Microbicidal pyridazine dihydrooxadiazine derivatives.

Abstract

Compounds of formula (I) which are useful as pesticides, particularly fungicides JPEG2026502124000071.jpg32160 (in the formula, R 1 , R 2 and G are as defined in claim 1) Compound.

Description

[Technical Field]

[0001] The present invention relates to pyridazine dihydrooxadiazines as active ingredients having microbicidal, especially fungicidal, activity. The present invention also relates to agrochemical compositions comprising at least one pyridazine 5,6-dihydro-4H-1,2,4-oxadiazine derivative, processes for preparing these compounds, and the use of pyridazine 5,6-dihydro-4H-1,2,4-oxadiazine derivatives or compositions in agriculture or horticulture to control or prevent infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, preferably fungi. [Background technology]

[0002] Many plant protection compounds have been developed to prevent or reduce plant diseases caused by microorganisms, such as fungi. For example, International Publication No. 2020 / 109391 discloses pyridazine (thio)amide derivatives. International Publication No. 2020 / 127780 discloses pyridazine oxadiazine derivatives. Summary of the Invention

[0003] Thus, the present invention provides in a first aspect a compound of formula (I) [ka] (In the formula, R 1 is phenyl and is unsubstituted, or a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me)2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl, or - 1, 2 or 3 substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; or -R 1 is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms each independently selected from N, O, and S, provided that not more than one is O or S, said heteroaryl ring being unsubstituted; or a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me)2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl, or - one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by R 2is hydrogen, hydroxyl, nitro, halogen, mercapto, amino, cyano, C1-C6 alkyl, C1-C2 fluoroalkyl, C3-C5 alkenyl, C3-C5 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl or C3-C6 cycloalkylC 1-2 alkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C5 alkenyloxy, C3-C5 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C4 alkylamino, di-C1-C4 alkylamino, C3-C5 alkenylamino, C3-C5 alkynylamino, C1-C3 alkylsulfanyl or C1-C3 alkylsulfonyl, or R 2 is phenyl, phenyl C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heterocyclyl, heterocyclyl C1-C2 alkyl, C3-C6 cycloalkyl or C3-C6 cycloalkylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring containing 1, 2, or 3 heteroatoms independently selected from N, O, and S, provided that not more than one is O or S, and the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring containing 1 or 2 heteroatoms independently selected from N, O, and S, provided that not more than one is O or S, and wherein all of the cycloalkyl, phenyl, heteroaryl, and heterocyclyl moieties are unsubstituted; or a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me)2, C1-C4 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, C3-C6 cycloalkyl, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl, or - one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by G is selected from G-1, G-2, G-3 and G-4; G-1 is phenyl or phenoxy, said phenyl or phenoxy being unsubstituted, or a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me)2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl, or - one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by - G-2 is a 5- or 6-membered monocyclic heteroaryl or heteroaryloxy, said heteroaryl containing 1, 2 or 3 heteroatoms each independently selected from N, O and S, provided that not more than one is O or S, and said heteroaryl or heteroaryloxy is unsubstituted; or a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me)2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl, or - one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by G-3 is a 9- or 10-membered heterobicyclic ring system containing one, two, or three heteroatoms each independently selected from N, O, and S, provided that not more than one is O or S, said heterobicyclic ring system being saturated, partially unsaturated, or aromatic, said heterobicyclic ring system being unsubstituted or having a single substituent that is hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me), C substituted by a single substituent selected from 1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl; G-4 is a 9- or 10-membered carbobicyclic ring system, said carbobicyclic ring system being saturated, partially unsaturated or aromatic, said carbobicyclic ring system being unsubstituted or substituted with a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me), C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C2 fluoroalkyl, C1-C4 alkoxy, C1-C2 fluoroalkoxy, C3-C4 alkenyloxy, C3-C4 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C2 alkyloxy, C1-C3 alkylsulfanyl and C1-C3 alkylsulfonyl. or an agrochemically acceptable salt, stereoisomer, enantiomer or N-oxide thereof.

[0004] The present invention also provides methods for preparing compounds of formula (I) and intermediate compounds useful in the preparation of compounds of formula (I).

[0005] Surprisingly, it has now been found that the novel compounds of formula (I) have a very advantageous level of biological activity which, in practice, protects plants against diseases caused by fungi.

[0006] According to a second aspect of the present invention there is provided an agricultural composition comprising a fungicidally effective amount of a compound of formula (I). Such agricultural compositions may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0007] According to a third aspect of the present invention there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) or a composition comprising this compound as an active ingredient is applied to the plant, a part thereof or its habitat.

[0008] According to a fourth aspect of the present invention, there is provided the use of a compound of formula (I) as a fungicide. According to this particular aspect of the present invention, this use may be in methods for treating the human or animal body by surgery or therapy.

[0009] According to a fifth aspect, the present invention provides plant propagation material, such as a seed, comprising, treated with or having attached thereto a compound of formula (I) or a composition comprising such a compound. DETAILED DESCRIPTION OF THE INVENTION

[0010] As used herein, the term "hydroxyl" or "hydroxy" refers to an --OH group.

[0011] As used herein, the term "methylcapto" refers to an --SH group.

[0012] As used herein, the term "cyano" refers to a -CN group.

[0013] As used herein, amino refers to the group —NH 2 .

[0014] As used herein, nitro refers to the group —NO 2 .

[0015] As used herein, oxo means a ═O group (eg, as in a carbonyl (C═O) group).

[0016] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine. This equally applies to halogen in combination with other meanings, such as haloalkyl.

[0017] As used herein, the term "C1-C6 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from 1 to 6 carbon atoms, and attached to the remainder of the molecule by a single bond. C1-C4 alkyl should be construed accordingly. Examples of C1-C6 alkyl include, but are not limited to, methyl, ethyl, and isopropyl.

[0018] As used herein, the term "C2-C4 alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, having two or four carbon atoms attached to the rest of the molecule by a single bond, and containing at least one double bond which may be in either the (E) or (Z) configuration. Examples of C2-C4 alkenyl include, but are not limited to, vinyl (ethenyl), prop-1-enyl, and allyl (prop-2-enyl).

[0019] As used herein, the term "C2-C4 alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having two or four carbon atoms, and attached to the rest of the molecule by a single bond. Examples of C2-C4 alkynyl include, but are not limited to, prop-1-ynyl and propargyl (prop-2-ynyl).

[0020] As used herein, the term "C1-C2 fluoroalkyl" refers to a C1-C2 alkyl group, generally as defined above, substituted with one or more fluorine atoms. Examples of C1-C2 fluoroalkyl include, but are not limited to, difluoromethyl and trifluoromethyl.

[0021] As used herein, the term "C1-C4 alkoxy" refers to a group of the formula R a O-(wherein, R agenerally refers to a group represented by the formula: (which is a C1-C4 alkyl group as defined above). Examples of C1-C4 alkoxy include, but are not limited to, methoxy, ethoxy, and isopropoxy.

[0022] As used herein, the term "C1-C2 fluoroalkoxy" refers to a C1-C2 alkoxy group, generally as defined above, substituted with one or more fluorine atoms. Examples of C1-C2 fluoroalkoxy include, but are not limited to, difluoromethoxy or trifluoromethoxy.

[0023] As used herein, the term "C3-C6 cycloalkyl" refers to a stable monocyclic ring group that is saturated and contains from 3 to 6 carbon atoms.

[0024] As used herein, the term “C-C alkenyloxy” refers to a group of the formula R a O-(wherein, R a generally refers to a group represented by the formula: C3-C4 alkenyl group as defined above. Examples of C3-C4 alkenyloxy include, but are not limited to, allyloxy.

[0025] As used herein, the term "C-C alkynyloxy" refers to a group of the formula R aO - (wherein Ra is generally a C3-C4 alkynyl group as defined above). Examples of C3-C4 alkynyloxy include, but are not limited to, propargyloxy.

[0026] As used herein, the term "C-C cycloalkoxy" refers to a group of the formula R a O-(wherein, R a generally refers to a group represented by the group C3-C6 cycloalkyl, as defined above. Examples of C3-C6 cycloalkoxy include, but are not limited to, cyclopropoxy.

[0027] As used herein, the term "C-C cycloalkyl C-C alkyl" refers to a group of the formula R a O-(wherein, R a generally refers to a group represented by the above-defined C3-C6 cycloalkyl C1-C2 alkyl group. Examples of C3-C6 cycloalkyl C1-C2 alkyloxy include, but are not limited to, cyclopropylmethyl.

[0028] As used herein, the term "C-C cycloalkylC-C alkyloxy" refers to a group of the formula R a O-(wherein, R a generally refers to a group represented by the formula (wherein C3-C6 cycloalkyl C1-C2 alkyl group is as defined above). Examples of C3-C6 cycloalkyl C1-C2 alkyloxy include, but are not limited to, cyclohexylmethoxy.

[0029] As used herein, the term "C1-C3 alkylsulfanyl" refers to a group of the formula -SR a (In the formula, R a generally refers to a group represented by the formula (which is a C1-C3 alkyl group as defined above).

[0030] As used herein, the term "C1-C3 alkylsulfonyl" refers to a group of the formula -S(O)R a (In the formula, R a generally refers to a group represented by the formula (which is a C1-C3 alkyl group as defined above).

[0031] The term "heteroaryl" as used herein refers to a 5- or 6-membered aromatic monocyclic ring having 1 to 3 heteroatoms independently selected from N, O, and S. Examples of heteroaryl include J-1 to J-43 shown in Table J below. The zigzag line in heteroaryl J-1 to J-39 represents the point of attachment to the remainder of the compound. Preferred heteroaryls include pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, and thiazolyl, preferably pyridinyl and thiazolyl.

[0032] [Table 1]

[0033] The term "heterocyclyl" as used herein refers to a 3-, 4-, 5-, or 6-membered saturated monocyclic ring having one or two heteroatoms independently selected from nitrogen and oxygen. Examples of heterocyclyls include K-1 to K-26 shown in Table K below. The zigzag line in heterocyclyls K-1 to K-26 represents the point of attachment to the remainder of the compound. Some of the heterocyclyls shown below contain asymmetric carbons, meaning that compounds containing them can occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Preferred heterocyclyls include pyrrolidinyl, piperidinyl, piperazinyl, and tetrahydropyranyl, preferably pyrrolidinyl, piperazinyl, and tetrahydropyranyl.

[0034] [Table 2]

[0035] As used herein, the term "optionally substituted" means that the referenced group is unsubstituted or substituted with the specified substituents, for example, "phenyl may be optionally substituted with one or two halo atoms" refers to phenyl substituted with one halo atom and phenyl substituted with two halo atoms. The term "optionally substituted" can be used interchangeably with "unsubstituted or substituted."

[0036] As used herein, the term "control" refers to reducing the number of pests, eliminating pests, and / or preventing further pest damage so that damage to plants or plant-derived products is reduced.

[0037] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, the storage of plant-based products (such as fruit, grain, and lumber), and pests associated with damage to man-made structures. The term pest encompasses all stages in the life cycle of a pest.

[0038] As used herein, the term "effective amount" refers to the amount of a compound or salt thereof that produces a desired effect upon one or more applications.

[0039] Effective amounts are readily determined by those skilled in the art by the use of known techniques and by observing results obtained under analogous circumstances. In determining an effective amount, many factors are taken into consideration, including, but not limited to, the type of plant or plant-derived product to be applied, the pest to be controlled and its life cycle, the particular compound applied, the type of application, and other relevant circumstances.

[0040] As used herein, the terms "room temperature," or "RT," or "rt," or "ambient temperature" refer to a temperature of about 15° C. to about 35° C. For example, rt can refer to a temperature of about 20° C. to about 30° C.

[0041] As used herein, the zigzag lines in the examples, for example, the heteroaryls shown in Table J and the heterocyclyls shown in Table K, represent points of connection / attachment to the remainder of the compound.

[0042] The presence of one or more possible asymmetric carbon atoms in the compounds of formula (I) means that the compounds can occur in chiral isomeric, i.e., enantiomeric or diastereomeric forms. Atropisomers can also occur as a result of restricted rotation around a single bond. Formula (I) is intended to include all its possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms of the compounds of formula (I) and mixtures thereof. Similarly, formula (I) is intended to include all possible tautomeric forms, if present, including lactam-lactim tautomers and keto-enol tautomers. The present invention includes all possible tautomeric forms of the compounds of formula (I).

[0043] The compounds of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, for example, perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid, hydrohalic acids, etc.; with strong organic carboxylic acids, for example, unsubstituted or halogen-substituted C1-C4 alkane carboxylic acids, such as acetic acid; saturated or unsaturated dicarboxylic acids, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, phthalic acid, etc.; hydroxycarboxylic acids, for example, ascorbic acid, lactic acid, malic acid, tartaric acid, citric acid, or benzoic acid; or with organic sulfonic acids, for example, unsubstituted or halogen-substituted C1-C4 alkane or aryl sulfonic acids, for example, methane or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0044] The compounds of formula (I) according to the present invention also include hydrates which may be formed upon formation of salts.

[0045] In each case, the compounds of formula (I) according to the invention may be in free form, oxidized form as N-oxide, covalently hydrated form or in salt form, for example in agriculturally usable or agrochemically acceptable salt form.

[0046] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds, as described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0047] The following list refers to compounds of formula (I) of the present invention and defines substituent R 1 , R 2 and G. Any of the definitions given below for any one of these substituents may be combined with any definition of any other substituent below or elsewhere in this specification.

[0048] In one embodiment of each aspect of the invention, R 1 is as follows: A. Phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents, such as a single substituent, independently selected from hydroxyl, halogen, mercapto, amino, nitro, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, isopropoxy, tert-butoxy, propynoxy, NHMe, N(Me), methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or B. Phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents, such as a single substituent independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyloxy; or C. Phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents, such as one substituent independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or D. Pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents, such as one substituent independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or E. Phenyl substituted with one or two substituents, such as one substituent independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy; or F. Phenyl substituted with a single substituent selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy; or G. 2-Fluoro-3-cyclopropylphenyl, 2-fluoro-3-methylphenyl, 2-fluorophenyl, 3-(difluoromethoxy)phenyl, 3-(trifluoromethoxy)phenyl, 2-(trifluoromethyl)pyridin-4-yl, 3-ethoxyphenyl, 3-ethylphenyl, 3-ethynylphenyl, 3-fluorophenyl, 4-(difluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl, 4-chlorophenyl, 4-cyanophenyl, 4-ethoxyphenyl, 4-ethylphenyl, 4-fluorophenyl, 3-methoxyphenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3,4-dimethoxyphenyl, 3,5-dichlorophenyl, 3,5-difluorophenyl, 3-cyanophenyl, 3,4-difluorophenyl, 3,4-dimethoxyphenyl, 3,5-dichlorophenyl, 3,5-difluorophenyl, 3-cyanophenyl, 2-methylpyrimidin-4-yl, 2-(trifluoromethyl)pyridin-4-yl pyridin-4-yl, 3-(trifluoromethyl)pyridin-2-yl, 3-methoxypyridin-2-yl, 3-methylpyridin-2-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-cyanopyridin-3-yl, 2-fluoropyridin-3-yl, 2-methoxypyridin-4-yl, 2-methylpyridin-3-yl, 5-(trifluoromethyl)pyridin-3-yl, 5-chloropyridin-3-yl, 5-cyanopyridin-3-yl, 5-cyclopropylpyridin-3-yl 6-(trifluoromethyl)pyridin-3-yl, 6-chloropyridin-2-yl, 6-cyanopyridin-3-yl, 6-cyclopropylpyridin-2-yl, 6-methoxypyridin-3-yl, 6-methyl-2-pyridyl, 6-methylpyridazin-3-yl, 6-methylpyridin-2-yl, 6-methylpyridin-3-yl, pyridin-3-yl, pyridin-4-yl or phenyl, or H. 3-cyclopropyl-2-fluorophenyl, 3-(trifluoromethyl)phenyl, 3-chloro-2-fluorophenyl, 3-chlorophenyl, 5-cyanopyridin-3-yl, 3-methylphenyl, phenyl, 3-cyclopropylphenyl, 3-(difluoromethyl)phenyl, 3-(difluoromethoxy)phenyl, 3-(trifluoromethyl)-2-fluorophenyl, 3-methoxyphenyl or 2,3-difluorophenyl, or I. phenyl, 3-(trifluoromethyl)phenyl, 3-methoxyphenyl, 3-cyclopropylphenyl, 3-cyclopropyl-2-fluorophenyl or 5-cyanopyridin-3-yl, or J. 3-cyclopropylphenyl.

[0049] For example, in one embodiment of each aspect of the invention, R 1 is as follows: A. phenyl, unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, mercapto, amino, nitro, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, isopropoxy, tert-butoxy, propynoxy, NHMe, N(Me), methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl, and cyclopropyloxy; or B. Phenyl, unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, trifluoromethoxy, and cyclopropyl; or C. Phenyl, unsubstituted or substituted with one or two substituents each independently selected from chloro, fluoro, cyano, methyl, methoxy, difluoromethoxy, and cyclopropyl; or D. phenyl, unsubstituted or substituted with one or two substituents each independently selected from fluoro, chloro, cyano, methyl, and cyclopropyl; or E. Phenyl, unsubstituted or substituted with a single substituent selected from fluoro, chloro, methyl and cyclopropyl.

[0050] For example, in one embodiment of each aspect of the invention, R 1 is also: A. 5- or 6-membered monocyclic heteroaryl rings containing 1, 2, or 3 heteroatoms, which may be the same or different, independently selected from N, O, and S, provided that not more than one is O or S, said heteroaryl ring being unsubstituted or substituted with 1 or 2 substituents, each independently selected from hydroxyl, halogen, mercapto, amino, nitro, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, isopropoxy, tert-butoxy, propynoxy, NHMe, N(Me), methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, and cyclopropyl; B. A pyridine, pyrimidine or pyridazine, wherein said pyridine, pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; or C. Pyridine substituted with one or two substituents each selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, and cyclopropyl; or D. Pyridine substituted with a single substituent selected from chloro, fluoro, cyano, methyl, methoxy, difluoromethoxy, and cyclopropyl; or E. Pyridine substituted with a single substituent selected from chloro, cyano, methyl and cyclopropyl.

[0051] In one embodiment of each aspect of the invention, R 2 is as follows: A. hydrogen, hydroxyl, halogen, mercapto, amino, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 fluoroalkyl, C1-C4 fluoroalkoxy or C3-C4 cycloalkyl; B. hydrogen, hydroxyl, halogen, amino, cyano, C1-C4 alkyl, C1-C4 alkoxy, C3-C4 cycloalkyl, C2-C4 alkenyl, C1-C4 alkylethynyl, C3-C4 cycloalkylethynyl or C2-C4 alkenyloxy, or C. hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, 2-methylallyloxy or isopropoxy; D. hydrogen, hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, isopropoxy, propynoxy, NHMe, N(Me)2, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl or cyclopropyloxy; or E. hydrogen, hydroxyl, halogen, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy or cyclopropyl, or F. hydrogen, hydroxyl, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl or cyclopropyl; G. hydrogen, hydroxy, cyano, mercaptyl, fluoro, chloro, methyl or ethyl; H. hydrogen, hydroxyl, chloro, cyano, methyl, ethyl, methoxy or cyclopropyl; I. Hydrogen, methyl, ethyl or cyclopropyl.

[0052] In certain embodiments of each aspect of the invention, G is G-1, as follows: A. phenyl or phenoxy, unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, and cyclopropyl; or B. Phenyl or phenoxy, unsubstituted or substituted with one or two substituents each selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethylmethoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, trifluoromethoxy and cyclopropyl; or C. Phenyl, unsubstituted or substituted with one, two or three substituents, for example, two or three substituents each independently selected from chloro, fluoro, bromo, methyl, methoxy and cyclopropyl; or D. phenyl substituted with one or two substituents, for example, one substituent each independently selected from chloro and methyl; or E. 2,4-dichlorophenyl.

[0053] In one embodiment of each aspect of the invention, G is G-2 as follows: A. pyridine, pyrimidine, pyridazine, pyridinoxy, pyrimidinoxy, pyridazinoxy, wherein the pyridine, pyrimidine, or pyridazine ring is unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, and cyclopropyl; or B. Pyridine, unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, and cyclopropyl; or C. A pyrimidine or pyridazine, wherein the pyrimidine or pyridazine is unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, and cyclopropyl; or D. Pyridine, unsubstituted or substituted with one or two substituents each selected from chloro, fluoro, cyano, methyl and methoxy; or E. Pyridine or pyridinoxy, which is unsubstituted or substituted with a single substituent selected from chloro and methyl.

[0054] In one embodiment of each aspect of the invention, G is G-3 as follows: A. chroman-4-yl, isochroman-4-yl, 4H-chromen-4-yl, 2,3-dihydrobenzofuran-2-yl, 2,3-dihydrobenzofuran-3-yl, 1,3-benzodioxol-5-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, benzoxazol-6-yl, benzofuran-2-yl, benzofuran-3-yl, benzofuran-5-yl, benzofuran-6-yl, benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-5-yl or benzothiophen-6-yl, which are unsubstituted or substituted with one or two substituents, e.g., a single substituent each independently selected from chloro, fluoro, cyano, methyl and methoxy; B. chroman-4-yl, isochroman-4-yl, 4H-chromen-4-yl, 2,3-dihydrobenzofuran-2-yl, 2,3-dihydrobenzofuran-3-yl, 1,3-benzodioxol-5-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzofuran-2-yl, benzofuran-3-yl, benzothiophen-2-yl or benzothiophen-3-yl, which are unsubstituted or substituted with a single substituent selected from chloro, fluoro, cyano, methyl and methoxy; C. chroman-4-yl, isochroman-4-yl, 4H-chromen-4-yl, 2,3-dihydrobenzofuran-2-yl or 2,3-dihydrobenzofuran-3-yl, which is unsubstituted or substituted with a single substituent selected from chloro, fluoro, cyano, methyl and methoxy, or D. 1,3-benzodioxol-5-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzooxazol-2-yl, benzofuran-2-yl, benzofuran-3-yl, benzothiophen-2-yl or benzothiophen-3-yl.

[0055] In certain embodiments of each aspect of the invention, G is G-4, as follows: A. naphthalen-2-yl, tetralin-1-yl, tetralin-2-yl, tetralin-6-yl, indan-1-yl, indan-2-yl or indan-5-yl, which is unsubstituted or substituted with one or two substituents, e.g., a single substituent each independently selected from chloro, fluoro, cyano, methyl and methoxy, or B. Tetralin-1-yl, tetralin-2-yl, indan-1-yl or indan-2-yl that is unsubstituted or substituted with one or two substituents, e.g., a single substituent each independently selected from chloro, fluoro, cyano, methyl and methoxy.

[0056] For example, in each embodiment of the present invention, G is: A. 2,4-dimethylphenyl, 2,4-dichlorophenyl, 4-bromo-2-methylphenyl, 4-bromo-2-chlorophenyl, 2,6-dichloro-3-pyridyl, 4,6-dichloro-3-pyridyl, 3,5-dichloro-2-pyridyl, 3,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-methyl-4-bromophenyl, 2-methyl-4-chlorophenyl or 2,4-difluorophenyl, or B. 2,4-dimethylphenyl, 2,4-dichlorophenyl, 4-bromo-2-methylphenyl, 4-bromo-2-chlorophenyl, 2,6-dichloro-3-pyridyl, 4,6-dichloro-3-pyridyl, 3,5-dichloro-2-pyridyl, 3,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-methyl-4-bromophenyl or 2-methyl-4-chlorophenyl, or C. 2,4-dimethylphenyl, 2,4-dichlorophenyl, 4-bromo-2-methylphenyl, 4-bromo-2-chlorophenyl, 3,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-methyl-4-bromophenyl, 2-methyl-4-chlorophenyl or 2,4-difluorophenyl, or D. 2,6-dichloro-3-pyridyl, 4,6-dichloro-3-pyridyl or 3,5-dichloro-2-pyridyl, or E. 2,4-dichlorophenyl.

[0057] The compound of formula (I) is represented by the formula (I*) (wherein R 1 , R 2 and G are as defined in the first aspect, each with the corresponding embodiments above, and may include the stereocenters indicated with an asterisk. [ka]

[0058] The compound of the present invention has formula (I-1) or formula (I-2): [ka] The compound of formula (I) may be an enantiomer of the compound of formula (I) represented by:

[0059] Formula (I) [ka] The compounds can be prepared by those skilled in the art according to the following schemes 1 to 32 (wherein G, R 1 and R 2 Compounds of formula (I) can be prepared as shown in the following formula (Ia): [ka] (Wherein, G and R 1 is as defined above for compounds of formula (I), and (A) is a pyridazinyl moiety: [ka] (wherein ## represents -OR 1 indicates bond to the 5,6-dihydro-4H-1,2,4-oxadiazin-3-yl moiety, R 2is as defined above for compounds of formula (I) unless otherwise specified. (represents The same definition of (A) applies to certain intermediate compounds shown in Schemes 1-32, particularly compounds of formula (I), (II), (III), (IV), (VIII), (IX), (X), (XI), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), (XX), (XXI), (XXII), (XXIV), (XXV), (XXVI), (XXVII), (XXVIII), (XXIX), (XXX), (XXXI), (XXXII), (XXXIII), and (XXXIV). Specific stereocenters have not been specified for the sake of clarity and are not intended to limit the teaching of the Schemes in any way.

[0060] As shown in Scheme 1 below, 1 are as defined for compounds of formula (I), can be converted to compounds of formula (II) (wherein G and R are as defined for compounds of formula (I)) using a chlorinating agent, for example by using POCl, PCl, (COCl) or SOCl in a suitable solvent or mixture of solvents (e.g., dichloromethane, dichloroformamide, 2-methyltetrahydrofuran, tetrahydrofuran, diethyl ether, toluene, ethyl acetate), preferably at a temperature between 0°C and 80°C, more preferably between 25°C and 60°C, optionally in the presence of dimethylformamide. 1 can be obtained by intramolecular cyclization of a compound of formula (I) (wherein R is as defined for the compound of formula (I)). See, for example, Heterocycles 2016, 92, 2166-2200 or Chinese Patent No. 114437077. [ka] Scheme 1

[0061] As shown in Scheme 2 below, 1 are as defined for compounds of formula (I), the compounds of formula (III)1 is as defined for compounds of formula (I), and X 1 is H and X 2 is a protecting group, or X 1 and X 2 are the same or different protecting groups, or X 1 and X 2 can be obtained by amine deprotection of a compound of formula (wherein, together with the nitrogen to which they are attached, form a protecting group). Examples of protecting groups include, for example, tert-butyloxycarbonyl, benzylcarbonyl, 9-fluorenylmethylcarbonyl, trifluoroacetyl, benzyl, triphenylmethyl, benzylidenyl, p-trienesulfonyl, phthalimide, or succinimide. Protecting groups can be removed using standard techniques (see Greene's Protective Groups in Organic Synthesis, 4th Ed., Wiley-Interscience). [ka] Scheme 2

[0062] As shown in Scheme 3 below, a compound of formula (III) (wherein G and R 1 is as defined for compounds of formula (I), and X 1 and X 2 is as defined for compounds of formula (III) in Scheme 2, can be prepared by reacting a compound of formula (IV) (wherein G is as defined for compounds of formula (I)) and a compound of formula (V) (wherein X is as defined for compounds of formula (I) 1 and X 2Amine compounds of formula (III) (wherein R is as defined for compound of formula (III) in Scheme 2) can be obtained by activating the carboxylic acid functionality of compound of formula (IV) to undergo an amide coupling transformation. This is a process that typically occurs by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl) or SOCl, before treating with compound of formula (IV), preferably at a temperature between 25° C. and 60° C., optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran).

[0063] Alternatively, compounds of formula (III) can be obtained under conditions described in the literature for amide coupling using an amidating coupling reagent such as 1-propanephosphonic acid cyclic anhydride (T3P) in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084. [ka] Scheme 3

[0064] As shown in Scheme 4 below, a compound of formula (II) (wherein G and R 1 is as defined for compounds of formula (I), the compound of formula (IV) 1Compounds of formula (I) and amine compounds of formula (VI) (where G is as defined for compounds of formula (I)) can be obtained by activating the carboxylic acid functionality of compounds of formula (IV) to undergo an amide coupling transformation. This is a process that typically occurs by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl) or SOCl, before treating with compounds of formula (IV), preferably at a temperature between 25°C and 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran).

[0065] Alternatively, compounds of formula (II) can be obtained under conditions described in the literature for amide coupling using an amidating coupling reagent such as 1-propanephosphonic acid cyclic anhydride (T3P) in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084. [ka] Scheme 4

[0066] As shown in Schemes 5a, 5b and 5c below, respectively, compounds of formula (I), (III) or (II) as defined in Schemes 1, 2, 3 and 4 above can be converted to compounds of formula (VII), where R1 is as defined for compounds of formula (I)) with a nucleophilic compound of formula (VIII), (IX) or (X) respectively (wherein G is as defined for compounds of formula (I) and X 1 and X 2 is as defined for compounds of formula (III) in Scheme 2, and X 3 can also be prepared by reacting with an electrophilic compound (wherein B is a suitable leaving group, such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2, or B(pinacol)). For relevant examples, see Eur. J. Org. Chem. 2011, 18, 3353; J. Org. Chem. 2009, 74, 7951; Tetrahedron Lett., 2012, 53, 5318. Compounds of formula (VII) are known or commercially available. [ka] Scheme 5a [ka] Scheme 5b [ka] Scheme 5c

[0067] As shown in Scheme 6 below, a compound of formula (VIII) (wherein G is as defined for compounds of formula (I) and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol) can be chlorinated using a chlorinating agent such as POCl3, PCl5, (COCl)2 or SOCl2 in a suitable solvent or solvent mixture (e.g. dichloromethane, dimethylformamide, 2-methyltetrahydrofuran, tetrahydrofuran, diethyl ether, toluene, ethyl acetate), optionally in the presence of dimethylformamide, at a temperature preferably between 0°C and 80°C, more preferably between 25°C and 60°C, to give a compound of formula (X), where G is as defined for compounds of formula (I), and X 3can be obtained by intramolecular cyclization of a compound of formula (VIII) (as defined for compounds of formula (VIII)). See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084. [ka] Scheme 6

[0068] As shown in Scheme 7 below, a compound of formula (X) (wherein G is as defined for compounds of formula (I) and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol), a compound of formula (IX) 3 is as defined for compounds of formula (X), and X 1 and X 2 can be obtained by amine deprotection of a compound of formula (III) (as defined for compounds of formula (III) in connection with Scheme 2). Protecting groups can be removed using standard techniques (see Greene's Protective Groups in Organic Synthesis, 4th Ed., Wiley-Interscience). [ka] Scheme 7

[0069] As shown in Scheme 8 below, compounds of formula (IX) (wherein G is as defined for compounds of formula (I) and X 1 and X 2 is as defined for compounds of formula (III) in connection with Scheme 2, and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol) can be prepared by reacting a compound of formula (XI) 3is as defined for compounds of formula (IX) and compounds of formula (V) (wherein G is as defined for compounds of formula (I) and X 1 and X 2 Amine compounds of formula (XI) (wherein R is as defined for compounds of formula (III) in connection with Scheme 2) can be obtained by activating the carboxylic acid functionality of compounds of formula (XI) to undergo an amide coupling transformation. This is a process that typically occurs by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl) or SOCl, before treating with compounds of formula (V), preferably at temperatures between 25° C. and 60° C., optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran).

[0070] Alternatively, compounds of formula (IX) can be obtained under conditions described in the literature for amide coupling using an amidating coupling reagent such as 1-propanephosphonic acid cyclic anhydride (T3P) in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084.

[0071] Compounds of formula (V) are known, commercially available, or readily available to those skilled in the art. [ka] Scheme 8

[0072] As shown in Scheme 9, compounds of formula (X) (wherein G is as defined for compounds of formula (I) and X 3is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol) can be prepared by reacting a compound of formula (XI) 3 Compounds of formula (XI) (where G is as defined for compounds of formula (X)) and amine compounds of formula (VI) (where G is as defined for compounds of formula (I)) can be obtained by activating the carboxylic acid functionality of compounds of formula (XI) to undergo an amide coupling transformation. This is a process that typically occurs by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl) or SOCl, before treating with compounds of formula (VI), preferably at a temperature between 25°C and 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, dichloromethane, or tetrahydrofuran).

[0073] Alternatively, compounds of formula (X) can be obtained under conditions described in the literature for amide coupling using an amidating coupling reagent such as 1-propanephosphonic acid cyclic anhydride (T3P) in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084. Compounds of formula (VI) are known or commercially available. [ka] Scheme 9

[0074] As shown in Schemes 10a and 10b below, compounds of formula (I) and III) as defined in Schemes 1, 2 and 3 above can be converted to compounds of formula (XIII) and (XIV) (wherein G is as defined for compounds of formula (I) and X is as defined for compounds of formula (I)) in the presence of a base (e.g., K0-t-Bu, K3PO4, K2CO3, triethylamine or Cs2CO3) in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane or dimethyl sulfoxide) at a temperature between 10°C and 90°C and preferably using a metal catalyst complex (e.g., Cu or Pd). 1 and X 2 is as defined for compounds of formula (III) in connection with Scheme 2) with a nucleophilic compound of formula (XII) 1 is as defined for compounds of formula (I), and X 3 can also be prepared by reacting with an electrophilic compound (wherein B is a suitable leaving group, such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2, or B(pinacol)). For relevant examples, see Eur. J. Org. Chem. 2011, 18, 3353; J. Org. Chem. 2009, 74, 7951; Tetrahedron Lett., 2012, 53, 5318. Compounds of formula (XII) are known or commercially available. [ka] Scheme 10a [ka] Scheme 10b

[0075] As shown in Scheme 11 below, compounds of formula (XIII) (wherein G is as defined for compounds of formula (I)) can be obtained by intramolecular cyclization of compounds of formula (XV) (wherein G is as defined for compounds of formula (I)) using a chlorinating agent, for example, by using POCl, PCl, (COCl), or SOCl in a suitable solvent or mixture of solvents (e.g., dichloromethane, dichloroformamide, 2-methyltetrahydrofuran, tetrahydrofuran, diethyl ether, toluene, ethyl acetate) at a temperature preferably between 0° C. and 80° C., more preferably between 25° C. and 60° C., optionally in the presence of dimethylformamide. See, for example, Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev. 2011, 40, 5084. [ka] Scheme 11

[0076] As shown in Scheme 12 below, a compound of formula (XV) (wherein G is as defined for compounds of formula (I)) can be prepared by reacting a compound of formula (XIV) (wherein G is as defined for compounds of formula (I) and X 1 and X 2 can be obtained by amine deprotection of a compound of formula (III) (as defined for compounds of formula (III) in Scheme 2). Protecting groups can be removed using standard techniques (see Greene's Protective Groups in Organic Synthesis, 4th Ed., Wiley-Interscience). [ka] Scheme 12

[0077] As shown in Scheme 13 below, a compound of formula (XVII) (wherein G is as defined for compounds of formula (I) and X 4 OH or OR 1 and R 1is as defined for compounds of formula (I)) can be prepared by reacting a compound of formula (VI) (wherein G is as defined for compounds of formula (I)) with a compound of formula (XVI) (wherein X 4 OH or OR 1 and R 1 is as defined for compounds of formula (I), and X 5 can be obtained by coupling with a compound of C1-C4 alkoxy, e.g., methoxy or ethoxy. Subsequent cyclization can be achieved using an acid, typically acetic acid, at a temperature of 20°C to 120°C, preferably 80°C to 120°C. For relevant examples, see Heterocycles 2016,92,2166 and WO 2017 / 031325. Compounds of formula (VI) are known or readily available to those skilled in the art. [ka] Scheme 13

[0078] As shown in Scheme 14 below, 4 OH or OR 1 and R 1 is as defined for compounds of formula (I), and X 5 is C1-C4 alkoxy, for example methoxy or ethoxy), can be prepared by reacting a compound of formula (XVIII) with an alkoxide, typically an alkoxide in a corresponding alcohol solution (e.g., sodium methoxide, sodium methoxide or potassium tert-butoxide) or an excess of an alcohol such as methanol or ethanol and an alkali metal at a temperature between -30°C and 20°C.

[0079] Alternatively, the compound of formula (XVI) can be obtained by hydrolyzing the compound of formula (XVIII) in the presence of an acid, preferably, but not limited to, hydrochloric acid, in a suitable solvent or solvent mixture, such as methanol, ethanol, dichloromethane, or 1,4-dioxane, at a temperature of −30° C. to 40° C. For relevant examples, see WO 2012 / 178015, JP 2014-037370, or Chem. Int. Ed. 2020, 59, 23306. [ka] Scheme 14

[0080] As shown in Scheme 15 below, 1 is as defined for compounds of formula (I), and X 5 is C1-C4 alkoxy, for example methoxy or ethoxy) can be obtained by the compound of formula (XIX) 1 can be prepared by reacting a compound of formula (I) (which is as defined for the compound of formula (I)) in an aqueous solvent or solvent mixture, such as isopropanol or ethanol, optionally in an alkaline medium, at a temperature between 60° C. and 110° C. For relevant examples, see J. Med. Chem. 2012, 55, 10118. [ka] Scheme 15

[0081] As shown in Scheme 15a below, 1 is as defined for compounds of formula (I), the compound of formula (XIX) 1 can be prepared by hydrolysis of a compound of formula (I) (as defined for compounds of formula (I)) in an aqueous solvent mixture of a solvent such as tetrahydrofuran, optionally in alkaline medium, at a temperature between 60° C. and 110° C. For relevant examples, see J. Med. Chem. 2012, 55, 10118. [ka] Scheme 15a

[0082] Formula (XIX) (where R 1 Compounds of formula (XX) (wherein R is as defined for compounds of formula (I)) are known or can be prepared by cleaving a compound of formula (XX) (wherein R is as defined for compounds of formula (I)) as shown in Scheme 16 below. 1 is as defined for compounds of formula (I), and X 7 is chloro, bromo, iodo, or O-trifluoromethanesulfonyl) using a metal source such as XPhos Pd G1 in the presence of a cyanide source such as potassium ferrocyanide, copper cyanide, zinc cyanide, or potassium cyanide and a base (e.g., KOAc) in a suitable solvent or mixture of solvents (e.g., dioxane, water, toluene, tetrahydrofuran, 2-methyl-tetrahydrofuran, xylene) at a temperature of 50°C to 120°C, preferably 80°C to 110°C. For relevant examples, see J. Org. Chem. 2018, 83, 4922 and Org. Let. 2006, 8, 1189. Compounds of formula (XX) are known or readily available to those skilled in the art. [ka] Scheme 16

[0083] As shown in Scheme 17, a compound of formula (XVII) (wherein X 4 OH or OR 1 and R 1 is as defined for compounds of formula (I)) can be prepared by reacting a compound of formula (XXI) (wherein G is as defined for compounds of formula (I) and X 4is as defined for compounds of formula (XVII)) can be obtained by cyclization using an acid, such as acetic acid, neat or in a suitable solvent such as methanol or ethanol at a temperature between 20°C and 75°C, followed by reduction in the presence of a hydride (e.g., sodium cyanoborohydride, sodium borohydride, sodium triacetoxyborohydride or lithium borohydride) in a solvent or mixture of solvents, such as tetrahydrofuran, toluene or methanol. For relevant examples, see WO 2016 / 201168. [ka] Scheme 17

[0084] As shown in Scheme 18, compounds of formula (XXI) (wherein G is as defined for compounds of formula (I) and X 4 OH or OR 1 and R 1 is as defined for compounds of formula (I)) can be prepared by reacting a compound of formula (XXIII) (wherein G is as defined for compounds of formula (I) and X 8 is a leaving group such as chloro, bromo, iodo, mesyl, tosyl, or O-trifluoromethanesulfonyl) with a compound of formula (XXII) 4 OH or OR 1 and R 1is as defined for the compound of formula (I)) at a temperature between 0°C and 110°C, more preferably between 20°C and 80°C, in a suitable solvent or mixture of solvents, such as benzene, toluene, tetrahydrofuran, chloroform, acetonitrile or 2-methyl-tetrahydrofuran, optionally in the presence of a base (e.g., pyridine, triethylamine, potassium carbonate, sodium carbonate). For relevant examples, see J.Med.Chem.2011,54,8407, WO 2002 / 051811 or WO 2010 / 078867. Compounds of formula (XXIII) are known or readily available to those skilled in the art. [ka] Scheme 18

[0085] As shown in Scheme 19 below, 4 OH or OR 1 and R 1 (wherein X is as defined for compounds of formula (I)) can be prepared by reacting compounds of formula (XVIII) with hydroxyamine or a salt thereof, such as a hydrochloride salt, in a suitable solvent or mixture of solvents, such as methanol, ethanol, 2-methyl-2-butanol, water, or 1-butyl-3-methylimidazolium acetate, optionally in the presence of a base (e.g., potassium carbonate or sodium carbonate). For relevant examples, see Org. Biomol. Chem. 2014, 12, 8036, WO 2016 / 143655, or WO 2019 / 224743. Compounds of formula (XVIII) are known, commercially available, or readily available to those skilled in the art. Compounds of formula (XXII) may also be known. [ka] Scheme 19

[0086] As shown in Scheme 20, a compound of formula (XXV) (wherein R 1 is as defined for compounds of formula (I), and XX 5 is C1-C4 alkoxy, e.g., methoxy or ethoxy), can be reacted with a base (e.g., KPO-t-Bu, KPO-2) in a suitable solvent or mixture of solvents (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, or dimethyl sulfoxide) at a temperature between 20°C and 110°C and preferably using a metal catalyst complex (e.g., Cu or Pd). 4、 In the presence of KCO, triethylamine or CsCO, a compound of formula (VII) (wherein R 1 is as defined for compounds of formula (I)) with an electrophilic compound of formula (XXIV) 5 is C1-C4 alkoxy, such as methoxy or ethoxy, and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2, or B(pinacol). For relevant examples, see Eur. J. Org. Chem. 2011, 18, 3353; J. Org. Chem. 2009, 74, 7951; Tetrahedron Lett. 2012, 53, 5318; WO 2008 / 110313; and WO 2012 / 136604. Compounds of formula (VII) are known or commercially available.

[0087] Formula (IV) (wherein, R 1 is as defined for compounds of formula (I), the compound of formula (XXV) 5is C1-C4 alkoxy, for example, methoxy or ethoxy), can be obtained by ester hydrolysis using an alkali hydroxide such as lithium hydroxide, sodium hydroxide, potassium hydroxide or barium hydroxide in a suitable solvent or mixture of solvents (e.g., methanol, acetonitrile, ethanol, water, tetrahydrofuran or 2-methyl-tetrahydrofuran) at a temperature between 0°C and 80°C. Alternatively, the ester can be cleaved under acidic conditions, for example, using hydrochloric acid. For relevant examples, see WO 2021 / 086879 or Org. Biomol. Chem. 2015, 13, 7928. [ka] Scheme 20

[0088] As shown in Scheme 21, a compound of formula (XXV) (wherein R 1 is as defined for compounds of formula (I), and X 5 is C1-C4 alkoxy, for example methoxy or ethoxy) can be obtained by the compound of formula (XXXVI) 5 is C1-C4 alkoxy, for example, methoxy or ethoxy) with a nucleophilic compound of formula (XII) 1 is as defined for compounds of formula (I), and X 3is a suitable leaving group such as chloro, bromo, iodo, 3K, B(OH)2, or B(pinacol)) with a metal source (e.g., Cu(OAc)2) in a suitable solvent (e.g., dichloromethane, 1,2-dichloromethane, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, N-methylpyrrolidone, or dimethylacetamide) at a temperature of 40°C to 80°C, preferably in the presence of an oxidizing agent such as O2 or a suitable palladium precatalyst such as RockPhos Pd G3, in the presence of a base (e.g., K3PO4) and a suitable solvent (e.g., dimethyl ether or toluene) at a temperature of 20°C to 80°C. For relevant examples, see Org. Lett. 2003, 5, 1381; Tetrahedron Lett. 1998, 39, 2933; Tetrahedron See Org. Lett. 2003, 44, 3863 and Org. Lett. 2013, 15, 2876. Compounds of formula (XII) are known or commercially available. [ka] Scheme 21

[0089] As shown in Scheme 22 below, 9 Compounds of formula (XXVIII) (wherein X is OH or halogen) can be obtained by hydrolysis of compounds of formula (XXVIII) in a similar manner as described for the conversion of compounds of formula (XXVI) to compounds of formula (XXV) in Scheme 21. 5 is C1-C4 alkoxy, such as methoxy or ethoxy, and X 9 is OH or a halogen) can be converted to a compound of formula (XXVIII) (wherein X is OH or a halogen) via an oxidation method using a suitable oxidizing agent, such as KMnO or a cobalt (II) salt and trihydroxyisocyanuric acid (THICA), in a suitable solvent, such as acetic acid, at a temperature between 25°C and 200°C. 9is OH or a halogen). For relevant examples, see Can. J. Chem. 1978, 56, 1273 and WO 2021 / 160470. Compounds of formula (XXVII) are known or can be prepared as described in Bulletin de la Société Chimique de France 1972, 8, 3198. [ka] Scheme 22

[0090] As shown in Scheme 23, a compound of formula (XXV) (wherein X 5 Compounds of formula (XXXI) (wherein C1-C4 alkoxy, e.g., methoxy or ethoxy) can be obtained from compounds of formula (XXXI) via an oxidation method using a suitable oxidizing agent, e.g., KMnO4 or a suitable cobalt(II) salt, and trihydroxyisocyanuric acid (THICA), in a suitable solvent (e.g., acetic acid) at temperatures between 25°C and 200°C. For relevant examples, see Can. J. Chem. 1978, 56, 1273 and WO 2021 / 160470. Compounds of formula (XXV) are known or can be prepared as described in Bulletin de la Société Chimique de France 1972, 8, 3198.

[0091] Furthermore, compounds of formula (XXXI) can be prepared by the reaction of a base (e.g., KOH-t-Bu, KPO) in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethyl sulfoxide) at a temperature between 25°C and 120°C and optionally using a metal catalyst and a ligand complex (e.g., CuI, N,N-dimethylglycine). 4、 In the presence of KCO, triethylamine or CsCO, a compound of formula (VII) (wherein R 1 is as defined for compounds of formula (I)) with a nucleophilic compound of formula (XXX) (wherein X 3can be prepared by reacting with an electrophilic compound of formula (XXX) (wherein B is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2, or B(pinacol)). For relevant examples, see Eur. J. Org. Chem. 2011, 18, 3353; J. Org. Chem. 2009, 74, 7951; Tetrahedron Lett. 2012, 53, 5318; WO 2008 / 110313; and WO 2012 / 136604. Compounds of formula (XXX) are known or commercially available. [ka] Scheme 23

[0092] As shown in Scheme 24, a compound of formula (XXV) (wherein R 1 is as defined for compounds of formula (I), and X 5 is OH or C1-C4 alkoxy, for example methoxy or methoxy), can be reacted with a compound of formula (XX), (wherein R is OH or C1-C4 alkoxy, for example methoxy or methoxy), in the presence of an organic base, for example triethylamine or diisopropylethylamine, and in the presence of a suitable solvent (for example methanol or ethanol), typically at a pressure of 1 to 50 bar, preferably 5 to 15 bar, using a metal source such as XPhos Pd G1 in a pressure vessel, typically a stainless steel autoclave, filled with carbon monoxide, at a temperature of 20°C to 130°C, preferably 70°C to 110°C. 1 is as defined for compounds of formula (I), and X 7 is chloro, bromo, iodo or trifluoromethanesulfonyl-O-). For related examples, see J. Med. Chem. 2014, 57, 2692 and Adv. Synth. Catal. 2006, 348, 1255. [ka] Scheme 24

[0093] Alternatively, as shown in Scheme 25 below, a compound of formula (IV) (wherein R1 is as defined for compounds of formula (I), can be prepared by reacting a compound of formula (XXXII) (wherein R 1 is as defined for compounds of formula (I), and X 10 The compound (wherein Br is chloro, bromo, or iodo) can also be obtained by reacting the compound with a lithium reagent (e.g., n-butyllithium, sec-butyllithium, tert-butyllithium, or lithium diisopropylamine) followed by the addition of carbon dioxide. For related examples, see J.Am.Chem.Soc. 2018, 140, 9140 and J.Am.Chem.Soc. 2021, 143, 1539. [ka] Scheme 25

[0094] As shown in Scheme 26 below, 1 is as defined for compounds of formula (I), and X 10 Compounds of formula (XXXIII) (wherein R is chloro, bromo or iodo) are known or can be prepared by the method of 1 is as defined for compounds of formula (I)) with an electrophilic halogen reagent such as bromine, dibromohydantoin, N-bromo- or N-chloro-succinimide, and optionally a base, typically lithium diisopropylamine or n-butyllithium, in a suitable solvent (e.g., chloroform, 2-methyltetrahydrofuran, or dimethylformamide) at a temperature of −78° C. to 10° C. For relevant examples, see Tetrahedron Lett. 2003, 44, 823; J. Am. Chem. Soc. 2010, 132, 8858; and Synthesis 2005, 16, 2782. [ka] Scheme 26

[0095] As shown in Scheme 27 below, a compound of formula (IV), wherein R 1 is as defined for compounds of formula (I)) can be converted into a compound of formula (XXXIV) (wherein R 1 can also be prepared by reacting a compound of formula (XXXIV) (as defined for compounds of formula (I)) with a base, typically lithium diisopropylamine or n-butyllithium, followed by the addition of carbon dioxide. Compounds of formula (XXXIV) are known, commercially available, or readily available to those skilled in the art. For relevant examples, see Bioorg.Med.Chem.2004,12,5579, J.Am.Chem.Soc.2010,132,8858, and Synthesis2005,16,2782. [ka] Scheme 27

[0096] As shown in Scheme 28 below, compounds of formula (V) can be prepared by reacting compounds of formula (XXXV) where X 1 is H and X 2 is a protecting group, or X 1 and X 2 are the same or different protecting groups, or X 1 and X 2 form a protecting group together with the nitrogen to which they are attached, and X 1a is H and X 2a is a protecting group, or X 1a and X 2a are the same or different protecting groups, or X 1a and X 2a form a protecting group together with the nitrogen to which they are attached, and X 2 is X 2aX 1 and X 1a Both of X can be hydrogen. 1 and X 2 and the other X 1a and X 2a However, when they form a protecting group together with the nitrogen to which they are attached, the protecting groups are different. Examples of protecting groups include, for example, tert-butyloxycarbonyl, benzylcarbonyl, 9-fluorenylmethylcarbonyl, trifluoroacetyl, benzyl, triphenylmethyl, benzylidenyl, p-trienesulfonyl, phthalimide, or succinimide.

[0097] The treatment of compounds of formula (XXXV) is carried out with an acid (e.g., hydrochloric acid, trifluoroacetic acid) in any suitable solvent or solvent mixture, such as dichloromethane, tetrahydrofuran, 2-methyltetrahydrofuran, or diethyl ether, at temperatures between 0° C. and 50° C. For relevant examples, see ChemBioChem. 2009, 10, 323 and Org. Process Res. Dev. 2002, 6, 520. Compounds of formula (XXXV) are known or readily available to those skilled in the art. [ka] Scheme 28

[0098] As shown in Scheme 29 below, 8 OH, halogen, OR 1 and R 1 is as defined for compounds of formula (I), and X 9 is halogen, methyl, trifluoromethanesulfonyl-O-, cyano, COOH, or —C(O)C1-C4 alkoxy, and R 2 is as described below) can be prepared by the compound of formula (XXXVII) 8 and X 9is as defined for compounds of formula (XXXVI) and Z is as described below) with a reagent R 2 -X 11 and 2 -X 11 Compounds of formula (XXXVIII) and various substituents R 2 Suitable reaction conditions for Z are as described below.

[0099] For example, a compound of formula (XXXVI) (wherein R 2 is cyano, C1-C6 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 A compound of formula (XXXVII) (wherein Z is chloro, bromo or iodo) can be reacted with a compound of formula (XXXVIII) (wherein R 2 is cyano, C1-C6 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 alkyl, cycloalkyl, phenyl, heteroaryl, or heterocyclyl; X 11 can be prepared by reacting the aryl esters of ...

[0100] Formula (XXXVI) (where R 2 is C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, phenoxy, heteroaryloxy, or C3-C6 cycloalkyloxy), a compound of formula (XXXVII) (wherein Z is a suitable leaving group such as halogen) can be reacted with a compound of formula (XXXVIII) (wherein R 2 is C1-C6 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 alkyl, phenyl, heteroaryl, or C3-C6 cycloalkyl; X 11 is selected from —OH, NH, SH, or C1-C4 alkylamino) with a suitable nucleophilic compound such as NaH, KO-t-Bu, KPO 4、 They can be prepared by treatment in the presence of a base such as K2CO3, triethylamine, or Cs2CO3 in the presence of an additional solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, or dimethyl sulfoxide) at temperatures between 25°C and reflux. For related examples, see F. Terrier, Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim, 2013.

[0101] Formula (XXXVI) (where R 2 is C1-C4-alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 fluoroalkoxy or C3-C6 cycloalkyloxy) can be obtained from a compound of formula (XXXVII) (wherein Z is OH or SH) by the synthesis of C1-C6 alkyl halide, C3-C5 alkenyl halide, C3-C5 alkynyl halide, C1-C3 alkoxy C2-C3 alkyl, C3-C5 alkenyl, C3-C5 alkynyl halide, C1-C3 alkoxy C2-C3 alkyl halide, C3-C6 cycloalkyl halide and C3-C6 cycloalkyl C 1-2It is readily accessible via known conditions described in the literature using suitable alkaline reagents such as alkyl halides or reagents such as ClF2COOH and Me2SO4. [ka] Scheme 29

[0102] As shown in Scheme 30 below, 7 is chloro, bromo or iodo) can be represented by the formula (XL) 7 is similarly selected from chloro, bromo and iodo) with a cyanide salt such as sodium cyanide or potassium cyanide, optionally in the presence of a copper salt (e.g., copper cyanide), in a suitable solvent or solvent mixture (e.g., dimethylformamide, tetrahydrofuran, 2-methyl-tetrahydrofuran) at a temperature of 50° C. to 120° C., preferably 80° C. to 100° C. For relevant examples, see WO 1995 / 07264. [ka] Scheme 30

[0103] As shown in Scheme 31 below, 7 is chloro, bromo or iodo) can be represented by the formula (XLII) 7 is similarly selected from chloro, bromo, and iodo) with methylmagnesium halide (wherein halide is bromide or chloride), optionally in the presence of a copper salt (e.g., copper iodide, copper cyanide, copper chloride, copper acetate), in a suitable solvent or solvent mixture (e.g., diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl-tetrahydrofuran, tert-butyl methyl ether) at a temperature of 20°C to 10°C. For relevant examples, see WO 1995 / 07264. [ka] Scheme 31

[0104] As shown in Scheme 32 below, 8 OH, OR 1 or halogen, R 1 is as defined for compounds of formula (I), and R 2 is as described below) can be obtained by the compound of formula (XLIV) 8 and R 1 is as defined for compounds of formula (XLIII) and Z is as described below) with a reagent R 2 -X 11 It is prepared by reacting with the compound of formula R 2 -X 11 Compounds of formula (XLV) and various substituents R 2 Suitable reaction conditions for Z are as described below.

[0105] For example, a compound represented by formula (XLIII) (wherein R 2 is cyano, C1-C6 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 alkyl, cycloalkyl, phenyl, heteroaryl, or heterocyclyl; X 8 is generally as defined above for compounds of formula (XLIII)), can be prepared by reacting a compound of formula (XLIV) (wherein Z is chloro, bromo or iodo) with a compound of formula (XLV) (wherein R 2 is cyano, C1-C6 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 alkyl, cycloalkyl, phenyl, heteroaryl, or heterocyclyl; X 11can be prepared by reacting the aryl group with a suitable cross-coupling reagent, preferably a metal, metalloid (e.g., Zn(CN), cyclopropylMgBr, MeZnCl, AlMe), or organometalloid (e.g., trimethylboroxine) reagent, in the presence of a suitable metal (e.g., CuBr) or catalyst complex (e.g., 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride), optionally in the presence of a base (e.g., KCO), in an inert solvent such as toluene or 2-methyltetrahydrofuran at a temperature between 25°C and reflux. See, for example, J. Org. Chem. 1987, 52, 3847; WO 2006 / 045514; WO 2004 / 080998.

[0106] Formula (XLIII) (wherein, R 2 is C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, phenoxy, heteroaryloxy or C3-C6 cycloalkyloxy) can be obtained by reacting a compound of formula (XLIV) (wherein Z is a suitable leaving group such as halogen) with a compound of formula (XLV) (wherein R 2 is C1-C6 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C3 alkoxy, C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC 1-2 alkyl, phenyl, heteroaryl, or C3-C6 cycloalkyl; X 11 is —OH, NH, SH, or C1-C4 alkylamino) with a suitable nucleophilic compound such as NaH, KO-t-Bu, KPO 4、 They are prepared by treatment in the presence of a base such as K2CO3, triethylamine, or Cs2CO3, optionally in the presence of an additional solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethyl sulfoxide) at temperatures between 25°C and reflux. For related examples, see F. Terrier, Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim, 2013.

[0107] Furthermore, the compound represented by formula (XLIII) (wherein R 2 is C1-C4-alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 fluoroalkoxy or C3-C6 cycloalkyloxy) can be obtained by converting a compound of formula (XLIV) (wherein Z is OH or SH) into a compound of formula (XLV) (wherein R 2 is C1-C6 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C3 alkoxy C2-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-2 alkyl, phenyl, heteroaryl or C3-C6 cycloalkyl, and X 11 is readily obtained via known conditions described in the literature using a suitable alkaline reagent (wherein chloro, bromo, iodo, trifluoromethanesulfonyl-O- and methanesulfonyl-O- are suitable leaving groups such as chloro, bromo, iodo, trifluoromethanesulfonyl-O- and methanesulfonyl-O-) or known reagents such as ClF2COOH and Me2SO4. [ka] Scheme 32

[0108] Depending on the reaction conditions and the choice of starting materials suitable in each case, it may, for example, only be possible to replace one substituent with another substituent according to the invention in one reaction step, or several substituents may be replaced with other substituents according to the invention in the same reaction step.

[0109] Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) can be obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or a suitable ion exchange reagent. All other compounds mentioned in Schemes 1 to 16 can be easily prepared by one skilled in the art or are commercially available.

[0110] Salts of compounds of formula (I) can be converted into the free compounds (I) in a conventional manner, for example, acid addition salts can be converted by treatment with a suitable basic compound or a suitable ion exchange reagent, and salts with bases can be converted, for example, by treatment with a suitable acid or a suitable ion exchange reagent.

[0111] Salts of compounds of formula (I) may be converted into other salts of compounds of formula (I) in a manner known per se, for example by converting an acid addition salt into another acid addition salt, for example by treating a salt of an inorganic acid, such as hydrochloric acid, with a suitable metal salt, such as the sodium, barium or silver salt of the acid, for example silver acetate, in a suitable solvent, i.e. in which the inorganic salt formed, for example silver chloride, is insoluble and therefore precipitates from the reaction mixture.

[0112] Depending on the procedure or reaction conditions, compounds of formula (I) that have the property of forming salts can be obtained in free form or in salt form.

[0113] The compounds of formula (I) and, where appropriate, their tautomers, in each case in free or salt form, may, depending on the number, the absolute and relative configuration of asymmetric carbon atoms present in the molecule and / or depending on the configuration of non-aromatic double bonds present in the molecule, exist in the form of one of the possible isomers or as a mixture thereof, in the form of pure isomers, such as, for example, enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, for example racemates or diastereomeric mixtures; the invention relates to all possible isomeric mixtures as well as to pure isomers, and in each case as mentioned above and hereinafter, even if specific stereochemical details are not stated, to be understood in this sense in each case.

[0114] Diastereomeric or racemic mixtures of compounds of formula (I) in free or salt form, which may be obtained depending on the starting materials and procedures selected, can be separated into pure diastereomers or racemates on the basis of the physicochemical differences of the components by known methods, such as fractional crystallization, distillation and / or chromatography.

[0115] Enantiomeric mixtures, such as racemates, obtainable in a similar manner can be resolved into their optical antipodes by known methods, such as recrystallization from optically active solvents, chromatography on chiral adsorbents, for example by high-performance liquid chromatography (HPLC) on acetylcellulose, by the use of suitable microorganisms, cleavage with specific immobilized enzymes, through the formation of inclusion compounds, for example using chiral crown ethers which form complexes with only one enantiomer, or conversion of diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, such as a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixture thus obtainable, for example by fractional crystallization based on their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example a basic agent.

[0116] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomeric mixture, but also by generally known diastereoselective or enantioselective synthetic methods, e.g., by carrying out the process according to the invention using starting materials with the appropriate stereochemistry.

[0117] If the biological activity of the individual components differs, it may be advantageous to isolate or synthesize isomers, such as enantiomers or diastereomers, or isomeric mixtures, such as enantiomeric or diastereomeric mixtures, which are in each case more biologically effective.

[0118] For example, compounds with two or more asymmetric carbon atoms may exist in diastereomeric forms, which may optionally be optically separated on a chiral column, for example using supercritical fluid chromatography (SFC). Such diastereomers may exhibit different fungicidal activity profiles, but all isomers and diastereomers form part of the present invention.

[0119] The compounds of formula (I) and, where appropriate, their tautomers may each be available in free form or in salt form, where appropriate also in the form of a hydrate, and / or may include other solvents, such as those that may have been used for the crystallization of compounds present in solid form.

[0120] As stated above, it has now surprisingly been found that the compounds of formula (I) of the present invention have a very advantageous level of biological activity for practical use in protecting plants from diseases caused by fungi.

[0121] The compounds of formula (I) can be used, for example, in the agricultural sector and related fields of use as active ingredients for controlling plant pests or against non-living organisms for the control of damaging microorganisms or organisms potentially harmful to humans. The novel compounds are distinguished by their excellent activity at low application rates, their well-tolerated nature, and their environmental safety. They have very useful curative, preventive, and systemic properties and can be used to protect a large number of cultivated plants. The compounds of formula (I) can also be used to suppress or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various crops of useful plants, while simultaneously protecting later-growing parts of these plants from, for example, phytopathogenic microorganisms.

[0122] The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and / or harvested food crops that are susceptible to attack by microorganisms by treating the plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound of formula (I) is applied to the plant, a part thereof or its habitat.

[0123] The compound of formula (I) can also be used as a fungicide. As used herein, the term "fungicide" refers to a compound that controls, modifies, or prevents the growth of fungi. When the term "fungicidally effective amount" is used, it refers to the amount of such a compound or a combination of such compounds that can affect the growth of fungi. Control or modification effect includes any deviation from natural occurrence, such as killing, delaying, etc., and prevention includes forming a barrier or other defense in or on a plant to prevent fungal infection.

[0124] To protect against fungal infections and phytopathogenic fungi occurring in the soil, the compounds of formula (I) may also be used as dressings for treating plant propagation material, such as seeds of fruits, tubers, or grains, or plant cuttings. The propagation material can be treated with a composition containing a compound of formula (I) before planting. For example, seeds can be dressed before sowing. The active compound of formula (I) can also be applied (coated) to grains by impregnating the seeds with a liquid formulation or coating the seeds with a solid formulation. When the propagation material is planted, the composition can also be applied to the planting site, for example, to the sowing furrow during sowing. The present invention also relates to a method for treating such plant propagation material and to the plant propagation material treated in this way.

[0125] Furthermore, the compounds of formula (I) can be used to control fungi in relevant fields, for example in the protection of industrial materials, including wood and wood-related industrial products, food storage, hygiene control.

[0126] In addition, the present invention may be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0127] The compounds of formula (I) are effective against, for example, fungi and fungal vectors of diseases, as well as plant pathogenic bacteria and viruses, such as, for example:Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. lactucae, B. dothidea, and B. obtusa; Botrytis spp. including B. cinerea; Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis; Cephaloascus fragrans; Ceratocystis spp. spp.), Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., C. musae, C.Colletotrichum spp. including Colletotrichum musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa rata Fusarium spp., including F. lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, and Glomerella cingulate. cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum), Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma pisae, piceae, Paracoccidioides spp., Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus ignialus igniarus, Phialophora spp., Phoma spp., Phytophthora spp. including Phomopsis viticola and P. infestans, Plasmopara spp. including P. halstedii and P. viticola), Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudoperonospora spp. including Pseudoperonospora spp. Puccinia spp. including P. tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus alitus arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., S. nodorum, Septoria spp. including S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp. Trichoderma spp., including T. harzianum, T. pseudokoningii, and T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp., including V. inaequalis, Verticillium spp., and Xanthomonas spp.

[0128] The compounds of formula (I) may be used, for example, in turf, ornamental plants such as flowers, shrubs, broad-leaved or evergreen trees such as conifers, and for trunk injections, pest control, and the like.

[0129] Target crops and / or useful plants to be protected within the scope of the present invention typically include berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar beet and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus fruits, nectarine, peach, pear and plum; grasses, such as dactylon, strawberry vine, bean grass, Japanese laurel wort, Japanese fescue, rye, St. Augustine grass. and lawn grass; herbs such as basil, borage, chives, coriander, lavender, lovage, peppermint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palms; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as grapes.

[0130] The term "useful plants" should also be understood to include useful plants that have been rendered tolerant to herbicides or classes of herbicides such as bromoxynil (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors, etc.) as a result of conventional breeding or genetic engineering methods. Crops that have been rendered tolerant to imidazolinones, such as imazamox, by conventional methods of breeding (mutagenesis) include, for example, Clearfield® summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0131] It should be understood that the term "useful plants" also includes useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0132] Examples of such plants are YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Root-Feeding Nematode® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing a CryIA(b) and a CryIIIB(b1) toxin); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (a corn root-boring nematode trait), and Protecta®.

[0133] It should be understood that the term "crop plant" also includes crop plants that have been transformed using recombinant DNA techniques to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0134] Toxins that can be expressed by the transformed plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from Photorhabdus luminescens, Xenorhabdus nematophilus, e.g., Photorhabdus spp. or Xenorhabdus spp. insecticidal proteins of nematode-symbiotic bacteria such as nematode toxins (e.g., scorpion toxins, spider toxins, vespid toxins, and other insect-specific neurotoxins); toxins produced by fungi such as streptomyces toxins, plant lectins such as pea lectin, barley lectin, or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ricin, corn-RIP, Ab ribosome-inactivating proteins (RIPs) such as rin, rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0135] Furthermore, in the context of the present invention, it is understood that delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, are also particularly hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins in a new way (see, for example, WO 02 / 15701). For example, truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0136] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0137] The process for preparing such transgenic plants is generally known to those skilled in the art and is described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0138] The toxins contained in the transgenic plants confer resistance to harmful insects on the plants, which can be of any taxonomic group of insects, but are particularly commonly found in beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0139] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, some of which are commercially available. Examples of such plants include YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0140] Further examples of such transgenic crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically modified maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also confers tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. This genetically modified maize (Zea mays) is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt176 maize also transgenicly expresses the enzyme PAT, conferring tolerance to the herbicide glufosinate-ammonium. 3. MIR604 corn, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03 / 018810. 4. MON 863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. IPC 531 cotton, registration number C / ES / 96 / 02. 6. 1507 corn, registered under the number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. This corn is genetically modified for the expression of the Cry1F protein for resistance to certain Lepidoptera insects and the PAT protein for resistance to the herbicide glufosinate ammonium. 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This conventional hybrid maize variety is a cross between the genetically modified varieties NK603 and MON 810. NK603 x MON810 maize transgenicly expresses the CP4 EPSPS protein from Agrobacterium sp. strain CP4, which confers resistance to the Roundup® herbicide (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0141] The compounds of formula (I) may be used to control or prevent plant pathogenic diseases caused by plant pathogenic fungi, such as Botrytis cinerea in particular for members of the Rosaceae, Vitaceae, Solanaceae, Cucurbitaceae and Fabaceae families, Glomerella lagenarium in members of the Cucurbitaceae family, and Blumeria graminis in members of the Poaceae family, such as wheat.

[0142] As used herein, the term "habitat" means a field in or on which plants are growing or in which seeds of cultivated plants are sown or in whose soil seeds will be sown. It includes the soil, seeds and seedlings, and established vegetation.

[0143] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0144] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, and vegetative parts, such as cuttings or tubers (e.g., potatoes), which can be used for their propagation. Examples may include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and plant parts. Mention may also be made of germinated plants and seedlings that are transplanted after germination or emergence from the soil. These seedlings may be protected by a total or partial immersion treatment before transplanting. Preferably, "plant propagation material" is understood to refer to seeds.

[0145] The compounds of formula (I) can be used in their original form or, preferably, together with adjuvants conventionally used in the field of formulation. For this purpose, they can be formulated in a known manner into emulsifiable concentrates, coatable pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusting powders, granules, and also encapsulated in polymeric materials. The application method, such as spraying, spraying, dusting, granulation, coating, or pouring, as well as the type of composition, are selected according to the intended purpose and the prevailing circumstances. The composition can also contain further adjuvants, such as stabilizers, antifoaming agents, viscosity modifiers, binders, or tackifiers, as well as fertilizers, sources of micronutrients, or other formulations for achieving special effects.

[0146] Suitable carriers and adjuvants, for example for agricultural applications, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0147] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents and may further contain wetting agents, as well as anti-foaming and crystal growth inhibitors to enhance activity. When used, these concentrates are diluted with water and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0148] Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient held in a solid matrix. Typical solid matrices include fuller's earth, kaolin clay, silica, and other readily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersing agents, or emulsifying agents.

[0149] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may also contain a liquid carrier such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquid and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0150] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area where treatment is required. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations usually contain 5% to 25% of the active ingredient, which may include surfactants such as high-boiling aromatic naphtha, kerosene, and other petroleum fractions, or vegetable oils, and / or adhesives such as dextrin, glue, or synthetic resins.

[0151] Dustable powders are free-flowing mixtures of the active ingredient and finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0152] Microcapsules are typically droplets or granules of an active ingredient enclosed in an inert, porous shell that allows the encapsulated material to be released into the environment at a controlled rate. The encapsulated droplets are typically 1 to 50 microns in diameter. The encapsulated liquid typically constitutes 50 to 95% of the capsule's weight and may contain solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule, retaining the active species in liquid form within the pores of the granule. Granules typically range in diameter from 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters. Granules are formed by extrusion, agglomeration, or prilling, or are naturally occurring. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0153] Other useful formulations for pesticide applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, and other organic solvents. Pressurized sprayers can also be used, in which the active ingredient is dispersed in finely divided form as a result of evaporation of the low-boiling dispersant solvent carrier.

[0154] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0155] Liquid carriers that can be used include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl 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, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octane Examples of solvents include octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, high molecular weight alcohols such as hexanol and octanol, ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. Generally, the carrier for diluting concentrates is water.

[0156] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferritic clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0157] A wide variety of surfactants are advantageously used in both the liquid and solid compositions, especially those designed to be diluted with a carrier before application. When used, these agents typically comprise from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic, or polymeric in nature and may be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzene sulfonate; alkylphenol-alkylene oxide adducts such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonate salts such as sodium dibutylnaphthalene sulfonate, dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0158] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, sunscreens, compatibilizers, defoamers, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0159] In addition, other biocidal active ingredients or compositions can be combined with the composition of the present invention, used in the method of the present invention, and applied simultaneously or sequentially with the composition of the present invention.When applied simultaneously, these additional active ingredients can be formulated together with the composition of the present invention or mixed, for example, in a spray tank.These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0160] Pesticides are referred to herein using their common names as known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0161] Additionally, the compositions of the present invention can be applied in conjunction with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0162] The compound of formula (I) is usually used in the form of agrochemical compositions, and can be applied to the planted area or the plants to be treated simultaneously or successively with other compounds.These additional compounds can be, for example, fertilizers or sources of micronutrients or other preparations that affect plant growth.They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, and if necessary, also contain additional carriers, surfactants or application-promoting adjuvants that are commonly used in the technical field of formulation.

[0163] The compounds of formula (I) may be used in the form of compositions for the control against or protection against phytopathogenic microorganisms, containing as active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined herein, in free form or in the form of an agrochemically available salt, and at least one of the adjuvants mentioned above.

[0164] Therefore, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise, in addition to the compound of formula (I), at least one or more pesticide active compounds, for example, additional fungicidal active ingredients.

[0165] The compound of formula (I) may be the sole active ingredient of the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic effects.

[0166] Examples of suitable additional active ingredients include acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercuric fungicides, Included are morpholine fungicides, organophosphorus fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0167] Specific examples of suitable additional active ingredients include petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenyl sulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, alamite, arsenous acid, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate, bromocycline ... Mophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphechlor, carbanolate, carbophenothion, cymiazole, chinomethionate, chlorbeneside, chlordimeform, chlordimeform hydrochloride, chlorphenetole, chlorfenson, chlorphenesulfide, chlorobenzilate, chloromebuform, chloromethiron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerin, closantel, coumaphos, crotamiton , Crotoxyphos, Kufraneb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methyl sulfone, Dichlofluanid, Dichlorvos, Dicrifos, Dienochlor, Dimefox, Zinex, Zinex-diclexin, Dinocap-4, Dinocap-6, Dinocton, Dinopenton, Dinosulfone, Dinotervon, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dof Fenapine, doramectin, endothion, eprinomectin, ethoate methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenthone, fentrifanil, flubenzimine, flucycloxuron, fluentil, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I,Jasmolin II, jodofenphos, lindane, malonoven, mecarbam, mefosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro2-methyl-propyl)5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifururidide, nikkomycin, nitrilacarb, nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfoton, p p'-DdT, parathion, permethrin, fenkapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxur, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pirimitate, quinalphos, quinthiofos, R-1492, phosglycine, rotenone, shladan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflobidazin, tau-fluvalinate, TEPP , Terbam, Tetradifon, Tetrasal, Thiafenox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringensin, Triamiphos, Triatene, Triazophos, Triazuron, Tripenophos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Dichlorn, Dichlorophen, Endothal, Fentin, Hydrated lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Crufomate, Piperazine, Thiophanate , chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodisin, fenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate,Probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus naide, Cryptolaemus montrouzieri GV, Cydia pomonella pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae acridum anisopliae var. acridum), Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and N. leconteilecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema scapterisci, Steinernema spp., Trichogramma spp.), Typhlodromus occidentalis, Verticillium lecanii, afolate, bisadil, busulfan, zimatef, hemel, hempa, metepa, methiotepa, methyl afolate, molzide, penfluron, tepa, thiohempa, thiotepa, trethamine, uredepa, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methyl- Tylhept-2-en-4-ol, (E,Z)-tetradeca-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icos-13-en-10-one, (Z) -tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methylo Cutadec-1-ene, 4-methylnonan-5-ol and 4-methylnonan-5-one, alpha-multistriatin, brevicomin, codrelure, codrumone, curua, disparua, dodec-8-en-1-yl acetate, dodeca-9-en-1-yl acetate, dodeca-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate,. Eugenol, Frontalin, Grandolure, Grandolure I, Grandolure II, Grandolure III, Grandolure IV, Hexalure, Ipsdienol, Ipsenol, Japonilure, Lineatin, Litulure, Lupulure, Medulure, Megatomoic acid, Methyleugenol, Muscalure, Octadeca-2,13-dien-1-yl acetate, Octadeca-3,13-dien-1-yl acetate, Olfuralure, Orictalure, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl acetate, Trimedulure, To Rimedlure A, Trimedlure B1, Trimedlure B2, Trimedlure C, Trancol, 2-(octylthio)ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethyl carboxylate, dimethyl phthalate, ethyl hexanediol, hexamide, methoxine-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2- Imidazolidone, 2-isovalerilindan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxohex-1-enyldimethylcarbamate, acetone, acrylonitrile, aldrin, allosamidin, alixycarb, alpha-ecdysone,Aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, Bartholin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, bipermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sevadine, chlorbicycline, chlordane, chlordecone, chloroform, chloropicrin, chlorfoxime, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, cumitate, cryolite, CS 708, cyanofenphos, cyanophos, cyclitrine, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilor, dimefluthrin, dimethane, dimethrine, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide , EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyrithrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hychincarb, IPSP, isazophos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kerevan, kinoprene, arsenic lead, Leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menazone, mercuric chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methocrotophos, methoprene, methotrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, Mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate, O,O-diethyl O-4-methyl 2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl 2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-Tetrapropyldithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, pH 60-38, fenkapton, phosnichlor, phosphine, phoxim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothione, rafoxanide, resmethrin, rotenone, cadet Phosphorus, ryania, ryanodine, sabadilla, shradan, cevufos, SI-0009, tiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oil, thazimcarb, TDE, tebupirimfos, temephos, telallethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetaphos-3, trichloronat, trimethacarb, tolprocarb, triclopiricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, mepe Fluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-Thiadiazinan-3-yl acetic acid, 6-isopentenylaminopurine, anicifluprine, benclothiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sacharinensis sachalinensis) extract, alpha-chlorohydrin, Antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciliroside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)-ethylpiperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, verbutin, MGK 264, piperonyl butoxide, piprotal, propyl isomers, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, Dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chlorinconazide, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, promethazine Tioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R -metalaxyl, ophlox, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, dichlozolin, mycrozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, fenamistrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxacin Cystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluonide, Bordeaux mixture, copper oxide, copper manate, copper oxine, nitrothal-isopropyl, edifenphos, iprobenfos, phosdifen, tolclofos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil,Cyclobutrifluram, diclocymet, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, fosetylaluminum, hymexazole, iprovalicarb, cyazofamid, metasulfocarb, metrafenone, pencycuron, phthalide, Polyoxin, propamocarb, pyribencarb, proquinazide, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isoflucipram, iso Tianil, dipimethitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-( 2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, koumethoxystrobin (diaxiangjundi), rubenmixianan, dichloroentiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone,2-[2-Fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, inpirfluxam, trolprocarb, mefentrifluconazole, ifentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, but-3-ynyl N-[6-[[(Z)-[ (1-Methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl ]pyrazol-3-yl)oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctrazine, amisulbrom, penflufen, (Z,2E)5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, flurylpicoxamide, fenpicoxamide,Methallylpicoxamide, tebufloquine, ifulfenoquine, quinofumelin, isofetamide, Ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared by the methods described in WO 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared by the methods described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-diphenylmethyl)phenyl]methyl]pyrazole-3-carboxylate methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared by the methods described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared by the methods described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2 -difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4- N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)]phenoxy]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, fenamacril, 5-amino-1,3,4-Thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, flutianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1 -yl)propyl]-3-pyridyl]oxy]benzonitrile, Methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, Fluoxapiproline, Enoxastotobin, Methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoe ate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared by the methods described in WO 2020 / 079111), methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared by the methods described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, cumoxystrobin, chonshengmycin, copper thiodiazole, zinc thiazole, ametotratin, iprodione, seboxylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy ]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(-1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5- chloro-2-methyl-6-(-1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared by the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-methyl-formamidine (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, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl- N-methyl-formamidine (these compounds can be prepared by the methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared by the methods described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3 -fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl] -8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the method described in WO 2017 / 153380);1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, and 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds were prepared by the method described in WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared by the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1, 2,4-Oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one

[0033] N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared by the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); (4-phenoxy) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared by the method described in WO 2011 / 138281); ]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine;N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2018 / 06541 4); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyaminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, Mention may also be made of compounds selected from the group consisting of N-[(Z)-methoxyaminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyaminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428);

[0168] Mixtures of the compounds of formula (I) shown below with the active ingredient are preferred: The abbreviation "TX" means one compound selected from the group consisting of the compounds shown in Tables A-1 to A-13, and compound 1.1 in Table T1 (below). Petroleum + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenous acid + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + TX, benzoic acid Benzil + TX, Bixafen + TX, Brofenvalerate + TX, Bromocycline + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium polysulfide + TX, Camphechlor + TX, Carbanolate + TX, Carbophenothion + TX, Cimiazole + TX, Chinomethionate + TX, Chlorbeside + TX, Chlordimeform + TX, Chlordimeform Hydrochloride + TX, Chlorphenetole + TX, Chlorfenson + TX , Chlorfensulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerin +TX, Closantel +TX, Coumaphos +TX, Crotamiton +TX, Crotoxyphos +TX, Kufraneb +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, Deme Ton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-Diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervon+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX, Endothion+TX,Eprinomectin +TX, Ethoate Methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin Oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxuron +TX, Fluentil +TX, Fluorobenside +TX, FMC1137 +TX, Formetanate +TX, Formetanate Hydrochloride +TX, Formoparanate +TX, Gamma-HCH +TX, Gliodin +TX, Halfe Amprox + TX, Hexadecylcyclopropanecarboxylate + TX, Isocarbophos + TX, Jasmolin I + TX, Jasmolin II + TX, Jodofenphos + TX, Lindane + TX, Malonoben + TX, Mecarbam + TX, Mefosoran + TX, Mesulfen + TX, Methacrifos + TX, Methyl Bromide + TX, Metolcarb + TX, Mexacarbate + TX, Milbemycin Oxime + TX, Mipafox + TX, Monocrotophos + TX, Morphothion + TX, Moxidectin + TX, Naled + TX, 4-Chloro-2-(2-chloro-2- Methyl-propyl)5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, Nifluridide + TX, Nikkomycin + TX, Nitrilacarb + TX, Nitrilacarb 1:1 zinc chloride complex + TX, Omethoate + TX, Oxydeprophos + TX, Oxydisulfoton + TX, pp'-DdT + TX, Parathion + TX, Permethrin + TX, Fenkapton + TX, Phosalone + TX, Phosphorane + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactin + TX, Proclonol + TX, Promacil + TX, Propoxur +TX, Protidathion +TX, Protoate +TX, Pyrethrin I +TX, Pyrethrin II +TX, Pyrethrin +TX, Pyridaphenthion +TX, Pirimitate +TX, Quinalphos +TX, Quinthiofos +TX, R-1492 +TX, Phosglycine +TX, Rotenone +TX, Schladan +TX, Cebufos +TX, Selamectin +TX, Sofamid +TX, SSI-121 +TX, Sulfiram +TX, Sulfuramide +TX, Sulfotep +TX, Sulfur +TX, Diflobidazine +TX, Tau-fluvalinate +TX, TEPP +TX, Thelbam +TX,Tetradifon + TX, Tetrasal + TX, Thiafenox + TX, Thiocarboxim + TX, Thiofanox + TX, Thiometon + TX, Thioquinox + TX, Thuringensin + TX, Triamiphos + TX, Triaten + TX, Triazophos + TX, Triazuron + TX, Trifenofos + TX, Trinactin + TX, Vamidothion +TX, Vaniliprole +TX, Bethoxadin +TX, Copper dioctanoate +TX, Copper sulfate +TX, Sibutrin +TX, Dichlorn +TX, Dichlorophen +TX, Endothal +TX, Fentin +TX, Hydrated lime +TX, Nabam +TX, Quinoclamine +TX, Quinonamide +TX, Simazine +TX, Triphenyltin acetate +TX, Triphenyltin hydroxide +TX, Crufomate +TX, Piperazine +TX, Thiophanate +TX, Chloralose +TX, Fenthion +TX, Pyridin-4-amine +TX, Strychnine +TX, 1-Hydroxy-1H-pyridine-2-thione +TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide +TX, Sulfuric acid 8-Hydroxyquinoline + TX, Bronopol + TX, Copper hydroxide + TX, Cresol + TX, Dipyrithione + TX, Dodisin + TX, Fenaminosulf + TX, Formaldehyde + TX, Hydralgafen + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Nickel bis(dimethyldithiocarbamate) + TX, Nitrapyrin + TX, Octilinone + TX, Oxolinic acid + TX, Oxytetracycline + TX, Hydroxyquinoline potassium sulfate + TX, Probenazole + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Tecloftalam + TX, Thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp.) + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus naide + TX, Cryptolaemus montrouzieri GV + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea 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, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp.) + TX, Typhlodromus occidentalis + TX, Verticillium lecanii + TX,. Afolate + TX, Visadyl + TX, Busulfan + TX, Zymacif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl afolate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-Deca-5-en-1-yl acetate and (E)-Deca-5-en-1-ol + TX, (E)-Trideca-4-en-1-yl acetate + TX, (E)-6-Methylhept-2-en-4-ol + TX, (E,Z)-Tetradeca-4,1 0-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-diene -1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, alpha-multistriatin + TX, Brevicomin + TX, Codrelua + TX, Codormon + TX, Curua + TX, Disparleua + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, Dodeca 8,10-dien-1-yl acetate + TX, Dominicalure + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grandolure + TX, Grandolure I + TX, Grandolure II + TX, Grandolure III + TX, Grandolure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX, Japonilure + TX, Lineatin + TX, Littlea + TX, Louplua + TX, Medulure + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalure + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfural + TX, Orictal + TX, Ostramon + TX, Siglua + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedulla + TX, Trimedulla A + TX, Trimedulla B1 + TX, Trimedulla B2 + TX, Trimedulla C + TX, Trancol + TX, 2-(octylthio)ethanol + TX, Butopyronoxyl + TX, Butoxy (Polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyl toluamide + TX, dimethyl carbonate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoxine-butyl + TX, methyl neodecaneamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane and 1,3- Dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-oxo- Silyloxy)ethanol + TX, 2-chlorovinyldiethylphosphate + TX, 2-imidazolidone + TX, 2-isovalerilindane-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-Dimethyl-3-oxohex-1-enyl dimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixicarb + TX, alpha-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis delta-endotoxin +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, bartholin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, beta-cyfluthrin +TX, beta-cypermethrin +TX, bioethanomethrin +TX, bipermethrin +TX, bis(2-chloroethyl) ether +TX, borax +TX, bromfenvinphos +TX, bromo-DDT +TX, bufencarb +TX, butacarb +TX, butathiophos +TX, butonate +TX, calcium arsenate +TX, calcium cyanide +TX, carbon disulfide +TX , carbon tetrachloride +TX, cartap hydrochloride +TX, sevadine +TX, chlorbicycline +TX, chlordane +TX, chlordecone +TX, chloroform +TX, chloropicrin +TX, chlorfoxime +TX, chlorprazophos +TX, cis-resmethrin +TX, cismethrin +TX, clocitrin +TX, copper acetoarsenite +TX, copper arsenate +TX, copper oleate +TX, cumitate +TX, cryolite +TX, CS 708+TX, Cyanofenphos+TX, Cyanophos+TX, Cyclitrine+TX, Sithioate+TX, d-Tetramethrin+TX, DAEP+TX, Dazomet+TX, Decarbofuran+TX, Diamidaphos+TX, Dikapton+TX, Diclofenthion+TX, Dicresyl+TX, Dicyclanil+TX, Dieldrin+TX, Diethyl 5-methylpyrazol-3-ylphosphate+TX, Dilor+TX, Dimefluthrin+TX, Dimethane+TX, Dimethrine+TX, Dimethylvinphos+TX, Dimethylan+TX, Dinoprop+TX, Dinosam+TX, Di Noseb + TX, Diofenolan + TX, Dioxabenzophos + TX, Dicyclophos + TX, DSP + TX, Ecdysterone + TX, EI1642 + TX, EMPC + TX, EPBP + TX, Ethaphos + TX, Ethiofencarb + TX, Ethyl formate + TX, Ethylene dibromide + TX, Ethylene dichloride + TX, Ethylene oxide + TX, EXD + TX, Fenchlorphos + TX, Fenetacarb + TX, Fenitrothion + TX, Fenoxacrim + TX, Fenpyrithrin + TX, Fensulfothion + TX, Fenthion-ethyl + TX, Flucofuron + TX,Fosmetilan + TX, Fospirato + TX, Fostietan + TX, Furathiocarb + TX, Frethrin + TX, Guazatine + TX, Guazatine acetate + TX, Sodium tetrathiocarbonate + TX, Halfenprox + TX, HCH + TX, HEOD + TX, Heptachlor + TX, Heterofos + TX, HHDN + TX, Hydrogen cyanide + TX, Hychincarb + TX, IPSP + TX, Isazophos + TX, Isobenzan + TX, Isodrin + TX, Isofenphos + TX, Isola thionone + TX, isoprothiolane + TX, isoxathion + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, kelevane + TX, kinoprene + TX, arsenic lead + TX, leptophos + TX, lilimphos + TX, ritidathion + TX, m-cumenylmethylcarbamate + TX, magnesium phosphide + TX, magidox + TX, mecarfone + TX, menasone + TX, mercuric chloride + TX, mesulfenphos + TX, metam + TX, metam-potassium + TX , Metam-sodium +TX, Methanesulfonyl fluoride +TX, Metocrotophos +TX, Methoprene +TX, Methotrin +TX, Methoxychlor +TX, Methyl isothiocyanate +TX, Methyl chloroform +TX, Methylene chloride +TX, Methoxadiazone +TX, Mirex +TX, Naphthalophos +TX, Naphthalene +TX, NC-170 +TX, Nicotine +TX, Nicotine sulfate +TX, Nithiazine +TX, Nornicotine +TX, O-5-Dichloro-4-iodophenyl O-Ethyl ethyl phosphonothioate + TX, O,O-Diethyl O-4-methyl 2-oxo-2H-chromen 7-yl phosphorothioate + TX, O,O-Diethyl O-6-methyl 2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-Tetrapropyl dithiopyrophosphate + 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, Phoxim-methyl + TX, Pyrimetaphos + TX, Polychlorodicyclopentadiene isomers + TX, Potassium arsenite + TX, Potassium thiocyanate + TX, Precocene I + TX, Precocene II + TX, Precocene III + TX,Primidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pyrazophos + TX, Pyresmethrin + TX, Quassia + TX, Quinalphos-methyl + TX, Quinothione + TX, Lafoxanide + TX, Resmethrin + TX, Rotenone + TX, Kadetrin + TX, Riania + TX, Ryanodine + TX, Sabadilla + TX, Shradan + TX, Cebufos + TX, SI-0009 + TX, Tiapronil + TX, Sodium arsenite +TX, sodium cyanide +TX, sodium fluoride +TX, sodium hexafluorosilicate +TX, sodium pentachlorophenoxide +TX, sodium selenate +TX, sodium thiocyanate +TX, sulcofuron +TX, sulcofuron-sodium +TX, sulfuryl fluoride +TX, sulprofos +TX, tar oil +TX, tazimcarb +TX, TDE +TX, tebupirimfos +TX, temephos +TX, telallethrin +TX , Tetrachloroethane + TX, Cyclophos + TX, Thiocyclam + TX, Thiocyclam hydrogen oxalate + TX, Thionazine + TX, Thiosultap + TX, Thiosultap-sodium + TX, Tralomethrin + TX, Transpermethrin + TX, Triazamate + TX, Trichlormetaphos 3 + TX, Trichloronat + TX, Trimethacarb + TX, Tolprocarb + TX, Triclopyricarb + TX, Triplene + TX, Veratridine + TX, Veratr Phosphorus + TX, XMC + TX, Zetametrin + TX, Zinc phosphide + TX, Zolaprofos + TX, Meperfluthrin + TX, Tetramethylfluthrin + TX, Bis(tributyltin) oxide + TX, Bromoacetamide + TX, Ferric phosphate + TX, Niclosamide-olamine + TX, Tributyltin oxide + TX, Pyrimorph + TX, Trifenmorph + TX, 1,2-Dibromo-3-chloropropane + TX, 1,3-Dichloropropene + TX, 3,4-Dichloropropane Dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, anicifluprine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenol + TX, zeatin + TX, potassium ethylxanthate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, Reynoutria sacharinensissachalinensis) extract +TX, alpha-chlorohydrin +TX, Antu +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocoumafen +TX, fluoroa Cetoamide + TX, flupropazine + TX, flupropazine hydrochloride + TX, norbormide + TX, fosacetim + TX, phosphorus + TX, pindone + TX, pyrinuron + TX, sciliroside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, 2-(2-butoxyethoxy)-ethyl piperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol and nerolidol + TX, berubutin + TX, MGK264+TX, piperonyl butoxide+TX, piprotal+TX, propyl isomers+TX, S421+TX, sesamex+TX, sesamolin+TX, sulfoxide+TX, anthraquinone+TX, copper naphthenate+TX, copper oxychloride+TX, dicyclopentadiene+TX, thiram+TX, zinc naphthenate+TX, ziram+TX, imanin+TX, ribavirin+TX, chlorinconazide+TX, mercury oxide+TX, thiophanate-methyl+TX, azaconazole+TX, bitertanol+TX, bromuconazole+TX, cyproconazole azole +TX, difenoconazole +TX, diniconazole +TX, epoxiconazole +TX, fenbuconazole +TX, fluquinconazole +TX, flusilazole +TX, flutriafol +TX, furametpyr +TX, hexaconazole +TX, imazalil +TX, imibenconazole +TX, ipconazole +TX, metconazole +TX, myclobutanil +TX, paclobutrazol +TX, pefurazoate +TX, penconazole +TX, prothioconazole +TX, pyrifenox +TX, prochloraz +TX, pro Lopiconazole + TX, pyrisoxazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimate + TX, dimethirimol + TX, ethirimol + TX, dodemorph + TX, fenpropidin + TX, fenpropimorph + TX, spiroxamine + TX, tridemorph + TX, cyprodinil + TX, mepanipyrim + TX X, pyrimethanil + TX, fenpiclonil + TX, fludioxonil + TX, benalaxyl + TX, furalaxyl + TX, metalaxyl + TX, R-metalaxyl + TX, oflox + TX, oxadixyl + TX, carbendazim + TX, debacarb + TX, fuberidazole + TX, thiabendazole + TX, chlozolinate + TX, dichlozolin + TX, mycrozolin + TX, procymidone + TX, vinclozolin + TX, boscalid + TX, carboxin + TX, fenfuram + TX, flutolanil + TX, mepronil + TX, Oxycarboxin +TX, Penthiopyrad +TX, Thifluzamide +TX, Dodine +TX, Iminoctadine +TX, Azoxystrobin +TX, Dimoxystrobin +TX, Enestrobulin +TX, Fenamistrobin +TX, Flufenoxystrobin +TX, Fluoxastrobin +TX, Kresoxim-methyl +TX, Metominostrobin +TX, Trifloxystrobin +TX, Orysastrobin +TX, Picoxystrobin +TX, Pyraclostrobin +TX, Pyrametstrobin +TX, Pyraoxystrobin +TX, Ferbam +TX , mancozeb + TX, maneb + ​​TX, metiram + TX, propineb + ​​TX, zineb + ​​TX, captafol + TX, captan + TX, fluoroimide + TX, folpet + TX, tolylfluonide + TX, Bordeaux mixture + TX, copper oxide + TX, copper manate + TX, copper oxine + TX, nitrothal-isopropyl + TX, edifenphos + TX, iprobenfos + TX, phosdifen + TX, tolclofos-methyl + TX, anilazine + TX, benthiavalicarb + TX, blasticidin-S + TX, chloroneb + ​​TX, chlorothalonil + TX, cyflufe Namid + TX, Cymoxanil + TX, Cyclobutrifluram + TX, Diclocymet + TX, Diclomedine + TX, Dicloran + TX, Diethofencarb + TX, Dimethomorph + TX, Flumorph + TX, Dithianon + TX, Ethaboxam + TX, Etridiazole + TX, Famoxadone + TX, Fenamidone + TX, Fenoxanil + TX, Ferimzone + TX, Fluazinam + TX, Flumethylsulfolim + TX, Fluopicolide + TX, Fluoxythioconazole + TX, Flusulfamide + TX, Fluxapyroxad + TX, Fenhexami do+TX, fosetylaluminum+TX, hymexazole+TX, iprovalicarb+TX, cyazofamid+TX, methasulfocarb+TX, metrafenone+TX, pencycuron+TX, phthalide+TX, polyoxin+TX, propamocarb+TX, pyribencarb+TX, proquinazid+TX, pyroquilon+TX, pyriophenone+TX, quinoxyfen+TX, quintozene+TX, tiadinil+TX, triazoxide+TX, tricyclazole+TX, triforine+TX, validamycin+TX, valifenalate+TX, zoxamide+TX,Mandipropamide + TX, fluveneteram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupyr + TX, pydiflumetofen + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isotianil + TX, dipimethitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2- Chloro-6-fluorophenyl)1,3-dimethyl-1H-pyrazol-5-amine + TX, Fluindapyr + TX, Coumethoxystrobin (Diaxiangjundi) + TX, Rubenmixianan + TX, Dichloroentiazox + TX, Mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, Oxathiapiproline + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, inpirfluxam + TX, trolprocarb + TX, mefentrifluconazole + TX, ifentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX,N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-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]pyrazol-3-yl)oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1- (yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy 2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, methallylpicoxamide + TX, tebufloquin + TX, ifulfenoquine + TX, quinofumelin + TX, isofetamide + TX, ethyl 1-[[4- [[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the methods described in WO 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the methods described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which can be prepared by the methods described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which can be prepared by the methods described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro- phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the method described in WO 2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)]phenoxy]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX Isothamido + TX, Benzothiostrobin + TX, Fenamacril + TX, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram + TX, Flufenoxadiazam + TX, Flutianil + TX, Fluopimomide + TX, Pyrapropoin + TX, Picarburazox + TX, 2-(Difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(Difluoromethyl)-N-((3R)-1,1,3-trimethyl indan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-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-pyrimidinemethanol + TX, fluoxapiproline + TX, enoxastotobin + 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-isopropylpyrazole methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX (these compounds can be prepared by the method described in WO 2020 / 079111), Methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX (these compounds can be prepared by the method described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzo Nitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-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-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Trinexapac + TX, Cumoxystrobin + TX, Chon Shenmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amecttratin + TX, iprodione + TX, seboxylamine + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(- N'-[5-chloro-2-methyl-6-(-1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2015 / 155075);N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-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 methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by the methods described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-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-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl] -8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared by the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds were prepared by the method described in WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared by the methods described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl methyl]propanamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3 -yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3 a compound selected from the group of substances consisting of N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, and N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348, and WO 2017 / 118689;2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the method described in WO 2017 / 029179). 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrolo-1,3,5,7(2H,6H)-tetrone + TX (this compound can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene Carbothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX; N'-[2-chloro-4 -(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared from the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazo (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared from the method described in WO 2018 / 065414);Ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared from the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared from the method described in WO 2018 / 202428);

[0169] A reference in parentheses following an active ingredient, e.g., [3878-19-1], refers to the Chemical Abstracts Registry Number. The aforementioned mixing partners are known. When active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are listed therein under the entry number indicated in parentheses above for the particular compound; for example, the compound "abamectin" is listed under entry number (1). When a specific compound is mentioned above and annotated with "[CCN]," the compound in question is included in the "Compendium of Pesticide Common Names," accessible via the Internet at [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.

[0170] Most of the active ingredients mentioned above are referred to above by so-called "common names", where in each case the relevant "ISO common name" or another "common name" is used. If the name is not a "common name", the nature of the name used instead is given for the particular compound in parentheses. In that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "customary name", "compound name" or "development code" is used, or if none of these names and no "common name" is used, an "alternative name" is utilized. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0171] The active ingredient mixtures of compounds of formula (I) consisting of one of the compounds shown in Tables A-1 to A-13 (below) or compound 1.1 according to Table T1 (below) are preferably in a mixing ratio of 100:1 to 1:6000, in particular 50:1 to 1:50, more particularly 20:1 to 1:20, even more particularly 10:1 to 1:10, very particularly 5:1 to 1:5, with a ratio of 2:1 to 1:2 being particularly preferred, and a ratio of 4:1 to 2:1 being likewise preferred, in particular 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are by weight.

[0172] The mixture may be used in a method for controlling pests, the method comprising the step of applying a composition comprising the mixture to the pest or its environment, excluding methods for treating the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0173] Mixtures comprising a compound shown in Tables A-1 to A-13 (below) or compound 1.1 described in Table T1 (below) and one or more of the active ingredients described above can be applied, for example, in a single "ready-to-mix" form, in combination spray mixtures composed of separate formulations of a single active ingredient, such as "tank mixes," and in combined use of the single active ingredients when applied sequentially, i.e., one after the other within a reasonably short period of time, such as a few hours or days. The order of applying the compound shown in Tables A-1 to A-13 (below) or compound 1.1 described in Table T1 (below) and the active ingredients described above is not essential to the practice of the invention.

[0174] The compounds of the present invention may also be used in combination with an antiparasitic agent. Such antiparasitic agents include compounds selected from the macrocyclic lactone class of compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives, as described in EP 357460, EP 444964, and EP 594291. Additional antiparasitic agents include semisynthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Pat. No. 5,015,630, WO 9,415,944, and WO 9,522,552. Further antiparasitic agents include benzimidazoles, such as albendazole, cambandazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, and parbendazole, as well as other members of this class. Further anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Further anthelmintics include flukicides, such as triclabendazole and clorsulon, and cestocidal drugs, such as praziquantel and epsiprantel.

[0175] The compounds of the present invention may be used in combination with derivatives and analogues of the paraherquamide / markfortin class of anthelmintic agents, as well as anthelmintic oxazolines such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 and German Patent No. 19,520,936.

[0176] The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine anthelmintics described in WO 96 / 15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96 / 11945, WO 93 / 19053, WO 93 / 25543, EP 0626375, EP 0382173, EP 94 / 19334, EP 0382173 and EP 0503538.

[0177] The compounds of the invention may be used in combination with other ectoparasiticides, for example fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0178] The compounds of the present invention may be used in combination with terpene alkaloids such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0179] Other examples of such biologically active compounds that may be used in combination with the compounds of the present invention include, but are not limited to: Organophosphates: Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimphos, famfur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxazophos Thione, malathion, methacrifos, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, paraoxon, parathion, parathion methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos methyl, profenofos, propafos, proethamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion.

[0180] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

[0181] Pyrethroids: acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cicithrin, cyfe Nothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythric acid, flumethrin, fluvalic acid (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalic acid, tefluthrin, tralomethrin, zeta-cypermethrin.

[0182] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentadine, b) Ecdysone agonists: Halofenozide, Methoxyfenozide, Tebufenozide, c) Juvenile hormone-like substances: Pyriproxyfen, Methoprene (including S-methoprene), Fenoxycarb, d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0183] Other antiparasitic agents: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclor, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzin, flufenprox, fluproxifen, Halofenprox, hydramethylnon, IKI-220, Kanemite, NC-196, Niemgard, Nidinolterfuran, Nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, belbutin, Bertalec, YI-5301.

[0184] Biological agents: Bacillus thuringiensis subspecies aizawai, kurstaki, Bacillus thuringiensis delta-endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0185] Fungicides: chlortetracycline, oxytetracycline, streptomycin.

[0186] Other biological agents: enrofloxacin, febantel, penetamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiofur, carprofen, metaflumizone, praziquantel, triclabendazole.

[0187] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for obtaining specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0188] The compositions according to the invention are prepared in a manner known per se, for example by grinding, sieving and / or compressing the solid active ingredient in the absence of auxiliaries and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding. These methods for preparing these compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0189] Another aspect of the present invention relates to the use of a compound of formula (I) or a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicide or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined above in admixture with other fungicides or insecticides as defined above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic microorganisms, e.g. insects or preferably fungal organisms.

[0190] A further aspect of the present invention relates to a method for controlling or preventing infestation of plants, such as useful plants, e.g. crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops or non-living material, by insects or phytopathogenic or spoilage microorganisms or organisms, in particular fungal organisms, that are potentially harmful to humans, which method comprises applying a compound of formula (I) or a preferred individual compound as defined above as active ingredient to the plant, plant parts or its habitat, its propagation material or any part of the non-living material.

[0191] Control or prevention means the reduction of infestation or decay by plant pathogenic microorganisms or organisms potentially harmful to humans, especially fungal organisms, to the extent that an improvement can be demonstrated.

[0192] Preferred methods for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, particularly fungal organisms or insects, include foliar application of a compound of formula (I) or an agrochemical composition containing at least one of the compounds. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compound of formula (I) can also be introduced into the plant through the roots via the soil (systemic action) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, for example, in granular form (soil application). In rice crops, such granules can be applied to flooded rice fields. The compound of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0193] Formulations, e.g. compositions, containing a compound of formula (I) and optionally a solid or liquid auxiliary or a monomer encapsulating the compound of formula (I) may be prepared in known manner, typically by intimately mixing and / or grinding the compounds together with extenders, e.g. solvents, solid carriers and optionally surface-active compounds (surfactants).

[0194] Advantageous application rates are usually 5g to 2kg of active ingredient (ai) per hectare (ha), preferably 10g to 1kg ai / ha, most preferably 20g to 600g ai / ha. When used as a seed drench, a convenient dosage is 10mg to 1g of active substance per kg of seed.

[0195] As used herein, the term "g ai / ha" refers to the application rate expressed in grams [g] of active ingredient [ai] per unit surface [ha]. The unit hectare (symbol ha) is the area of ​​100m square meters (1hm 2 ) square or 10,000 square meters. The hectare is a commonly used unit of area in the metric system.

[0196] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0197] Preferably, the compositions containing the compounds of formula (I) according to the invention are applied preventively, ie before the onset of disease, or curatively, ie after the onset of disease.

[0198] The compositions of the present invention may be in any conventional form, for example in the form of two-part formulations, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowables (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules ( The compositions may be used in the form of emulsions such as emulsions (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil-flowable formulations (OF), oil-liquid formulations (OL), soluble concentrates (SL), ultra-suspensions (SU), ultra-liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0199] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable inert formulations (diluents, solvents, fillers, and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing auxiliary effects). Conventional sustained-release formulations can also be used when efficacy is intended to be sustained over a long period of time. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, can contain surfactants, such as wetting agents and dispersants, as well as other compounds providing auxiliary effects, such as the condensation products of formaldehyde with naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0200] The seed dressing formulation is applied to seeds by a known method using the combination of the present invention and diluents in a suitable seed dressing formulation form, for example, as an aqueous suspension or in the form of a dry powder with good adhesion to seeds.Such seed dressing formulations are known in the art.The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[0201] Typically, formulations contain 0.01 to 90% by weight of active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid inert formulations and adjuvants, where the active agent is composed of at least a compound of formula (I), optionally together with other active agents, more particularly microbicides, preservatives, etc. Concentrate forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application forms of the formulations can contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. Commercially available products are preferably formulated as concentrates, but end users will typically use diluted formulations.

[0202] Commercially available products are preferably formulated as concentrates, although end users will typically utilize diluted formulations.

[0203] The compounds according to the following Tables A-1 to A-13 below can be prepared according to the above method. The following examples illustrate the present invention and are intended to illustrate the invention and are not to be construed as limiting the scope of the invention. 1 is as defined in Tables A-1 to A-13, and R 2 and G are intended to indicate preferred compounds of the formula (as defined in Table G below).

[0204] [Table 3-1]

[0205] [Table 3-2]

[0206] Table A-1: ​​This table lists compounds of formula (I) (wherein R 1 is 3-cyclopropyl-2-fluorophenyl, and the substituent R 2 and G are as defined in Table G above). For example, compound A-1.02 is: [ka]

[0207] Table A-2: This table shows the compounds of formula (I) (wherein R 1 is 3-(trifluoromethyl)phenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-2.01 to A-2.48.

[0208] Table A-3: This table shows the compounds of formula (I) (wherein R 1 is 3-chloro-2-fluorophenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-3.01 to A-3.48.

[0209] Table A-4: This table shows the compounds of formula (I) (wherein R 1 is 3-chlorophenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-4.01 to A-4.48.

[0210] Table A-5: This table lists compounds of formula (I) (wherein R 1 is 5-cyanopyridin-3-yl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-5.01 to A-5.48.

[0211] Table A-6: This table lists compounds of formula (I) (wherein R 1is 3-methylphenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-6.01 to A-6.48.

[0212] Table A-7: This table lists compounds of formula (I) (wherein R 1 is phenyl and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-7.01 to A-7.48.

[0213] Table A-8: This table shows the compounds of formula (I) (wherein R 1 is 3-cyclopropylphenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-8.01 to A-8.48.

[0214] Table A-9: This table shows the compounds of formula (I) (wherein R 1 is 3-(difluoromethyl)phenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-9.01 to A-9.48.

[0215] Table A-10: This table shows the compounds of formula (I) (wherein R 1 is 3-(difluoromethoxy)phenyl, and R 2 is methyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-10.01 to A-10.48.

[0216] Table A-11: This table shows the compounds of formula (I) (wherein R 1 is 3-(trifluoromethyl)-2-fluorophenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-11k.01 to A-11.48.

[0217] Table A-12: This table shows the compounds of formula (I) (wherein R 1 is 3-methoxyphenyl, and the substituent R2 and G are as defined in Table G above), providing 48 compounds A-12.01 to A-12.48.

[0218] Table A-13: This table shows the compounds of formula (I) (wherein R 1 is 2,3-difluorophenyl, and the substituent R 2 and G are as defined in Table G above), providing 48 compounds A-13.01 to A-13.48.

[0219] Also provided are certain intermediate compounds of formula (II-i), (IV-i), (VIII-i), (Xi), (XIII-i), (XX-i), (XXI-i), (XXXVI-i) and (XLIV-i), some of which are novel, for example: - Formula (II-i) (wherein, R 1 , R 2 and G are as defined for compounds of formula (I), e.g., R 1 is as defined in Tables A-1 to A-13 above, and R 2 and G is as defined in Table G above): [ka] - Formula (IV-i) (wherein, R 1 and R 2 is as defined for compounds of formula (I), for example, R 1 is as defined in Tables A-1 to A-13 above, and R 2 is as defined in Table G above): [ka] - Formula (VIII-i) (wherein, R 2 and G are as defined for compounds of formula (I), and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BfK)B(OH) or B(pinacol), for example, R 2and G is as defined in Table G above): [ka] - Formula (Xi) (where R 2 and G are as defined for compounds of formula (I), and X 3 is a suitable leaving group such as fluoro, chloro, bromo, iodo, BfK, B(OH) or B(pinacol), for example, R 2 and G is as defined in Table G above): [ka] - Formula (XIII-i) (wherein, R 2 and G are as defined for compounds of formula (I), e.g., R 2 and G is as defined in Table G above: [ka] - Formula (XX-i) (where R 1 and R 2 is as defined for compounds of formula (I), and X 7 is chloro, bromo, iodo or O-trifluoromethanesulfonyl, for example, R 1 is as defined in Tables A-1 to A-13 above, and R 2 is as defined in Table G above): [ka] - Formula (XXI-i) (where R 2 and G are as defined for compounds of formula (I), and X 4 is OH, halogen or OR 1 and R 1 is as defined for compounds of formula (I), for example, R 1 is as defined in Tables A-1 to A-13 above, and R 2 and G is as defined in Table G above): [ka] - Formula (XXXVI-i) (where R 2 is as defined for compounds of formula (I), and X 8 is OH, halogen or OR 1 and R 1 is as defined for compounds of formula (I), and X 9 is halogen, methyl, trifluoromethanesulfonyl-O-, cyano, COOH or -C(O)C1-C4 alkoxy, for example, R 1 is as defined in Tables A-1 to A-13 above, and R 2 and G is as defined in Table G above): [ka] - a compound of formula (XLIV-i) in which G is as defined for compounds of formula (I), Z is OH, SH, chloro, bromo or iodo, and X 8 is OH, halogen or OR 1 and R 1 is as defined for compounds of formula (I), for example, R 1 is as defined in Tables A-1 to A-13 above, and G is as defined in Table G above: [ka] [Example]

[0220] The examples that follow are intended to illustrate the present invention but are not intended to limit it in any way.

[0221] The compounds of the present invention are distinguishable from known compounds by their high efficacy at low dosages, which can be verified by one skilled in the art using the experimental procedures outlined in the Examples, using low dosages such as 60 ppm, 20 ppm or 2 ppm as appropriate.

[0222] Compounds of formula (I) may have many benefits including, inter alia, advantageous levels of biological activity or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile (including improved crop tolerance), improved physicochemical properties or high biodegradability) for protecting plants against diseases caused by fungi.

[0223] Throughout this specification temperatures are given in degrees Celsius (°C) and "mp" means melting point. LC / MS or LC-MS or LCMS means liquid chromatography mass spectrometry, and a description of the equipment and methods follows.

[0224] Unless otherwise indicated, 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer. Chemical shifts are expressed as TMS( 1 H) and CFCl3 ( 19 F) are expressed in ppm relative to standard. Spectra were measured in deuterated solvents as specified. The following abbreviations are used: s = singlet; br s = broad singlet; d = doublet; br d = broad doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet; q = quartet, quin = quintuplet, sept = septet; m = multiplet.

[0225] Compounds were characterized using one of the following LCMS methods: The characteristic LCMS values ​​obtained for each compound were the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - It was.

[0226] Method B (LCMS): Spectra were recorded on an Agilent Technologies mass spectrometer (6410 Triple Quadrupole Mass Spectrometer) equipped with an electrospray source (positive and negative polarity switch, capillary voltage (kV) 7.00, scan type MS2 scan, fragmentor voltage (V) 120.00, gas temperature (°C) 350, gas flow rate (L / min) 11, nebulizer gas (psi) 40, mass range: 110-650 Da) and an Agilent 1200 Series HPLC: DAD wavelength: 254 nm, column: KINETEX EVO C18, column length: 50 mm, column inner diameter: 4.6 mm, particle size: 2.6 μm, column oven temperature: 40 °C.

[0227] Gradient conditions: Solvent A: Water with 0.1% formic acid:Acetonitrile:95:5 vol / vol Solvent B: Acetonitrile containing 0.1% formic acid

[0228] [Table 4]

[0229] If desired, enantiomerically pure final compounds can be obtained from racemic material, if desired, via standard physical separation techniques such as reverse-phase chiral chromatography or stereoselective synthesis techniques, for example, by using chiral starting materials.

[0230] Method C (LCMS): Spectra were recorded on a Waters mass spectrometer (Acquity QDA mass spectrometer) equipped with an electrospray source (positive and negative polarity switch, capillary voltage (kV) 0.8, cone voltage (V) 25.00, full scan, source temperature (°C) 120, desolvation gas flow rate (L / h) 1000, desolvation temperature (°C) 600, cone gas flow rate (L / h) 50, mass range: 110-850 Da) and HPLC: DAD wavelength range: 230-400 nm, column: Acquity UPLC HSS T3 C18, column length: 30 mm, column inner diameter: 2.1 mm, particle size: 1.8 μm, column oven temperature: 40 °C.

[0231] Gradient conditions: Solvent A: Water with 0.1% formic acid:Acetonitrile:95:5 vol / vol Solvent B: Acetonitrile containing 0.05% formic acid

[0232] [Table 5]

[0233] If desired, enantiomerically pure final compounds can be obtained from racemic material, if desired, via standard physical separation techniques such as reverse-phase chiral chromatography or stereoselective synthesis techniques, for example, by using chiral starting materials.

[0234] Method D (LCMS): Spectra were recorded on a Waters mass spectrometer (Acquity SDQ mass spectrometer) equipped with an electrospray source (positive and negative polarity switch, capillary voltage (kV) 3.0, full scan, cone voltage (V) 41.0, source temperature (°C) 150, desolvation temperature (°C) 500, desolvation temperature (°C) 50, cone gas flow rate (L / h) 50, mass range: 110-800 Da) and HPLC "H" class: DAD wavelength range: 210-400 nm, column: Acquity UPLC HSS T3 C18, column length: 30 mm, column inner diameter: 2.1 mm, particle size: 1.8 μm, column oven temperature: 40 °C.

[0235] Gradient conditions: Solvent A: Water with 0.1% formic acid:Acetonitrile:95:5 vol / vol Solvent B: Acetonitrile containing 0.05% formic acid

[0236] [Table 6]

[0237] If desired, enantiomerically pure final compounds can be obtained from racemic material, if desired, via standard physical separation techniques such as reverse-phase chiral chromatography or stereoselective synthesis techniques, for example, by using chiral starting materials.

[0238] Formulation Examples

[0239] [Table 7]

[0240] This combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to give a wettable powder which is diluted with water to give a suspension of the desired concentration.

[0241] [Table 8]

[0242] This combination is thoroughly mixed with an adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a dust that can be used directly as a seed treatment.

[0243] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (4-5 mol ethylene oxide) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0244] Emulsions of any required dilution that can be used for plant protection are obtained from this concentrate by dilution with water.

[0245] [Table 9]

[0246] Ready-to-use dusting powders are obtained by combining and mixing with a carrier and grinding the mixture in a suitable mill. Such dusting powders can also be used for dry dressing of seeds.

[0247] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0248] This combination is mixed with the adjuvants and ground, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0249] Coated granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0250] This micronized combination is applied uniformly in a mixer to kaolin wetted with polyethylene glycol, thus obtaining coated granules that do not generate dust.

[0251] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0252] The combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect them from microbial infestation.

[0253] Flowable seed treatment Active ingredient 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol + 10-20 moles EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo dye calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0254] The finely ground composite is thoroughly mixed with adjuvants to obtain a flowable formulation, which can be diluted with water to any desired dilution and used directly for seed treatment. By carrying out such dilutions, growing plants as well as plant propagation material can be treated by spraying, pouring, or immersion to protect them from microbial infestation.

[0255] extended-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is achieved. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. This capsule suspension formulation contains 28% active ingredient. The median capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for that purpose.

[0256] Formulation types include emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil-flowable formulations (OF), oil-liquid formulations (OL), soluble concentrates (SL), ultra-suspensions (SU), ultra-liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), water-soluble granules (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0257] Abbreviation: Abbreviations used in the synthetic schemes and preparations ACN Acetonitrile (or MeCN) DCM dichloromethane DMSO dimethyl sulfoxide DMSO-d 6 Deuterated dimethyl sulfoxide Et3N Triethylamine (or TEA) EtOAc ethyl acetate HATU O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate MeOH Methanol THF tetrahydrofuran equiv. equivalent amount h time LC / MS or LC-MS Liquid Chromatography Mass Spectrometry M mole MHz Megahertz min NMR nuclear magnetic resonance ppm parts per million RT room temperature Rt retention time TLC thin layer chromatography

[0258] Preparation Examples The following examples further illustrate, but do not limit, the present invention. Those skilled in the art will immediately recognize appropriate variations from the procedures, both with respect to reactants and reaction conditions and techniques.

[0259] Unless otherwise indicated, 1 H NMR spectra were recorded at 400 MHz. 19 F NMR spectra were recorded at 377 MHz and chemical shifts are reported in ppm. The following abbreviations are used: s = singlet; br s = broad singlet; d = doublet; br d = broad doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet; q = quartet, quin = quintuplet, sept = septet; m = multiplet.

[0260] Throughout this specification, temperatures are given in degrees Celsius (°C). "MP" means melting point. "Rt" means retention time. LC / MS means liquid chromatography mass spectrometry. The LC / MS equipment and methods are as follows:

[0261] Example P1: 3-[5-(3-cyclopropylphenoxy)-3-methyl-pyridazin-4-yl]-5-[(2,4-dichlorophenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (compound 1.1 of Table T1) [ka] a) Preparation of 5-bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one To a mixture of 4,5-dibromopyridazin-3-ol (10 g, 37.4 mmol) and 3-cyclopropylphenol (41.16 mmol) in DMSO (80 mL) in a round-bottom flask, cesium carbonate (93.5 mmol) was added and purged with a stream of nitrogen for 10 minutes. Copper(I) iodide (1.87 mmol) and N,N-dimethylglycine (5.61 mmol) were added, and the reaction mixture was purged with nitrogen for an additional 5 minutes. The reaction mixture was then heated at 110°C for 5 hours. The reaction progress was monitored by TLC and LCMS. The mixture was diluted with EtOAc, quenched with water, and extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by combiflash column chromatography (cyclohexane / EtOAc). The desired fractions were evaporated and the resulting solid was triturated with tert-butyl methyl ether to give pure 5-bromo4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one (6.1 g, 50%) as a white solid. LCMS (Method D): Retention time 1.02 min, m / z 307,309[M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 11.82(br s,1H),7.44(s,1H),7.34(t,1H),7.03(d,1H),6.89(ddd,1H),6.83(t,1H),1.90-1.97(m,1H),1.02-1.08(m,2H),0.71-0.77(m,2H).

[0262] b) Preparation of methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate A 50 mL autoclave vessel was charged with 5-bromo4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one (3.0 g, 9.8 mmol), TEA (20 mmol), MeOH (30 mL), and Pd(dppf)Cl.CHCl (0.98 mmol). The reactor was flushed twice with carbon monoxide and charged to 15 bar. The reaction mass was heated to 90 °C. After 5 h, the reaction mass was cooled to 25 °C, the pressure was released, and the reaction mixture was flushed with nitrogen. The reaction mass was discharged into a clean Erlenmeyer flask. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product, which was washed with pentane to give methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate (1.4 g, 45% yield). LCMS (Method C): Retention time 0.98 min, m / z 287[M+H] + . 1 H NMR(400MHz,CDCl3)δ ppm 11.16-11.34(m,1H),7.56(s,1H),7.32(t,1H),7.01(d,1H),6.90(ddd,1H),6.8 1(t,1H),3.88(s,3H),1.89-1.96(m,1H),0.98-1.11(m,2H),0.68-0.78(m,2H).

[0263] c) Preparation of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate A round-bottom flask was charged with methyl 5-(3-cyclopropylphenoxy)-2-methyl-3-oxo-pyridazine-4-carboxylate (0.8 g, 2.65 mmol), and phosphorus oxychloride (53.11 mmol) was added slowly with stirring. The reaction mixture was heated at 75° C. for 2 hours. The resulting yellow oil was allowed to cool to room temperature, diluted with EtOAc, and slowly poured into water (50 mL) in an Erlenmeyer flask with gentle shaking. The organic layer was separated, washed with water, dried over sodium sulfate, and evaporated to give methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (750 mg, 85% by weight, 78% yield), which was used directly in the next step without purification. LCMS (Method 2): Retention time 1.08 min, m / z 305,307[M+H] + .

[0264] d) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate To a solution of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (1.75 g, 5.74 mmol) in 2Methyl-THF (35 mL) was added potassium carbonate (11.5 mmol), Pd(dppf)Cl CHCl (0.287 mmol), and trimethylboroxine (11.5 mmol). The reaction mixture was stirred at 95 °C for 3 h, and the progress was monitored by TLC and LCMS. The reaction mass was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to give the crude product, which was purified by Combiflash (cyclohexane / EtOAc) to give methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate (1.2 g, 72% yield). LCMS (Method D): Retention time 1.07 min, m / z 285[M+H] + 1H NMR(400MHz,CDCl3)δ ppm 8.71(s,1H),7.33(t,1H),7.02(d,1H),6.89(ddd,1H),6.81(t,1H),3.97(s,3H),2.7 6(s,3H),1.84-2.00(m,1H),0.97-1.09(m,2H),0.69-0.75(m,1H),0.66-0.78(m,1H).

[0265] e) Preparation of 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid To a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate (0.65 g, 2.3 mmol) in THF / water (3:1, 20 mL) was added barium hydroxide octahydrate (6.9 mmol). The mixture was stirred at room temperature for 4 hours. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was acidified with 1N HCl and extracted twice with EtOAc. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-(3, cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid (0.423 g, 65% yield). LCMS (Method C): Retention time 0.18 min, m / z 271[M+H] +

[0266] f) Preparation of 5-(3-cyclopropylphenoxy)-N-[1-[(2,4-dichlorophenyl)methyl]-2-(1,3-dioxoisoindolin-2-yl)oxy-ethyl]-3-methyl-pyridazine-4-carboxamide To a mixture of 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid (300 mg, 1.11 mmol) and 2-[2-amino-3-(2,4-dichlorophenyl)propoxy]isoindoline-1,3-dione 2,2,2-trifluoroacetic acid (1.33 mmol) in dimethylformamide (3 mL) was added N-ethyl-N-isopropyl-propan-2-amine (2.77 mmol) and HATU (1.22 mmol). The resulting pale yellow solution was stirred at room temperature for 16 hours. The progress of the reaction was monitored by LCMS. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated sodium carbonate solution and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude material, which was purified by Combiflash chromatography (cyclohexane / EtOAc) to give 5-(3-cyclopropylphenoxy)-N-[1-[(2,4-dichlorophenyl)methyl]-2-(1,3-dioxoisoindolin-2-yl)oxy-ethyl]-3-methyl-pyridazine-4-carboxamide (0.7 g, 70% mass, 70% yield). LCMS (Method B): Retention time 1.67 min, m / z 617[M+H] + .

[0267] g) Preparation of N-[1-(aminooxymethyl)-2-(2,4-dichlorophenyl)ethyl]-5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxamide To a solution of 5(3-cyclopropylphenoxy)-N-[1-[(2,4-dichlorophenyl)methyl]-2-(1,3-dioxoisoindolin-2-yl)oxy-ethyl]-3-methyl-pyridazine-4-carboxamide (300 mg, 0.485 mmol) in THF (9 mL) was added hydrazine monohydrate (0.971 mmol, 97% by weight), and the mixture was stirred at room temperature for 30 minutes. After that, a solid precipitated. The solid was filtered off, and the filtrate was concentrated to give N-[1-(aminooxymethyl)-2-(2,4-dichlorophenyl)ethyl]-5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxamide (260 mg, 90% by weight, 98% yield), which was used directly in the next step. LCMS (Method C): Retention time 1.21 min, m / z 487,489[M+H] + .

[0268] g) 3-[5-(3-cyclopropylphenoxy)-3-methyl-pyridazin-4-yl]-5-[(2,4-dichlorophenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine To a solution of N-[1-(aminooxymethyl)-2-(2,4-dichlorophenyl)ethyl]-5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxamide (140 mg, 0.287 mmol) in DCM (5 mL) was added phosphorus pentachloride (0.488 mmol). The mixture was stirred at 45 °C for 2 h. The reaction progress was monitored by TLC and LCMS. The reaction mixture was then cooled to room temperature, quenched slowly with a saturated solution of sodium bicarbonate (saturated NaHCO3 solution), diluted with water, and extracted twice with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude material was first purified by Combiflash (cyclohexane / EtOAc) and then by preparative HPLC to give 3-[5-(3-cyclopropylphenoxy)-3-methyl-pyridazin-4-yl]-5-[(2,4-dichlorophenyl)methyl]-5,6-dihydro-4H-1,2,4-oxazine (25 mg, 18%). LCMS (Method C): Retention time 1.25 min, m / z 469, 471 [M+H] + 1 H NMR(400MHz,CDCl3)δ ppm 8.60(s,1H),7.31-7.43(m,2H),7.16(d,1H),7.04(dd,2H),6.83-6.91(m,1H),6.80(s,1H),4.97(br s,1H),3.92-4.05(m,3H),3.03-3.17(m,2H),2.80(s,3H),1.82-2.04(m,1H),0.98-1.11(m,2H),0.68-0.78(m,2H).

[0269] [Table 10-1]

[0270] [Table 10-2]

[0271] Biological Examples and Test Methods The following examples illustrate the present invention: The compounds of the present invention are distinguishable from known compounds by their high efficacy at low doses, which can be verified by one skilled in the art using the experimental procedures outlined in the examples, using low doses such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm as needed.

[0272] Compounds of formula (I) may have many benefits including, inter alia, advantageous levels of biological activity or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile (including improved crop tolerance), improved physicochemical properties or high biodegradability) for protecting plants against diseases caused by fungi.

[0273] General description of the test method Debris or fragments of various plant species are excised from plants grown in a greenhouse. The excised leaf pieces or leaf segments are placed on plain agar medium in a multi-well plate (24-well format). The leaf pieces are sprayed with the test solution either before inoculation (preventive) or after inoculation (curative). The compounds to be tested are prepared as DMSO solutions (up to 10 mg / mL) and diluted to the appropriate concentration with 0.025% Tween 20 immediately before spraying. The inoculated leaf pieces or leaf segments are incubated under defined conditions (temperature, relative humidity, light, etc.) depending on the respective test system. A single assessment of disease level is performed 3 to 14 days after inoculation, depending on the pathogen response system. The percentage of disease control is then calculated by comparing with untreated control leaf pieces or leaf segments.

[0274] Freshly prepared or cryopreserved fungal mycelium fractions or conidial suspensions from fungal broth are mixed directly with the nutrient broth. A DMSO solution of the test compound (up to 10 mg / mL) is diluted 50-fold with 0.025% Tween 20, and 10 μl of this solution is pipetted into a 96-well microtiter plate. The nutrient broth containing the fungal spores / mycelium is then added to obtain the final test compound concentration. The test plate is incubated in the dark at 24°C and 96% relative humidity. Inhibition of fungal growth is measured photometrically after 2-7 days, depending on the pathogen response system, and the percentage of antifungal activity is calculated relative to the untreated control.

[0275] Example B1: Botryotinia fuckeliana (syn. Botrytis cinerea) (grape grey mold) Fungal conidia stored at low temperature are mixed directly into a nutrient liquid medium (Vogels broth). A solution of the test compound (DMSO) is placed in a microtiter plate (96-well format), followed by the addition of nutrient broth containing fungal spores. The test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application.

[0276] The following compounds in Table T1 controlled at least 80% of Botryotinia fuckeliana at 20 ppm when compared to untreated controls under the same conditions that showed widespread disease outbreak: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6.

[0277] Example B2: Glomerella lagenarium (syn. Colletotrichum lagenarium) (anthracnose of Cucurbitaceae plants) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of nutrient broth containing fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds in Table T1 controlled at least 80% of Glomerella lagenarium at 20 ppm when compared to untreated controls under the same conditions, which showed widespread disease development: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6.

[0278] Example B3: Lumeria graminis f.sp. tritici (powder mildew of wheat) Wheat leaf segments (cv. Kanzler) were placed on agar medium in a multiwell plate (24-well type) and sprayed with the formulated test compound diluted in water. One day after application, powdery mildew-infected plants were inoculated onto the leaf disks by shaking them over the test plate. The inoculated leaf disks were incubated in a constant temperature room at 20°C and 60% rh under a 24-h dark period followed by a 12-h light / 12-h dark photoperiod. When the disease damage on the untreated control leaf segments reached an appropriate level (6-8 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0279] The following compounds in Table T1 controlled at least 80% of Glomerella lagenarium at 20 ppm when compared to untreated controls under the same conditions that showed widespread disease infestation: 1.1, 1.2.

Claims

1. Formula (I) 【Chemistry 1】 (In the formula, R 1 is phenyl and is unsubstituted, or - hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me) 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 a single substituent selected from alkylsulfonyl, or - 1, 2 or 3 substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl or R 1 is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2 or 3 heteroatoms each independently selected from N, O and S, provided that no more than 1 O or S is present, said heteroaryl ring being unsubstituted; or - hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me) 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 a single substituent selected from alkylsulfonyl, or one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by R 2 is hydrogen, hydroxyl, nitro, halogen, mercapto, amino, cyano, C 1 ~C 6 Alkyl, C 1 ~C 2 Fluoroalkyl, C 3 ~C 5 Alkenyl, C 3 ~C 5 Alkynyl, C 1 ~C 3 Alkoxy C 2 ~C 3 Alkyl, C 3 ~C 6 Cycloalkyl or C 3 ~C 6 Cycloalkyl C 1-2 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 5 Alkenyloxy, C 3 ~C 5 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 4 Alkylamino, di-C 1 ~C 4 Alkylamino, C 3 ~C 5 Alkenylamino, C 3 ~C 5 Alkynylamino, C 1 ~C 3 Alkylsulfanyl or C 1 ~C 3 alkylsulfonyl, or R 2 is phenyl, phenyl C 1 ~C 2 Alkyl, heteroaryl, heteroaryl C 1 ~C 2 Alkyl, heterocyclyl, heterocyclyl C 1 ~C 2 Alkyl, C 3 ~C 6 cycloalkyl, or C 3 ~C 6 Cycloalkyl C 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring containing 1, 2 or 3 heteroatoms independently selected from N, O and S, provided that no more than 1 O or S is present, and the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring containing 1 or 2 heteroatoms independently selected from N, O and S, provided that no more than 1 O or S is present, and all of the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are unsubstituted; or - hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me) 2 , C 1 ~C 4 Alkyl, C 2 ~C 3 Alkenyl, C 2 ~C 3 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, C 3 ~C 6 Cycloalkyl, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 a single substituent selected from alkylsulfonyl, or one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by G is selected from G-1, G-2, G-3 and G-4; G-1 is phenyl or phenoxy, said phenyl or phenoxy being unsubstituted, or - hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me) 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 a single substituent selected from alkylsulfonyl, or one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by G-2 is a 5- or 6-membered monocyclic heteroaryl or heteroaryloxy, said heteroaryl containing 1, 2, or 3 heteroatoms each independently selected from N, O, and S, provided that no more than 1 O or S is present, and said heteroaryl or heteroaryloxy is unsubstituted; or - hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me) 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 a single substituent selected from alkylsulfonyl, or one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy and cyclopropyl; is replaced by G-3 is a 9- or 10-membered heterobicyclic ring system containing 1, 2, or 3 heteroatoms each independently selected from N, O, and S, with the proviso that no more than 1 O or S is present, said heterobicyclic ring system being saturated, partially unsaturated, or aromatic, said heterobicyclic ring system being unsubstituted or having a single substituent selected from hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me), 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 alkylsulfonyl; G-4 is a 9- or 10-membered carbobicyclic ring system, said carbobicyclic ring system being saturated, partially unsaturated or aromatic, said carbobicyclic ring system being unsubstituted or having a single substituent selected from the group consisting of hydroxyl, nitro, halogen, mercapto, amino, cyano, NHMe, N(Me), 2 , C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 2 Fluoroalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 2 Fluoroalkoxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 4 Alkenyloxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyloxy, C 3 ~C 6 Cycloalkyl C 1 ~C 2 Alkyloxy, C 1 ~C 3 Alkylsulfanyl and C 1 ~C 3 alkylsulfonyl) or an agrochemically acceptable salt, stereoisomer, enantiomer or N-oxide of the compound of formula (I).

2. R 1 is phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is unsubstituted or has one or two substituents, e.g., a single substituent, independently selected hydroxyl, halogen, mercapto, amino, nitro, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, isopropoxy, tert-butoxy, propynoxy, NHMe, N(Me), 2 , methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl, and cyclopropyloxy.

3. R 1 The compound according to claim 1 or 2, wherein is 3-cyclopropyl-2-fluorophenyl, 3-(trifluoromethyl)phenyl, 3-chloro-2-fluorophenyl, 3-chlorophenyl, 5-cyanopyridin-3-yl, 3-methylphenyl, phenyl, 3-cyclopropylphenyl, 3-(difluoromethyl)phenyl, 3-(difluoromethoxy)phenyl, 3-(trifluoromethyl)-2-fluorophenyl, 3-methoxyphenyl, or 2,3-difluorophenyl.

4. R 2 is hydrogen, hydroxyl, halogen, mercapto, amino, cyano, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Fluoroalkyl, C 1 ~C 4 Fluoroalkoxy, or C 3 ~C 4 The compound of any one of claims 1 to 3, which is cycloalkyl.

5. R 2 The compound of any one of claims 1 to 4, wherein is hydrogen, methyl, ethyl, or cyclopropyl.

6. G is phenyl or phenoxy, unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, and cyclopropyl; or 6. The compound of any one of claims 1 to 5, wherein G is pyridine unsubstituted or substituted with one or two substituents each independently selected from hydroxyl, halogen, cyano, methyl, vinyl, ethynyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, prop-2-ynoxy, prop-1-ynoxy, difluoromethoxy, and cyclopropyl.

7. 7. The compound of any one of claims 1 to 6, wherein G is 2,4-dimethylphenyl, 2,4-dichlorophenyl, 4-bromo-2-methylphenyl, 4-bromo-2-chlorophenyl, 2,6-dichloro-3-pyridyl, 4,6-dichloro-3-pyridyl, 3,5-dichloro-2-pyridyl, 3,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-methyl-4-bromophenyl, 2-methyl-4-chlorophenyl, or 2,4-difluorophenyl.

8. A pesticide composition comprising a fungicidally effective amount of a compound according to any one of claims 1 to 7.

9. 10. The composition of claim 8, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

10. 10. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, which comprises applying a fungicidally effective amount of a compound according to any one of claims 1 to 7 or a composition according to claim 8 or 9 to said plants, parts thereof or their habitat.

11. Use of a compound according to any one of claims 1 to 7 as a fungicide.

12. 10. Plant propagation material, such as seeds, comprising, treated with or having attached thereto a compound according to any one of claims 1 to 7 or a composition according to claim 8 or 9.

13. Formula (II-i), (X-i) or (XXI-i): 【Chemistry 2】 (In the formula, X 3 is fluoro, chloro, bromo, iodo, BF 3 K, B(OH) 2 and B (pinacol), X 4 is OH, halogen, or OR 1 and R 1 , R 2 and G are as defined in any one of claims 1 to 7) Compound.

14. Formula (IV-i), (XX-i) or (XXXVI-i): 【Transformation 3】 (In the formula, X 7 is chloro, bromo, iodo or O-trifluoromethanesulfonyl, X 8 is OH, halogen or O-R 1 and X 9 is halogen, methyl, trifluoromethanesulfonyl-O-, cyano, COOH or -C(O)C 1 ~C 4 is alkoxy, and R 1 and R 2 is as defined in any one of claims 1 to 5) Compound.

15. Formula (VIII-i), (XV-i) or (XLIV-i): 【Chemistry 4】 (In the formula, X 3 is fluoro, chloro, bromo, iodo, BF 3 K, B(OH) 2 and B (pinacol), X 8 is OH, halogen, or O-R 1 and Z is OH, SH, chloro, bromo, or iodo, and R 1 , R 2 and G are as defined in any one of claims 1 to 7) Compound.

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