Pyridazine-3-one-4-yl oxadiazines as novel fungicides

Abstract

The present invention relates to pyridazine-3-one-4-yl oxadiazines and to the use thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi. The invention also relates to processes and intermediates for preparing these compounds.

Description

[0001] This invention relates to pyridazine-3-one-4-yloxadiazine and its use in controlling plant pathogenic microorganisms (such as plant pathogenic fungi). The invention also relates to methods and intermediates for preparing these compounds.

[0002] To date, numerous crop protectants have been developed to combat or prevent microbial infection. However, there remains a need to develop new compounds that are effective against a broad spectrum of plant pathogenic microorganisms, such as fungi, while exhibiting low toxicity, high selectivity, or the ability to be applied at low rates, while still effectively controlling pests. It may also be desirable to develop new compounds that prevent the development of resistance.

[0003] This invention provides novel compounds for controlling plant pathogenic microorganisms (such as fungi), which have advantages over known compounds and compositions in at least some of the aforementioned aspects.

[0004] WO2020 / 127780, WO2021 / 245083, WO2021 / 249995, WO2021 / 245087, WO2021 / 255071, WO2023 / 213626, WO2023 / 099445, WO2024 / 089191, WO2024132895 and WO2024 / 132901 disclose oxadiazine compounds with different heterocyclic moieties as fungicides.

[0005] Detailed description Compound of formula (I) This invention relates to compounds of formula (I) and their N-oxides, salts, hydrates, and hydrates of salts and N-oxides: , in R 3 and R 4 Independently hydrogen, fluorine, or C1-C4-alkyl, R 5 It is hydrogen or C1-C4-alkyl. L represents a direct bond or a C1-C4-alkylene bond. in The C1-C4-alkylene group is optionally substituent by one or two L groups. SA replace, L SA It is fluorine. or Two substituents L bonded to the same carbon atom SA Together with the carbon atoms they are attached to, they form cyclopropyl rings or cyclobutyl rings. R6 For C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic, 5 to 14-membered heteroaryl, C3-C 12 -Carbocyclic oxide, C6-C 14 -aryloxy, 5 to 14-membered heteroaryloxy, 3 to 14-membered heterocyclic oxy, C3-C 12 -Carbocyclic thiogroup, C6-C 14 -arylthio, 5 to 14-membered heteroarylthio, 3 to 14-membered heterocyclic thio, C1-C3-alkoxy, C1-C3-haloalkoxy, The C1-C3-alkoxy and C1-C3-haloalkoxy groups are substituted by one substituent selected from the following: C3-C 12 -Carbocyclic group, C6-C 14 -aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl The C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl are optionally surrounded by 1 to 3 R 6S Substituent substitution, Among them, C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic, 5 to 14-membered heteroaryl, C3-C 12 -Carbocyclic oxide, C6-C 14 -aryloxy, 5 to 14-membered heteroaryloxy, 3 to 14-membered heterocyclic oxy, C3-C 12 -Carbocyclic thiogroup, C6-C 14 -Arylthio, 5- to 14-membered heteroarylthio and 3- to 14-membered heterocyclic thio groups are optionally surrounded by 1 to 3 R groups. 6S Substituent substitution, in R 6S Independently selected from: halogen, cyano, nitro, hydroxyl, sulfhydryl, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5 or 6-membered heteroaryl, 3 to 7-membered heterocyclic, -C(=O)(OR 17 ) and -C(=O)N(R 18 )2, The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, C1-C6-alkylthio and C1-C6-haloalkylthio are optionally substituted by one to three independent substituents selected from: fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl. and Among them, C3-C6-cycloalkylthiol, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic groups are optionally substituted by 1 to 3 independent substituents selected from: fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, And, among them R 17 and R 18 Independently hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl. The C1-C4-alkyl or C1-C4-haloalkyl group is optionally substituted by one to three substituents independently selected from the following: fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl. R 7 The group is selected from C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, methylformyl, tert-butylformyl, 2-(dimethylamino)-2-oxo-ethyl, 2-(methylamino)-2-oxo-ethyl, phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thiophene, isoxazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, or triazinyl; wherein any one of the phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thiophene, isoxazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, and triazinyl groups is unsubstituted or is substituented by one or two independently selected from the following groups R. 8 Substitution: halogen, mercapto, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl or C1-C3-alkylsulfonyl; or R 7 For CR12 R 13 R 14 ,in R 12 and R 13 Independently selected from hydrogen or methyl; or R 12 and R 13 Together with the carbon atoms they are attached to, they form cyclopropyl groups; and R 14 Selected from cyano, methylformyl, 2-(dimethylamino)-2-oxo-ethyl or 2-(methylamino)-2-oxo-ethyl; or R 14 The phenyl group is a heteroaryl group selected from pyridinyl, pyrimidinyl, pyridazinyl, triazolyl, thiazolyl, oxazolyl, imidazolyl, thiophene, furanyl, isoxazolyl, oxadiazolyl, and thiadiazolyl, or a heterocyclic group selected from oxadiazyl, aziridine, aziridine, piperidinyl, piperazinyl, tetrahydrofuranyl, tetrahydropyranyl, morpholinyl, and dioxahexacyclic; wherein any one of the phenyl, heteroaryl, and heterocyclic groups is unsubstituted or substituented by one or two independently selected from the following substituents R. 9 Substitution: halogen, mercapto, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C4-alkynyl or C1-C4-alkylsulfonyl; Q represents phenyl, naphthyl, C3-C 10 -Carbocyclic, 5- to 10-membered heterocyclic or 5- to 10-membered heteroaryl Among them, phenyl, naphthyl, C3-C 10 - A carbocyclic group, a 5- to 10-membered heterocyclic group, and a 5- to 10-membered heteroaryl group are optionally substituents Q from 1 to 3 groups. S replace, in Q SIndependently selected from halogen, cyano, nitro, formyl, carboxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, 3- to 7-membered heterocyclic, phenyl, 5- or 6-membered heteroaryl. in The C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylthio, C1-C The 4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, and C1-C4-haloalkylsulfonyl groups are optionally substituted by one to three independent substituents selected from the following: cyano, amino, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and 3 to 7-membered heterocyclic groups. The C3-C6-cycloalkyl, 3- to 7-membered heterocyclic, phenyl, and 5- or 6-membered heteroaryl groups are optionally substituted by 1 to 3 independent substituents selected from the following: fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, and C3-C6-cycloalkyl.

[0006] The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one suitable agricultural adjuvant.

[0007] The present invention also relates to the use of compounds of formula (I) as defined herein or compositions as defined herein for the control of plant pathogenic fungi.

[0008] This invention relates to a method for controlling plant pathogenic fungi, the method comprising the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to a plant, plant part, seed, fruit or soil in which the plant grows.

[0009] The present invention also relates to methods and intermediates for preparing compounds of formula (I).

[0010] Unless otherwise stated, the following definitions apply to the substituents and residues used: As used in this article, the term "halogen" refers to fluorine, chlorine, bromine, or iodine atoms.

[0011] As used in this article, the term "oxo" refers to an oxygen atom bonded to a carbon or sulfur atom via a double bond.

[0012] As used in this article, the term "formyl" refers to -CH (=O).

[0013] As used herein, the term "C1-C6-alkyl" refers to a saturated branched or straight hydrocarbon chain having 1, 2, 3, 4, 5, or 6 carbon atoms. Examples of C1-C6-alkyl include, but are not limited to, methyl, ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, and hexyl. The hydrocarbon chain comprises 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. In particular, the hydrocarbon chain has 1, 2, 3, or 4 carbon atoms (“C1-C4-alkyl”), such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, or tert-butyl.

[0014] As used herein, the term "C1-C6-haloalkyl" means that one or more hydrogen atoms in a C1-C6-alkyl group as defined above are replaced by one or more halogen atoms, which may be the same or different. Examples of C1-C6-haloalkyl groups include, but are not limited to, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and 1,1,1-trifluoropropyl-2-yl. Preferred compounds include fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and 1,1,1-trifluoropropyl-2-yl.

[0015] As used herein, the term “C1-C6-alkylene” refers to a divalent C1-C6-alkyl group as defined herein. Examples of C1-C6-alkylene groups include, but are not limited to, methylene, 1,2-ethylene, 1,1-ethylene, 1,3-propylene, 1,2-propylene, 2,2-propylene, 1,4-butylene, 1,3-butylene, 1,2-butylene, 1,5-pentylene, and 1,6-hexylene.

[0016] As used herein, the terms “C3-C8-cycloalkyl” and “C3-C8-cycloalkyl ring” refer to a saturated monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms. Examples of C3-C8-cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In particular, the cycloalkyl group has 3 to 6 carbon atoms.

[0017] As used herein, the term “C3-C8-halocycloalkyl” refers to a saturated hydrocarbon ring system in which all ring members (which may be 3 to 8) are carbon atoms, wherein one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0018] As used herein, the term "C2-C6-alkenyl" refers to an unsaturated branched or straight hydrocarbon chain having 2, 3, 4, 5, or 6 carbon atoms and containing at least one double bond. Examples of C2-C6-alkenyl include, but are not limited to, ethenyl (or "vinyl"), propen-2-en-1-yl (or "allyl"), propen-1-en-1-yl, but-3-enyl, but-2-enyl, but-1-enyl, pent-4-enyl, pent-3-enyl, pent-2-enyl, pent-1-enyl, hex-5-enyl, hex-4-enyl, hex-3-enyl, hex-2-enyl, hex-1-enyl, propen-1-en-2-yl (or "isopropenyl"), 2-methylpropen-2-enyl, 1-methylpropen-2-enyl, 2 -Methylprop-1-enyl, 1-methylprop-1-enyl, 3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl, 3-methylbut-2-enyl, 2-methylbut-2-enyl, 1-methylbut-2-enyl, 3-methylbut-1-enyl, 2-methylbut-1-enyl, 1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methyl Pentyl-4-enyl, 4-methylpentyl-3-enyl, 3-methylpentyl-3-enyl, 2-methylpentyl-3-enyl, 1-methylpentyl-3-enyl, 4-methylpentyl-2-enyl, 3-methylpentyl-2-enyl, 2-methylpentyl-2-enyl, 1-methylpentyl-2-enyl, 4-methylpentyl-1-enyl, 3-methylpentyl-1-enyl, 2-methylpentyl-1-enyl, 1-methylpentyl-1-enyl, 3-ethylbutyl-3-enyl, 2-ethylbutyl-3-enyl, 1-ethylbutyl-3-enyl, 3-ethylbutyl-2-enyl, 2-ethylbutyl-2-enyl, 1-ethylbutyl -2-enyl, 3-ethylbut-1-enyl, 2-ethylbut-1-enyl, 1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl, 1-isopropylprop-2-enyl, 2-propylprop-1-enyl, 1-propylprop-1-enyl, 2-isopropylprop-1-enyl, 1-isopropylprop-1-enyl, 3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)vinyl, but-1,3-dienyl, pent-1,4-dienyl, hex-1,5-dienyl or methylhexadienyl.

[0019] As used herein, the term "C2-C6-ynyl" refers to a branched or straight hydrocarbon chain having 2, 3, 4, 5, or 6 carbon atoms and containing at least one triple bond. Examples of C2-C6-ynyl include, but are not limited to, ethynyl, propynyl, propynyl-2-ynyl (or "propynyl"), butynyl, butynyl-2-ynyl, butynyl-3-ynyl, pentynyl, pentynyl-2-ynyl, pentynyl-3-ynyl, pentynyl-4-ynyl, hexynyl, hexynyl-2-ynyl, hexynyl-3-ynyl, hexynyl-4-ynyl, hexynyl-5-ynyl, 1-methylpropynyl-2-ynyl, 2-methylbutynyl-3-ynyl, 1-methylbutynyl-3-ynyl, 1-methylbutynyl-2-ynyl, 3-methylbutynyl-1-ynyl, 1-ethylpropynyl-2-ynyl, and 3-methylpentynyl-4-ynyl. 2-Methylpent-4-ynyl, 1-Methylpent-4-ynyl, 2-Methylpent-3-ynyl, 1-Methylpent-3-ynyl, 4-Methylpent-2-ynyl, 1-Methylpent-2-ynyl, 4-Methylpent-1-ynyl, 3-Methylpent-1-ynyl, 2-Ethylbut-3-ynyl, 1-Ethylbut-3-ynyl, 1-Ethylbut-2-ynyl, 1-Prop-2-ynyl, 1-Isopropylprop-2-ynyl, 2,2-Dimethylbut-3-ynyl, 1,1-Dimethylbut-3-ynyl, 1,1-Dimethylbut-2-ynyl or 3,3-Dimethylbut-1-ynyl.

[0020] As used herein, the term “C2-C6-haloalkenyl” means that one or more hydrogen atoms in a C2-C6-alkenyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0021] As used herein, the term “C2-C6-haloalkynyl” means that one or more hydrogen atoms in a C2-C6-alkynyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0022] As used herein, the term “C1-C6-alkoxy” refers to a group of the formula (C1-C6-alkyl)-O-, wherein the term “C1-C6-alkyl” is as defined herein. Examples of C1-C6-alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Unless otherwise defined, this definition also applies to alkoxy groups that are part of a complex substituent (e.g., alkoxyalkyl, alkoxyalkoxy).

[0023] As used herein, the term "C1-C6-haloalkoxy" means that one or more hydrogen atoms in a C1-C6-alkoxy group as defined above are replaced by one or more halogen atoms, which may be the same or different. Examples of C1-C6-haloalkoxy groups include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

[0024] As used herein, the term "C3-C8-cycloalkyloxy" refers to a monocyclic saturated cycloalkyloxy group having 3 to 8, preferably 3 to 6, carbocyclic members, such as (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. Unless otherwise defined, this definition also applies to cycloalkoxy groups that are part of a complex substituent (e.g., cycloalkoxyalkyl).

[0025] As used herein, the term “C1-C6-alkylthio” refers to a saturated straight-chain or branched group of the formula (C1-C6-alkyl)-S-, wherein the term “C1-C6-alkyl” is as defined herein. Examples of C1-C6-alkylthio groups include, but are not limited to, methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutylthio, tert-butylthio, pentylthio, isopentylthio, and hexylthio.

[0026] As used herein, the term “C1-C6-haloalkylthio” means that one or more hydrogen atoms in a C1-C6-alkylthio group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0027] As used herein, the term "C3-C8-cycloalkylthio" refers to a saturated, monovalent, monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms bonded to the backbone by sulfur atoms. Examples of monocyclic C3-C8-cycloalkylthio groups include, but are not limited to, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio, or cyclooctylthio.

[0028] As used herein, the term “C1-C6-alkylsulfinyl” refers to a saturated straight-chain or branched group of the formula (C1-C6-alkyl)-S(=O)-, wherein the term “C1-C6-alkyl” is as defined herein. Examples of C1-C6-alkylsulfinyl groups include, but are not limited to, saturated straight-chain or branched alkylsulfinyl groups having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, such as (but not limited to) C1-C6-alkylsulfinyl groups, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl 1,2-Dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl, and 1-ethyl-2-methylpropylsulfinyl.

[0029] As used herein, the term “C1-C6-haloalkylsulfinyl” means that one or more hydrogen atoms in a C1-C6-alkylsulfinyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0030] As used herein, the term "C1-C6-alkylsulfonyl" refers to a saturated straight-chain or branched group of the formula (C1-C6-alkyl)-S(=O)2-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylsulfonyl groups include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl. 2-Methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0031] As used herein, the term “C1-C6-haloalkylsulfonyl” means that one or more hydrogen atoms in a C1-C6-alkylsulfonyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0032] As used herein, the term “C1-C6-alkylcarbonyl” refers to a saturated straight-chain or branched group of the formula (C1-C6-alkyl)-C(=O)-, wherein the term “C1-C6-alkyl” is as defined herein.

[0033] As used herein, the term “C1-C6-haloalkylcarbonyl” means that one or more hydrogen atoms in a C1-C6-alkylcarbonyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0034] As used herein, the term “C1-C6-alkoxycarbonyl” refers to a saturated straight-chain or branched group of the formula (C1-C6-alkoxy)-C(=O)-, wherein the term “C1-C6-alkoxy” is as defined herein.

[0035] As used herein, the term “C1-C6-haloalkoxycarbonyl” means that one or more hydrogen atoms in a C1-C6-alkoxycarbonyl group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0036] As used in this article, the term "C3-C" 12 "-Carbocyclic group" refers to a saturated or partially unsaturated hydrocarbon ring system in which all ring members (which can be 3 to 12) are carbon atoms. The ring system can be monocyclic or polycyclic (fused, spiro, or bridged). C3-C 12 -Carbon cyclogroups include, but are not limited to, C3-C 12 -Cycloalkyl (monocyclic or bicyclic), C3-C 12 - Cycloalkenyl (monocyclic or bicyclic), bicyclic systems comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkenyl group (such as tetrahydronaphthyl, indanyl, 3-bicyclo[4.2.0]octyl-1,3,5-trienyl), bicyclic systems comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkenyl group (such as indanyl, dihydronaphthyl), and tricyclic systems comprising a cyclopropyl group connected to the bicyclic system via a carbon atom, wherein the bicyclic system comprises an aryl group (such as phenyl) fused to a C3-C8-cycloalkenyl or C3-C8-cycloalkenyl group. The C3-C12-carbon cycloalkenyl group may be connected to the parent molecule via any carbon atom.

[0037] As used in this article, the term "C6-C" 14 "-aryl" refers to an aromatic hydrocarbon ring system in which all ring members (which may be 6 to 14, preferably 6 to 10) are carbon atoms. The ring system may be monocyclic or fused polycyclic (such as bicyclic or tricyclic). Examples of aryl include, but are not limited to, phenyl, azulel, and naphthyl.

[0038] As used herein, the term "3- to 14-membered heterocyclic group" refers to a saturated or partially unsaturated 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14-membered ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Heterocyclic groups include, but are not limited to, 3- to 7-membered monocyclic heterocyclic groups and 8- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heterocyclic groups. A 3- to 14-membered heterocyclic group can be attached to a portion of the parent molecule via any carbon or nitrogen atom contained within the heterocyclic group. Examples of saturated heterocycles include, but are not limited to, 3-membered rings, such as oxetane propane and azirne propane; 4-membered rings, such as azirne butane, oxetane, and thioheterobutane; 5-membered rings, such as tetrahydrofuranyl, 1,3-dioxetane pentane, tetrahydrothiophene, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiazolyl; and 6-membered rings, such as piperidinyl and hexahydropyridyl. Azinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxacyclohexane, tetrahydrothiaranyl, dithiaalkyl, morpholinyl, 1,2-oxazhexacyclohexane, oxothiocyclohexane, thiomorpholinyl; or 7-membered rings, such as oxepanyl, azepanyl, 1,4-diazahexacyclohexane, and 1,4-oxazhexacyclohexane. Examples of unsaturated heterocycles include, but are not limited to, 5-membered rings, such as dihydrofuranyl, 1,3-dioxacyclopentenyl, dihydrothiophenyl, pyrrololinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, and dihydrothiazolyl; or 6-membered rings, such as pyranyl, thiaranyl, thiazinyl, and thiadiazinyl. Bicyclic heterocycles can consist of a monocyclic heteroaryl group as defined herein fused with a monocyclic C3-C8-cycloalkyl group, a monocyclic C3-C8-cycloalkenyl group, or a monocyclic heterocycle; or they can consist of a monocyclic heterocycle fused with an aryl group (such as a phenyl group), a C3-C8-cycloalkyl group, a C3-C8-cycloalkenyl group, or a monocyclic heterocycle. When two monocyclic heterocycles or one monocyclic heterocycle and a nitrogen-containing monocyclic heteroaryl group are fused, the nitrogen atom may be located at the bridging site (e.g., 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridyl). Tricyclic heterocycles can consist of a monocyclic cycloalkyl group that connects a bicyclic heterocycle by a shared atom.

[0039] As used herein, the terms “3- to 7-membered heterocyclic group” and “3- to 7-membered heterocyclic ring” refer to saturated 3, 4, 5, 6 or 7-membered ring systems containing 1, 2 or 3 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples include, but are not limited to, oxacyclopropane, aziroxane, aziroxane, oxacyclobutane, thiohexacyclobutane, tetrahydrofuranyl, 1,3-dioxacyclopentane, tetrahydrothiopheneyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, piperidinyl, hexahydropyrimidinyl, hexahydropyrimidinyl, piperazine, triazineyl, hexahydrotriazineyl, tetrahydropyranyl, dioxahexacycloyl, tetrahydrothiaranyl, dithiazolyl, morpholinyl, 1,2-oxacyclohexane, oxothiohexane, thiomorpholinyl, oxacycloheptane, aziroxaneheptane, 1,4-diazacycloheptane, and 1,4-oxacycloheptane. Preferred 3- to 7-membered heterocyclic groups are oxetane propane, azirane propane, azirane butane, oxetane butane, tetrahydrofuranyl, 1,3-dioxetane pentane, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxane-hexacycloyl, morpholinyl, and thiomorpholinyl.

[0040] As used herein, the term "5- to 14-membered heteroaryl" refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Aromatic heterocycles include 5- or 6-membered monocyclic heteroaryl and 7- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heteroaryl. 5- to 14-membered heteroaryl groups can be attached to a portion of the parent molecule via any carbon or nitrogen atom contained in the heterocycle.

[0041] As used herein, the term "5- or 6-membered heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring system comprising 1, 2, 3, or 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. Examples of 5-membered monocyclic heteroaryl groups include, but are not limited to, furanyl, thiophene, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, oxtriazolyl, isothiazolyl, thiazolyl, thiadiazolyl, and thiatriazolyl. Examples of 6-membered monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetraazinyl.

[0042] As used herein, the term "7- to 14-membered heteroaryl" refers to a 7, 8, 9, 10, 11, 12, 13, or 14-membered aromatic polycyclic (e.g., bicyclic or tricyclic) ring system comprising one, two, or three heteroatoms independently selected from oxygen, nitrogen, and sulfur. Bicyclic heteroaryls may consist of monocyclic heteroaryls as defined herein fused with an aryl (e.g., phenyl) or a monocyclic heteroaryl. Examples of bicyclic heteroaryl groups include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, and benzoisoxazolyl, or 10-membered rings such as quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridyl, pteridinal, and benzodioxinyl. In a 9- or 10-membered bicyclic heteroaryl group comprising two fused 5- or 6-membered monocyclic heteroaryl groups, the nitrogen atom may be located at the bridging site (e.g., imidazo[1,2-a]pyridyl, [1,2,4]triazolo[4,3-a]pyridyl, imidazo[1,2-a]pyridyl, imidazo[2,1-b]oxazolyl, furano[2,3-d]isooxazolyl). Examples of tricyclic aromatic heterocycles include, but are not limited to, carbazoyl, acridineyl, and phenazinyl.

[0043] As used in this article, the term "C3-C" 12 -Carbocyclooxygen group", "C3-C8-cycloalkyloxygen group", "C6-C 14 "-aryloxy", "5- to 14-membered heteroaryloxy", and "3- to 14-membered heterocyclic oxy" refer to groups of formula -OR, where R are C3-C6 as defined herein. 12 -Carbocyclic, C3-C8-cycloalkyl, C6-C 14 -Aryl, 5 to 14-membered heteroaryl or 3 to 14-membered heterocyclic group.

[0044] As used in this article, the term "C3-C" 12 -Carbocyclic thiogroup", "C6-C" 14 "-arylthio", "5- to 14-membered heteroarylthio", and "3- to 14-membered heterocyclic thio" refer to groups of formula -SR, where R are C3-C6 as defined in this paper. 12 -Carbocyclic group, C6-C 14 -Aryl, 5 to 14-membered heteroaryl or 3 to 14-membered heterocyclic group.

[0045] As used herein, the term “leaving group” should be understood to mean a group that is transferred from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate (“triflate”) group, an alkoxy group, a methanesulfonate group, or a p-toluenesulfonate group.

[0046] This document does not cover compounds obtained from combinations that contradict the laws of nature and that would therefore be excluded by a person skilled in the art based on his / her expertise. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[0047] The compounds of formula (I) may suitably be in their free form, salt form, N-oxide form or solvate form (e.g., hydrate).

[0048] Depending on the nature of the substituents, compounds of formula (I) can exist in different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, transisomers, or geometric isomers. Therefore, the present invention covers pure stereoisomers and any mixtures of these isomers. When a compound can exist in two or more tautomer forms in equilibrium, a compound mentioned by way of a tautomer description should be considered to include all tautomer forms.

[0049] Depending on the number of double bonds in the compound, any compound of the present invention may also exist in one or more geometric isomers. Depending on the nature of the substituents relating to the double bonds or rings, the geometric isomers may exist in cis (=Z-) or trans (=E-) forms. Therefore, the present invention also relates to all geometric isomers and all possible mixtures in all proportions.

[0050] Depending on the nature of the substituents, compounds of formula (I) can exist in the form of free compounds and / or their salts (such as active salts in agrochemistry).

[0051] Reactive salts in agricultural chemistry include acid addition salts of inorganic and organic acids, as well as salts of common bases. Examples of inorganic acids are hydrohalic acids (such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide), sulfuric acid, phosphoric acid, and nitric acid, as well as acid salts (such as sodium bisulfate and potassium bisulfate). Useful organic acids include, for example, formic acid, carbonic acid and alkyl acids (such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid), as well as glycolic acid, thiocyanate, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or monounsaturated or diunsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkyl sulfonic acids (sulfonic acids having straight-chain or branched alkyl groups with 1 to 20 carbon atoms), aryl sulfonic acids or aryl disulfonic acids (aromatic groups with one or two sulfonic acid groups, such as phenyl and naphthyl), alkyl phosphonic acids (phosphonic acids having straight-chain or branched alkyl groups with 1 to 20 carbon atoms), aryl phosphonic acids or aryl diphosphonic acids (aromatic groups with one or two phosphonic acid groups, such as phenyl and naphthyl), wherein the alkyl and aryl groups may have other substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0052] The solvates of the compounds or their salts of the present invention are stoichiometric compositions of the compounds and solvents.

[0053] The compounds of this invention can exist in various crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates, and hydrates.

[0054] Preferably, the present invention relates to compounds of formula (I) and their salts, hydrates, and hydrates of salts, wherein R 3 and R 4 Independently hydrogen, fluorine, or methyl, R 5 It is hydrogen. L represents a straight link, methylene, 1,1-ethylene, or 1,2-ethylene. in The methylene, 1,1-ethylene, and 1,2-ethylene are optionally replaced by one or two substituents L. SA replace, L SA It is fluorine. or Two substituents L bonded to the same carbon atom SA Together with the carbon atoms they are attached to, they form cyclopropyl rings or cyclobutyl rings. R 6 It can be indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanecyclohexenyl, furanyl, thiophene, indoleyl, or benzofuranyl. Indene, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanecyclohexenyl, furanyl, thiophene, indoleyl, and benzofuranyl are optionally surrounded by one or two R groups. 6S Substituent substitution, in, R 6S Independently selected from: fluorine, chlorine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetaneyl, tetrahydrofuranyl, pyrazolyl, and pyridinyl. The C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, and C2-C4-alkynyl groups are optionally substituted by one or two independent substituents selected from the following: hydroxyl and C1-C4-alkoxy. and The C3-C6 cycloalkyl, oxetyl, tetrahydrofuranyl, pyrazolyl, and pyridyl groups are optionally substituted by one or two independent substituents selected from the following: fluorine, chlorine, and C1-C4 alkyl groups. R 7 Selected from C1-C4-alkyl and CR 12 R 13 R 14 , in R 12 and R 13 Independently selected from hydrogen or methyl; and R 14 The group is selected from cyano, methylformyl, 2-(methylamino)-2-oxo-ethyl, phenyl, heteroaryl groups selected from pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, or heterocyclic groups selected from pyrrolidinyl, piperidinyl, and tetrahydropyranyl; wherein any one of the phenyl, heteroaryl, and heterocyclic groups is unsubstituted or substituented by one or two independently selected from the following groups R. 9 Substitution: fluorine, chlorine, cyano, methyl, ethyl, methoxy, or cyclopropyl; Q is phenyl, thiophene, or pyridinyl. The phenyl, thiophene, and pyridyl groups are optionally substituents of one or two groups. S replace, in Q S Independently selected from halogens, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, and C3-C6-cycloalkyl. in The C3-C6-cycloalkyl group is optionally substituted by one or two independent substituents selected from the following: fluorine, chlorine, and methyl.

[0055] In the above formula (I), preferably, R 6 It is a phenyl group. The phenyl group is optionally surrounded by one or two R groups. 6S Substituent substitution, in R 6S It is independently selected from fluorine, chlorine, C1-C4-alkyl, difluoromethyl and trifluoromethyl.

[0056] More preferably, R 6 Groups that are the following: in § 1 For the point connected to L, R 6S1 It is chlorine or methyl. R 6S2 It can be chlorine or methyl.

[0057] In the above formula (I), preferably, R 3 and R 4 It is hydrogen.

[0058] In the above formula (I), preferably, L is a methylene group.

[0059] In the above formula (I), preferably, R 3 and R 4 It is hydrogen and L is methylene.

[0060] In the above formula (I), preferably, R 7 Selected from C1-C4-alkyl and CR 12 R 13 R 14 ,in R 12 and R 13 Independently selected from hydrogen and methyl; and R 14 The group is selected from cyano, methylformyl, 2-(methylamino)-2-oxo-ethyl, phenyl; heteroaryl groups selected from pyridinyl, pyrimidinyl, pyridazinyl, thiazolyl, oxazolyl, and imidazolyl; or heterocyclic groups selected from pyrrolidinyl, piperidinyl, and tetrahydropyranyl, wherein any one of the phenyl, heteroaryl, and heterocyclic groups is unsubstituted or substituented by one or two independently selected substituents R. 9 Substitution: fluorine, chlorine, cyano, methyl, ethyl, methoxy, or cyclopropyl, preferably R 14 It is an unsubstituted pyridinyl group.

[0061] More preferably, R 7 It is selected from methyl, ethyl, isopropyl, 4-pyridylmethyl and 2-methyl-allyl.

[0062] Even more preferably, R 7 It is a methyl group.

[0063] In the above formula (I), preferably, Q is a group of the following formula: , in § 2 The point where it connects to the oxygen atom. Q S1 It is hydrogen or fluorine. Q S2 It can be chlorine, fluorine, methyl, trifluoromethyl, or cyclopropyl.

[0064] In the above formula (I), preferably, L is a methylene group, and R 6 It is a phenyl group. The phenyl group is optionally surrounded by one or two R groups. 6S Substituent substitution, in R 6S It is independently selected from fluorine, chlorine, C1-C4-alkyl, difluoromethyl and trifluoromethyl.

[0065] More preferably, L is methylene, and R 6 Groups that are the following: in § 1 For the point connected to L, R 6S1 It is chlorine or methyl. R 6S2 It can be chlorine or methyl.

[0066] The present invention more preferably relates to compounds of formula (I) and their salts, hydrates, and hydrates of salts, wherein R 3 and R 4 It is hydrogen. R 5 It is hydrogen. L stands for methylene. R 6 Groups that are the following: in § 1 For the point connected to L, R 6S1 It is chlorine or methyl. R 6S2 It is chlorine or methyl. R 7 It is methyl. Q Groups that are the following: in § 2 The point where it connects to the oxygen atom. Q S1 It is hydrogen or fluorine. Q S2 It can be chlorine, fluorine, methyl, trifluoromethyl, or cyclopropyl.

[0067] Even more preferably, the present invention relates to compounds of formula (I) and their salts, hydrates, and hydrates of salts, wherein the compounds of formula (I) are one of the following: - 5-(3-chlorophenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-chlorophenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-chlorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-cyclopropylphenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chlorophenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, - 4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, and - 4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one.

[0068] Even more preferably, the present invention relates to compounds of formula (I), wherein a compound of formula (I) is one of the following: - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-chlorophenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chlorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-cyclopropylphenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one.

[0069] The R defined above 3 R 4 R 5 R 6 R 7 L and Q (broad definitions and preferred, more preferred, and even more preferred definitions) can be combined in different ways. Therefore, combinations of these definitions provide subsets of compounds according to the invention, such as those disclosed below.

[0070] The compounds of formula (I) can be used as fungicides (for the control of plant pathogenic fungi), particularly in methods for the control of plant pathogenic fungi, the method comprising the step of applying one or more compounds of formula (I) to a plant, plant part, seed, fruit or to the soil in which the plant grows.

[0071] Methods and intermediates for preparing compounds of formula (I) This invention relates to a method for preparing compounds of formula (I) and intermediates thereof. Unless otherwise stated, group R... 3 R 4 R 5 R 6 R 7 L and Q have the meanings given above for compounds of formula (I). These definitions apply not only to the final product of formula (I) but also to all intermediates.

[0072] The compounds of formula (Ia) are various subsets of formula (I), where R 5 It is hydrogen.

[0073] Compounds of formula (I) can be prepared by various routes similar to known methods (see examples and references in this paper). Non-limiting examples of suitable methods are described herein.

[0074] Compounds of formula (I) can be obtained directly by performing methods A through E, or by converting or derivatizing another compound of formula (I) prepared according to the methods described herein. For example, a compound of formula (I) can be converted into a compound of another formula (I) by replacing one or more substituents of a starting compound of formula (I) with other substituents.

[0075] The methods described herein can be suitably carried out using one or more inert organic solvents commonly used for the reactions under consideration. Suitable inert organic solvents may be selected from the following: aliphatic, alicyclic, or aromatic hydrocarbons (e.g., petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, light petroleum, benzene, toluene, xylene, or decahydronaphthalene), halogenated aliphatic, alicyclic, or aromatic hydrocarbons (e.g., chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or trichloroethane), ethers (e.g., diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole), ketones (e.g., acetone, methyl ethyl ketone, etc.). Methyl isopropyl ketone and methyl isobutyl ketone), esters (e.g., methyl acetate, ethyl acetate or butyl acetate), alcohols (e.g., methanol, ethanol, propanol, isopropanol, butanol, tert-butanol), nitriles (e.g., acetonitrile, propionitrile, n-butyronitrile or isobutyronitrile or benzonitrile), amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamine), sulfoxides (e.g., dimethyl sulfoxide) or sulfones (e.g., sulfolane), ureas (e.g., 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) or any mixture thereof.

[0076] Some of the methods described herein may require, or optionally, the use of one or more inorganic or organic bases commonly used in the reaction. Examples of suitable inorganic and organic bases include, but are not limited to, alkaline earth metal or alkali metal carbonates (e.g., sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, or cesium carbonate), alkali metal hydrides (e.g., sodium hydride), alkaline earth metal or alkali metal hydroxides (e.g., sodium hydroxide, calcium hydroxide, potassium hydroxide, or other ammonium hydroxide derivatives), fluorides of alkaline earth metals, alkali metals, or ammonium (e.g., potassium fluoride, cesium fluoride, or tetrabutylammonium fluoride), alkali metal or alkaline earth metal acetates (e.g., sodium acetate, lithium acetate, potassium acetate, or calcium acetate), and alkali metal alkoxides (e.g., sodium acetate, lithium acetate, potassium acetate, or calcium acetate). Examples of bases include potassium tert-butoxide or sodium tert-butoxide, alkali metal phosphates (e.g., tripotassium phosphate), tertiary amines (e.g., trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dicyclohexylmethylamine, N,N-diisopropylethylamine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), diazabicycloundecene (DBU), quinine ring, 3-acetoxyquinine ring, guanidine, or aromatic bases (e.g., pyridine, methylpyridine, dimethylpyridine, or trimethylpyridine).

[0077] Some of the methods described herein can optionally be carried out in the presence of a transition metal catalyst (e.g., a metal (e.g., a copper or palladium) salt or complex), and, if appropriate, in the presence of a ligand.

[0078] Suitable copper salts or complexes and their hydrates include, but are not limited to, copper metal, copper iodide (I), copper chloride (I), copper bromide (I), copper chloride (II), copper bromide (II), copper oxide (II), copper oxide (I), copper acetate (II), copper acetate (I), copper thiophene-2-carboxylate (I), copper cyanide (I), copper sulfate (II), bis(2,2,6,6-tetramethyl-3,5-heptadecanoic acid)copper (II), copper trifluoromethanesulfonate (II), tetra(acetonitrile)copper hexafluorophosphate (I), and tetra(acetonitrile)tetrafluoroborate (I).

[0079] By adding copper salts and ligands or salts separately to the reaction mixture, suitable copper complexes can also be generated in situ within the reaction mixture. The ligands or salts are, for example, ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, etc. rac -trans-1,2-diaminocyclohexane, rac -trans-N,N'-dimethylcyclohexane-1,2-diamine, 1,1'-binaphthyl-2,2'-diamine, N,N,N',N'-tetramethylethylenediamine, proline, N,N-dimethylglycine, quinoline-8-ol, pyridine, 2-aminopyridine, 4-(dimethylamino)pyridine, 2,2'-bipyridine, 2,6-bis(2-pyridyl)pyridine, 2-pyridinecarboxylic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-o-diazanthroline, 3,4,7,8-tetramethyl-1,10-o-diazanthroline, 2,9-dimethyl-1,10-o-diazanthroline, 4,7-dimethoxy-1,10-o-diazanthroline, N,N'-bis[ (E)-pyridin-2-ylmethylene]cyclohexane-1,2-diamine, N-[(E)-phenylmethylene], N-[(E)-phenylmethylene]-cyclohexylamine, 1,1,1-tris(hydroxymethyl)ethane, n-butylimidazolium, ethylene glycol, 2,2,6,6-tetramethylheptane-3,5-dione, 2-(2,2-dimethylpropionyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropionyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphine, vinylbis(diphenylphosphine), N,N-diethylsalicylic acid amide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid, or 1H-pyrrole-2-carboxylic acid.

[0080] Suitable palladium salts or complexes include, but are not limited to, palladium chloride, palladium acetate, tetra(triphenylphosphine)palladium (0), bis(dibenzylacetone)palladium (0), tri(dibenzylacetone)dipalladium (0), bis(triphenylphosphine)palladium (II), [1,1'-bis(diphenylphosphine)ferrocene]palladium (II), bis(cinnamyl)dichlorodipalladium (II), bis(allyl)-dichlorodipalladium (II) or [1,1'-bis(di-tert-butylphosphine)ferrocene]palladium (II).

[0081] Palladium complexes can also be formed in the reaction mixture by adding palladium salts and ligands or salts, such as triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2,6'-dimethoxybiphenyl, 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, triphenylphosphine, and tri-(o-tolyl) Phosphine, sodium 3-(diphenylphosphine)benzenesulfonate, tris-(2-methoxy-phenyl)phosphine, 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, 1,4-bis(diphenylphosphine)butane, 1,2-bis(diphenylphosphine)ethane, 1,4-bis(dicyclohexylphosphine)butane, 1,2-bis(dicyclohexylphosphine)ethane, 2-(dicyclohexylphosphine)-2'-(N,N-dimethylamino)biphenyl, 1,1'-bis(diphenylphosphine)ferrocene, (R)-(-)-1-[(S)-2-diphenylphosphine)ferrocene]ethyldicyclohexylphosphine, tris-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine, or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

[0082] Suitable catalysts and / or ligands can be selected from commercial catalogs, such as Strem Chemicals' "Metal Catalysts for Organic Synthesis", or from reviews (Chemical Society Reviews (2014)). 43 , 3525, Coordination Chemistry Reviews (2004), 248 , 2337 and its references).

[0083] Some of the methods described in this article can be performed via metal photo-oxidation-reduction catalysis according to the methods recorded in the literature (Nature Chemistry Review, (2017) 0052 and its references; Science (2016) 352,6291, 1304; Org. Lett. 2016, 18, 4012, J. Org. Chem 2016, 81, 6898; J. Am. Chem. Soc. 2016, 138, 12715, J. Am. Chem. Soc. 2016, 138, 13862; J. Am. Chem. Soc. 2016, 138, 8034; J. Org. Chem. 2016, 81, 12525, J. Org. Chem. 2015, 80,7642). The method is then carried out in the presence of a photosensitizer (e.g., an Ir and Ru complex or an organic dye) and a metal catalyst (e.g., a Ni complex). The reaction can be carried out in the presence of a ligand, and, if appropriate, under blue or white light irradiation in the presence of a base.

[0084] Suitable photosensitizers include, but are not limited to, Ir(III) photocatalysts, such as [Ir(dFCF3ppy)2(bpy)]PF6 (dFCF3ppy = 2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy = 2,2'-bipyridine), [Ir(dFCF3ppy)2(dtbbpy)]PF6 (dtbbpy = 4,4'-di-tert-butyl-2,2'-bipyridine), Ir(ppy)2(dtbbpy)PF6 (ppy = 2-phenylpyridine), Ir(ppy)2(bpy)PF6, Ir(dFppy)3PF6 (dFCF3ppy = 2-(2,4-difluorophenyl)pyridine), fac -Ir(ppy)3, (Ir[diF(5-Me)ppy]2(tetraMePhen)PF6 (diF(5-Me)ppy = 2-(2,4-difluorophenyl)-5-methylpyridine, tetraMePhen = 3,4,7,8-tetramethyl-1,10-o-diazaphenanthroline); Ru(II) photocatalysts, such as Ru(bpy)3Cl2 or Ru(bpy)3(PF6)2; or organic dyes, such as 9-isopropylacetone-10-acridine perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9 H -Carbazole-9-yl-1,3-benzonitrile, 9-fluorenone and 9,10-phenanthroline.

[0085] Suitable nickel catalysts include, but are not limited to, bis(1,5-cyclooctadiene) nickel (0), nickel chloride (II), nickel bromide (II), nickel iodide (II), nickel acetylacetonate (II), and nickel nitrate (II) hexahydrate, either in anhydrous or hydrated form or as a dimethoxyethane complex. These nickel catalysts can be used in combination with bipyridine ligands (e.g., 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine), or o-phenanthroline (e.g., 1,10-o-phenanthroline, 4,7-dimethyl-1,10-o-phenanthroline, 4,7-dimethoxy-1,10-o-phenanthroline), or diamines (e.g., N,N,N',N'-tetramethylethylenediamine), or diketones (e.g., tetramethylheptanedione).

[0086] The methods described herein can be carried out at temperatures ranging from -105°C to 250°C, preferably from -78°C to 185°C.

[0087] The reaction time varies depending on the scale of the reaction and the reaction temperature, but it is usually between a few minutes and 48 hours.

[0088] The methods described in this article are typically performed at standard pressure. However, they can also be performed at increased or decreased pressure.

[0089] The methods described herein can optionally be performed under microwave radiation conditions, at atmospheric pressure, or under pressure.

[0090] In the methods described herein, the starting material is typically used in approximately equimolar amounts. However, a relatively large excess of a starting material may also be used.

[0091] Method for preparing compounds of formula (I) Method A Compounds of formula (Ia), wherein R 3 R 4 R 6 R 7 L and Q are as defined above, and R 5 For hydrogen It can be prepared as shown in Scheme 1 by the following method. When W is hydrogen, the compound of formula (4) (where R is hydrogen) is optionally treated with a dehydrating agent in the presence of a base. 3 R 4 R 5 R 6 R 7 L and Q (as defined above) directly yield compounds of formula (Ia). or When W is an amino protecting group (e.g., tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl), the compound of formula (4) is optionally treated with a dehydrating agent in the presence of a base, followed by a deprotection step to obtain the compound of formula (Ia). Compounds of formula (Ia) can be obtained by treating compounds of formula (4) with a dehydrating agent (such as POCl3, P2O5, or trifluoromethanesulfonic anhydride) optionally in the presence of a base. This method of forming an oxadiazine ring is known and described in the literature (J. Med. Chem. 2017, 60, 2383-2400) and patents WO2020127780, WO2021245083, WO2021249995, and WO2021245087. The reaction can be carried out in any common inert organic solvent. Preferably, halogenated aliphatic, alicyclic, or aromatic hydrocarbons are used, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, or decahydronaphthalene; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, or trichloroethane; ethers, such as diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole; nitriles, such as acetonitrile, propionitrile, n-butyronitrile, isobutyronitrile, or benzonitrile; and alcohols, such as ethanol or isopropanol.

[0092] When W represents an amino protecting group, an additional deprotection step is performed after step 3 using the reaction conditions described in the literature (Greene's Protective Groups inorganic Synthesis; Peter GM Wuts; Wiley; 5th ed.; 2014; 895-1194). For example, the tert-butoxycarbonyl group can be removed in an acidic medium such as hydrochloric acid or trifluoroacetic acid.

[0093] The compound of formula (4) can be obtained by the following methods: -make the compound of formula (1) (where R) 7 And Q as defined above and U 1 (where R is a hydroxyl, halogen, or C1-C6-alkoxy group) and an amine of formula (2) (where R is a hydroxyl, halogen, or C1-C6-alkoxy group) 3 R 4 R 5 R 6 The compound is reacted with L as defined above and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl) or a salt thereof to obtain the compound of formula (3) (where R is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl) to obtain the compound of formula (3) (where R is hydrogen, tert-butoxycarbonyl, benzyl or allyl or (4-methoxyphenyl)methyl) to obtain the 3 R 4 R 5 R6 R 7 L, Q, and W are as defined above); and -Removing the phthalimide group from compound (3) yields compound (4).

[0094] The reaction conditions for removing phthalimide groups are well known and have been reported in the literature (Greene's Protective Groups in organic Synthesis; Peter GM Wuts; Wiley; 5th ed.; 2014; 1012-1014).

[0095] The compounds of formula (1) can be prepared by one or more methods described herein (see method F) or by the method described in patent WO2023 / 166067.

[0096] The amine of formula (2) can be prepared by the methods described in patents WO2020 / 127780, WO20212 / 45083, WO20212 / 49995 and WO20212 / 45087.

[0097] Among them U 1 Compounds of formula (1) with a hydroxyl group can be reacted with amines of formula (2) in the presence of a condensing agent by methods described in the literature (e.g., Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensing agents include, but are not limited to, halogenating agents (e.g., carbohydrate, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, or thionyl chloride), dehydrating agents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride), carbodiimides (e.g., N,N'-dicyclohexylcarbodiimide (DCC)), or other conventional condensing (or peptide coupling) agents (e.g., phosphorus pentoxide, polyphosphate, bis(2-oxo-3-oxazolyl)phosphonyl chloride, 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1,3,5]-triazin-2-yl)-4-methylmorpholine hydrochloride hydrate, tripyrrolidinyl phosphonium hexafluorophosphate or propylphosphonic anhydride (T3P).

[0098] Among them U 1Compounds of formula (1) containing halogen atoms can react with amines of formula (2) in the presence of an acid scavenger by well-known methods. Suitable acid scavengers include any inorganic and organic bases commonly used in such reactions as described herein. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic bases are preferred.

[0099] Among them U 1 Compounds of formula (1) that are C1-C6-alkoxy can react with an excess of an amine of formula (2), optionally in the presence of a Lewis acid (such as trimethylaluminum).

[0100] Method B Compounds of formula (Ia) (where R) 3 R 4 R 5 R 6 R 7 R, L, and Q (as defined above) can be prepared as shown in Scheme 2 by making the compound of formula (7), wherein R 3 R 4 R 5 R 6 R 7 And L is as defined above, and X is a halogen, preferably chlorine or bromine. The compound of formula (8) (where Q is as defined above) reacts with a base (e.g., an organic or inorganic base) and optionally with a suitable copper salt or complex. The compound of formula (7) can be prepared by first preparing the compound of formula (5), wherein R 7 And X as defined above, and U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. With an amine of formula (2) or a salt thereof, wherein R 3 R 4 R 5 R 6 And L is as defined above, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. The reaction yields a compound of formula (6a), wherein R 3 R 4 R 5 R 6 R 7 L, X, and W are as defined above. Then, the phthalimide group of compound (6a) is removed to obtain compound (6b), wherein R3 R 4 R 5 R 6 R 7 L, X, and W are as defined above, and Under the same conditions as described in this paper for method A When W is hydrogen, the compound of formula (6b) is optionally treated with a dehydrating agent in the presence of a base to directly obtain the compound of formula (7). When W is an amino protecting group, the compound of formula (6b) is optionally treated with a dehydrating agent in the presence of a base, followed by a deprotection step to obtain the compound of formula (7).

[0101] The reaction of the compound of formula (7) with the compound of formula (8) can be carried out in the presence of a base, optionally in the presence of a suitable transition metal catalyst (such as a copper salt or complex), and if appropriate in the presence of the ligand described herein.

[0102] The compound of formula (5) is commercially available or can be prepared by hydrolysis of compound (18).

[0103] The compound of formula (8) is commercially available or can be obtained by converting or derivatizing another compound of formula (8) using well-known methods.

[0104] Method C Compounds of formula (Ia) (where R) 3 R 4 R 5 R 6 R 7 (R, L, and Q as defined above) can be prepared as shown in Scheme 3 by: under acidic conditions, to a compound of formula (12) (where R, L, and Q are as defined above) 3 R 4 R 6 R 7 A reducing agent is added to (L and Q as defined above) to obtain a compound of formula (Ia). The compound of formula (12) can be cyclized under acidic conditions in the presence of a reducing agent (such as sodium cyanoborohydride) to obtain the compound of formula (Ia). The reaction conditions for forming the oxadiazine ring by this method are known and have been described in the literature (Heterocycles 2016, 92, 2166-2200, WO2020 / 127780, WO20212 / 45083, WO20212 / 49995 and WO20212 / 45087).

[0105] The compound of formula (12) can be converted into the compound of formula (10) (where R) in the presence of a base. 7 And Q as defined above) and the compound of formula (11) (where R) 3 R 4 R 6 It is obtained by reacting with L (as defined above). Suitable bases may be alkali metal hydrides (such as sodium hydride), alkali metal carbonates (such as potassium carbonate), alkali metal hydroxides (such as potassium hydroxide), or phosphononitrile bases (such as BEMP as described in Heterocycles 2016, 92, 2166-2200).

[0106] The compound of formula (10) can be made by making the compound of formula (9) (where R) 7 Q is obtained by reacting hydroxylamine (as defined above) with a salt thereof. The reaction conditions for carrying out the conversion are known and have been reported in the literature (WO2010 / 138600).

[0107] The compound of formula (9) can be prepared from the compound of formula (18) by the method described in step 3 of method B. (18) Where R 7 And X as defined above.

[0108] The compound of formula (11) is commercially available or can be prepared by the method described in the literature (Eur. J. Med. Chem. 2014, 84,302, Eur. J. Med. Chem. 2015, 100, 18-23, WO2017 / 031325).

[0109] The compound of formula (18) is commercially available or can be prepared by the method described in the literature (WO2021 / 256900 or WO2023 / 166067).

[0110] Method D Compounds of formula (Ia) (where R) 3 R 4 R 5 R 6 R 7 L and Q (as defined above) can be prepared as shown in Scheme 4 by a method comprising the following steps: -make the compound of formula (1) (where R) 7 U 1 And Q (as defined above) and an amine of formula (13) or a salt thereof, wherein R 3 R 4 R 5R 6 And L, as defined above, E 1 It is a hydroxyl or halogen, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. The reaction is carried out under similar conditions as described in method A to obtain a compound of formula (14), wherein R 3 R 4 R 5 R 6 R 7 E 1 L, W, and Q are as defined above. - Treat the compound of formula (14) with a dehydrating agent, then treat with hydroxylamine to form the compound of formula (15), wherein R 3 R 4 R 5 R 6 R 7 E 1 L, Q, and W are as defined above, and When E 1 When the hydroxyl group is used, the compound of formula (15) is converted into the compound of formula (Ia) using photoelectrophoresis reaction conditions. When E 1 When the halogen is present, the compound of formula (15) is converted into the compound of formula (Ia) in the presence of a base. Steps 2 and 3 of method D can be carried out under similar reaction conditions as described in method E.

[0111] Formula (13-a, E 1 = hydroxyl) amino alcohols are commercially available or can be prepared by methods described in the literature (Molecules, 9 (6), 405-426, 2004; WO2017 / 203474, WO2020 / 127780, WO20212 / 45083, WO20212 / 49995 and WO20212 / 45087). Formula (13-b, E 1 = halogen) compounds or their salts can be obtained from the corresponding amino alcohols by well-known methods.

[0112] Method E Compounds of formula (Ia) (where R) 3 R 4 R 5 R 6 R 7 L and Q (as defined above) can be prepared as shown in Scheme 5 by a method comprising the following steps: - make the compound of formula (5), where R 7 As defined above, and X is a halogen, preferably chlorine or bromine. U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. - with an amine of formula (13) or a salt thereof, wherein R 3 R 4 R 5 R 6 And L, as defined above, E 1 It is a hydroxyl or halogen, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. The reaction is carried out under similar conditions as described in method A to obtain a compound of formula (16), wherein R 3 R 4 R 5 R 6 R 7 E 1 L, W, and X are as defined above. - Treat the compound of formula (16) with a dehydrating agent, then treat with hydroxylamine to form the compound of formula (17), wherein R 3 R 4 R 5 R 6 R 7 E 1 L and X are as defined above, and When E 1 When the hydroxyl group is used, the compound of formula (17) is converted into the compound of formula (7) using photoelectrophoresis reaction conditions. When E 1 When the halogen is present, the compound of formula (17) is converted into the compound of formula (7) in the presence of a base. - make the compound of formula (7), where R 3 R 4 R 5 R 6 R 7 L and X are as defined above. - The compound of formula (8) (where Q is as defined above) is reacted with a base (e.g., an organic or inorganic base) in the presence of a suitable copper salt or complex to obtain the compound of formula (Ia). Method for preparing compounds of formula (I) Compounds of formula (1) as described herein can be obtained directly by performing method F below, or by converting or derivatizing another compound of formula (1) prepared according to the methods described herein or WO2023 / 166067.

[0113] Method F Compound of formula (1) (where R) 7 As defined above, the compound of formula (5) can be prepared as shown in Scheme 6 by the following method: where R... 7 As defined above, and X is a halogen, preferably chlorine or bromine. U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. The reagent of formula (8) (where Q is as defined above) reacts in the presence of a base. Method F can be carried out in the presence of a suitable transition metal catalyst salt or complex, and if appropriate in the presence of a ligand as described in Eur. J. Org. Chem. 2011, 18, 3353-3360, to obtain a compound of formula (1) (where U 1 (C1-C6-alkoxy).

[0114] The compound of formula (5) is commercially available or can be prepared by hydrolysis of compound (18).

[0115] The compound of formula (8) is commercially available or can be obtained by converting or derivatizing another compound of formula (8) using well-known methods.

[0116] Compound of formula (1) (where U 1 (C1-C6-alkoxy) can be converted into a compound of formula (1) (where U is C1-C6-alkoxy) by known functional group interconversion methods (e.g., by hydrolyzing the ester group with LiOH in THF / water). 1 (Hydroxyl group).

[0117] Compound of formula (1) (where U 1 (where U is a hydroxyl group) can be converted into a compound of formula (1) by known methods in the presence of a halogenating agent (where U is a hydroxyl group). 1 (Halogen). Suitable halogenating agents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, or thionyl chloride.

[0118] intermediate This invention also relates to compounds of formulas (3) and (4): in R 3 R 4 R 5 L, R 6 R 7 Q is as defined in equation (1), W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0119] For R given by equation (I) 3 R 4 R 5 L, R 6 R 7 The definitions of preferred, more preferred, even more preferred and most preferred for Q also apply after necessary modifications to the details.

[0120] This invention also relates to compounds of formula (7): (7), in R 3 R 4 R 5 L, R 6 and R 7 As defined in equation (1), X is a halogen, preferably chlorine or bromine.

[0121] For R given by equation (I) 3 R 4 R 5 L, R 6 and R 7 The definitions of preferred, more preferred, even more preferred and most preferred are also applicable after necessary modifications to the details.

[0122] This invention also relates to compounds of formula (10): in Q and R 7 As defined in equation (1).

[0123] For Q and R given by equation (I) 7 The definitions of preferred, more preferred, even more preferred and most preferred are also applicable after necessary modifications to the details.

[0124] This invention also relates to compounds of formula (12): in R 3 R 4 L, R 6R 7 Q is as defined in equation (1), For R given by equation (I) 3 R 4 L, R 6 R 7 The definitions of preferred, more preferred, even more preferred and most preferred for Q also apply after necessary modifications to the details.

[0125] The present invention also relates to compounds of formulas (14) and (15): (14), and (15) in R 3 R 4 R 5 L, R 6 and R 7 As defined in equation (1), E 1 It is a hydroxyl group or a halogen, preferably a hydroxyl group, chlorine, or bromine. E 2 It is a hydroxyl group. and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0126] For R given by equation (I) 3 R 4 R 5 L, R 6 and R 7 The definitions of preferred, more preferred, even more preferred and most preferred are also applicable after necessary modifications to the details.

[0127] The present invention also relates to compounds of formulas (16) and (17): (16), and (17) in R 3 R 4 R 5 L, R 6 and R 7 As defined in equation (1), X is a halogen, preferably chlorine or bromine. E 1 It is a hydroxyl group or a halogen, preferably a hydroxyl group, chlorine, or bromine. E 2 It is a hydroxyl group. and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0128] For R given by equation (I) 3 R 4 R 5 L, R 6 and R 7 The definitions of preferred, more preferred, even more preferred and most preferred are also applicable after necessary modifications to the details.

[0129] Compositions and Formulations The present invention also relates to compositions, particularly compositions for controlling unwanted microorganisms. These compositions can be applied to the microorganisms and / or their habitats.

[0130] The composition A compound comprising at least one of formula (I) and at least one suitable agricultural adjuvant, such as a carrier and / or a surfactant.

[0131] carrier It is a solid or liquid, natural or synthetic, organic or inorganic substance, typically inert. The carrier usually facilitates the application of the compound to, for example, plants, plant parts, or seeds. Suitable solid carrier Examples include, but are not limited to: ammonium salts, particularly ammonium sulfate, ammonium phosphate, and ammonium nitrate; natural rock powders such as kaolin, clay, talc, chalk, quartz, palygorskite, montmorillonite, and diatomaceous earth; silica gel and synthetic rock powders such as finely dispersed silica, alumina, and silicates. Typical examples of useful solid carriers for preparing granules include, but are not limited to: pulverized and graded natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; synthetic granules of inorganic and organic powders; and granules of organic materials such as paper, sawdust, coconut husks, corn cobs, and tobacco stalks. Suitable liquid carrier Examples include, but are not limited to: water, organic solvents, and combinations thereof. Suitable solventExamples include polar and nonpolar organic chemical liquids, such as aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, alkanes, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalene, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or dichloromethane), alcohols and polyols (which may optionally be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or ethylene glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, their amides (e.g., dimethylformamide or fatty acid amides) and esters, lactams (e.g., N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide), and oils derived from plants or animals. The carrier can also be a liquefied gas propellant, that is, a liquid that is gaseous at standard temperature and standard pressure, such as aerosol propellants like halogenated hydrocarbons, butane, propane, nitrogen, and carbon dioxide.

[0132] The preferred solid carrier is selected from clay, talc and silica.

[0133] The preferred liquid carrier is selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams and carbonates.

[0134] The amount of carrier is typically 1 to 99.99% by weight, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight, and most preferably 20 to 99% by weight, based on the weight of the composition.

[0135] The liquid carrier is typically present at 20 to 99% by weight, such as 30 to 80% by weight, based on the weight of the composition.

[0136] The solid carrier is typically present in 0 to 50% by weight, preferably 5 to 45% by weight, such as 10 to 30% by weight, based on the weight of the composition.

[0137] If the composition contains two or more carriers, the above range refers to the total amount of carriers.

[0138] The surfactantsIt can be an ionic (cationic or anionic), amphoteric or nonionic surfactant, such as ionic or nonionic emulsifiers, foaming agents, dispersants, wetting agents, penetration enhancers and any mixture thereof. Examples of suitable surfactants include, but are not limited to: polyacrylates, lignin sulfonates (e.g., sodium lignin sulfonate), phenol sulfonates or naphthalene sulfonates, condensates of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids, or fatty amines (e.g., polyoxyethylene fatty acid esters, such as castor oil ethoxylates; polyoxyethylene fatty alcohol ethers, such as alkylaryl polyethylene glycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (e.g., triphenylphenylphenol ethoxylates), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurine esters), phosphate esters of polyethoxylated alcohols or phenols, fatty esters of polyols (e.g., fatty acid esters of glycerol, sorbitol, or sucrose), sulfates (e.g., alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl sulfonates, aryl sulfonates, and alkylbenzene sulfonates), phosphate esters, protein hydrolysates, lignin sulfite waste, and methylcellulose. Any salt mentioned in this paragraph preferably refers to its respective alkali metal salt, alkaline earth metal salt, or ammonium salt.

[0139] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, such as calcium dodecylbenzene sulfonate, castor oil ethoxylate, sodium lignosulfonate, and arylphenol ethoxylates, such as tristyrylphenol ethoxylate.

[0140] The amount of surfactant is typically 5 to 40% by weight, for example 10 to 20% by weight, based on the weight of the composition.

[0141] Suitable adjuvantsOther examples include waterproofing agents, desiccants, adhesives (glues, tackifiers, fixatives such as carboxymethyl cellulose, natural and synthetic polymers in powder, granule or latex form (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate), natural phospholipids (e.g. cephalin and lecithin) and synthetic phospholipids, polyvinylpyrrolidone and methylcellulose (tylose)), thickeners and secondary thickeners (e.g. cellulose ethers, acrylic derivatives, xanthan gum, modified clays, such as available products named Bentone, and finely dispersed silica), stabilizers (e.g. cold stabilizers, preservatives (e.g. dichlorophenol)). (phene) and benzyl alcohol hemiacetal), antioxidants, light stabilizers (especially UV stabilizers) or other agents that can improve chemical and / or physical stability, dyes or pigments (e.g., inorganic pigments such as iron oxide, titanium dioxide and Prussian blue; organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes), defoamers (e.g., silicone defoamers and magnesium stearate), antifreeze, adhesives, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrants, chelating agents and complexing agents.

[0142] The choice of adjuvant depends on the intended manner of application of the compound of formula (I) and / or the physical properties of the compound. Furthermore, adjuvants can be selected to impart specific properties (technical, physical, and / or biological properties) to the composition or the form of use prepared therefrom. The selection of adjuvants can allow the composition to be customized to specific needs.

[0143] The compositions of the present invention can be provided to the end user in the form of a ready-to-use formulation, i.e., the composition can be applied directly to plants or seeds using suitable equipment such as a sprayer or powderer. Alternatively, the composition can be provided to the end user in the form of a concentrate, which must be diluted before use, preferably with water.

[0144] The compositions of the present invention can be prepared in a conventional manner, for example by mixing a compound of formula (I) with one or more suitable adjuvants (such as those disclosed above).

[0145] The composition comprises a fungicide-effective amount of a compound of formula (I). The term "effective amount" refers to an amount sufficient to control harmful fungi on cultivated plants or in the protection of materials without causing substantial damage to the treated plants. Such an amount can vary widely and depends on various factors, such as the species of fungus to be controlled, the cultivated plant or material being treated, climatic conditions, and the specific compound of formula (I) used. Typically, the compositions of the present invention comprise 0.01 to 99% by weight, preferably 0.05 to 98% by weight, more preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight of a compound of formula (I). The composition may contain two or more compounds of the present invention. In this case, the above ranges refer to the total amount of the compounds of the present invention.

[0146] The compositions of the present invention can be any conventional Composition form Examples of such formulations include solutions (e.g., aqueous solutions), emulsions, water-based and oil-based suspensions, powders (e.g., wettable powders, soluble powders), powders, pastes, granules (e.g., soluble granules, broadcast granules), suspension concentrates, natural or synthetic products impregnated with compounds of formula (I), fertilizers, and microencapsulations in polymeric substances. Compounds of formula (I) may exist in suspended, emulsified, or dissolved forms. Examples of particularly suitable composition types include solutions, water-soluble concentrates (e.g., SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (e.g., SC, OD, OF, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or granules (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GW, GF). These and other composition types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview is given in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition, May 2008, Croplife International.

[0147] Preferably, the composition of the present invention is in one of the following forms: EC, SC, FS, SE, OD and WG, more preferably EC, SC, OD and WG.

[0148] Further details regarding examples of composition types and their preparation are given below. If two or more compounds of the present invention are present, the generalized amount of the compounds refers to the total amount of the compounds of the present invention. If representatives of any other component of two or more compositions are present, such as wetting agents or binders, this applies to such components with the necessary modifications to the details.

[0149] i) Water-soluble concentrates (SL, LS) Dissolve 10-60% by weight of at least one compound of formula (I) and 5-15% by weight of a surfactant (e.g., polyoxyethylene fatty alcohol ether) in a corresponding amount of water and / or a water-soluble solvent (e.g., an alcohol such as propylene glycol, or a carbonate such as propylene carbonate) to obtain a total of 100% by weight. Dilute the concentrate with water before application.

[0150] ii) Dispersible concentrate (DC) Dissolve 5-25% by weight of at least one compound of formula (I) and 1-10% by weight of a surfactant and / or binder (e.g., polyvinylpyrrolidone) in a corresponding amount of organic solvent (e.g., cyclohexanone) to obtain a total amount of 100% by weight. Dilute with water to obtain a dispersant.

[0151] iii) Emulsifiable concentrate (EC) Dissolve 15-70% by weight of at least one compound of formula (I) and 5-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) in a corresponding amount of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon or fatty acid amide) and, if necessary, an additional water-soluble solvent to obtain a total of 100% by weight. Dilute with water to obtain an emulsion.

[0152] iv) Emulsions (EW, EO, ES) Dissolve 5-40% by weight of at least one compound of formula (I) and 1-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) in 20-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). Add the mixture to the appropriate amount of water using an emulsifier to obtain a total volume of 100% by weight. The resulting composition is a homogeneous emulsion. The emulsion may be further diluted with water before application.

[0153] v) Suspension agents and suspension concentrates v-1) Water-based (SC, FS) In a suitable grinding apparatus (e.g., a stirred ball mill), 20-60% by weight of at least one compound of formula (I) is pulverized, while 2-10% by weight of a surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., xanthan gum), and water are added to obtain a fine suspension of the active substance. Water is added in appropriate amounts to obtain a total of 100% by weight. The suspension is diluted with water to obtain a stable suspension of the active substance. For FS-type compositions, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0154] v-2) Oil-based (OD, OF) In a suitable grinding apparatus (e.g., a stirred ball mill), 20-60% by weight of at least one compound of formula (I) is pulverized, while 2-10% by weight of a surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., modified clay, particularly Bentone or silica), and an organic carrier are added to obtain a fine oil suspension of the active substance. The organic carrier is added in appropriate amounts to obtain a total of 100% by weight. Diluting with water yields a stable dispersant of the active substance.

[0155] vi) Water-dispersible granules and water-soluble granules (WG, SG) Finely grind 50-80% by weight of at least one compound of formula (I), while adding a surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), and convert it into water-dispersible or water-soluble granules using technical equipment (e.g., extrusion, spray tower, fluidized bed). Use the surfactant in appropriate amounts to obtain a total of 100% by weight. Dilute with water to obtain a stable dispersant or solution of the active substance.

[0156] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) In a rotor-stator mill, 50-80% by weight of at least one compound of formula (I) is ground, while 1-8% by weight of a surfactant (e.g., sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and a corresponding amount of a solid carrier (e.g., silica gel) are added to obtain a total amount of 100% by weight. The mixture is then diluted with water to obtain a stable dispersant or solution of the active substance.

[0157] viii) Gel agents (GW, GF) In a stirred ball mill, 5-25% by weight of at least one compound of formula (I) is pulverized, while 3-10% by weight of a surfactant (e.g., sodium lignosulfonate), 1-5% by weight of a binder (e.g., carboxymethyl cellulose), and the corresponding amount of water are added to obtain a total of 100% by weight. This results in a fine suspension of the active substance. Diluting with water yields a stable suspension of the active substance.

[0158] ix) Microemulsion (ME) 5-20% by weight of at least one compound of formula (I) is added to 5-30% by weight of a mixture of organic solvents (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a mixture of surfactants (e.g., polyoxyethylene fatty alcohol ethers and arylphenol ethoxylates), and a corresponding amount of water to obtain a total of 100% by weight. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0159] x) Microencapsulation (CS) An oil phase comprising 5-50 wt% of at least one compound of formula (I), 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15 wt% of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and diacrylate or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of at least one compound of formula (I), 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and an isocyanate monomer (e.g., diphenylmethylene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer content is 1-10 wt%, based on the total weight of the CS composition.

[0160] xi) Powder (DP, DS) Finely grind 1-10% by weight of at least one compound of formula (I) and tightly mix it with a corresponding amount of solid carrier (e.g., finely dispersed kaolin) to obtain a total amount of 100% by weight.

[0161] xii) Granules (GR, FG) Finely grind 0.5-30% by weight of at least one compound of formula (I) and combine it with a corresponding amount of solid support (e.g., silicate) to obtain a total amount of 100% by weight. Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0162] xiii) Ultra-low volume liquid (UL) Dissolve 1-50% by weight of at least one compound of formula (I) in a corresponding amount of organic solvent (e.g., aromatic hydrocarbon) to obtain a total amount of 100% by weight.

[0163] Composition types i) to xiii) may optionally contain other auxiliaries, such as 0.1-1 wt% preservative, 0.1-1 wt% defoamer, 0.1-1 wt% dye and / or pigment, and 5-10 wt% antifreeze.

[0164] Mixtures / combinations The compounds and compositions of formula (I) of the present invention can be mixed with other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, biocontrol agents, or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, chemical pheromones, and / or other agriculturally beneficial agents are also possible. This can broaden the activity spectrum or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides, and bactericides are disclosed in the Pesticide Manual, 17th edition.

[0165] Examples of fungicides that can be mixed with compounds and compositions of formula (I) of the present invention include: 1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) fluoxytioconazole, (1.010) fluquinconazole, (1.011) flutriafol, (1.012) hexaconazole, (1.013) Imazalil (1.014), Imazalil sulfate (1.015), Ipconazole (1.016), Ipfentrifluconazole (1.017), Mefentrifluconazole (1.018), Metconazole (1.019), Myclobutanil (1.020), Paclobutrazol (1.021), Penconazole (1.022), Prochloraz (1.023), Proiconazole (1.024), Prothioconazole (1.025), Pyrisoxazole (1.026) Spiroxamine, (1.027) Tebuconazole, (1.028) Tetraconazole, (1.029) Triadimenol, (1.030) Tridemorph, (1.031) Triticonazole, (1.032) 4-[[6-[(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzylnitrile, (1.033) 4-[[6-[(2S)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzyl nitrile, (1.034) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, (1.035) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, (1.036) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane-2-yl}methyl)-1H-1,2,4-triazole, (1.037) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, (1.039) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, (1.040) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxylon, (1.041) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate, (1.042) (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]- Methyl 2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, (1.043) (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, (1.044) N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformamidinium, (1.045) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformamidin, (1.046) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformamidin, (1.047) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidin, (1.048) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformamidin, (1.049) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidin, (1.050) N'-[5-bromo-6-(2,3-dihydro-1H-indene-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidin, (1.051) N'-{4-[(4,5-dichloro-1,3-thiazolyl-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidin, (1.052) N'-{5-bromo-2-methyl-6-[(1-propoxypropyl-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylformamidin, (1.053) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidin, (1.054) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidin, (1.055)N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidin, (1.056) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidin, (1.057) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidin, (1.058) N-Isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformamidin, (1.059) 4-[(E)-[ethyl(methyl)amino]methyleneamino]-2,5-dimethylbenzoic acid p-tolyl methyl ester, (1.060) N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methylformamidin.

[0166] 2) Inhibitors of respiratory chain complexes I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) flubeneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) furamepyr, (2.012) inpyrfluxam, (2.013) Isofetamid (2.014), isoflucypram (2.015), isopyrazam (2.016), penflufen (2.017), penthiopyrad (2.018), pydiflumetofen (2.019), pyrapropoyne (2.020), piraziflumid (2.021), sedaxane (2.022), thifluzamide (aka trifluzamide) (2.023) 5,8-Difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.024) 5-chloro-N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]oxyethyl]-6-ethyl-pyrimidin-4-amine, (2.025) N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]oxyethyl]quinazolin-4-amine, (2.026) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamide, (2.027) 2-Fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.028) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthyl-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.033) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthyl-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.034) N-[1-(2,4-dichlorophenyl)-1-methoxypropyl-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.035) 5-Chloro-1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-3H-isobenzofuran-4-yl]pyrazole-4-carboxamide, (2.036) 5-Chloro-1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-3H-isobenzofuran-4-yl]pyrazole-4-carboxamide, (2.037) N-[2-[(1S)-1,3-dimethylbutyl]phenyl]-5-fluoro-1,3-dimethyl-pyrazole-4-carboxamide, (2.038) N-[2-[(1R)-1,3-dimethylbutyl]phenyl]-5-fluoro-1,3-dimethyl-pyrazole-4-carboxamide, (2.039) 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, (2.040) 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, (2.041) N-[2-[(1S)-1,3-dimethylbutyl]-3-thienyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide, (2.042) N-[2-[(1R)-1,3-dimethylbutyl]-3-thienyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide, (2.043) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.044) 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide.

[0167] 3) Inhibitors of respiratory chain complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florylpicoxamid, (3.013) Flufenoxystrobin (3.014), Fluoxastrobin (3.015), Kresoxim-methyl (3.016), Mandestrobin (3.017), Metarylpicoxamid (3.018), Metominostrobin (3.019), Metyltetraprole (3.020), Orysastrobin (3.021), Picoxystrobin (3.022), Pyraclostrobin (3.023), Pyrametostrobin (3.024), Pyraoxystrobin (3.025) Pyribencarb, (3.026) Trifloxystrobin, (3.027) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide, (3.029) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide, (3.030) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.031) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.032) (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (3.033) (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, (3.034) (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, (3.035) (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]prop-2-enoic acid methyl ester, (3.036) (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]prop-2-enoic acid methyl ester, (3.037) {5-[3-(2,4-dimethylphenyl)-1H-pyrazole-1-yl]-2-methylbenzyl}carbamate methyl ester, (3.038) (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[3-(trifluoromethyl)phenyl]ethyleneamino]oxymethyl]phenyl]acetamide, (3.039) (2E)-2-[2-[[(E)-1-(3,5-difluorophenyl)ethyleneamino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide, (3.040) [rac-2-(4-bromo-7-fluoro-indole-1-yl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridin-2-carbonyl)amino]propionate, (3.041) [rac-2-(7-bromo-4-fluoro-indole-1-yl)-1-methyl-propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridin-2-carbonyl)amino]propionate, (3.042) [rac-2-(7-bromoindole-1-yl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, (3.043) [rac-2-(3,5-dichloro-2-pyridyl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, (3.044) [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, (3.045) [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, (3.046) [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propionate, (3.047) [2-[[(1S)-2-[(1RS,2SR)-2-(3,5-dichloro-2-pyridyl)-1-methyl-propoxy]-1-methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropionate, (3.048) 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, (3.049) 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3.4]oct-3-yl-thiazole-4-carboxamide, (3.050) 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-hexyl-5-methyl-thiazole-4-carboxamide, (3.051) 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, (3.052) 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, (3.053) 2-[(2,6-difluoro-4-pyridinyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, (3.054) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-carboxamide-2-hydroxybenzamide.

[0168] 4) Inhibitors of mitosis and cell division, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridachlometyl, (4.009) pyriofenone (chlazafenone), (4.010) thiabendazole, (4.011) Thiophanate-methyl, (4.012) zoxamide, (4.013) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017) 4-(2-Bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.018) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.019) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.020) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.022) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.023) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.024) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.026) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.027) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.028) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

[0169] 5) Compounds capable of multi-site action, such as (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper sulfate (2+), (5.010) Dithianon, (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Mancozeb, (5.015) Metiram, (5.016) Metiram zinc, (5.017) Oxine-copper, (5.018) Propineb, (5.019) Sulfur and sulfur preparations including calcium polysulfides, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram, (5.023) 6-Ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiainro[2,3-c][1,2]thiazolyl-3-carboxylonitrile.

[0170] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, fosetyl-aluminium, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isothiazine, (6.006) phosphorous acid and its salts, (6.007) probenazole, and (6.008) tiadinil.

[0171] 7) Inhibitors of amino acid and / or protein biosynthesis, such as (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, and (7.005) pyrimethanil.

[0172] 8) Inhibitors of ATP production, such as (8.001) silthiofam.

[0173] 9) Inhibitors of cell wall synthesis, such as (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, and (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0174] 10) Inhibitors of lipid synthesis or transport, or membrane synthesis, such as (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetone, (10.009) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetone, (10.010) 2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]acetone, (10.011) 2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]acetone, (10.012) 2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazolyl)piperidin-1-yl]acetone, (10.013) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidin-4-yl)-1,3-thiazolyl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (10.014) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazolyl-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (10.015) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (10.016) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-1,5-dihydro-2,4-benzodioxane-6-ylmethanesulfonate, (10.017) 9-Fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-1,5-dihydro-2,4-benzodioxane-6-yl methanesulfonate, (10.018) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-1,5-dihydro-2,4-benzodioxane-6-yl methanesulfonate, (10.019) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazo-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxane-6-yl methanesulfonate.

[0175] 11) Inhibitors of melanin biosynthesis, such as (11.001) tolprocarb and (11.002) tricyclazole.

[0176] 12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M, kiralaxyl, (12.003) metalaxyl, (12.004) high-efficiency metalaxyl-M (mefenoxam).

[0177] 13) Inhibitors of signal transduction, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, and (13.006) vinclozolin.

[0178] 14) Compounds that can act as uncoupling agents, such as (14.001) fluazinam and (14.002) meptyldinocap.

[0179] 15) Other compounds, such as (15.001) abscisic acid, (15.002) aminopyrifen, (15.003) benthiazole, (15.004) bethoxazin, (15.005) capsimycin, (15.006) carvone, (15.007) chinomethionat, (15.008) chloroinconazide, (15.009) cufraneb, (15.010) cyflufenamid, (15.011) cymoxanil, (15.012) cyprosulfamide, (15.013) Dipymetitrone, (15.014) D-tagatose, (15.015) flufenoxadiazam, (15.016) flumetylsulforim, (15.017) flutianil, (15.018) ipflufenoquin, (15.019) methyl isothiocyanate, (15.020) mildiomycin, (15.021) nickel dimethyldithiocarbamate, (15.022) nitrothal-isopropyl, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts Salts), (15.025) Picarbutrazox, (15.026) Quinofumelin, (15.027) Tebufloquin, (15.028) Tecloftalam, (15.029) Tolnifanide, (15.030) 2-(6-benzylpyridin-2-yl)quinazoline, (15.031) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.032) 2-Phenylenol and its salts, (15.025) 2-phenylphenol and its salts.033) 4-Amino-5-fluoropyrimidin-2-ol (tautomer: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.034) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.035) 5-amino-1,3,4-thiadiazole-2-thiol, (15.036) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazine, (15.037) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.038) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.039) Butyl-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.040) (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.041) methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, (15.042) N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, (15.043) phenazine-1-carboxylic acid, (15.044) propyl 3,4,5-trihydroxybenzoate, (15.045) Quinoline-8-ol, (15.046) Quinoline-8-ol sulfate (2:1), (15.047) (2R)-2-benzyl-N-(8-fluoro-2-methyl-3-quinolinyl)-2,4-dimethyl-pentanamide, (15.048) (2S)-2-benzyl-N-(8-fluoro-2-methyl-3-quinolinyl)-2,4-dimethyl-pentanamide, (15.049) 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.050) 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, (15.051) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.052) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.053) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.054) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.055)055) 4,4-Difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, (15.056) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, (15.057) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.058) 2-{2-fluoro-6-[(8-fluoro-2-methylquinoline-3-yl)oxy]phenyl}prop-2-ol, (15.059) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinoline, (15.060) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)-8-fluoroquinoline, (15.061) 3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline, (15.062) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl)quinoline, (15.063) 4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, (15.064) 4,4-Difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, (15.065) 5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline, (15.066) 7,8-difluoro-N-[rac-1-benzyl-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.067) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl)-quinoline, (15.068) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)-quinoline, (15.069) 8-Fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbut-2-yl)quinoline-3-carboxamide, (15.070) 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.071) 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.072) 8-Fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbut-2-yl]quinoline-3-carboxamide, (15.073) 8-Fluoro-N-[rac-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.074) 9-Fluoro-2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1,4-benzoxazine, (15.075) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, (15.076) N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, (15.077) N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, (15.078) N-[(2R)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide, (15.079) rac-2-benzyl-N-(8-fluoro-2-methyl-3-quinolinyl)-2,4-dimethyl-pentanamide, (15.080) (5RS)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (15.081) (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (15.082) (5RS)-5-(4-bromo-2-methylbenzyl)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine, (15.083) (5RS)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (15.084) (5S)-5-(4-bromo-2-methylbenzyl)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine, (15.085) (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (15.086) (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (15.087) 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazin-4-carboxamide, (15.088) 3-(3-bromo-2-fluorophenoxy)-6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide, (15.089) 6-Chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazin-4-carboxamide, (15.090) 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazin-4-carboxamide, (15.091) 6-Chloro-3-(3-chloro-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazin-4-carboxamide, (15.092) N-[2-(2-bromo-4-methylphenyl)-2,2-difluoroethyl]-6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide, (15.093) 1,1-diethyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.094) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]azacycloheptane-2-one, (15.096) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.097) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.098) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole, (15.100) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.101) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.103) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-2-one, (15.104) 4,4-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.105) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethyl carbamate, (15.106) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.107) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine, (15.108) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)propyl]pyrimidin-2-amine, (15.109) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.110) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.111) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine, (15.112) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-phenylethyl]pyrimidin-2-amine, (15.113) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine, (15.114) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidone-2-one, (15.115) 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.116) {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.117) N-(1-Methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.118) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.119) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.120) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.121) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.122) N-[(E)-N-methoxy-C-methyl-carboniminoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.123) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.124) N-[(Z)-N-methoxy-C-methyl-carboniminoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.125) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropionamide, (15.126) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.127) N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropaneformamide, (15.128) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butyramide, (15.129) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropaneformamide, (15.130) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propionamide, (15.131) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, (15.132) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.133) N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.134) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.135) N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.136) N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylthioamide, (15.137) N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylamide, (15.138) 2,2-difluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic acid.

[0180] All named mixed components of classes (1) to (15) described above may exist in the form of free compounds, or, if their functional groups are capable of salt formation, in the form of their agrochemically active salts.

[0181] The compounds and compositions of formula (I) of the present invention can also be combined with one or more biocontrol agents.

[0182] As used herein, the term “biological control” is defined as the control of harmful organisms, such as plant pathogenic fungi and / or insects and / or mites and / or nematodes, by using or utilizing biological control agents.

[0183] As used herein, the term "biocontrol agent" is defined as a non-harmful organism and / or proteins or secondary metabolites produced by such organism for biocontrol purposes. Mutants of a second organism should be included within the definition of a biocontrol agent. The term "mutant" refers to a variant of a parent strain, and the method for obtaining the mutant or variant, wherein the pesticide activity is greater than that expressed by the parent strain. Here, "parent strain" is defined as the original strain before mutagenesis. To obtain such a mutant, the parent strain can be treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl sulfone, or by irradiation with gamma rays, X-rays, or ultraviolet light, or by other methods well known to those skilled in the art. Known biocontrol mechanisms involve controlling root rot caused by gut bacteria competing for space with fungi on the root surface. Bacterial toxins (such as antibiotics) have been used to control pathogens. These toxins can be isolated and applied directly to plants, or a bacterial species can be applied to induce in situ production of the toxin.

[0184] "Variants" refers to strains that possess all the identifying characteristics of the NRRL or ATCC registry numbers shown in this article and can be identified as having genomes that hybridize with the NRRL or ATCC registry numbers under high stringency conditions.

[0185] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stable by hydrogen bonds between the bases of nucleotide residues. Hydrogen bonds can occur through Watson-Crick base pairing, Hoogstein binding, or any other specific sequence. The complex can consist of two strands forming a double-stranded structure, three or more strands forming a multi-stranded complex, a single self-hybridized strand, or any combination of these. Hybridization reactions can be carried out under different "strict" conditions. Typically, low-strict hybridization reactions are carried out at approximately 40°C in solutions of 10 X SSC or equivalent ionic strength / temperature. Medium-strict hybridization reactions are typically carried out at approximately 50°C in 6 X SSC, while high-strict hybridization reactions are typically carried out at approximately 60°C in 1 X SSC.

[0186] Variants designated with NRRL or ATCC accession numbers can also be defined as strains whose genomic sequence shares greater than 85%, more preferably greater than 90%, or even more preferably greater than 95% sequence identity with the genome designated with the NRRL or ATCC accession number. A percentage (e.g., 80%, 85%, 90%, or 95%) of sequence identity between a polynucleotide or polynucleotide region (or polypeptide or polypeptide region) and another sequence means that, when aligned, that percentage of bases (or amino acids) are identical when comparing the two sequences. This alignment and percentage of homology or sequence identity can be determined using software programs known in the art, for example, as described in Current Protocols in Molecular Biology (FM Ausubel et al., ed., 1987).

[0187] NRRL is an abbreviation for the Agricultural Research Service Culture Collection, an international repository for storing microbial strains. Under the Budapest Treaty, the storage of microorganisms for patent purposes is internationally recognized. Its address is National Center for Agricultural Utilization Research, Agricultural Research Service, USDepartment of Agriculture, 1815 North University Street, Peroira, Illinois 61604 USA.

[0188] ATCC is an abbreviation for the American Type Culture Collection, an international repository for storing microbial strains. Under the Budapest Treaty, the storage of microorganisms for patent purposes is internationally recognized. The address is ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110 USA.

[0189] Examples of biocontrol agents that can be combined with compounds and compositions of formula (I) of the present invention include: (A) Antibacterial agents selected from the following: (A1) Bacteria, such as (A1.1) Bacillus subtilis ( Bacillus subtilis ), especially strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661, US Patent No. 6,060,051); (A1.2) Bacillus species ( Bacillus sp.), especially strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL). ® Obtained), Registry No. FERMBP-8234, US Patent No. 7,094,592; (A1.3) Bacillus pumilus ( Bacillus pumilus ) ， In particular, strain BU F-33, NRRL registry number 50185 (available from BASF via CARTISSA). ® Partial acquisition of the product, EPA registration number 71840-19); (A1.4) Bacillus subtilis ( Bacillus subtilis var. amyloliquefaciens Strain FZB24, accession number DSM 10271 (available from Novozymes via TAEGRO) ® Or TAEGRO ® ECO (EPA Registration No. 70127-5) obtained); (A1.5) Bacillus species ( Paenibacillus strain (sp.), accession number NRRL B-50972 or accession number NRRLB-67129, WO 2016 / 154297; (A1.6) Bacillus subtilis ( Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS) ® PLUS, VELONDIS ® FLEX and VELONDIS ® EXTRA obtained); (A1.7) Bacillus mohair from Certis USA LLC (a subsidiary of Mitsui & Co.) Bacillus mojavensis (A1.8) Bacillus subtilis strain R3B (accession number NCAIM (P) B001389) (WO 2013 / 034938); (A1.9) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.1) Bacillus polymyxa ( Paenibacillus polymyxa), especially strain AC-1 (e.g., TOPSEED from Green Biotech Company Ltd. ® (A1.10) Pseudomonas proradix (For example, PRORADIX from Sourcon Padena) ® (A1.11) Pantothecin clumps ( Pantoea agglomerans ), especially strain E325 (registration number NRRL B-21856) (available from NorthwestAgri Products as BLOOMTIME BIOLOGICAL). TM FD BIOPESTICIDE (obtained); and (A2) Fungi, such as (A2.1) budding short-stemmed mold ( Aureobasidium pullulans ), especially budding spores of strain DSM14940, budding spores of strain DSM14941, or mixtures of budding spores of strains DSM14940 and DSM14941 (e.g., from bio-ferm, CH BOTECTOR). ® and BLOSSOM PROTECT ® (A2.2) Aphid pseudoyeast ( Pseudozyma aphidis (As disclosed by Yissum Research Development Company of the Hebrew University of Jerusalem in WO2011 / 151819); (A2.3) Saccharomyces cerevisiae ( Saccharomyces cerevisiae ), especially strains from Lesaffre et Compagnie, FR, CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938 or CNCM No. I-3939 (WO 2010 / 086790). (B) Selected from the following biological fungicides: (B1) Bacteria, such as (B1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer Crop Science LP, US as SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661 and described in US Patent No. 6,060,051); (B1.2) Bacillus pumilus, particularly strain QST2808 (available from Bayer Crop Science LP, US as SONATA®, NRRL Registry No. B-30087 and described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE as Yield Shield®); (B1.4) Bacillus pumilus, particularly strain BU F-33, NRRL registration number 50185 (available from BASF as a Cartisa product, EPA registration number 71840-19); (B1.5) Bacillus amyloliquefaciens ( Bacillus amyloliquefaciens ), particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. under Double Nickel™, Registry No. FERM BP-8234, US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan under BIOBAC) ® (B1.7) Bacillus subtilis strain MBI 600 (available from BASF SE under SUBTILEX), registration number NRRL B-50595, US Patent No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, DE under Kodiak®); (B1.9) Bacillus amyloliquefaciens strain FZB24, registration number DSM 10271 (available from Novozymes under TAEGRO). ® Or TAEGRO ® ECO (EPA registration number 70127-5) obtained); (B1.10) Bacillus mycoides ( Bacillus mycoides ) ， Isolator J, registration number B-30890 (available from Certis USALLC (a subsidiary of Mitsui & Co.) under BMJ TGAI) ® Or WG and LifeGard TM (B1.11) Bacillus licheniformis ( Bacillus licheniformis ), especially strain SB3086, registry number ATCC 55406, WO 2003 / 000051 (available from Novozymes with ECOGUARD) ® Biological fungicide and Green Releaf TM (B1.12) Bacillus species ( Paenibacillus (species), accession number NRRL B-50972 or NRRL B-67129, WO 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814, (available from BASF SE under the VELONDIS) ® PLUS, VELONDIS ® FLEX and VELONDIS ® (B1.14) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL registry number B-50768; WO 2014 / 028521) (from Marrone Bio Innovations STARGUS). ® (B1.16) Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (available from ABiTEP, DE as RHIZOVITAL) ® (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from QUARTZO of FMC Corporation). ® (WG) and PRESENCE ® (WP)); (B1.18) Bacillus mohaiwai strain R3B (accession number NCAIM (P) B001389) (WO 2013 / 034938) from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.19) Bacillus polymyxa subsp. plantarum from BASF SE ( Paenibacillus polymyxa ssp. plantarum (WO 2016 / 020371); (B1.20) Epiphytic Bacillus from BASF SE ( Paenibacillus epiphyticus (WO 2016 / 020371); (B.1.21) *Pseudomonas aeruginosa* ( Pseudomonas chlororaphisStrain AFS009, registry number NRLRB-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO from AgBiome Innovations, US) ® (B1.22) Pseudomonas aeruginosa, particularly strain MA342 (e.g., CEDOMON provided by Bioagri and Koppert). ® CERALL ® and CEDRESS ® (B1.23) Streptomyces lidii ( Streptomyces lydicus strain WYEC108 (also known as Streptomyces lidiense strain WYCD108US) (from Novozymes' ACTINO-IRON) ® and ACTINOVATE ® ); (B1.24) Agrobacterium radioactiveis ( Agrobacterium radiobacter ) strain K84 (e.g., GALLTROL-A from AgBioChem, CA) ® (B1.25) Agrobacterium radialis strain K1026 (e.g., from NOGALL, BASF SE) TM (B1.26) Bacillus subtilis KTSB strain (from Donghys FOLIACTIVE) ® (B1.27) Bacillus subtilis IAB / BS03 (from STK Bio-Ag Technologies' AVIV) TM (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan under the name BIOBAC) ® WP obtained, registered in Taiwan as a biofungicide under registration numbers 4764, 5454, 5096 and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria) TM (B1.30) Methyltrophic Bacillus ( Bacillus methylotrophicus ) strain BAC-9912 (from Chinese Academy of Sciences' Institute of Applied Ecology); (B1.31) Pseudomonas proradix (For example, PRORADIX from Sourcon Padena) ® (B1.32) Streptomyces glaucus ( Streptomyces griseoviridis Strain K61 (also known as Streptomyces flavus) Streptomyces galbus(Strain K61) (Registration No. DSM 7206) (MYCOSTOP from Verdera) ® PREFENCE from BioWorks ® See Crop Protection 2006, 25, 468-475); (B1.33) *Pseudomonas fluorescens* ( Pseudomonas fluorescens ) strain A506 (e.g., BLIGHTBAN provided by NuFarm) ® );and (B2) Fungi, such as: (B2.1) Shield-shell mold ( Coniothyrium minitans ) ， In particular, strain CON / M / 91-8 (accession number DSM-9660; e.g., Contans® from Bayer CropScience Biologics GmbH); (B2.2) *Saccharomyces cerevisiae* ( Metschnikowia fructicola ) ， In particular, strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea (B2.5) Dark green Trichoderma ( Trichoderma atroviride ), particularly strain SC1 (accession number CBS 122089, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA)), strain 77B (from Andermatt Biocontrol's T77) or strain LU132 (e.g., from Agrim Technologies Limited's Sentinel); (B2.6) Trichoderma harzianum ( Trichoderma harzianum ) strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from SimbioseAgro); (B2.14) Pink broom mold ( Gliocladium roseum (also known as pink spiral polyspora) Clonostachys rosea f. rosea(), especially strain 321U from Adjuvants Plus, strain ACM941 disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524), or strain IK726 (Jensen DF et al. Development of a biocontrol agent for plant disease control with special emphasis on the nearcommercial fungal antagonist) Clonostachys rosea strain 'IK726'; AustralasPlant Pathol. 2007;36:95–101); (B2.35) Yellow Demodex ( Talaromyces flavus ), strain V117b; (B2.36) Trichoderma viride ( Trichoderma viride ), especially strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); (B2.37) Trichoderma echinosporum ( Trichoderma asperellum (B2.38) *Trichoderma viride*, specifically strain SKT-1, registration number FERM P-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry), strain T34 (e.g., T34Biocontrol from Biocontrol Technologies SL, ES), or strain ICC 012 from Isagro; (B2.39) *Trichoderma viride*, strain CNCM I-1237 (e.g., Esquive® WP from Agrauxine, FR); ， Strain number V08 / 002387; (B2.40) Trichoderma viride ， Strain NMI number V08 / 002388; (B2.41) Trichoderma viride ，Strain NMI No. V08 / 002389; (B2.42) *Trichoderma viride*, strain NMI No. V08 / 002390; (B2.43) *Trichoderma viride*, strain LC52 (e.g., Tenet provided by Agrim Technologies Limited); (B2.44) *Trichoderma viride*, strain ATCC 20476 (IMI 206040); (B2.45) *Trichoderma viride* ， Strain T11 (IMI352941 / CECT20498); (B2.46); Trichoderma harmatum (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum ( Trichoderma harzianum rifai ) T39 (e.g., Trichodex® from Makhteshim, US); (B2.49) Trichoderma echinosporum ， In particular, strain kd (e.g., T-Gro from Andermatt Biocontrol); (B2.50) *Trichoderma harzianum*, strain ITEM 908 (e.g., Trianum-P from Koppert); (B2.51) *Trichoderma harzianum*, strain TH35 (e.g., Root-Pro from Mycontrol); (B2.52) *Trichoderma viride* ( Trichoderma virens (also known as green broom mold) Gliocladium virens (B2.53) *Trichoderma viride*, strain TV1 (e.g., *Trianum-P* provided by Koppert); (B2.54) *Pseudomonas aeruginosa* (…). Ampelomyces quisqualis (B2.56) Budding short-stemmed molds, especially budding spores of strain DSM14940; (B2.57) Budding short-stemmed molds, especially budding spores of strain DSM 14941; (B2.58) Budding short-stemmed molds, especially a mixture of budding spores of strains DSM14940 and DSM 14941 (e.g., Botector® from bio-ferm, CH); (B2.64) Cladosporium-like cladocerans ( Cladosporium cladosporioides ) ， Strain H39, accession number CBS122244, US 2010 / 0291039 (provided by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) *Streptococcus spp.* Gliocladium catenulatum (Synonyms:) Clonostachys rosea f. in chains) strain J1446 (e.g., Prestop® supplied by Lallemand); (B2.70) Verticillium spp. ( Lecanicillium lecanii (formerly known as) Verticillium lecanii Conidia of strain KV01 (e.g., Vertalec® supplied by Koppert / Arysta); (B2.71) Penicillium verum ( Penicillium vermiculatum (B2.72) Abnormal Pichia pastoris ( Pichia anomalous (B2.75) *Trichoderma viride*, strain WRL-076 (NRRL Y-30842), US Patent No. 7,579,183; (B2.75) *Trichoderma viride*, strain SKT-1 (FERM P-16510), Japanese Patent Publication No. 11-253151 A; (B2.76) *Trichoderma viride* ， Strain SKT-2 (FERM P-16511), Japanese Patent Publication No. 11-253151 A; (B2.77) *Trichoderma viride*, strain SKT-3 (FERM P-17021), Japanese Patent Publication No. 11-253151 A; (B2.78) *Trichoderma geysii* ( Trichoderma gamsii (Previously it was) T. green ), strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma provided by AGROBIOSOL DE MEXICO, SA DE CV); (B2.79) Trichoderma harzianum, strain DB 103 (available from Dagutat Biolab T-Gro ® 7456 obtained); (B2.80) Trichoderma polysporum ( Trichoderma polysporum ), strain IMI 206039 (e.g., BinabTF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stroma ( Trichoderma stromaticum ), registration number Ts3550 (e.g., Tricovab provided by CEPLAC, Brazil); (B2.83) Odman's sclerotium ( Ulocladium oudemansii Strain U3, registration number NM 99 / 06216 (For example, by Botry-Zen Ltd, New Zealand Provided BOTRY-ZEN ® and from BioWorks, Inc. of BOTRYSTOP ® (B2.84) Verticillium glomeratum ( Verticillium albo-atrum (Previously it was) V. dahliasThe strain WCS850, with accession number WCS850, is deposited in the Central Bureau for FungiCultures (e.g., DUTCH TRIG provided by Tree Care Innovations). ® (B2.86) *Verticillium chrysogenum* ( Verticillium chlamydosporium ); (B2.87) Trichoderma echinococcus strain ICC 012 (also known as Trichoderma harzianum ICC012) (accession number CABI CC IMI 392716) and Trichoderma gems strain (formerly... T. green A mixture of strains ICC080 (accession number IMI 392151) (e.g., BIO-TAM from Isagro USA, Inc.) TM And BIODERMA provided by Agrobiosolde Mexico, SA de CV ® (B2.88) Trichoderma acicularis ( Trichoderma asperelloid ) JM41R (Registration No. NRRL B-50759) (from BASF SE's TRICHO PLUS) ® (B2.89) Aspergillus flavus ( Aspergillus flavus ) strain NRRL 21882 (from Syngenta / ChemChina, referred to as AFLA-GUARD) ® (Products); (B2.90) Chaetoceros horn ( Chaetomium cupreum (Registration No. CABI 353812) (e.g., BIOKUPRUM provided by AgriLife) TM (B2.91) Saccharomyces cerevisiae, particularly strain LASO2 (from Agro-Levureset Dérivés), and cell walls of strain LAS117 (from CEREVISANE in Lesaffre). ® ;ROMEO from BASF SE ® (B2.92) strains from Lesaffre et Compagnie, FR, CNCM numbers I-3936, I-3937, I-3938, and I-3939 (WO 2010 / 086790); Trichoderma strain G-41, formerly known as *Trichoderma viride* (accession number ATCC 20906) (e.g., ROOTSHIELD from BioWorks, US). ® PLUS WP and TURFSHIELD ®PLUS WP); (B2.93) Trichoderma hookeri ( Trichoderma hamatum ), Registration No. ATCC 28012; (B2.94) Powdery mildew strain AQ10, accession number CNCM I-807 (e.g., AQ 10 provided by IntrachemBio Italia). ® (B2.95) *Gnaphalium affine* ( Phlebiopsis gigantea Strain VRA 1992 (from ROTSTOP of Danstar Ferment) ® C); (B2.96) from BASF SE Penicillium steckii (DSM 27859; WO 2015 / 067800); (B2.97) Chaetomium globosum ( Chaetomium globosum (Can be made by Rivale in RIVADIOM) ® (B2.98) Cryptococcus faecium ( Cryptococcus flavescens ), strain 3C (NRRL Y-50378); (B2.99) White Dactylaria (B2.100) Dilophosphora alopecuri (You can Twist Fungus) ® (B2.101) Fusarium oxysporum ( Fusarium oxysporum ), strain Fo47 (available from Natural Plant Protection FUSACLEAN) ® (Obtained); (B2.102) Pseudozyma flocculosa Strain PF-A22 UL (available from Plant Products Co., CA via SPORODEX) ® L obtained); (B2.103) Trichoderma galbana (formerly Trichoderma galbana) T. green ), strain ICC 080 (IMI CC392151 CABI) (available from AGROBIOSOL DE MEXICO, SA DE CV BIODERMA) ® (Obtained); (B2.104) Trichoderma fertile (For example, the BASF product TrichoPlus); (B2.105) Pink aerogenes ( Pink muskrat ), especially strain A3-5 (accession number NRRL 30548); (B2.106) Simplellium woolly ; Biocontrol agents that improve plant growth and / or plant health, which can be combined with the compound complexes of the present invention, include: (C1) Selected from the following bacteria: Bacillus pumilus, particularly strain QST2808 (NRRL No. B-30087); Bacillus subtilis, particularly strain QST713 / AQ713 (NRRL No. B-21661 and described in U.S. Patent No. 6,060,051; available from Bayer CropScience LP, US under SERENADE). ® OPTI or SERENADE ® ASO obtained); Bacillus subtilis, particularly strain AQ30002 (registration number NRRL B-50421 and described in U.S. Patent Application No. 13 / 330,576); Bacillus subtilis, particularly strain AQ30004 (NRRL B-50455 and described in U.S. Patent Application No. 13 / 330,576); *Rhizobium sinense* of alfalfa ( Sinorhizobium meliloti strain NRG-185-1 (from Bayer Crop Science, NITRAGIN) ® GOLD); Bacillus subtilis strain BU1814 (available from BASF SE via TEQUALIS) ® Obtained); Bacillus subtilis rm303 (from Biofilm Crop Protection's RHIZOMAX) ® ); Bacillus amyloliquefaciens pm414 (LOLI-PEPTA from Biofilm Crop Protection) ® ); Bacillus mycosis fungoides BT155 (NRRL No. B-50921), Bacillus mycosis fungoides EE118 (NRRL No. B-50918), Bacillus mycosis fungoides EE141 (NRRL No. B-50916), Bacillus mycosis fungoides BT46-3 (NRRL No. B-50922), Bacillus cereus ( Bacillus cereus Family member EE128 (NRRL number B-50917), Bacillus thuringiensis ( Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), Bacillus cereus family member EE349 (NRRL No. B-50928), Bacillus amyloliquefaciens SB3281 (ATCC # PTA-7542; WO 2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available from Novozymes via QUIKROOTS) ® Obtained); Bacillus thuringiensis ( Bacillus firmus ), especially strain CNMC I-1582 (e.g., VOTIVO from BASF SE) ®); Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD from Bayer Crop Science, DE). ® ); Bacillus amyloliquefaciens, especially strain IN937a; Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL from ABiTEP, DE). ® ); Bacillus amyloliquefaciens BS27 (registration number NRRL B-5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation via Quartzo). ® (WG), PRESENCE ® (WP) obtained); Bacillus cereus, particularly strain BP01 (ATCC 55675; e.g., MEPICHLOR from Arysta Lifescience, US). ® ); Bacillus subtilis, especially strain MBI 600 (e.g., SUBTILEX from BASF SE) ® ); Slow-growing soybean rhizobia ( Bradyrhizobium japonicum (e.g., OPTIMIZE from Novozymes) ® ); Mesorhizobium chickpea (e.g., NODULATOR from BASF SE); Pea rhizobium fava bean biotype ( Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE); *Trichophyton acidophilus* ( Delftia acidivorous ), especially strain RAY209 (e.g., BIOBOOST from Brett Young Seeds). ® ); Lactobacillus ( Lactobacillus sp. (e.g., LACTOPLANT from LactoPAFI) ® ); Polymyxin Bacillus, especially strain AC-1 (e.g., TOPSEED from Green Biotech Company Ltd.) ® ); Pseudomonas proradicus (For example, PRORADIX from Sourcon Padena) ® ); Azotobacter brasiliensis ( Azospirillum brasilense (For example, VIGOR from KALO, Inc.) ® ); Lipotherapeutic Azotoxin ( Azospirillum lipoferum (For example, VERTEX-IF from TerraMax, Inc.) TM ); Zygophyllum demersum ( Azotobacter vinelandii ) and Clostridium pasteuroides ( Clostridium pasteurianumA mixture of (available from Agrinos in INVIGORATE) ® Obtained); Pseudomonas aeruginosa ( Pseudomonas aeruginosa ), especially strain PN1; pea rhizobium ( Rhizobium leguminosarum ),in particular by vice versa Strain Z25 (accession number CECT 4585); *Dinozoobacterium stalkum* ( Azorhizobium caulinodans ), especially strain ZB-SK-5; Azotobacter brownii ( Azotobacter chroococcum ), especially strain H23; Azotobacter vesiculosus, especially strain ATCC 12837; Bacillus sicca ( Siamese Bacillus ), especially strain KCTC 13613T; Bacillus tekirae ( Bacillus tequilaensis ), especially strain NII-0943; Serratia marcescens ( Serratia marcescens ), especially strain SRM (accession number MTCC 8708); species of the genus Thiobacterium ( Thiobacillus sp. (e.g., CROPAID from Cropaid Ltd UK) ® );and (C2) Selected from the following fungi: Paecilomyces lilacinus ( Purple cilium lilacinum (formerly known as Paecilomyces lilacinus) Paecilomyces lilacinus Strain 251 (AGAL 89 / 030550; e.g., BioAct from BayerCropScience Biologics GmbH), Penicillium ( Penicillium bilaii ), strain ATCC 22348 (e.g., JumpStart from Acceleron BioAg) ® ), yellow Demodex, strain V117b; Trichoderma viride strain CNCMI-1237 (e.g., Esquive® WP from Agrauxine, FR), Trichoderma greenis, e.g., strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); Trichoderma viride strain LC52 (also known as Trichoderma viride strain LU132; e.g., Sentinel from Agrim Technologies Limited); Trichoderma viride strain SC1 described in international application PCT / IT2008 / 000196; Trichoderma echinosporioides strain kd (e.g., T-Gro from Andermatt Biocontrol); Trichoderma echinosporioides strain Eco-T (Plant Health Products, ZA); Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert); *Russula verrucosum* ( Myrothecium warty ) strain AARC-0255 (e.g., DiTera™ from Valent Biosciences); Penicillium strain ATCCATCC20851; Pythium oligomangenus ( Pythium oligandrum ) strain M1 (ATCC 38472; e.g., Polyversum from Bioprepraty, CZ); Trichoderma viride strain GL-21 (e.g., SoilGard® from Certis, USA); Verticillium chrysogenum (formerly...) V. dahlias Strain WCS850 (CBS 276.92; e.g., DutchTrig from Tree Care Innovations); *Trichoderma viride*, especially strains V08 / 002387, V08 / 002388, V08 / 002389, and V08 / 002390; *Trichoderma harzianum* strain ITEM 908; *Trichoderma harzianum* strain TSTh20; *Trichoderma harzianum* strain 1295-22; *Pythium oligospermum* strain DV74; Rhizopogon amylopogon (For example, included in Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba (For example, contained in Myco-Sol from Helena Chemical Company); and Trichoderma viride strain GI-3; Insecticidal biocontrol agents, selected from: (D1) Selected from the following bacteria: Bacillus thuringiensis subsp. tumefaciens ( Bacillus thuringiensis subsp. aizawai ), especially strain ABTS-1857 (SD-1372; e.g., XENTARI from Valent BioSciences). ® ); Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC (a subsidiary of Mitsui & Co.); Bacillus spheroidae ( Spherical Bacillus ), especially serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX from Valent BioSciences, US). ® ); Bacillus thuringiensis Kurstak subsp. from Becker Microbial Products, IL ( Bacillus thuringiensis subsp. Bacillus thuringiensis (Bt) strain BMP 123; Bacillus thuringiensis subsp. niger, particularly serotype H-7 (e.g., FLORBAC from Valent BioSciences, US). ®WG); Bacillus thuringiensis Kurstak subspecies strain HD-1 (e.g., DIPEL from Valent BioSciences, US) ® Bacillus thuringiensis Kurstak subspecies BMP 123, supplied by Becker Microbial Products, IL; Bacillus thuringiensis Israel (ES); Bacillus Thuringian, Israeli Strain BMP 144 (e.g., AQUABAC supplied by Becker Microbial Products IL) ® ); Burkholderia species ( Burkholderia spp. ),in particular Burkholderia rhinojensis strain A396 (also known as Burkholderia rhinojensis Strain MBI 305 (accession numbers NRRL B-50319; WO2011 / 106491 and WO 2013 / 032693; e.g. MBI-206 TGAI and ZELTO from Marrone Bio Innovations) ® ); active purple bacteria ( Chromobacterium subtsugae ), especially strain PRAA4-1T (MBI-203; e.g., GRANDEVO from Marrone Bio Innovations ® ); milky white pathogenic bacteria ( Paenibacillus baby girl (Previously it was grub lactea) Bacillus popilliae ); for example, Milky Spore Powder from St. Gabriel Laboratories TM and Milky Spore Granular TM ); Bacillus thuringiensis subsp. Israel ( Bacillus thuringiensis subsp. Israeli (Serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC provided by Valent BioSciences, US) ® ); Bacillus thuringiensis Kurstak subsp. ( Bacillus thuringiensis var. kurstaki ) strain EVB-113-19 (e.g., BIOPROTEC from AEFGlobal) ® ); Bacillus thuringiensis subsp. A ( Bacillus thuringiensis subsp. of darkness ) strain NB 176 (SD-5428; e.g., NOVODOR from BioFa DE) ®FC); Bacillus thuringiensis subsp. Japaneseis ( Bacillus thuringiensis var. japonicus Bacillus thuringiensis strain Buibui; Bacillus thuringiensis Kurstak subspecies strain ABTS 351; Bacillus thuringiensis Kurstak subspecies strain PB 54; Bacillus thuringiensis Kurstak subspecies strain SA 11; Bacillus thuringiensis Kurstak subspecies strain SA 12; Bacillus thuringiensis Kurstak subspecies strain EG 2348; Bacillus thuringiensis Kolmer subspecies ( Bacillus thuringiensis var . Colmeri (e.g., TIANBAOBTC provided by Changzhou Jianghai Chemical Factory); Bacillus thuringiensis subsp. tsunamis strain GC-91; Serratia entomophila (For example, INVADE provided by Wrightson Seeds) ® Serratia marcescens (); Serratia marcescens ), especially strain SRM (accession number MTCC 8708); and Wolbachia ( Wolbachia pipientis ZAP strains (e.g., ZAP MALES from MosquitoMate) ® );and (D2) Selected from the following fungi: *Cyclocarya rosea* ( Isaria fumosorosea (formerly known as *Paecilomyces rosenbergii*) Paecilomyces fumosoroseus )) Strain apopka 97; Beauveria bassiana ( Beauveria bassiana ) strain ATCC 74040 (e.g., NATURALIS from Intrachem Bio Italia) ® ); Beauveria bassiana strain GHA (accession number ATCC74250; e.g., BOTANIGUARD from Laverlam International Corporation). ® ES and MYCONTROL-O ® ); Zoophtora radicans Metarhizium anisopliae (Roberts) Metarhizium robertsii )15013-1 (deposited under NRRL registry 67073), *Metarhizium anisopliae* Roberts 23013-3 (deposited under NRRL registry 67075), and *Metarhizium anisopliae* ( Metarhizium anisopliae )3213-1 (deposited under NRRL registry 67074) (WO 2017 / 066094; Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (registration number DSM 24665). Among these, Apopka 97 of *Cladosporium flavum* (formerly known as *Paecilomyces flavum*) is particularly preferred; (E) Selected from the following viruses: Cotton Brown Leaf Roller ( Adoxophyes orana (Summerfruit tortrix) Granulovirus (GV), Apple Peel Roller ( Cydia pomonella (codling moth) granulovirus (GV), cotton bollworm ( Helicoverpa armigera (cotton bollworm) nucleopolyhedrovirus (NPV), beet armyworm ( Beet armyworm (beet armyworm) mNPV, fall armyworm ( Spodoptera fall armyworm (fall armyworm) mNPV and sea gray-winged moth ( Egyptian cotton leafworm (African cotton leafworm) NPV; (F) Bacteria and fungi that can be added to plants, plant parts, or plant organs as "inoculants" and promote plant growth and health through their specific properties. Examples include: *Agrobacterium* (…). Agrobacterium species ), stem nodule nitrogen-fixing rhizobia ( Azorhizobium caulinodans ), Azospirobacter genus ( Azospirillum species ), genus of nitrogen-fixing bacteria ( Azotobacter species ), Slow-growing rhizobia ( Bradyrhizobium species Burkholderia, especially Burkholderia cepacia. (Burkholderia cepacia (formerly known as Pseudomonas cepacia) Pseudomonas cepacia ), genus *Macrocystis* ( Gigaspora species )or Gigaspora monosporum Globulus genus ( Glomus species ), genus *Tetraphyta* ( Laccaria species Lactobacillus brunelli ( Lactobacillus buchneri ), genus *Gloydiomycium* Paraglomus species ), Pisolithus tinctorus Pseudomonas spp. ( Pseudomonas species Rhizobium ( ) Rhizobium species ), especially clover rhizobia ( Rhizobium trifolii ), genus *Pleurotus* Rhizopogon species ), genus *Luffa* ( Scleroderma species ), Boletus genus ( Suillus species ) and Streptomyces ( Streptomyces species );as well as (G) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biocontrol agents: for example, garlic ( Garlic ), wormwood ( Wormwood), azadirachtin, Biokeeper WP, Cassia nigricans Bitter bark vine ( Celastrus angulatus ), Chenopodium anthelminticum Chitin, Armour-Zen, European scaly fern ( Dryopteris filix- mas ), Asking for help ( Field horsetail Fortune Aza, Fungastop, Heads Up (quinoa saponin extract) Chenopodium quinoa saponin extract), pyrethrum ( Pyrethrum ) / Pyrethroid ( Pyrethrins ), Surinamese kusa ( Quassia amara ), Oak ( Oak ), soap tree ( Quillaja ), Regalia, "Requiem™ Insecticide", rotenone, ryanodine ( Ryania ) / ryanodine, comfrey ( Symphytum officinale Artemisia ( ) Tansy ), thymol, Triact 70, TriCon, Nasturtium , large nettle ( Stinging nettle Veratrin, Ginkgo biloba mistletoe ( Viscum album ), Brassicaceae ( Brassicaceae Extracts (especially rapeseed powder or mustard powder), and bioactive insecticides / miticides obtained from olive oil, particularly those with a carbon chain length of C... 16 -C 20 Unsaturated fats / carboxylic acids are used as active ingredients, for example, in products marketed under the name FLiPPER®.

[0190] The compounds and compositions of formula (I) of the present invention can be combined with one or more active ingredients of selective insecticides, acaricides and nematicides.

[0191] "Insecticidal agent" and the term "insecticide" refer to the ability of a substance to increase the mortality rate of insects or inhibit their growth rate. As used herein, the term "insect" includes all organisms in the class Insecta.

[0192] "Nematicides" and "nematicides" refer to substances that increase the mortality rate of nematodes or inhibit their growth rate. Generally, the term "nematode" encompasses the eggs, larvae, juveniles, and mature forms of the organism.

[0193] "Acaricide" and "acaricide" refer to substances that increase the mortality rate of ectoparasites belonging to the class Arachnida and subclass Acari, or inhibit their growth rate.

[0194] Examples of insecticides, acaricides, and nematicides that can be mixed with compounds and compositions of formula (I) of the present invention are as follows: (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, including alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, and furathiocarb. b) Isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, such as acephate, azamethiphos, and ethyl glutathione. zinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, didrotophos, dimethoate (d... imethoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester, isoxathion.Malathion, mecarbam, methamidophos, methidathion, mevinphos, monocotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pyrimidine phosphate The following are listed as examples of insecticides: imiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion.

[0195] (2) GABA-gated chloride channel blockers, such as cyclopentadiene-organochlorines, such as chlordane and endosulfan, or fiproles, such as ethiprole and fipronil.

[0196] (3) Sodium channel modulators, such as pyrethroids, including acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, and trifluralin. Cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, cypermethrin Fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer] ], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin, or DDT, or methoxychlor.

[0197] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[0198] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosides, such as spintoram and spinosad.

[0199] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0200] (7) Juvenile hormone analogues, such as hydroprene, kinoprene and methoprene, or fenoxycarb, or pyriproxyfen.

[0201] (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generating agents, such as diazomet and metam.

[0202] (9) Chordonal organ modulators, such as pymetrozine or flonicamid.

[0203] (10) Mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin, or etoxazole.

[0204] (11) Insect intestinal membrane microbial disruptors, such as Bacillus thuringiensis subsp. Israel (Bt). Bacillus thuringiensis subspecies israelensis ), Bacillus spheroidae ( Bacillus sphaericus Bacillus thuringiensis subsp. tumefaciens ( Bacillus thuringiensis subspecies aizawai ), Bacillus thuringiensis Kurstak subspecies ( Bacillus thuringiensis subspecies kurstaki ), Bacillus thuringiensis subsp. A ( Bacillus thuringiensis subspecies tenebrionis ), and the following B.t. Plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[0205] (12) Inhibitors of mitochondrial ATP synthase, such as ATP interfering agents, such as diafenthiuron; or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide; or propargite, or tetradifon.

[0206] (13) By uncoupling agents that interrupt the oxidative phosphorylation of the proton gradient, such as chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0207] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.

[0208] (15) Type O chitin biosynthesis inhibitors, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0209] (16) Type I chitin biosynthesis inhibitors, such as buprofezin.

[0210] (17) Molting disruptors (especially for Diptera, i.e., dipteran insects), such as cyromazine.

[0211] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0212] (19) Octopus amine receptor agonists, such as amitraz.

[0213] (20) Inhibitors of electron transport in mitochondrial complex III, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[0214] (21) Inhibitors of electron transport in mitochondrial complex I, such as METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[0215] (22) Voltage-dependent sodium channel blockers, such as indoxacarb and metaflumizone.

[0216] (23) Acetyl-CoA carboxylase inhibitors, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0217] (24) Inhibitors of electron transport in mitochondrial complex IV, such as phosphine, such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides, such as calcium cyanide, potassium cyanide and sodium cyanide.

[0218] (25) Inhibitors of electron transport in mitochondrial complex II, such as β-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and carboxanilides, such as pyflubumide.

[0219] (28) Lanni base receptor modulators, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[0220] Other active compounds include, for example, afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, chlorpyrifos, cryolite, and cyclopropionate. Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, ε-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Flupyridamole Fluopyram, Flularananer, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Acetaminophen Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Triflumezopyrim, and iodomethane; and also based on Bacillus thuringiensis (… Bacillus firmus(I-1582, BioNeem, Votivo) formulations, and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (as per WO2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl) methyl ketone (as per WO2003 / 106457) (CAS 885026-50-6) 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (as per WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (as per WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (as per EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (obtained from WO2004 / 099160) (CAS 792914-58-0), PF1364 (obtained from JP2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (obtained from WO2012 / 029672) (CAS 1363400-41-2), ( 3E )-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-prop-2-one (as determined by WO2013 / 144213) (CAS 1461743-15-6) N -[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1 H 5-Pyrazole-5-carboxamide (as determined by WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro- N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (as known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl- N -(cis-1-oxo-3-thionylbutane)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl- N -(trans-1-oxo-3-thionecyclobutane)-benzamide and 4-[(5 S )-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl- N -(cis-1-oxo-3-thionecyclobutane)benzamide (as determined by WO 2013 / 050317 A1) (CAS 1332628-83-7) N -[3-chloro-1-(3-pyridyl)-1 H -pyrazole-4-yl]- N -Ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide, (+)- N -[3-chloro-1-(3-pyridyl)-1 H -pyrazole-4-yl]- N -Ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)- N -[3-chloro-1-(3-pyridyl)-1 H -pyrazole-4-yl]- N -Ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (as known from WO2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2 E )-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1 H -Pyrazole-3-carboxynitrile (as known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo- N -[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1 H-Pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N -[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1 H -Pyrazole-5-carboxamide (as determined by WO 2012 / 034403 A1) (CAS 1268277-22-0), N -[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1 H -Pyrazole-5-carboxamide (as per WO 2011 / 085575A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (as per CN 101337940 A) (CAS 1108184-52-6); (2 E )-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene]- N -[4-(difluoromethoxy)phenyl]-hydrazinoamide and 2( Z )-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene]- N -[4-(difluoromethoxy)phenyl]-hydrazinoamide (as known from CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1 H -benzimidazole-2-yl)phenyl-cyclopropane carboxylate (as known from CN 103524422 A) (CAS1542271-46-4); (4a S )-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2- e [1,3,4]Oxadiazine-4a(3 H 6-Deoxy-3-methyl formate (as known from CN 102391261 A) (CAS1370358-69-2); O -Ethyl-2,4-di- O -methyl, 1-[ N -[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1 H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (as known from US 2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8- trans- )-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8- cis- )-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (as obtained from WO 2007 / 040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propionamide (as obtained from WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1 H-Pyrazole-5-carboxamide (as per CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxane-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (as per WO 2013 / 115391 A1) (CAS1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4,5]dec-3-en-2-one (as per WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (as obtained from WO 2014 / 187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (as obtained from WO 2010 / 066780 A1, WO2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1 H [N(-pyridyl]-2,2,2-trifluoroacetamide (obtained from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N( E )]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridyl]-2,2,2-trifluoroacetamide (obtained from WO2016005276 A1) (CAS 1689566-03-7), [N( Z )]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridyl]-2,2,2-trifluoroacetamide (CAS 1702305-40-5), 3- endo -3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridyl]oxy]-9-azabicyclo[3.3.1]nonane (as known from WO 2011 / 105506 A1, WO 2016 / 133011 A1) (CAS 1332838-17-1).

[0221] Examples of herbicides that can be mixed with compounds and compositions of formula (I) of the present invention include: Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7-) Fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrol, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin Azimsulfuron, beflubutamid, benzolin, benzolin-ethyl, benzfluralin, benzuresate, benzsulfuron-methyl, benzulide, benzazone, benzobicyclon, benzofenap, and bicycline. Herbicides including opyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, and bromoxynil-potassium.Bromoxynil-heptanoate and octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, and flufentrazone ethyl flufentrazone. (carfentrazone-ethyl), chloramben, chlorbromuron, 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methanesulfonyl)benzoyl}-1,3-dimethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylic acid ester, chlorfenac, chlorfenac-sodium, oat ester (chlorfenprop), chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohexyl-2-en-1-one, 4-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}-1-ethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4- Carboxylic acid esters, chlorophthalim, chlorotoluron, chlorthal-dimethyl, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolium-2-one, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafopClodinafop-propargyl, clonzone, clonprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydi m), cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butoxyethyl ester (2,4-D-butotyl), 2,4-D-butyl ester (2,4-D-butyl), 2,4-D-dimethylammonium salt (2,4-D-diolamin), 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt, 2,4-D-potassium salt, 2,4-D-triisopropanolammonium salt And 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, dichlorprop, dichlorprop, dichlorpropamide rprop-P), diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn.Dimethenamid, dimethenamid-P, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 1,3-dimethyl-4-[2-(methanesulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylic acid ester, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat Diquat-dibromid, dithiopyr, diuron, DMPA, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, etiozin, ethofumesate, ethoxyfen, ethaloxyfen ethyl ester ethyl oxyfen-ethyl, ethoxysulfuron, etobenzanid, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, F-9960, F-5231 (i.e., N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6- (Trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methylFlazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Fluf... Enpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, and fluoroglycofen. Fluorosulfuron-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet methyl ester et-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-sodium, glyphosate, glyphosate-ammoniumGlyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, and glyphosate-trimesium; H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylthiophosphoramide ester); halauxife (a type of chloropyridine acid). n), halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-meth yl), hexazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetic acid ester), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidine-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidine-2-one, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-5-yl) methyl ketone, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin- 2,4(1H,3H)-Diketone, Imidacloprid (imazamethabenz), Imidacloprid-methyl (imazamethabenz-methyl), Imidacloprid (imazamox), Imidacloprid-ammonium (imazamox-ammonium), Imidacloprid (imazapic), Imidacloprid-ammonium (imazapic-ammonium), Imidacloprid (imazapyr), Imidacloprid-isopropylammonium (imazapyr-isopropylammonium), Imidacloprid-quinoline acid (imazaquin), Imidacloprid-quinoline ammonium (imazaquin-ammonium)Imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium, and ioxynil-sodium, triazole oxychloride (ipfencarbazone), isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactoferrin, lenacil, linuron, MCPA, MCPA-butoxyethyl ester MCPA-butotyl, MCPA-dimethylammonium salt, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium salt, MCPA-potassium salt and MCPA-sodium salt, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid sodium (mecoprop-sodium) and 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), purified 2-methyl-4-chloropropionic acid (mecoprop-P), purified 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-P-butotyl), purified 2-methyl-4-chloropropionic acid dimethyl ester Mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, and metam.Metamethop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, 2-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)cyclohexyl-1,3-dione, methyl isothiocyanate, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-5-yl)carbonyl]-1H-pyrazol-5-ylpropyl-1-sulfonate, metobromuron, metolachlor, S-metolachlor or), metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinat, monolinuron, monosulfuron-ester, MT-5950 (N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide), NGGC-011, napropamide, NC-310 ([5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl) methyl ketone), neburon, nicosulfuron, nonanoic acid acid (pelargonicacid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham.Picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, chlorpyrifos (propazine), propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotol e), pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid ), pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-PQuizalofop-P-ethyl, quizalofop-P-tefuryl, QYM-201, QYR-301, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfurtrazone, sulfometuron, sulfometuron methyl ester methyl), sulfosulfuron, SYN-523, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, cyclosulfonone (tembotrione), tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron methyl ester (t) Hifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron-methyl, tribensulfuron, tribensulfuron-methyl, triclopyr, trietazineTrifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline).

[0222] Examples of plant growth regulators are as follows: Acibenzolar, benzothiadiazole (acibenzolar-S-methyl), 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium, and endothal mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid acid), antidote, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazine, mepiquat chloride, 1-methylcyclopropene, methyl jasmonic acid, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-β-aminopropionic acid, N-phenylphthalamic acid acid), prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0223] Examples of safe agents that can be mixed with compounds and compositions of formula (I) of the present invention include: for example, benoxacor, cloquintocet (-mexyl) , cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl) , fenclorim , flurazole, fluxofenim, furilazole, isoxadifen (-ethyl) , mefenpyr (-diethyl) , naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS) 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0224] Examples of nitration inhibitors that can be mixed with compounds and compositions of formula (I) of the present invention are selected from: 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazol-1-yl)succinic acid, 3,4-dimethylpyrazolium glycolate, 3,4-dimethylpyrazolium citrate, 3,4-dimethylpyrazolium lactate, 3,4-dimethylpyrazolium mandelate, 1,2,4-triazole, 4-chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, etc. H-pyrazol-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazol-1-yl)methyl)formamide, N-((4-chloro-3(5)-methyl-pyrazol-1-yl)methyl)formamide; reaction adducts of dicyandiamide, urea and formaldehyde, triazonyl-dicyandiamide adduct, formaldehyde-dicyandiamide adduct, 2-cyano-1-((4-oxo-1,3,5-triazinyl-1-yl)methyl)guanidine, 1-((2-cyanoguanidinyl)methyl)urea, 2-cyano-1-((2-cyanoguanidinyl)methyl)guanidine, 2-chloro-6 3-(trichloromethyl)-pyridine (nitrapyrin or N-serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, products based on neem, linoleic acid, and α-linolenic acid, methyl p-coumarate, methyl ferulic acid, methyl 3-(4-hydroxyphenyl)propionate, karanjin, brachialacton, p-benzoquinone sorgoleone), 4-amino-1,2,4-triazole hydrochloride, 1-amino-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (terrazole, etridiazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazole thiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allyl thiourea, chlorate and zinc sulfate.

[0225] The compounds and compositions of formula (I) of the present invention can be combined with one or more agriculturally beneficial reagents.

[0226] Examples of beneficial agents in agriculture include: biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulating molecules, biomolecules, soil conditioners, nutrients, plant nutrient enhancers, etc., such as lipid-chitosan oligosaccharides (LCO), chitosan oligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonic acid salts), cytokinins, plant growth hormones, gibberellins, abscisic acid, ethylene, brassinosteroids, salicylates, macronutrients and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and beneficial microorganisms (e.g., Rhizobium spp.). Rhizobium spp.), genus *S.*, *S.*, *S.* Bradyrhizobium spp.), *Rhizobium sinense* ( Sinorhizobium spp.), nitrogen-fixing rhizobia ( Azorhizobium spp.), Globulus genus ( Glomus spp.), genus *Macrocystis* ( Gigaspora spp.), Hymenoscyphous spp., genus *Pteris* ( Oidiodendron spp.), genus *Tetranychus* ( Laccaria spp.), genus *Lycoperdon* ( Pisolithus spp.), genus *S.* (S ...) Rhizopogon spp.), genus *Lycoperdon* ( ... Scleroderma spp.), Rhizoctonia spp. ( Rhizoctonia Acinetobacter spp.), Acinetobacter spp. Acinetobacter spp.), Arthrobacter spp. Arthrobacter spp.), Nematode-trapping fungi ( Arthrobotrys spp.), Aspergillus ( Aspergillus spp.), Azospirillum ( Azospirillum spp.), Bacillus spp. Bacillus spp.), Burkholderia ( Burkholderia spp.), Candida spp. Candida spp. ), Aureomyces ( Chryseomonas spp.), Enterobacteriaceae ( Enterobacter spp.), Penicillium genus ( Eupenicillium spp.), Microbacteria ( Exiguobacterium spp.), Klebsiella spp. Klebsiella spp.), Krüverella ( Kluyvera spp.), Microbacterium spp. ( Microbacterium spp.), Mucor ( Mucor spp. ), Penicillium genus ( Paecilomyces spp. ), Bacillus spp. ( Paenibacillus spp.), Penicillium genus ( Penicillium spp.), Pseudomonas (Pseudomonas spp.), Serratia ( Serratia spp.), Oligotrophomonas spp. Stenotrophomonas spp.), Streptomyces ( Streptomyces spp.), Streptomyces spp. ( Streptosporangium spp.), Swaminathanella spp. Swaminathania spp.), Thiobacillus spp. Thiobacillus spp.), Torulospora spp., Vibrio genus ( Vibrio spp.), Flavobacterium ( Xanthobacter spp.), Xanthomonas ( Xanthomonas (spp.), etc.), and their combinations.

[0227] Method and use The compounds and compositions of formula (I) of the present invention have potential antimicrobial activity and / or plant defense modulation potential. They can be used to control unwanted microorganisms on plants, such as unwanted fungi and bacteria. In particular, they can be used for crop protection (they control microorganisms that cause plant diseases) or for protecting materials (e.g., industrial materials, timber, stored goods) as described in more detail below. More specifically, the compounds and compositions of formula (I) of the present invention can be used to protect seeds, germinating seeds, newly emerging seedlings, plants, plant parts, fruits, harvested articles, and / or the soil in which plants grow from unwanted microbial contamination.

[0228] The article described Control or controlling This includes preventative, therapeutic, and eradicative treatment of unwanted microorganisms. Unwanted microorganisms These could be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes, or plant pathogenic fungi. As detailed below, these plant pathogenic microorganisms are causative agents of a broad spectrum of plant diseases.

[0229] More specifically, the compounds and compositions of formula (I) of the present invention can be used as fungicides. For the purposes of this invention, the term "fungicide" refers to a compound or composition that can be used in crop protection to control unwanted fungi and / or control oomycetes, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes.

[0230] The compounds and compositions of formula (I) of the present invention can also be used as antibacterial agents. In particular, they can be used in crop protection, for example, to control unwanted bacteria such as those belonging to the families Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[0231] The compounds and compositions of formula (I) of the present invention can also be used as antiviral agents in crop protection. For example, the compounds and compositions of formula (I) of the present invention can be effective against diseases caused by plant viruses, such as tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leafcurl virus (VLCV), tobacco nervilia mosaic virus (TVBMV), tobacco necrotic dwarf virus (TNDV), tobacco streak virus (TSV), potato virus X (PVX), potato viruses Y, S, M and A, potato acuba mosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf-roll virus (PLRV), and alfalfa mosaic virus. The following viruses are listed: AMV (Cucumber Mosaic Virus), CMV (Cucumber Mottle Mosaic Virus), CGMMV (Cucumber Green Mottle Mosaic Virus), Cucumber Yellowsvirus (Cucumber Yellows Virus), WMV (Watermelon Mosaic Virus), TSWV (Tomato Spotted Wilt Virus), TomRSV (Tomato Ringspot Virus), SCMV (Sugarcane Mosaic Virus), RHU (Rice Dwarf Virus), RHU (Rice Stripe Virus), RHU (Rice Black-streaked Dwarf Virus), SMoV (Strawberry Mottle Virus), SVBV (Strawberry Veinbanding Virus), and SVBV (Strawberry Mild Yellow Edge Virus).Yellow edge virus (SMYEV), strawberry crinkle virus (SCrV), broad bean wilt virus (BBWV), and melon necrotic spot virus (MNSV).

[0232] The present invention also relates to a method for controlling unwanted microorganisms (such as unwanted fungi, oomycetes and bacteria) on plants, comprising the step of applying at least one compound of formula (I) of the present invention or at least one composition thereof to the microorganism and / or its habitat (applied to the plant, plant part, seed, fruit or soil in which the plant grows).

[0233] In particular, the present invention relates to a method for controlling harmful microorganisms in crop protection and material protection, wherein at least one compound and / or composition of formula (I) of the present invention is applied to the harmful microorganisms and / or their habitats.

[0234] Harmful microorganisms that can be controlled by this method are described in more detail in the "Pathogens" section below.

[0235] Preferably, the harmful microorganism is a pathogenic oomycete or plant pathogenic fungus selected from the following: *Monophyllum* genus (…). Podosphaera ) species, genus of monothecota ( Sphaerotheca ) species, genus *Hylocereus* ( Uncinula ) species, genus *Russula* ( Gymnosporangium ) species, genus Camel rust ( Hemileia ) species, genus of rust fungi ( Phakopsora ) species, genus Stipe rust ( Puccinia ) species, genus *Russula* ( Uromyces ) species, genus *White Rust* ( Albugo ) species, genus *Peronospora* Bremia ) species, genus Peronospora ( Peronospora ) species, Phytophthora ( Phytophthora ) species, genus Peronospora ( Plasmopara ) species, genus *Pseudomonas* Pseudoperonospora ) species, genus Pythium ( Pythium ) species, Alternaria genus ( Alternaria ) species, Cercospora ( Cercospora ) species, genus Cladosporium ( Cladiosporum ) species, genus Cyclospora ( Cochliobolus ) species, genus Cladosporium ( Corynespora )kind, Cycloconium Species, genus Interstellate ( Diaporthe ) species, genus *Cryptococcus* ( Elsinoe ) species, genus *Palmaria* ( Gloeosporium ) species, genus *Ceratophyllum* (Glomerella ) species, genus *Plasmodium* ( Guignardia ) species, Micrococcus genus ( Leptosphaeria ) species, genus Giant Seat Shell ( Magnaporthe ) species, Micrococcus genus ( Microdochium ) species, genus Coccidioides ( Mycosphaerella ) species, genus *Cyclocarya* ( Phaeosphaeria ) species, genus *Sclerotium* (Pyrenophora ) species, genus *Pseudomonas* ( Ramularia ) species, genus *Rhizophora* ( Rhynchosporium ) species, genus *Syngonium* ( Septoria ) species, genus Polysporus ( Stagonospora ) species, genus *Russula* ( Typhula ) species, genus *Nepeta* ( Venturia ) species, genus *Foucault* ( Corticium ) species, Fusarium genus ( Fusarium ) species, genus *Tetranychus* Gaeumannomyces ) species, genus Plasmodium ( Plasmodiophora ) species, Rhizoctonia genus ( Rhizoctonia ) species, genus *Cladosporium* Sarocladium ) species, genus Microsclerotium ( Sclerotium )kind, Tapesia Species, Rhizophora genus ( Thielaviopsis ) species, Aspergillus genus ( Aspergillus ) species, genus Clavicipitaceae ( Claviceps ) species, genus Fusarium ( Gibberella )kind, Monographella Species, genus Polysporus ( Stagonospora ) species, genus Ustilago spp. Sphacelotheca ) species, genus *Ustilago maydis* Tilletia ) species, genus *Ustilago maydis* Urocystis ) species, genus Ustilago ( Ustilago ) species, genus *Streptococcus* ( Monilinia ) species, Penicillium genus ( Penicillium ) species, Rhizopus genus ( Rhizopus ) species, genus Sclerotium ( Sclerotinia ) species, Verticillium genus ( Verticilium ) species, genus Hymenops ( Aphanomyces ) species, genus Dicellae ( Ascochyta ) species, genus Cladosporium ( Cladosporium ) species, genus *Cyclophorus* ( Macrophomina ) species, genus Stem-point mold ( Phoma ) species, genus *Pseudomonas* Phomopsis ) species, genus Pyrethrum ( Pyricularia ) species, Verticillium genus ( Verticillium ) species, genus *Cryptostoma* ( Nectria ) species, genus of exobasidium ( Exobasidium ) species, genus Exocystis ( Taphrina )kind, EscaSpecies, Ganoderma ( Ganoderma ) species, genus Helicobacter ( Helminthosporium ) species, Xanthomonas genus ( Xanthomonas ) species, Pseudomonas genus ( Pseudomonas ) species, Erwinia genus ( Erwinia ) species, genus Bacillus phloem Liberibacter ) species, genus *Xylomycetes* Xyella ) species, Ralstonia solanacearum genus ( Ralstonia ) species, Dictyotis genus ( Dickeya ) species, Corynebacterium genus ( Clavibacter ) species, genus Streptomyces ( Streptomyces )kind, Colletotrichum gloeosporoides dematium var. truncatum Funnel-shaped mold ( Choanephora infundibulifera ) trispora (synonym) , Dactuliophora glycines Soybean endospermia ( Drechslera glycini ), Clover Small Glossy Shell ( Leptosphaerulina trifolii ), Soybean leaf spot ( Phyllosticta sojaecola ), soybean powdery mildew ( Microsphaera diffusa Soybean red leaf spot pathogen ( Pyrenochaeta glycines ), Soybean scab rounds ( Sphaceloma glycines ), creeping mold ( Stemphylium botryosum ), Wild Lily Red Shell ( Calonectria crotalariae ), Mycoleptodiscus terrestris 、Invasion of new red shell ( Neocosmospora vasinfecta ) and soybean stem brown rot fungus ( Phialophora gregata ).

[0236] More preferably, the harmful microorganism is a pathogenic oomycete or plant pathogenic fungus selected from the following: Alternaria ( Alternaria ) species, genus Pyrethrum ( Pyricularia ) species, genus of monothecota ( Sphaerotheca ) species and Fusarium genus ( Fusarium )kind.

[0237] More preferably, the harmful microorganism is a pathogenic oomycete or plant pathogenic fungus selected from the following: Erythrinae monotypicum ( Sphaerotheca fuliginea Alternaria ( Alternaria alternata ), Inari spores ( Pyricularia oryzae ), Brassica oleracea ( Alternaria brassicae ) and yellow Fusarium ( Fusarium culmorum ).

[0238] Typically, when the compounds and compositions of formula (I) of the present invention are used in therapeutic or protective methods for controlling plant pathogenic fungi and / or plant pathogenic oomycetes, they are applied in an effective and plant-compatible amount to the plant, plant parts, fruits, seeds, or to the soil or substrate in which the plant grows. Suitable substrates that can be used for cultivating plants include inorganic-based substrates, such as mineral wool, especially rock wool, perlite, sand, or gravel; organic substrates, such as peat, pine bark, or sawdust; and petroleum-based substrates, such as polymer foam or plastic beads. an effective and plant-compatible amount This means a quantity sufficient to control or destroy fungi present or readily available in farmland without causing any obvious phytotoxic symptoms in the crop. This quantity can vary considerably depending on the fungus being controlled, the type of crop, the crop's growth stage, climatic conditions, and the various compounds or compositions of the present invention used. This quantity can be determined through systematic field trials, to the capabilities of those skilled in the art.

[0239] plants and plant parts The compounds and compositions of formula (I) of the present invention can be applied to any plant or plant part.

[0240] plants This refers to all plants and plant populations, including both desired and unwanted wild plants and crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained through conventional breeding and optimization methods or through biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMOs or transgenic plants) and cultivars of plants that are protected or not protected by plant breeders' rights.

[0241] plant cultivars This should be understood to mean plants that possess new characteristics ("traits") and have been obtained through conventional breeding, mutagenesis, or recombinant DNA techniques. These can be cultivars, varieties, biotypes, or genotypes.

[0242] plant parts It should be understood to refer to all parts and organs of a plant, both above and below ground, such as buds, leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes. Plant parts also include harvested material as well as asexual and sexual propagation material, such as cuttings, tubers, rhizomes, stem cuttings, and seeds.

[0243] Plants that can be treated according to the method of the present invention include: cotton, flax, grapevines, fruits, and vegetables, such as species of the Rosaceae family (…). Rosaceae sp. (For example, pome fruits such as apples and pears, as well as drupes such as apricots, cherries, almonds and peaches, and seedless small fruits such as strawberries.) Ribesioidae sp. , Juglandaceae family, genus and species ( Juglandaceae sp.), Species of the genus Betulaceae ( Betulaceae sp. ), Anacardiaceae family, genus ( Anacardiaceae sp. ), Fagaceae family, genera and species ( Fagaceae sp. ), species of the genus Moraceae ( Moraceae sp. ), Oleaceae family, genus ( Oleaceae sp. ), species of the Actinidiaceae family ( Actinidaceae sp. ), Lauraceae family, genus and species ( Lauraceae sp. ), Musaceae family, genus and species ( Musaceae sp. (e.g., banana trees and banana plantations), species of the Rubiaceae family ( Rubiaceae sp. (e.g., coffee), species of the Theaceae family ( Theaceae sp. ), Species of the family Sterculiaceae ( Sterculiceae sp. ), Rutaceae family, genus and species ( Rutaceae sp. (e.g., lemons, oranges, and grapefruits), species of the Solanaceae family ( Solanaceae sp. (e.g., tomato), lily family genera and species ( Liliaceae sp. ), Asteraceae family, genus and species ( Asteraceae sp. (e.g., lettuce), species of the Apiaceae family ( Umbelliferae sp. ), species of the Brassicaceae family ( Cruciferae sp. ), species of the Chenopodiaceae family ( Chenopodiaceae sp. ), Cucurbitaceae family, genus ( Cucurbitaceae sp. (e.g., cucumber), species of the Allium family ( Alliaceae sp. (e.g., chives, onions), Fabaceae family ( ) Papilionaceae sp. (e.g., peas); major crop plants, such as species of the Poaceae family ( Gramineae sp. (For example, corn, turfgrass, cereals (such as wheat, rye, rice, barley, oats, millet and triticale)), species of the Asteraceae family ( Asteraceae sp. (e.g., sunflower), species of the Brassicaceae family ( Brassicaceae sp. (e.g., white Brussels sprouts, red Brussels sprouts, broccoli, Brussels sprouts, bok choy, kohlrabi, radish, as well as rapeseed, mustard greens, horseradish, and watercress), legume species ( Fabacae sp. (e.g., green beans, peanuts), Fabaceae family genera and species ( Papilionaceae sp. (e.g., soybean), species of the Solanaceae family ( Solanaceae sp. (e.g., potato), species of the Chenopodiaceae family ( Chenopodiaceae sp. (e.g., sugar beets, forage beets, Swiss chards, beetroot); useful and ornamental plants in gardens and forests; and genetically modified varieties of these plants.

[0244] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are resistant to one or more biological stresses, i.e., the plants have better defense against animal and microbial pests (such as nematodes, insects, mites, plant pathogenic fungi, bacteria, viruses and / or viroids).

[0245] Plants and cultivars that can be treated by the methods disclosed above include those that are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, low temperature exposure, heat exposure, osmotic stress, waterlogging, increased soil salinity, enhanced mineral exposure, ozone exposure, strong light exposure, limited nitrogen nutrient use, limited phosphorus nutrient use, and shade.

[0246] Plants and cultivars that can be treated by the methods disclosed above include those characterized by enhanced yield characteristics. Enhanced yield in these plants can result from factors such as improved plant physiology, growth, and development, including water use efficiency, water holding efficiency, improved nitrogen use efficiency, enhanced carbon assimilation, improved photosynthesis, increased germination rate, and accelerated maturation. Yield can also be influenced by improved plant architecture (under stress and non-stress conditions), including but not limited to: earlier flowering, flowering control in hybrid seed production, seedling vigor, plant size, number and spacing of internodes, root growth, seed size, fruit size, pod size, number of pods or spikes, number of seeds per pod or spike, seed quality, enhanced seed plumpness, reduced seed dispersal, reduced pod dehiscence, and lodging resistance. Other yield traits include seed composition, such as carbohydrate content and composition (e.g., cotton or starch), protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability, and better storage stability.

[0247] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are hybrids that have expressed characteristics of heterosis or hybrid vigor, which generally result in higher yields, vigor, health and resistance to biotic and abiotic stresses.

[0248] Transgenic plants, seed treatment, and integration events Compounds of formula (I) can be advantageously used to treat transgenic plants, cultivars, or plant parts that have received genetic material that confers advantageous and / or useful characteristics (traits) to these plants, cultivars, or plant parts. Therefore, it is conceivable to combine the present invention with one or more recombinant traits or transgenic lines, or combinations thereof. For the purposes of this application, a transgenic line is produced by inserting a specific recombinant DNA molecule into a specific location (locus) within the chromosome of a plant genome. This insertion creates a new DNA sequence referred to as a “line,” characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA adjacent to / flanking both ends of the inserted DNA. Such traits or transgenic lines include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, wherein the trait is measured relative to plants lacking such a trait or transgenic line. Specific examples of such advantageous and / or useful traits are better plant growth, vigor, stress tolerance, stand ability, lodging resistance, nutrient uptake, plant nutrition and / or yield, especially improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated ripening, higher yield, higher quality and / or higher nutritional value of harvested products, better storage life and / or processability of harvested products, and enhanced resistance to animal and microbial pests (e.g., insects, arachnids, nematodes, mites, slugs and snails).

[0249] Among the DNA sequences encoding proteins that confer tolerance to harmful substances (particularly insects) on these animals and microorganisms, genetic material from Bacillus thuringiensis will be specifically mentioned, encoding the Bt protein, which is widely documented in the literature and well-known to those skilled in the art. Proteins extracted from bacteria, such as those from the genus *Luminobacterium*, will also be mentioned. Photorhabdus(WO97 / 17432 and WO98 / 08932). Specifically, Bt Cry or VIP proteins, including CryA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF proteins or their toxic fragments, as well as their hybrids or combinations, particularly CryF proteins or hybrids derived from CryF proteins (such as hybrid CryA-CryF proteins or their toxic fragments), CryA-type proteins or their toxic fragments, preferably CryAc proteins or hybrids derived from CryAc proteins (such as hybrid CryAb-CryAc proteins), or CryAb or Bt2 proteins or their toxic fragments, Cry2Ae, Cry2Af, or Cry2Ag proteins or their toxic fragments, CryA.105 proteins or their toxic fragments, and VIP3Aa19, VIP3Aa20, and VIP3A proteins produced in COT202 or COT203 cotton lines, are described in Estruch et al. (1996), Proc Natl Acad Sci. The VIP3Aa protein or its toxic fragment described in US A. 28;93(11):5389-94, and the Cry protein described in WO2001 / 47952, are derived from the genus *Pathogenic Bacillus* (…). Xenorhabdus (as described in WO98 / 50427), Serratia spp. ( Serratia (Especially from Serratia marcescens (S.) entomophila Insecticidal proteins from *Proteobacterium* species, such as the Tc protein from *Proteobacterium* described in WO98 / 08932. This document also includes any variants or mutants of any of the aforementioned proteins that differ from any of the sequences (particularly the sequences of their toxic fragments) in some amino acids (1-10, preferably 1-5), or any variants or mutants of the aforementioned proteins fused with a transport peptide (such as a plasmid transport peptide) or another protein or peptide.

[0250] Another, and particularly emphasized, example of this characteristic is the conferment of tolerance to one or more herbicides (e.g., imidazolinones, sulfonylureas, glyphosate, or phosphinothricin). Among the DNA sequences encoding proteins that confer the characteristic of tolerance to certain herbicides to transformed plant cells and plants, the bar or PAT gene or Streptomyces coelicolor gene conferring tolerance to glufosinate-ammonium herbicide as described in WO2009 / 152359 will be specifically mentioned; genes encoding suitable EPSPS (5-enolpyruvylshikimat-3-phosphat-synthase) conferring tolerance to EPSPS-targeting herbicides (especially to herbicides such as glyphosate and its salts); genes encoding glyphosate-n-acetyltransferase; or genes encoding glyphosate oxidoreductase. Other suitable herbicide tolerance traits include at least one ALS (acetyllactate synthase) inhibitor (e.g., WO2007 / 024782), a mutant Arabidopsis ALS / AHAS gene (e.g., US Patent 6,855,533) encoding a gene that confers tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid) and a gene that confers tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid) monooxygenase.

[0251] Another example of this characteristic is resistance to one or more plant pathogenic fungi, such as Asian soybean rust. In the DNA sequences encoding proteins that confer resistance to such diseases, those from short-haired wild soybean (Glycine max) will be specifically mentioned. glycine tomentella Genetic material of, for example, any of the publicly available registry lines described in WO2019 / 103918: PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256 or PI446961.

[0252] A further and particularly emphasized example of this characteristic is the increased resistance to bacteria and / or viruses due to, for example, systemically acquired resistance (SAR), systemins, phytoalexins, inducers, and resistance genes and the corresponding expressed proteins and toxins.

[0253] The transgenic lines of transgenic plants or plant cultivars that are particularly useful for preferential treatment according to the present invention include line 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), line 1143-14A (cotton, insect control, not preserved, described in WO2006 / 128569); line 1143-51B (cotton, insect control, not preserved, described in WO2006 / 128570); and line 1445 (cotton, herbicide tolerant, not preserved, described in US-A). 2002-120964 or WO2002 / 034946); line 17053 (rice, herbicide resistant, deposited as PTA-9843, described in WO2010 / 117737); line 17314 (rice, herbicide resistant, deposited as PTA-9844, described in WO2010 / 117735); line 281-24-236 (cotton, insect control - herbicide resistant, deposited as PTA-6233, described in WO2005 / 103266 or US-A 2005-216969); line 3006-210-23 (cotton, insect control - herbicide resistant, deposited as PTA-6233, described in US-A 2007-143876 or WO2005 / 103266); line 3272 (maize, quality traits, deposited as PTA-9972, described in WO2006 / 098952 or US-A 2006-230473); line 33391 (wheat, herbicide resistance, deposited as PTA-2347, described in WO2002 / 027004); line 40416 (maize, insect control - herbicide resistance, deposited as ATCC PTA-11508, described in WO 11 / 075593); line 43A47 (maize, insect control - herbicide resistance, deposited as ATCC PTA-11508, described in WO 11 / 075593); PTA-11509 deposited, described in WO2011 / 075595; line 5307 (maize, insect control, deposited as ATCCPTA-9561, described in WO2010 / 077816); line ASR-368 (bent grass, herbicide resistant, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); line B16 (maize, herbicide resistant, not deposited, described in US-A 2003-126634); line BPS-CV127-9 (soybean, herbicide resistant, deposited as NCIMB 41603, described in WO2010 / 080829); line BLR1 (rapeseed, restoring male sterility, deposited as NCIMB 41603, described in WO2010 / 080829). 41193 (Collection, recorded in WO2005 / 074671)Strain CE43-67B (cotton, insect control, deposited as DSMAC 2724, described in US-A 2009-217423 or WO2006 / 128573); Strain CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); Strain CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); Strain CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); Strain COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986); Strain COT202 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986). 2007-067868 or WO2005 / 054479); strain COT203 (cotton, insect control, not preserved, described in WO2005 / 054480); strain DAS21606-3 / 1606 (soybean, herbicide resistant, preserved as PTA-11028, described in WO2012 / 033794); strain DAS40278 (maize, herbicide resistant, preserved as ATCC PTA-10244, described in WO2011 / 022469); strain DAS-44406-6 / pDAB8264.44.06.l (soybean, herbicide resistant, preserved as PTA-11336, described in WO2012 / 075426); strain DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide resistant, deposited as PTA-11335, described in WO2012 / 075429), strain DAS-59122-7 (maize, insect control - herbicide resistant, deposited as ATCC PTA 11384, described in US-A 2006-070139); strain DAS-59132 (maize, insect control - herbicide resistant, not deposited, described in WO2009 / 100188); strain DAS68416 (soybean, herbicide resistant, deposited as ATCC PTA 11335, described in US-A 2006 / 070139). PTA-10442 is deposited, described in WO2011 / 066384 or WO2011 / 066360; line DP-098140-6 (maize, herbicide resistant, deposited as ATCCPTA-8296, described in US-A 2009-137395 or WO 08 / 112019); line DP-305423-1 (soybean, quality traits, not deposited, described in US-A 2008-312082 or WO2008 / 054747); line DP-32138-1 (maize, hybrid system, deposited as ATCC PTA-9158).Recorded in US-A 2009-0210970 or WO2009 / 103049; strain DP-356043-5 (soybean, herbicide resistant, deposited as ATCC PTA-8287, recorded in US-A 2010-0184079 or WO2008 / 002872); strain EE-I (eggplant, insect control, not deposited, recorded in WO 07 / 091277); strain Fil17 (maize, herbicide resistant, deposited as ATCC 209031, recorded in US-A 2006-059581 or WO The following strains are listed: 98 / 044140; strain FG72 (soybean, herbicide resistant, deposited as PTA-11041, described in WO2011 / 063413); strain GA21 (maize, herbicide resistant, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); strain GG25 (maize, herbicide resistant, deposited as ATCC 209032, described in US-A 2005-188434 or WO98 / 044140); strain GHB119 (cotton, insect control - herbicide resistant, deposited as ATCC PTA-8398, described in WO2008 / 151780); strain GHB614 (cotton, herbicide resistant, deposited as ATCC PTA-8398, described in WO2008 / 151780). PTA-6878 is deposited, described in US-A 2010-050282 or WO2007 / 017186; strain GJ11 (maize, herbicide resistant, deposited as ATCC 209030, described in US-A 2005-188434 or WO98 / 044140); strain GM RZ13 (sugar beet, virus resistant, deposited as NCIMB-41601, described in WO2010 / 076212); strain H7-l (sugar beet, herbicide resistant, deposited as NCIMB41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004 / 074492); strain JOPLINl (wheat, disease resistant, not deposited, described in US-A 2008-064032); line LL27 (soybean, herbicide resistant, deposited as NCIMB 41658, described in WO2006 / 108674 or US-A 2008-320616); line LL55 (soybean, herbicide resistant, deposited as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127); line LLcotton25 (cotton, herbicide resistant, deposited as ATCC PTA-3343,Recorded in WO2003 / 013224 or US A2003-097687; line LLRICE06 (rice, herbicide tolerant, deposited as ATCC 203353, recorded in US 6,468,747 or WO2000 / 026345); line LLRICE62 (rice, herbicide tolerant, deposited as ATCC 203352, recorded in WO2000 / 026345); line LLRICE601 (rice, herbicide tolerant, deposited as ATCC PTA-2600, recorded in US-A2008-2289060 or WO2000 / 026356); line LY038 (maize, quality traits, deposited as ATCC PTA-5623, recorded in US-A The following strains are described in US-A 2007-028322 or WO2005 / 061720: strain MIR162 (maize, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007 / 142840); strain MIR604 (maize, insect control, not deposited, described in US-A 2008-167456 or WO2005 / 103301); strain MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO2002 / 100163); strain MON810 (maize, insect control, not deposited, described in US-A 2009-300784 or WO2007 / 142840). MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A 2006-095986); MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); MON87460 (maize, stress tolerance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A 2011-0138504); MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009 / 064652); line MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A2010-0080887 or WO2010 / 037016); line MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); line MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199).Strain MON87754 (soybean, quality traits, deposited as ATCC PTA-9385, described in WO2010 / 024976); Strain MON87769 (soybean, quality traits, deposited as ATCC PTA-8911, described in US-A2011-0067141 or WO2009 / 102873); Strain MON88017 (maize, insect control - herbicide resistance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005 / 059103); Strain MON88913 (cotton, herbicide resistance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); line MON88302 (rapeseed, herbicide resistant, deposited as PTA-10955, described in WO2011 / 153186), line MON88701 (cotton, herbicide resistant, deposited as PTA-11754, described in WO2012 / 134808), line MON89034 (maize, insect control, deposited as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); line MON89788 (soybean, herbicide resistant, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); line MS1 1 (rapeseed, pollination control-herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO2001 / 031042); line MS8 (rapeseed, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); line NK603 (maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); line PE-7 (rice, insect control, not deposited, described in WO2008 / 114282); line RF3 (rapeseed, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347). 2003-188347); line RT73 (rapeseed, herbicide resistant, not preserved, described in WO2002 / 036831 or US-A 2008-070260); line SYHT0H2 / SYN-000H2-5 (soybean, herbicide resistant, preserved as PTA-11226, described in WO2012 / 082548); line T227-1 (sugar beet, herbicide resistant, not preserved).Recorded in WO2002 / 44407 or US-A 2009-265817; line T25 (maize, herbicide resistant, not preserved, recorded in US-A 2001-029014 or WO2001 / 051654); line T304-40 (cotton, insect control - herbicide resistant, preserved as ATCC PTA-8171, recorded in US-A 2010-077501 or WO2008 / 122406); line T342-142 (cotton, insect control, not preserved, recorded in WO2006 / 128568); line TC1507 (maize, insect control - herbicide resistant, not preserved, recorded in US-A 2009-265817). 2005-039226 or WO2004 / 099447; line VIP1034 (maize, insect control - herbicide resistance, deposited as ATCC PTA-3925, described in WO2003 / 052073), line 32316 (maize, insect control - herbicide resistance, deposited as PTA-11507, described in WO2011 / 084632), line 4114 (maize, insect control - herbicide resistance, deposited as PTA-11506, described in WO2011 / 084621), optionally superimposed with line EE-GM1 / LL27 or line EE-GM2 / LL55 (WO2011 / 063413A2) line EE-GM3 / FG72 (soybean, herbicide resistant, ATCC registration number PTA-11041), strain DAS-68416-4 (soybean, herbicide resistant, ATCC registration number PTA-10442, WO2011 / 066360A1), strain DAS-68416-4 (soybean, herbicide resistant, ATCC registration number PTA-10442, WO2011 / 066384A1), strain DP-040416-8 (maize, insect control, ATCC registration number PTA-11508, WO2011 / 075593A1), strain DP-043A47-3 (maize, insect control, ATCC registration number PTA-11509, WO2011 / 075595A1), strain DP- 004114-3 (maize, insect control, ATCC registration number PTA-11506, WO2011 / 084621A1), strain DP-032316-8 (maize, insect control, ATCC registration number PTA-11507, WO2011 / 084632A1), strain MON-88302-9 (rapeseed, herbicide tolerance, ATCC registration number PTA-10955, WO2011 / 153186A1), strain DAS-21606-3 (soybean, herbicide tolerance, ATCC registration number PTA-11028, WO2012 / 033794A2).The following lines are included: MON-87712-4 (soybean, quality traits, ATCC registration number PTA-10296, WO2012 / 051199A2), DAS-44406-6 (soybean, superimposed herbicide tolerance, ATCC registration number PTA-11336, WO2012 / 075426A1), and DAS-14536-7 (soybean, superimposed herbicide tolerance, ATCC registration number PTA-11335, WO2012 / 075429). A1), line SYN-000H2-5 (soybean, herbicide tolerant, ATCC registration number PTA-11226, WO2012 / 082548A2), line DP-061061-7 (rapeseed, herbicide tolerant, no available accession number, WO2012071039A1), line DP-073496-4 (rapeseed, herbicide tolerant, no available accession number, US2012131692), line 8264.44.06.1 (soybean, herbicide tolerant, superimposed herbicide tolerant). Herbicide tolerance, registration number PTA-11336, WO2012075426A2), line 8291.45.36.2 (soybean), superimposed herbicide tolerance, registration number PTA-11335, WO2012075429A2, line SYHT0H2 (soybean, ATCC registration number PTA-11226, WO2012 / 082548A2), line MON88701 (cotton, ATCC registration number PTA-11754, WO20 12 / 134808A1), line KK179-2 (alfalfa, ATCC registration number PTA-11833, WO2013 / 003558A1), line pDAB8264.42.32.1 (soybean, superimposed herbicide tolerance, ATCC registration number PTA-11993, WO2013 / 010094A1), line MZDT09Y (maize, ATCC registration number PTA-13025, WO2013 / 012775A1).

[0254] In addition, the USDA's Animal and Plant Health Inspection Service (APHIS) provides a list of such transgenic strains, which can be found on their website on the internet. aphis.usda.gov Found online. For the purposes of this application, the status of this list as of the date of filing this application is relevant.

[0255] Genes / lines conferring the desired traits discussed can also exist in combination in transgenic plants. Examples of transgenic plants that can be mentioned include important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and fruit plants (fruits such as apples, pears, citrus fruits, and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed. The traits particularly emphasized are enhanced plant resistance to insects, arachnids, nematodes, slugs, and snails, as well as enhanced plant resistance to one or more herbicides.

[0256] Commercially available examples of plants, plant parts, or plant seeds that can be preferably treated according to the present invention include GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLEPRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, and ROUNDUP READY® 2 XTEN. DTM Commercially available products sold or distributed under the trade names INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEX™, such as plant seeds.

[0257] Pathogens Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include: A disease caused by a powdery mildew pathogen, such as *Erysiphe bryophyte* (… Blumeria ) genus and species, such as *Brucea purpurea* (a member of the Poaceae family) Blumeria graminis ); genus *Cyclocarya* ( Podosphaera ) genus and species, such as *Synthetium lappa* (… Podosphaera leucotricha ); genus *Monophyllum* ( Sphaerotheca ) genus and species, such as Erythrinae monotypica ( Sphaerotheca fuliginea ); genus *Hylocereus* ( Uncinula ) genus and species, such as grape clematis ( Uncinula necator ); Diseases caused by rust pathogens, such as *Cladophora* spp. (… Gymnosporangium ) genus and species, such as brown rust fungus ( Gymnosporangium sabinae ); genus *Camelus* ( Hemileia ) genus and species, such as *Camelus coffeeensis* ( Hemileia vastatrix ); genus Laminaria ( Phakopsora ) genus and species, such as *Pseudomonas beanus* rust ( Phakopsorapachyrhizi ) or rust fungus of the mountain locust layer ( Phakopsora meibomiae ); genus *Stiperus* ( Puccinia ) genus and species, such as *Cryptomeria cryptica* ( Puccinia recondita ), wheat stalk rust fungus ( Puccinia graminis ) or wheat stripe rust ( Puccinia striiformis ); genus *Russula* ( Uromyces ) genus and species, such as *Atopomonas rust* ( Uromyces appendiculatus ); Diseases caused by pathogens selected from the class Oomycetes, such as white rust fungi (… Albugo ) genus and species, such as white rust fungi ( Albugo candida ); *Panthera* ( Bremia ) genus and species, such as *Peronospora fuscipes* ( Bremia lactucae ); genus *Peronospora* ( Peronospora ) genus and species, such as pea downy mildew ( Peronospora pisi ) or cruciferous downy mildew ( P. brassicae Phytophthora ( ); Phytophthora ( Phytophthora ) genus and species, such as Phytophthora pathogenica ( Phytophthora infestans ); genus *Peronospora* ( Plasmopara ) genus and species, such as *Peronospora vitis* ( Plasmopara viticola ); genus *Pseudomonas* ( Pseudoperonospora ) genus and species, such as *Pseudomonas aeruginosa* ( Pseudoperonospora humuli ) or Cuban pseudo downy mildew ( Pseudoperonospora cubensis ); Pythium ( Pythium ) genus and species, such as Pythium truncatum ( Pythium ultimum ); Leaf spot and leaf wilt diseases caused by the following pathogens: for example, Alternaria species ( Alternaria ) genus and species, such as Alternaria solani ( Alternaria solani ); Cercospora ( Cercospora ) genus and species, such as *Cercospora spp.* Cercospora beticola ); Cladosporium ( Cladiosporum ) genus species, such as Cucumber Cladosporium ( Cladiosporum cucumerinum ); *Cyclophorus* genus ( Cochliobolus ) genus and species, such as Cyclospora gracilis ( Snail agricultural (Conidia form: genus *Enteromorpha*) Drechslera Synonyms: genus *Heliconia* Helminthosporium )) or Cyclospora uteri ( Cochliobolus miyabeanus Anthrax genus ( Colletotrichum ) genus and species, such as *Anthracis beanus* ( Colletotrichum lindemuthanium ); genus *Cynoglossum* ( Corynespora ) genus species, such as *Cyclocarya paliurus* ( Corynespora cassicola); Rust spot fungus ( Cyclone ) genus and species, such as *Olive peacock spot fungus* ( Cycloconium oleaginum ); genus *Ceratophyllum* ( Diaporthe ) genus and species, such as citrus interset shell ( Citrus diaportha ); *Cryptocele* ( Elsinore ) genus species, such as Citrus scabies ( Elsinoe fawcettii ); genus *Palmaria* ( Gloeosporium ) genus and species, such as *Cymbidium goeringii* ( Gloeosporium laeticolor ); *Smallaria* ( Glomerulus ) genus and species, such as *Cyclocarya paliurus* ( Glomerulus girdle ); genus *Sphaerophytes* ( Guignard ) genus and species, such as Staphylococcus ( Guignardia bidwellii ); Micrococcus spp. ( Leptosphaeria ) genus and species, such as Micrococcus tarsi ( Leptosphaeria maculans ); genus *Megaminorococcus* ( Magnaporth ) Genus and species, such as the grey great shell ( Magnaporthe grisea ); Micrococcus ( Microdochium ) genus and species, such as *Microsorum psyllium* ( Snowdrop ); genus Cocci ( Mycosphaerella ) genus and species, such as Gramineae ( Mycosphaerella graminicola ), Arachis coccus ( Mycosphaerella arachidicola ) and Fiji coccidioidomyces ( Mycosphaerella fijiensis ); genus *Syngonium* ( Phaeosphere ) genus and species, such as *Syngonium gleditsiae* ( Phaeosphere nodules ); genus *Nucleobacillus* ( Pyrenophora ) genus and species, such as *Rhizoctonia solani* ( Pyrenophora teres ), Sclerotium truncatum ( Wheat spikelet ); *Pseudomonas* ( Ramularia ) genus and species, such as *Syngae styracifolium* ( Swan-necked ramularia ) or white spot columnar septum ( Ramularia areola ); genus *Rhizophora* ( Rhynchosporium ) genus and species, such as Ryebeak ( Rhynchosporium secalis ); genus *Syngonium* ( Septoria ) genus and species, such as *Syngonium celeryensis* ( Septoria celery ) or tomato shell spores ( Septoria tomato ); Stagonospora Genus and species, for example Stagonospora nodorum ; genus *Russula* ( Typhula ) genus and species, such as Sarcodactylus ( Typhula incarnata ); Black Star Fungus ( Ventura ) genus and species, such as *Aureobasidium clavatum*, the pathogen causing apple scab. Unequal Venturia ); Root and stem diseases caused by pathogens such as *Fructus fusca* (e.g., *Fructus fusca*). Bark) genus and species, such as *Gnaphalium gracilis* ( Grass bark Fusarium ( ); Fusarium genus ( Fusarium ) genus and species, such as Fusarium oxysporum ( Fusarium oxysporum ); genus *Tetranychus* ( Gaeumannomyces ) genus and species, such as *Potamogeton crispus* (grass pods) Gaeumannomyces graminis ); Plasmodium genus ( Plasmodium phylum ) genus and species, such as *Plasmodiophora brassicae* ( Brassica spp. ); Rhizoctonia spp. ( Rhizoctonia ) genus and species, such as Rhizoctonia solani ( Rhizoctonia solani ); genus *Broomella* ( Sarocladium ) genus and species, such as *Bryophytum oryzae* ( Sarocladium oryzae ), Sclerotium genus ( Sclerotium ) genus and species, such as *Sclerotium oryzae* ( Sclerotium of rice ), Tapestry Genus and species, for example Tapesia acuminate ; Rhizophora genus ( Thielaviopsis ) genus and species, such as Rhizoctonia ( Thielaviopsis basicola ); Diseases of the spadix and panicle (including maize cob) caused by the following pathogens: for example, Alternaria ( Alternaria ) genera and species, such as Alternaria ( Alternaria spp. ); Aspergillus ( Aspergillus ) genera and species, such as Aspergillus flavus; Cladosporium ( Cladosporium ) genus and species, such as Cladosporium cladosporum ( Cladosporium cladosporioides ); ergot ( Harpsichord ) genus and species, such as ergot ( Claviceps purpurea Fusarium ( ); Fusarium genus ( Fusarium ) genus and species, such as Fusarium oxysporum ( Fusarium wilt ); Gibberellins ( Gibberella ) genus and species, such as Fusarium graminearum ( Gibberella zeae ); Small-lined shell genus ( Monograph ) genus and species, such as *Symplocos nigra* ( Monographella nivalis ); Stagonospora Genus and species, for example Stagonospora nodorum ; Diseases caused by smut fungi, such as *Ustilago maydis* (a genus of fungi). Sphacelotheca ) genus and species, such as *Ustilago maydis* ( Sphacelotheca reiliana ); *Solanum lycopersicum* ( Tilletia ) genus and species, such as wheat smut ( Tilletia caries ) or wheat dwarf smut ( Controversial Tilletia ); smut fungi ( ) Urocyst ) genus and species, such as *Ustilago maydis* ( Urocystis occulta ); Ustilago maydis genus ( I burn. ) genus and species, such as *Ustilago maydis* ( Naked scald ); Fruit rot caused by the following pathogens: for example, species of the genus Aspergillus, such as Aspergillus flavus; Botrytis cinerea (… Botrytis ) genus and species, such as Botrytis cinerea ( Botrytis cinerea ); genus *Streptococcus* ( Monilinia ) genus and species, such as *Streptococcus sclerotiorum* ( Loose monilinia Penicillium ( ) Penicillium ) genus and species, such as Penicillium extensionum ( Penicillium expanse ) or produce Penicillium purpureum ( Penicillium purpurogenus Rhizopus ( ); Rhizopus ( Rhizopus ) genus and species, such as *Rhizopus* ( Rhizopus stolonifer ); Sclerotium genus ( Sclerotinia ) genus and species, such as Sclerotinia sclerotiorum ( Sclerotinia sclerotia ); Verticillium ( Whorl ) genus and species, such as Verticillium purpureus ( Whorl white-collar worker ); Seed-borne rot and soil-borne rot and wilting diseases, as well as seedling diseases, are caused by the following pathogens: for example, Alternaria species ( Alternaria ) genus and species, such as Alternaria brassicae ( Alternaria brassicicola ); genus *Hymenopterus* ( Aphanomyces ) genus and species, such as Rhizopus and Hymenops ( Aphanomyces euteiches ); genus Dicellae ( Ascochyta ) genus and species, such as lentil spores ( Ascochyta lentil ); genus and species of Aspergillus, such as Aspergillus flavus; genus Cladosporium ( Cladosporium ) genus and species, such as Cladosporium herbaceum ( Cladosporium herbarium ); *Cyclophorus* genus ( Snail ) genus and species, such as Cyclospora gracilis ( Cochliobolus sativus (Conidia form: genus *Enteromorpha*) Drechslera ), genus *Isomonium* Bipolar Synonyms: genus *Heliconia* Helminthosporium Anthrax ( )); Anthrax genus ( Colletotrichum ) genus and species, such as *Anthrax pilosa* ( Colletotrichum coccodes Fusarium ( ); Fusarium genus ( Fusarium ) genus and species, such as Fusarium oxysporum ( Fusarium wilt ); Gibberellins ( Gibberella ) genus and species, such as Fusarium graminearum ( Gibberella zeae ); genus *Cyclophorus* ( Macrophomina ) genus and species, such as *Cyclocarya spp.* Macrophomina bean sprout ); Micrococcus ( Microdochium ) genus and species, such as *Microsorum psyllium* ( Snowdrop ); Small-lined shell genus ( Monograph ) genus and species, such as *Symplocos nigra* ( Monographella nivalis Penicillium ( ) Penicillium ) genus and species, such as Penicillium extensionum ( Penicillium expansum ); Phytophthora spp. ( Food ) genus and species, such as black shank stem spot ( Phoma lingam ); *Pseudostemia* ( Phomopsis ) genus and species, such as *Pseudomonas sacchariformis* (soybean Phomopsis soybeans Phytophthora ( ); Phytophthora ( Phytophthora ) genus and species, such as Phytophthora ( Phytophthora cactorum ); genus *Nucleobacillus* ( Pyrenophora ) genus and species, such as *Rhizoctonia solani* ( Pyrenophora grass ); Pyreospora ( Firefly ) genus and species, such as *Pyrhododendron* ( Rice blast ); Pythium ( Pythium ) Genus and species, such as Pythium truncatum ( Pythium last ); Rhizoctonia spp. ( Rhizoctonia ) genus and species, such as Rhizoctonia solani ( Rhizoctonia solani Rhizopus ( ); Rhizopus ( Rhizopus ) genus and species, such as Rhizopus oryzae ( Rhizopus rice ); Sclerotium genus ( Sclerotium ) genus and species, such as *Sclerotium sclerotiorum* ( Sclerotium rolfsii ); genus *Syngonium* ( Septoria ) genus and species, such as *Syngonium gleditsiae* ( Septoria knots ); genus *Russula* ( Typhula ) genus and species, such as Sarcodactylus ( Typhula incarnata Verticillium ( Verticillium wilt ) genus species, such as Verticillium dahliae ( Verticillium dahliae ); Cancerous diseases, galls, and broom diseases caused by the following pathogens: for example, those of the genus *Ceratophyllum* (… Nectarine ) genus and species, such as *Rhizopus macranthum* (a type of pomegranate). Nectria galligena ); Wilting diseases caused by pathogens such as Verticillium (e.g., Verticillium spp.) Verticillium wilt ) Genus and species, for example Verticillium wilt long-spored Fusarium ( ) Fusarium ) genus and species, such as Fusarium oxysporum ( Fusarium oxysporum ); Deformities of leaves, flowers, and fruits caused by pathogens such as *Exobasidiomycetes* (e.g., *Exobasidiomycetes*). Exobasidium ) genus and species, such as exobasidiomycetes ( Exobasidium vexans ); Exocystis ( Taphrina ) genus and species, such as *Exocystis aeruginosa* ( Taphrina deformans ); Degenerative diseases of woody plants caused by the following pathogens: for example, according to family and genus ( Food ) genus and species, such as Rhizopus glabripennis ( Phaemoniella chlamydospora ), Chicken leg mushroom filamentosa ( Phaeoacremonium aleophilum ) or Mediterranean porphyria ( Mediterranean Fomitiporia ); Ganoderma ( Ganoderma ) genus and species, such as Ganoderma angustifolia ( Ganoderma boninense ); Diseases of plant tubers caused by pathogens such as Rhizoctonia solani (e.g., Rhizoctonia solani). Rhizoctonia ) genus and species, such as Rhizoctonia solani ( Rhizoctonia solani ); genus Hemlock ( Helminthosporium ) genus and species, such as *Lysimachia foetida* (soybean worm). Helminthosporium solani ); Diseases caused by the following bacterial pathogens, such as Xanthomonas ( Xanthomonas ) genus and species, such as Xanthomonas oryzae var. bleachingii ( Xanthomonas campestris pv. rice ); Pseudomonas spp. ( Pseudomonas ) genus and species, such as *Pseudomonas syringae* var. *cucumber* (… Pseudomonas syringae pv. lachrymans Erwinia spp. Erwinia ) genus and species, such as Erwinia amygdalina ( Erwinia amylovora ); Bacillus phloemus ( Liberibacter ) Genus and species, for example Liberibacter asiaticus ; genus *Xylomycin* ( Xyella ) genus and species, such as *Streptomyces* ( Xylella fastidiosa Ralstonia solanacearum ( ); Ralstonia solanacearum genus ( Ralstonia ) genus and species, such as Ralstonia solanacearum ( Ralstonia solanacearum ); Dickey Genus and species, for example Dickeya solani Corynebacterium spp. Clavibacter ) Genus and species, for example Clavibacter michiganensis Streptomyces ( Streptomyces ) genus and species, such as Streptomyces scabies ( Streptomyces scabies ).

[0258] Soybean diseases: Fungal diseases affecting leaves, stems, pods, and seeds caused by pathogens such as Alternaria leaf spot (e.g., Alternaria leaf spot). Alternaria leaf spot Alternaria spec.atrans tenuissima ),anthrax( Anthracnose () Colletotrichum gloeosporoides dematium var.truncatum Brown spot disease (soybean scab) Septoria glycines Cercospora leaf spot and leaf blight ( Cercospora leaf spot andblight) (Cercospora Kikuchi ( Cercospora kikuchii Leaf blight of the genus *Ceratophyllum* ( ) Choanephora leaf blight) Choanephora infundibulifera trispora (Synonyms) Dactuliophora Leaf spot disease (Dactuliophora glycines Downy mildew (Northeast downy mildew) Peronospora manshurica ), Wiltia spp. ( )), Wiltia spp. ( ) Drechslera blight Drechslera glycini Soybean gray spot disease frogeye leaf spot) (Cercospora soybean ( Cercospora sojina Leaf spot disease of the genus *Scleroderma* ( ) Leptosphaerulina leaf spot (clover husk) Leptosphaerulina trifolii Leaf spot disease of the genus *Lepidium* ( ) Phyllostica leaf spot (soybean leaf spot mold) Phyllosticta sojaecola ), pod and stem wilt (soybean wilt disease ( ) ... Phomopsis sojae )),powdery mildew( Microsphaera diffusa ), Echinococcus leaf spot ( Pyrenochaeta leaf spot (Soybean red leaf spot pathogen) Pyrenochaeta glycines ), aerial rhizoctonia, leaf blight and damping-off (rhizoctonia aerial), leaf blight and damping-off (rhizoctonia solani) Rhizoctonia solani ), rust disease (bean rust fungus ( Phakopsora pachyrhizi ), Mountain locust rust fungus ( Phakopsora meibomiae ), scab (soybean scab scab (soybean scab scab) Sphaceloma glycines Leaf blight of the genus *Cyperus* ( ) stemphylium leaf blight)( creeping mold)( Stemphylium botryosum Sudden death syndrome () Fusarium virguliforme ), target spot disease (Bacillus subtilis) Corynespora cassiicola )).

[0259] Fungal diseases of the roots and stems caused by the following pathogens: for example, black root rot (*Cyclocarya paliurus*). Calonectria crotalariae ), anthracnose (common bean scab ( )), and anthracnose (common bean Macrophomina phaseolina Fusarium wilt or wilting, root rot, and pod and root collar rot (Fusarium oxysporum) Fusarium oxysporum ), Fusarium orthorhamnosum ( Fusarium orthoceras ), Fusarium semi-nakedense ( Fusarium semitectum ), Horsetail ( Fusarium equiseti ), mycoleptodiscus root rot ( Mycoleptodiscus terrestris Neocosmospora (invasion of Neocosmospora) Neocosmopspora vasinfecta )), pod and stem wilt (intercalation of bean pods ( Diaporthe phaseolorum), stem canker (soybean stem canker pathogen ( )), stem canker (soybean northern stem canker pathogen ( Diaporthe phaseolorum var. caulivora Phytophthora rot (Phytophthora indicum ( )), Phytophthora rot ( Phytophthora indicum ( )), Phytophthora rot ( ) Phytophthora megasperma Soybean stem brown rot (soybean stem brown rot fungus ( )), stem brown rot (soybean stem brown rot fungus ( )) Phialophora gregata ), Pythium rot (Pythium rot in melons and fruits) Pythium aphanidermatum ), Pythium terrestris ( Pythium irregulare ), Pythium spp. ( Pythium debaryanum ), Phytophthora ( Pythium myriotylum ), ultimate phytosis ( Pythium ultimum Rhizoctonia solani root rot, stem rot and damping-off (Rhizoctonia solani (Rhizoctonia solani) Rhizoctonia solani ), Sclerotinia stem rot (Sclerotinia ( Sclerotinia sclerotiorum ), Sclerotinia southernblight disease ( Sclerotinia rolfsii ), root rot caused by *Thielaviopsis* (root rot) Thielaviopsis basicola )).

[0260] Mycotoxin Furthermore, the compounds and compositions of formula (I) of the present invention can reduce the content of mycotoxins in harvested materials and the food and feed made therefrom. Specifically, fungal toxins include, but are not limited to, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2-toxin and HT2-toxin, fumonisin, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids, and aflatoxin, said toxins can be produced by, for example, fungi of the genus *Fusarium* (…). Fusarium ) genus and species, such as Fusarium argentis ( F. acuminatum ), Fusarium tumefaciens ( F. asiaticum ), Oat Fusarium ( F. avenaceum Fusarium graminearum ( ), Fusarium graminearum ( F. crookwellensis ), Fusarium oxysporum ( F. culms Fusarium graminearum ( ), F. graminearum (Germaceae) Gibberella zeae ), Horsetail ( F. equisetum ), F. fujikoroi Fusarium moniliforme ( F. of the muses Fusarium oxysporum ( F. oxysporum ), Regenerating Fusarium ( F. proliferatum Fusarium pyrifolium ( ) F. poa ), F. pseudograminearum Elderberry Fusarium ( F. elderberry Fusarium truncatum ( ), F. sedge ), Fusarium seminatus ( F. semi-roofed Fusarium solani ( ) F. solani Fusarium pseudobranchii ( F. sporotrichoid ), F. langsethiae Fusarium colloides ( F. subglutinans Fusarium trifidum ( F. three-piece suit Fusarium moniliforme () F. verticillioides ) etc.; and species of the genus Aspergillus, such as Aspergillus flavus ( A. yellow Aspergillus parasiticus () A. parasiticus Aspergillus rubrum (), A. nomius ), Ochratoxin ( A. ochraceus Aspergillus lanceolata ( ) A. clavatus Aspergillus terreus ( ) A. terrestrial ), Aspergillus variegata ( A. versicolor Penicillium ( ) Penicillium ) genus and species, such as Penicillium verruciformis ( P. verrucosum ), Penicillium greenis ( P. viridicatum ), Penicillium citrinum ( P. citrinum ), extended Penicillium ( P. expansum ), Penicillium cladomorphum ( P. claviforme ), Penicillium loudi ( P. Roquefort ); ergot ( Harpsichord ) genus and species, such as *Ergotae* ( C. purpurea ), Clavicipitolus C. fusiform ), Ergot paspalum ( C. paspali ), C. africana ; *Vitis* genus ( Stachybotrys ) Genus, species and others.

[0261] material protection The compounds and compositions of formula (I) of the present invention can also be used in material protection, especially for protecting industrial materials from attack and damage by plant pathogenic fungi.

[0262] Furthermore, the compounds and compositions of formula (I) of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

[0263] In this article, industrial material This should be understood as referring to inanimate materials prepared for industrial applications. For example, industrial materials that can be protected from microbial alteration or destruction include adhesives, glues, paper, wallpaper and cardboard / boardboard, textiles, carpets, leather, wood, fibers and yarns, paints and plastic products, cooling lubricants, and other materials that can be infected or destroyed by microorganisms. Components of production equipment and buildings that can be damaged by microbial proliferation (e.g., cooling water circuits, cooling and heating systems, and ventilation and air conditioning units) are also included within the scope of the materials to be protected. Within the scope of this invention, industrial materials preferably include adhesives, glues, paper and cards, leather, wood, paints, cooling lubricants, and heat transfer fluids, more preferably wood.

[0264] The compounds and compositions of formula (I) of the present invention can prevent a variety of adverse effects, such as rotting, decay, discoloration, fading or mold.

[0265] In the case of treating wood, the compounds and compositions of formula (I) of the present invention can also be used to resist fungal diseases that are prone to grow on or inside the wood.

[0266] wood This refers to all types of timber species and all types of processed products made from that timber, such as solid wood, high-density timber, laminated wood, and plywood. Additionally, the compounds and compositions of formula (I) of this invention can be used to protect objects that may come into contact with saltwater or brackish water from contamination, particularly ship hulls, screens, nets, structures, mooring equipment, and signaling systems.

[0267] The compounds and compositions of formula (I) of the present invention can also be used to protect stored substances. Stored substances should be understood to mean natural substances or their processed products of plant or animal origin that are of natural origin and require long-term protection. Plant-derived stored substances, such as plants or plant parts (e.g., stems, leaves, tubers, seeds, fruits, grains), can be protected immediately after harvesting or after processing by (pre)drying, moistening, crushing, grinding, pressing, or baking. Stored substances also include wood, including unprocessed wood (e.g., construction timber, utility poles, and fences) or wood in finished form (e.g., furniture). Animal-derived stored substances include, for example, hides, leather, fur, and hair. The compounds and compositions of formula (I) of the present invention can prevent a variety of adverse effects, such as rot, decay, discoloration, fading, or mold.

[0268] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. The compounds and compositions of formula (I) of the present invention preferably act on fungi, especially molds, and ascomycetes that discolor and damage wood. Ascomycete Basidiomycetes ( Basidiomycetes ), Deuteromycetes ( Deuteromycetes ) and zygosacchari ( Zygomycete And it acts on mucus organisms and algae. Examples include microorganisms of the following genera: Alternaria ( Alternaria ), for example, Alternaria spp. ( Alternaria tenuis ); Aspergillus ( Aspergillus ), for example, Aspergillus niger ( Aspergillus niger ); genus Chaetomium ( Chaetonium ), for example, Chaetomium globosum ( Chaetomium globosum ); genus *Pteris* ( Coniophora ), for example, *Pteris vittata* ( Coniophora girl ); Lentinus genus ( Lentinus ), such as tiger skin mushroom ( Tiger lentil Penicillium ( ) Penicillium ), for example, Penicillium grayi ( Penicillium glaucum Polyporaceae ( ) Polyporus ), such as discoloration polypores ( Polyporus versicolor ); Aureobasidium spp. ( Aureobasidium ), for example, budding short-stemmed mold ( Aureobasidium sprouting ); genus *Symplocos* ( Sclerophoma ),For example Sclerophoma pityophila Trichoderma ( ) Trichoderma ), for example, *Trichoderma viride*; *Trichoderma* genus ( Ophiostoma spp. ), Long-beaked Shell ( Ceratocystis spp. ), genus *Pythium* Humicola spp. ), Peter's shell ( Petriella spp. ), genus *Trichoderma* ( Trichurus spp. ), genus *Gynostemma* Coriolus spp. ), genus *Plasmodium* Gloeophyllum spp. ), Pleurotus ( Pleurotus spp. ), genus *Polyporus* Poria spp. ), genus *Dryomyces* Serpula spp. ) and Casei genus ( Tyromyces spp. ), Cladosporium ( Cladosporium spp. ), Penicillium genus ( Paecilomyces spp. Mucor ( ) Mucor spp. ), Escherichia coli ( Escherichia ), such as E. coli ( Escherichia coli ); Pseudomonas spp. ( Pseudomonas ), such as Pseudomonas aeruginosa ( Pseudomonas aeruginosa Staphylococcus spp. Staphylococcus), such as Staphylococcus aureus ( Staphylococcus aureus ), Candida ( Candida spp. ) and yeast ( Saccharomyces spp. ), such as brewer's yeast ( Saccharomyces cerevisae ).

[0269] Seed treatment The compounds and compositions of formula (I) of the present invention can be used to protect seeds from unwanted microorganisms, such as plant pathogenic microorganisms, like plant pathogenic fungi or plant pathogenic oomycetes. The terminology used herein... seed This includes dormant seeds, primed seeds, pre-germinated seeds, and seeds that have already developed roots and leaves.

[0270] Therefore, the present invention also relates to a method for protecting seeds from unwanted microbial infection, which includes the step of treating the seeds with a compound or composition of formula (I) of the present invention.

[0271] Treating seeds with compounds or compositions of formula (I) of the present invention protects seeds from infection by plant pathogenic microorganisms, and can also protect germinating seeds, newly emerging seedlings, and plants that have emerged from treated seeds. Therefore, the present invention also relates to a method for protecting seeds, germinating seeds, and newly emerging seedlings.

[0272] Seed treatment can be performed before sowing, at sowing, or shortly after sowing.

[0273] When seed treatment is performed before sowing (e.g., so-called application to the seeds), the seed treatment can be carried out by the following steps: the seeds can be placed in a mixer containing the desired amount of the compound or composition of formula (I) of the present invention, and the seeds and the compound or composition of formula (I) of the present invention can be mixed until a uniform distribution is achieved on the seeds. If appropriate, the seeds can be dried.

[0274] The present invention also relates to seeds coated with a compound or composition of formula (I) of the present invention.

[0275] Preferably, the seeds are treated in a state where they are sufficiently stable to prevent damage during treatment. Generally, seeds can be treated at any time between harvesting and immediately after sowing. Seeds that have been separated from the plant and from which the core, shell, stem, bark, hairs, or pulp have been removed are typically used. For example, seeds that have been harvested, cleaned, and dried to a moisture content of less than 15% by weight can be used. Alternatively, seeds that have been dried, for example, treated with water and then dried again, or seeds that have only been pre-germinated, or seeds stored or pre-germinated under pre-germination conditions, or seeds planted in nursery trays, strips, or paper can also be used.

[0276] The amount of the compound or composition of formula (I) of the present invention applied to seeds is generally such that it does not impair seed germination or the mature plant. This must be ensured, especially for compounds of formula (I) that may exhibit phytotoxicity at certain application rates. The inherent phenotype of the transgenic plant should also be considered when determining the amount of the compound of formula (I) applied to the seeds, so as to achieve optimal protection of the seeds and germinating plants using the minimum amount of the compound used.

[0277] The compound of formula (I) can be applied directly to the seeds on its own, without the use of any other components and without dilution. The compositions of the present invention can also be applied to the seeds.

[0278] The compounds and compositions of formula (I) of the present invention are suitable for protecting the seeds of any plant variety. Preferred seeds include cereals (such as wheat, barley, rye, millet, triticale, and oats), rapeseed, corn, cotton, soybean, rice, potato, sunflower, kidney bean, coffee, pea, beet (e.g., sugar beet and forage beet), peanut, vegetables (such as tomato, cucumber, onion, and lettuce), turfgrass, and ornamental plant seeds. More preferred are the seeds of wheat, soybean, rapeseed, corn, and rice.

[0279] The compounds and compositions of formula (I) of the present invention can be used to treat transgenic seeds, particularly plant seeds capable of expressing polypeptides or proteins that act against pests, herbicide damage, or abiotic stresses, thereby increasing protection. Plant seeds capable of expressing polypeptides or proteins that act against pests, herbicide damage, or abiotic stresses may contain at least one heterologous gene that allows the expression of said polypeptide or protein. These heterologous genes in the transgenic seeds may be derived from microorganisms such as *Bacillus*, *Rhizobium*, *Pseudomonas*, *Serratia*, *Trichoderma*, *Clavibacter*, *Glomus*, or *Gliocladium*. Preferably, the heterologous gene is derived from a *Bacillus* species, wherein the gene product is effective against the European corn borer and / or the Western corn rootworm. Particularly preferred is that the heterologous gene is derived from Bacillus thuringiensis.

[0280] application The compound of formula (I) may be applied on its own or in the form of, for example, ready-to-use solutions, emulsions, water-based or oil-based suspensions, powders, wettable powders, pastes, soluble powders, powders, soluble granules, broadcast granules, suspension concentrates, natural products impregnated with the compound of formula (I), synthetic substances impregnated with the compound of formula (I), fertilizers, or polymers in the form of microcapsules.

[0281] Application can be made by conventional methods, such as watering, spraying, atomizing, broadcasting, dusting, foaming, or spreading. Compounds of formula (I) can also be applied via ultra-low volume methods, using drip irrigation systems or soaking, by applying them in furrows or injecting them into the stems or trunks of the soil. Compounds of formula (I) can also be applied by wound sealing, coating, or other wound dressings.

[0282] The effective and plant-compatible amount of a compound of formula (I) applied to plants, plant parts, fruits, seeds or soil will depend on a variety of factors, such as the compound / composition used, the object of treatment (plant, plant part, fruit, seed or soil), the type of treatment (powdering, spraying, seed dressing), the purpose of treatment (therapeutic and protective), the type of microorganism, the developmental stage of the microorganism, the sensitivity of the microorganism, the growth stage of the crop and environmental conditions.

[0283] When using compounds of formula (I) as fungicides, the application rate can vary over a wide range depending on the type of application. When treating plant parts such as leaves, the application rate can be 0.1 to 10,000 g / ha, preferably 10 to 1,000 g / ha, more preferably 50 to 300 g / ha (the application rate can be even lower when applied by irrigation or drip irrigation, especially when using inert materials such as rock wool or perlite). When treating seeds, the application rate can be 0.1 to 200 g per 100 kg of seeds, preferably 1 to 150 g per 100 kg of seeds, more preferably 2.5 to 25 g per 100 kg of seeds, and even more preferably 2.5 to 12.5 g per 100 kg of seeds. When treating soil, the application rate can be 0.1 to 10,000 g / ha, preferably 1 to 5,000 g / ha.

[0284] These application rates are merely examples and are not intended to limit the scope of the invention.

[0285] The compounds and compositions of formula (I) of the present invention can be used in combination with models, for example, embedded in computer programs, for site-specific crop management, satellite agriculture, precision farming, or precision agriculture. These models utilize data from various sources (e.g., soil, weather, crops (e.g., variety, growth stage, plant health), weeds (e.g., variety, growth stage), diseases, pests, nutrients, water, humidity, biomass, satellite data, yield, etc.) to support site-specific management of agricultural sites with the aim of optimizing environmental profitability, sustainability, and protection. In particular, such models can help optimize agronomic decisions, control the precision of pesticide application, and record the work done.

[0286] For example, if the model models the development of fungal diseases and calculates that the threshold for applying the compound of formula (I) to crop plants has been reached, the compound of formula (I) can be applied to crop plants according to an appropriate dosage regimen.

[0287] Commercially available systems that include agronomic models include, for example, FieldScripts from The Climate Corporation. TM Xarvio from BASF TM AGLogic from John Deere TM wait.

[0288] The compounds of formula (I) can also be used in combination with smart spraying devices, such as spot spraying or precision spraying devices attached to or housed within agricultural vehicles (such as tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs) such as drones, etc.). Such devices typically include input sensors (e.g., cameras) and a processing unit configured to analyze input data and to provide decisions based on the analysis of the input data, applying the compounds of the invention to crop plants (weeds, respectively) in a specific and precise manner. The use of such smart spraying devices typically also requires a positioning system (e.g., a GPS receiver) to locate recorded data and guide or control the agricultural vehicle; a geographic information system (GIS) to represent information on an understandable map; and appropriate agricultural vehicles to perform the required agricultural actions, such as spraying.

[0289] In one instance, fungal diseases can be detected from images acquired by a camera. In another instance, fungal diseases can be identified and / or classified based on this image. This identification and / or classification can utilize image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neural networks, decision trees, and artificial intelligence algorithms. In this way, the compounds described herein can be applied only when needed.

[0290] The aspects of the teachings of this invention can be further understood from the following examples, which should not be construed as limiting the scope of the invention in any way.

[0291] A. Example A-1. Overview A-1.1. Determination of LogP value According to EEC directive 79 / 831 Annex V.A8, the LogP values ​​presented herein were measured by HPLC (high performance liquid chromatography) on a reversed-phase column using the following method: [a] LogP values ​​were determined by LC-UV measurement in an acidic range using 0.1% formic acid aqueous solution and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0292] [b] LogP values ​​were determined by LC-UV measurement within a neutral range using 0.001 mol of aqueous ammonium acetate and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0293] [c] LogP values ​​were determined by LC-UV measurement in an acidic range using 0.1% phosphoric acid and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0294] If more than one LogP value can be obtained within the same method, all values ​​are shown and separated by "+".

[0295] Calibration was performed using straight-chain alkyl-2-ones (with 3 to 16 carbon atoms) with known LogP values ​​(LogP values ​​were measured using retention times via linear interpolation between consecutive alkyl-2-ones). λ was determined using peak values ​​of UV spectra and chromatographic signals from 200 nm to 400 nm. max value.

[0296] A-1.2. 1 H-NMR data The selected embodiments provided herein 1 H-NMR data with 1 The H-NMR peaks are presented in a list format. For each signal peak, the δ value in ppm is listed, and the signal intensity is listed in parentheses. Semicolons are used as separators between the δ value and signal intensity pairs.

[0297] Therefore, the peak list for an instance takes the following form: δ1 (Intensity 1); δ2 (Intensity 2); ...; δi (strength i );........;δ n (strength n ) The intensity of a sharp signal is highly correlated with the signal of the printed example of the NMR spectrum in cm⁻¹, and shows the true relationship of signal intensity. A broad signal can show multiple peaks or the signal median and its relative intensity compared to the strongest signal in the spectrum.

[0298] For calibration 1 For the chemical shifts in the 1H NMR spectrum, we utilize the chemical shifts of tetramethylsilane and / or the solvent used, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may, but is not required, appear in the NMR peak list.

[0299] 1 The list of H-NMR peaks is similar to that of conventional ones. 1 H-NMR prints, therefore, typically contain all the peaks listed in conventional NMR analysis.

[0300] In addition, as usual 1 H-NMR printouts can display solvent signals, signals of stereoisomers of the target compound (which are also the subject of this invention), and / or signals of impurity peaks.

[0301] To illustrate the compound signal in the δ range of solvents and / or water, conventional peaks for solvents, such as the peak for DMSO in DMSO-D6, and peaks for water, are shown in our diagram. 1 It appears in the H-NMR peak list and typically has a high average intensity.

[0302] The peaks of the stereoisomers of the target compound and / or the peaks of impurities typically have lower average intensities than the peaks of the target compound (e.g., with >90% purity).

[0303] These stereoisomers and / or impurities can be typical for a particular preparation method. Therefore, their peaks can help identify the reproducibility of the preparation method using "side-product fingerprints".

[0304] Experts who calculate the target compound peaks using known methods (MestreC, ACD simulation, and expected values ​​obtained through empirical evaluation) can optionally use additional intensity filters to separate the target compound peaks as needed. This separation is similar to conventional methods. 1 Picking of relevant peaks under H-NMR analysis.

[0305] Further details regarding the description of NMR data with peak lists can be found in the publication "Citation of NMR Peaklist Data within Patent Applications" in Research Disclosure Database No. 564025.

[0306] The following examples illustrate the preparation and bioactivity of compounds of formula (I) according to the present invention in a non-limiting manner.

[0307] A-1.3. abbreviation A-3. Synthesis of compounds and intermediates of formula (I) Preparation Example 1 Preparation of 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one (compound I-001) Step 1 Preparation of N-[(2RS)-1-chloro-3-(3,4-dimethylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)-2-methyl-3-oxo-2,3-dihydropyridazine-4-carboxamide (intermediate 14-001) Under argon atmosphere, in a 50 mL double-necked round-bottom flask, at 0 °C, a solution of HATU (575 mg, 1.46 mmol) in 2 mL of anhydrous DMF was added to a solution of 5-(3-cyclopropylphenoxy)-2-methyl-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (400 mg, 1.39 mmol) in 4 mL of anhydrous DMF. The resulting mixture was stirred at 0 °C for 15 min, and then (2RS)-1-chloro-3-(3,4-dimethylphenyl)prop-2-amine hydrochloride (1:1) (343 mg, 1.46 mmol) and DIPEA (0.73 mL, 4.19 mmol) were added. After reacting at 0 °C for 30 min, the reaction mixture was heated to room temperature. After 1 hour, the reaction mixture was poured into brine and extracted with ethyl acetate. The combined organic layers were dried over a ChemElut column and concentrated under vacuum. The crude product was rapidly purified by chromatography (10% to 55% ethyl acetate in n-heptane solution) to give the title compound (543 mg, 99% purity, 83% yield).

[0308] Step 2Preparation of N-[(2RS)-1-chloro-3-(3,4-dimethylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)-N'-hydroxy-2-methyl-3-oxo-2,3-dihydropyridazine-4-formamidinium (intermediate 15-001) Under an argon atmosphere, PCl5 was added at room temperature to a 50 mL double-necked round-bottom flask at 0 °C to a solution of N-[(2RS)-1-chloro-3-(3,4-dimethylphenyl)propyl-2-yl]-5-(3-cyclopropylphenoxy)-2-methyl-3-oxo-2,3-dihydropyridazine-4-carboxamide (intermediate 14-001, 421 mg, 0.9 mmol) in 9 mL of toluene. The reaction mixture was stirred at 80 °C for 1 hour and then cooled to room temperature. The reaction mixture was then added dropwise to 10 mL of NH2OH (50%) aqueous solution and stirred for 20 minutes. Finally, the reaction mixture was poured into 30 mL of 6N HCl aqueous solution to pH = 1. The aqueous layer was extracted with ethyl acetate, dried over a ChemElut column, and concentrated under vacuum. The crude product was rapidly purified by chromatography (30% to 100% ethyl acetate in heptane solution) and then concentrated under vacuum to obtain the title compound (174 mg, 94% purity, 37% yield).

[0309] Step 3 Preparation of 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one (compound I-001) N-[(2RS)-1-chloro-3-(3,4-dimethylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)-N'-hydroxy-2-methyl-3-oxo-2,3-dihydropyridazine-4-formamidinium (intermediate 15-001) (174 mg, 0.36 mmol) was dissolved in 3.6 mL of isopropanol. Then, 470 µL of 1N NaOH solution was added, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was rapidly poured into brine, extracted with ethyl acetate, dried over a ChemElut column, and concentrated under vacuum. The crude product was rapidly purified by chromatography (50% to 100% ethyl acetate in heptane), and then concentrated under vacuum to give the title compound (39 mg, 90% purity, 22% yield).

[0310] The compounds in Table 1 were prepared according to or similar to the preparation examples.

[0311] Table 1 Compounds according to formula (I) (I) Table 2 Compounds of formula (I) 1 H-NMR The compounds of formula (I) below can be prepared according to or similar methods described above: - 5-(3-chlorophenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chlorophenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, - 4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one, and - 4-[(5RS)-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-3(2H)-one.

[0312] Table 3 Compounds according to formula (14) (14) Table 4 The compound of formula (14) 1 H-NMR Table 5 Compounds according to formula (15) (15) Table 6 The compound of formula (15) 1 H-NMR B. Biological Examples B-1. against Botrytis cinerea ( Botrytis cinerea In vivo prophylactic test of (gray mold) Solvent: 5% (v / v) dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 µl per mg of active ingredient (Tween) ® 80 The active ingredient is in dimethyl sulfoxide / acetone / Tween ® Dissolve and homogenize in an 80% mixture, then dilute in water to the desired concentration.

[0313] Young cucumber or cabbage plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated with only acetone / dimethyl sulfoxide / Tween. ® Treatment with an 80% aqueous solution.

[0314] Twenty-four hours later, the plants were infected by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. Infected cucumber plants were then cultured at 17°C and 90% relative humidity for 4 to 5 days. Infected cabbage plants were cultured at 20°C and 100% relative humidity for 4 to 5 days.

[0315] The experiment was evaluated 4 to 5 days after inoculation. 0% indicates efficacy equivalent to the control plant, while 100% efficacy indicates no disease was observed.

[0316] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0317] B-2. For round-spotted coelom bacilli ( Pyrenophora teres In vivo prophylactic test of (barley web spot disease) Solvent: 5% (v / v) dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 µl per mg of active ingredient (Tween) ® 80 The active ingredient is in dimethyl sulfoxide / acetone / Tween ® Dissolve and homogenize in an 80% mixture, then dilute in water to the desired concentration.

[0318] Young barley plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated with only acetone / dimethyl sulfoxide / Tween. ® Treatment with an 80% aqueous solution.

[0319] Twenty-four hours later, the plants were infected by spraying the leaves with an aqueous suspension of Cynocor spores. The infected barley plants were then incubated at 20°C and 100% relative humidity for 48 hours, followed by incubation at 20°C and 70-80% relative humidity for 8 days.

[0320] The experiment was evaluated 10 days after inoculation. 0% indicates efficacy equivalent to the control plant, while 100% efficacy indicates no disease was observed.

[0321] In this experiment, the following compound of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: I-001.

[0322] In this experiment, the following compounds of the present invention showed efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: I-002; I-003.

[0323] In this experiment, the following compound of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-004.

[0324] B-3. For powdery mildew ( Sphaerotheca fuliginea In vivo preventive test of powdery mildew in cucurbits Test Solvent: 5% (v / v) dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 µl per mg of active ingredient (Tween) ® 80 The active ingredient is in dimethyl sulfoxide / acetone / Tween ® Dissolve and homogenize in an 80% mixture, then dilute in water to the desired concentration.

[0325] Cucumber seedlings were treated by spraying with the active ingredients prepared as described above. Control plants were treated with only acetone / dimethyl sulfoxide / Tween. ® Treatment with an 80% aqueous solution.

[0326] Twenty-four hours later, the plants were infected by spraying the leaves with an aqueous suspension of powdery mildew spores. The infected cucumber plants were then cultured for 8 days at 20°C and 70-80% relative humidity.

[0327] The experiment was evaluated 8 days after inoculation. 0% indicates efficacy equivalent to the control plant, while 100% efficacy indicates no disease was observed.

[0328] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0329] B-5. Anthracnose of the common bean ( Colletotrichum lindemuthianum (Bean leaf spot disease) in vivo prevention Protective testing Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 µL per mg of active ingredient (Tween) ® 80 The active ingredient is in dimethyl sulfoxide / acetone / Tween ® Dissolve and homogenize in an 80% mixture, then dilute in water to the desired concentration.

[0330] Young beans were treated by spraying with the active ingredients prepared as described above. Control plants were treated with only acetone / dimethyl sulfoxide / Tween. ® The solution was treated with an 80% aqueous solution.

[0331] Twenty-four hours later, the plants were infected by spraying the leaves with an aqueous suspension of bean anthracnose spores. The infected bean plants were then incubated at 20°C and 100% relative humidity for 24 hours, and then at 20°C and 90% relative humidity for 6 days.

[0332] The experiment was evaluated 7 days after inoculation. 0% indicates efficacy equivalent to the control plant, while 100% efficacy indicates no disease was observed.

[0333] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-003; I-004; I-005; I-006; I-007.

[0334] B-6. Alternaria ( Alternaria alternata In vitro cell experiments Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0335] Preparation of Alternaria ( A. alternata ) spore suspension and diluted to the desired spore density.

[0336] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 5 days of incubation, mycelial growth was measured using spectrophotometry to determine the fungal toxicity of the compound. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0337] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0338] B-6. Fusarium oxysporum ( Fusarium culmorum In vitro cell experiments Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0339] Preparation of yellow Fusarium ( F. culmorum ) spore suspension, and diluted to the desired spore density.

[0340] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 4 days of incubation, the fungicidal toxicity was determined by measuring mycelial growth using spectrophotometry. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0341] B-8. Inari spores ( Pyricularia oryzae In vitro cell experiments Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0342] Preparation of rice pear spores ( P. oryzae ) spore suspension, and diluted to the desired spore density.

[0343] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 5 days of incubation, mycelial growth was measured using spectrophotometry to determine the fungal toxicity of the compound. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0344] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004.

[0345] B-9. Anthracnose of the common bean ( Colletotrichum lindemuthianum In vitro cell experiments Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0346] Preparation of common bean anthrax bacteria ( C. lindemuthianum ) spore suspension, and diluted to the desired spore density.

[0347] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 6 days of incubation, the fungicidal toxicity was determined by measuring mycelial growth using spectrophotometry. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0348] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0349] B-10. Wheat shell needle spore ( Septoria tritici In vitro cell experiments Solvent: DMSO Culture medium: 1 g KH₂PO₄ (VWR), 1 g K₂HPO₄ (VWR), 0.5 g urea (VWR), 3 g KNO₃ (Prolabo), 10 g sucrose (VWR), 0.5 g MgSO₄, 7H₂O (Sigma), 0.07 g CaCl₂, 2H₂O (Prolabo), 0.2 mg MnSO₄, H₂O (Sigma), 0.6 mg CuSO₄, 5H₂O (Sigma), 7.9 mg ZnSO₄, 7H₂O (Sigma), 0.1 mg H₃BO₃ (Merck), 0.14 mg NaMoO₄, 2H₂O (Sigma), 2 mg thiamine (Sigma), 0.1 mg anorthite (VWR), 4 mg FeSO₄, 7H₂O (Sigma), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0350] Preparation of wheat shell needle spores ( S. tritici ) spore suspension, and diluted to the desired spore density.

[0351] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 7 days of incubation, the fungicidal toxicity was determined by measuring mycelial growth using spectrophotometry. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0352] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-002; I-005; I-006; I-007.

[0353] B-11. against Brassica oleracea (Alternaria brassicae) Alternaria brassicae (Leaf spot disease of radishes or cabbages) in the body Preventive testing Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 µL per mg of active ingredient, Tween® 80 The active ingredient is in dimethyl sulfoxide / acetone / Tween ® Dissolve and homogenize in an 80% mixture, then dilute in water to the desired concentration.

[0354] Young radish or cabbage plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated with only acetone / dimethyl sulfoxide / Tween. ® The solution was treated with an 80% aqueous solution.

[0355] Twenty-four hours later, the plants were infected by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The infected radish or cabbage plants were then incubated at 20°C and 100% relative humidity for 3 to 4 days.

[0356] The experiment was evaluated 3 to 4 days after inoculation. 0% indicates efficacy equivalent to the control plant, while 100% efficacy indicates no disease was observed.

[0357] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0358] B-12. Round-screed coelom ( Pyrenophora teres In vitro cell experiments Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0359] Preparation of round-crystal bacteria ( P. teres ) spore suspension, and diluted to the desired spore density.

[0360] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 6 days of incubation, the fungicidal toxicity was determined by measuring mycelial growth using spectrophotometry. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0361] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0362] B-13. Botrytis cinerea ( Botrytis cinerea In vitro cell experiments Solvent: DMSO Culture medium: 1 g KH₂PO₄ (VWR), 1 g K₂HPO₄ (VWR), 0.5 g urea (VWR), 3 g KNO₃ (Prolabo), 10 g sucrose (VWR), 0.5 g MgSO₄, 7H₂O (Sigma), 0.07 g CaCl₂, 2H₂O (Prolabo), 0.2 mg MnSO₄, H₂O (Sigma), 0.6 mg CuSO₄, 5H₂O (Sigma), 7.9 mg ZnSO₄, 7H₂O (Sigma), 0.1 mg H₃BO₃ (Merck), 0.14 mg NaMoO₄, 2H₂O (Sigma), 2 mg thiamine (Sigma), 0.1 mg anorthite (VWR), 4 mg FeSO₄, 7H₂O (Sigma), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0363] Preparation of Botrytis cinerea ( B. cinerea ) spore suspension, and diluted to the desired spore density.

[0364] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 6 days of incubation, the fungicidal toxicity was determined by measuring mycelial growth using spectrophotometry. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0365] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004; I-005; I-006; I-007.

[0366] B-14. Fusarium oxysporum ( Fusarium culmorum In vitro cell experiments Solvent: DMSO Culture medium: 1 g KH₂PO₄ (VWR), 1 g K₂HPO₄ (VWR), 0.5 g urea (VWR), 3 g KNO₃ (Prolabo), 10 g sucrose (VWR), 0.5 g MgSO₄, 7H₂O (Sigma), 0.07 g CaCl₂, 2H₂O (Prolabo), 0.2 mg MnSO₄, H₂O (Sigma), 0.6 mg CuSO₄, 5H₂O (Sigma), 7.9 mg ZnSO₄, 7H₂O (Sigma), 0.1 mg H₃BO₃ (Merck), 0.14 mg NaMoO₄, 2H₂O (Sigma), 2 mg thiamine (Sigma), 0.1 mg anorthite (VWR), 4 mg FeSO₄, 7H₂O (Sigma), 1 liter QSP Inoculum: Spore suspension The fungicide was dissolved in DMSO, and the solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤1%.

[0367] Preparation of yellow Fusarium ( F. culmorum ) spore suspension, and diluted to the desired spore density.

[0368] In liquid culture assays, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 5 days of incubation, mycelial growth was measured using spectrophotometry to determine the fungal toxicity of the compound. The inhibitory effect on fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0369] In this experiment, the following compounds of the present invention showed efficacy of 80% to 89% at an active ingredient concentration of 50 µMol / l: I-001; I-002; I-003; I-004.

[0370] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 50 µMol / l: I-005; I-006.

Claims

1. Compounds of formula (I) and their N-oxides, salts, hydrates, and hydrates of salts and N-oxides: ， in R 3 and R 4 Independently hydrogen, fluorine, or C1-C4-alkyl, R 5 It is hydrogen or C1-C4-alkyl. L represents a direct bond or a C1-C4-alkylene bond. in The C1-C4-alkylene group is optionally substituent by one or two L groups. SA replace, L SA It is fluorine. or Two substituents L bonded to the same carbon atom SA Together with the carbon atoms they are attached to, they form cyclopropyl rings or cyclobutyl rings. R 6 For C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic, 5 to 14-membered heteroaryl, C3-C 12 -Carbocyclic oxide, C6-C 14 -aryloxy, 5 to 14-membered heteroaryloxy, 3 to 14-membered heterocyclic oxy, C3-C 12 -Carbocyclic thiogroup, C6-C 14 -arylthio, 5 to 14-membered heteroarylthio, 3 to 14-membered heterocyclic thio, C1-C3-alkoxy, C1-C3-haloalkoxy, The C1-C3-alkoxy and C1-C3-haloalkoxy groups are substituted by one substituent selected from the following: C3-C 12 -Carbocyclic group, C6-C 14 -aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl The C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl are optionally surrounded by 1 to 3 R 6S Substituent substitution, Among them, C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3 to 14-membered heterocyclic, 5 to 14-membered heteroaryl, C3-C 12 -Carbocyclic oxide, C6-C 14 -aryloxy, 5 to 14-membered heteroaryloxy, 3 to 14-membered heterocyclic oxy, C3-C 12 -Carbocyclic thiogroup, C6-C 14 -Arylthio, 5- to 14-membered heteroarylthio and 3- to 14-membered heterocyclic thio groups are optionally surrounded by 1 to 3 R groups. 6S Substituent substitution, in R 6S Independently selected from: halogen, cyano, nitro, hydroxyl, sulfhydryl, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5 or 6-membered heteroaryl, 3 to 7-membered heterocyclic, -C(=O)(OR 17 ) and -C(=O)N(R 18 )2, The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, C1-C6-alkylthio and C1-C6-haloalkylthio are optionally substituted by one to three independent substituents selected from: fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl. and Among them, C3-C6-cycloalkylthiol, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic groups are optionally substituted by 1 to 3 independent substituents selected from: fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, And among them R 17 and R 18 Independently hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl, The C1-C4-alkyl or C1-C4-haloalkyl group is optionally substituted by one to three substituents independently selected from the following: fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl. R 7 The group is selected from C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, methylformyl, tert-butylformyl, 2-(dimethylamino)-2-oxo-ethyl, 2-(methylamino)-2-oxo-ethyl, phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thiophene, isoxazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, or triazinyl; wherein any one of the phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thiophene, isoxazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, and triazinyl groups is unsubstituted or is substituented by one or two independently selected from the following groups R. 8 Substitution: halogen, mercapto, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, or C1-C3-alkylsulfonyl; or R 7 For CR 12 R 13 R 14 ,in R 12 and R 13 Independently selected from hydrogen or methyl; or R 12 and R 13 Together with the carbon atoms they are attached to, they form cyclopropyl groups; and R 14 Selected from cyano, methylformyl, 2-(dimethylamino)-2-oxo-ethyl or 2-(methylamino)-2-oxo-ethyl; or R 14 The phenyl group is a heteroaryl group selected from pyridinyl, pyrimidinyl, pyridazinyl, triazolyl, thiazolyl, oxazolyl, imidazolyl, thiophene, furanyl, isoxazolyl, oxadiazolyl, and thiadiazolyl, or a heterocyclic group selected from oxadiazyl, aziridine, aziridine, piperidinyl, piperazinyl, tetrahydrofuranyl, tetrahydropyranyl, morpholinyl, and dioxahexacyclic; wherein any one of the phenyl, heteroaryl, and heterocyclic groups is unsubstituted or substituented by one or two independently selected from the following substituents R. 9 Substitution: halogen, mercapto, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C4-alkynyl or C1-C4-alkylsulfonyl; Q represents phenyl, naphthyl, C3-C 10 -Carbocyclic, 5- to 10-membered heterocyclic or 5- to 10-membered heteroaryl Among them, phenyl, naphthyl, C3-C 10 - A carbocyclic group, a 5- to 10-membered heterocyclic group, and a 5- to 10-membered heteroaryl group are optionally replaced by 1 to 3 substituents Q. S replace, in Q S Independently selected from halogen, cyano, nitro, formyl, carboxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, 3- to 7-membered heterocyclic, phenyl, 5- or 6-membered heteroaryl. in The C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylthio, C1-C The 4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, and C1-C4-haloalkylsulfonyl groups are optionally substituted by one to three independent substituents selected from the following: cyano, amino, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and 3 to 7-membered heterocyclic groups. The C3-C6-cycloalkyl, 3- to 7-membered heterocyclic, phenyl, and 5- or 6-membered heteroaryl groups are optionally substituted by 1 to 3 independent substituents selected from the following: fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, and C3-C6-cycloalkyl.

2. The compound of formula (I) according to claim 1, its salt, hydrate, and salt hydrate, wherein... R 3 and R 4 Independently hydrogen, fluorine, or methyl, R 5 It is hydrogen. L represents a straight link, methylene, 1,1-ethylene, or 1,2-ethylene. in The methylene, 1,1-ethylene, and 1,2-ethylene are optionally substituted with one or two L-substituents. SA replace, L SA It is fluorine. or Two substituents L bonded to the same carbon atom SA Together with the carbon atoms they are attached to, they form cyclopropyl rings or cyclobutyl rings. R 6 It can be indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanecyclohexenyl, furanyl, thiophene, indoleyl, or benzofuranyl. Indene, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanecyclohexenyl, furanyl, thiophene, indoleyl, and benzofuranyl are optionally surrounded by one or two R groups. 6S Substituent substitution, in, R 6S Independently selected from: fluorine, chlorine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetaneyl, tetrahydrofuranyl, pyrazolyl, and pyridinyl. The C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, and C2-C4-alkynyl groups are optionally substituted by one or two independent substituents selected from the following: hydroxyl and C1-C4-alkoxy. and The C3-C6-cycloalkyl, oxetyl, tetrahydrofuranyl, pyrazolyl, and pyridyl groups are optionally substituted by one or two independent substituents selected from the following: fluorine, chlorine, and C1-C4-alkyl. R 7 Selected from C1-C4-alkyl or CR 12 R 13 R 14 ,in R 12 and R 13 Independently selected from hydrogen or methyl; and R 14 The group is selected from cyano, methylformyl, 2-(methylamino)-2-oxo-ethyl, phenyl, heteroaryl groups selected from pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, or heterocyclic groups selected from pyrrolidinyl, piperidinyl, and tetrahydropyranyl; wherein any one of the phenyl, heteroaryl, and heterocyclic groups is unsubstituted or substituented by one or two independently selected from the following groups R. 9 Substitution: fluorine, chlorine, cyano, methyl, ethyl, methoxy, or cyclopropyl; Q is phenyl, thiophene, or pyridinyl. The phenyl, thiophene, and pyridyl groups are optionally substituents of one or two groups. S replace, in Q S Independently selected from halogens, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, and C3-C6-cycloalkyl. in The C3-C6-cycloalkyl group is optionally substituted by one or two independent substituents selected from the following: fluorine, chlorine, and methyl.

3. The compound of formula (I) according to claim 1 or 2, its salt, hydrate, and hydrate of the salt, wherein... R 6 It is a phenyl group. The phenyl group is optionally surrounded by one or two R groups. 6S Substituent substitution, in R 6S It is independently selected from fluorine, chlorine, C1-C4-alkyl, difluoromethyl and trifluoromethyl.

4. The compound of formula (I) according to any one of claims 1-3, its salt, hydrate, and hydrate of the salt, wherein... R 3 and R 4 It is hydrogen. R 5 It is hydrogen. L stands for methylene. R 6 Groups that are the following: , , or , in § 1 For the point connected to L, R 6S1 It is chlorine or methyl. R 6S2 It is chlorine or methyl. R 7 It is methyl. Q is a group in the following formula: in § 2 The point where it connects to the oxygen atom. Q S1 It is hydrogen or fluorine. Q S2 It can be chlorine, fluorine, methyl, trifluoromethyl, or cyclopropyl.

5. The compound of formula (I) according to any one of claims 1-4, wherein the compound of formula (I) is selected from: - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-chlorophenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chlorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-5-(3-cyclopropylphenoxy)-2-methylpyridazine-3(2H)-one, - 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one, - 5-(3-chloro-2-fluorophenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine-3-yl]-2-methylpyridazine-3(2H)-one.

6. A composition for controlling plant pathogenic harmful fungi, comprising at least one compound of formula (I) according to any one of claims 1 to 5 and at least one carrier and / or surfactant.

7. A method for controlling harmful microorganisms in crop protection and material protection, characterized in that... Apply at least one compound of formula (I) according to any one of claims 1 to 5 and / or the composition according to claim 6 to harmful microorganisms and / or their habitats.

8. The method according to claim 7, wherein the harmful microorganism is a pathogenic oomycete or plant pathogenic fungus selected from the genus *Cyclocarya* (…). Podosphaera ) species, genus of monothecota ( Sphaerotheca ) species, genus *Hylocereus* ( Uncinula ) species, genus *Russula* ( Gymnosporangium ) species, genus Camel rust ( Hemileia ) species, genus of rust fungi ( Phakopsora ) species, genus Stipe rust ( Puccinia ) species, genus *Russula* ( Uromyces ) species, genus *White Rust* ( Albugo ) species, genus *Peronospora* Bremia ) species, genus Peronospora ( Peronospora ) species, Phytophthora ( Phytophthora ) species, genus Peronospora ( Plasmopara ) species, genus *Pseudomonas* Pseudoperonospora ) species, genus Pythium ( Pythium ) species, Alternaria genus ( Alternaria ) species, Cercospora ( Cercospora ) species, genus Cladosporium ( Cladiosporum ) species, genus Cyclospora ( Cochliobolus ) species, genus Cladosporium ( Corynespora )kind, Cycloconium Species, genus Interstellate ( Diaporthe ) species, genus *Cryptococcus* ( Elsinoe ) species, genus *Palmaria* ( Gloeosporium ) species, genus *Ceratophyllum* ( Glomerella ) species, genus *Plasmodium* ( Guignardia ) species, Micrococcus genus ( Leptosphaeria ) species, genus Giant Seat Shell ( Magnaporthe ) species, Micrococcus genus ( Microdochium ) species, genus Coccidioides ( Mycosphaerella ) species, genus *Cyclocarya* ( Phaeosphaeria ) species, genus *Sclerotium* (Pyrenophora ) species, genus *Pseudomonas* ( Ramularia ) species, genus *Rhizophora* ( Rhynchosporium ) species, genus *Syngonium* ( Septoria ) species, genus Polysporus ( Stagonospora ) species, genus *Russula* ( Typhula ) species, genus *Nepeta* ( Venturia ) species, genus *Foucault* ( Corticium ) species, Fusarium genus ( Fusarium ) species, genus *Tetranychus* Gaeumannomyces ) species, genus Plasmodium ( Plasmodiophora ) species, Rhizoctonia genus ( Rhizoctonia ) species, genus *Cladosporium* Sarocladium ) species, genus Microsclerotium ( Sclerotium )kind, Tapesia Species, Rhizophora genus ( Thielaviopsis ) species, Aspergillus genus ( Aspergillus ) species, genus Clavicipitaceae ( Claviceps ) species, genus Fusarium ( Gibberella )kind, Monographella Species, genus Polysporus ( Stagonospora ) species, genus *Ustilago maydis* Sphacelotheca ) species, genus *Ustilago maydis* Tilletia ) species, genus *Ustilago maydis* Urocystis ) species, genus Ustilago ( Ustilago ) species, genus *Streptococcus* ( Monilinia ) species, Penicillium genus ( Penicillium ) species, Rhizopus genus ( Rhizopus ) species, genus Sclerotium ( Sclerotinia ) species, Verticillium genus ( Verticilium ) species, genus Hymenops ( Aphanomyces ) species, genus Dicellae ( Ascochyta ) species, genus Cladosporium ( Cladosporium ) species, genus *Cyclophorus* ( Macrophomina ) species, genus Stem-point mold ( Phoma ) species, genus *Pseudomonas* Phomopsis ) species, genus Pyrethrum ( Pyricularia ) species, Verticillium genus ( Verticillium ) species, genus *Cryptostoma* ( Nectria ) species, genus of exobasidium ( Exobasidium ) species, genus Exocystis ( Taphrina )kind, Esca Species, Ganoderma ( Ganoderma ) species, genus Helicobacter ( Helminthosporium ) species, Xanthomonas genus ( Xanthomonas ) species, Pseudomonas genus ( Pseudomonas ) species, Erwinia genus ( Erwinia ) species, genus Bacillus phloem Liberibacter ) species, genus Xylobacterium ( Xyella ) species, Ralstonia solanacearum genus ( Ralstonia ) species, Dictyopsis genus ( Dickeya ) species, Corynebacterium genus ( Clavibacter ) species, genus Streptomyces ( Streptomyces )kind, Colletotrichum gloeosporoides dematium var. truncatum Funnel-shaped mold ( Choanephora infundibulifera ) trispora (synonym) name , Dactuliophora glycines Soybean endospermum spores ( Drechslera glycini ), Clover Small Glossy Shell ( Leptosphaerulina trifolii ), Soybean leaf spot ( Phyllosticta sojaecola ), soybean powdery mildew ( Microsphaera diffusa Soybean red leaf spot pathogen ( Pyrenochaeta glycines ), Soybean scab rounds ( Sphaceloma glycines ), creeping mold ( Stemphylium botryosum ), Wild Lily Red Shell ( Calonectria crotalariae ), Mycoleptodiscus terrestris 、Invasion of new red shell ( Neocosmospora vasinfecta ) and soybean stem brown rot fungus ( Phialophora gregata ).

9. The method according to claim 7 or 8, wherein the harmful microorganism is a plant pathogenic fungus selected from the following: *Erysiphe monotypicum* (… Sphaerotheca fuliginea Alternaria ( Alternaria alternata ), Inari spores ( Pyricularia oryzae ), Brassica oleracea ( Alternaria brassicae ) and yellow Fusarium ( Fusarium culmorum ).

10. Use of one or more compounds of formula (I) according to any one of claims 1 to 5 and / or compositions according to claim 6 for the control of harmful microorganisms in crop protection and material protection.

11. Methods for preparing compounds of formula (Ia) Where R 3 R 4 R 5 R 6 R 7 L and Q are as defined in any one of claims 1 to 5. Its features are, Compounds of formula (1): Where R 7 And Q is as defined above, and U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. Reaction with one of the amines or salts of formula (13) Where R 3 R 4 R 5 R 6 And L is as defined above, and E 1 It is a hydroxyl group or a halogen. W is a hydrogen or amino protecting group, such as tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. To obtain the compound of formula (14): ， Where R 3 R 4 R 5 R 6 R 7 E 1 L, W, and Q are as defined above. The compound of formula (14) is then treated with a dehydrating agent, followed by treatment with hydroxylamine to form the compound of formula (15): ， Where R 3 R 4 R 5 R 6 R 7 E 1 L, Q, and W are as defined above. When E 1 When it is a hydroxyl group, The compound of formula (15) is converted into the compound of formula (Ia) under photoelectrophoresis reaction conditions, or When E 1 When it is halogen, The compound of formula (15) is converted into the compound of formula (Ia) in the presence of a base.

12. Compounds of formulas (14) and (15): (14), and (15) in R 3 R 4 R 5 L, R 6 R 7 And Q as defined in any one of claims 1 to 5, E 1 It is a hydroxyl group or a halogen, preferably a hydroxyl group, chlorine, or bromine. E 2 It is a hydroxyl group, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

13. Compounds of formulas (16) and (17): (16), and (17) in R 3 R 4 R 5 L, R 6 and R 7 As defined in any one of claims 1 to 5, X is a halogen, preferably chlorine or bromine. E 1 It is a hydroxyl group or a halogen, preferably a hydroxyl group, chlorine, or bromine. E 2 It is a hydroxyl group, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

Images