Pyridazine-4-yl oxadiazines as novel fungicides

Abstract

The present invention relates to pyridazine-4-yl oxadiazine compounds and their use for controlling harmful microorganisms such as phytopathogenic oomycetes and fungi.

Description

[0001] This invention relates to pyridazine-4-yloxadiazine and its use in controlling plant pathogenic microorganisms such as plant pathogenic fungi. It 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 offer low toxicity and high selectivity against broad-spectrum plant pathogens (e.g., fungi), or that provide effective pest control even at low application rates. New compounds to prevent the development of resistance may also be desired.

[0003] The present invention provides novel compounds for controlling plant pathogenic microorganisms such as fungi, which are superior to known compounds and compositions in at least some of these respects.

[0004] WO2020 / 127780, WO2021 / 245083, WO2021 / 249995, WO2021 / 245087, WO2021 / 255071, WO2024 / 089191, WO2024 / 132895, WO2024 / 132901 and WO2024 / 143338 disclose oxadiazine compounds with different heterocyclic moieties as bactericides.

[0005] Detailed Explanation Compound of formula (I) This invention relates to compounds of formula (I), their N-oxides, salts, hydrates, and hydrates of said salts and said N-oxides: in R 3 and R 4 Independently hydrogen, fluorine, or C1-C4-alkyl, R 5 It is hydrogen. L represents a straight bond or a C1-C4-alkylene bond. - wherein the C1-C4-alkylene group is optionally substituted with one or two L-substituents. SA replace, L SA It is fluorine. or Two substituents L attached 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 -Carbocyclothioalkyl, C6-C 14 -arylthioalkyl, 5 to 14-membered heteroarylthioalkyl, 3 to 14-membered heterocyclic thioalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy, - Wherein C1-C3-alkoxy and C1-C3-haloalkoxy are selected from C3-C 12 -Carbocyclic group, C6-C 14 It is substituted by one substituent of -aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl. -- Wherein C3-C 12 -Carbocyclic group, C6-C 14 -Aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl groups are themselves optionally divided by one to three R groups. 6S Substituent substitution, - Where 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 -Carbocyclothioalkyl, C6-C 14 -arylthioalkyl, 5 to 14-membered heteroarylthioalkyl, 3 to 14-membered heterocyclic thioalkyl optionally surrounded by one to three R 6S Substituent substitution, in R 6S Independently selected from halogen, cyano, nitro, hydroxyl, mercapto, pentafluorothioalkyl, 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-alkylthioalkyl, C1-C6-haloalkylthioalkyl, C3-C6-cycloalkylthioalkyl, 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, - wherein, 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-alkylthioalkyl, and C1-C6-haloalkylthioalkyl are optionally substituted by one to three substituents independently selected from fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl. - and - Among them, C3-C6-cycloalkylthioalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic basic units are optionally substituted by one to three independent substituents selected from fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy. in R 17 and R 18 Independently hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl. - wherein the C1-C4-alkyl or C1-C4-haloalkyl group is optionally substituted by one to three substituents independently selected from fluorine, chlorine, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl. R 7 It is hydrogen, fluorine, chlorine or C1-C4-alkyl, R 8 It is hydrogen, halogen, or C1-C4-alkyl. Q represents phenyl, naphthyl, or C3-C. 10 -Carbocyclic, 5- to 10-membered heterocyclic or 5- to 10-membered heteroaryl - Including 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 one to three substituents Q. S replace, in Q SIndependently selected from halogens, 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-alkylthioalkyl, C1-C4-haloalkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, 3- to 7-membered heterocyclic groups, phenyl, 5- or 6-membered heteroaryl groups. - Wherein, 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-alkylthioalkyl, C1- The C4-haloalkylthioalkyl, 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, 5- or 6-membered heteroaryl groups are optionally substituted by one to three substituents independently selected from fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl and C3-C6-cycloalkyl groups.

[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] The present 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 a fluorine, chlorine, bromine, or iodine atom.

[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 branched or straight-chain saturated 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 identical or different halogen atoms. 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] 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-cyclo" refer to a monocyclic saturated 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 (from 3 to 8) are carbon atoms and one or more hydrogen atoms are replaced by one or more halogen atoms that may be the same or different.

[0018] As used herein, the term "C2-C6-alkenyl" refers to a branched or straight-chain unsaturated 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-methylpropen-1- -alkenyl, 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-methylpent-4- alkenyl, 4-methylpent-3-enyl, 3-methylpent-3-enyl, 2-methylpent-3-enyl, 1-methylpent-3-enyl, 4-methylpent-2-enyl, 3-methylpent-2-enyl, 2-methylpent-2-enyl, 1-methylpent-2-enyl, 4-methylpent-1-enyl, 3-methylpent-1-enyl, 2-methylpent-1-enyl, 1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-enyl, 3-ethylbut-2-enyl, 2-ethylbut-2-enyl, 1-ethylbut-2 -alkenyl, 3-ethylbut-1-alkenyl, 2-ethylbut-1-alkenyl, 1-ethylbut-1-alkenyl, 2-propylprop-2-alkenyl, 1-propylprop-2-alkenyl, 2-isopropylprop-2-alkenyl, 1-isopropylprop-2-alkenyl, 2-propylprop-1-alkenyl, 1-propylprop-1-alkenyl, 2-isopropylprop-1-alkenyl, 1-isopropylprop-1-alkenyl, 3,3-dimethylprop-1-alkenyl, 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-halogenated alkenyl” means that one or more hydrogen atoms in the C2-C6-alkenyl group 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-haloynyl” means that one or more hydrogen atoms in the C2-C6-ynyl group 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, such as alkoxyalkyl and alkoxyalkoxy.

[0023] As used herein, the term "C1-C6-haloalkoxy" means that one or more hydrogen atoms in the C1-C6-alkoxy group 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, such as cycloalkoxyalkyl groups, that are part of a complex substituent.

[0025] As used herein, the term "C1-C6-alkylthioalkyl" refers to a straight-chain or branched saturated group of the formula (C1-C6-alkyl)-S-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylthioalkyl include, but are not limited to, methylthioalkyl, ethylthioalkyl, propylthioalkyl, isopropylthioalkyl, butylthioalkyl, sec-butylthioalkyl, isobutylthioalkyl, tert-butylthioalkyl, pentylthioalkyl, isopentylthioalkyl, and hexylthioalkyl.

[0026] As used herein, the term “C1-C6-haloalkylthioalkyl” means that one or more hydrogen atoms in a C1-C6-alkylthioalkyl 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-cycloalkylthioalkyl" refers to a monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms bonded to the backbone by sulfur atoms. Examples of monocyclic C3-C8-cycloalkylthioalkyl include, but are not limited to, cyclopropylthioalkyl, cyclobutylthioalkyl, cyclopentylthioalkyl, cyclohexylthioalkyl, cycloheptylthioalkyl, or cyclooctylthioalkyl.

[0028] As used herein, the term “C1-C6-alkylsulfinyl” refers to a straight-chain or branched saturated 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 alkylsulfinyl groups having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, either straight-chain or branched, 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 the C1-C6-alkylsulfinyl group 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 straight-chain or branched saturated 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 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 the C1-C6-alkylsulfonyl group 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 straight-chain or branched saturated 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 the C1-C6-alkoxycarbonyl group 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 ring, spirocyclic, or bridged ring). C3-C 12 -Carbon cyclic groups include, but are not limited to, C3-C 12 -Cycloalkyl (monocyclic or bicyclic), C3-C 12 - Cycloalkenyl (monocyclic or bicyclic), bicyclic systems comprising aryl (e.g., phenyl) fused to a monocyclic C3-C8-cycloalkenyl group (e.g., tetrahydronaphthyl, indanyl, 3-bicyclo[4.2.0]oct-1,3,5-trienyl), bicyclic systems comprising aryl (e.g., phenyl) fused to a monocyclic C3-C8-cycloalkenyl group (e.g., indanyl, dihydronaphthyl), and tricyclic systems comprising a cyclopropyl group linked to the bicyclic system via a carbon atom, wherein the bicyclic system comprises an aryl (e.g., phenyl) fused to a C3-C8-cycloalkenyl group. The C3-C... 12 - A carbon ring can be attached to a portion of the parent molecule by 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 (e.g., bicyclic or tricyclic). Examples of aryl groups include, but are not limited to, phenyl, azulenyl, and naphthyl.

[0038] As used herein, the term "3- to 14-membered heterocyclic group" refers to a 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14-membered saturated or partially unsaturated 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. Heterocycles include, but are not limited to, 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heterocycles. A 3- to 14-membered heterocycle can be attached to a portion of the parent molecule via any carbon or nitrogen atom contained within the heterocycle. Examples of saturated heterocycles include, but are not limited to, 3-membered rings, such as ethylene oxide and aziridine propane; 4-membered rings, such as azetidinyl, oxetanyl, and thietanyl; and 5-membered rings, such as tetrahydrofuranyl, 1,3-dioxacyclopentyl, tetrahydrothiophenyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazole. Alkyl groups; 6-membered rings, such as piperidinyl, hexahydropyridinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxaneyl, tetrahydrothiaranyl, dithiaranyl, morpholinyl, 1,2-oxazohexaneyl, oxothiohexaneyl, thiomorpholinyl; or 7-membered rings, such as oxepanyl, azepanyl, 1,4-diazazohexaneyl, and 1,4-oxazohexaneyl. Examples of unsaturated heterocyclic groups include, but are not limited to, 5-membered rings, such as dihydrofuranyl, 1,3-dioxacyclopentenyl, dihydrothiophenyl, pyrrolinyl, dihydroimidazoyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, and dihydrothiazoyl; 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 group ring” refer to 3, 4, 5, 6 or 7-membered saturated ring systems containing 1, 2 or 3 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples include, but are not limited to, oxirazinyl, aziridinyl, aziridinyl, oxirazinyl, thioridinyl, tetrahydrofuranyl, 1,3-dioxacyclopentyl, tetrahydrothiophenyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, piperidinyl, hexahydropyrimidinyl, hexahydropyrimidinyl, piperazinyl, triazacyclohexyl, hexahydrotriazinyl, tetrahydropyranyl, dioxirazyl, tetrahydrothiaranyl, dithiazolyl, morpholinyl, 1,2-oxaziridinyl, oxothioridinyl, thiomorpholinyl, oxaheptyl, aziridinyl, 1,4-diazacycloheptanyl, and 1,4-oxaziridinyl. Preferred 3- to 7-membered heterocyclic groups are ethylene oxide, aziridine propane, aziridine butane, oxadiazine butane, tetrahydrofuranyl, 1,3-dioxacyclopentane, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxacyclohexane, 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 a monocyclic heteroaryl group as defined herein fused with an aryl group (e.g., phenyl) or a monocyclic heteroaryl group. Examples of bicyclic heteroaryl groups include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridyl, indolazolyl, 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 position (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 heterocyclic groups 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", "3- to 14-membered heterocyclic oxy" are groups representing the formula -OR, where R is the C3-C group 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 -Carbocyclothioalkyl", "C6-C" 14 "-arylthioalkyl", "5- to 14-membered heteroarylthioalkyl", "3- to 14-membered heterocyclic thioalkyl" are groups represented by the formula -SR, where R is C3-C as defined herein. 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 removed from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate (“triflate”) group, an alkoxy group, a methanesulfonate, or a p-toluenesulfonate.

[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 hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid), 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 complexes 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-linked bond, methylene, 1,1-ethylene, or 1,2-ethylene. - wherein 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 attached 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, dihydrobenzodioxanedienyl, furanyl, thiophene, indoleyl, or benzofuranyl. - wherein, indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanedienyl, furanyl, thiophene, indoleyl, and benzofuranyl are optionally represented by one or two R 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-ynyl, C3-C6-cycloalkyl, oxetaneyl, tetrahydrofuranyl, pyrazolyl, and pyridinyl. - wherein 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 hydroxyl and C1-C4-alkoxy groups. - and - Wherein the C3-C6-cycloalkyl, oxetyl, tetrahydrofuranyl, pyrazolyl, and pyridinyl groups are optionally substituted by one or two independent substituents selected from fluorine, chlorine, and C1-C4-alkyl groups. R 7 It can be hydrogen, fluorine, chlorine, or methyl. R 8 It can be hydrogen, fluorine, chlorine, or methyl. Q is phenyl, thienyl, or pyridyl. - wherein the phenyl, thiophene, and pyridyl groups are optionally substituents of one or two groups Q. 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. - The C3-C6-cycloalkyl group is optionally substituted by one or two substituents selected independently from fluorine, chlorine and methyl.

[0055] More preferably, the present invention relates to compounds of formula (I) and their salts, hydrates and salt hydrates, wherein R 3 and R 4 It is hydrogen. R 5 It is hydrogen. L stands for methylene. R 6 Groups of the following formula in 1 For connection with L, R 6S1 It is chlorine, bromine or methyl. R 6S2 It is chlorine, bromine or methyl. R 7 It is hydrogen. R 8 It can be hydrogen, chlorine, or methyl. Q is a group in the following formula in 2 For the bond with the oxygen atom, Q S1 It is hydrogen or fluorine. Q S2 It can be chloro, methyl, trifluoromethyl or cyclopropyl.

[0056] More preferably, the present invention relates to compounds of formula (I) and their salts, hydrates, and hydrates of said salts, wherein R 3 and R 4 For hydrogen R 5 It is hydrogen. L stands for methylene. R 6 Groups of the following formula in 1 For connection with L, R 6S1 It is chlorine, bromine or methyl. R 6S2 It is chloro, bromine, methyl, or isoprene. R 7 It is hydrogen. R 8 It is hydrogen or methyl. Q is a group in the following formula. in 2 For the bond with the oxygen atom, Q S1 It is hydrogen or fluorine. Q S2 It can be chlorinated, trifluoromethyl, isoprenyl, or cyclopropyl.

[0057] Even more preferably, the present invention relates to compounds of formula (I) and their salts, hydrates and hydrates of said salts, wherein the compound of formula (I) is one of the following compounds: (5RS)-3-[5-(3-chlorophenoxy)pyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)pyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-bromo-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(4-bromo-2-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2,4-dimethylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(3,4-dimethylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-chlorophenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(3,4-dimethylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)-3-methylpyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2,4-dimethylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-[2-methyl-4-(prop-1-en-2-yl)benzyl]-3-{3-methyl-5-[3-(prop-1-en-2-yl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)pyridazin-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)pyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)pyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine More preferably, the present invention relates to compounds of formula (I) and their salts, hydrates and hydrates of said salts, wherein the compound of formula (I) is one of the following compounds: (5RS)-3-[5-(3-chlorophenoxy)pyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)pyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-bromo-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(4-bromo-2-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)pyridazine-4-yl]-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dichlorobenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2,4-dimethylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(3,4-dimethylbenzyl)-3-{5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-chlorophenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(3,4-dimethylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)-3-methylpyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-cyclopropylphenoxy)-3-methylpyridazine-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chlorophenoxy)-3-methylpyridazine-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-(2,4-dimethylbenzyl)-3-{3-methyl-5-[3-(trifluoromethyl)phenoxy]pyridazine-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (5RS)-5-[2-methyl-4-(prop-1-en-2-yl)benzyl]-3-{3-methyl-5-[3-(prop-1-en-2-yl)phenoxy]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine.

[0058] Most preferably, the present invention relates to compounds of formula (I), wherein compounds of formula (I) are as follows: (5RS)-5-(2-bromo-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine.

[0059] More preferably, L is a direct-connect key, and R 6 It can be indanyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanedieneyl, indoleyl, or benzofuranyl. Among them, indanyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanedienyl, indoleyl, and benzofuranyl are optionally represented by one or two R. 6S Substituent substitution, in R 6S It is independently selected from fluorine, chlorine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-ynyl, C3-C6-cycloalkyl, oxetaneyl, tetrahydrofuranyl, pyrazolyl and pyridinyl.

[0060] Similarly, even more preferably, R 6 It is a phenyl group. Where the phenyl group is formed by one or two R groups 6S Substituent substitution, in R 6S It is independently selected from chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, allyl and isoprene.

[0061] Even more preferably, R 6 Groups of the following formula in 1 For connection with L, R 6S1 It is chlorine, bromine or methyl. R 6S2 It can be chlorine, bromine, or methyl.

[0062] Even more preferably, R 3 and R 4 For hydrogen, R 5 It is hydrogen, and L is methylene.

[0063] Even more preferably, L is methylene.

[0064] Even more preferably, R 7 For hydrogen, and R 8 It can be hydrogen, chlorine, or methyl.

[0065] Even more preferably, Q is a group in the following formula in 2 For the bond with the oxygen atom, Q S1 It is hydrogen or fluorine. Q S2 It can be chlorine, trifluoromethyl, isopentenyl, or cyclopropyl.

[0066] The above R 3 R 4 R 5 R 6 R 7 R 8 The detailed definitions of L and Q (broad definitions as well as preferred, more preferred, and even more preferred definitions) can be combined in various ways. These combinations of definitions thus provide subclasses of the compounds of the present invention, such as those disclosed below.

[0067] The compounds of formula (I) can be used as fungicides (for the control of plant pathogenic fungi), and in particular as methods for the control of plant pathogenic fungi, the methods comprising the step of applying one or more compounds of formula (I) to a plant, plant part, seed, fruit or soil in which the plant grows.

[0068] 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, the group R... 3 R 4 R 5 R 6 R 7 R 8L 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.

[0069] Compounds of formula (Ia) are various subsets of formula (I).

[0070] Compounds of formula (I) can be prepared by various routes similar to known methods (see, for example, and references therein). Non-limiting examples of suitable methods are described herein.

[0071] Compounds of formula (I) can be obtained directly by performing methods A through E, or by conversion or derivatization of another compound of formula (I) prepared according to the methods described herein. For example, a compound of formula (I) can be converted into another compound of formula (I) by substituting one or more substituents of the starting compound of formula (I) with other substituents.

[0072] The methods described herein can be carried out using one or more inert organic solvents, which are conventional solvents 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, petroleum ether, 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 pentyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-ethoxyethane, or anisole); ketones (e.g., acetone, methyl ethyl ketone, 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- or isobutyronitrile or benzonitrile); amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, N-methylN-formylaniline, N-methylpyrrolidone or hexamethylphosphotriamide); 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.

[0073] Some of the methods described herein may require, or optionally use, 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 include potassium tert-butoxide, 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).

[0074] 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.

[0075] Suitable copper salts or complexes and their hydrates include, but are not limited to, copper metal, cuprous iodide (I), cuprous chloride (I), cuprous bromide (I), cuprous chloride (II), cuprous bromide (II), copper oxide (II), cuprous oxide (I), copper acetate (II), cuprous acetate (I), cuprous thiophene-2-carboxylate (I), cuprous cyanide (I), copper sulfate (II), copper bis(2,2,6,6-tetramethyl-3,5-heptadecanoic acid) (II), copper trifluoromethanesulfonate (II), cuprous tetra(acetonitrile)hexafluorophosphate (I), and cuprous tetra(acetonitrile)tetrafluoroborate (I).

[0076] By adding copper salts and ligands or salts separately to the reaction mixture, suitable copper complexes can also be generated in situ in the reaction mixture. The ligands or salts are, for example, ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, 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-di(2-pyridyl)pyridine, 2-pyridinecarboxylic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-o-diazaphenanthroline, 3,4,7,8-tetramethyl-1,10-o-diazaphenanthroline. Phenanthrene, 2,9-dimethyl-1,10-o-diaphenanthrene, 4,7-dimethoxy-1,10-o-diaphenanthrene, 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-tetrachlorophenanthrene Methylheptane-3,5-dione, 2-(2,2-dimethylpropionyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropionyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphine, ethylidene bis-(diphenylphosphine), N,N-diethylsalicylic acidamide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid, or 1H-pyrrole-2-carboxylic acid.

[0077] 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).

[0078] 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-butylphosphine tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl, 2-(di-tert-butylphosphine)biphenyl, 2-(dicyclohexylphosphine)-2'-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphine)-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphine-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphine-2,6'-dimethoxybiphenyl, 2-dicyclohexylphosphine-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.

[0079] 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 references therein).

[0080] Some of the methods described in this article can be performed via metal-photo-redox 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., Ir and Ru complexes or organic dyes) and a metal catalyst (e.g., Ni complexes). The reaction can be carried out in the presence of ligands and, if appropriate, under blue or white light irradiation in the presence of a base.

[0081] 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-phenanthroline); Ru(II) photocatalysts, such as Ru(bpy)3Cl2 or Ru(bpy)3(PF6)2; or organic dyes, such as 9-mesityl-10-acrylidine perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazole-9-yl-1,3-benzenedionitrile, 9-fluorenone and 9,10-phenanthrenequinone.

[0082] 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).

[0083] The methods described herein can be carried out at temperatures ranging from -105°C to 250°C, preferably from -78°C to 185°C.

[0084] 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.

[0085] The methods described in this article are typically performed at standard pressure. However, they can also be performed at increased or decreased pressure.

[0086] The methods described herein can optionally be performed under microwave radiation at standard pressure or elevated pressure.

[0087] In the methods described herein, the starting materials are typically used in approximately equimolar amounts. However, it is also possible to use one of the starting materials in a relatively large excess.

[0088] Methods for preparing compounds of formula (I) Method A Compounds of formula (Ia), wherein R 3 R 4 R 5 R 6 R 7 R 8 L and Q, as defined above, can be prepared in the following ways: When W is hydrogen, the compound (R) of formula (4) is optionally treated in the presence of a base using a dehydrating agent. 3 R 4 R 5 R 6 R 7 R 8 L and Q (as defined above) are used to directly obtain 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), as shown in Scheme 1.

[0089] Option 1: Method A – Synthetic compound of formula (Ia) The compound of formula (Ia) can optionally be obtained by treating the compound of formula (4) in the presence of a base using a dehydrating agent (e.g., POCl3, P2O5, or trifluoromethanesulfonic anhydride). Such methods for forming the oxadiazine ring are known and described in J. Med. Chem. 2017, 60, 2383-2400 and patents WO2020127780, WO2021245083, WO2021249995, and WO2021245087. The reaction can be carried out in any conventional inert organic solvent. Preferred are optionally halogenated aliphatic, alicyclic, or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, or decalin; 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.

[0090] 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; Fifth Edition; 2014; 895-1194). For example, the tert-butoxycarbonyl group can be removed in an acidic medium such as hydrochloric acid or trifluoroacetic acid.

[0091] The compound of formula (4) can be obtained by the following methods: - Compound of formula (1) (where R) 7 R 8 Q is as defined above, and U 1 (where R is a hydroxyl, C1-C6-alkoxy, or halogen) and an amine of formula (2) (where R is a hydroxyl, C1-C6-alkoxy, or halogen) 3 R 4 R 5 R 6As defined above, L and W are hydrogen or amino protecting groups, such as tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl) or one of their salts, to give the compound of formula (3); -Remove the phthalimide group from compound (3) to provide a compound of formula (4), wherein R 3 R 4 R 5 R 6 R 7 R 8 L and Q are defined above, and W is hydrogen.

[0092] The reaction conditions for removing the phthalimide group are well known and reported in the literature (Greene's Protective Groups in organic Synthesis; Peter GM Wuts; Wiley; 5th ed.; 2014; 1012-1014).

[0093] The compounds of formula (1) can be prepared by one or more methods described herein (see method F), or by the methods described in patents WO2023 / 089049 and WO2024 / 132901.

[0094] The amine in formula (2) can be prepared by the methods described in patents WO2020 / 127780, WO20212 / 45083, WO20212 / 49995 and WO20212 / 45087.

[0095] Among them U 1Compounds 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)phosphine 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-methylmorpholinium chloride hydrate, bromotripyrrolidinyl phosphonium hexafluorophosphate, or propylphosphonic anhydride (T3P).

[0096] Among them U 1 A halogenated compound of formula (1) can react with an amine of formula (2) by a well-known method in the presence of an acid scavenger. Suitable acid scavengers include any inorganic and organic bases commonly used for such reactions as described herein. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic bases are preferred.

[0097] Among them U 1 Compounds of formula (1) that are C1-C6-alkoxy can be reacted with an excess of an amine of formula (2), optionally in the presence of a Lewis acid such as trimethylaluminum.

[0098] Method B Compounds of formula (Ia), wherein R 3 R 4 R 5 R 6 R 7 R 8 As defined above, L and Q can be obtained by making compound (7) of formula (where R) 3 R 4 R 5 R 6 R 7 R 8 The compound of formula (8) (where Q is as defined above) is prepared by reacting with a base (e.g., an organic or inorganic base) and optionally in the presence of a suitable copper salt or complex, as shown in Scheme 2.

[0099] Option 2: Method B – Compound of formula (Ia) The compound of formula (7) can be prepared under the same conditions as described in method A by the following steps: first, the compound of formula (5) is reacted with one of the amines or salts of formula (2) to obtain the compound of formula (6a), where R in formula (5) 7 R 8 And X as defined above, and U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. In equation (2), 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. In equation (6a), R 3 R 4 R 5 R 6 R 7 R 8 L, X, and W are as defined above. Then the phthalimide group of compound (6a) is removed to obtain compound (6b), in which R 3 R 4 R 5 R 6 R 7 R 8 L, X, and W are as defined above, and When W is hydrogen, the compound of formula (6b) can be directly obtained by treating it with a dehydrating agent in the presence of a base. 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, and then a deprotection step is performed to obtain the compound of formula (7).

[0100] The reaction of compound (7) with compound (8) can be carried out in the presence of a transition metal catalyst (such as a copper salt or complex) and, if appropriate, in the presence of a ligand as described herein.

[0101] The compound of formula (5) is commercially available or can be prepared by hydrolyzing compound (18).

[0102] The compound of formula (8) is commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to well-known methods.

[0103] Method C The compound of formula (Ia) can be prepared by adding a reducing agent to the compound of formula (12) under acidic conditions, wherein R 3 R 4 R 5 R 6 R 7 R 8 L and Q are defined as above, thus obtaining a compound of formula (Ia), as shown in Scheme 3.

[0104] Option 3: Method C – Synthesizing compounds of formula (Ia). The compound of formula (12) can be cyclized under acidic conditions in the presence of a reducing agent (e.g., sodium cyanoborohydride) to give the compound of formula (Ia). The reaction conditions for forming the oxadiazine ring using this method are known and described in the literature (Heterocycles 2016, 92, 2166-2200, WO2020 / 127780, WO2021 / 245083, WO2021 / 249995 and WO2021 / 245087).

[0105] The compound of formula (12) can be made by making the compound of formula (10) (where R) 7 R 8 And Q as defined above) and the compound of formula (11) (where R) 3 R 4 R 6 It is obtained by reacting L (as defined above) in the presence of a base. Suitable bases may be alkali metal hydrides (e.g., sodium hydride), alkali metal carbonates (e.g., potassium carbonate), alkali metal hydroxides (e.g., potassium hydroxide), or phosphazene bases (e.g., BEMP), as described in the literature (Heterocycles 2016, 92, 2166-2200).

[0106] The compound of formula (10) can be made by making the compound of formula (9) (where R) 7 R 8 Q is obtained by reacting it with a hydroxylamine or a salt thereof (as defined above). The reaction conditions for carrying out such a 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. Where R 7 R 8 And X as defined above.

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

[0109] The compounds of formula (18) are either commercially available or can be prepared by the methods described in the literature (WO2020 / 106751 and WO98 / 35967).

[0110] Method D Compounds of formula (Ia), wherein R 3 R 4 R 5 R 6 R 7 R 8 L and Q, as defined above, can be prepared by a method including the following steps, as shown in Scheme 4: - Make the compound of formula (1) (where R) 7 R 8 R and Q (as defined above) are reacted with an amine or a salt thereof of formula (13) under conditions similar to those described in method A to obtain a compound of formula (14), wherein R in formula (13) 3 R 4 R 5 R 6 And L is as defined above, and E 1 It is a hydroxyl group or a halogen. In equation (14), R 3 R 4 R 5 R 6 R 7 R 8 E 1 L and Q are as defined above, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. - The compound of formula (14) is treated with a dehydrating agent, followed by treatment with hydroxylamine, to form the compound of formula (15), wherein R 3 R 4 R 5 R 6R 7 R 8 E 1 L, Q, and W are as defined above. - When E 1 When the hydroxyl group is used, the compound of formula (15) is converted into the compound of formula (Ia) using the Mitsunobu 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.

[0111] Option 4: Method D – Compound of formula (Ia) Steps 2 and 3 of method D can be carried out using reaction conditions similar to those described in method E.

[0112] 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 One of the compounds of the halogen (or its salt) can be obtained from the corresponding amino alcohol by known methods.

[0113] Method E Compounds of formula (Ia), wherein R 3 R 4 R 5 R 6 R 7 R 8 L and Q, as defined above, can be prepared by a method including the following steps, as shown in Scheme 5: - React the compound of formula (5) with an amine of formula (13) or a salt thereof under conditions similar to those described in method A to obtain the compound of formula (16), wherein R in formula (5) 7 R 8 As defined above, and X is a halogen, preferably chlorine. U 1 It is a hydroxyl, halogen, or C1-C6-alkoxy group. In equation (13), 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. In equation (16), R 3 R 4 R 5 R 6 R 7 R 8 E 1 L and X are as defined above, and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. - The compound of formula (16) was treated with a dehydrating agent, followed by treatment with a hydroxylamine, to obtain the compound of formula (17), wherein R 3 R 4 R 5 R 6 R 7 R 8 E 1 L and X are as defined above. - When E 1 When the hydroxyl group is used, the compound of formula (17) is converted into the compound of formula (7) using the Mitsunobu 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 R 8 The compound of formula (8) (where Q is as defined above) is reacted with a base (e.g., an organic or inorganic base) and optionally in the presence of a suitable copper salt or complex to give the compound of formula (Ia).

[0114] Option 5: Compounds of method E – synthetic formula (Ia) Methods for preparing compounds of formula (1) The compound of formula (1) described herein can be obtained directly by performing the method F described below, or by converting or derivatizing another compound of formula (1) prepared according to the method described herein or the method described in WO2023 / 089049 and WO2024 / 132901.

[0115] Method F Compound of formula (1) (where R) 7 and R8 As defined above, it can be prepared by reacting the compound of formula (5) with the reagent of formula (8) (where Q is as defined above) in the presence of a base, as shown in Scheme 6, where R in formula (5) 7 and R 8 As defined above, and X is a halogen. U 1 It is a C1-C6-alkoxy group.

[0116] Scheme 6: Preparation of method F – compound (1) Method F can be carried out in the presence of a suitable transition metal catalyst salt or complex, and when appropriate, in the presence of a ligand.

[0117] The compound of formula (5) is commercially available or can be prepared by hydrolyzing compound (18).

[0118] The compound of formula (8) is commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to well-known methods.

[0119] Among them U 1 Compounds of formula (1) with C1-C6-alkoxy groups can be converted to U by well-known functional group interconversion methods. 1 Compounds of formula (1) with hydroxyl groups, for example by hydrolyzing the ester group in THF / water with LiOH.

[0120] Among them U 1 Compounds of formula (1) with a hydroxyl group can be converted to U by well-known methods in the presence of a halogenating agent. 1 The halogenated compound is of formula (1). Suitable halogenating agents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, or thionyl chloride.

[0121] Method G Compounds of formula (1-b), wherein R 8 And Q is as defined above, and R 8a It is chlorine. U 1 It is a C1-C6-alkoxy group. The corresponding compound of formula (1-c) can be converted by known methods through one or more steps shown in Scheme 7, wherein R 7 U 1 And Q is as defined above, and R 8b It is a methyl group.

[0122] Scheme 7: Preparation of compounds (1-c) and (1-d) by method G Non-restrictive examples of the transformation can be made according to the description provided in WO2023 / 089049.

[0123] intermediate This invention also relates to compounds of formulas (3) and (4): , in R 3 R 4 R 5 L, R 6 R 7 R 8 And Q is as defined in equation (I), W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0124] For R given by equation (I) 3 R 4 R 5 L, R 6 R 7 R 8 The definitions of preferred, more preferred, even more preferred and most preferred for Q can be applied by reference.

[0125] The present invention also relates to compounds of formula (7), in R 3 R 4 R 5 L, R 6 R 7 and R 8 As defined in equation (I), X is a halogen, preferably fluorine, chlorine, or bromine.

[0126] For R given by equation (I) 3 R 4 R 5 L, R 6 R 7 and R 8 The definitions of preferred, more preferred, even more preferred and most preferred can be referred to and applied.

[0127] This invention also relates to compounds of formula (10): in R 7 and R8 As defined in equation (I).

[0128] For R given by equation (I) 7 and R 8 The definitions of preferred, more preferred, even more preferred and most preferred can be referred to and applied.

[0129] This invention also relates to compounds of formula (12): in R 3 R 4 L, R 6 R 7 R 8 And Q is as defined in equation (I), For R given by equation (I) 3 R 4 L, R 6 R 7 R 8 The definitions of preferred, more preferred, even more preferred and most preferred for Q can be applied by reference.

[0130] The present invention also relates to compounds of formulas (14) and (15): in R 3 R 4 R 5 L, R 6 R 7 R 8 And Q is as defined in equation (I), X is a halogen, preferably fluorine, chlorine, or bromine. E 1 It is a hydroxyl or halogen, preferably hydroxyl, chlorine or bromine. E 2 It is a hydroxyl group. and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0131] For R given by equation (I) 3 R 4 R 5 L, R 6 R 7 R 8 The definitions of preferred, more preferred, even more preferred and most preferred for Q can be applied by reference.

[0132] The present invention also relates to compounds of formulas (16) and (17): in R 3 R 4 R 5 L, R 6 R 7 and R 8 As defined in equation (I), X is a halogen, preferably fluorine, chlorine, or bromine. E 1 It is a hydroxyl or halogen, preferably hydroxyl, chlorine or bromine. E 2 It is a hydroxyl group. and W can be hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0133] For R given by equation (I) 3 R 4 R 5 L, R 6 R 7 and R 8 The definitions of preferred, more preferred, even more preferred and most preferred can be referred to and applied.

[0134] 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 environment.

[0135] The composition comprises at least one compound of formula (I) and at least one suitable agricultural adjuvant, such as a carrier and / or a surfactant.

[0136] The carrier is a generally inert solid or liquid, natural or synthetic, organic or inorganic substance. The carrier typically facilitates the application of the compound to, for example, plants, plant parts, or seeds. Examples of suitable solid carriers 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. Examples of suitable liquid carriers include, but are not limited to: water, organic solvents, and combinations thereof. Examples of suitable solvents 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 or polyols (which may optionally be substituted, etherified and / or esterified, e.g., 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), vegetable oils or oils derived from 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.

[0137] The preferred solid carrier is selected from clay, talc and silica.

[0138] The preferred liquid carrier is selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams and carbonates.

[0139] The amount of carrier is typically 1 to 99.99%, preferably 5 to 99.9%, more preferably 10 to 99.5%, and most preferably 20 to 99%, based on the weight of the composition.

[0140] The liquid carrier is typically present at 20% to 99%, such as 30% to 80%, based on the weight of the composition.

[0141] The solid carrier is typically present at 0 to 50%, preferably 5 to 45%, such as 10 to 30%, based on the weight of the composition.

[0142] If the composition contains two or more carriers, the above range refers to the total amount of carriers.

[0143] The surfactant may 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 of these surfactants. 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 sulfate waste, and methylcellulose. Any salt mentioned in this paragraph preferably refers to its respective alkali metal salt, alkaline earth metal salt, or ammonium salt.

[0144] 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.

[0145] The amount of surfactant is typically 5 to 40%, for example 10 to 20%, based on the weight of the composition.

[0146] Other examples of suitable additives 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 sodium cellulose acetate), 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. dichlorobenzene 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.

[0147] The selection of adjuvants is related to the intended manner of application and / or the physical properties of the compound of formula (I). 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.

[0148] The compositions of the present invention can be provided to the end user in the form of a ready-to-use formulation, i.e., a composition that can be applied directly to plants or seeds using suitable equipment such as a sprayer or powderer. Alternatively, the compositions can be provided to the end user in the form of a concentrate, which must be diluted before use, preferably with water.

[0149] 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 (e.g., disclosed above).

[0150] The composition comprises a fungicide-effective amount of a compound of formula (I). The term "effective amount" means an amount sufficient to control harmful fungi on cultivated plants or in the protected material 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, compositions according to the 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 invention. In this case, the above ranges refer to the total amount of the compounds of the invention.

[0151] The compositions of the present invention can be in any conventional compositional form, such as 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) can exist in suspended, emulsified, or dissolved forms. Examples of particularly suitable compositional forms 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 dusts (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 compositional types are defined by the Food and Agriculture Organization of the United Nations (FAO). For a summary, see "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition, May 2008, Croplife International.

[0152] 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.

[0153] Further details regarding examples of composition types and their preparation are given below. If two or more of the compounds of the invention are present, the amounts of the compounds given refer to the total amount of the compounds of the invention. This refers to any other component applicable to the composition if two or more of such components (e.g., wetting agents, binders) are present.

[0154] 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.

[0155] 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 dispersion.

[0156] 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 a fatty acid amide), and, if necessary, add a water-soluble solvent to obtain a total amount of 100% by weight. Dilute with water to obtain an emulsion.

[0157] 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 a corresponding amount of water using an emulsifier to obtain a total of 100% by weight. The resulting composition is a homogeneous emulsion. The emulsion may be further diluted with water before application.

[0158] 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 and 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.

[0159] 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 and 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. The mixture is diluted with water to obtain a stable dispersion of the active substance.

[0160] vi) Water-dispersible granules and water-soluble granules (WG, SG) Finely grind 50-80% by weight of at least one compound of formula (I) and add 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 dispersion or solution of the active substance.

[0161] 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 finely ground and 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 dispersion or solution of the active substance.

[0162] viii) Gel agents (GW, GF) In a stirred ball mill, 5-25% by weight of at least one compound of formula (I) is pulverized and 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 produces a fine suspension of the active substance. Diluting with water yields a stable suspension of the active substance.

[0163] 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 the 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.

[0164] 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 amount is 1-10 wt%, based on the weight of the total CS composition.

[0165] xi) Powdering agents (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 support (e.g., finely dispersed kaolin) to obtain a total amount of 100% by weight.

[0166] 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.

[0167] xiii) Ultra-low volume liquids (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.

[0168] 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.

[0169] Mixtures / Compositions The compounds of formula (I) and the compositions 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, information chemicals, and / or other agriculturally beneficial formulations 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.

[0170] Examples of fungicides that can be mixed with compounds and compositions of formula (I) of the present invention include: 1) Ergosterol biosynthesis inhibitors, 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), propiconazole (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]benzonitrile, (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]benzonitrile, (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]imidazol-4-onitrile, (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]-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-methyliminomethylamide, (1.045) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methyliminomethylamide, (1.046) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methyliminomethylamide, (1.047) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyliminoformamide, (1.048) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methyliminomethylamide, (1.049) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide, (1.050) N'-[5-bromo-6-(2,3-dihydro-1H-indene-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (1.051) N'-{4-[(4,5-dichloro-1,3-thiazolyl-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, (1.052) N'-{5-bromo-2-methyl-6-[(1-propoxypropyl-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.053) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.054) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.055) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.056) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.057) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.058) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methyliminocarboxamide, (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-methylformamidinium.

[0171] 2) Inhibitors of respiratory chain complex 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) furamettapyr, (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), pyraziflumid (2.021), sedaxane (2.022), thifluxamide (aka trifluzamide), 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-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-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalene-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.

[0172] 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), piraclostrobin (3.023), pirametostrobin (3.024), piraoxystrobin (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]methyl propionate, (3.036) (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]methyl propionate, (3.037) {5-[3-(2,4-dimethylphenyl)-1H-pyrazole-1-yl]-2-methylbenzyl}carbamate, (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-indol-1-yl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridin-2-carbonyl)amino]propionate, (3.041) [rac-2-(7-bromo-4-fluoro-indol-1-yl)-1-methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, (3.042)[rac-2-(7-bromoindol-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-carboxamido-2-hydroxybenzamide.

[0173] 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, (4.024)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.

[0174] 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.

[0175] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, (6.002) 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.

[0176] 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.

[0177] 8) Inhibitors of ATP production, such as (8.001) silthiofam.

[0178] 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, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one. 10) Inhibitors of lipid synthesis, 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-pyrazol-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-pyrazol-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-benzodioxon-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-benzodioxon-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.

[0179] 11) Inhibitors of melanin biosynthesis, such as (11.001) tolprocarb and (11.002) tricyclazole.

[0180] 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).

[0181] 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.

[0182] 14) Compounds that can act as uncoupling agents, such as (14.001) fluazinam and (14.002) meptyldinocap.

[0183] 15) Other compounds, such as (15.001) abscisic acid, (15.002) aminopyrifen, (15.003) bethoxazin, (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) methylisothiocyanate, (15.020) mildiomycin, (15.021) nickel dimethyldithiocarbamate, (15.022) nitrothal-isopropyl, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its 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, (15.033) 4-Amino-5-fluoropyrimidin-2-ol (tautomer form: 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) {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate butyl-3-yn-1-yl ester, (15.040) (2Z)-3-amino-2-cyano-3-phenyl acrylate ethyl ester, (15.041) 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) 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-benzoxazetane-heptanetriene, (15.075) N-(2,4-dimethyl-1-phenylpent-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-quinoline)-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-methylpyridazin-4-carboxamide, (15.089) 6-Chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide, (15.090) 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide, (15.091) 6-Chloro-3-(3-chloro-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-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, (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]benzylthiocarboxamide, (15.137) N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.138) 2,2-difluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic acid.

[0184] All named mixed partners 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.

[0185] The compounds and compositions of formula (I) of the present invention can also be combined with one or more biocontrol agents.

[0186] 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.

[0187] 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 parental strain, and the method of obtaining the mutant or variant, wherein the pesticide activity is greater than that expressed by the parental strain. Herein, "parental strain" is defined as the original strain before mutagenesis. To obtain such a mutant, the parental 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 mechanisms of biocontrol agents involve controlling enteric bacteria that cause root rot by 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 they can be given to bacterial species to induce in situ production of the toxin.

[0188] A “variant” is a strain that possesses all the identifying characteristics of the NRRL or ATCC registry number shown herein, and is identifiable as having a genome that hybridizes with the genome of the NRRL or ATCC registry number under highly stringent conditions.

[0189] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stabilized by hydrogen bonding between the bases of nucleotide residues. Hydrogen bonding can occur through Watson-Crick base pairing, Hoogstein binding, or any other sequence-specific mechanism. The complex can comprise two strands forming a double-stranded structure, three or more strands forming a multi-stranded complex, a single self-hybridized strand, or any combination thereof. Hybridization reactions can be performed under different "stringent" conditions. Typically, low-stringent hybridization reactions are performed at approximately 40°C in 10 X SSC or equivalent ionic strength / temperature solutions. Moderate-stringent hybridization is typically performed at approximately 50°C in 6 X SSCs, while high-stringent hybridization reactions are typically performed at approximately 60°C in 1 X SSCs.

[0190] A variant of the NRRL or ATCC registry number shown may also be defined as a strain having a genomic sequence with a sequence identity greater than 85%, more preferably greater than 90%, or even more preferably greater than 95% with the genome of the NRRL or ATCC registry number shown. "Sequence identity" of a polynucleotide or polynucleotide region (or a polypeptide or polypeptide region) with another sequence at a certain percentage (e.g., 80%, 85%, 90%, or 95%) means that, when aligned, that percentage of bases (or amino acids) are identical in the two sequences being compared. This alignment and percentage of homology or sequence identity can be determined using software programs known in the art, such as those described in Current Protocols in Molecular Biology (edited by FM Ausubel et al., 1987).

[0191] NRRL is an abbreviation for Agricultural Research Service Culture Collection. Based on the international recognition of the preservation of microorganisms for patent proceedings under the Budapest Treaty, this institution is an international collection for the preservation of microbial strains. Its address is: National Center for Agricultural Utilization Research, Agricultural Research service, US Department of Agriculture, 1815 North University Street, Peroira, Illinois 61604 USA.

[0192] ATCC is an abbreviation for American Type Culture Collection. Based on the international recognition of the preservation of microorganisms for patent proceedings under the Budapest Treaty, this organization is an international depository for the purpose of preserving strains of microorganisms. Its address is ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110USA.

[0193] Examples of biocontrol agents that can be combined with compounds and compositions of formula (I) of the present invention are as follows: (A) Antibacterial agents selected from the following: (A1) Bacteria, such as (A1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer CropScience LP, US under SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661, US Patent No. 6,060,051); (A1.2) Bacillus sp., particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. under DOUBLE NICKEL®), Registry No. FERM BP-8234, US Patent No. 7,094,592; (A1.3) Bacillus pumilus (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24, DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA 70127-5)); (A1.5) Paenibacillus sp. strains, NRRL B-50972 or NRRLB-67129, WO 2016 / 154297; (A1.6) Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS®... (A1.7) Bacillus mojavensis strain R3B (registration number NCAIM (P)B001389) (WO 2013 / 034938) from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.8) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.9) Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.); (A1.10) Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); (A1.10) Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); (A1.10) Pseudomonas proradix.11) Pantoea agglomerans, particularly strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIMEBIOLOGICAL™ FD BIOPESTICIDE); and (A2) Fungi, such as (A2.1) *Aureobasidium pullulans*, particularly budding spores of strain DSM14940, strain DSM14941, or a mixture of budding spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH); (A2.2) *Pseudozymaaphidis* (e.g., as disclosed by Yissum Research Development Company of the Hebrew University of Jerusalem in WO2011 / 151819); (A2.3) *Saccharomyces cerevisiae*, particularly strains CNCM I-3936, CNCM I-3937, CNCM I-3938 or CNCM I-3939 from Lesaffre et Compagnie, FR (WO2011 / 151819). 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 part of the Cartissa product, EPA registration number 71840-19); (B1.5) Bacillus amyloliquefaciens, particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as Double Nickel™, registration number FERM BP-8234, US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biofungicide under registration numbers 4764, 5454, 5096, and 5277); (B1.7) Bacillus subtilis strain MBI 600 (available from BASF SE as 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 subtilis amyloliquefaciens strain FZB24, accession number DSM 10271 (available from Novozymes under TAEGRO® or TAEGRO® ECO (EPA accession number 70127-5)); (B1.10) Bacillus mycoides, isolate J, accession number B-30890 (available from Certis USALLC (a subsidiary of Mitsui & Co.) under BMJ TGAI® or WG and LifeGard). TM(obtained); (B1.11) Bacillus licheniformis, particularly strain SB3086, ATCC 55406, WO 2003 / 000051 (available from Novozymes with ECOGUARD® biofungicide and GREEN RELEAF). TM(B1.12) Bacillus strain, NRRL B-50972 or NRRL B-67129, WO 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814, (available from BASF SE in VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA); (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 No. B-50768; WO 2014 / 028521) (from Marrone Bio Innovations' STARGUS®); (B1.16) Bacillus amyloliquefaciens strain FZB42, Registry No. DSM 23117 (available from ABiTEP, DE as RHIZOVITAL®); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC's QUARTZO® (WG) and PRESENCE® (WP)); (B1.18) Bacillus mohaiwei strain R3B (accession number NCAIM (P)B001389) (WO 2013 / 034938) from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.19) Paenibacillus polymyxa ssp. plantarum from BASF SE (WO 2016 / 020371); (B1.20) Paenibacillus epiphyticus from BASF SE (WO 2016 / 020371); (B.1.21) *Pseudomonas chlororaphis* strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO® from AgBiome Innovations, US); (B1.22) *Pseudomonas chlororaphis*, particularly strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® from Bioagri and Koppert); (B1.23) *Streptomyces lydicus* strain WYEC108 (also known as *Streptomyces lydicus* strain WYCD108US) (from Novozymes' ACTINO-IRON® and ACTINOVATE®); (B1.24) Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA); (B1.25) Agrobacterium radiobacter strain K1026 (e.g., NOGALL from BASF SE). TM (B1.26) Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys); (B1.27) Bacillus subtilis IAB / BS03 (AVIV from STK Bio-Ag Technologies) TM (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan, as BIOBAC® WP, registered in Taiwan as biofungicides under registration numbers 4764, 5454, 5096, and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREENTM from the University of Pretoria); (B1.30) Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces griseoviridis) (Galbus) strain K61 (accession number DSM7206) (from Verdera's MYCOSTOP®; from BioWorks' PREFENCE®; see Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN® A506 from NuFarm); and (B2) Fungi, such as: (B2.1) *Coniothyrium minitans*, especially strain CON / M / 91-8 (accession number DSM-9660; e.g., Contans® from Bayer CropScience Biologics GmbH); (B2.2) *Metschnikowia fructicola*, especially strain NRRL Y-30752; (B2.3) *Microsphaeropsis ochracea*; (B2.5) *Trichoderma atroviride*, especially strain SC1 (accession numbers CBS 122089, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol), or strain LU132 (e.g., Sentinel from Agrim Technologies Limited); (B2.6) Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from SimbioseAgro); (B2.14) Gliocladium roseum (also known as Clonostachys rosea f. rosea), particularly strain 321U from Adjuvants Plus, such as 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) *Talaromyces flavus*, strain V117b; (B2.36) *Trichoderma viride*, especially strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); (B2.37) *Trichoderma asperellum*, especially strain SKT-1, accession 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; (B2.38) *Trichoderma purpureus*, strain CNCM I-1237 (e.g., from Agrauxine, FR Esquive® WP); (B2.39) Trichoderma viride, strain V08 / 002387; (B2.40) Trichoderma viride, strain NMI V08 / 002388; (B2.41) Trichoderma viride, strain NMI V08 / 002389; (B2.42) Trichoderma viride, strain NMI 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 (B2.47) *Trichoderma harzianum*; (B2.48) *Trichoderma harzianum* T39 (e.g., Trichodex® from Makhteshim, US); (B2.49) *Trichoderma harzianum*, particularly 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 virens* (also known as *Gliocladium virens*), particularly strain GL-21 (e.g., *SoilGard* from Certis, US); (B2.53) *Trichoderma virens*, strain TV1 (e.g., *Trianum-P* from Koppert); (B2.54) *Ampelomyces quisqualis*, particularly strain AQ 10 (e.g., *AQ 10®* from IntrachemBio Italia); (B2.56) *Bratifying pupae*, particularly budding spores of strain DSM14940; (B2.57) *Bratifying pupae*, particularly budding spores of strain DSM 14941; (B2.58) *Bratifying pupae*, particularly a mixture of budding spores of strains DSM14940 and DSM 14941 (e.g., from bio-ferm, (B2.64) *Cladosporium cladosporioides*, strain H39, registry number CBS122244, US 2010 / 0291039 (provided by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) *Gliocladium catenulatum* (synonym: *Clonostachys rosea* f. *catenulate*) strain J1446 (e.g., *Prestop®* provided by Lallemand); (B2.70) conidia of *Lecanicillium lecanii* (formerly known as *Verticillium lecanii*) strain KV01 (e.g., *Vertalec®* provided by Koppert / Arysta); (B2.71) *Penicillium* (B2.72) *Pichia anomala*, 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 galbana*, strain SKT-3 (FERM P-17021), Japanese Patent Publication No. 11-253151 A; (B2.78) *Trichoderma gamsii* (formerly *T. viride*), 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 as T-Gro® 7456); (B2.80) *Trichoderma polysporum*, strain IMI 206039 (e.g., *Binab TF WP* provided by BINAB Bio-Innovation AB, Sweden); (B2.81) *Trichoderma* (B2.83) *Stroma stromaticum*, accession number Ts3550 (e.g., *Tricovab* from CEPLAC, Brazil); (B2.84) *Ulocladium oudemansii* strain U3, accession number NM 99 / 06216 (e.g., *BOTRY-ZEN®* from Botry-Zen Ltd, New Zealand and *BOTRYSTOP®* from BioWorks, Inc.); (B2.85) *Verticillium albo-atrum* (formerly *Verticillium dahliae*), accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., *DUTCH TRIG®* from Tree Care Innovations); (B2.86) *Verticillium chlamydosporium*; (B2.87) *Trichoderma echinosporum* strain ICC. A mixture of Trichoderma 012 (also known as Trichoderma harzianum ICC012) (accession number CABI CC IMI 392716) and Trichoderma geysii strain (formerly Trichoderma viride) strain ICC 080 (accession number IMI 392151) (e.g., BIO-TAM from Isagro USA, Inc.). TM(B2.88) BIODERMA® (provided by Agrobiosolde Mexico, SA de CV); (B2.89) Trichoderma asperelloides JM41R (registration number NRRL B-50759) (from BASF SE's TRICHO PLUS®); (B2.89) Aspergillus flavus strain NRRL 21882 (from Syngenta / ChemChina's product called AFLA-GUARD®); (B2.90) Chaetomium cupreum (registration number CABI 353812) (e.g., BIOKUPRUM provided by AgriLife). TM(B2.91) Saccharomyces cerevisiae, particularly strain LASO2 (from Agro-Levures et Dérivés), cell walls of strain LAS117 (from CEREVISANE® of Lesaffre; ROMEO® of BASF SE), strains CNCM I-3936, CNCM I-3937, CNCM I-3938, CNCM I-3939 (WO 2010 / 086790) from Lesaffre et Compagnie, FR; (B2.92) Trichoderma viride strain G-41, formerly known as green broom mold (accession number ATCC20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US); (B2.93) Trichoderma hamatum, accession number ATCC 28012; (B2.94) Powdery mildew strain AQ10, accession number CNCM I-807 (e.g., AQ 10® from IntrachemBio Italia); (B2.95) Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment); (B2.96) Penicillium steckii from BASF SE (DSM 27859; WO 2015 / 067800); (B2.97) Chaetomium globosum (available from Rivale at RIVADIOM®); (B2.98) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) See *Dilophosphora alopecuri* (available from TWIST FUNGUS®); (B2.101) *Fusarium oxysporum*, strain Fo47 (available from Natural Plant Protection at FUSACLEAN®); (B2.102) *Pseudozyma flocculosa*, strain PF-A22 UL (available from Plant Products Co., CA at SPORODEX® L); (B2.103) *Trichoderma galbana* (formerly *Trichoderma viride*), strain ICC 080 (IMI CC 392151 CABI) (available from AGROBIOSOL DE MEXICO, SA DE CV under BIODERMA®); (B2.104) *Trichoderma fertile* (e.g., BASF product TrichoPlus); (B2.105) *Muscodor roseus*, particularly strain A3-5 (registration number NRRL 30548); (B2.106) *Simplicillium lanosoniveum*. Biocontrol agents that can be combined with the compound compositions of the present invention and have the effect of improving plant growth and / or plant health include: (C1) Bacteria selected from the following: *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 with SERENADE® OPTI or SERENADE® ASO); *Bacillus subtilis*, particularly strain AQ30002 (NRRL No. 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); *Sinorhizobium* of alfalfa. Bacillus meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer Crop Science); Bacillus subtilis strain BU1814 (available from BASF SE under TEQUALIS®); Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection); 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 members EE128 (NRRL No. B-50917), 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 as QUIKROOTS®); 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, particularly strain FZB42 (e.g., RHIZOVITAL® from ABiTEP, DE); Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC under QUARTZO® (WG) or PRESENCE® (WP)); Bacillus cereus, particularly strain BP01 (ATCC 55675; e.g., MEPICHLOR® from ArystaLifescience, US); Bacillus subtilis, particularly strain MBI 600 (e.g., SUBTILEX® from BASF SE); slow-growing soybean rhizobium (Bradyrhizobium japonicum) (e.g., OPTIMIZE® from Novozymes); Mesorhizobium cicer (e.g., NODULATOR from BASF SE); pea rhizobium *Rhizobium* var. *bacco* (*Rhizobium*). * *Lactobacillus* biovar. viciae (e.g., NODULATOR from BASF SE); *Delftia acidovorans*, especially strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds); *Lactobacillus* sp. (e.g., LACTOPLANT® from LactoPAFI); *Bacillus polymyxa*, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.); *Pseudomonas proradix* (e.g., PRORADIX® from Sourcon Padena); *Azospirillum brasilense* (e.g., VIGOR® from KALO, Inc.); *Azospirillum lipoferum* (e.g., VERTEX-IF from TerraMax, Inc.). TMA mixture of *Azotobacter vinelandii* and *Clostridium pasteurianum* (available from Agrinos via INVIGORATE®); *Pseudomonas aeruginosa*, particularly strain PN1; *Rhizobium leguminosarum*, particularly the broad bean biovar strain Z25 (accession number CECT 4585); *Azorhizobium caulinodans*, particularly strain ZB-SK-5; *Azotobacter chroococcum*, particularly strain H23; *Azotobacter vinelandii*, particularly strain ATCC12837; *Bacillus siamensis*, particularly strain KCTC 13613T; *Bacillus tekira*. tequilensis), especially strain NII-0943; Serratia marcescens, especially strain SRM (accession number MTCC 8708); Thiobacillus sp. (e.g., CROPAID® from Cropaid LtdUK); and (C2) Selected fungi from the following: *Purpureocillium lilacinum* (formerly known as *Paecilomyces lilacinus*) strain 251 (AGAL 89 / 030550; e.g., BioAct from BayerCropScience Biologics GmbH); *Penicillium bilaii* strain ATCC22348 (e.g., JumpStart® from Acceleron BioAg); *Demodex flavum* strain V117b; *Trichoderma viride* strain CNCM I-1237 (e.g., Esquive® WP from Agrauxine, FR); *Trichoderma viride* 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 echinosporum strain kd (e.g., T-Gro from Andermatt Biocontrol); Trichoderma echinosporum strain Eco-T (Plant Health Products, ZA); Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria strain AARC-0255 (e.g., DiTera™ from Valent Biosciences); Penicillium baicalensis strain ATCC ATCC20851; Pythium oligandrum strain M1 (ATCC 38472; e.g., from Bioprepraty, Polyversum (CZ); Trichoderma viride strain GL-21 (e.g., SoilGard® from Certis, USA); Verticillium chrysogenum (formerly Verticillium dahliae) strain WCS850 (CBS 276).92; for example, Dutch Trig from Tree CareInnovations); 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 (e.g., contained in Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba (e.g., contained in Myco-Sol from Helena Chemical Company); and Trichoderma viride strain GI-3; Selected from the following insecticidal biocontrol agents: (D1) Selected from the following bacteria: Bacillus thuringiensis subsp. aizawai, particularly strain ABTS-1857 (SD-1372; e.g., XENTARI® from Valent BioSciences); Bacillus mycosis fungi isolate J. (e.g., BmJ from Certis USA LLC (a subsidiary of Mitsui & Co.); Bacillus sphaericus, particularly serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US); Bacillus thuringiensis subsp. kurstaki strain BMP from Becker Microbial Products, IL. 123; Bacillus thuringiensis subsp. niger, particularly serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US); Bacillus thuringiensis subsp. Kurstak strain HD-1 (e.g., DIPEL® ES from Valent BioSciences, US); Bacillus thuringiensis subsp. Kurstak strain BMP 123 from Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products, IL); Burkholderia spp., particularly Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (accession number NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; e.g., MBI-206 TGAI and ZELTO® from Marrone Bio Innovations); active purple bacteria (Chromobacterium subtsugae), particularly strain PRAA4-1T (MBI-203; e.g., GRANDEVO® from Marrone Bio Innovations); milky white pathogenic bacteria (Paenibacillus popilliae) (formerly Bacillus popilliae; e.g., from St.MILKY SPORE POWDER from Gabriel Laboratories. TM and Milky Spore Granular TM Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC® from Valent BioSciences, US); Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g., NOVODOR® FC from BioFa DE); Bacillus thuringiensis var. japonensis strain Buibui; Bacillus thuringiensis var. kurstaki 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 var. Colmeri (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory); Bacillus thuringiensis subspecies GC-91; Serratia entomophila (e.g., INVADE® from Wrightson Seeds); Serratia mucilaginosa, especially strain SRM (accession number MTCC 8708); and Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate); and (D2) Selected fungi from the following: Isaria fumosorosea (formerly Paecilomyces fumosoroseus) strain apopka 97; Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia); Beauveria bassiana strain GHA (accession number ATCC74250; e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation); Zoophtora radicans; Metarhizium rodersii 15013-1 (deposited with NRRL accession number 67073), Metarhizium rodersii 23013-3 (deposited with NRRL accession number 67075), and Metarhizium spp. anisopliae) 3213-1 (deposited under NRRL accession 67074) (WO 2017 / 066094; Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (accession number DSM 24665). Among these, Apopka 97 is particularly preferred; (E) Selected from the following viruses: Adoxophyes orana (summerfruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nucleopolyhedrovirus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodopterafrugiperda (fall armyworm) mNPV, and Spodoptera littoralis (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 plant health by virtue of their specific properties. Examples include: *Agrobacterium* spp., *Azospirillum* spp., *Azotobacters* spp., *Bradyrhizobium* spp., *Burkholderia* spp., especially *Burkholderia cepacia* (formerly *Pseudomonas cepacia*)), *Gigaspora* spp. or *Gigaspora monosporum*, *Glomus* spp., *Laccaria* spp., *Lactobacillus buchneri*, *Paraglomus* spp., *Pisolithus tinctorus*, and *Pseudomonas* spp. *Rhizobium* spp., especially *Rhizobium trifolii*, *Rhizopogon* spp., *Scleroderma* spp., *Suillus* spp., and *Streptomyces* spp.; and (G) Plant extracts and microbial products (including proteins and secondary metabolites) that can be used as biocontrol agents, such as garlic (Allium sativum), wormwood (Artemisia absinthium), azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, and Quassia. The following are listed as active ingredients: *Amara*, *Quercus*, *Quillaja*, *Regalia*, "Requiem™ Insecticide", rotenone, ryania / ryanodine, *Symphytum officinale*, *Tanacetum vulgare*, thymol, Triact 70, TriCon, *Tropaeulum majus*, *Urtica dioica*, Veratrin, *Viscum album*, extracts of the Brassicaceae family (especially rapeseed powder or mustard powder), and bioactive insecticides / miticides obtained from olive oil, particularly unsaturated fatty acids / carboxylic acids with a carbon chain length of C16-C20, for example, contained in products under the trade name FLiPPER®.

[0194] 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.

[0195] The terms “insecticide” and “insecticidal” 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” encompasses all organisms in the class Insecta.

[0196] "Nematicide" and "nematicidal" refer to substances that increase the mortality rate of nematodes or inhibit their growth rate. Generally, the term "nematode" encompasses the egg, larva, juvenile, and mature forms of the organism.

[0197] "Acaricide" and "acaricidal" refer to substances that increase the mortality rate of ectoparasites belonging to the class Arachnida and subclass Acari, or inhibit their growth rate.

[0198] 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, didicophos, dimethoate imethoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, 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.

[0199] (2) GABA-gated chloride channel blockers, such as cyclopentadiene-organochlorines, such as chlordane and endosulfan, or fiproles, such as ethiprole and fipronil.

[0200] (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.

[0201] (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.

[0202] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosides, such as spintoram and spinosad.

[0203] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0204] (7) Juvenile hormone analogues, such as hydroprene, kinoprene and methoprene, or fenoxycarb, or pyriproxyfen.

[0205] (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.

[0206] (9) Chordonal organ modulators, such as pymetrozine or flonicamid.

[0207] (10) Mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin, or etoxazole.

[0208] (11) Insect intestinal membrane microbial disruptors, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and the following Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[0209] (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.

[0210] (13) By uncoupling agents that interrupt the oxidative phosphorylation of the proton gradient, such as chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0211] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0212] (15) Type O chitin biosynthesis inhibitors, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0213] (16) Type I chitin biosynthesis inhibitors, such as buprofezin.

[0214] (17) Molting disruptors (especially for Diptera, i.e., dipteran insects), such as cyromazine.

[0215] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0216] (19) Octopus amine receptor agonists, such as amitraz.

[0217] (20) Inhibitors of electron transport in mitochondrial complex III, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[0218] (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).

[0219] (22) Voltage-dependent sodium channel blockers, such as indoxacarb and metaflumizone.

[0220] (23) Acetyl-CoA carboxylase inhibitors, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0221] (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.

[0222] (25) Inhibitors of electron transport in mitochondrial complex II, such as β-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and carboxanilides, such as pyflubumide.

[0223] (28) Lani base receptor modulators, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[0224] Other active compounds include, for example, afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, chlorpyrifos, cryolite, and cyclaniliprol. e) Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, ε-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexa fon, Fluopyram, Flularaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paicho ngding), pyridalyl, pyrifluquinazon, pyriminostrobin, spirobiclofen, tetramethylfluthrin, tetratraniliprole, tetrachlorantraniliprole, Tigolaner, Tioxazafen, thiofluoximate, triflumezopyrim and iodomethaneiodomethane); and preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), 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 known from 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 known from 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 obtained from 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 obtained from 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-yl ethyl carbonate (as obtained from 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 (from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (from WO2010 / 051926) (CAS1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (as known from CN103232431) (CAS1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo) )-3-thioheterocyclic butyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thioheterocyclic butyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thioheterocyclic butyl)benzamide (from WO (Ascertained from 2013 / 050317 A1)(CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US) 2014 / 0213448 A1 (CAS1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carboxylonitrile (obtained from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, obtained 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)-1H-pyrazole-5-carboxamide (as known from WO 2012 / 034403 A1) (CAS1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (as determined by WO2011 / 085575 A1) (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 determined by CN 101337940) (A) (CAS1108184-52-6); (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide (from CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropane carboxylate (from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indo[1,2-e][1,3,4]oxadiazine-4a(3H)-carbamate (as known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]- -L-Pyranomannose (obtained from US2014 / 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 (obtained from WO 2007040280 A1, WO2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propionamide (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)-1H-pyrazole-5-carboxamide (as obtained from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (as obtained from WO 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4,5]dec-3-en-2-one (as obtained from 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 (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]decane-2,4-dione (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]decane-2,4-dione5] Dec-3-en-4-yl ethyl carbonate (obtained from WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylene]-2,2,2-trifluoroacetamide (obtained from DE 3639877 A1, WO 2012029672 A1) (CAS1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylene]-2,2,2-trifluoroacetamide (obtained from WO 2016005276 A1) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylene]-2,2,2-trifluoroacetamide (CAS 1702305-40-5), 3-oper-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridyl]oxy]-9-azabicyclo[3.3.1]nonane (obtained from WO 2011 / 105506 A1, WO 2016 / 133011 A1) (CAS 1332838-17-1).

[0225] Examples of herbicides that can be mixed with compounds of formula (I) and the compositions of the present invention are as follows: 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. Ester (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, oats Chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-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 ester, 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, detosylpyrazolate (DTP), dicamba, dichlobenil, dichlorprop, dichlorprop, dichlorpropamide rprop-P), diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametrynDimethenamid, 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, ethizozin, 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... The following herbicides are listed: 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, flumethrin, flumethrin 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); halauxifene (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)acetate), 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, mesobenzthiazuron, 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, phenmediphamPicloram, 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 Hifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron-methyl, tribensulfuron, triclopyr, trietazineTrifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron-methyl, triflusulfuron, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline).

[0226] Examples of plant growth regulators are as follows: Activated ester (acibenzolar), activated ester S-methyl (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 N,N-dimethylalkylammonium endothal, ethephon, flumetralin, butyl fluorene, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid acid), maleic hydrazine, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-β-aminopropionic acid, N-phenylphthalamic acid, prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0227] Examples of safeners that can be mixed with compounds of formula (I) and the compositions 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).

[0228] Examples of nitration inhibitors that can be mixed with compounds of formula (I) and compositions 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, pyrazolium glycolate 3,4-dimethyl ester, pyrazolium citrate 3,4-dimethyl ester, pyrazolium lactate 3,4-dimethyl ester, pyrazolium mandelic acid 3,4-dimethyl ester, 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, triazolyl-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-(trichloromethyl)pyridine (nitrapyrin or N-serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, based on neem, linoleic acid, Products containing linolenic acid, methyl p-coumarate, methyl ferulic acid, methyl 3-(4-hydroxyphenyl)propionate, hydroquinone, 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, catechol, benzoquinone, sodium tetraborate, allyl thiourea, chlorate, and zinc sulfate.

[0229] The compounds of formula (I) and the compositions of the present invention can be combined with one or more agriculturally beneficial reagents.

[0230] Examples of beneficial agents in agriculture include: biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulating molecules, biomolecules, soil conditioners, nutrients, and plant nutrient enhancers, 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, brassinolide, salicylates, macro- and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and beneficial microorganisms (e.g., *Rhizobium*, *Sinorhizobium* spp., *Azorhizobium* spp., *Glomus*, *Hymenoscyphous* spp., *Oidiodendron* spp., *Auricularia*, *Pisolithus*). spp.), *Lycoperdon*, *Rhizoctonia*, *Acinetobacter*, *Arthrobacter*, *Arthrobotrys*, *Aspergillus*, *Azospirillum*, *Bacillus*, *Burkholderia*, *Candida*, *Chryseomonas*, *Enterobacter*, *Eupenicillium*, *Exiguobacterium*, *Klebsiella*, *Kluyvera*, *Microbacterium*, *Mucor* spp.), Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas spp., Serratia spp., Stenotrophomonas spp., Streptomyces spp., Streptosporangium spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp.(e.g.), *Xanthomonas* spp., and combinations thereof.

[0231] Methods and uses The compounds of formula (I) and the compositions 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) described in more detail below. More specifically, the compounds of formula (I) and the compositions of the present invention can be used to protect seeds, germinating seeds, newly emerging seedlings, plants, plant parts, fruits, harvested items, and / or the soil in which plants grow from unwanted microorganisms.

[0232] The control or controlling described in this article includes preventative, therapeutic, and eradicative treatments of unwanted microorganisms. Unwanted microorganisms may 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 described in detail below, these plant pathogenic microorganisms are causative agents of broad-spectrum plant diseases.

[0233] More specifically, the compounds of formula (I) and the compositions 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.

[0234] The compounds of formula (I) and the compositions 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 Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[0235] The compounds of formula (I) and the compositions of the present invention can also be used as antiviral agents in crop protection. For example, compounds of formula (I) and compositions of the present invention can have an effect on diseases caused by plant viruses such as tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leaf curl 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 Yellows Virus (Cucumber Yellows Virus), WMV (Watermelon Mosaic Virus), TSWV (Tomato Spotted Wilt Virus), TomRSV (Tomato Ringspot Virus), SCMV (Sugarcanemosaic Virus), SCMV (Rice Dwarf Virus), VBV (Rice Stripe Virus), SCMV (Rice Black-streaked Dwarf Virus), SMoV (Strawberry Mottle Virus), SVBV (Strawberry Vein Banding 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).

[0236] 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) or at least one composition of the present invention to the microorganism and / or its habitat (applied to the plant, plant part, seed, fruit or soil in which the plant grows).

[0237] Specifically, the present invention relates to a method for controlling harmful microorganisms in crop protection and material protection, wherein at least one compound of formula (I) and / or a composition according to the invention are applied to the harmful microorganisms and / or their living environment.

[0238] Harmful microorganisms that can be controlled using this method are described in more detail in the "Pathogens" section below.

[0239] Preferably, the harmful microorganisms are pathogenic oomycetes or plant pathogenic fungi selected from the following genera: *Podosphaera*, *Sphaerotheca*, *Uncinula*, *Gymnosporangium*, *Hemileia*, *Phakopsora*, *Puccinia*, *Uromyces*, *Albugo*, *Bremia*, *Peronospora*, and *Phytophthora*. Species of the genera *Hora*, *Plasmopara*, *Pseudoperonospora*, *Pythium*, *Alternaria*, *Cercospora*, *Cladiosporium*, *Cochliobolus*, *Corynespora*, *Cycloconium*, *Diaporthe*, *Elsinoe*, *Gloeosporium*, and *Small clumps*. Species of the genera *Glomerella*, *Guignardia*, *Leptosphaeria*, *Magnaporthe*, *Microdochium*, *Mycosphaerella*, *Phaeosphaeria*, *Pyrenophora*, *Ramularia*, *Rhynchosporium*, *Septoria*, *Stagonospora*, and *Septoria*. Species of the genera *Typhula*, *Venturia*, *Corticium*, *Fusarium*, *Gaeumannomyces*, *Plasmodiophora*, *Rhizoctonia*, *Sarocladium*, *Sclerotium*, *Tapesia*, *Thielaviopsis*, *Aspergillus*, and *Claviceps*.Species of the genera *Gibberella*, *Monographella*, *Stagnospora*, *Sphacelotheca*, *Tilletia*, *Urocystis*, *Ustilago*, *Monilinia*, *Penicillium*, *Rhizopus*, *Sclerotinia*, *Verticilium*, *Aphanomyces*, *Ascochyta*, *Cladosporium*, *Macrophomina*, *Phoma*, and *Phomopsis*. Species of the genera *Pyricularia*, *Verticillium*, *Nectria*, *Exobasidium*, *Taphrina*, *Esca*, *Ganoderma*, *Helminthosporium*, *Xanthomonas*, *Pseudomonas*, *Erwinia*, *Liberibacter*, *Xyella*, *Ralstonia*, *Dickeya*, *Clavibacter*, *Streptomyces*, and *Colletotrichum*. Gloeosporoidesdematium var. truncatum), Choanephora infundibulifera trispora (Syn.) leaf blight, Dactuliophora glycines leaf spot, Drechslera glycini wilt, Leptosphaerulina trifolii, Phyllosticta sojaecola, Microsphaera diffusa, Pyrenochaeta glycines, Sphaceloma glycinesStemphylium botryosum (allium leaf blight fungus), Calonectria crotalariae (wild lily red blight fungus), Mycoleptodiscus terrestris (root rot fungus), Neocosmospora vasinfecta (infecting vine red blight fungus), and Phialophora gregata (soybean stem brown rot fungus).

[0240] More preferably, the harmful microorganisms are pathogenic oomycetes or plant pathogenic fungi selected from the following genera: Alternaria, Nelumbo, Monotylosporium, Fusarium, and Scyphozoa.

[0241] Most preferably, the harmful microorganisms are pathogenic oomycetes or plant pathogenic fungi selected from the following: Alternaria, Alternaria brassicae, Cynodon dactylus, Erythrophagus monotyphi, Fusarium oxysporum, and Styrax hygrostis.

[0242] Typically, when using compounds of formula (I) and compositions of the present invention in therapeutic or protective methods for controlling plant pathogenic fungi and / or plant pathogenic oomycetes, they are applied to the plant, plant parts, fruits, seeds, or to the soil or substrate in which the plant grows, in an effective and plant-compatible amount. Suitable substrates for cultivating plants include inorganic-based substrates, such as mineral wool, especially asbestos, 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 means an amount sufficient to control or destroy fungi present or readily available in the field without causing any obvious phytotoxic symptoms in the crop. This amount can vary widely depending on the fungi to be controlled, the type of crop, the growth stage of the crop, climatic conditions, and the various compounds or compositions of the present invention used. This amount can be determined through systematic field trials, to the skill of those skilled in the art.

[0243] Plants and plant parts The compounds of formula (I) and the compositions of the present invention can be applied to any plant or plant part.

[0244] Plants refer to all plants and plant populations, including desired and unwanted wild plants or 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 protected or not protected by plant breeders' rights.

[0245] Plant cultivars should be understood as plants that possess novel characteristics ("traits") and have been obtained through conventional breeding, mutagenesis, or recombinant DNA techniques. They can be cultivars, varieties, biotypes, or genotypes.

[0246] Plant parts should be understood to refer to all above-ground and underground parts and organs of a plant, such as buds, leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes. Plant parts also include harvested materials as well as asexual and sexual propagation materials, such as cuttings, tubers, rhizomes, divisions, and seeds.

[0247] Plants that can be treated according to the methods described herein include: cotton, flax, grapevines, fruits, and vegetables, such as species of the Rosaceae family (e.g., 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 sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g., banana trees and banana plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., and Sterculiaceae sp. Species of the following families include: Rutaceae (e.g., lemon, orange, and grapefruit), Solanaceae (e.g., tomato), Liliaceae, Asteraceae (e.g., lettuce), Umbelliferae, Cruciferae, Chenopodiaceae, Cucurbitaceae (e.g., cucumber), Alliaceae (e.g., leeks, onions), and Papilionaceae (e.g., peas); major crops such as Gramineae (e.g., corn, turfgrass, cereals (e.g., wheat, rye, rice, barley, oats, millet, and triticale)), Asteraceae (e.g., sunflower), and Brassicaceae. (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, kohlrabi, radish, as well as rapeseed, mustard greens, horseradish, and watercress), Fabaceae (e.g., green beans, peanuts), Papilionaceae (e.g., soybeans), Solanaceae (e.g., potatoes), Chenopodiaceae (e.g.)(e.g., sugar beets, forage beets, Swiss chard, beetroot); useful and ornamental plants in gardens and forests; and their respective genetically modified varieties.

[0248] 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 or microbial pests (such as nematodes, insects, mites, plant pathogenic fungi, bacteria, viruses and / or viroids).

[0249] 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.

[0250] 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.

[0251] 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.

[0252] Transgenic plants, seed treatment, and integrated lines (event) 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 events, or combinations thereof. For the purposes of this application, a transgenic event is produced by inserting a specific recombinant DNA molecule into a specific location (site) on a plant genome chromosome. 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 or flanking both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, wherein the trait is determined relative to plants lacking such a trait or transgenic event. Specific examples of such advantageous and / or useful traits are better plant growth, vigor, stress tolerance, stand growth capacity, 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).

[0253] Among the DNA sequences encoding proteins that confer tolerance traits to these animal and microbial pests (especially insects), particular mention will be made of the genetic material encoding Bt proteins from Bacillus thuringiensis, which is widely documented and well known to those skilled in the art. Proteins extracted from bacteria, such as Photorhabdus (WO97 / 17432 and WO98 / 08932), will also be mentioned. In particular, VIP proteins, including Bt Cry or VIP proteins comprising CryA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF proteins or their toxic fragments, and their hybrids or combinations thereof, especially CryF proteins or hybrids derived from CryF proteins (such as hybrid CryA-CrylF 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-CrylAc 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. The VIP3Aa protein or its toxic fragment as described in Acad Sci US A. 28;93(11):5389-94, the Cry protein described in WO2001 / 47952, and insecticidal proteins from strains of the genus Xenorhabdus (as described in WO98 / 50427), the genus Serratia (particularly from S. entomophila), or the species of luminescent bacteria, such as the Tc protein from luminescent bacteria described in WO98 / 08932. Furthermore, this document also includes any variants or mutants of any of the above-described proteins that differ from any of the sequences described above (particularly the sequences of their toxic fragments) at some amino acid (1-10, preferably 1-5), particularly the sequences of their toxic fragments, or any variants or mutants of the above-described proteins fused with a transport peptide (such as a plastid transport peptide) or another protein or peptide.

[0254] Another, and particularly emphasized, example of this characteristic is the conferral of tolerance to one or more herbicides (e.g., imidazolinones, sulfonylureas, glyphosate, or glufosinate). Among the DNA sequences encoding proteins that confer tolerance to certain herbicides in transformed plant cells and plants, the bar or PAT genes or Streptomyces coelicolor genes conferring tolerance to glufosinate-ammonium herbicides as described in WO2009 / 152359, the appropriate EPSPS (5-enolpyruvylshikimate-3-phosphate synthase) genes conferring tolerance to EPSPS-targeting herbicides (especially to glyphosate and its salts), the genes encoding glyphosate-n-acetyltransferase, or the genes encoding glyphosate oxidoreductase will be specifically mentioned. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO2007 / 024782), a mutant Arabidopsis ALS / AHAS gene (e.g., US Patent No. 6,855,533), a gene encoding 2,4-D-monooxygenase conferring tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and a gene encoding Dicamba monooxygenase conferring tolerance to Dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0255] 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, specific references will be made to genetic material from *Glycine tomentella*, for example, any of the publicly available registration series described in WO2019 / 103918: PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256, or PI446961.

[0256] 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.

[0257] 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). (as described in WO2002-120964 or WO2002 / 034946); line 17053 (rice, herbicide resistance, deposited as PTA-9843, described in WO2010 / 117737); line 17314 (rice, herbicide resistance, deposited as PTA-9844, described in WO2010 / 117735); line 281-24-236 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described in WO2005 / 103266 or US-A 2005-216969); line 3006-210-23 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described in US-A 2002-120964 or WO2002 / 034946 ...17053 (rice, herbicide resistance, deposited as PTA-9843, described in WO2010 / 117737); line 17314 (rice, herbicide resistance, deposited as PTA-9844, described in WO2010 / 117735); line 281-24-236 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described in US-A 2002-120964 or WO2002 / 034946); line 3006-210-23 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described 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 (extracted from WO2011 / 075595); strain 5307 (maize, insect control, deposited as ATCCPTA-9561, described in WO2010 / 077816); strain ASR-368 (bent grass, herbicide resistant, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); strain B16 (maize, herbicide resistant, not deposited, described in US-A 2003-126634); strain BPS-CV127- 9 (Soybean, herbicide resistant, deposited as NCIMB 41603, described in WO2010 / 080829); line BLR1 (rapeseed, restored male sterility, deposited as NCIMB 41193, described 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 / 075429). PTA-10442 (extracted from WO2011 / 066384 or WO2011 / 066360); line DP-098140-6 (maize, herbicide resistant, extracted from ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019); line DP-305423-1 (soybean, quality traits, not extracted, described in US-A 2008-312082 or WO2008 / 054747); line DP-32138-1 (maize, hybrid system, extracted from 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 98 / 044140); line FG72 (soybean, herbicide resistant, deposited as PTA-11041, described in WO2011 / 063413); line GA21 (maize, herbicide resistant, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); line GG25 (maize, herbicide resistant, deposited as ATCC 209032, described in US-A 2005-188434 or WO98 / 044140); line GHB119 (cotton, insect control - herbicide resistant, deposited as ATCC PTA-8398, described in WO2008 / 151780); line GHB614 (cotton, herbicide resistant, deposited as ATCC PTA-8398, described in WO2008 / 151780). PTA-6878 (extracted from 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 2004-050282 or WO2007 / 017186); strain JOPLINl (wheat, disease resistant, not deposited, described in US-A 2004-050282 or WO2007 / 017186). 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 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 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 resistance, 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 (as described in 2009-130071 or WO2009 / 064652); line MON87705 (soybean, quality trait - herbicide tolerance, preserved as ATCC PTA-9241, described in US-A2010-0080887 or WO2010 / 037016); line MON87708 (soybean, herbicide tolerance, preserved as ATCC PTA-9670, described in WO2011 / 034704); line MON87712 (soybean, yield, preserved as PTA-10296, described in WO2012 / 051199).Line MON87754 (soybean, quality traits, deposited as ATCC PTA-9385, described in WO2010 / 024976); Line MON87769 (soybean, quality traits, deposited as ATCC PTA-8911, described in US-A2011-0067141 or WO2009 / 102873); Line MON88017 (maize, insect control - herbicide resistance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005 / 059103); Line MON88913 (cotton, herbicide resistance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); strain MON88302 (rapeseed, herbicide resistant, deposited as PTA-10955, described in WO2011 / 153186), strain MON88701 (cotton, herbicide resistant, deposited as PTA-11754, described in WO2012 / 134808), strain MON89034 (maize, insect control, deposited as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); strain MON89788 (soybean, herbicide resistant, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); strain 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 resistant, ATCC registration number PTA-11226, WO2012 / 082548A2), line DP-061061-7 (rapeseed, herbicide resistant, no available accession number, WO2012071039A1), line DP-073496-4 (rapeseed, herbicide resistant, no available accession number, US2012131692), line 8264.44.06.1 (soybean, superimposed herbicide resistant) 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), strain KK179-2 (alfalfa, ATCC registration number PTA-11833, WO2013 / 003558A1), strain pDAB8264.42.32.1 (soybean, superimposed herbicide tolerance, ATCC registration number PTA-11993, WO2013 / 010094A1), strain MZDT09Y (maize, ATCC registration number PTA-13025, WO2013 / 012775A1).

[0258] In addition, the U.S. Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) provides a list of such transgenic lines, which can be found on their website aphis.usda.gov. For the purposes of this application, that list is relevant in its status as of the date of filing.

[0259] Genes / lines that confer desired traits 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 (including apples, pears, citrus fruits, and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed. Specifically emphasized traits include enhanced plant resistance to insects, arachnids, nematodes, slugs, and snails, as well as enhanced plant resistance to one or more herbicides.

[0260] Commercially available examples of such plants, plant parts, or plant seeds that can be preferentially processed according to the present invention include commercially available products, such as plant seeds, sold or distributed under the trade names GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY®2 XTEND™, INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEX™.

[0261] Pathogens Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include: Diseases caused by powdery mildew pathogens, such as species of the genus *Blumeria* (e.g., *Blumeria graminis* of the Poaceae family); species of the genus *Podosphaera* (e.g., *Podosphaera leucotricha*); species of the genus *Sphaerotheca* (e.g., *Sphaerotheca fuliginea*); and species of the genus *Uncinula* (e.g., *Uncinula necator* of grapes). Diseases caused by rust pathogens, such as species of the genus *Gymnosporangium*, including *Gymnosporangium sabinae*; species of the genus *Hemileia*, including *Hemileia vastatrix*; species of the genus *Phakopsora*, including *Phakopsora pachyrhizi* and *Phakopsora meibomiae*; species of the genus *Puccinia*, including *Puccinia recondita*, *Puccinia graminis*, or *Puccinia striiformis*; and species of the genus *Uromyces*, including *Uromyces appendiculatus*. Diseases caused by pathogens derived from oomycetes, such as species of the genera *Albugo* (e.g., *Algubo candida*); species of the genera *Bremia* (e.g., *Bremia lactucae*); species of the genera *Peronospora* (e.g., *Peronospora pisi* or *P. brassicae*); species of the genera *Phytophthora* (e.g., *Phytophthora infestans*); species of the genera *Plasmopara* (e.g., *Plasmopara viticola*); species of the genera *Pseudoperonospora* (e.g., *Pseudoperonospora humuli* or *Pseudoperonospora cubensis*); and species of the genera *Pythium* (e.g., *Pythium quintuplets*). ultimum); Leaf spot and leaf wilt diseases are caused by the following pathogens: species of the genus *Alternaria*, such as *Alternaria solani*; species of the genus *Cercospora*, such as *Cercospora beticola*; species of the genus *Cladiosporum*, such as *Cladiosporium cucumerinum*; species of the genus *Cochliobolus*, such as *Cochliobolus sativus* (conidia form: *Drechslera*, synonym: *Helminthosporium*) or *Cochliobolus miyabeanus*; and species of the genus *Colletotrichum*, such as *Colletotrichum beanus*. * *Lindemuthanium*; species of the genus *Corynespora*, such as *Corynespora cassiicola*; species of the genus *Cycloconium*, such as *Cycloconium oleaginum*; species of the genus *Diaporthe*, such as *Diaporthe citri*; species of the genus *Elsinoe*, such as *Elsinoe fawcettii*; species of the genus *Gloeosporium*, such as *Gloeosporium laeticolor*; species of the genus *Glomerella*, such as *Glomerella cingulata*; species of the genus *Guignardia*, such as *Guignardia*. (bidwelli); species of the genus *Leptosphaeria*, such as *Leptosphaeria maculans*; species of the genus *Magnaporthe*, such as *Magnaporthe grisea*; species of the genus *Microdochium*, such as *Microdochium nivale*; species of the genus *Mycosphaerella*, such as *Mycosphaerella graminicola*, *Mycosphaerella arachidicola*, and *Mycosphaerella fijiensis*;Species of the genus *Phaeosphaeria*, such as *Phaeosphaeria nodorum*; species of the genus *Pyrenophora*, such as *Pyrenophora teres* and *Pyrenophora tritici repentis*; species of the genus *Ramularia*, such as *Ramularia collo-cygni* or *Ramularia areola*; species of the genus *Rhynchosporium*, such as *Rhynchosporium secalis*; species of the genus *Septoria*, such as *Septoria apii* and *Septorialycopersii*; species of the genus *Stagonospora*, such as *Stagonospora nodorum*; and species of the genus *Typhula*, such as *Typhula sarcospora*. Incarnata); species of the genus Venturia, such as Venturia inaequalis, the causal agent of apple black spot; Root and stem diseases caused by the following pathogens: species of the genus *Corticium*, such as *Corticium graminearum*; species of the genus *Fusarium*, such as *Fusarium oxysporum*; species of the genus *Gaeumannomyces*, such as *Gaeumannomyces graminis*; species of the genus *Plasmodiophora*, such as *Plasmodiophora brassicae*; species of the genus *Rhizoctonia*, such as *Rhizoctonia solani*; species of the genus *Sarocladium*, such as *Sarocladium oryzae*; species of the genus *Sclerotium*, such as *Sclerotium oryzae*; and species of the genus *Tapesia*, such as *Tapesia*. acuformis; species of the genus Thieviopsis, such as Thieviopsis basicola; Diseases of the panicle or inflorescence (including the corn cob) caused by the following pathogens: species of the genera *Alternaria*, such as *Alternaria spp.*; species of the genera *Aspergillus*, such as *Aspergillus flavus*; species of the genera *Cladosporium*, such as *Cladosporium cladosporioides*; species of the genera *Claviceps*, such as *Claviceps purpurea*; species of the genera *Fusarium*, such as *Fusarium culmorum*; species of the genera *Gibberella*, such as *Gibberella zeae*; species of the genera *Monographella*, such as *Monographella nivalis*; and species of the genera *Stagonospora*, such as *Stagonospora nodorum*. Diseases caused by smut fungi, such as: species of the genus *Sphacelotheca*, for example *Sphacelotheca reiliana*; species of the genus *Tilletia*, for example *Tilletia caries* or *Tilletia controversa*; species of the genus *Urocystis*, for example *Urocystis occulta*; and species of the genus *Ustilago*, for example *Ustilago nuda*. Fruit rot can be caused by pathogens such as: species of the genus *Aspergillus*, such as *Aspergillus flavus*; species of the genus *Botrytis*, such as *Botrytis cinerea*; species of the genus *Monilinia*, such as *Monilinia laxa*; species of the genus *Penicillium*, such as *Penicillium expansum* or *Penicillium purpurogenum*; species of the genus *Rhizopus*, such as *Rhizopus stolonifer*; species of the genus *Sclerotinia*, such as *Sclerotinias clerotiorum*; and species of the genus *Verticilium*, such as *Verticilium alboatrum*. Seed-borne and soil-borne rot and wilting diseases, as well as seedling diseases, are caused by the following pathogens: species of the genus *Alternaria*, such as *Alternaria brassicicola*; species of the genus *Aphanomyces*, such as *Aphanomyces euteiches*; species of the genus *Ascochyta*, such as *Ascochyta lentis*; species of the genus *Aspergillus*, such as *Aspergillus flavus*; species of the genus *Cladosporium*, such as *Cladosporium herbarum*; and species of the genus *Cochliobolus*, such as *Cochliobolus granatum*. *Sativus* (conidia form: *Drechslera*, *Bipolaris*; synonym: *Helminthosporium*)); species of the genus *Colletotrichum*, such as *Colletotrichum coccodes*; species of the genus *Fusarium*, such as *Fusarium culmorum*; species of the genus *Gibberella*, such as *Gibberella zeae*; species of the genus *Macrophomina*, such as *Macrophomina phaseolina*; species of the genus *Microdochium*, such as *Microdochium nivale*; species of the genus *Monographella*, such as *Monographella nidus*. species of the genera *Penicillium*, such as *Penicillium expansum*; species of the genera *Phoma*, such as *Phoma lingam*; species of the genera *Phomopsis*, such as *Phomopsis sojae*; species of the genera *Phytophthora*, such as *Phytophthora cactorum*; species of the genera *Pyrenophora*, such as *Pyrenophora graminea*; species of the genera *Pyricularia*, such as *Pyricularia oryzae*; and species of the genera *Pythium*, such as *Pythium ultimum*.Species of the genus *Rhizoctonia*, such as *Rhizoctonia solani*; species of the genus *Rhizopus*, such as *Rhizopus oryzae*; species of the genus *Sclerotium*, such as *Sclerotium rolfsii*; species of the genus *Septoria*, such as *Septorianodorum*; species of the genus *Typhula*, such as *Typhula incarnata*; and species of the genus *Verticillium*, such as *Verticillium dahliae*. Cancerous diseases, fungal galls, and broom diseases caused by the following pathogens: for example, species of the genus *Nectria*, such as *Nectria galligena*. Wilting diseases caused by the following pathogens: for example, species of the genus *Verticillium*, such as *Verticillium longisporum*; species of the genus *Fusarium*, such as *Fusarium oxysporum*. Deformities of leaves, flowers, and fruits caused by the following pathogens: for example, species of the genus *Exobasidium*, such as *Exobasidium vexans*; species of the genus *Taphrina*, such as *Taphrina deformans*. Degenerative diseases of woody plants caused by the following pathogens: for example, species of the genus *Esca*, such as *Phaemoniella chlamydospora*, *Phaeoacremonium aleophilum*, or *Fomitiporia mediterranea*; for example, species of the genus *Ganoderma*, such as *Ganoderma boninense*; Diseases of plant tubers caused by the following pathogens: for example, species of the genus Rhizoctonia, such as Rhizoctonia solani; species of the genus Helminthosporium, such as Helminthosporium solani. Diseases caused by the following bacterial pathogens include species of the genus *Xanthomonas*, such as *Xanthomonas campestris* pv. *oryzae*; species of the genus *Pseudomonas*, such as *Pseudomonas syringae* pv. *lachrymans*; species of the genus *Erwinia*, such as *Erwinia amylovora*; species of the genus *Liberibacter*, such as *Liberibacter asiaticus*; species of the genus *Xyella*, such as *Xylella fastidiosa*; species of the genus *Ralstonia*, such as *Ralstonia solanacearum*; species of the genus *Dickeya*, such as *Dickeya solani*; and species of the genus *Clavibacter*, such as *Clavibacter*. michiganensis; species of the genus Streptomyces, such as Streptomyces scabies.

[0262] Soybean diseases: Fungal diseases affecting leaves, stems, pods, and seeds caused by the following pathogens: for example, Alternaria leaf spot (Alternaria spec.atrans tenuissima) and anthracnose (Colletotrichum gloeosporoides dematium var.).truncatum, brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora), Dactuliophora leaf spot (Dactuliophora glycines), soybean downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), soybean frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina clover). Trifolii), Phyllostachyca leaf spot (Phyllostica leaf spot) (Phyllosticta sojaecola), pod and stem wilt (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), Rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), Stemphylium leaf blight (Stemphylium) (Botryosum), sudden death syndrome (Fusarium virguliforme), target spot disease (Corynespora cassiicola).

[0263] Fungal diseases of the roots and stems caused by the following pathogens include: black root rot (Calonectria crotalariae), anthracnose (Macrophomina phaseolina), Fusarium wilt or wilting, root rot, and pod and root collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), and stem canker (Diaporthe phaseolorum). var. caulivora), Phytophthoramegasperma, Soybean brown rot, Pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia solani, Sclerotinia sclerotiorum, Sclerotinia rolfsii, Thieviopsis root rot (Thielaviopsis basicola).

[0264] Mycotoxins Furthermore, the compounds of formula (I) and the compositions of the present invention can reduce the content of mycotoxins in harvested materials and foods and feeds derived therefrom. Specifically, mycotoxins 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, and ergot alkaloids. Alkaloids and aflatoxins, which can be produced by fungi such as those in the genus *Fusarium*, including *F. acuminatum*, *F. asiaticum*, *F. avenaceum*, *F. crookwellense*, *F. culmorum*, *F. graminearum* (*Gibberella zeae*), *F. equiseti*, *F. fujikoroi*, *F. musarum*, *F. oxysporum*, *F. proliferatum*, *F. poae*, *F. pseudograminearum*, *F. sambucinum*, *F. scirpi*, and *F. semi-naked*. *Fusarium semitectum*, *F. solani*, *F. sporotrichoides*, *F. langsethiae*, *F. subglutinans*, *F. trifilctum*, *F. verticillioides*, etc.; and species of the genus *Aspergillus*, such as *A. flavus*, *A. parasiticus*, *A. nomius*, *A. ochraceus*, *A. clavatus*, *A. terreus*, and *A. variegated*.* *Penicillium* species, such as *Penicillium verrucosum*, *Penicillium viridicatum*, *Penicillium citrinum*, *Penicillium expansum*, *Penicillium claviforme*, and *Penicillium roqueforti*; *Claviceps* species, such as *Claviceps purpurea*, *Claviceps fusiformis*, *Claviceps paspali*, and *Claviceps africana*; *Stachybotrys* species and others.

[0265] Material protection The compounds of formula (I) and the compositions of the present invention can also be used in material protection, especially for protecting industrial materials from attack and damage by plant pathogenic fungi.

[0266] Furthermore, the compounds of formula (I) and the compositions of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

[0267] In this document, industrial materials should be understood to mean non-living 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.

[0268] The compounds of formula (I) and the compositions of the present invention can prevent a variety of adverse effects, such as rotting, decay, discoloration, fading or mold.

[0269] In the case of treating wood, the compounds of formula (I) and the compositions of the present invention can also be used to resist fungal diseases that are prone to grow on or inside the wood.

[0270] Timber 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 of formula (I) and the compositions of the present 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.

[0271] The compounds of formula (I) and the compositions of the present invention can also be used to protect stored materials. Stored materials 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 materials, 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 materials 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 materials include, for example, hides, leather, fur, and hair. The compounds of formula (I) and the compositions of the present invention can prevent a variety of adverse effects, such as rot, decay, discoloration, fading, or mold.

[0272] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. The compounds of formula (I) and the compositions of the present invention preferably act on fungi, especially molds, wood-discoloring and wood-damaging fungi (Ascomycetes, Basidiomycetes, Deuteromycetes, and Zygomycetes), and on slime organisms and algae.Examples include microorganisms from the following genera: *Alternaria*, such as *Alternaria tenuis*; *Aspergillus*, such as *Aspergillus niger*; *Chaetomium*, such as *Chaetomium globosum*; *Coniophora*, such as *Coniophorapuetana*; *Lentinus*, such as *Lentinus tigrinus*; *Penicillium*, such as *Penicillium glaucum*; *Polyporus*, such as *Polyporus versicolor*; *Aureobasidium*, such as *Aureobasidium pullulans*; and *Sclerophoma*, such as *Sclerophoma*. * *Trichoderma*, such as *Trichoderma viride*; *Ophiostoma* spp., *Ceratocystis* spp., *Humicola* spp., *Petriella* spp., *Trichurus* spp., *Coriolus* spp., *Gloeophyllum* spp., *Pleurotus* spp., *Poria* spp., *Serpula* spp., and *Tyromyces* spp., *Cladosporium* spp., *Penicillium*, *Mucor*, and *Escherichia*, such as *Escherichia coli*; *Pseudomonas*, such as *Pseudomonas aeruginosa*. Staphylococcus, such as Staphylococcus aureus, Candida, and Saccharomyces spp., such as Saccharomyces cerevisae.

[0273] Seed treatment The compounds of formula (I) and the compositions of the present invention can be used to protect seeds from unwanted microorganisms such as plant pathogenic microorganisms such as plant pathogenic fungi or plant pathogenic oomycetes. The term seed as used herein includes dormant seeds, primed seeds, pre-germinated seeds, or even seeds that have developed roots and leaves.

[0274] 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 of formula (I) or a composition of the present invention.

[0275] Treating seeds with a compound of formula (I) or a composition of the present invention can protect 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 methods for protecting seeds, germinating seeds, and newly emerging seedlings.

[0276] Seed treatment can be performed before sowing, at sowing, or shortly after sowing.

[0277] 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 of formula (I) or the composition of the present invention, and the seeds and the compound of formula (I) or the composition of the present invention can be mixed until they are evenly distributed on the seeds. If appropriate, the seeds can be dried.

[0278] The present invention also relates to seeds coated with compounds of formula (I) or compositions of the present invention.

[0279] 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 pretreated, or seeds stored under pretreated conditions, or pre-germinated seeds, or seeds planted in nursery trays, strips, or paper can also be used.

[0280] The amount of the compound of formula (I) or the composition of the present invention applied to the 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 phytotoxic effects 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.

[0281] 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.

[0282] The compounds of formula (I) and the compositions 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.

[0283] The compounds of formula (I) and the compositions of the present invention can be used to treat transgenic seeds, particularly plant seeds capable of expressing polypeptides or proteins that are effective against pests, herbicide damage, or abiotic stress, thereby increasing protection. Plant seeds capable of expressing polypeptides or proteins that resist pests, herbicide damage, or abiotic stress 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 Bacillus, wherein the gene product is effective against the European corn borer and / or the Western corn rootworm. Particularly preferably, the heterologous gene is derived from Bacillus thuringiensis.

[0284] application The compound of formula (I) may be used on its own or in the form of, for example, ready-to-use solutions, emulsions, water-based or oil-based suspensions, powders, wettable powders, ointments, 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.

[0285] Application can be made by conventional methods, such as watering, spraying, atomizing, spreading, dusting, foaming, or sprinkling. Compounds of formula (I) can also be applied via ultra-low volume methods, using drip irrigation systems or watering, 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.

[0286] 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 (dusting, 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.

[0287] 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 from 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 from 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 from 0.1 to 10,000 g / ha, preferably 1 to 5,000 g / ha.

[0288] These application rates are merely examples and are not intended to limit the scope of the invention.

[0289] The compounds of formula (I) and the compositions 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 to support site-specific management of agricultural sites, such as soil, weather, crops (e.g., variety, growth stage, plant health), weeds (e.g., variety, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., 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.

[0290] 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.

[0291] 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.

[0292] The compounds of formula (I) can also be used in combination with intelligent spraying equipment, such as spot or precision spraying equipment attached to or housed within agricultural vehicles (e.g., tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs) such as drones). Such equipment typically includes input sensors (e.g., cameras) and a processing unit configured to analyze the input data and to provide decisions based on the analysis of the input data, applying the compounds of the invention to crop plants (i.e., weeds) in a specific and precise manner. The use of such intelligent spraying equipment typically also requires a positioning system (e.g., a GPS receiver) to locate the recorded data and guide or control the agricultural vehicle; a geographic information system (GIS) to represent the information on an understandable map; and appropriate agricultural vehicles to perform the required agricultural actions, such as spraying.

[0293] 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 only be used when needed.

[0294] The teachings of the present invention can be further understood from the following embodiments, which should not be construed as limiting the scope of the invention in any way.

[0295] A. Example A-1. General Section 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] The LogP value was determined by LC-UV measurement in the acidic range using 0.1% formic acid aqueous solution and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0296] [b] The LogP value was 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).

[0297] [c] The LogP value was determined by LC-UV measurement in the acidic range using 0.1% phosphoric acid and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0298] If more than one LogP value can be obtained within the same method, all values ​​are shown and separated by "+".

[0299] 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 successive alkyl-2-ones). λmax values ​​were determined using UV spectra from 200 nm to 400 nm and peak values ​​of chromatographic signals.

[0300] 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 the form of a list. For each signal peak, the δ value in ppm is listed, and the signal intensity is listed in parentheses. The δ value-signal intensity pairs are separated by semicolons.

[0301] Therefore, the peak list for an instance takes the following form: δ1 (Intensity 1); δ2 (Intensity 2); ...; δi (Intensity i); ...; δn (Intensity n) The intensity of a sharp signal is highly correlated with the signal of a printed example of an NMR spectrum measured in centimeters, and the true relationship of signal intensity is shown. A broad signal can show multiple peaks or the midpoint of the signal and their relative intensity compared to the strongest signal in the spectrum.

[0302] 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.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] 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).

[0307] 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 a "byproduct fingerprint".

[0308] Experts who calculate the target compound peaks using known methods (MestreC, ACD simulation, and expected values ​​based on empirical assessment) 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.

[0309] 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.

[0310] A-1.3 Abbreviation The following examples illustrate the preparation and bioactivity of compounds of formula (I) according to the present invention in a non-limiting manner.

[0311] A-2. Synthesis of compounds of formula (I) and their intermediates Preparation Example 1: Preparation of (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (Compound I-002) Step 1: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)pyridazine-4-carboxamide (intermediate 14-002) In a 50 mL double-necked round-bottom flask, under argon atmosphere and at 0 °C, HATU (690 mg, 1.76 mmol) dissolved in 3 mL of anhydrous DMF was added to a solution of 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (430 mg, 1.67 mmol) dissolved in 7 mL of anhydrous DMF. The resulting mixture was stirred at 0 °C for 15 min, and then 1-chloro-3-(2-chloro-4-methylphenyl)prop-2-amine hydrochloride (1:1) (443 mg, 1.76 mmol) and N,N-diisopropylethylamine (0.88 mL, 5.03 mmol) were added. After 30 min at 0 °C, the reaction mixture was warmed 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 purified by rapid chromatography (20% to 80% in ethyl acetate in n-heptane) to give the title compound (681 mg, purity 89%, yield 100%).

[0312] Step 2: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)-N'-hydroxypyridazine-4-carboximidamide (intermediate 15-002) Under argon atmosphere and at room temperature, phosphorus pentachloride (930 mg, 4.47 mmol) was added to a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propyl-2-yl]-5-(3-cyclopropylphenoxy)pyridazine-4-carboxamide (intermediate 14-002) (680 mg, 1.49 mmol) in 10 mL of toluene, and the mixture was stirred at 80 °C for 1 hour. After cooling to room temperature, the residue was diluted with 2 mL of dioxane and then carefully added to 30 mL of 50% hydroxylamine aqueous solution (489 mmol) at room temperature. After stirring at room temperature for 45 minutes, the reaction mixture was poured into HCl 6N to adjust the pH to 6 to 7, extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and then concentrated under vacuum. The compound was used directly without further purification.

[0313] Step 3: Preparation of (5RS)-5-(2-chloro-4-methylbenzyl)-3-[5-(3-cyclopropylphenoxy)pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (Compound I-002) 1.1 mL of 1N sodium hydroxide aqueous solution (1.1 mmol) was added to a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)prop-2-yl]-5-(3-cyclopropylphenoxy)-N'-hydroxypyridazine-4-formamidin (intermediate 15-003) (704 mg, 67% purity, 1 mmol) in 10 mL of isopropanol, and stirred at room temperature for 15 minutes. The reaction mixture was then poured into brine, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was first purified by rapid chromatography (10% to 80% in ethyl acetate in n-heptane), and then a second purification was performed using an SFC CO2 / methanol 20% column: Waters 2 EP 30 × 150, to give the title compound (66 mg, 99% purity, 15% yield).

[0314] Preparation Example 2: Preparation of (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (Compound I-026) Step 1: Preparation of 5-(3-chloro-2-fluorophenoxy)-N-[(2RS)-1-(2-chloro-4-methylphenyl)-3-hydroxypropyl-2-yl]-3-methylpyridazine-4-carboxamide (Intermediate 14-013) In a 50 mL double-necked round-bottom flask under argon atmosphere at 0 °C, HATU (407 mg, 1.04 mmol) was added to a solution of 5-(3-chloro-2-fluorophenoxy)-3-methylpyridazine-4-carboxylic acid (280 mg, 0.99 mmol) in 5 mL of anhydrous DMF. The resulting mixture was stirred at 0 °C for 15 min, and then 2-amino-3-(2-chloro-4-methylphenyl)prop-1-ol hydrochloride (1:1) (264 mg, 1.76 mmol) and N,N-diisopropylethylamine (0.52 mL, 2.97 mmol) were added. After one hour at room temperature, 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 purified by rapid chromatography (20% to 80% in ethyl acetate in n-heptane) to give the title compound (369 mg, 85% purity, 80% yield).

[0315] Step 2: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)prop-2-yl]-5-(3-chloro-2-fluorophenoxy)-N'-hydroxy-3-methylpyridazine-4-formamidinium (intermediate 15-013) Under argon atmosphere and at room temperature, phosphorus pentachlor (89 mg, 0.43 mmol) was added to a solution of 5-(3-chloro-2-fluorophenoxy)-N-[(2RS)-1-(2-chloro-4-methylphenyl)-3-hydroxypropyl-2-yl]-3-methylpyridazine-4-carboxamide (intermediate 14-013) (50 mg, 0.19 mmol) in 1 mL of toluene, and the mixture was stirred at 80 °C for 1 hour. After cooling to room temperature, the residue was diluted with 2 mL of dioxane and then carefully added to 1.98 mL of 50% hydroxylamine aqueous solution (32 mmol) at room temperature. After stirring at room temperature for one hour, the reaction mixture was poured into HCl 6N to adjust the pH to 6 or 7, extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and then concentrated under vacuum. The compound was used directly without further purification.

[0316] Step 3: Preparation of (5RS)-3-[5-(3-chloro-2-fluorophenoxy)-3-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (Compound I-026) 0.094 mL of 1N sodium hydroxide aqueous solution (0.09 mmol) was added to a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)prop-2-yl]-5-(3-chloro-2-fluorophenoxy)-N'-hydroxy-3-methylpyridazine-4-formamidinium (intermediate 15-013) (42 mg, 79% purity, 0.08 mmol) in 1 mL of isopropanol, and the mixture was stirred at room temperature for 25 minutes. The reaction mixture was then poured into brine, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by rapid chromatography (10% to 80% in ethyl acetate in n-heptane) to give the title compound (13 mg, 76% purity, 25% yield).

[0317] Preparation Example 3: Preparation of (5RS)-5-[2-methyl-4-(prop-1-en-2-yl)benzyl]-3-{3-methyl-5-[3-(prop-1-en-2-yl)benzyl]pyridazin-4-yl}-5,6-dihydro-4H-1,2,4-oxadiazine (Compound I-025) (5RS)-5-(4-bromo-2-methylbenzyl)-3-[5-(3-chlorobenzyl)-3-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (compound I-007) (247 mg, 0.5 mmol), pinacol isopropenylborate [126726-62-3] (170 mg, 1.01 mmol), cesium carbonate (247 mg, 0.76 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) [72287-26-4] (20 mg, 0.02 mmol) were dissolved in a degassed mixture of 1.5 mL of 1,4-dioxane and 0.7 mL of water. The reaction mixture was heated in a microwave oven at 130 °C for 30 minutes. The reaction mixture was then poured into a saturated aqueous solution of NaHCO3 and extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a heptane / ethyl acetate gradient (70:30 to 0:100) to give the title compound (66 mg, 99% purity, 28% yield).

[0318] Synthetic intermediates Preparation Example 4: Preparation of 5-(3-cyclopropylphenoxy)-N-{(2RS)-1-(2,4-dimethylphenyl)-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl-2-yl}pyridazine-4-carboxamide (intermediate 3-001) In a round-bottom flask under argon atmosphere and at 0 °C, HATU (329 mg, 0.84 mmol) and 2-{[(2RS)-2-amino-3-(2,4-dimethylphenyl)propyl]oxy}-1H-isoindole-1,3(2H)-dione trifluoroacetate (1:1) (368 mg, 0.84 mmol) were added to a solution of 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (205 mg, 0.80 mmol) in 4 mL of anhydrous DMF. Then, N,N-diisopropylethylamine (0.42 mL, 2.4 mmol) was added dropwise, and the resulting mixture was stirred at 0 °C for 30 min, followed by warming to room temperature and stirring for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography using a heptane / ethyl acetate gradient (8:2 to 2:8) to give the title compound (500 mg, 94% purity, 99% yield).

[0319] Preparation Example 5: Preparation of N-[(2RS)-1-(aminooxy)-3-(2,4-dimethylphenyl)propyl-2-yl]-5-(3-cyclopropylphenoxy)pyridazine-4-carboxamide (intermediate 4-001) In a 50 mL round-bottom flask under argon atmosphere, hydrazine monohydrate (0.182 mL, 2.4 mmol) was added at room temperature to a solution of 5-(3-cyclopropylphenoxy)-N-{(2RS)-1-(2,4-dimethylphenyl)-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl-2-yl}pyridazine-4-carboxamide (intermediate 3-001) (450 mg, 0.80 mmol) in a 1:1 mixture of CH2Cl2 and methanol. The resulting suspension was stirred at room temperature for 2 hours. The white precipitate was removed by filtration and washed with CH2Cl2. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum to give the title compound (241 mg, 89% purity, 62% yield).

[0320] Table 1: Compounds according to formula (I) Table 2: Compounds of Formula (I) 1 H-NMR data Table 3: Compounds according to formula (3) Table 4: Compounds of Formula (3) 1 H-NMR data Table 5: Compounds according to formula (4) Table 6: Compounds of Formula (4) 1 H-NMR data Table 7: Compounds according to formula (14) Table 8: Compounds of Formula (14) 1 H-NMR data Table 9: Compounds according to formula (15) Table 10: Compounds of Formula (15) 1 H-NMR data B. Biological Examples B-1. In vivo prophylactic test against Alternaria brassicae (leaf spot disease of radish or cabbage). Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient The active ingredient is dissolved and homogenized in a mixture of dimethyl sulfoxide / acetone / Tween® 80, and then diluted in water to the desired concentration.

[0321] Young radish or cabbage plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0322] 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.

[0323] The experiment was evaluated 3 to 4 days after inoculation. 0% means efficacy equivalent to the control plant, while 100% efficacy means no disease was observed.

[0324] 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-05, I-15, and I-16.

[0325] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-01, I-02, I-03, I-04, I-06, I-07, I-08, I-09, I-11, I-12, I-14, I-24, I-26. B-2. In vivo prophylactic test against Botrytis cinerea (grey mold) Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient The active ingredient is dissolved and homogenized in a mixture of dimethyl sulfoxide / acetone / Tween® 80, and then diluted in water to the desired concentration.

[0326] Young cucumber or cabbage plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0327] 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.

[0328] The experiment was evaluated 4 to 5 days after inoculation. 0% means efficacy equivalent to the control plant, while 100% efficacy means no disease was observed.

[0329] 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-04.

[0330] 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-15, I-17.

[0331] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-01, I-02, I-03, I-05, I-06, I-07, I-08, I-09, I-11, I-12, I-14, I-16, I-24, I-26.

[0332] B-3. ​​In vivo prophylactic test against Pyrenophora teres (net blotch on barley) Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient The active ingredient is dissolved and homogenized in a mixture of dimethyl sulfoxide / acetone / Tween® 80, and then diluted in water to the desired concentration.

[0333] Young barley plants were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0334] 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.

[0335] The experiment was evaluated 10 days after inoculation. 0% means efficacy equivalent to the control plant, while 100% efficacy means no disease was observed.

[0336] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: I-02, I-14, I-15, and I-24.

[0337] 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-01, I-03, I-04, I-06, I-07, I-08, I-09, I-11, I-12, and I-26.

[0338] B-4. In vivo prophylactic test against *Sphaerotheca fuliginea* (powdery mildew of cucurbits) Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient The active ingredient is dissolved and homogenized in a mixture of dimethyl sulfoxide / acetone / Tween® 80, and then diluted in water to the desired concentration.

[0339] Cucumber seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0340] 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.

[0341] The experiment was evaluated 8 days after inoculation. 0% means efficacy equivalent to the control plant, while 100% efficacy means no disease was observed.

[0342] In this experiment, the following compound of the present invention showed 80% to 89% efficacy at an active ingredient concentration of 500 ppm: I-12.

[0343] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-01, I-02, I-03, I-06, I-07, I-08, I-09, I-11, I-24, and I-26.

[0344] B-5. In vivo prophylactic test against Colletotrichum lindemuthianum (leaf spot on bean) Solvent: 5% by volume dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient The active ingredient is dissolved and homogenized in a mixture of dimethyl sulfoxide / acetone / Tween® 80, and then diluted in water to the desired concentration.

[0345] Young beans were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0346] 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.

[0347] The experiment was evaluated 7 days after inoculation. 0% means efficacy equivalent to the control plant, while 100% efficacy means no disease was observed.

[0348] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: I-05, I-26.

[0349] 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-15, I-16.

[0350] In this experiment, the following compounds of the present invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I-01, I-02, I-03, I-04, I-06, I-07, I-08, I-09, I-11, I-12, and I-24.

[0351] B-6. In vitro cell assay of Alternaria alternata Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g mycological 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%.

[0352] Prepare a spore suspension of Alternaria alternata and dilute it to the desired spore density.

[0353] 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.

[0354] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 50 μMol / l: I-05, I-10, I-19, I-20, and I-22.

[0355] 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-09, I-13, I-14, I-15, I-16, I-17, and I-21.

[0356] 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-01, I-02, I-03, I-04, I-06, I-07, I-08, I-11, I-12, I-24, and I-26.

[0357] B-7. In vitro cell assay of Colletotrichum lindemuthanium 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%.

[0358] Prepare a spore suspension of *Anthracis bean* and dilute it to the desired spore density.

[0359] In liquid culture assays, the ability of fungicides to inhibit spore germination and hyphal growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 6 days of incubation, the fungal toxicity of the compound was determined by measuring hyphal 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.

[0360] 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-01, I-02, I-03, I-04, I-05, I-06, I-07, I-08, I-09, I-11, I-12, I-14, I-15, I-16, I-17, I-24, I-26.

[0361] B-8. Extracellular assay of Pyrenophora teres 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%.

[0362] Prepare a spore suspension of Cynocordiella spores and dilute it to the desired spore density.

[0363] In liquid culture assays, the ability of fungicides to inhibit spore germination and hyphal growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 6 days of incubation, the fungal toxicity of the compound was determined by measuring hyphal 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.

[0364] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 50 μMol / l: I-19, I-21, and I-22.

[0365] In this experiment, the following compound of the present invention showed 80% to 89% efficacy at an active ingredient concentration of 50 μMol / l: I-13.

[0366] 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-01, I-02, I-03, I-04, I-05, I-06, I-07, I-08, I-09, I-11, I-12, I-14, I-15, I-16, I-17, I-24, I-26.

[0367] B-9. In vitro cell assay of Botrytis cinerea 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 biotin (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%.

[0368] Prepare a suspension of Botrytis cinerea spores and dilute it to the desired spore density.

[0369] 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, 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.

[0370] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 50 μMol / l: I-20, I-21, and I-25.

[0371] 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-01, I-02, I-03, I-04, I-05, I-06, I-07, I-08, I-09, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-24, I-26.

[0372] B-10. In vitro cell assay of Fusarium culmorum 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 biotin (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%.

[0373] Prepare a suspension of Fusarium spores and dilute it to the desired spore density.

[0374] In liquid culture assays, the ability of fungicides to inhibit spore germination and hyphal growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 5 days of incubation, hyphal 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.

[0375] In this experiment, the following compounds of the present invention showed efficacy of 70% to 79% at an active ingredient concentration of 50 μMol / l: I-01, I-02, I-05, I-17, and I-24.

[0376] 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-04, I-08, and I-11.

[0377] B-11. In vitro cell assay of wheat septoria tritici 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 biotin (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%.

[0378] Prepare a spore suspension of *Syngonium vesicanthum* and dilute it to the desired spore density.

[0379] In liquid culture assays, the ability of fungicides to inhibit spore germination and hyphal growth was evaluated. The compound was added to spore-containing medium at the desired concentration. After 7 days of incubation, hyphal 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.

[0380] 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-04, I-11, and I-24.

Claims

1. Compounds of formula (I) ###0001### and the N-oxides, salts, hydrates of the salts and the hydrates of the N-oxides thereof, wherein L is a direct bond or Ci-C4-alkylene, - wherein the Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkylsulfanyl and Ci-C6-haloalkylsulfanyl are in turn optionally substituted with one to three substituents independently selected from the group consisting of fluorine, chlorine, hydroxyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl, - and wherein the C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, 5- or 6-membered heteroaryl are in turn optionally substituted with one to three substituents independently selected from the group consisting of fluorine, chlorine, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl and C3-C6-cycloalkyl.

2. Compounds of formula (I) according to claim 1, wherein L is a direct bond, methylene, 1,1 -ethylidene or 1,2-ethylidene, ###0002### wherein the Ci-C4-alkyl, Ci-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of hydroxyl and Ci-C4-alkoxy, ###0003### and the salts, hydrates of the salts and the hydrates of the N-oxides thereof. R 3 and R 4 independently are hydrogen, fluorine or Ci-C4-alkyl, R 5 is hydrogen, ​ ​ - said Ci-C4-alkylene is optionally substituted by one or two substituents L SA substituted, L SA R1is H, halogen, C1-6alkyl, C1-6halo ​ two substituents L attached to the same carbon atom SA form, together with the carbon atom to which they are attached, a cyclopropyl ring or a cyclobutyl ring, R 6 C3-C 12 - carbocyclyl, C6-C 14 - aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 - carbocyclyloxy, C6-C 14 - aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 - carbocyclylthio, C6-C 14 - arylthio, 5- to 14-membered heteroarylthio, 3- to 14-membered heterocyclylthio, C1-C3- alkoxy, C1-C3-haloalkoxy, -wherein the C1-C3-alkoxy group and the C1-C3-haloalkoxy group are selected from C3-C 12 -Carbocyclic group, C6-C 14 Substituents of -aryl, 3 to 14-membered heterocyclic and 5 to 14-membered heteroaryl groups -- wherein said C3-C 12 - carbocyclyl, C6-C 14 - aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl groups are in turn optionally substituted with one to three R 6S substituents, - wherein C3-C 12 - carbocyclyl, C6-C 14 - aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 - carbocyclyloxy, C6-C 14 - aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 - carbocyclylthio, C6-C 14 - arylthio, 5- to 14-membered heteroarylthio and 3- to 14-membered heterocyclylthio optionally substituted with one to three R 6S substituents, ​ R 6S independently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluoro- sulfanyl, 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-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- oxy, C6-C10-aryloxy, C6-C10-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 ) and -C(=O)N(R 18 )2, ​ ​ - C3-C6-cycloalkyl, which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; 14 - aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl, which are optionally substituted by one to three substituents independently selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, ​ R 17 and R 18 independently are hydrogen, C1-C4-alkyl or C1-C4-haloalkyl, ​ R 7 is hydrogen, fluorine, chlorine or Ci-C4-alkyl, R 8 halogen or Ci-C4-alkyl, Q represents phenyl, naphthyl, or C3-C. 10 -Carbocyclic, 5- to 10-membered heterocyclic or 5- to 10-membered heteroaryl wherein phenyl, naphthyl, C3-C10cycloalkyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl are optionally substituted by one to three substituents Q 10 - carbocyclyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl are optionally substituted by one to three substituents Q S substituted, ​ Q S independently from each other selected from the group consisting of halogen, cyano, nitro, formyl, carboxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxyl, C1-C4-haloalkoxyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, 5- or 6-membered heteroaryl, ​ ​ ​ ​ R 3 and R 4 are independently hydrogen, fluoro or methyl, R 5 is hydrogen, ​ ​ - said methylene, 1,1-ethylidene and 1,2-ethylidene groups are optionally substituted by one or two substituents L SA substituted, L SA are fluorinated, ​ two substituents L attached to the same carbon atom SA form, together with the carbon atom to which they are attached, a cyclopropyl ring or a cyclobutyl ring, R 6 is indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxinyl, furanyl, thienyl, indolyl or benzofuranyl, - wherein the indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxinyl, furanyl, thienyl, indolyl and benzofuranyl groups are optionally substituted with one or two R 6S substituents, ​ R 6S independently selected from fluorine, chlorine, Ci-C4-alkyl, difluoromethyl, trifluoromethyl, Ci-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridinyl, ​ ​ - wherein C3-C6-cycloalkyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridinyl are in turn optionally substituted with one or two substituents independently selected from fluorine, chlorine and C1-C4-alkyl, R 7 is hydrogen, fluorine, chlorine or methyl, R 8 is hydrogen, fluorine, chlorine or methyl, Q is phenyl, thienyl or pyridinyl, - wherein phenyl, thienyl and pyridyl are optionally substituted by one or two substituents Q S substituted, wherein Q S independently from each other selected from the group consisting of halogen, Ci-C4-alkyl, difluoromethyl, trifluoromethyl, Ci-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl, - wherein - said C3-C6-cycloalkyl is in turn optionally substituted with one or two substituents independently selected from fluorine, chlorine and methyl.

3. The compounds of formula (I) according to claim 1 or 2, and salts, hydrates and hydrates of salts thereof, wherein R 3 and R 4 is hydrogen R 5 is hydrogen, L is methylene, R 7 is hydrogen, R 8 is hydrogen, chloro or methyl.

4. The compounds of formula (I) according to any one of claims 1 to 3, and salts, hydrates and hydrates of salts thereof, wherein Q is a group of the formula wherein 2 for the linking bond to an oxygen atom, Q S1 is hydrogen or fluorine, Q S2 is chloro, trifluoromethyl, isoprenyl or cyclopropyl.

5. The compounds of formula (I) according to any one of claims 1 to 4, wherein R 6 is phenyl, wherein said phenyl is substituted with one or two R 6S substituted with one or two R wherein R 6S independently selected from chloro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl, allyl, and isoprenyl.

6. The compounds of formula (I) according to any one of claims 1 to 5, wherein the compound of formula (I) is: (5RS)-5-(2-bromo-4-methylbenzyl)-3-[5-(3-chlorophenoxy)-3-methylpyridazin-4-yl]- 5,6-dihydro-4H-l,2,4-oxadiazine.

7. A composition for controlling phytopathogenic harmful fungi, which comprises at least one compound of formula (I) according to any one of claims 1 to 6 and at least one carrier and / or surfactant.

8. A method for controlling harmful microorganisms in crop protection and in the protection of materials, characterized in that, At least one compound of formula (I) according to any one of claims 1 to 6 and / or a composition according to claim 7 is applied to the harmful microorganisms and / or their habitat.

9. The method of claim 8, wherein the harmful microorganism is a pathogenic oomycete or a plant pathogenic fungus selected from the group consisting of Podosphaera spp., Sphaerotheca spp., Uncinula spp., Gymnosporangium spp., Hemileia spp., Phakopsora spp., Puccinia spp., Uromyces spp., Albugo spp., Bremia spp., Peronospora spp., Phytophthora spp., Plasmopara spp., Pseudoperonospora spp., Pythium spp., Alternaria spp., Cercospora spp., Cladiosporium spp., Cochliobolus spp., Corynespora spp., Cycloconium spp., Diaporthe spp., Elsinoe spp., Gloeosporium spp., Glomerella spp., Guignardia spp., Leptosphaeria spp., Magnaporthe spp., Microdochium spp., Mycosphaerella spp., Phaeosphaeria spp., Pyrenophora spp., Ramularia spp., Rhynchosporium spp., Septoria spp., Stagonospora spp., Typhula spp., Venturia spp., Corticium spp., Fusarium spp., Gaeumannomyces spp., Plasmodiophora spp., Rhizoctonia spp., Sarocladium spp., Sclerotium spp., Tapesia spp., Thielaviopsis spp., Aspergillus spp., Claviceps spp.,Gibberella spp., Monographella spp., Stagnospora spp., Sphacelotheca spp., Tilletia spp., Urocystis spp., Ustilago spp., Monilinia spp., Penicillium spp., Rhizopus spp., Sclerotinia spp., Verticilium spp., Aphanomyces spp., Ascochyta spp., Cladosporium spp., Macrophomina spp., Phoma spp., Phomopsis spp., Pyricularia spp., Verticillium spp., Nectria spp., Exobasidium spp., Taphrina spp., Esca spp., Ganoderma spp., Helminthosporium spp., Xanthomonas spp., Pseudomonas spp., Erwinia spp., Liberibacter spp., Xyella spp., Ralstonia spp., Dickeya spp., Clavibacter spp., Streptomyces spp., Colletotrichum gloeosporoides dematium var. truncatum, Choanephora infundibulifera trispora (Syn.), Dactuliophora glycines, Drechslera glycini, Leptosphaerulina trifolii, Phyllosticta sojaecola, Microsphaera diffusa, Pyrenochaeta glycines, Sphaceloma glycines,Stemphylium botryosum, Calonectria crotalariae, Mycoleptodiscus terrestris, Neocosmospora vasinfecta, and Phialophora gregata.

10. The method according to claim 8, wherein the harmful microorganisms are selected from the group consisting of Alternaria alternata, Alternaria brassicae, Pyrenophora teres, Sphaerotheca fuliginea, Fusarium culmorum and Septoria tritici.

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