl) or 2-pyridyloxy; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen.

5. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is either CH or N; X 1 is O, S, or NCH 3 And; A is either N or CH; X is S or SO 2 And; R 1 is ethyl or cyclopropylmethyl; Q 1 This refers to N-linked triazolyl, C-linked pyrimidinyl, or N-linked pyrazolyl, which can be monosubstituted with chloro, cyano, or trifluoromethyl; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen or methyl.

6. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is CH; X 1 is O; A is N; X is SO 2 And; R 1 It is ethyl; Q 1 These are pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl or pyrimidine-2-yl; and R 3 The compound of formula I-1 according to claim 2, wherein is hydrogen.

7. Equation I-2 【Chemistry 4】 (In the formula, R 2 G, X 1 , R 6 A, X, R 1 Q 1 , R 3 , R 4 and R 5 (This is as defined under Formula I of Claim 1.) Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides of the compound of formula I or formula I-2 described in claim 1, represented by the compound.

8. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is either CH or N; X 1 is O, S, or NCH 3 And; A is either N or CH; X is S or SO 2 And; R 1 is ethyl or cyclopropylmethyl; Q 1 It is hydrogen, cyclopropyl, -NH(CH 3 ), -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 or -N(CH 3 ) CO (cyclopropyl); and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen or methyl.

9. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is CH; X 1 is O; A is N; X is SO 2 And; R 1 It is ethyl; Q 1 It is hydrogen, cyclopropyl, -NH(CH 3 ), -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 or -N(CH 3 ) CO (cyclopropyl); and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen.

10. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is either CH or N; X 1 is O, S, or NCH 3 And; A is either N or CH; X is S or SO 2 And; R 1 is ethyl or cyclopropylmethyl; Q 1 is an N-linked triazolyl or a C-linked pyrimidinyl; and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen or methyl.

11. R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxys, halogens, cyanos, or phenyls, wherein the phenyl is substituted with one or two halogen atoms; G is CH; X 1 is O; A is N; X is SO 2 And; R 1 It is ethyl; Q 1 is 1,2,4-triazole-1-yl or pyrimidine-2-yl; and R 3 The compound of formula I-2 according to claim 7, wherein is hydrogen.

12. Formula I-3 【Transformation 5】 (In the formula, R 2 C 1 ~C 2 Fluoroalkyl, C 1 ~C 2 Fluoroalkoxy, halogen, cyano, or phenyl, wherein the phenyl is substituted with a halogen; G is either CH or N; X 1 is O, S, or NCH 3 And; Q' is given by equations Qa1 and Qb1 【Transformation 6】 A group selected from the group consisting of, In the equation, the arrows indicate the bonding points to the biring ring; Q 1 is hydrogen, trifluoromethyl, difluoroethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, trifluoroethoxy, difluoropropoxy, 2-pyridyloxy, N-linked pyrazolyl, which can be monosubstituted with chloro, cyano, or trifluoromethyl; or Q 1 This refers to N-linked triazolyl, C-linked pyrimidinyl, or -N(R) 4 ) COR 5 And R 4 is hydrogen or methyl, and R 5 (It is either methyl, ethyl, or cyclopropyl.) Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides of the compound of formula I or formula I-3 described in claim 1, represented by the compound.

13. Q 1 Hydrogen, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy, -N(CH 3 ) COCH 3 , -N(CH 3 ) COCH 2 CH 3 , -N(CH 3 The compound of formula I-3 according to claim 12, wherein the compound is CO (cyclopropyl), 2-pyridyloxy, pyrazole-1-yl, 3-chloropyrazole-1-yl, 3-cyanopyrazole-1-yl, 3-trifluoromethylpyrazole-1-yl, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

14. Q 1 The compound of formula I-3 according to claim 12, wherein is hydrogen, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, cyanoisopropoxy, N-linked triazolyl, or C-linked pyrimidinyl.

15. Q 1 The compound of formula I-3 according to claim 12, wherein is hydrogen, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, 1,2,4-triazole-1-yl, or pyrimidine-2-yl.

16. G is CH; and X 1 A compound of formula I-3 according to any one of claims 12 to 15, wherein is O.

17. G is N; and X 1 A compound of formula I-3 according to any one of claims 12 to 15, wherein is O.

18. R 2 -CF 3 , -CF 2 CF 3 ,-CHF 2 , -OCF 3 , -OCHF 2 A compound of formula I according to any one of claims 1 to 17, wherein the compound is cyano, fluoro, chloro, bromo, iodine, 3,5-difluorophenyl, or 4-fluorophenyl.

19. R 2 -CF 3 A compound of formula I according to any one of claims 1 to 18, wherein the compound is fluoro, chloro, bromo, iodo, or 4-fluorophenyl.

20. 1-[5-ethylsulfonyl-6-[4-oxo-6-(trifluoromethyl)chromen-3-yl]-3-pyridyl]cyclopropanecarbonitric (compound P.1); 1-[5-ethylsulfonyl-6-(6-fluoro-4-oxochromen-3-yl)-3-pyridyl]cyclopropanecarbonitric (compound P.2); 1-[6-(6-chloro-4-oxo-chromen-3-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitric (compound P.3); 3-[5-(1-cyanocyclopropyl)-3-ethylsulfonyl-2-pyridyl]-4-oxochromene-6-carbonitrile (compound P.4); 1-[6-(6-bromo-4-oxochromen-3-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitric (compound P.5); 1-[5-ethylsulfonyl-6-(6-iodo-4-oxochromen-3-yl)-3-pyridyl]cyclopropanecarbonitric (compound P.6); 1-[6-[6-(3,5-difluorophenyl)-4-oxo-chromen-3-yl]-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitric (compound P.7); 1-[5-ethylsulfonyl-6-[6-(4-fluorophenyl)-4-oxo-chromen-3-yl]-3-pyridyl]cyclopropanecarbonitric (compound P.8) A compound of formula I according to claim 1, selected from the group consisting of the following:

21. A composition comprising an amount effective in insecticidal, acaricidal, nematicidal, or molluscicidal of a compound of formula (I) according to any one of claims 1 to 20, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, and optionally an auxiliary agent or diluent.

22. A method for controlling and eliminating insects, mites, nematodes, or mollusks, comprising applying an insecticidal, acaricidal, nematodetic, or molluscicidal amount of a compound of formula (I) according to any one of claims 1 to 20, or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof, or the composition according to claim 21, to a pest, a habitat of a pest, or a plant susceptible to attack by a pest.

23. A method for protecting plant propagation material from attacks by insects, mites, nematodes, or mollusks, comprising treating the propagation material or the place where the propagation material is planted with the composition described in claim 21.

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