TW202214107A - 1,3,4-oxadiazole pyrimidines as fungicides - Google Patents

Abstract

The present invention relates to 1,3,4-oxadiazole pyrimidine compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.

Description

1,3,4-Diazolopyrimidine as a fungicide

二唑-2-基嘧啶化合物、用於彼等製備之方法和中間物、以及其在作物保護中用於控制有害微生物(特別用於植物病原性真菌)之用途。 The present invention relates to 1,3,4-

Diazol-2-ylpyrimidine compounds, processes and intermediates for their preparation, and their use in crop protection for the control of harmful microorganisms, in particular for phytopathogenic fungi.

二唑衍生物可用作為對抗或預防微生物感染之作物保護劑。例如，WO-2019/122323、WO-2018/118781和WO-2018/080859揭示1,2,4-

二唑-3-基嘧啶及1,2,4-

二唑-3-基吡啶衍生物，彼等可用於控制植物上的微生物害蟲，特別為真菌害蟲。殺真菌活性的1,2,4-

二唑係自US 2018/317490和WO-2018/015447進一步得知。WO2020127974和WO-00/15637中揭示一些具有殺真菌活性的1,3,4-

二唑。 Already familiar with 1,2,4-

The oxadiazole derivatives are useful as crop protection agents against or preventing microbial infections. For example, WO-2019/122323, WO-2018/118781 and WO-2018/080859 disclose 1,2,4-

oxadiazol-3-ylpyrimidine and 1,2,4-

Diazol-3-ylpyridine derivatives, which are useful for controlling microbial pests, especially fungal pests, on plants. Fungicidal activity of 1,2,4-

The oxadiazoles are further known from US 2018/317490 and WO-2018/015447. WO2020127974 and WO-00/15637 disclose some 1,3,4-

oxadiazole.

二唑衍生物很少見且不常用於控制微生物害蟲。WO-2018/165520、WO-2017/065473和WO-2017/023133揭示1,3,4-

二唑-2-基嘧啶及1,3,4-

二唑-2-基吡啶衍生物，彼等可用作為治療人類疾病之金屬酶(組蛋白去乙醯酶)抑制劑。 1,3,4-

Diazole derivatives are rare and infrequently used to control microbial pests. WO-2018/165520, WO-2017/065473 and WO-2017/023133 disclose 1,3,4-

oxadiazol-2-ylpyrimidine and 1,3,4-

Diazol-2-ylpyridine derivatives, which are useful as metalloenzyme (histone deacetylase) inhibitors for the treatment of human diseases.

Many fungicides have been developed to date. However, there is still a need to develop novel fungicidal compounds themselves that provide efficacy against a broad spectrum of fungi, have lower toxicity, higher selectivity, and Compounds that are used at lower dosage rates to reduce or avoid adverse environmental or toxicological effects while still allowing effective pest control. It may also be desirable to have novel compounds that prevent the emergence of fungicide resistance. In addition, it may be desirable to provide other fungicidal compounds with improved storage stability and/or higher weathering stability, eg, improved photostability.

The present invention provides novel fungicidal compounds that, in at least some of these aspects, outperform known compounds and compositions.

The present invention relates to compounds of formula (I) as defined herein:

wherein R1, ^R2 , ^R3 and X are as described herein, as well as salts, N ^- oxides and solvates thereof.

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

The present invention also relates to the use of a compound of formula (I) as defined herein or a composition as defined herein for the control of harmful microorganisms, in particular for phytopathogenic fungi, in crop protection.

The present invention also relates to a method for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection, which comprises applying at least one compound of formula (I) as defined herein or a composition as defined herein steps to harmful microorganisms and/or their habitats.

The present invention also relates to processes and intermediates for the preparation of compounds of formula (I).

definition

Unless otherwise stated, the following definitions apply to substituents and residues used throughout this specification and claimed scope:

The term "halogen" as used herein refers to a fluorine, chlorine, bromine or iodine atom.

The term "pendant oxy" as used herein refers to an oxygen atom bonded to a carbon or sulfur atom via a double bond.

The term "C1-C8-alkyl" as used herein refers to a saturated branched or straight hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms. Examples of C1-C8-alkyl include, but are not limited to, methyl, ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl (n-butyl), 1-methyl Propyl (secondary butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tertiary butyl), pentyl, 1-methylbutyl, 2-methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 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, tertiary butyl, isobutyl or tertiary butyl.

_The term "C2 _- C8-alkenyl" as used herein refers to an unsaturated branched or straight hydrocarbon chain having 2, 3, 4, 5, 6, 7 or 8 carbon atoms and containing at least one double bond. Examples of C2 _- C8-alkenyl groups include, but are not limited to, ethenyl (or "vinyl"), prop- ₂ -en-1-yl (or "allyl"), prop-2-en-l-yl (or "allyl"), prop- 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, prop-1-en-2- (or "isoenyl"), 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methylprop-1-enyl, 1-methylprop-1 -Alkenyl, 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- Alkenyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpentan-4 -Alkenyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methylpent-4-enyl, 4-methylpent-3-enyl, 3- Methylpent-3-enyl, 2-methylpent-3-enyl, 1-methylpent-3-enyl, 4-methylpent-2-enyl, 3-methylpent-2- Alkenyl, 2-methylpent-2-enyl, 1-methylpent-2-enyl, 4-methylpent-1-enyl, 3-methylpent-1-enyl, 2-methyl ylpent-1-enyl, 1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-ene base, 3-ethylbut-2-enyl, 2-ethylbut-2-enyl, 1-ethylbut-2-enyl, 3-ethylbut-1-enyl, 2-ethyl But-1-enyl, 1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-ene base, 1-isopropylprop-2-enyl, 2-propylprop-1-enyl, 1-propylprop-1-enyl, 2-isopropylprop-1-enyl, 1- Isopropylprop-1-enyl, 3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)vinyl, but-1,3-dienyl, Pent-1,4-dienyl, hex-1,5-dienyl or methylhexadienyl.

_The term "C2 _- C8-alkynyl" as used herein refers to a branched or straight chain hydrocarbon having 2, 3, 4, 5, 6, 7 or 8 carbon atoms and containing at least one double bond. Examples of C2 _- C8-alkynyl groups include, but are not limited to, ethynyl, prop- ₁ -ynyl, prop-2-ynyl (or "propargyl"), but-1-ynyl, but-2- Alkynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl base, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbutanyl -3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methyl-pent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpentanyl -2-ynyl, 1-methyl-pent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl , 1-ethylbut-3-ynyl, 1-ethylbut-2-ynyl, 1-propylprop-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 base.

The term "C ₁ -C ₈ -haloalkyl" as used herein refers to a C ₁ -C ₈ -alkyl group as defined above wherein one or more hydrogen atoms are replaced by halogen atoms which may be the same or different. Typically, _{a C1} -C8-haloalkyl group contains up to ₉ halogen atoms, which may be the same or different. "C ₁ -C ₈ -haloalkyl having 1 to 5 halogen atoms" as used herein refers to a C ₁ -C 8 -haloalkyl group as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different _C8 -alkyl.

_The term "C2 _- C8-haloalkenyl" as used herein refers to a C2 _{- C8} as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different -Alkenyl. Typically, a C2 _- C8-haloalkenyl group contains up to ₉ halogen atoms which may be the same or different.

_The term "C2 _- C8-haloalkynyl" as used herein refers to a C2 _{- C8} as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different -Alkynyl. Typically, up to 9 halogen atoms, which may be the same or different, are included.

The term "C ₁ -C ₄ -hydroxyalkyl" as used herein refers to a C ₁ -C ₄ -alkyl group as defined above wherein at least one hydrogen atom is replaced by a hydroxy group. Examples of _C1 - _C4 -hydroxyalkyl include, but are not limited to, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl , 1-hydroxypropyl, 1-hydroxypropan-2-yl, 2-hydroxypropan-2-yl, 2,3-dihydroxypropyl and 1,3-dihydroxypropan-2-yl.

The term "C ₁ -C ₈ -cyanoalkyl" as used herein refers to a C ₁ -C ₈ -alkyl group as defined above wherein at least one hydrogen atom is replaced by a cyano group.

The term "C ₁ -C ₈ -alkoxy" as used herein refers to a group of formula (C ₁ -C ₈ -alkyl)-O-, wherein the term "C ₁ -C ₈ -alkyl" is as used herein defined. Examples of _C1 -C8-alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, ₁ -methylethoxy, n-butoxy, 1-methylpropoxy, 2 -Methylpropoxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2 -Dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 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.

The term "C ₁ -C ₈ -haloalkoxy" as used herein refers to a C ₁ -C ₈ -alkoxy as defined above wherein one or more hydrogen atoms are replaced by halogen atoms which may be the same or different base. The term "C ₁ -C ₈ -haloalkoxy having 1 to 5 halogen atoms" as used herein refers to C as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different ₁ - _C8 -alkoxy. Examples of _C1 - _C8 -haloalkoxy include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy Fluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy oxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-Dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy.

The term "C ₁ -C ₈ -alkylthio" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-S-, wherein the term "C ₁ -C ₈ - "Alkyl" is as defined herein. Examples of _C1 - _C8 -alkylthio groups include, but are not limited to, methylthio, ethylthio, propylthio, isopropylthio, butylthio, secondary-butylthio, isobutylthio, tertiary-butyl Thio, pentylthio, isopentylthio, hexylthio.

The term " _C1 -C8-haloalkylthio having 1 to ₅ halogen atoms" as used herein means as defined above wherein 1 to 5 hydrogen atoms are replaced by halogen atoms which may be the same or different C ₁ -C ₈ -Alkylthio.

The term "C ₁ -C ₈ -alkylsulfinyl" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-S(=O)-, wherein the term "C ₁ -C ₈ -Alkyl" is as defined herein. Examples of _C1 -C8-alkylsulfinyl groups include, but are not limited to, saturated straight or branched chain alkanes having 1 to ₈ , preferably 1 to 6, and more preferably 1 to 4 carbon atoms Ethylsulfinyl, such as (but not limited to) methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl , 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutyl Sulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl base, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methyl Pentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethyl butylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl sulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

The term " _C1 -C8-haloalkylsulfinyl having 1 to ₅ halogen atoms" as used herein refers to as described above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different _C1 -C8- _{Alkylsulfinyl} as defined.

The term "C ₁ -C ₈ -alkylsulfonyl" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-S(=O) ₂ - wherein the term "C ₁ -C ₈ -Alkyl" is as defined herein. Examples of C ₁ -C ₈ -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-dimethyl Propylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl Sulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl Sulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl sulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methyl propylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

The term " _C1 -C8-haloalkylsulfonyl having 1 to ₅ halogen atoms" as used herein means as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different The C ₁ -C ₈ -alkylsulfonyl group.

The term "C ₁ -C ₈ -alkylsulfonamido" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-S(=O) ₂ -NH- , wherein the term "C ₁ -C ₈ -alkyl" is as defined herein.

The term " _C1 -C8-haloalkylsulfonamido having 1 to ₅ halogen atoms" as used herein refers to as described above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different _C1 - _C8 -alkylsulfonamido as defined.

The term "arylsulfonamido" as used herein refers to a group of formula aryl-S(=O) ₂ -NH-, wherein the term "aryl" is as defined herein.

The term "C ₁ -C ₈ -alkylaminosulfonyl" as used herein refers to a sulfamoyl group having one C ₁ -C ₈ -alkyl group as defined herein.

The term "di-(C ₁ -C ₈ -alkyl)sulfamoyl" as used herein refers to a sulfamoyl group having two independently selected from C ₁ -C ₈ -alkyl groups as defined herein.

The term "C ₁ -C ₈ -alkylaminocarbamoyl" as used herein refers to an carbamoyl group having one C ₁ -C ₈ -alkyl group as defined herein.

The term "di-(C ₁ -C ₈ -alkyl)aminocarbamoyl" as used herein refers to a sulfamoyl group having two independently selected from C ₁ -C ₈ -alkyl groups as defined herein.

The term "C ₁ -C ₈ -alkylcarbonyl" as used herein refers to a saturated straight or branched group of formula (C ₁ -C ₈ -alkyl)-C(=O)-, wherein the term "C ₁ - _C8 -Alkyl" is as defined herein.

The term "C ₁ -C ₈ -haloalkanecarbonyl having 1 to 5 halogen atoms" as used herein refers to C ₁ as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different _-C8 -Alkylcarbonyl.

The term "C ₁ -C ₈ -alkcarbonyloxy" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-C(=O)-O-, wherein the term "C ₁ -C ₈ -Alkyl" is as defined herein.

The term "C ₁ -C ₈ -haloalkcarbonyloxy having 1 to 5 halogen atoms" as used herein means as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different C ₁ -C ₈ -alkanecarbonyloxy.

The term "C ₁ -C ₈ -alkanecarbonylamino" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkyl)-C(=O)-NH-, wherein the term "C ₁ -C ₈ -alkyl" is as defined herein.

The term "C ₁ -C ₈ -haloalkanecarbonylamino having 1 to 5 halogen atoms" as used herein means as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different C ₁ -C ₈ -alkanecarbonylamino.

The term "C ₁ -C ₈ -alkoxycarbonylamino" as used herein refers to a saturated straight or branched group of formula (C ₁ -C ₈ -alkoxy)-C(=O)-NH-, wherein the term "C ₁ -C ₈ -alkoxy" is as defined herein.

The term "C ₁ -C ₈ -haloalkoxycarbonylamino having 1 to 5 halogen atoms" as used herein means as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different The C ₁ -C ₈ -alkoxycarbonylamino group.

The term "C ₁ -C ₈ -alkoxycarbonyl" as used herein refers to a saturated straight or branched chain group of formula (C ₁ -C ₈ -alkoxy)-C(=O)-, wherein the term "C ₁ - _C8 -Alkoxy" is as defined herein.

The term "C ₁ -C ₈ -haloalkoxycarbonyl having 1 to 5 halogen atoms" as used herein refers to C as defined above wherein one to five hydrogen atoms are replaced by halogen atoms which may be the same or different ₁ - _C8 -alkoxycarbonyl.

The term "C ₁ -C ₈ -alkylamino" as used herein refers to an amine group having one C ₁ -C ₈ -alkyl group as defined herein. Examples of _C1 - _C8 -alkylamino groups include, but are not limited to, N-methylamino, N-ethylamino, N-isopropylamino, N-n-propylamino, N-isopropylamino, and N-tertiary butylamino amine group.

The term "di-(C ₁ -C ₈ -alkyl)amine group" as used herein refers to an amine group having two independently selected from C ₁ -C ₈ -alkyl groups as defined herein. Examples of di-(C ₁ -C ₈ -alkyl)amino groups include, but are not limited to, N,N-dimethylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethylamino N-methylamino, N-methyl-N-n-propylamino, N-isopropyl-N-n-propylamino and N-tert-butyl-N-methylamino.

The term "N-(C ₁ -C ₈ -alkyl)-N-(C ₃ -C ₇ -cycloalkyl)amino" as used herein means having a C ₁ -C ₈ -alkane as defined herein group and an N,N-disubstituted amino group of a C3 _- C7 _- cycloalkyl group as defined herein.

_The term "non-aromatic C3 _- C12-carbocycle" or "C3 _{- C12} -carbocycle" as used herein refers to a non-aromatic saturated or partially unsaturated hydrocarbon ring system in which all ring members (which are 3 to 12) are all carbon atoms. The ring system can be monocyclic or polycyclic (fused, spiro or bridged). "Non-aromatic C ₃ -C ₁₂ -carbocycle" includes, but is not limited to, C ₃ -C ₁₂ -cycloalkyl (mono or bicyclic), C ₃ -C ₁₂ -cycloalkenyl (mono or bicyclic), including and monocyclic Bicyclic systems (eg tetrahydronaphthyl, indanyl ₎ of cyclic C3-C7-cycloalkyl-fused aryl (eg phenyl), including fused to monocyclic C3 _{- C8 -} cycloalkenyl aryl (e.g. phenyl) bicyclic ring systems (e.g. indenyl, dihydronaphthyl) and tricyclic systems comprising cyclopropyl linked through a carbon atom to a bicyclic ring system comprising a monocyclic _C3- C7 _- cycloalkyl or monocyclic C3 _{- C8} -cycloalkenyl fused aryl (eg phenyl). _The non-aromatic C3 _- C12-carbocycle can be attached to the parent molecular moiety through any carbon atom.

The term "C3 _- C12-cycloalkyl" as used herein refers to a saturated monovalent mono- or bicyclic hydrocarbon ring containing 3, 4, 5, 6, 7, 8, 9, 10, ₁₁ or 12 carbon atoms. "C3 _- C7 _- cycloalkyl" as used herein designates monocyclic C3 _- C7 _- cycloalkyl, which includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. "C3 _{- C5} -cycloalkyl" as used herein designates monocyclic C3 _{- C5} -cycloalkyl, which includes cyclopropyl, cyclobutyl, and cyclopentyl. Examples of bicyclo _C6 - _Ci2 -cycloalkyl include, but are not limited to, bicyclo[3.1.1]heptane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, bicyclo[3.2.2]nonane Alkane, bicyclo[3.3.1]nonane, bicyclo[4.2.0]octyl, octahydrocyclopentadienyl and bicyclo[4.2.1]nonane.

The term "C3 _- C7-halocycloalkyl having 1 to ₅ halogen atoms" as used herein means as defined above wherein 1 to 5 hydrogen atoms are replaced by halogen atoms which may be the same or different C3 _- C7 _- cycloalkyl.

The term "C3 _- C7 _- cycloalkylthio" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-S-, wherein the term "C3 _- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkylsulfinyl" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-S(=O) _- , wherein the term "C3- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkylsulfonyl" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-S( ₌ O) _2- , wherein the term "C3- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkylaminocarbamoyl" as used herein refers to an aminocarbamoyl group having one C3 _- C7 _- cycloalkyl as defined herein.

The term "N-(C ₁ -C ₈ -alkyl)-N-(C ₃ -C ₇ -cycloalkyl)carbamoyl" as used herein means having a C ₁ -C ₈ as defined herein - alkyl and an N,N-disubstituted amine carboxyl group of C3 _- C7 _- cycloalkyl as defined herein.

The term "C3 _- C7 _- cycloalkylamino" as used herein refers to a (C3 _- C7 _- cycloalkyl)-NH- group, wherein the term "C3 _- C7 _- cycloalkyl" is as as defined herein.

The term "C3 _- C7 _- cycloalkanecarbonyl" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-C(=O)-, wherein the term "C3 _- C7 _- cycloalkyl""Alkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkanecarbonyloxy" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-C( ₌ O)-O-, wherein the term "C3- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkanecarbonylamino" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-C( ₌ O)-NH-, wherein the term "C3- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkoxycarbonylamino" as used herein refers to a group of formula (C3 _- C7 _- cycloalkoxy)-C(=O)-NH-, wherein the term "C ₃ -C7 _- cycloalkoxy" is as defined herein.

The term "C3 _- C7 _- cycloalkylsulfonamido" as used herein refers to a group of formula (C3 _- C7 _- cycloalkyl)-S(=O) ₂ -NH-, wherein the term " C3 _- C7 _- cycloalkyl" is as defined herein.

The term "C3 _- C7 _- cycloalkylsulfamoyl" as used herein refers to a sulfamoyl group having one C3 _- C7 _- cycloalkyl as defined herein.

The term "aromatic _C6 - _C14 -carbocycle" or "aryl" as used herein refers to an aromatic hydrocarbon ring system in which all ring members (which vary from 6 to 14, preferably 6 to 10) ) are all carbon atoms. The ring system can be monocyclic or fused polycyclic (eg, bicyclic or tricyclic). Examples of aryl groups include, but are not limited to, phenyl, azulenyl, naphthyl, and intenyl. An aryl group can be attached to the parent molecular moiety through any carbon atom. It is further understood that when the aryl group is substituted with one or more substituents, the substituent(s) may be at any position on the aryl ring(s). In particular, where the aryl group is phenyl, the substituent(s) may occupy one or two ortho positions, one or two meta positions, or para positions, or any combination of these positions.

The term "non-aromatic 3- to 10-membered heterocycle" or "heterocyclyl" as used herein refers to a ring containing 1 to 4 or 1 to 3 independently selected from the group consisting of oxygen, nitrogen and sulfur. Non-aromatic, saturated or partially unsaturated non-aromatic ring systems of heteroatoms. If the ring system contains more than one oxygen atom, they are not directly adjacent. Non-aromatic heterocycles include, but are not limited to, 3- to 7-membered monocyclic non-aromatic heterocycles and 6- to 10-membered polycyclic (eg, bicyclic or tricyclic) non-aromatic heterocycles. The non-aromatic 3- to 10-membered heterocycle can be attached to the parent molecular moiety through any carbon or nitrogen atom contained within the heterocycle.

基、氮

基)、4-員環(諸如氮呾基、氧呾基、硫呾基)、5-員環(諸如四氫呋喃基、1,3-二氧戊環基、四氫噻吩基、吡咯啶基、吡唑啶基、咪唑啶基、三唑啶基、異

唑啶基、

唑啶基、

二唑啶基、噻唑啶基、異噻唑啶基、噻二唑啶基)、6-員環(諸如哌啶基、六氫嗒

基、六氫嘧啶基、哌

基、三

烷基(triazinanyl)、六氫三

基、四氫哌喃基、二

烷基、四氫噻喃基、二噻烷基、嗎啉基、1,2-氧氮

基(oxazinanyl)、氧硫

基(oxathianyl)、硫代嗎啉基)或7-員環(諸如氧

基(oxepanyl)、氮

基(azepanyl)、1,4-二氮

基和1,4-氧氮

基(oxazepanyl))。不飽和非芳族雜環之實例包括但不限於5-員環(諸如二氫呋喃基、1,3-二氧雜環戊烯基(dioxolyl)、二氫噻吩基、吡咯啉基、二氫咪唑基、二氫吡唑基、異

唑啉基、二氫

唑基、二氫噻唑基)或6員環(諸如哌喃基、噻喃基、噻

基和噻二

基)。 The term "non-aromatic 3- to 7-membered monocyclic heterocycle" as used herein refers to a 3-, 4-, 4-, 3-, 4-, 3-, 4-, 3-, 4-, 3-, 4-, A 5-, 6- or 7-membered monocyclic ring system, wherein the ring system is saturated or unsaturated, but not aromatic. For example, the heterocycle may contain one to three nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and one oxygen atom, or one to three nitrogen atoms and sulfur atoms, or A sulfur atom and an oxygen atom. Examples of saturated non-aromatic heterocycles include, but are not limited to, 3-membered rings (such as oxygen

base, nitrogen

base), 4-membered rings (such as nitrogen, oxo, thio), 5-membered rings (such as tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, Pyrazolidinyl, imidazolidinyl, triazolidinyl, iso

oxazolidinyl,

oxazolidinyl,

oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl), 6-membered rings (such as piperidinyl, hexahydropyridine)

base, hexahydropyrimidinyl, piperidine

base, three

Alkyl (triazinanyl), hexahydrotris

base, tetrahydropyranyl, two

Alkyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxonitrogen

base (oxazinanyl), oxygen sulfur

oxathianyl, thiomorpholinyl) or a 7-membered ring (such as oxygen

base (oxepanyl), nitrogen

azepanyl, 1,4-diazo

base and 1,4-oxonitrogen

base (oxazepanyl). Examples of unsaturated non-aromatic heterocycles include, but are not limited to, 5-membered rings such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrroline, dihydro Imidazolyl, dihydropyrazolyl, iso

oxazolinyl, dihydro

oxazolyl, dihydrothiazolyl) or 6-membered ring (such as piperanyl, thiopyranyl, thi

base and thiadiene

base).

The term "non-aromatic 6- to 10-membered polycyclic heterocycle" as used herein refers to a 6-, 7-, and 7-membered heteroatom containing 1, 2, or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. -, 8-, 9-, 10-membered polycyclic (eg bicyclic or tricyclic) ring systems, wherein the ring system is saturated or unsaturated, but not aromatic. The non-aromatic bicyclic heterocycle may be _composed of a monocyclic heterocycle as defined herein fused to a monocyclic C3 _- C7-cycloalkyl, monocyclic C3 _- C8 _- cycloalkenyl or monocyclic non-aromatic heterocycle Consisting of aryl, or may be fused with aryl (eg phenyl), monocyclic C3 _- C7-cycloalkyl, monocyclic C3 _{- C8 -} cycloalkenyl, or monocyclic non-aromatic heterocycle Monocyclic non-aromatic heterocycles. When two monocyclic heterocycles (aromatic or non-aromatic) containing a nitrogen atom are fused, the nitrogen atom may be located at a bridging head (eg 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). The non-aromatic tricyclic heterocycle can be composed of a monocyclic cycloalkyl group attached to the non-aromatic bicyclic heterocycle through a common atom.

The term "aromatic 5- to 14-membered heterocycle" or "heteroaryl" as used herein refers to an aromatic ring containing 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur system. If the ring system contains more than one oxygen atom, they are not directly adjacent. Aromatic heterocycles include aromatic 5- or 6-membered monocyclic heterocycles and 6- to 14-membered polycyclic (eg, bicyclic or tricyclic) aromatic heterocycles. The 5- to 14-membered aromatic heterocycle can be attached to the parent molecular moiety through any carbon or nitrogen atom contained within the heterocycle.

唑基、

唑基、

二唑基、

三唑基、異噻唑基、噻唑基、噻二唑基和噻三唑基。6-員單環雜芳基之實例包括但不限於吡啶基、嗒

基、嘧啶基、吡

基、三

基、四

基。 The term "aromatic 5- or 6-membered monocyclic heterocycle" or "monocyclic heteroaryl" as used herein refers to a group containing 1, 2, 3 or 4 atoms independently selected from the group consisting of oxygen, nitrogen and sulfur A 5- or 6-membered monocyclic ring system of heteroatoms of the group. Examples of 5-membered monocyclic heteroaryl groups include, but are not limited to, furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, iso

azolyl,

azolyl,

oxadiazolyl,

Triazolyl, isothiazolyl, thiazolyl, thiadiazolyl and thitriazolyl. Examples of 6-membered monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyridyl

base, pyrimidinyl, pyridine

base, three

base, four

base.

唑基和苯并異

唑基)或10-員環(諸如喹啉基、異喹啉基、

啉基、喹唑啉基、喹

啉基、酞

基、

啶基、喋啶基和苯并二氧雜環己烯基)。在包含兩個稠合的5-或6-員單環芳族雜環的9-或10-員芳族雙環雜環中，氮原子可位於橋聯頭(例如咪唑并[1,2-a]吡啶基、[1,2,4]三唑并[4,3-a]吡啶基、咪唑并 [1,2-a]吡啶基、咪唑并[2,1-b]

唑基、呋喃并[2,3-d]異

唑基)。三環芳族雜環之實例包括但不限於咔唑基、吖啶基和啡

基。 The term "6- to 14-membered polycyclic aromatic heterocycle" or "polycyclic heteroaryl" as used herein refers to a compound containing 1, 2 or 3 atoms independently selected from the group consisting of oxygen, nitrogen and sulfur. 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered polycyclic (eg bicyclic or tricyclic) ring systems of heteroatoms. Aromatic bicyclic heterocycles may consist of a monocyclic heteroaryl group, as defined herein, fused to an aryl group (eg, phenyl) or a monocyclic heteroaryl group. Examples of bicyclic aromatic heterocycles include, but are not limited to, 9-membered rings such as indolyl, indazolyl, isoindolyl, benzimadozolyl, imidazopyridyl, indazolyl, benzotriyl oxazolyl, purinyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoyl

azolyl and benziso

azolyl) or a 10-membered ring (such as quinolyl, isoquinolyl,

Linyl, quinazolinyl, quinoline

Lino, phthalo

base,

pyridyl, pteridyl, and benzodioxenyl). In a 9- or 10-membered aromatic bicyclic heterocycle comprising two fused 5- or 6-membered monocyclic aromatic heterocycles, the nitrogen atom may be located at a bridge head (eg imidazo[1,2-a ]pyridyl, [1,2,4]triazolo[4,3-a]pyridyl, imidazo[1,2-a]pyridyl, imidazo[2,1-b]

azolyl, furo[2,3-d]iso

azolyl). Examples of tricyclic aromatic heterocycles include, but are not limited to, carbazolyl, acridine, and phenanthrene

base.

The term "C3 _- C7 _- cycloalkoxy" as used herein designates a group of formula -OR wherein R is C3 _- C7 _- cycloalkyl as defined herein.

Terms " _-C1 - _C8 -alkyl-aryl", " _-C1 - _C8 -alkyl-heterocyclyl", " _-C1 - _C8 -alkyl-heteroaryl" and "-C1-C8-alkyl-heteroaryl" C ₁ -C ₈ -alkyl-C ₃ -C ₇ -cycloalkyl" as used herein designates a group of formula "-C ₁ -C ₈ -alkyl-R", wherein R is each as defined herein Aryl, heterocyclyl, heteroaryl or C3 _- C7-cycloalkyl, " _C1 -C8 _- alkyl" is one having 1, 2, 3, 4, 5, 6, 7 or ₈ carbons A saturated branched or straight chain hydrocarbon of atoms and wherein the group " _-C1 - _C8 -alkyl-R" is attached to the parent moiety via " _C1 - _C8 -alkyl".

As used herein, when a group is referred to as being "substituted," the group can be substituted with one or more substituents. The phrase "one or more substituents" refers to the number of substituents ranging from one to the maximum number of possible substituents depending on the number of available bonding positions, subject to conditions of stability and chemical feasibility.

The term "leaving group" as used herein should be understood to mean a group displaced from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("trifluoromethanesulfonate") group, an alkoxy group , methanesulfonate, p-toluenesulfonate, etc.

When referring to a variable xxxx, the term "as described herein" incorporates by reference a broad definition of the variable as well as preferred, better and even better definitions, if any.

The present invention relates to compounds of formula (I):

in

X is hydrogen or fluorine;

R ¹ and R ² together with the carbon atom to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one or more R ^1b substituents;

^R is aryl or heteroaryl, wherein the aryl and heteroaryl may be substituted with one or more R ^substituents ;

R ^1b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl group) sulfamoyl; and/or

The two geminal R ^1b substituents may together with the carbon atom to which they are attached form a C ₃ -C ₇ -cycloalkyl or 3- to 7-membered heterocyclyl, or

The two twin R ^1b substituents may together with the carbon atom to which they are attached form a C=O, C=CH ₂ or C=NO-(C ₁ -C ₈ -alkyl) group;

R ^3b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl; C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl wherein the C ₁ -C ₈ -alkyl group may be substituted with one or more R ^x substituents;

R ^x is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amine, thiol, pentafluoro-λ ⁶ -thiol, carboxyl, carbamoyl, Carbamates, C ₃ -C ₇ -cycloalkyl, C ₃ -C ₇ -halocycloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -alkylamino, N-(C ₁ - C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl with 1 to 5 halogen atoms, C ₁ -C with 1 to 5 halogen atoms ₈ -Haloalkanecarbonyl, C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylaminecarboxyl, C ₃ -C ₇ -cycloalkylaminecarboxyl, N-(C ₁ -C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl) carbamoyl, di-(C ₁ -C ₈ -alkyl) carbamoyl, C ₁ -C ₈ -alkoxycarbonyl , C ₁ -C ₈ -haloalkoxycarbonyl with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 halogen atoms C ₁ -C ₈ -haloalkanecarbonyloxy, C ₃ -C ₇ -cycloalkanecarbonyloxy, C ₁ -C ₈ -alkanecarbonylamino, C ₁ -C ₈ -haloalkanes with 1 to 5 halogen atoms Carbonylamino, C3-C7-cycloalkanecarbonylamino, _{C1 -} C8 _- alkoxycarbonylamino, C1- _C8 -haloalkoxycarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C7-cycloalkoxycarbonylamino, _{C1 -} C8-alkylsulfinyl, C1 _{- C8} -haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3- C ₇ -cycloalkylsulfinyl, C 1 -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms _{; C 3 -C 7} - Cycloalkylsulfonamido, _C1 -C8-alkylsulfonamido, C1 _{- C8 -} haloalkylsulfonamido with ₁ to ₅ halogen atoms, C3-C7-cycloalkane sulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfamoyl and di-(C ₁ -C ₈ -alkyl) sulfamoyl;

and their salts, N-oxides or solvates.

Compounds that result from combinations that violate the laws of nature and that those skilled in the art would therefore be able to exclude based on their expertise are not included herein. For example: ring structures with three or more adjacent oxygen atoms are excluded. Compounds of combinations that arise against the laws of nature and which a person skilled in the art would therefore be able to exclude based on his/her expertise are not included herein. For example, ring structures having three or more adjacent oxygen atoms are excluded.

According to the invention, the compounds of the formula (I) can be used in crop protection for the control of harmful microorganisms, in particular phytopathogenic fungi. Preferably, the phytopathogenic fungi are selected from the group consisting of: Puccinia species, such as Puccinia recondita, Puccinia graminis or Puccinia striatus Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus; and rust pathogens, in particular selected from the group consisting of Gymnosporangium species, For example, Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; and Phakopsora species, such as Phakopsora pachyrhizi Or Phakopsora meibomiae. Particularly preferred are rust pathogens, in particular P. pachyrhizi and P. pachyrhizi.

The compounds of formula (I) may suitably be in their free form, salt form, N-oxide form or solvate form (eg hydrate).

Depending on the nature of the substituents, the compounds of formula (I) may exist in different stereoisomeric forms. Such stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the present invention includes both pure stereoisomers and any mixtures of such isomers. Where a compound may exist in equilibrium in two or more tautomeric forms, reference to a compound using a specification of one tautomeric form should be considered to include all tautomeric forms.

For example, in which R1 and R2 are taken together with the carbon atom to which they are attached to form a cyclobutyl ring, which is substituted with ^{one R1b} substituent or with ^two different ^R1b substituents (for distinction, labeled herein as In embodiments in which R ^1b and R ^1b' ) are substituted, compounds of formula (I) may exist in the form of enantiomers (I') and/or in the form of enantiomers (I"):

Any of the compounds of the present invention may also exist as one or more geometric isomers depending on the number of double bonds in the compound. Geometric isomers can exist in cis (= Z- ) or trans (= E- ) forms depending on the nature of the double bond or ring substituents. The present invention thus equally relates to all geometric isomers and all possible mixtures in all ratios.

Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of free compounds and/or salts thereof, such as agrochemically active salts.

Agrochemically active salts include acid addition salts of inorganic and organic acids, and salts of customary 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, and acid salts (such as sodium bisulfate and potassium bisulfate). Organic acids that can be used include, for example, formic, carbonic, and alkanoic acids (such as acetic, trifluoroacetic, trichloroacetic, and propionic acids), as well as glycolic, thiocyanic, lactic, succinic, citric, benzoic, cinnamic acids , oxalic acid, saturated or mono- or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkyl sulfonic acids (sulfonic acids of straight or branched chain alkyl groups having 1 to 20 carbon atoms) , arylsulfonic acids or aryldisulfonic acids (aromatic groups with one or two sulfonic acid groups, such as phenyl and naphthyl), alkylphosphonic acids (straight chain with 1 to 20 carbon atoms or branched alkyl phosphonic acids), aryl phosphonic acids or aryl diphosphonic acids (aromatic groups with one or two phosphonic acid groups, such as phenyl and naphthyl), where alkyl and aryl may have other substituents, such as Such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, and the like.

The compounds of the present invention may exist in various crystalline and/or amorphous forms. Crystalline forms include unsolvated crystal forms, solvates and hydrates.

Solvates of compounds of the present invention or their salts are stoichiometric compositions of compound and solvent.

Compounds of formula (I) are referred to herein as "active ingredients".

In the above formula (I), X is preferably hydrogen.

In the above formula (I), R ¹ and R ² together with the carbon atom to which they are attached form a C ₃ -C ₅ -cycloalkyl (cyclopropyl, cyclobutyl or cyclopentyl) ring, wherein the C ₃ - _C5 -cycloalkyl is substituted with one or more (preferably one to three) R ^1b substituents. The R ^1b substituent is preferably selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy, and/or two twin R ^1b substituents together form -O-( A CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group, or two twin R ^1b substituents together with the carbon atom to which they are attached form a C=O group.

In the above formula (I), it is preferred that R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one to three R ^1b substituents.

In some embodiments, in the above formula (I), the C ₃ -C ₅ -cycloalkyl (preferably cyclobutyl or cyclopropyl) is one to three selected from the group consisting of R ^1b substituent substitution: halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkanecarbonyloxy and C ₁ -C ₄ -haloalkcarbonyloxy, more preferably substituted with R ^1b substituents selected from the group consisting of fluorine, hydroxy, methyl, ethyl, Trifluoromethyl, methoxy and acetoxy.

In some other embodiments, in the above formula (I), the C ₃ -C ₅ -cycloalkyl (preferably cyclobutyl or cyclopropyl) is substituted with two Gemini R ^1b substituents, wherein The two twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or the two twin R ^1b substituents and the one to which they are attached The carbon atoms come together to form a C=O group.

In some embodiments, R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one or two R ^1b substituents selected from the group consisting of Substitution: fluoro, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetoxy.

In the above formula (I), R ³ is aryl or heteroaryl, wherein R ³ may be substituted with one or more (preferably one to three) R ^3b substituents. The R ^3b substituent is preferably selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, with 1 to 5 halogens Atoms C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -alkoxycarbonyl having 1 to 5 halogen atoms .

In some embodiments, in formula (I) above, R ³ is aryl, wherein R ³ may be substituted with one or more R ^3b substituents.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、吡

基、吲哚基、異吲哚基、喹啉基和異喹啉基。 In some embodiments, in formula (I) above, R ³ is heteroaryl, wherein R ³ may be substituted with one or more R ^3b substituents. The heteroaryl group is preferably selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

base, indolyl, isoindolyl, quinolinyl and isoquinolinyl.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、吡

基、吲哚基、異吲哚基、喹啉基和異喹啉基；其中該芳基和雜芳基可經一至三個較佳獨立地選自由下列所組成群組之R^3b取代基取代：氟、氯、溴、硝基、氰基、甲基、乙基、異丙基、正丙基、正丁基、異丁基、三級丁基、環丙基、三氟甲基、二氟甲基、甲氧 基、乙氧基、三氟甲氧基、二氟甲氧基、甲氧羰基、乙氧羰基和三級丁氧羰基。 In the above formula (I), R ³ is more preferably an aryl group selected from phenyl and naphthyl; or a heteroaryl group selected from the group consisting of: furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

wherein the aryl and heteroaryl groups may be substituted with one to three R ^substituents preferably independently selected from the group consisting of : Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, di- Fluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

In some embodiments, R ³ is phenyl, wherein the phenyl group may be substituted with one to three R ^3b substituents. Preferably, the R ^3b substituents are independently selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl , isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxy carbonyl and tertiary butoxycarbonyl. In these embodiments, ^R3 is more preferably phenyl, which is unsubstituted or substituted with one or two substituents independently selected from the group consisting of fluoro, chloro, bromo, methyl, and methoxy.

In some embodiments, ^R is selected from phenyl and pyridine, wherein the phenyl and the pyridine may be substituted with one to three R ^substituents preferably independently selected from the group consisting of: fluorine, Chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl , methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl. In these embodiments, ^R3 is more preferably phenyl, which is unsubstituted or substituted with one to three ^R3b substituents independently selected from fluoro, chloro, bromo, nitro, cyano, Nitro, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy group, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl, preferably unsubstituted or with one or two substituents independently selected from the following : Fluorine, chlorine, bromine, methyl and methoxy.

In some embodiments, R ³ is phenyl substituted with one or two fluorine atoms.

In some embodiments (referred to herein as embodiment Ia), the compounds of the invention are compounds of formula (I) or a salt, N-oxide or solvate thereof:

in

X is hydrogen or fluorine,

R ¹ and R ² together with the carbon atoms to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one to three R ^1b substituents, wherein the R The ^lb substituents are each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy, and/or two twin R ^1b substituents can be taken together to form -O-( A CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or two twin R ^1b substituents may together with the carbon atom to which they are attached form a C=O group;

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、吡

基、吲哚基、異吲哚基、喹啉基和異喹啉基； R ³ is phenyl, naphthyl, or heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl ,different

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

base, indolyl, isoindolyl, quinolinyl and isoquinolinyl;

wherein the phenyl, naphthyl or heteroaryl may be substituted with one to three ^R3b substituents independently selected from the group consisting of halogen, nitro, cyano, _C1 - _C4 -alkyl, C3 _{- C6} -Cycloalkyl, C1- _C4 -haloalkyl with 1 to 5 halogen atoms, _{C1 - C4} -alkoxy, _C1 - _C4 -haloalkoxy with 1 to 5 halogen atoms and C ₁ -C ₄ -alkoxycarbonyl.

Preferably, according to embodiment (Ia), X is hydrogen.

Preferably, according to embodiment (Ia), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one to three R ^1b substituents. Preferably, the R ^1b substituent is selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy, and/or two twin R ^1b substituents together form -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or two twin R ^1b substituents together with the carbon atom to which they are attached form C= O group.

In some embodiments according to embodiment (Ia), the R ^1b substituent is selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halo Alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkcarbonyloxy and C ₁ -C ₄ -haloalkcarbonyloxy, more preferably is selected from the group consisting of fluoro, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetoxy.

In some other embodiments according to embodiment (Ia), the two twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group , or two twin R ^1b substituents together with the carbon atom to which they are attached form a C=O group.

In some preferred embodiments according to embodiment (Ia), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl ring, which is one or two selected from the group consisting of Group R ^1b substituent substitution: fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy.

In some other preferred embodiments according to embodiment (Ia), R ¹ and R ² together with the carbon atom to which they are attached form a cyclobutyl ring, which is substituted with one or two R ^1b substituents , wherein the R ^1b substituent is selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy, or two twin R ^1b substituents and The carbon atoms to which they are attached together form a C=O group or two twin R ^1b substituents together form an -O-( _CH2 ) ₂ -O- or -O-( _CH2 ) ₃ -O- group.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、和吡

基。 In some embodiments according to embodiment (Ia), ^R3 is phenyl or a 5- or 6-membered heteroaryl selected from the group consisting of: furyl (furanyl) ), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

pyrimidinyl, pyrimidinyl, and pyridine

base.

In some embodiments according to embodiment (Ia), the phenyl, naphthyl, or heteroaryl may be substituted with one to three R ^substituents independently selected from the group consisting of chloro, bromo, Nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy , ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

In some embodiments according to embodiment (Ia), the phenyl, naphthyl or heteroaryl group is substituted with one or two fluorine atoms.

In some preferred implementations according to implementation (Ia),

X is hydrogen,

R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one to three R ^1b substituents selected from the group consisting of: fluoro, hydroxy, methyl , ethyl, trifluoromethyl, methoxy and acetyloxy, and/or two twin R ^1b substituents together form -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ The -O- group or the two twin R ^1b substituents together with the carbon atom to which they are attached form a C=O group, and

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、吡

基、吲哚基、異吲哚基、喹啉基和異喹啉基；其中該苯基、萘基和雜芳基可經一至三個獨立地選自由下列所組成群組之R^3b取代基取代：氯、溴、硝基、氰基、甲基、乙基、異丙基、正丙基、正丁基、異丁基、三級丁基、環丙基、三氟甲基、二氟甲基、甲氧基、乙氧基、三氟甲氧基、二氟甲氧基、甲氧羰基、乙氧羰基和三級丁氧羰基。 R ³ is phenyl, naphthyl, or heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl ,different

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

indolyl, indolyl, isoindolyl, quinolinyl, and isoquinolinyl; wherein the phenyl, naphthyl, and heteroaryl groups may be substituted with one to three R ^substituents independently selected from the group consisting of Substituted: chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoro Methyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、和吡

基。 In some such preferred embodiments, ^R3 is phenyl or a 5- or 6-membered heteroaryl selected from the group consisting of furyl (furanyl), thienyl , pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

pyrimidinyl, pyrimidinyl, and pyridine

base.

In some such preferred embodiments, R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is one or two selected from the group consisting of R ^1b substituent substitution: fluoro, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetoxy.

In some other such preferred embodiments, R ¹ and R ² together with the carbon atom to which they are attached form a cyclobutyl ring substituted with two twin R ^1b substituents, wherein the two twin R The ^1b substituents are taken together to form -O-( _CH2 ) ₂ -O- or -O-( _CH2 ) ₃ -O- groups, or the two twin R ^1b substituents are taken together with the carbon atom to which they are attached C=O group.

In some embodiments (referred to herein as embodiment lb), the compounds of the present invention are compounds of formula (I) or a salt, N-oxide or solvate thereof:

in

X is hydrogen or fluorine,

R ¹ and R ² together with the carbon atom to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one or more R ^1b substituents;

^R3 is aryl, preferably naphthyl or phenyl, more preferably phenyl, wherein the aryl may be substituted with one or more ^R3b substituents;

R ^1b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl ) sulfamoyl; and/or

The two geminal R ^1b substituents may together with the carbon atom to which they are attached form a C ₃ -C ₇ -cycloalkyl or 3- to 7-membered heterocyclyl, or

The two twin R ^1b substituents may together with the carbon atom to which they are attached form a C=O, C=CH ₂ or C=NO-(C ₁ -C ₈ -alkyl) group;

R ^3b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl; C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl ) sulfamoyl; wherein the C ₁ -C ₈ -alkyl group may be substituted with one or more R ^x substituents;

R ^x is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amine, thiol, pentafluoro-λ ⁶ -thiol, carboxyl, carbamoyl, Carbamates, C ₃ -C ₇ -cycloalkyl, C ₃ -C ₇ -halocycloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -alkylamino, N-(C ₁ - C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl with 1 to 5 halogen atoms, C ₁ -C with 1 to 5 halogen atoms ₈ -Haloalkanecarbonyl, C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylaminecarboxyl, C ₃ -C ₇ -cycloalkylaminecarboxyl, N-(C ₁ -C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl)carbamoyl, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl , C ₁ -C ₈ -haloalkoxycarbonyl with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 halogen atoms C ₁ -C ₈ -haloalkanecarbonyloxy, C ₃ -C ₇ -cycloalkanecarbonyloxy, C ₁ -C ₈ -alkanecarbonylamino, C ₁ -C ₈ -haloalkanes with 1 to 5 halogen atoms Carbonylamino, C3-C7-cycloalkanecarbonylamino, _{C1 -} C8 _- alkoxycarbonylamino, C1- _C8 -haloalkoxycarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C7-cycloalkoxycarbonylamino, _{C1 -} C8-alkylsulfinyl, C1 _{- C8} -haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3- C ₇ -cycloalkylsulfinyl, C 1 -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms _{; C 3 -C 7} - Cycloalkylsulfonamido, _C1 -C8-alkylsulfonamido, C1 _{- C8 -} haloalkylsulfonamido with ₁ to ₅ halogen atoms, C3-C7-cycloalkane sulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfamoyl and di-(C ₁ -C ₈ -alkyl) sulfamoyl.

In some preferred embodiments according to embodiment (Ib), X is hydrogen.

In some preferred embodiments according to embodiment (Ib), R ¹ and R ² together with the carbon atom to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ - Cycloalkyl is substituted with one to three R ^1b substituents, wherein the R ^1b substituent is selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halo Alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy and/or di- The twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or two twin R ^1b substituents together with the carbon atom to which they are attached A C=O group is formed.

In some of these preferred embodiments according to embodiment (Ib), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is selected from one to three Substituted with R ^1b substituents from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy, more preferably substituted with R ^1b substituents selected from the group consisting of fluorine, hydroxy, Methyl, ethyl, trifluoromethyl, methoxy and acetyloxy.

In some other such preferred embodiments according to embodiment (Ib), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with two A twin R ^1b substituent, wherein the two twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or the two twin R ^1b substituents The groups together with the carbon atoms to which they are attached form a C=O group.

In some preferred embodiments according to embodiment (Ib), R ³ is naphthyl or phenyl, preferably phenyl; wherein the naphthyl and phenyl may be independently selected from one to three of the following R ^3b substituent substitution: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 halogen atoms , C ₁ -C ₄ -alkoxy, C _{1 -C 4 -haloalkoxy with 1 to 5 halogen atoms and C 1 -C 4 -alkoxycarbonyl .}

In some particularly preferred embodiments according to embodiment (Ib), R ³ is phenyl, which may be substituted with one to three R ^3b substituents independently selected from the group consisting of: chloro, bromo, nitro , cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, Ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

In some implementations according to implementation (Ib),

X is hydrogen,

R ¹ and R ² together with the carbon atom to which they are attached form a C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one to three selected from the group consisting of Group substitution: halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ - C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy and/or two twin R ^1b substituents together form -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) The ₃ -O- group or the two twin R ^1b substituents together with the carbon atom to which they are attached form a C=O group; and

^R3 is phenyl, which may be substituted with one to three ^R3b substituents independently selected from the group consisting of halogen, nitro, cyano, _C1 - _C4 -alkyl, C3 _{- C6} -Cycloalkyl, C1- _C4 -haloalkyl with 1 to 5 halogen atoms, _{C1 - C4} -alkoxy, _C1 - _C4 -haloalkoxy with 1 to 5 halogen atoms and C ₁ -C ₄ -alkoxycarbonyl.

In some implementations according to implementation (Ib),

X is hydrogen,

R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one to three R ^1b substituents selected from the group consisting of: fluoro, hydroxy, methyl , ethyl, trifluoromethyl, methoxy and acetyloxy, and

^R is phenyl, which may be substituted with one to three R ^substituents independently selected from the group consisting of chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl base, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methyl Oxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

In some embodiments (referred to herein as embodiment Ic), the compounds of the present invention are compounds of formula (I) or a salt, N-oxide or solvate thereof:

in

X is hydrogen or fluorine,

R ¹ and R ² together with the carbon atom to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one or more R ^1b substituents;

R ³ is a heteroaryl group, preferably a 5- or 6-membered heteroaryl group, wherein the heteroaryl group may be substituted with one or more R ^3b substituents;

R ^1b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl ) sulfamoyl; and/or

The two geminal R ^1b substituents may together with the carbon atom to which they are attached form a C ₃ -C ₇ -cycloalkyl or 3- to 7-membered heterocyclyl, or

The two twin R ^1b substituents may together with the carbon atom to which they are attached form a C=O, C=CH ₂ or C=NO-(C ₁ -C ₈ -alkyl) group;

R ^3b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl; C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl ) sulfamoyl; wherein the C ₁ -C ₈ -alkyl group may be substituted with one or more R ^x substituents;

R ^x is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amine, thiol, pentafluoro-λ ⁶ -thiol, carboxyl, carbamoyl, Carbamates, C ₃ -C ₇ -cycloalkyl, C ₃ -C ₇ -halocycloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -alkylamino, N-(C ₁ - C ₈ -alkyl)-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C1-C ₈ -alkyl)amino, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkanecarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms to 5 halogen atoms -Haloalkanecarbonyl, C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylaminocarboxyl, C ₃ -C ₇ -cycloalkylaminocarboxyl, N-(C ₁ -C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl) carbamoyl, di-(C ₁ -C ₈ -alkyl) carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ -haloalkoxycarbonyl with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C with 1 to 5 halogen atoms ₁ -C ₈ -haloalkanecarbonyloxy, C ₃ -C ₇ -cycloalkanecarbonyloxy C ₁ -C ₈ -alkanecarbonylamino, C ₁ -C ₈ -haloalkanecarbonyl with 1 to 5 halogen atoms Amine, C3 _- C7-cycloalkanecarbonylamino, _C1 -C8 _- alkoxycarbonylamino, C1 _{- C8} -haloalkoxycarbonylamino with ₁ to ₅ halogen atoms, C3 -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkylsulfinyl, C ₁ -C ₈ -haloalkylsulfinyl with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -ring Alkylsulfonamido, _C1 -C8-alkylsulfonamido, C1 _{- C8 -} haloalkylsulfonamido with ₁ to ₅ halogen atoms, C3-C7-cycloalkyl Sulfamoyl, sulfamoyl, C ₁ -C ₈ -alkylamidosulfonyl and di-(C ₁ -C ₈ -alkyl)amidosulfonyl.

In some preferred embodiments according to embodiment (Ic), X is hydrogen.

In some preferred embodiments according to embodiment (Ic), R ¹ and R ² together with the carbon atom to which they are attached form C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ - Cycloalkyl is substituted with one to three R ^1b substituents, wherein the R ^1b substituent is selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halo Alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy and/or di- The twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or two twin R ^1b substituents together with the carbon atom to which they are attached A C=O group is formed.

In some of these preferred embodiments according to embodiment (Ic), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is selected from one to three Substituted with R ^1b substituents from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Haloalkoxy, C ₁ -C ₄ -alkanecarbonyloxy and C ₁ -C ₄ -haloalkcarbonyloxy, more preferably substituted with one or two R ^1b substituents selected from the group consisting of : Fluorine, hydroxyl, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy.

In some of these preferred embodiments according to embodiment (Ib), R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is via two twin R ^1b substituent substitution, wherein the two twin R ^1b substituents together form an -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or the two twin R ^1b substituents Together with the carbon atoms to which they are attached, a C=O group is formed.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基、吡

基、吲哚基、異吲哚基、喹啉基和異喹啉基，其中該雜芳基可經一至三個較佳獨立地選自由下列所組成群組之R^3b取代基取代：鹵素、硝基、氰基、C₁-C₄-烷基、C₃-C₆-環烷基、具有1至5個鹵素原子之C₁-C₄-鹵烷基、C₁-C₄-烷氧基、具有1至5個鹵素原子之C₁-C₄-鹵烷氧基和C₁-C₄-烷氧羰基。 In some preferred embodiments according to embodiment (Ic), R ³ is a heteroaryl group selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl , pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

, indolyl, isoindolyl, quinolinyl, and isoquinolinyl, wherein the heteroaryl group may be substituted with one to three R ^substituents preferably independently selected from the group consisting of halogen, Nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C _{1 -C 4 -haloalkyl with 1 to 5 halogen atoms, C 1 -C 4 -alkane} oxy, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -alkoxycarbonyl having 1 to 5 halogen atoms.

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基和吡

基，其中該雜芳基可經一至三個較佳獨立地選自由下列所組成群組之R^3b取代基取代：鹵素、硝基、氰基、C₁-C₄-烷基、C₃-C₆-環烷基、具有1至5個鹵素原子之C₁-C₄-鹵烷基、C₁-C₄-烷氧基、C₁-C₄-鹵烷氧基具有1至5個鹵素原子之和C₁-C₄-烷氧羰基。 In some preferred embodiments according to embodiment (Ic), R ³ is a 5- or 6-membered heteroaryl group preferably selected from the group consisting of: furyl (furanyl )), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

pyrimidinyl, pyrimidinyl and pyridine

wherein the heteroaryl group may be substituted with one to three R ^3b substituents preferably independently selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ - _C6 -cycloalkyl, C1- _C4 -haloalkyl with 1 to 5 halogen atoms, _{C1 - C4} -alkoxy, _C1 - _C4 -haloalkoxy with 1 to 5 The sum of halogen atoms is C ₁ -C ₄ -alkoxycarbonyl.

In some particularly preferred embodiments according to embodiment (Ic), R ³ is pyridyl, which may be substituted with one to three R ^3b substituents independently selected from the group consisting of: chloro, bromo, nitro group, cyano group, methyl group, ethyl group, isopropyl group, n-propyl group, n-butyl group, isobutyl group, tertiary butyl group, cyclopropyl group, trifluoromethyl group, difluoromethyl group, methoxy group, Ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

In some implementations according to implementation (Ic),

X is hydrogen,

R ¹ and R ² together with the carbon atom to which they are attached form a C ₃ -C ₅ -cycloalkyl, wherein the C ₃ -C ₅ -cycloalkyl is substituted with one to three selected from the group consisting of Group substitution: halogen, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ - C ₄ -alkoxy and C ₁ -C ₄ -haloalkcarbonyloxy and/or two twin R ^1b substituents together form -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) The ₃ -O- group or the two twin R ^1b substituents together with the carbon atom to which they are attached form a C=O group; and

唑基、

唑基、

二唑基、異噻唑基、噻唑基、吡啶基、嗒

基、嘧啶基和吡

基，尤佳為吡啶基， R ³ is a 5- or 6-membered heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl ,different

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

pyrimidinyl, pyrimidinyl and pyridine

base, especially pyridyl,

wherein the heteroaryl group may be substituted with one to three R ^3b substituents independently selected from the group consisting of halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cyclic Alkyl, C1- _C4 -haloalkyl having 1 to 5 halogen atoms, _{C1 - C4} -alkoxy, _C1 - _C4 -haloalkoxy having 1 to 5 halogen atoms and C ₁ -C ₄ -alkoxycarbonyl.

In some implementations according to implementation (Ic),

X is hydrogen,

R ¹ and R ² together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl ring, which is substituted with one to three R ^1b substituents selected from the group consisting of: fluoro, hydroxy, methyl , ethyl, trifluoromethyl, methoxy and acetyloxy, and

^R3 is pyridyl, which may be substituted with one to three ^R3b substituents independently selected from the group consisting of chloro, bromo, nitro, cyano, methyl, ethyl, isopropyl, n-propyl base, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methyl Oxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl.

The above preferences for the substituents of the compounds according to the invention can be combined in various ways. The combination of these preferred features thus provides a subclass of compounds according to the invention. Examples of such subclasses of preferred compounds according to the invention are:

- the preferred characteristics of X and one or more preferred characteristics of R ¹ , R ² and R ³ ;

- the preferred characteristics of R ¹ and one or more preferred characteristics of X, R ² and R ³ ;

- the preferred characteristics of R ² and one or more preferred characteristics of X, R ¹ and R ³ ;

- the preferred characteristics of R ³ and one or more preferred characteristics of X, R ¹ and R ² .

Most preferred are compounds of formula (I) selected from the group consisting of:

二唑-2-基]嘧啶-2-胺， N-[3,3-Difluoro-1-(2-fluorophenyl)cyclobutyl]-5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-amine,

二唑-2-基]-N-[3-氟-1-(2-氟苯基)環丁基]嘧啶-2-胺(順式立體異構物)， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-[3-fluoro-1-(2-fluorophenyl)cyclobutyl]pyrimidin-2-amine (cis stereoisomer),

二唑-2-基]-N-[1-(2-氟苯基)-3-甲基-環丁基]嘧啶-2-胺(順式立體異構物)， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-[1-(2-fluorophenyl)-3-methyl-cyclobutyl]pyrimidin-2-amine (cis stereoisomer),

二唑-2-基]嘧啶-2-基]胺基]-3-(2-氟苯基)-環丁醇(反式立體異構物)， 3-[[5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]-3-(2-fluorophenyl)-cyclobutanol (trans stereoisomer),

二唑-2-基]嘧啶-2-基]胺基]-3-(2-氟苯基)環丁基]酯(順式和反式立體異構物)， [3-[[5-[5-(difluoromethyl)-1,3,4-acetic acid

oxadiazol-2-yl]pyrimidin-2-yl]amino]-3-(2-fluorophenyl)cyclobutyl]ester (cis and trans stereoisomers),

二唑-2-基]-N-(3,3-二氟-1-苯基-環丁基)嘧啶-2-胺， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-(3,3-difluoro-1-phenyl-cyclobutyl)pyrimidin-2-amine,

二唑-2-基]-N-[1-(2,6-二氟苯基)-3-氟-環丁基]嘧啶-2-胺(順式和反式立體異構物)， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)-3-fluoro-cyclobutyl]pyrimidin-2-amine (cis and trans stereoisomers),

二唑-2-基]嘧啶-2-胺(順式和反式立體異構物)， N-[1-(4-Bromophenyl)-3-fluoro-cyclobutyl]-5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-amine (cis and trans stereoisomers),

二唑-2-基]嘧啶-2-基]胺基]環丁醇(順式和反式立體異構物)， 3-(2,6-Difluorophenyl)-3-[[5-[5-(trifluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]cyclobutanol (cis and trans stereoisomers),

二唑-2-基]嘧啶-2-基]胺基]-3-苯基-環丁醇(順式和反式立體異構物)， 3-[[5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]-3-phenyl-cyclobutanol (cis and trans stereoisomers),

二唑-2-基]嘧啶-2-基]胺基]環丁醇胺(順式和反式立體異構物)， 3-(4-Chlorophenyl)-3-[[5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]cyclobutanolamine (cis and trans stereoisomers),

二唑-2-基]-N-[1-(2,6-二氟苯基)-3,3-二氟-環丁基]嘧啶-2-胺， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)-3,3-difluoro-cyclobutyl]pyrimidin-2-amine,

二唑-2-基]-N-[rac-(1S,2S)-1-苯基-2-(三氟甲基)環丙基]嘧啶-2-胺(立體異構物的混合物)， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-[rac-(1S,2S)-1-phenyl-2-(trifluoromethyl)cyclopropyl]pyrimidin-2-amine (mixture of stereoisomers),

二唑-2-基]-N-(3-氟-1-苯基-環丁基)嘧啶-2-胺(順式和反式立體異構物)， 5-[5-(Difluoromethyl)-1,3,4-

oxadiazol-2-yl]-N-(3-fluoro-1-phenyl-cyclobutyl)pyrimidin-2-amine (cis and trans stereoisomers),

二唑-2-基]嘧啶-2-胺， N-[2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]-5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-amine,

二唑-2-基]嘧啶-2-基]胺基]-3-(4-氟苯基)環丁醇(順式和反式立體異構物)， 3-[[5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]-3-(4-fluorophenyl)cyclobutanol (cis and trans stereoisomers),

二唑-2-基]-N-[1-(2,6-二氟苯基)-3-甲基-環丁基]嘧啶-2-胺(順式和反式立體異構物)及 5-[5-(Difluoromethyl)-1,3,4-

Diazol-2-yl]-N-[1-(2,6-difluorophenyl)-3-methyl-cyclobutyl]pyrimidin-2-amine (cis and trans stereoisomers) and

二唑-2-基]嘧啶-2-基]胺基]-3-(2,6-二氟苯基)環丁醇(順式和反式立體異構物)， 3-[[5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]pyrimidin-2-yl]amino]-3-(2,6-difluorophenyl)cyclobutanol (cis and trans stereoisomers),

and their salts, N-oxides and solvates.

The compounds of formula (I) are useful in crop protection for the control of harmful microorganisms, in particular phytopathogenic fungi (as fungicides). Accordingly, the present invention relates to the use of compounds of formula (I) in crop protection for the control of phytopathogenic fungi.

The present invention also relates to any of the compounds of formula (I) disclosed in Table 1 .

Intermediates for the preparation of active ingredients

The present invention also relates to intermediates useful in the preparation of compounds of formula (I).

Unless otherwise indicated, groups and designations X, R1, R2 and ^R3 have the meanings given above for compounds of ^formula ( ^I ).

Accordingly, the present invention relates to compounds of formula (II) and their acceptable salts, N-oxides and solvates:

wherein X, R1, R2 and ^R3 have the meanings given above for the compounds of ^formula ( ^I ).

Processes for the preparation of compounds of formula (I) and intermediates

The present invention relates to processes for the preparation of compounds of formula (I) and their intermediates. Unless otherwise indicated, groups and designations X, R1, R2 and ^R3 have the meanings given above for compounds of ^formula ( ^I ). These definitions apply not only to the final products of formula (I), but also to all intermediates.

Compounds of formula (I) can be prepared according to Method P1 by subjecting intermediates of formula (II) to a suitable dehydrating agent such as methyl N-(triethylammoniumsulfonyl)carbamate (Burgess reagent) prepared by reaction in a solvent such as tetrahydrofuran, as previously described in WO2017065473.

方法P1

Method P1

Intermediates of formula (II) are either commercially available or can be prepared according to Method P2 by combining a carbohydrazide of formula (III) with a compound of formula (IVa) or (IVb), either commercially available or available according to known Procedures are prepared starting from readily available compounds) in a suitable solvent such as tetrahydrofuran, optionally in the presence of a base such as triethylamine, preferably at room temperature, as previously described in WO2017065473 said.

Carbohydrazide of formula (III) is commercially available or can be obtained according to method P3 by combining a compound of formula (V) (wherein LG1 is a leaving group such as for example ethoxy) with hydrazine hydrate in a suitable solvent such as ethanol prepared by reaction in WO2017065473 as previously described in WO2017065473.

Compounds of formula (V) may be commercially available or may be prepared according to known procedures starting from readily available compounds.

烷)中以親核性取代進行反應而製備。當LG2為SMe時，可能必需例如藉由3-氯過苯甲酸氧化，以活化脫離基。 Alternatively, compounds of formula (V) can be prepared according to Method P4 by combining compounds of formula (VI) (wherein LG1 is an alkoxy group such as, for example, ethoxy, and wherein LG2 is a leaving group, such as, for example, chlorine) with a compound of formula (VII) (as described for example in European Journal of Medicinal Chemistry, 135, 531-543; 2017 or Bioorganic & Medicinal Chemistry, 25(17), 4553-4559; 2017) optionally in a base (such as for example N,N-diisopropyl) ethylamine) or an acid (such as, for example, p-toluenesulfonic acid) in a solvent (such as dichloromethane or 1,4-dichloromethane)

It is prepared by reacting with nucleophilic substitution in alkane). When LG2 is SMe, it may be necessary to activate the leaving group, eg, by oxidation by 3-chloroperbenzoic acid.

Compounds of formula (VI) may be commercially available or may be prepared according to known procedures starting from readily available compounds.

Compounds of formula (VII) may be commercially available or may be prepared according to known procedures starting from readily available compounds.

Alternatively, carbazines of formula (III) can be prepared according to Method P5 by reacting a compound of formula (VIII) with an acid such as trifluoroacetic acid in a suitable solvent such as dichloromethane, preferably at room temperature, As previously described in Bioorganic & Medicinal Chemistry, 20(1), 487-497;2012.

Compounds of formula (VIII) are either commercially available or can be prepared according to Method P6 by combining the acid of formula (IX) with tert-butyl carbazate in a coupling agent such as, for example, 1-[bis-hexafluorophosphate]. (dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium salt 3-oxide (HATU) or 1-(3-dimethylaminopropyl base)-3-ethylcarbodiimide hydrochloride (EDC.HCl)) in the presence of a suitable Prepared when reacted in a solvent such as dichloromethane, optionally in the presence of a base such as N,N-diisopropylethylamine, as previously described in Tetrahedron, 58(27), 5513-5523; 2002 described in.

Compounds of formula (IX) may be commercially available or may be prepared according to known procedures starting from readily available compounds.

Alternatively, intermediates of formula (II) can be prepared according to Method P7 by combining compounds of formula (V) (wherein LG1 is a leaving group such as, for example, chlorine) with 2,2-difluoroacethydrazine or 2,2,2-trifluoro Acetylhydrazine is reacted in a suitable solvent such as tetrahydrofuran, acetonitrile, dichloromethane, optionally in the presence of a base such as triethylamine, preferably at -60°C, 0°C or at room temperature Prepared as previously described in Russian Journal of Organic Chemistry, 43(11), 1686-1695; 2007 or Yingyong Huaxue, 13(5), 5-9; 1996.

2,2-Difluoroacethydrazine and 2,2,2-trifluoroacethydrazine are commercially available or can be prepared according to known methods, as previously in Synlett, (12), 1939-1941; 2005, Journal of Organic Chemistry, 78(16), 8054-8064; 2013, Chemistry of Heterocyclic Compounds (New York, NY, United States), 52(2), 133-139; 2016 or WO 2018233633.

烷)中以親核性取代進行反應而製備。當LG2為SMe時，可能必需例如藉由3-氯過苯甲酸氧化，以活化脫離基。 Alternatively, compounds of formula (I) can be combined with compounds of formula (VII) according to method P8 from compounds of formula (X) wherein LG3 is a leaving group (eg as described in European Journal of Medicinal Chemistry, 135, 531-543; 2017 or WO2017065473 ) optionally in a solvent such as dichloromethane or 1,4-dichloromethane in the presence of a base such as eg triethylamine or an acid such as eg p-toluenesulfonic acid

It is prepared by reacting with nucleophilic substitution in alkane). When LG2 is SMe, it may be necessary to activate the leaving group, eg, by oxidation by 3-chloroperbenzoic acid.

Compounds of formula (X) may be commercially available or may be prepared starting from readily available compounds in analogy to Methods P1 and P2 or P3 and P4 or P7.

Alternatively, the compound of formula (I) can be prepared according to Method P9 by combining the compound of formula (XI) with _{C1 -} C3-haloalkylacetic anhydride (which may be commercially available or from readily available compounds according to known procedures) starting preparation) in a suitable solvent such as dichloromethane, preferably at 0°C, as previously described in WO2018165520.

Compounds of formula (XI) can be prepared according to Method P10 by combining compounds of formula (XII) with a source of azide such as sodium azide in a suitable solvent such as N,N-dimethylformamide, optionally exist Prepared by reaction preferably at 95°C in the presence of salts such as ammonium chloride and/or lithium chloride, as previously described in WO2018165520.

烷)中以親核取代進行反應而製備。 Compounds of formula (XII) can be prepared according to Method P11 by combining compounds of formula (XIII) (wherein LG4 is a leaving group such as chlorine) with compounds of formula (VII) (as previously described in WO2018165520), optionally in a base such as for example triethylamine) or an acid (such as, for example, p-toluenesulfonic acid) in a solvent (such as, for example, ethanol, dichloromethane, or 1,4-dichloromethane)

It is prepared by reacting with nucleophilic substitution in alkane).

Compounds of formula (XIII) are either commercially available or can be prepared according to known procedures starting from readily available compounds.

According to the invention, the processes P1 to P11 can be carried out, if appropriate, in the presence of a solvent and, if appropriate, a base.

烷、四氫呋喃、1,2-二甲 氧基乙烷、1,2-二乙氧基乙烷或苯甲醚；腈，諸如乙腈、丙腈、正丁腈或異丁腈或苯甲腈；醯胺，諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基甲醯苯胺、N-甲基吡咯啶酮或六甲基磷醯三胺；酯，諸如乙酸甲酯或乙酸乙酯；亞碸，諸如二甲亞碸；或碸，諸如環丁碸。 Suitable solvents for carrying out the processes P1 to P11 according to the invention are the customary inert organic solvents. It is preferred to use optionally halogenated aliphatic, cycloaliphatic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decahydro Naphthalene; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers such as diethyl ether, isopropyl ether, methyl tertiary butyl ether, methyl tributyl ether grade amyl ether, two

Alkane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles such as acetonitrile, propionitrile, n-butyronitrile or isobutyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylcarbanilide, N-methylpyrrolidone or hexamethylphosphoric triamine; esters, such as methyl acetate or ethyl acetate; sulfites, such as dimethylsulfoxide; or sulfites, such as cyclobutanes.

Suitable bases for carrying out the processes P1 to P11 according to the invention are the inorganic and organic bases customary for these reactions. It is preferred to use alkaline earth metals, alkali metal hydrides, alkali metal hydroxides or alkali metal alkoxides such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tertiary butoxide, or other hydrogen Ammonium oxide; alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate; alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate; and tertiary amines such as Trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, 1,4- Diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0] Undecyl-7-ene (DBU).

When carrying out the processes P1 to P11, the reaction temperature can be independently varied within a relatively wide range according to the invention. Generally, the method according to the invention is carried out at a temperature between -20°C and 160°C. One way to control the temperature used in these methods is to use microwave technology.

Processes P1 to P11 according to the invention are generally carried out independently at atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

Post-processing is carried out by conventional methods. Typically, the reaction mixture is treated with water, and the organic phase is separated off and, after drying, concentrated under reduced pressure. If appropriate, the remaining residue can be liberated from any impurities that may still be present by conventional methods, such as chromatography or recrystallization.

The compounds according to the invention can be prepared according to the methods described above. It will still be appreciated that those skilled in the art, based on their general knowledge and available publications, will be able to adapt these methods according to the particularity of each of the compounds according to the invention to be synthesized.

Compositions and Formulations

The present invention further relates to compositions, particularly compositions for the control of undesirable microorganisms. The composition can be applied to the microorganisms and/or in their habitat.

The composition comprises at least one compound of the present invention and at least one agriculturally suitable adjuvant, such as a carrier and/or a surfactant.

Carriers are solid or liquid, natural or synthetic, organic or inorganic substances, which are generally inert. The carrier usually improves 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 (especially ammonium sulfate, ammonium phosphate, and ammonium nitrate), natural rock dusts such as kaolin, clay, talc, chalk, quartz, sepiolite, montmorillonite, and silica diatomaceous earth), silica gel and synthetic rock dusts (such as finely divided silica, alumina and silicates). Examples of generally useful solid carriers for preparing particles include, but are not limited to, crushed and classified natural rocks (such as calcite, marble, pumice, sepiolite, and dolomite), synthetic particles of inorganic and organic powders, and organic materials. Particles (such as paper, sawdust, coconut husks, ears of corn, and tobacco stems). Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, for example from the following classes: aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylenes, toluene, tetralin, alkylnaphthalenes) , chlorinated aromatic or chlorinated aliphatic hydrocarbons (such as chlorobenzene, vinyl chloride or dichloromethane), alcohols and polyols (which may also be optionally substituted, etherified and/or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, untreated Substituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and esters thereof, lactamides (such as N-alkylpyrrolidone, especially N-methylpyrrolidone) and Lactones, ash and sulfites (such as dimethyl sulfoxide), oils of vegetable or animal origin. The carrier may also be a liquefied gaseous extender, ie, a liquid that is gaseous at standard temperature and pressure, such as aerosol propellants such as halocarbons, butane, propane, nitrogen and carbon dioxide.

Preferred solid carriers are selected from clays, talcs and silicas.

Preferred liquid carriers are selected from the group consisting of water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactamides and carbonates.

The amount of carrier generally ranges from 1 to 99.99% by weight of the composition, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99%.

Liquid carriers are typically present in the range from 20 to 90%, eg, 30 to 80%, by weight of the composition.

Solid carriers are generally present in the range from 0 to 50%, preferably 5 to 45%, eg 10 to 30% by weight of the composition.

If the composition contains two or more carriers, the summarised ranges refer to the total amount of carriers.

Surfactants can be ionic (cationic or anionic), zwitterionic or nonionic surfactants, such as ionic or nonionic emulsifiers, foam formers, dispersants, wetting agents, penetration enhancers, and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, ethylene oxide and/or propylene oxide and fats Polycondensates of alcohols, fatty acids or fatty amines (eg polyoxyethylene fatty acid esters (such as castor oil ethoxylate), polyoxyethylene fatty alcohol ethers (eg alkylaryl polyglycol ethers)), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (such as tristyrylphenol ethoxylates), salts of sulfosuccinates, taurine derivatives (preferably taurine alkanes) esters), phosphate esters of polyethoxylated alcohols or phenols, fatty esters of polyols (such as fatty acid esters of glycerol, sorbitol or sucrose), sulfates (such as alkyl sulfate alkoxides and alkyl ether sulfates) , sulfonates (eg, alkyl sulfonates, aryl sulfonates, and alkylbenzene sulfonates), phosphate esters, protein hydrolyzates, lignin sulfite effluents, and methyl cellulose. Any reference to salts in this paragraph preferably refers to the respective alkali metal, alkaline earth metal and ammonium salts.

Preferred surfactants are selected from the group consisting of polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkyl benzene sulfonates (such as calcium dodecyl benzene sulfonate), castor oil ethoxylates, sodium lignosulfonates and arylphenol ethoxylates (such as tristyrylphenol ethoxylates).

The amount of surfactant typically ranges from 5 to 40%, eg, 10 to 20%, by weight of the composition.

Other examples of suitable adjuvants include water repellants, drying agents, binders (adhesives, adhesives, fixatives (such as carboxymethyl cellulose), natural and synthetic polymers (such as arabic) in the form of powders, granules or latex gums, polyvinyl alcohol and polyvinyl acetate), natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinyl pyrrolidone and tylose), thickeners and secondary thickeners such as Cellulose ethers, acrylic acid derivatives, Sanxian gum, modified clays (such as those available under the name Bentone) and finely divided silica), stabilizers (such as cold stabilizers, preservatives (such as dichlorophene) and benzyl alcohol hemiformal), antioxidants, light stabilizers (especially UV stabilizers or other agents that improve chemical and/or physical stability), dyes or pigments (such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue; or organic dyes such as alizarin, azo and metallophthalocyanin dyes), antifoams (such as polysiloxane and magnesium stearate), antifreezes, adhesives, gibberellins and processing aids agents, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, chelating agents Mixtures and complex formers.

The choice of adjuvant will depend upon the desired mode of application of the compound of the invention and/or the physical properties of the compound. Furthermore, adjuvants can be selected to impart specific properties (technical, physical and/or biological properties) to the composition or the use form prepared therefrom. The choice of adjuvants can allow the composition to be tailored to specific needs.

The compositions of the present invention may be provided to the end user in "ready-to-use" formulations, ie, the compositions may be applied directly to plants or seeds by a suitable device, such as a spray or dusting device. or Alternatively, the composition may be provided to the end user as a concentrate which must be diluted (preferably in water) prior to use.

The compositions of the present invention can be prepared in a known manner, for example, by admixing a compound of the present invention with one or more suitable adjuvants, such as those disclosed herein.

The composition contains a fungicidally effective amount of a compound of the present invention. The term "effective amount" means an amount sufficient to control harmful fungi on cultivated plants or in material protection without causing substantial damage to the treated plants. Such amounts can vary widely and depend on factors such as the fungal species to be controlled, the cultivated plant or material being treated, the climatic conditions and the particular compound of the invention employed. Typically, the composition according to the present invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferably from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, most preferably From 1 to 80% by weight of the compounds of the invention. The composition may contain two or more compounds of the present invention. In this case, the summarized ranges refer to the total amount of the compounds of the present invention.

The compositions of the present invention may be in any conventional composition type, such as solutions (eg, aqueous solutions), emulsions, aqueous and oily suspensions, powders (eg, wettable powders, soluble powders), powders, pastes, granules (eg, Soluble granules, granules for spreading), suspoemulsion concentrates, natural or synthetic products impregnated with the compounds of the invention, fertilizers and microencapsulation in polymers. The compounds of the present invention may exist in suspended, emulsified or dissolved form. Examples of particularly suitable composition types are solutions, water-soluble concentrates (eg SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (eg SC, OD, OF, FS), emulsifiable concentrates substances (e.g. EC), emulsions (e.g. EW, EO, ES, ME, SE), capsules (e.g. CS, ZC), pastes, pellets, wettable powders or powders (e.g. WP, SP, WS, DP, DS), compacts (eg BR, TB, DT), granules (eg WG, SG, GR, FG, GG, MG), insecticidal articles (eg LN) and for the treatment of plant propagation material such as seeds Gel formulations (eg GW, GF). These and other types of compositions are approved by the Food and Agriculture Organization of the United Nations Nations) (FAO) definition. A review is given in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition, Croplife International, May 2008.

Preferably, the composition of the present invention is in the form of one of the following types: EC, SC, FS, SE, OD and WG, more preferably EC, SC, OD and WG.

More details on the types of compositions and examples of their preparation are given below. If two or more compounds of the present invention are present, the summarised amounts of the compounds of the present invention refer to the total amount of the compounds of the present invention. If two or more representatives of that component (eg, wetting agent, binder) are present, this comparison applies to any other component of the composition.

i) Water-soluble concentrates (SL, LS)

Dissolving 10-60% by weight of at least one compound of the invention and 5-15% by weight of a surfactant (eg polyoxyethylene fatty alcohol ether) in that amount of water and/or water solubility resulting in a total of 100% by weight in solvents such as alcohols such as propylene glycol or carbonates such as propylene carbonate. The concentrate is diluted with water prior to application.

ii) Dispersible Concentrates (DC)

5-25% by weight of at least one compound of the invention and 1-10% by weight of surfactants and/or binders (eg polyvinylpyrrolidone) are dissolved in the amount of organic compounds resulting in a total of 100% by weight. in a solvent such as cyclohexanone. Dilution with water yields a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70% by weight of at least one compound of the invention and 5-10% by weight of a surfactant (eg a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a total amount resulting in 100% by weight This amount of water-insoluble organic solvent (eg aromatic hydrocarbons or fatty acid amides) and additional water-soluble solvent if desired. Dilution with water produces an emulsion.

iv) Emulsion (EW, EO, ES)

Dissolve 5-40% by weight of at least one compound of the invention and 1-10% by weight of a surfactant (eg a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) in 20-40% by weight of water in insoluble organic solvents such as aromatic hydrocarbons. This mixture was added to the amount of water resulting in a total amount of 100% by weight using an emulsifying machine. The resulting composition was a homogeneous emulsion. The emulsion can be further diluted with water prior to application.

v) Suspensions and Suspension Concentrates

v-1) Water-based (SC, FS)

20-60% by weight of at least one compound of the invention with added 2-10% by weight of a surfactant (eg sodium lignosulfonate and polyoxyethylene fatty alcohol ether) in a suitable milling apparatus (eg, agitated ball mill) , 0.1-2% by weight of a thickener (eg Sanxianjiao) and water are ground together to produce a fine active substance suspension. The water system was added in an amount resulting in 100% by weight of the total amount. Dilution with water yields a stable suspension of the active substance. For FS type compositions, up to 40% by weight of binders (eg polyvinyl alcohol) are added.

v-2) Oily (OD, OF)

20-60% by weight of at least one compound of the invention with added 2-10% by weight of a surfactant (eg sodium lignosulfonate and polyoxyethylene fatty alcohol ether) in a suitable milling apparatus (eg, agitated ball mill) , 0.1-2% by weight of a thickener such as modified clay (especially Bentone or silica) and an organic vehicle are ground together to produce a fine active substance oil suspension. The organic vehicle is comminuted so as to result in a total of 100% by weight This amount is added. Dilution with water yields a stable dispersion of the active substance.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80% by weight of at least one compound according to the invention is finely ground together with added surfactants (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ethers), and using technical equipment (such as extrusion, spray tower, fluidization bed) into water-dispersible or water-soluble granules. Surfactant system This amount is used in such an amount that results in a total amount of 100% by weight. Dilution with water yields a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

Combine 50-80% by weight of at least one compound of the invention with added 1-8% by weight of a surfactant (eg sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and an amount resulting in a total of 100% by weight of A solid carrier, such as silica gel, is ground together in a rotor-stator type mill. Dilution with water yields a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25% by weight of at least one compound of the present invention is added with 3-10% by weight of a surfactant (such as sodium lignosulfonate), 1-5% by weight of a binder (such as carboxymethyl) cellulose) and the amount of water resulting in a total amount of 100% by weight is pulverized together. This results in a fine suspension of the active substance. Dilution with water yields a stable suspension of the active substance.

ix) Microemulsion (ME)

Add 5-20 wt% of at least one compound of the invention to 5-30 wt% organic solvent blend (eg fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend compounds such as polyoxyethylene fatty alcohol ethers and arylphenol ethoxylates and the amount of water resulting in a total of 100% by weight. This mixture was stirred for 1 h to spontaneously generate a thermodynamically stable microemulsion.

x) Microcapsules (CS)

The compound will contain 5-50% by weight of at least one compound of the present invention, 0-40% by weight of a water-insoluble organic solvent (eg aromatic hydrocarbon), 2-15% by weight of acrylic monomers (eg methyl methacrylate, methyl methacrylate) The oily phase of acrylic acid and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid such as polyvinyl alcohol. Free-radical polymerization initiated with a free-radical initiator leads to the formation of poly(meth)acrylate microcapsules. Alternatively, 5-50% by weight of at least one compound of the invention, 0-40% by weight of a water-insoluble organic solvent (eg, aromatic hydrocarbon), and an isocyanate monomer (eg, diphenylmethylene) will be included base-4,4'-diisocyanate) in an aqueous solution of a protective colloid, such as polyvinyl alcohol. Addition of polyamines such as hexamethylenediamine results in the formation of polyurea microcapsules. The monomers comprise 1 to 10 wt% of the total CS composition.

xi) Dustable powders (DP, DS)

1-10% by weight of the at least one compound of the invention is finely ground and intimately mixed with a solid carrier (eg finely divided kaolin) in that amount resulting in a total amount of 100% by weight.

xii) Granules (GR, FG)

0.5-30% by weight of the at least one compound of the invention is finely ground and combined with a solid carrier such as a silicate in that amount resulting in a total amount of 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.

xiii) Ultra Low Volume Liquid (UL)

1 to 50% by weight of the at least one compound of the invention is dissolved in the amount of organic solvent (eg aromatic hydrocarbon) resulting in a total amount of 100% by weight.

Composition types i) to xiii) may optionally contain other adjuvants, such as 0.1-1 wt % of preservatives, 0.1-1 wt % of antifoaming agents, 0.1-1 wt % of dyes and/or pigments and 5 to 10% by weight of antifreeze.

mixture/composition

The compounds and compositions of the present invention may be mixed with other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, biological control agents or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, signal compounds and/or other agriculturally beneficial agents are also possible. This may allow to expand the range of activity or prevent the development of drug resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in The Pesticide Manual, 17th edition.

Examples of fungicides that may be mixed with the compounds and compositions of the present invention are:

1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) cyproconazole ( fenhexamid), (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) Flutriafole, (1.010) Imazalil, (1.011) Imazalite sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil ), (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole , (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, ( 1.025) Triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1, 2,4-Triazol-1-ylmethyl)cyclopentanol, (1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl Base-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R) -2,2-Dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029)(2R)-2-(1-chlorocyclo propyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)( 2R)-2-[4-(4-Chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2 - alcohol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2, 2-Dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032)(2S)-2-(1-chlorocyclopropyl) -4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033)(2S)- 2-[4-(4-Chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034)(R)-[3-(4-Chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridine-3 -yl) methanol, (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2- Oxazol-4-yl](pyridin-3-yl)methanol, (1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2 -oxazol-4-yl](pyridin-3-yl)methanol, (1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl] -4-Methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038)1-({(2S,4S)-2- [2-Chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4- Triazole, (1.039)thiocyanate 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl]methyl}-1H-1, 2,4-Triazol-5-yl ester, (1.040)thiocyanate 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl ) oxon-2-yl]methyl}-1H-1,2,4-triazol-5-yl ester, (1.041) thiocyanate 1-{[rel(2R,3S)-3-(2- Chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl]methyl}-1H-1,2,4-triazol-5-yl ester, (1.042)2-[ (2R,4R,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H- 1,2,4-Triazole-3-thione, (1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6 -Trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044)2-[(2R,4S,5R)-1- (2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3 - Thione, (1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl] -2,4-Dihydro-3H-1,2,4-triazole-3-thione, (1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl) -5-Hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047)2-[ (2S,4R,5S)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H- 1,2,4-Triazole-3-thione, (1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6 -Trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049)2 -[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro- 3H-1,2,4-triazole-3-thione, (1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane- 4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy) )phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052)2-[2-chloro-4-(4-chlorophenoxy)benzene base]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl) base)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054)2-[4-(4-chlorophenoxy)-2-( Trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2- {[3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl]methyl}-2,4-dihydro-3H-1,2,4- Triazole-3-thione, (1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl ]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl )-2-(2,4-difluorophenyl)oxon-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059 ) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, ( 1.060) 5-(Allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl]methyl}- 1H-1,2,4-triazole, (1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2 ,4-Difluorophenyl)oxon-2-yl]methyl}-1H-1,2,4-triazole, (1.062)5-(allylsulfanyl)-1-{[rel( 2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxon-2-yl]methyl}-1H-1,2,4-triazole, ( 1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl -N-methyliminoformamide, (1.064)N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfur Alkyl}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.065)N'-(2,5-dimethyl-4-{[3-(2,2,3) ,3-Tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.066)N'-(2,5-dimethyl -4-{[3-(Pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.067)N'-(2, 5-Dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimino Formamide, (1.068)N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl )-N-ethyl-N-methyliminocarboxamide, (1.069)N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoro) Propyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.070)N'-(2,5-dimethyl-4-{3 -[(Pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.071)N'-(2,5-dimethyl -4-Phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfur Alkyl}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.073)N'-(4-{3-[(difluoromethyl) Sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.074)N'-[5-bromo-6-( 2,3-Dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (1.075)N' -{4-[(4,5-Dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimino Formamide, (1.076)N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}- N-ethyl-N-methyliminocarboxamide, (1.077)N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy] -2-Methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.078)N'-{5-bromo-6-[(cis-4-isopropyl Cyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.079)N'-{5-bromo-6-[trans- 4-Isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.080)N'-{5-bromo- 6-[1-(3,5-Difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.081) Ipfentrifluconazole, (1.082)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2 ,4-Triazol-1-yl)propan-2-ol, (1.083)2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1- (1,2,4-Triazol-1-yl)propan-2-ol, (1.084)2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl ]-1-(1,2,4-Triazol-1-yl)propan-2-ol, (1.085)3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2- Fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carboxylate, (1.086) fluoxytioconazole (4-[[6-[rac-(2R)-2-(2,4- Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thione-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl] oxy]benzonitrile), (1.087)N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1- Phenylethyl)phenyl]-N-methylamidocarboxamide, (1.088)N' -{5-Bromo-2-methyl-6-[(1-propoxyprop-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylamidomethyl Amide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole and (1.092) 2-[2-chloro-4-(4-chlorophenoxy) yl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate methyl ester.

2) Inhibitors of the respiratory chain of complex I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) ) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr ), (2.009) Isofetamid, (2.010) isopyrazam (santiomer 1R, 4S, 9S of the trans-epiisomer), (2.011) pyrazole Naphthoxymidine (spiegel 1S, 4R, 9R of trans-epiisomer), (2.012) pyraclostrobin (trans-epiisomer racemate 1RS, 4SR, 9SR), ( 2.013) pyraclostrobin (a mixture of the same side-epiisomer racemate 1RS, 4SR, 9RS and the trans side-epiisomer racemate 1RS, 4SR, 9SR), (2.014) pyrazinol Amine (Iso-Epiisomer Enantiomer 1R, 4S, 9R), (2.015) pyraclostrobin (Iso-Epiisomer Enantiomer 1S, 4R, 9S), ( 2.016) pyraclostrobin (same side-epimer racemate 1RS, 4SR, 9RS), (2.017) flufenazine (penflufen), (2.018) penthiopyrad (penthiopyrad), (2.019) pydiflumetofen, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3) -Trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamide, (2.023)1,3-dimethyl-N-[(3R)- 1,1,3-Trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024)1,3-dimethyl-N- [(3S)-1,1,3-Trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025)1-methyl- 3-(Trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026)2-fluoro-6- (Trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027)3-(difluoromethyl) )-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole- 4-Carboxamide, (2.028) Inpyrfluxam, (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) fluindapyr, (2.031) 3-(difluoromethyl) -N-[(3R)-7-Fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4- Formamide, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl -1H-Pyrazol-4-carboxamide, (2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl] Oxy}phenyl)ethyl]quinazolin-4-amine, (2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl) )-5-Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035)N-(2-tertiary-butyl-5-methylbenzyl)-N-cyclopropyl -3-(Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036)N-(2-tertiary-butylbenzyl)-N- Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037)N-(5-chloro-2-ethylbenzyl) )-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-( Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3, 4-Tetrahydro-1,4-methylenenaphthalen (methanophthalen)-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbamide, (2.041) N-[1-(2,4-Dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-methyl Amide, (2.042)N-[2-Chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl- 1H-Pyrazole-4-carboxamide, (2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl) (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropane yl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045)N-cyclopropyl-3-(difluoromethyl)-5 -Fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046)N-cyclopropyl-3 -(Difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047)N- Cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl- 5-Methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-( 2-Isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049)N-cyclopropyl-3-(difluoromethyl)-5 -Fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050)N-cyclopropyl-3-(difluoro Methyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051)N-cyclopropyl- 3-(Difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, ( 2.052) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-methyl Amide, (2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyridine oxazol-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl yl-1H-pyrazole-4-carboxamide, (2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5 -Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)- 5-Fluoro-1-methyl-1H-pyrazol-4-carboxamide, (2.057) pyrapropoyne, (2.058) N-[rac-(1S,2S)-2-(2,4 -Dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059)N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutane base]-2-(trifluoromethyl)nicotinamide, (2.060) flubeneteram and (2.061) thifluxamide.

3) Inhibitors in the respiratory chain of complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) acetaminophen Coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) Where to kill the same (famoxadone), (3.010) fenamidone (fenamidone), (3.011) flufenoxystrobin (flufenoxystrobin), (3.012) fluoxastrobin (fuoxastrobin), (3.013) grams of Xin (kresoxim-methyl) , (3.014) metminostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyraclostrobin (pyrametostrobin), (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{ [(E)-1-Fluoro-2-phenylethenyl]oxy}phenyl)ethylene]amino} Oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022)(2E,3Z)-5-{[1-(4-chlorophenyl) )-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023)(2R)-2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024)(2S)-2-{2-[ (2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) Mandas Robin (mandestrobin), (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-carbamoylamino-2-hydroxybenzamide, (3.028)(2E ,3Z)-5-{[1-(4-Chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3- Dimethylpent-3-enamide, (3.029){5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl} Methyl carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid and (3.032) metarylpicoxamid.

4) Inhibitors of mitosis and cell division, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide ), (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridoxine pyridachlometyl, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methyl pyridoxine, (4.011) 3-chloro-5 -(6-Chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)dazol, (4.012)4-(2-bromo-4-fluorophenyl) -N-(2,6-Difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013)4-(2-bromo-4-fluorophenyl)-N- (2-Bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014)4-(2-bromo-4-fluorophenyl)-N-(2 -Bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl) Phenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1, 3-Dimethyl-1H-pyrazol-5-amine, (4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine, (4.018)4-(2-chloro-4-fluorobenzene base)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019)4-(2-chloro-4-fluorophenyl)- N-(2-Chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020)4-(2-chloro-4-fluorophenyl)-N- (2-Chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl) )-1,3-dimethyl-1H-pyrazol-5-amine, (4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-di Methyl palladium, (4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5 -amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-Chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026 ) Fluopimide.

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) nitrile thioquinone (dithianon), (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, ( 5.016) Metiram zinc, (5.017) oxine-copper, (5.018) methyl zinc 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-dioxy-6,7-dihydro-5H -pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

6) Compounds capable of inducing host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) Tiadinil.

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, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydro) isoquinolin-1-yl)quinoline.

8) Inhibitors of ATP production, eg (8.001) silthiofam.

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-tertiary-butyl) Phenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009)(2Z)-3-(4- Tertiary-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(mfolin-4-yl)prop-2-en-1-one.

10) Inhibitors of lipid and membrane synthesis, such as (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Inhibitors of melanin biosynthesis, eg (11.001) tricyclazole, (11.002) tolprocarb.

12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) benalaxyl Le-M (mefenoxam).

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

14) Compounds capable of acting as unlinkers, eg (14.001) fluazinam, (14.002) meptyldinocap.

二唑-3-基]苯甲醯胺)、(15.074){4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基}胺甲酸甲酯、(15.075)(N-{4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲基}環丙烷甲醯胺)、(15.076)N-甲基-4-(5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.077)N-[(E)-甲氧基亞胺基甲基]-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.078)N-[(Z)-甲氧基亞胺基甲基]-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.079)N-[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]環丙烷甲醯胺、(15.080)氟菲諾代胺(flufenoxadiazam)(N-(2-氟苯基)-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺)、(15.081)2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]乙醯胺、(15.082)N-烯丙基-N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基)苯基]甲基]乙醯胺、(15.083)N-[(E)-N-甲氧基-C-甲基-伸亞胺醯基]-4-(5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.084)N-[(Z)-N-甲氧基-C-甲基-伸亞胺醯基]-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.085)N-烯丙基-N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]丙醯胺、(15.086) 4,4-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]吡咯啶-2-酮、(15.087)N-甲基-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯硫代甲醯胺、(15.088)5-甲基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]吡咯啶-2-酮、(15.089)N-((2,3-二氟-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]-3,3,3-三氟丙醯胺、(15.090)1-甲氧基-1-甲基-3-[[4-[5-(三氟甲基}-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.091)1,1-二乙基-3-[[4-[5-(三氟甲基}-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.092)N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]丙醯胺、(15.093)N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]環丙烷甲醯胺、(15.094)1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.095)N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基)環丙烷甲醯胺、(15.096)N,2-二甲氧基-N-[[4-[5-(三氟甲基}-1,2,4-

二唑-3-基]苯基]甲基]丙醯胺、(15.097)N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基)苯基]甲基]丙醯胺、(15.098)1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.099)1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.100)3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]尿素、(15.101)1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]哌啶-2-酮、(15.102)4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]異

唑啶-3-酮、(15.103)5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]異

唑啶-3-酮、(15.104)3,3-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]哌啶-2-酮、(15.105)1-[[3-氟-4-(5-(三氟甲基)-1,2,4-

二唑-3-基)苯基]甲基]氮

-2-酮、(15.106)4,4-二甲基-2-[[4-(5-(三氟甲基)-1,2,4-

二唑-3-基]苯基]甲基]異

唑啶-3-酮、(15.107)5,5-二甲基-2-[[4-[5-(三氟 甲基)-1,2,4-

二唑-3-基]苯基]甲基]異

唑啶-3-酮、(15.108)乙基1-{4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲基}-1H-吡唑-4-甲酸乙酯、(15.109)N,N-二甲基-1-{4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲基}-1H-1,2,4-三唑-3-胺、(15.110)N-{2,3-二氟-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲基}丁醯胺、(15.111)N-(1-甲基環丙基)-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.112)N-(2,4-二氟苯基)-4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯甲醯胺、(15.113)1-(5,6-二甲基吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氫異喹啉、(15.114)1-(6-(二氟甲基)-5-甲基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氫異喹啉、(15.115)1-(5-(氟甲基)-6-甲基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氫異喹啉、(15.116)1-(6-(二氟甲基)-5-甲氧基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氫異喹啉、(15.117)二甲基胺甲酸4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基酯、(15.118)N-{4-[5-(三氟甲基)-1,2,4-

二唑-3-基]苯基}丙醯胺、(15.119)3-[2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氫-2,4-苯并二氧雜

-6-基甲烷磺酸酯、(15.120)9-氟-3-[2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氫-2,4-苯并二氧雜

-6-基甲烷磺酸酯、(15.121)3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氫-2,4-苯并二氧雜

-6-基甲烷磺酸酯、(15.122)3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-9-氟-1,5-二氫-2,4-苯并二氧雜

-6-基甲烷磺酸酯、(15.123)1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氫異喹啉、(15.124)8-氟-N-(4,4,4-三氟-2-甲基-1-苯基丁-2-基)喹啉-3-甲醯胺、(15.125)8-氟-N-[(2S)-4,4,4-三氟-2-甲基-1-苯基丁-2-基]喹啉-3-甲醯胺、(15.126)N-(2,4-二甲基-1-苯基戊-2-基)-8-氟喹啉-3-甲醯胺、(15.127) N-[(2S)-2,4-二甲基-1-苯基戊-2-基]-8-氟喹啉-3-甲醯胺、(15.128)哌碳唑(picarbutrazox)、(15.129)甲特普唑(metyltretrapole)、(15.130)環丁三氟喃(cyclobutrifluram)及(15.131)氯菌靈(chloroinconazide)。 15) Other fungicides selected from the group consisting of: (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) Capsimycin, (15.005) Carvone, (15.006) Chinomethionat, (15.007) Cufraneb, (15.008) Cyflufenamid, ( 15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminium, (15.013) Forsyth- Calcium (fosetyl-calcium), (15.014) fosetyl-sodium (fosetyl-sodium), (15.015) methyl isothiocyanate, (15.016) metrafenone (metrafenone), (15.017) midiomycin ), (15.018) natamycin (natamycin), (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) ) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) phosphorous acid and its salts, (15.026) pupak- propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) gram wither (tecloftalam), ( 15.030) Tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2- oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl]ethanone, (15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazole-3- base]-1, 3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033)2- (6-Benzylpyridin-2-yl)quinazoline, (15.034) dipymetirone, (15.035) 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-oxazole -3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036)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]ethanone, (15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazole -1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1, 2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl) )-5-methylpyridin-2-yl]quinazoline, (15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H- Pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3 -Chlorophenylmethanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl] Acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonic acid Ester, (15.041) ipflufenoquin, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propane -2-ol, (15.043) fluoxapiprolin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1 -yl]acetoxy}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate , (15.045) 2-phenylphenol and its salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidine-2-ol (tautomeric form: 4-amino-5-fluoropyrimidine-2 ( 1H)-keto), (15.049) 4-oxy-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole- 2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfono (sulfono)hydrazine, (15.052)5- Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-Fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055){6- [({[(Z)-(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid butyl- 3-Alkyn-1-yl ester, (15.056)(2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester, (15.057) phenanthrene-1-carboxylic acid, (15.058)3, 4,5-Trihydroxybenzoic acid propyl ester, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) {6-[({[( 1-Methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid tertiary-butyl ester, (15.062)5 -Fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063)amino Aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimide carboxamide), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylamidocarboxamide), ( 15.066) (2-{2-[(7,8-Difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067)(5 -Bromo-1-(5,6-lutidine-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068)(3-(4,4- Difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069)(1-(4,5-dimethyl -1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070)8-fluoro-3-(5- Fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolinone, (15.071)8-fluoro-3-(5-fluoro-3,3,4,4- Tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolinone, (15.072)3-(4,4-difluoro-3,3- Dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073)(N-methyl-N-phenyl-4-[5-(trifluoromethyl) -1,2,4-

oxadiazol-3-yl]benzamide), (15.074){4-[5-(trifluoromethyl)-1,2,4-

Methyl oxadiazol-3-yl]phenyl}carbamate, (15.075)(N-{4-[5-(trifluoromethyl)-1,2,4-

oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15.076)N-methyl-4-(5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzamide, (15.077)N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzamide, (15.078)N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzamide, (15.079)N-[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]cyclopropanecarboxamide, (15.080)flufenoxadiazam (N-(2-fluorophenyl)-4-[5-(trifluoromethyl)- 1,2,4-

oxadiazol-3-yl]benzamide), (15.081)2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]acetamide, (15.082)N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl)phenyl]methyl]acetamide, (15.083)N-[(E)-N-methoxy-C-methyl-imidoimide]-4-(5- (Trifluoromethyl)-1,2,4-

Diazol-3-yl]benzylamide, (15.084)N-[(Z)-N-methoxy-C-methyl-imidoimide]-4-[5-(trifluoromethyl )-1,2,4-

Diazol-3-yl]benzamide, (15.085)N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]propionamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087)N-methyl-4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]phenylthiocarbamide, (15.088)5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089)N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2, 4-

Oxazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropionamide, (15.090)1-methoxy-1-methyl-3-[[4-[5-( Trifluoromethyl}-1,2,4-

Oxazol-3-yl]phenyl]methyl]urea, (15.091)1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-

Oxazol-3-yl]phenyl]methyl]urea, (15.092)N-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]propionamide, (15.093)N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094)1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-

Oxazol-3-yl]phenyl]methyl]urea, (15.095)N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096)N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2) ,4-

Oxazol-3-yl]phenyl]methyl]propionamide, (15.097)N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2, 4-

Oxazol-3-yl)phenyl]methyl]propionamide, (15.098)1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2 ,4-

Oxazol-3-yl]phenyl]methyl]urea, (15.099)1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]urea, (15.100)3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4 -

Oxazol-3-yl]phenyl]methyl]urea, (15.101)1-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102)4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2 ,4-

Oxazol-3-yl]phenyl]methyl]iso

oxazolidin-3-one, (15.103)5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]iso

oxazolidin-3-one, (15.104)3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105)1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-

oxadiazol-3-yl)phenyl]methyl]nitrogen

-2-keto, (15.106)4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]iso

oxazolidin-3-one, (15.107)5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl]methyl]iso

oxazolidin-3-one, (15.108)ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.109)N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1 ,2,4-

Diazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110)N-{2,3-difluoro-4-[5-(trifluoromethyl) )-1,2,4-

Diazol-3-yl]benzyl}butanamide, (15.111)N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzamide, (15.112)N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-

Diazol-3-yl]benzamide, (15.113)1-(5,6-lutidine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4 - Dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3 ,4-dihydroisoquinoline, (15.115)1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl- 3,4-Dihydroisoquinoline, (15.116)1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-di Methyl-3,4-dihydroisoquinoline, (15.117)dimethylcarbamic acid 4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl ester, (15.118)N-{4-[5-(trifluoromethyl)-1,2,4-

Oxazol-3-yl]phenyl}propionamide, (15.119)3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] Acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxa

-6-ylmethanesulfonate, (15.120)9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl Acyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxa

-6-ylmethanesulfonate, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidine- 4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxa

-6-ylmethanesulfonate, (15.122)3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidine- 4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxa

-6-ylmethanesulfonate, (15.123)1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3- Dimethyl-3,4-dihydroisoquinoline, (15.124)8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline -3-Carboxamide, (15.125)8-Fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3- Carboxamide, (15.126) N-(2,4-Dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, (15.127) N-[(2S) -2,4-Dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide, (15.128) picarbutrazox, (15.129) metprazole ( metyltretrapole), (15.130) cyclobutrifluram and (15.131) chloroinconazide.

All named mixed partners of classes (1) to (15) as described above may exist as free compounds and/or in the form of their agriculturally acceptable salts if their functional groups are feasible.

The compounds and compositions of the present invention may also be combined with one or more biological control agents.

As used herein, the term "biological control" is defined as the control of harmful organisms, such as phytopathogenic fungi and/or insects and/or mites and/or nematodes, by the use or utilization of biological control agents.

As used herein, the term "biological control agent" is defined for the purpose of biological control as an organism other than a harmful organism and/or a protein or secondary metabolite produced by such an organism. Mutants of the second organism should be included in the definition of biological control agents. The term "mutant" refers to variants of a parental strain and methods of obtaining mutants or variants, wherein the pesticidal activity is greater than that exhibited by the parental strain. A "parental strain" is defined herein as the original strain prior to mutagenesis. To obtain these mutants, the parental strain can be treated with chemicals (such as N-methyl-N'-nitro-N-nitrosoguanidine, ethylmethane) or by using gamma, x-ray, or UV-radiation irradiation, or by other means known to those skilled in the art. Known mechanisms for biological control agents include enteric bacteria that control root rot by competing with fungi for space on the root surface. Bacterial toxins, such as antibiotics, have been used to control pathogens. The toxins can be isolated and applied directly to plants, or bacterial species can be administered to produce the toxins in situ.

A "variant" is a strain that has all the identifying characteristics of an NRRL or ATCC accession number as indicated herein and can be identified as having a genome that hybridizes under high stringency conditions to the genome of an NRRL or ATCC accession number.

"Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stabilized through hydrogen bonding between the bases of nucleotide residues. Hydrogen bonding can occur in Watson-Crick base pairing, Hoogstein binding or in any other sequence specific manner. The complex may comprise two strands forming a double-strand structure, three or more strands forming a multi-strand complex, a single self-hybridizing strand, or any combination of these. Hybridization reactions can be performed under conditions of varying "stringency". Typically, low stringency hybridization reactions are performed at about 40°C with a solution/temperature of 10X SSC or equivalent ionic strength. Moderate stringency hybridizations are typically performed at about 50°C with 6X SSC, and high stringency hybridization reactions are typically performed at about 60°C with 1X SSC.

Variants of the indicated NRRL or ATCC accession numbers can also be defined as genomic sequences that have greater than 85%, more preferably greater than 90% or more preferably greater than 95% sequence identity to the genome of the indicated NRRL or ATCC accession numbers of strains. A polynucleotide or polynucleotide region (or polypeptide or polypeptide region) has a certain percentage (eg, 80%, 85%, 90% or 95%) of "sequence identity" to another sequence, meaning that when aligned , the percentage of bases (or amino acids) that are identical when comparing two sequences. This alignment and percent homology or sequence identity can be determined using software programs known in the art, eg, those described in Current Protocols in Molecular Biology (F.M. Ausubel et al., eds., 1987).

NRRL is an acronym for Agricultural Research Service Culture Collection, which is the Budapest treaty on the international recognition of the deposit of microorganisms for the purposes of patent procedure) for the purpose of depositing microbial strains at the International Conservation Agency, National Center for Agricultural Utilization Research, Agricultural Research service, U.S. Department of Agriculture, 1815 North university Street, Peroira, Illinois 61604 USA.

ATCC is an acronym for American Type Culture Collection, which is the Budapest treaty on the international recognition of the deposit of microorganisms for the purposes of patent procedure. International Depository for the Purpose of Depositing Microbial Strains, ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110 USA.

Examples of biological control agents that may be combined with the compounds and compositions of the present invention are:

Antibacterial agents selected from the group consisting of:

(A1) Bacteria, such as (A1.1) Bacillus subtilis, in particular strain QST713/AQ713 (obtained as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, with NRRL Accession No. B21661, US Pat. No. 6,060,051 ); (A1.2) Bacillus sp., in particular strain D747 (obtained as DOUBLE ^NICKEL® from Kumiai Chemical Industry Co., Ltd.), with accession number FERM BP-8234, US Pat. No. 7,094,592 (A1.3) Bacillus pumilus, in particular strain BU F-33, with NRRL accession number 50185 (obtained from BASF as part of the ^CARTISSA® product, EPA registration number 71840-19); (A1.4 ) Bacillus subtilis var. amyloliquefaciens strain FZB24 with accession number DSM 10271 (obtained as ^TAEGRO® or ^TAEGRO® ECO from Novozymes (EPA registration number 70127-5)); (A1.5 ) strain Paenibacillus sp. with accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016/154297; (A1.6) Bacillus subtilis strain BU1814 (from BASF SE as ^VELONDIS® PLUS , ^VELONDIS® FLEX and ^VELONDIS® EXTRA); (A1.7) Bacillus mojavensis strain R3B (Accession No. NCAIM(P)B001389) (WO 2013/034938), daughter from Mitsui & Co. Company Certis USA LLC; (A1.8) Bacillus subtilis CX-9060 from Certis USA LLC, a subsidiary of Mitsui &Co.; (A1.9) Paenibacillus polymyxa, in particular strain AC-1 (eg TOPSEED® from Green Biotech Company Ltd.); (A1.10) Pseudomonas proradix (eg PRORADIX® from ^{Sourcon Padena} ); (A1.11) ) Pantoea agglomerans, in particular strain E325 (Accession No. NRRL B-21856) (obtained from Northwest Agri Products as BLOOMTIME BIOLOGICAL ^™ FD BIOPESTICIDE); and

(A2) fungi such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM14941 or mixtures of blastospores of strains DSM14940 and DSM14941 (eg from bio-ferm , ^BOTECTOR® and BLOSSOM ^PROTECT® of CH); (A2.2) Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem); (A2.3) Saccharomyces cerevisiae, especially strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 from Lesaffre et Compagnie, FR (WO 2010/ 086790);

(B) a biofungicide selected from the group consisting of:

(B1) bacteria, such as (B1.1) Bacillus subtilis, in particular strain QST713/AQ713 (obtained as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with NRRL Accession No. B21661, and described in US Pat. No. 6,060,051 ); (B1.2) Bacillus pumilus, in particular strain QST2808 (obtained as SONATA® from Bayer CropScience LP, US, with Accession No. NRRL B-30087, and described in US Pat. No. 6,245,551); (B1.3) Bacillus pumilus, in particular strain GB34 (from Bayer AG, DE as Yield Shield®); (B1.4) Bacillus pumilus, in particular strain BU F-33, with NRRL accession number 50185 (from BASF as CARTISSA product Obtained in part, EPA Registration No. 71840-19); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (obtained as Double Nickel ^™ from Kumiai Chemical Industry Co., Ltd. with accession No. FERM BP -8234, U.S. Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (obtained as ^BIOBAC® WP from Bion-Tech, Taiwan, registered in Taiwan as a biofungicide with registration numbers 4764, 5454, 5096 and 5277 ); (B1.7) Bacillus subtilis strain MBI 600 (obtained as SUBTILEX from BASF SE) with Accession No. NRRL B-50595, US Pat. No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (from Bayer AG) , DE obtained as Kodiak®); (B1.9) Bacillus subtilis var. Bacillus amyloliquefaciens strain FZB24 with accession number DSM 10271 (obtained as ^TAEGRO® or ^TAEGRO® ECO from Novozymes (EPA registration number 70127-5)) (B1.10) Bacillus mycoides ramet J with accession number B-30890 ^{(obtained as BMJ TGAI® or WG and LifeGard™ from} Certis USA LLC, a subsidiary of Mitsui &Co.); (B1 .11) Bacillus licheniformis, in particular strain SB3086, with accession number ATCC 55406, WO 2003/000051 ^{(obtained as ECOGUARD® Biofungicide and GREEN RELEAF™ from} Novozymes); (B1.12) Paenibacillus strain with accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016/154297; (B1.13) Bacillus subtilis strain BU1814 (obtained from BASF SE as 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 accession number B-50768; WO 2014/028521) (STARGUS® from Marrone Bio Innovations); ( ^B1.16 ) Bacillus amyloliquefaciens strain FZB42, Accession No. DSM 23117 (obtained as RHIZOVITAL® from ^ABiTEP , DE); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis ^FMCH002 ( ^QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation); (B1. 18) Bacillus mojaveii strain R3B (Accession No. NCAIM(P)B001389) (WO 2013/034938) from Certis USA LLC, a subsidiary of Mitsui &Co.; (B1.19) Paenibacillus polymyxa (WO 2013/034938) 2016/020371) from BASF SE; (B1.20) Paenibacillus epiphyticus (WO 2016/020371) from BASF SE; (B.1.21) Pseudomonas chlororaphis strain AFS009 with accession number NRRL B- 50897, WO 2017/019448 (e.g. HOWLER ^™ and ZIO® from ^AgBiome Innovations, US); (B1.22) Pseudomonas aeruginosa, especially 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) (ACTINO- ^IRON® and ACTINOVA from Novozymes ^TE® ); (B1.24) Agrobacterium radiobacter strain K84 (eg GALLTROL-A® from ^AgBioChem , CA); (B1.25) Agrobacterium radiobacter strain K1026 (eg NOGALL from BASF SE ( ^B1.26 ) Bacillus subtilis strain KTSB ( ^FOLIACTIVE® from Donaghys); (B1.27) Bacillus subtilis IAB/BS03 (AVIV ^™ from STK Bio-Ag Technologies); (B1.28) Subtilis Bacillus strain Y1336 (obtained as ^BIOBAC® WP from Bion-Tech, Taiwan, registered as biofungicide in Taiwan with registration numbers 4764, 5454, 5096 and 5277); (B1.29) Bacillus amyloliquefaciens strain B246 ( For example, AVOGREEN ^™ 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 porogenes (eg PRORADIX® from Sourcon ^Padena ); (B1.32) Streptomyces griseoviridis strain K61 (also known as fresh Streptomyces galbus strain K61) (Accession No. DSM 7206) ( ^MYCOSTOP® from Verdera; ^PREFENCE® from BioWorks; cf. Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens (Pseudomonas fluorescens) strain A506 (eg BLIGHTBAN® ^A506 from NuFarm); and

(B2) fungi, eg: (B2.1) Coniothyrium minitans, in particular strain CON/M/91-8 (accession number DSM-9660; eg Contans® from Bayer CropScience Biologics GmbH); (B2) .2) Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride , in particular strain SC1 (with accession number CBS 122089, WO 2009/116106 and US Pat. No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (eg Sentinel from Agrimm Technologies Limited ); (B2.6) Trichoderma harzianum strain T-22 (eg Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from Simbiose Agro); (B2.14) pink sticky Gliocladium roseum (also known as Clonostachys rosea f. rosea), especially strain 321U from Adjuvants Plus, strain ACM941 disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524) or strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726'; Australas Plant Pa thol. 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, in particular strain SKT-1, with accession number FERM P-16510 (for example from Kumiai Chemical Industry ECO-HOPE®), strain T34 (e.g. T34 Biocontrol from Biocontrol Technologies SL, ES) or strain ICC 012 from Isagro; (B2.38) Trichoderma dark green, strain CNCM I-1237 (e.g. from Agrauxine, FR Esquive® WP); (B2.39) Trichoderma dark green, strain No. V08/002387; (B2.40) Trichoderma dark green, strain NMI No. V08/002388; (B2.41) Trichoderma dark green, Strain NMI No. V08/002389; (B2.42) Trichoderma dark green, strain NMI No. V08/002390; (B2.43) Trichoderma dark green, strain LC52 (for example as Tenet of Agrimm Technologies Limited); (B2 .44) Trichoderma dark green, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma dark green, strain T11 (IMI352941/CECT20498); (B2.46) Trichoderma harmatum; ( B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (eg Trichodex® from Makhteshim, US); (B2.49) Trichoderma aculeatus, especially strain kd (eg from (B2.50) Trichoderma harzianum, strain ITEM 908 (eg Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (eg Root-Pro from Mycontrol) (B2.52) Trichoderma virens (also known as Gliocladium virens), especially strain GL-21 (for example, with Certis, U S in SoilGard); (B2.53) Trichoderma viridans, strain TV1 (for example as Koppert's Trianum-P); (B2.54) Ampelomyces quisqualis, in particular strain AQ 10 (for example as IntrachemBio Italia AQ 10®); (B2.56) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (B2.57) Aureobasidium pullulans, in particular blastospores of strain DSM 14941; (B2.58) Aureobasidium pullulans Molds, in particular mixtures of strains DSM 14940 and blastospores of DSM 14941 (eg Botector® in bio-ferm, CH); (B2.64) Cladosporium cladosporioides, strain H39, with accession number CBS122244 , US 2010/0291039 (by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f.catenulate) strain J1446 (for example by Lallemand's Prestop®); (B2.70) Lecanicillium lecanii (formerly Verticillium lecanii), conidia of strain KV01 (eg by Vertalec of Koppert/Arysta ®); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183; (B2. 75) Trichoderma dark green, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) 11-253151 A; (B2.76) Trichoderma dark green, strain SKT-2 (FERM P-16511) , Japanese Patent Publication (Kokai) 11-253151 A; (B2.77) Trichoderma dark green, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) 11-253151 A; (B2.78 ) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, eg by AGROB IOSOL DE MEXICO, BioDerma of SADE CV); (B2.79) Trichoderma harzianum, strain DB 103 (obtained by Dagutat Biolab as T- ^GRO® 7456); (B2.80) Trichoderma polysporum, strain IMI 206039 (eg Binab TF WP from BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum with accession number Ts3550 (eg Tricovab from CEPLAC, Brazil); (B2.83) Ulocladium oudemansii strain U3 with accession number NM 99/06216 (eg Botry-Zen® from Botry-Zen Ltd, New Zealand and ^BOTRYSTOP® from BioWorks, Inc.); (B2. 84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850, with accession number WCS850, deposited with the Central Bureau for Fungi Cultures ( For example, DUTCH ^TRIG® by Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) Trichoderma aculeatus strain ICC 012 (also known as Trichoderma harzianum ICC012), with registration A mixture of No. CABI CC IMI 392716 and Trichoderma gaisieri (formerly Trichoderma viridans) strain ICC 080, having accession No. IMI 392151 (such as BIO-TAM™ from Isagro USA, Inc. and BIO-TAM ^™ from Agrobiosol de Mexico, SA de CV. BIODERMA ^® ); (B2.88) Trichoderma asperelloides JM41R (Accession No. NRRL B-50759) (TRICHO PLUS ^® from BASF SE); (B2.89) Aspergillus flavus) strain NRRL ²¹⁸⁸² (product called AFLA-GUARD® from Syngenta/ChemChina); (B2.90) Chaetomium cupreum (Accession No. CABI 353812) (eg BIO by AgriLife KUPRUM ^™ ); (B2.91) Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell wall ( ^CEREVISANE® from Lesaffre; ^ROMEO® from BASF SE), from Lesaffre et Compagnie, FR The strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, CNCM No. I-3939 (WO 2010/086790); (B2.92) Trichoderma cyanobacteria strain G-41, formerly known as cyanobacteria Broom mold (Accession No. ATCC 20906) (eg ^ROOTSHIELD® PLUS WP and ^TURFSHIELD® PLUS WP from BioWorks, US); (B2.93) Trichoderma hamatum with Accession No. ATCC 28012; (B2.94) ) Alternaria strain AQ10 with accession number CNCM 1-807 (eg AQ 10 ^® from IntrachemBio Italia); (B2.95) Phlebiopsis gigantea strain VRA 1992 (ROTSTOP ^® C from Danstar Ferment) ; (B2.96) Penicillium steckii (DSM 27859; WO 2015/067800) from BASF SE; (B2.97) Chaetomium globosum (obtained by Rivale as ^RIVADIOM® ) ; (B2.98) Cryptococcus flavescens (Cryptococcus flavescens), strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) Parasitism Dilophosphora alopecuri (obtained as TWIST ^FUNGUS® ); (B2.101) Fusarium oxysporum, strain Fo47 (obtained as ^FUSACLEAN® by Natural Plant Protection); (B2.102) Bacteroides flocculents ( Pseudozyma flocculosa), strain PF-A22 UL (obtained as ^SPORODEX® L from Plant Products Co., CA); (B2.103) Trichoderma galesii (formerly Trichoderma viridans), strain ICC 080 (IMI CC 39215 1 CABI) (obtained by AGROBIOSOL DE MEXICO, SADE CV as ^BIODERMA® ); (B2.104) Trichoderma fertile (eg TrichoPlus from BASF); (B2.105) Muscodor roseus), in particular strain A3-5 (Accession No. NRRL 30548); (B2.106) Simplicillium lanosoniveum;

Biological control agents having the effect of improving plant growth and/or plant health, which can be combined with the compounds according to the invention, including

(C1) bacteria selected from the group consisting of: Bacillus pumilus, in particular strain QST2808 (with accession number NRRL B-30087); Bacillus subtilis, in particular strain QST713/AQ713 (with NRRL accession number B- 21661 and described in US Pat. No. 6,060,051; obtained from Bayer CropScience LP, US as ^SERENADE® OPTI or SERENADE® ASO); Bacillus subtilis, particularly strain ^AQ30002 (with Accession No. NRRL B-50421 and described in US Patent Application Case No. 13/330,576); Bacillus subtilis, particularly strain AQ30004 (and NRRL B-50455 and described in US Patent Application No. 13/330,576); Sinorhizobium meliloti strain NRG-185- 1 ( ^NITRAGIN® GOLD from Bayer CropScience); Bacillus subtilis strain ^BU1814 (obtained as TEQUALIS® from BASF SE); Bacillus subtilis rm303 ( ^RHIZOMAX® from Biofilm Crop Protection); Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection) LOLI-PEPTA ^® ); Bacillus mycoides BT155 (NRRL No. B-50921), Bacillus mycoides EE118 (NRRL No. B-50918), Bacillus mycoides EE141 (NRRL No. B-50916), Bacillus mycoides BT46-3 (NRRL number B-50922), Bacillus cereus family member EE128 (NRRL number B-50917), Bacillus thuringiensis BT013A (NRRL number B-50924), also known as thuringiensis 4Q7, Bacillus cactus family member EE349 (NRRL number B-50928), Bacillus amyloliquefaciens SB3281 (ATCC # PTA-7542; WO 2017/205258), Bacillus amyloliquefaciens TJ1000 (obtained as ^QUIKROOTS® from Novozymes); Bacillus firmus), especially strain CNMC I-1582 (eg ^VOTIVO® from BASF SE); Bacillus pumilus, especially strain GB34 (eg YIELD ^SHIELD® from Bayer Crop Science, DE); Bacillus amyloliquefaciens, especially Strain IN937a; Bacillus amyloliquefaciens Bacillus amyloliquefaciens BS27 (Accession No. NRRL B-5015); a mixture of Bacillus licheniformis ^FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation as ^QUARTZO® ( WG), ^PRESENCE® (WP)); Bacillus cactus, in particular strain BP01 (ATCC 55675; e.g. ^MEPICHLOR® from Arysta Lifescience, US); Bacillus subtilis, in particular strain MBI 600 (e.g. ^SUBTILEX® from BASF SE ); Bradyrhizobium japonicum (eg OPTIMIZE ^® from Novozymes); Mesorhizobium cicer (eg NODULATOR from BASF SE); Rhizobium leguminosarium biovar viciae ( eg NODULATOR from BASF SE); Delftia acidovorans, especially strain RAY209 (eg ^BIOBOOST® from Brett Young Seeds); Lactobacillus sp. (eg LACTOPLANT® from ^LactoPAFI ) Paenibacillus polymyxa, in particular strain AC-1 (eg TOPSEED ^® from Green Biotech Company Ltd.); Pseudomonas porogenes (eg PRORADIX ^® from Sourcon Padena); Azospirillum brasilense ) (eg VIGOR® from KALO, Inc.); Azospirillum lipoferum (eg VERTEX-IF ^™ from TerraMax, Inc. ⁾ ; Azotobacter vinelandii and Clostridium pastoris ( Clostridium pasteurianum) (obtained as INVIGORATE® from ^Agrinos ); Pseudomonas aeruginosa, in particular strain PN1; Rhizobium leguminosarum, in particular faba bean biovar strain Z25 (accession number CECT 4585); Stem nodule nitrogen-fixing rhizobia ( Azorhizobium caulinodans, especially strain ZB-SK-5; Azorhizobacter chroococcum, especially strain H23; Azorhizobium, especially strain ATCC 12837; Bacillus siamensis, especially strain KCTC 13613T; Bacillus tequilensis, especially strain NII-0943; Serratia marcescens, especially strain SRM (accession number MTCC 8708); Thiobacillus sp. ) (eg CROPAID ^® from Cropaid Ltd UK); and

(C2) a fungus selected from the group consisting of: Purpureocillium lilacinum (previously known as Paecilomyces lilacinus) strain 251 (AGAL 89/030550; eg from Bayer CropScience Biologics) BioAct from GmbH); Penicillium bilaii strain ATCC 22348 (e.g. JumpStart® from Acceleron ^BioAg ); Talaromyces flavus, strain V117b; ® WP); Trichoderma viridans, eg strain B35 (Pietr et al. 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); Trichoderma viridis strain LC52 (also known as Trichoderma viridis strain LU132; eg Sentinel from Agrimm Technologies Limited); Trichoderma dark green strain SC1, described in International Application No. PCT/IT2008/000196); Trichoderma aculeatus strain kd (eg T-Gro from Andermatt Biocontrol); Trichoderma aculeatus Strain Eco-T (Plant Health Products, ZA); Trichoderma harzianum strain T-22 (eg Trianum-P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria strain AARC-0255 (eg from Valent Biosciences) DiTera ^™ ); Penicillium bailey strain ATCC ATCC20851; Pythium oligandrum strain M1 (ATCC 38472; e.g. Polyversum from Bioprepraty, CZ); Trichoderma cyanobacterium strain GL-21 (e.g. from Certis, USA SoilGard®); Verticillium verticillium (previously V. dahliae) strain WCS850 (CBS 276.92; e.g. Dutch Trig from Tree Care Innovations); Trichoderma dark green, in particular strain number V08/ 002387, Strain No. NMI No. V08/002388, Strain No. NMI No. V08/002389, Strain No. NMI No. V08/002390; Trichoderma harzianum strain ITEM 908; Trichoderma harzianum strain TS Th20; Trichoderma harzianum strain 1295-22; Pythium oligandrum strain DV74; Rhizopogon amylopogon (e.g. including Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba ( Examples include Myco-Sol from Helena Chemical Company); and Trichoderma viridans strain GI-3;

Insecticidally active biological control agents selected from

(D1) Bacteria selected from the group consisting of: Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; eg ^XENTARI® from Valent BioSciences); Bacillus strains J. (eg BmJ from Certis USA LLC, a subsidiary of Mitsui &Co.); Bacillus sphaericus, in particular serotype H5a5b strain 2362 (strain ABTS-1743) (eg from Valent BioSciences, ^VECTOLEX® from US); Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, IL; thuringiensis subsp. kurstaki, especially serotype H-7 (eg from Valent BioSciences , US's FLORBAC ^® WG); thuringiensis kusk subsp. strain HD-1 (for example from Valent BioSciences, US's DIPEL ^® ES); thuli kusk subsp. strain BMP 123, from Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (eg ^AQUABAC® from Becker Microbial Products IL); Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia japonica strain MBI 305) (Accession No. NRRL B-50319; WO 2011/106491 and WO 2013/032693; eg MBI-206 TGAI and ^ZELTO® from Marrone Bio Innovations); Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203; e.g. GRANDEVO® from Marrone Bio Innovations); Paenibacillus ^popilliae (formerly Bacillus popilliae; e.g. from MILKY Spore POW from St.Gabriel Laboratories DER ^™ and MILKY spore GRANULAR ^™ ); Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (Accession No. ATCC 1276) (eg ^VECTOBAC® by Valent BioSciences, US) Bacillus thuringiensis var. kurstaki strain EVB-113-19 (eg ^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; thuringiensis subsp. kuskoye strain ABTS 351; Subsp. thuringiensis strain SA 11; subsp. thuringiensis strain SA 12; subsp. thuringiensis strain EG 2348; Bacillus thuringiensis var. Colmeri (e.g. Serratia entomophila (eg ^INVADE® from Wrightson Seeds); Serratia marcescens, especially strains SRM (Accession No. MTCC 8708); and Wolbachia pipientis ZAP strains (eg ZAP ^MALES® from MosquitoMate); and

(D2) a fungus selected from the group consisting of: Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97; Beauveria bassiana) strain ATCC 74040 (eg NATURALIS ^® from Intrachem Bio Italia); Beauveria bassiana strain GHA (accession number ATCC ₇ 4250; eg BOTANIGUARD ^® ES and MYCONTROL-O ^® from Laverlam International Corporation); Cyclospora Zoophtora radicans; Metarhizium robertsii 15013-1 (deposited under NRRL Accession No. 67073); Metarhizium robertsii 23013-3 (deposited under NRRL Accession No. 67075) and Metarhizium anisopliae ) 3213-1 (deposited under NRRL Accession No. 67074) (WO 2017/066094; Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (Accession No. DSM 24665). Of these, the strain Apopka 97 is particularly preferred;

(E) A virus selected from the group consisting of: Adoxophyes orana (summer fruit leaf roller) particle propagation virus (GV), Cydia pomonella (apple leaf roller) particle propagation virus (GV) , Helicoverpa armigera (Helicoverpa armigera) nuclear polyhedrosis virus (NPV), Spodoptera exigua (Spodoptera exigua) mNPV, Spodoptera frugiperda (Autumn Spodoptera) mNPV and sea ash Spodoptera littoralis (African cotton leafworm) NPV;

(F) Bacteria and fungi that can be added "inoculum" to plants or plant parts or plant organs and which, due to their specific properties, promote plant growth and plant health. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp. ), Burkholderia spp., especially Burkholderia cepacia (previously known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Color bean puffball (Pisolithus tinctorus), Pseudomonas (Pseudomonas spp.), Rhizobium (Rhizobium spp.), especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces Streptomyces spp.; and

(G) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) useful as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense), Fortune Aza, Peppermint Oil (Fungastop), Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrin, Quassia amara , Quercus, Quillaja, Regalia, "Requiem ^TM Insecticide", Rotenone, ryania/ryanodine, Symphytum officinale ), Chrysanthemum (Tanacetum vulgare), Thymol, Triact 70, TriCon, Nasturtium (Tropaeulum majus), Urtica dioica, Veratrin (Veratrin), Mistletoe (Viscum album), Cruciferae Extracts, especially rape powder or mustard powder, and bioinsecticidal/acaricidal active substances obtained from olive oil, in particular unsaturated fats/carboxylic acids with carbon chain length C ₁₆ -C ₂₀ as active ingredients, Such as those contained in products with the trade name FLiPPER®.

The compounds and compositions of the present invention may be combined with one or more active ingredients selected from insecticides, acaricides and nematicides.

"Insecticide" and the term "insecticidal" as used herein refers to the ability of a substance to increase insect mortality or inhibit insect growth rates. As used herein, the term "insect" includes all organisms in the "Class Insecta."

"Nematicidal" and "nematicidal" refer to the ability of a substance to increase nematode mortality or inhibit the rate of nematode growth. Generally, "nematodes" include eggs, larvae, larvae and mature forms of the organism.

"Acaricide" and "acaricidal" refer to the ability of a substance to increase the mortality rate or inhibit the growth rate of ectoparasites belonging to the Arachnida and Acarid classes.

Examples of insecticides, acaricides and nematicides that may be mixed with the compounds and compositions of the present invention, respectively, are:

(1) Acetylcholinesterase (AChE) inhibitors such as, for example, carbamates such as alanycarb, aldicarb, bendiocarb, benfuracarb , Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb ), formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organic Phosphate esters such as acephate, azamethiphos, azinphos-ethyl ester, azinphos-methyl ester, cadusafos, chlorethoxyfos , chlorfenvinphos, chlormephos, chlorpyrifos-methyl ester, coumaphos, cyanophos, demeton-S-methyl ester, pine (diazinon), dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion ), ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fenthion (fosthiazate), heptenophos (heptenophos), imicyafos (imicyafos), isofenphos (isofenphos), O-(methoxyaminothiophosphamide) isopropyl salicylate, isoxathion ), malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, eumethidone ( omethoate), oxydemeton-methyl ester, parathion-methyl ester, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl ester, profenofos, propetamphos, prothiofos, pyraclofos, bifen pyridaphenthion, quinalphos, sulfotep, tebupirimifos, temephos, terbufos, tetrachlorvinphos, thiometon ), triazophos, trichlorfon and vamidothion.

(2) GABA-gated chloride channel blockers such as, for example, cyclodiene organochlorines such as chlordane and endosulfan; or phenylpyrazoles (Fepro (fiprole)) such as ethiprole and fipronil.

(3) Sodium channel modulators such as, for example, pyrethroids, such as acrinathrin, allethrin, d-cis-trans allethrin, d- Trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cypermethrin (cycloprothrin), cyfluthrin, β-cyhalothrin, cyhalothrin, λ-xylonine, γ-xylonine, cypermethrin, α-cyhalothrin, β - Cyphenothrin, θ-cyminine, ζ-cyphenothrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [( EZ)-(1R) Isomer], esfenvalerate, etofenprox, fenpropathrin, fenprox (fenvalerate), flucythrinate, flumethrin, τ-fuhuali (fluvalinate), halfenprox, imiprothrin, kadethrin, fluorine Momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin (pyrethrin) (pyrethrum)), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer)], tetramethrin tralomethrin and transfluthrin; or DDT; or methoxychlor.

(4) Modulators of nicotinic acetylcholine receptor (nAChR) competition, such as, for example, neonicotinoids such as acetamiprid, clothianidin, dinotefuran, Imidacloprid, nitenpyram, thiacloprid, and thiamethoxam; or nicotine; or sulfoxaflor or flupyridone ( flupyradifurone).

(5) Allotopic modulators of the nicotinic acetylcholine receptor (nAChR) such as, for example, spinosyns such as spinetoram and spinosad.

(6) Allotopic modulators of glutamate-gated chloride channels (GluCl), such as, for example, avermectin/milbemycin, such as abamectin, Emamectin benzoate, lepimeetin and milbemectin.

(7) juvenile hormone mimetics such as, for example, juvenile hormone analogs such as hydroprene, kinoprene and methoprene; or fenoxycarb; or Pyriproxyfen.

(8) Miscellaneous non-specific (multi-position) inhibitors such as, for example, haloalkanes such as methyl bromide and other haloalkanes; or chloropicrin; or sulphuryl fluoride; or borax; or tartar; or methyl isocyanate generators such as diazomet and metam.

(9) Regulators of the chord organ, such as, for example, pymetrozine or flonicamid.

(10) Mite growth inhibitors such as, for example, clofentezine, hexythiazox and diflovidazin or etoxazole.

(11) Microbial interfering agents for insect intestinal membranes, such as, for example, Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, thuringiensis Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb , Cry34Ab1/35Ab1.

(12) Granular gland ATP synthase inhibitors, such as ATP disruptors, such as diafenthiuron; or organotin compounds, such as azocyclotin, cyhexatin, and fenbuxil ( fenbutatin oxide); or propargite; or tetradifon.

(13) Oxidative phosphorylation decoupling agents via proton gradient interference such as, for example, chlorfenapyr, DNOC and sulfluramid.

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

(15) Type 0 chitin biosynthesis inhibitors such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, fenflubenzuron (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), lufenuron (lufenuron), novalon (novaluron), novolon (noviflumuron), teflubenzuron (teflubenzuron) and triflumuron (triflumuron) ).

(16) Type 1 chitin biosynthesis inhibitors such as buprofezin.

(17) Deskin disturbance agents (especially for Diptera, ie dipterans) such as, for example, cyromazine.

(18) Ecdysone receptor agonists such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists such as, for example, amitraz.

(20) Glandular complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl and fluacrypyrim.

(21) Glandular complex I electron transport inhibitors, such as, for example, from the group of METI acaricides, eg fenazaquin, fenpyroximate, pyrimidifen, pyrimidine (pyridaben), tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers such as, for example, indoxacarb or metaflumizone.

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

(24) Glandular complex IV electron transport inhibitors such as, for example, phosphines such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides such as calcium cyanide, potassium cyanide and cyanide Sodium.

(25) Granulo-Glandular Complex II electron transport inhibitors, such as, for example, beta-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen; or carboxylanilines, such as Paphos pytlubumide.

(28) Ryanodine receptor modulators such as, for example, diamides such as chlorantraniliprole, cyantraniliprole and flubendiamide.

唑芬(Tioxazafen)、硫氟肟醚(Thiofluoximate)、三氟苯嘧啶(Triflumezopyrim)和碘甲烷；另外以堅強桿菌(Bacillus firmus)為主之製劑(I-1582，BioNeem、Votivo)，以及下列化合物：1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(自WO2006/043635已知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(自WO2003/106457已知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]異菸鹼醯胺(自WO2006/003494已知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1,8-二氮雜螺[4.5]癸-3-烯-2-酮(自WO 2010052161已知)(CAS 1225292-17-0)、碳酸3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-側氧基-1,8-二氮雜螺[4.5]癸-3-烯-4-基乙酯(自EP2647626已知)(CAS 1440516-42-6)、4-(丁-2-炔-1-氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(自WO2004/099160已知)(CAS 792914-58-0)、PF1364(自JP2010/018586已知)(CAS 1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]亞吡啶-2(1H)-基]-2,2,2-三氟乙醯胺(自WO2012/029672已知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-亞吡啶基]-1,1,1-三氟丙-2-酮(自WO2013/144213已知)(CAS 1461743-15-6)、N-[3-(苯甲基胺甲醯基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲醯胺(自WO2010/051926已知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基胺甲醯基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲醯胺(自CN103232431已知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異

唑基]-2-甲基-N-(順式-1-氧負離子基-3-硫呾基)-苯甲醯胺、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異

唑基]-2-甲基-N-(反式-1-氧負離子基-3-硫呾基)-苯甲醯胺和 4-[(5S)-5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異

唑基]-2-甲基-N-(順式-1-氧負離子基-3-硫呾基)苯甲醯胺(自WO 2013/050317 A1已知)(CAS 1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺(自WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1已知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]胺基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亞磺醯基]-1H-吡唑-3-甲睛(自CN 101337937 A已知)(CAS 1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基胺基)硫酮基甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(Liudaibenjiaxuanan，自CN 103109816 A已知)(CAS 1232543-85-9)、N-[4-氯-2-[[(1,1-二甲基乙基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-甲醯胺(自WO 2012/034403 A1已知)(CAS 1268277-22-0)、N-[2-(5-胺基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(自WO 2011/085575 A1已知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)-嘧啶(自CN 101337940 A已知)(CAS 1108184-52-6)、(2E)-和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亞乙基]-N-[4-(二氟甲氧基)苯基]-肼甲醯胺(自CN 101715774 A已知)(CAS 1232543-85-9)、環丙烷甲酸3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯酯(自CN 103524422 A已知)(CAS 1542271-46-4)、(4aS)-7-氯-2,5-二氫-2-[[(甲氧基羰基)[4-[(三氟甲基)硫基]苯基]胺基]羰基]-茚并[1,2-e][1,3,4]

二

-4a(3H)-甲酸甲酯(自CN 102391261 A已知)(CAS 1370358-69-2)、6-脫氧基-3-O-乙基-2,4-二-O-甲基-,1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]胺甲酸酯]-α-L-哌喃甘露糖(自US 2014/0275503 A1已知)(CAS 1181213-14-8)、8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-嗒

-3-基)-3-氮雜雙環[3.2.1]辛烷(CAS 1253850-56-4)、(8-反側)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-嗒

-3-基)-3-氮雜雙環[3.2.1]辛烷(CAS 933798-27-7)、(8-同側)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-嗒

-3-基)-3-氮雜雙環[3.2.1]辛烷(自WO 2007040280 A1、WO 2007040282 A1已知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫基]-丙醯胺(自WO 2015/058021 A1、WO 2015/058028 A1已知)(CAS 1477919-27-9)和N-[4-(胺基硫酮基甲基)-2-甲基-6-[(甲基胺基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(自CN 103265527 A已知)(CAS 1452877-50-7)、5-(1,3-二

烷-2-基)-4-[[4-(三氟甲基)苯基]甲氧基]-嘧啶(自WO 2013/115391 A1已知)(CAS 1449021-97-9)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1-甲基-1,8-二氮雜螺[4.5]癸-3-烯-2-酮(自WO 2010/066780 A1、WO 2011/151146 A1已知)(CAS 1229023-34-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮雜螺[4.5]癸烷-2,4-二酮(自WO 2014/187846 A1已知)(CAS 1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-側氧基-1,8-二氮雜螺[4.5]癸-3-烯-4-基碳酸乙酯(自WO 2010/066780 A1、WO 2011151146 A1已知)(CAS 1229023-00-0)、N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亞吡啶基]-2,2,2-三氟乙醯胺(自DE 3639877 A1、WO 2012029672 A1已知)(CAS 1363400-41-2)、[N(E)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亞吡啶基]-2,2,2-三氟乙醯胺(自WO 2016005276 A1已 知)(CAS 1689566-03-7)、[N(Z)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亞吡啶基]-2,2,2-三氟乙醯胺(CAS 1702305-40-5)、3-內-3-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[[5-(三氟甲基)-2-吡啶基]氧基]-9-氮雜雙環[3.3.1]壬烷(自WO 2011/105506 A1、WO 2016/133011 A1已知)(CAS 1332838-17-1)。 Other active compounds such as Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, D-trans chloropropane Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon -Metofluthrin), ε-Momfluthrin (ε-Momfluthrin), Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Fluorine Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fluxametamide Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, Kappa Kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyrimidine Amine (Pyriminostrobin), Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Sulfur

Tioxazafen, Thiofluoximate, Triflumezopyrim, and methyl iodide; in addition, Bacillus firmus-based preparations (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 (known from WO2006/043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-ene -1-yl]-5-fluorospiro[indol-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003/106457) (CAS 637360-23-7), 2-Chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4- yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethyl Phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-2-oxy-1,8-diazaspiro[4.5]dec-3-ene-4-carbonate Ethyl ethyl ester (known from EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-oxy)-6-(3,5-dimethylpiperidin-1-yl) -5-Fluoropyrimidine (known from WO2004/099160) (CAS 792914-58-0), PF1364 (known from JP2010/018586) (CAS 1204776-60-2), N-[(2E)-1-[ (6-Chloropyridin-3-yl)methyl]pyridin-2(1H)-yl]-2,2,2-trifluoroacetamide (known from WO2012/029672) (CAS 1363400-41-2 ), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridinyl]-1,1,1-trifluoropropan-2-one (from WO2013/ 144213 known) (CAS 1461743-15-6), N-[3-(benzylaminocarboxy)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4 -(Trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010/051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro- 2-methyl-6- (Methylaminocarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazol-3-carbamoylamine (known from CN103232431) (CAS 1449220-44-3), 4-[ 5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-iso

Azolyl]-2-methyl-N-(cis-1-oxanionyl-3-thiopyranyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4 ,5-Dihydro-5-(trifluoromethyl)-3-iso

Azolyl]-2-methyl-N-(trans-1-oxoanionyl-3-thiopyranyl)-benzylamine and 4-[(5S)-5-(3,5-dichlorobenzene base)-4,5-dihydro-5-(trifluoromethyl)-3-iso

azolyl]-2-methyl-N-(cis-1-oxoanionyl-3-thiazolyl)benzylamide (known from WO 2013/050317 A1) (CAS 1332628-83-7), N-[3-Chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl ]-Propionamide, (+)-N-[3-Chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3 -Trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl -3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923 -37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl [ 4-Chloro-2-methyl-6-[(methylamino)thionemethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylate Amine (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6- Methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1 -(3-Chloro-2-pyridyl)-1H-pyrazol-5-carboxamide (known from WO 2011/085575 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)- Pyrimidines (known from CN 101337940 A) (CAS 1108184-52-6), (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluorophenyl) Methyl)phenyl]ethylene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9), cyclopropane 3-(2,2-dichlorovinyl formate) )-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-chloro- 2,5-Dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)sulfanyl]phenyl]amino]carbonyl]-indeno[1,2-e][1 ,3,4]

two

-4a(3H)-methyl formate (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]-α-L-mannanose (known from US 2014/0275503 A1) (CAS 1181213-14-8), 8-(2-cyclopropylmethoxy-4- Trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridine

-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoro Methyl-phenoxy)-3-(6-trifluoromethyl-pyridoxine

-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-isoside)-8-(2-cyclopropylmethoxy-4-trifluoro Methyl-phenoxy)-3-(6-trifluoromethyl-pyridoxine

-3-yl)-3-azabicyclo[3.2.1]octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3 -pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfanyl]-propionamide (from WO 2015/058021 A1, WO 2015/058028 A1 known) (CAS 1477919-27-9) and N-[4-(aminothionemethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl ]-3-Bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1 ,3-two

Alk-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known 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 (known 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 (known from WO 2014/187846 A1) (CAS 1638765-58-8), 3-(4-chloro- 2,6-Dimethylphenyl)-8-methoxy-1-methyl-2-oxy-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate Esters (known from WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-idene Pyridyl]-2,2,2-trifluoroacetamide (known from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]-N-[1-[( 6-Chloro-3-pyridyl)methyl]-2(1H)-pyridinyl]-2,2,2-trifluoroacetamide (known 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-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridine yl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).

Examples of herbicides that can be mixed with the compounds and compositions of the present invention are:

唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、異戊乙淨(dimethametryn)、二甲噻草胺(dimethenamid)、二甲噻草胺-P、3-(2,6-二甲基苯基)-6-[(2-羥基-6-側氧基環-1-烯-1-基)羰基]-1-甲基喹唑啉-2,4(1H,3H)-二酮、1,3-二甲基-4-[2-(甲基磺醯基)-4-(三氟甲基)苯甲醯基]-1H-吡唑-5-基-1,3-二甲基-1H-吡唑-4-甲酸酯、二甲磺隆(dimetrasulfuron)、敵樂胺(dinitramine)、特樂酚(dinoterb)、草乃敵(diphenamid)、敵草快(diquat)、敵草快-二溴(diquat-dibromid)、氟硫草定(dithiopyr)、達有龍(diuron)、DMPA、DNOC、草多索(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆-甲酯、乙嗪草酮(ethiozin)、乙呋草黃(ethofumesate)、氯氟草醚(ethoxyfen)、氯氟草醚-乙酯、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、[(3-{2-氯-4-氟-5-[3-甲基-2,6-二側氧基-4-(三氟甲基)-3,6-二氫嘧啶-1(2H)-基]苯氧基}吡啶-2-基)氧基]乙酸乙酯、F-9960、F-5231(亦即N-{2-氯-4-氟-5-[4-(3-氟丙基)-5-側氧基-4,5-二氫-1H-四唑-1-基]苯基}乙磺醯胺)、F-7967(亦即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、

唑禾草靈(fenoxaprop)、

唑禾草靈-P、

唑禾草靈-乙酯、

唑禾草靈-P-乙酯、異

苯碸(fenoxasulfone)、酚喹三酮(fenquinotrione)、四唑醯草胺(fentrazamide)、氟燕靈(flamprop)、氟燕靈-M-異丙酯、氟燕靈-M-甲酯、嘧啶磺隆(flazasulfuron)、雙氟磺草胺(florasulam)、吡氟禾草靈(fluazifop)、 吡氟禾草靈-P、吡氟禾草靈-丁酯、吡氟禾草靈-P-丁酯、氟酮磺隆(flucarbazone)、氟酮磺隆-鈉、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟噠嗪草酯(flufenpyr)、氟噠嗪草-乙酯、唑嘧磺草胺(flumetsulam)、氟胺草酯(flumiclorac)、氟胺草酯-戊酯、丙炔氟草胺(flumioxazin)、伏草隆(fluometuron)、抑草丁(flurenol)、抑草丁-丁酯、抑草丁-二甲銨(flurenol-dimethylammonium)和抑草丁-甲酯、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚-乙酯、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆-甲酯鈉(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草煙(fluroxypyr)、氟草煙-甲酯、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸-甲酯、氟磺胺草醚(fomesafen)、氟磺胺草醚-鈉、甲醯嘧磺隆(foramsulfuron)、殺木膦(fosamine)、固殺草(glufosinate)、固殺草-銨、固殺草-P-鈉、固殺草-P-銨、固殺草-P-鈉、草甘膦(glyphosate)、草甘膦-銨、草甘膦-異丙銨、草甘膦-二銨、草甘膦-二甲銨、草甘膦-鉀、草甘膦-鈉和草甘膦-三甲基硫(glyphosate-trimesium)、H-9201(亦即硫代磷醯亞胺酸O-(2,4-二甲基-6-硝基苯基)O-乙酯異丙酯)、氟氯吡啶(halauxifen)、氟氯吡啶-甲酯、氟硝磺醯胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆-甲酯、吡氟氯禾靈(haloxyfop)、吡氟氯禾靈-P、吡氟氯禾靈-乙氧基乙酯、吡氟氯禾靈-P-乙氧基乙酯、吡氟氯禾靈-甲酯、吡氟氯禾靈-P-甲酯、六嗪同(hexazinone)、HW-02(亦即1-(二甲氧基磷醯基)乙基-(2,4-二氯苯氧基)乙酸酯)、4-羥基-1-甲氧基-5-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑啶-2-酮、4-羥基-1-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑啶-2-酮、(5-羥基-1-甲基-1H-吡唑-4-基)(3,3,4-三甲基-1,1-二氧負離子基-2,3-二氫-1-苯并噻吩-5-基)甲酮、6-[(2-羥基-6-側氧基環己-1-烯-1-基)羰基]-1,5-二甲基-3-(2-甲基苯 基)喹唑啉-2,4(1H,3H)-二酮、咪草酸(imazamethabenz)、咪草酸-甲酯、甲氧咪草菸(imazamox)、甲氧咪草菸-銨、甲基咪草菸(imazapic)、甲基咪草菸-銨、依滅草(imazapyr)、依滅草-異丙銨、滅草喹(imazaquin)、滅草喹-銨、咪草菸(imazethapyr)、咪草菸-亞胺鎓(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆-甲酯鈉、碘苯腈(ioxynil)、碘苯腈-辛酸酯、碘苯腈-鉀和碘苯腈-鈉、艾分卡巴腙(ipfencarbazone)、異丙隆(isoproturon)、異惡隆(isouron)、異

草胺(isoxaben)、異

唑草酮(isoxaflutole)、卡草靈(karbutilate)、KUH-043(亦即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺醯基)-5,5-二甲基-4,5-二氫-1,2-

唑)、酮螺朵(ketospiradox)、乳氟禾草靈(lactofen)、環草定(lenacil)、利穀隆(linuron)、MCPA、MCPA-丁氧酯乙酯(MCPA-butotyl)、MCPA-二甲銨、MCPA-2-乙基己酯、MCPA-異丙銨、MCPA-鉀和MCPA-鈉、MCPB、MCPB-甲酯、MCPB-乙酯和MCPB-鈉、甲氯苯氧丙酸(mecoprop)、甲氯苯氧丙酸-鈉和甲氯苯氧丙酸-丁氧基乙酯、甲氯苯氧丙酸-P、甲氯苯氧丙酸-P-丁氧酯乙酯、甲氯苯氧丙酸-二甲銨、甲氯苯氧丙酸-2-乙基己酯和甲氯苯氧丙酸-鉀、苯噻醯草胺(mefenacet)、氟磺醯草胺(mefluidide)、磺胺磺隆(mesosulfuron)、磺胺磺隆-甲酯、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百畝(metam)、

唑醯草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、甲硫嘧磺隆(methiopyrsulfuron)、甲硫唑啉(methiozolin)、2-({2-[(2-甲氧基乙氧基)甲基]-6-(三氟甲基)吡啶-3-基}羰基)環己-1,3-二酮、異硫氰酸甲酯、1-甲基-4-[(3,3,4-三甲基-1,1-二氧橋-2,3-二氫-1-苯并噻吩-5-基)羰基]-1H-吡唑-5-基丙-1-磺酸酯、溴穀隆 (metobromuron)、異丙甲草胺(metolachlor)、S-異丙甲草胺、磺草唑胺(metosulam)、甲氧隆(metoxuron)、賽克津(metribuzin)、甲磺隆(metsulfuron)、甲磺隆-甲酯、禾草敵(molinat)、綠穀隆(monolinuron)、單嘧磺隆(monosulfuron)、單嘧磺隆-酯、MT-5950(亦即N-(3-氯-4-異丙基苯基)-2-甲基戊醯胺)、NGGC-011、敵草胺(napropamide)、NC-310(亦即[5-(苯甲氧基)-1-甲基-1H-吡唑-4-基](2,4-二氯苯基)甲酮)、草不隆(neburon)、菸嘧磺隆(nicosulfuron)、壬酸(天竺葵酸(pelargonic acid))、達草滅(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺樂靈(oryzalin)、丙炔

草酮(oxadiargyl)、

草酮(oxadiazon)、環氧嘧磺隆(oxasulfuron)、嗪草(oxaziclomefon)、乙氧氟草醚(oxyfluorfen)、巴拉割(paraquat)、巴拉割二氯化物(paraquat dichloride)、克草猛(pebulate)、二甲戊樂靈(pendimethalin)、平速爛(penoxsulam)、五氯苯酚(pentachlorphenol)、環戊

草酮(pentoxazone)、烯草胺(pethoxamid)、石油(petroleum oils)、甜菜寧(phenmedipham)、胺氯吡啶酸(picloram)、氟吡草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆-甲酯、胺基丙氟靈(prodiamine)、環苯草酮(profoxydim)、撲滅通(prometon)、撲草淨(prometryn)、撲草胺(propachlor)、敵稗(propanil)、喔草酯(propaquizafop)、撲滅津(propazine)、苯胺靈(propham)、異丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆-鈉、丙嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、雙唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚-乙酯、磺醯草吡唑(pyrasulfotole)、吡唑特(pyrazolynate)(吡唑特(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆-乙酯、苄草唑(pyrazoxyfen)、草醚 (pyribambenz)、草醚-異丙酯、草醚-丙酯、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、吡啶達醇(pyridafol)、噠草特(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚-甲酯、嘧啶硫蕃(pyrimisulfan)、嘧硫草醚(pyrithiobac)、嘧硫草醚-鈉、嘧氧碸(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、莫克草(quinoclamine)、快伏草(quizalofop)、快伏草-乙酯、快伏草-P、快伏草-P-乙酯、喹禾糠酯(quizalofop-P-tefuryl)、QYM-201、QYR-301、碸嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、西殺草(sethoxydim)、環草隆(siduron)、草滅淨(simazine)、西草淨(simetryn)、SL-261、磺草酮(sulcotrion)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆-甲酯、磺醯磺隆(sulfosulfuron)、SYN-523、SYP-249(亦即5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸1-乙氧基-3-甲基-1-側氧基丁-3-烯-2-酯)、SYP-300(亦即1-[7-氟-3-側氧基-4-(丙-2-炔-1-基)-3,4-二氫-2H-1,4-苯并

-6-基]-3-丙基-2-硫酮基咪唑啶-4,5-二酮)、2,3,6-TBA、TCA(三氯乙酸)、TCA--鈉、得匍隆(tebuthiuron)、特呋喃隆(tefuryltrione)、環磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草靈(terbucarb)、甲氧去草淨(terbumeton)、草淨津(terbuthylazin)、去草淨(terbutryn)、特福吡格利美(tetflupyrolimet)、甲氧噻草胺(thenylchlor)、噻草定(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆-甲酯、噻吩磺隆(thifensulfuron)、噻吩磺隆-甲酯、禾草丹(thiobencarb)、替艾芬斯(tiafenacil)、苯甲醯吡拉(tolpyralate)、苯吡唑草酮(topramezone)、肟草酮(tralkoxydim)、氟酮黃草胺(triafamone)、野麥畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆-甲酯、綠草定(triclopyr)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟 啶磺隆-鈉、三氟草嗪(trifludimoxazin)、氟樂靈(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆-甲酯、三氟甲磺隆(tritosulfuron)、脲硫酸鹽、滅草猛(vernolate)、ZJ-0862(亦即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苯甲基}苯胺)。 Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, grass alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amine yl-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, potassium chloropyrimidine, chloropyrimidine Acid-methyl ester, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, chlorfenidine (azafenidin), azimsulfuron, beflubutamid, beflubutamid, benazolin, benazolin-ethyl ester, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron ), bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromine bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate Ester, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, buprofen Butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl ester, chloramben, chlorobromone (chlor bromuron), 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)benzene yl}piperidin-2-one, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl) Benzyl}-1,3-dimethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorfenac, valeric acid Sodium, chlorfenprop, chlorflurenol, chlormethan-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, 2- [2-Chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzyl]-3-hydroxycyclohex-2-en-1-one, 4-{ 2-Chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzyl}-1-ethyl-1H-pyrazole-5 -yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorophthalim, chlorotoluron, chlorthal-dimethyl ester, 3-[5 -Chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, chlorsulfuron, cinidon, indol oxamethox-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop, propargyl , clomazone, clomeprop, clopyralid, cloransulam, sulfentrazone-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, Cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D- Dimethylammonium, 2,4-D-diethanolamine, 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, 2,4-D-potassium, 2,4-D-triisopropanolammonium and 2,4-D-triethanolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB- Sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl- pyrazolate) (DTP), dicamba (dicamba), dichlobenil (dichlobenil), dichlorprop (dichlorprop), dichlorprop-P, diclofop, diclofop, dichlorfen-methyl, dichlorprop- P-methyl ester, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,

Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethachlor-P, 3-(2 ,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxycyclo-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H, 3H)-dione, 1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzyl]-1H-pyrazol-5-yl- 1,3-Dimethyl-1H-pyrazole-4-carboxylate, dimtrasulfuron, dinitramine, dinoterb, diphenamid, dichlor Diquat, diquat-dibromid, dithiopyr, diuron, DMPA, DNOC, endothal, EPTC, esprocarb ), ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen , chlorofluorfen-ethyl ester, ethoxysulfuron, etobenzanid, [(3-{2-chloro-4-fluoro-5-[3-methyl-2, 6-Di-oxy-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, F- 9960, F-5231 (that is, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxy-4,5-dihydro-1H-tetrazole- 1-yl]phenyl}ethanesulfonamide), F-7967 (that is, 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]- 1-Methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,

fenoxaprop,

fenoxafen-P,

fenoxapyr-ethyl ester,

fenoxapyr-P-ethyl ester, iso

fenoxasulfone, fenquinotrione, fentrazamide, flamprop, fenoxasulfone-M-isopropyl ester, fenoxasulfone-M-methyl ester, pyrimidine flazasulfuron, florasulam, fluazifop, fenflufen-P, fenflufen-butyl, fenflufen-P-butyl Esters, flucarbazone, fluketosulfuron-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, fluoro Pyridazine-ethyl ester, flumetsulam, flumiclorac, flumechlor-amyl ester, flumioxazin, fluometuron, pyridoxine Butyl (flurenol), fuflufen-butyl ester, flurenol-dimethylammonium (flurenol-dimethylammonium), and flurenol-methyl ester, fluoroglycofen, ethyl acifluorfen-ethyl, Flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-methyl, flurtamone, fluthiacet, fluthiacet, fomesafen, fomesafen-sodium, formaldehyde Foramsulfuron (foramsulfuron), fosamine (fosamine), solid killing grass (glufosinate), solid killing grass-ammonium, solid killing grass-P-sodium, solid killing grass-P-ammonium, solid killing grass-P-sodium , glyphosate (glyphosate), glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium and grass Glyphosate-trimethyl sulfide (glyphosate-trimesium), H-9201 (that is, thiophosphoric imide O-(2,4-dimethyl-6-nitrophenyl) O-ethyl ester isopropyl Ester), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halauxifen-methyl, chlorfenapyr ( haloxyfop), pyroxyfop-P, pyroxyfop-ethoxyethyl ester, pyroxyfop-P-ethoxyethyl ester, Chlorfenapyr-methyl ester, Chlorfenapyr-P-methyl ester, hexazinone, HW-02 (that is, 1-(dimethoxyphosphoryl)ethyl-(2, 4-Dichlorophenoxy)acetate), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidine-2- ketone, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, (5-hydroxy-1-methyl-1H-pyrazole- 4-yl)(3,3,4-trimethyl-1,1-dioxanion-2,3-dihydro-1-benzothiophen-5-yl)methanone, 6-[(2- Hydroxy-6-oxycyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H )-diketone, imazamethabenz, imazameth-methyl, imazamox, imazapyr-ammonium, imazapic, imazapyr-ammonium , imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, azole Imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl methyl sodium, ioxynil, iodobenzene Nitrile-octanoate, iodobenzonitrile-potassium and iodobenzonitrile-sodium, ipfencarbazone, isoproturon, isouron, iso

Isoxaben, isoxaben

Isoxaflutole, karbutilate, KUH-043 (that is, 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H- Pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-

azole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, MCPA- Dimethylammonium, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium, MCPA-potassium and MCPA-sodium, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium, methylchlorophenoxypropionic acid ( mecoprop), methylchlorophenoxypropionate-sodium and methylchlorophenoxypropionate-butoxyethyl ester, methylchlorophenoxypropionate-P, methylchlorophenoxypropionate-P-butoxyethyl ester, methyl chloride Chlorphenoxypropionate-dimethylammonium, chlorophenoxypropionate-2-ethylhexyl and chlorophenoxypropionate-potassium, mefenacet, mefluidide , sulfasulfuron (mesosulfuron), sulfasulfuron-methyl ester, mesotrione (mesotrione), methabenzthiazuron (methabenzthiazuron), Wei Baimu (metam),

Metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, 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- Benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropan-1-sulfonate, metobromuron, metolachlor, S-metholachlor , Metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl ester, molinat, monolinuron , monosulfuron (monosulfuron), monosulfuron-ester, MT-5950 (ie N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide), NGGC-011 , napropamide, NC-310 (that is, [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone ), neburon, nicosulfuron, pelargonic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, pyrimidine orthosulfamuron, oryzalin, propyne

oxadiargyl,

oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, gram grass Meng (pebulate), pendimethalin (pendimethalin), flat speed rot (penoxsulam), pentachlorphenol (pentachlorphenol), cyclopenta

pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperazine Piperophos, pretilachlor, primisulfuron, fluorosulfuron-methyl, prodiamine, profoxydim, prometon ), prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, Trisulfuron (propoxycarbazone), probensulfuron-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil ), pyraflufen, pyraflufen-ethyl ester, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazolyl Sulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz, pyribamben-isopropyl, pyribenzoxim, pyribenzoxim, pyributicarb, pyridanol pyridafol, pyridate, pyriftalid, pyriminobac, pyrimifen-methyl, pyrimisulfan, pyrithiobac, pyrimidin Bisulfoxide-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, fast Voltaphyllum-ethyl ester, cyclosporine-P, cyclosporine-P-ethyl ester, quizalofop-P-tefuryl, QYM-201, QYR-301, rimsulfuron, benzene saflufenacil, sethoxydim, sidu ron), simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfuron-methyl Ester, sulfosulfuron, SYN-523, SYP-249 (i.e. 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 1-ethoxy base-3-methyl-1-oxybut-3-ene-2-ester), SYP-300 (that is, 1-[7-fluoro-3-oxy-4-(prop-2-yne) -1-yl)-3,4-dihydro-2H-1,4-benzo

-6-yl]-3-propyl-2-thione imidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA--sodium, stilbene tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, grass terbuthylazin, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone Methyl-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone ), tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron , Triflusulfuron-methyl, triclopyr, trietazine, trifloxysulfuron, triflusulfuron-sodium, trifludimoxazin, trifluralin (trifluralin), triflusulfuron, triflusulfuron-methyl ester, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (ie 3,4- Dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline).

Examples of plant growth regulators are:

Acibenzolar, Acibenzolar-S-methyl ester, 5-aminoacetyl propionic acid (levulinic acid), ancymidol (ancymidol), 6-benzylaminopurine, brassinolide (Brassinolid), catechin (catechine), chlormequat chloride (chlormequat chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, imide daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, edothal-dipotassium, edodosole-disodium Hectalox-mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, buprofezin-butyl ester, pyrimidine Alcohol (flurpimidol), forchlorfenuron (forchlorfenuron), gibberellic acid, inabenfide (inabenfide), indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane , probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl) ) acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-benzene Aminocarboxanic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene ), thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P .

唑(furilazole)、異地芬(isoxadifen)(-乙酯)、吡唑解草酯(mefenpyr)(-二乙酯)、萘二甲酸酐、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基胺甲醯基)胺基]苯基}磺醯基)苯甲醯胺(CAS 129531-12-0)、4-(二氯乙醯基)-1-氧雜-4-氮雜螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙醯基)-1,3-

唑啶(CAS 52836-31-4)。 Examples of safeners which may be mixed with the compounds and compositions of the invention are eg benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide , dichlormid, fenchlorazole (-ethyl ester), fenclorim, flurazole, fluxofenim, fenclorim

Furilazole, isoxadifen (-ethyl ester), mefenpyr (-diethyl ester), naphthalene dicarboxylic anhydride, oxabetrinil, 2-methoxy-N -({4-[(Methylaminocarbamoyl)amino]phenyl}sulfonyl)benzylamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxo Hetero-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-

oxazolidine (CAS 52836-31-4).

烷(triazinan)-1-基)甲基)胍、1-((2-氰基胍基)甲基)尿素、2-氰基-1-((2-氰基胍基)甲基)胍、2-氯-6-(三氯甲基)-吡啶(氯啶(nitrapyrin)或氯啶(N-serve))、二氰二胺、3,4-二甲基吡唑磷酸鹽、4,5-二甲基吡唑磷酸鹽、3,4-二甲基吡唑、4,5-二甲基吡唑、硫代硫酸銨、苦楝(neem)、基於下列成分之產品：苦楝、亞麻油酸、α-蘇子油酸、對香豆酸甲酯、阿魏酸甲酯(methyl ferulate)、3-(4-羥苯基)丙酸甲酯、水黃皮次素(karanjin)、伯奇萊可頓(brachialacton)、對苯醌高梁醌(p-benzoquinone sorgoleone)、4-胺基-1,2,4-三唑鹽酸鹽、1-醯胺基-2-硫脲、2-胺基-4-氯-6-甲基嘧啶、2-巰基苯并噻唑、5-乙氧基-3-三氯甲基-1,2,4-硫二唑(氯唑靈(terrazole)、依得利 (etridiazole))、2-磺胺基噻唑、3-甲基吡唑、1,2,4-三唑硫脲、氰胺、三聚氰胺、沸石粉、兒茶酚、苯醌、四硼酸鈉、烯丙基硫脲、氯酸鹽和硫酸鋅。 Examples of nitration inhibitors that can be mixed with the compounds and compositions of the present invention are selected from the group consisting of: 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2 -(4,5-Dimethyl-1H-pyrazol-1-yl)succinic acid, 3,4-dimethylpyrazolium glycolate, 3,4-dimethylpyrazolium acetate, lactic acid 3,4-dimethylpyrazolium salt, mandelic acid 3,4-dimethylpyrazolium salt, 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)methan amide, N-((3(5),4-dimethylpyrazol-1-yl)methyl)formamide, N-((4-chloro-3(5)-methyl-pyrazole- 1-yl) methyl) formamide; dicyandiamide, reaction adduct of urea and formaldehyde, triazonyl (triazonyl)-formaldehyde-dicyanodiamine adduct, 2-cyano-1-( (4-oxy-1,3,5-tri

Alkane (triazinan)-1-yl)methyl)guanidine, 1-((2-cyanoguanidino)methyl)urea, 2-cyano-1-((2-cyanoguanidino)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, products based on: neem, linseed oil acid, alpha-threatoleic acid, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl) propionate, karanjin, primary Brachialacton, p-benzoquinone sorgoleone, 4-amino-1,2,4-triazole hydrochloride, 1-amido-2-thiourea, 2- Amino-4-chloro-6-methylpyrimidine, 2-mercaptobenzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (terrazole, Etridiazole), 2-sulfonamidothiazole, 3-methylpyrazole, 1,2,4-triazole thiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate , allyl thiourea, chlorate and zinc sulfate.

The compounds and compositions of the present invention may be used in combination with one or more agricultural benefit agents.

Examples of agricultural benefit agents include biostimulants, plant growth regulators, plant signaling molecules, growth enhancers, microbial stimulators, biomolecules, soil amendments, nutrients, plant nutrient enhancers, and the like, such as lipochitooligosaccharides (LCO), chitosan oligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or derivatives thereof (eg jasmonate), cytokines, growth hormones, gibberellins, abscisic acid, ethylene, rapeseed steroids , salicylates, macro- and micronutrients, linoleic acid or its derivatives, threinoleic acid or its derivatives, karrikin and beneficial microorganisms such as Rhizobium spp., Bradyrhizobium spp., Sinorhizobium spp., Azorhizobium spp., Glomus spp., Gigaspora spp. ), Hymenoscyphous spp., Oidiodendron spp., Laccaria spp., Pisolithus spp., Rhizobium , Puffball, Rhizoctonia spp., Acinetobacter spp., Arthrobacter spp., Arthrobotrys spp., Koji ( Aspergillus spp.), Azospira, Bacillus spp., Burkholderia, Candida spp., Chryseomonas spp., Enterobacter spp .), Eupenicillium spp., Exiguobacterium spp., Klebsiella spp., Kluyvera spp., Microbacterium ( Microbacterium spp.), Mucor spp., Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas spp.), Serratia spp., Stenotrophomonas maltophilia (Stenotrophomonas spp.), Streptomyces (Streptomyces spp.), Streptosporangium spp., Swaminathania spp., Thiobacillus spp., Torula sp. Genus (Torulospora spp.), Vibrio spp., Xanthobacter spp., Xanthomonas spp., etc.) and combinations thereof.

Method and use

The compounds and compositions of the present invention have potent microbicidal activity and/or plant defense modulating potential. They can be used to control undesired microorganisms on plants, such as undesired fungi and bacteria. They can be particularly effective in crop protection (they control microorganisms that cause plant disease) or for the protection of materials (eg, industrial materials, lumber, or stored goods), as described in more detail below. More specifically, the compounds and compositions of the present invention can be used to protect seeds, germinated seeds, emerging seedlings, plants, plant parts, fruits, harvested goods and/or the soil in which the plants are grown from unwanted microorganisms.

Control/controlling, as used herein, includes protective, curative and eradicative treatments of undesirable microorganisms. Undesirable microorganisms can be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes or pathogenic fungi, more particularly phytopathogenic bacteria, phytopathogenic viruses, phytopathogenic oomycetes or phytopathogenic fungi. As detailed below, these phytopathogenic microorganisms are causative agents of a broad spectrum of plant diseases.

More specifically, the compounds and compositions of the present invention are useful as fungicides. For the purpose of this specification, the term "fungicide" refers to a fungicide that can be used in crop protection to control undesired fungi such as Plasmodiophoromycete, Chytridiomycete, Zygomycetes, Ascomycetes (Ascomycete, Basidiomycete and Deuteromycete) and/or compounds or compositions controlling Oomycetes.

The compounds and compositions of the present invention can also be used as antibacterial agents. In particular, they can be used in crop protection, eg for the control of undesired bacteria, such as the families Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae ), Corynebacteriaceae and Streptomycetaceae.

The compounds and compositions of the present invention can also be used as antiviral agents in crop protection. For example, the compounds and compositions of the present invention may be effective against diseases caused by plant viruses such as: tobacco mosaic virus (TMV), tobacco rattle virus, tobacco dwarf virus (TStuV), tobacco roll Leaf Virus (VLCV), Tobacco Vein Blue Mosaic Virus (TVBMV), Tobacco Necrotizing Dwarf Virus (TNDV), Tobacco Streak Virus (TSV), Potato Virus X (PVX), Potato Virus Y, S, M and A , Potato acuba mosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf roll virus (PLRV), alfalfa mosaic virus (AMV), courgette mosaic virus (CMV), courgette green spot mosaic virus (CGMMV), courgette yellowing virus (CuYV), watermelon mosaic virus (WMV), tomato spotted wilt virus (TSWV), tomato rotation virus (TomRSV), sugarcane mosaic virus (SCMV), rice atrophy virus, rice canola virus, rice black streak atrophy, strawberry spot virus (SMoV), strawberry veneer virus (SVBV), strawberry mild yellow edge virus (SMYEV), strawberry shrinkage virus (SCrV) ), broad bean wilting virus (BBWV), and melon necrotic spot virus (MNSV).

The present invention also relates to a method for controlling undesired microorganisms such as undesired fungi, oomycetes and bacteria on plants, comprising applying to the microorganisms at least one compound of the present invention or at least one composition of the present invention and/or or their habitat (application to plants, plant parts, seeds, fruits or to the soil in which the plants grow).

Generally, the compounds and compositions of the present invention are effective and plant compatible when used in curative or protective methods of controlling phytopathogenic fungi and/or phytopathogenic oomycetes is applied to the plant, plant part, fruit, seed or soil or substrate in which the plant grows. Suitable substrates that can be used to grow plants include inorganic substrate substrates such as mineral wool, especially rock wool, perlite, sand or gravel; organic substrates such as peat, pine bark or sawdust; and petroleum substrate substrates such as polymeric foam or Plastic beads. An effective and phytocompatible amount means an amount sufficient to control or destroy fungi that are present or prone to appear on cultivated land without subjecting the crop to any significant symptoms of phytotoxicity. Such amounts may vary widely depending on the fungus to be controlled, the type of crop, the stage of crop growth, the climatic conditions and the individual compounds and compositions of the invention employed. This amount can be determined by systematic field trials within the purview of those skilled in the art.

Plants and Plant Parts

The compounds and compositions of the present invention can be applied to any plant or plant part.

Plant means all plants and flora, such as desired and undesired wild plants or crop plants (including natural crops). Crop plants can be plants that can be obtained by conventional methods of breeding and optimization or by biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMO or transgenic plants) and Plant cultivars not protected by plant breeders' rights.

Plant cultivars are understood to mean plants with novel properties ("traits") obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, varieties, biotypes or genotypes.

Plant parts are understood to mean all parts and organs of plants above and below ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and reproductive propagation material, such as cuttings, tubers, rhizomes, cuttings and seeds.

Plants that can be treated according to the methods of the present invention include the following: cotton, flax, vines, fruits, vegetables, such as Rosaceae sp. (eg pome fruit such as apples and pears, but also stone fruits such as apricots, cherries, almonds) and peaches, and berries 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 plantations), madder Families (Rubiaceae sp.) (e.g. coffee), Theaceae (Theaceae sp.), Sterculiceae sp., Rutaceae (e.g. lemon, citrus and grapefruit); Solanaceae (Solanaceae sp.) ) (e.g. tomatoes), Liliaceae (Liliaceae sp.), Asteraceae (Asteraceae sp.) (e.g. lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp. ), Cucurbitaceae sp. (e.g. courgettes), Alliaceae (Alliaceae sp.) (e.g. leeks, onions), Papilionaceae sp. (e.g. peas); major crop plants such as Poaceae ( Gramineae sp.) (eg corn, turf, cereals such as wheat, rye, rice, barley, oats, chestnut and triticale), Asteraceae sp. (eg sunflower), Brassicaceae sp. (e.g. cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, cabbage, radish, and canola, mustard greens, horseradish, and cress), Fabacae sp. (e.g. beans, peanuts) , Papilionaceae sp. (e.g. soybean), Solanaceae (Solanaceae sp.) (e.g. potato), Chenopodiaceae sp. (e.g. beet, forage beet, beetroot, beetroot); with Plants and ornamental plants useful in gardens and woodlands; and genetically modified varieties of each of these plants.

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 stressors, i.e. those plants exhibit resistance to animals and microbes. Better defense against biological pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars that can be treated by the methods disclosed above include those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, Avoid the shade.

Plants and plant cultivars that can be treated by the methods disclosed above include those plants characterized by enhanced yield characteristics. Increased yield in the plant can be, for example, the result of improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency, and increased germination efficiency. Alkyne matures. Yield can additionally be affected by improved plant type (under stressful and non-stressed conditions), including but not limited to early flowering, flowering control for hybrid seed production, seedling vigour, plant size, number and distance of internodes, root growth , seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed quality, enhanced seed filling, reduced seed spread, reduced pod dehiscence and resistance Lodging. Other yield traits include seed composition, such as carbohydrate content and composition (eg, cotton or starch), protein content, oil content and composition, nutrient value, reduction in antinutrient compounds, improved processability, and better storage stability.

Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are hybrid plants that have exhibited heterosis resulting in generally higher yield, vigor, health and resistance to biotic and abiotic stress or characteristics of hybrid vigour.

Transgenic plants, seed treatment and integration events

The compounds according to the invention can advantageously be used for the treatment of transgenic plants, plant cultivars or plant parts receiving genetic material which will have advantageous and/or useful properties (Traits) are imparted to these plants, plant cultivars or plant parts. Accordingly, it is contemplated that the present invention may be combined with one or more recombination traits or gene transfer events or combinations thereof. For the purposes of this application, a gene transfer event is produced by inserting a specific recombinant DNA molecule into a specific location (locus) within the chromosome of the plant genome. Insertions generate novel DNA sequences called "events" and are characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent or flanking both ends of the inserted DNA. Such trait(s) or transgenic events include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, hybrid seed production, and herbicide tolerance, wherein the trait is Measured relative to plants lacking these traits or transgenic events. Specific examples of such advantageous and/or useful properties (traits) are better plant growth, vigour, stress tolerance, standing, lodging resistance, nutrient uptake, plant nutrients and/or yield, in particular improved growth, Increased tolerance to high or low temperatures, increased tolerance to drought or water level or soil salinity, enhanced flowering performance, easier harvest, accelerated ripening, higher yield, higher quality and/or higher nutrients of the harvested product Value, better shelf life and/or processability of the harvested product, and increased resistance against animal and microbial pests such as against insects, arachnids, nematodes, mites, slugs and snails.

Among the DNA sequences encoding proteins conferring tolerance against such animal and microbial pests, especially insects, particular mention is made of the genetic material from Bacillus thuringiensis encoding the Bt protein, which is broadly described in in the literature and well known to those skilled in the art. Proteins extracted from bacteria such as Photorhabdus are also mentioned (WO97/17432 and WO98/08932). In particular, reference is made to Bt Cry or VIP proteins including Cry1A, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF proteins or toxin fragments thereof and hybrids or combinations thereof, especially Cry1F proteins or derivatives Hybrid from Cry1F protein (eg hybrid Cry1A-Cry1F protein or toxin fragment thereof), Cry1A type protein or toxin fragment thereof, preferably Cry1Ac protein or derived from Cry1Ac Hybrid compounds of proteins (eg hybrid Cry1Ab-Cry1Ac proteins), or Cry1Ab or Bt2 proteins or toxin fragments thereof, Cry2Ae, Cry2Af or Cry2Ag proteins or toxin fragments thereof, Cry1A.105 proteins or toxin fragments thereof, VIP3Aa19 proteins, VIP3Aa20 proteins , VIP3A protein, VIP3Aa protein or toxin fragments thereof produced in COT202 or COT203 cotton events (as described in Estruch et al. (1996), Proc Natl Acad Sci US A. 28;93(11):5389-94 ), Cry proteins (as described in WO2001/47952), from Xenorhabdus (as described in WO98/50427), Serratia (in particular from Serratia entomophila) (S. entomophila) or Photorhabdus species strains of insecticidal proteins, such as Tc proteins from Photorhabdus (as described in WO 98/08932). Also included herein are any variants or mutants of any of these proteins that have some amino acid differences (1 to 10, preferably 1 to 10) from any of the above-named sequences (especially the sequences of the toxin fragments thereof). 1 to 5) or a fusion with a transit peptide (such as a plastid transit peptide) or another protein or peptide.

Another and particularly emphasized example of these properties is conferring tolerance to one or more herbicides such as imidazolinones, sulfonylureas, glyphosate or phosphinothricin. Among the DNA sequences encoding proteins conferring tolerance to specific herbicides in transformed plant cells and plants, particular mention is made of the bar or PAT genes or the Streptomyces coelicolor described in WO 2009/152359 A gene that confers tolerance to solid-killing herbicides, a gene encoding an appropriate EPSPS (5-enolpyruvylshikimate-3-phosphate synthase) that confers resistance to herbicides with EPSPS as the target (especially tolerance to herbicides such as glyphosate and its salts), a gene encoding a glyphosate-n-acetyltransferase or a gene encoding a glyphosate oxidoreductase. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (eg WO2007/024782), mutant Arabidopsis ALS/AHAS genes (eg US Pat. No. 6,855,533), coding for 2,4-D(2,4-Dichlorophenoxyacetic acid) Gene of 2,4-D-monooxidase for tolerance to dicamba and encoding dicamba monooxidase conferring tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid) Enzyme genes.

Yet another example of such properties is tolerance to one or more phytopathogenic fungi such as Asian soybean rust. Among the DNA sequences encoding proteins conferring tolerance against these diseases, particular mention is made of those from broad-leaved soybean (glycine tomentella), for example from the publicly available accession series PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, The genetic material of any one of PI499933, PI441008, PI505256 or PI446961, as described in WO2019/103918.

Another and particularly emphasized example of such properties is due to, for example, systemic acquired resistance (SAR), systemins, plant defensins, elicitors, and resistance genes and corresponding expressions increased resistance against bacteria and/or viruses due to proteins and toxins.

Transgenic events that are particularly useful in transgenic plants or plant cultivars that can preferably be treated according to the present invention include event 531/PV-GHBK04 (cotton, insect control, described in WO2002/040677), event 1143-14A ( Cotton, insect control, not deposited, described in WO2006/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002/034946); event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010/117737); event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010/117735); Event 281-24-236 (Cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005/103266 or US-A 2005-216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US-A 2007-143876 or WO2005/103266); event 3272 (maize, quality trait, deposited as PTA-9972, as described in WO2006/098952 or US-A 2006-230473); event 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002/027004), event 40416 (maize, insect control-herbicide tolerance, deposited as ATCC PTA) -11508, described in WO 11/075593); event 43A47 (maize, insect control - herbicide tolerance, deposited with ATCC PTA-11509, described in WO2011/075595); event 5307 (maize, insect control, deposited with ATCC) PTA-9561, described in WO 2010/077816); Event ASR-368 (Panthera chinensis, herbicide tolerant, deposited with ATCC PTA-4816, described in US-A 2006-162007 or WO2004/053062); Event B16 ( Maize, herbicide tolerance, not deposited, described in US-A 2003-126634); Event BPS-CV127-9 (Soybean, herbicide tolerance, deposited under NCIMB No. 41603, described in WO2010/080829); Event BLR1 (rape, restored male sterility, deposited as NCIMB 41193, described in WO2005/074671), event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); event CE44-69D (cotton, insect control, not deposited, described in WO2006/128571); event CE46-02A (cotton, Insect control, not deposited, described in WO2006/128572); event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004/039986); event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005/054479); event COT203 (cotton, insect control, not deposited, described in WO2005/054480);); event DAS21606-3/1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012/033794), event DAS40278 (maize, herbicide tolerance, deposited with ATCC PTA-10244, described in WO2011/022469); event DAS-44406-6/pDAB8264.44.06.1 (soybean , herbicide tolerance, deposited as PTA-11336, described in WO2012/075426), event DAS-14536-7/pD AB8291.45.36.2 (Soybean, herbicide tolerance, deposited as PTA-11335, described in WO2012/075429), event DAS-59122-7 (maize, insect control - herbicide tolerance, deposited with ATCC PTA 11384, described in US-A 2006-070139); event DAS-59132 ( Maize, insect control - herbicide tolerance, not deposited, described in WO2009/100188); event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011/066384 or WO2011/066360); Event DP-098140-6 (maize, herbicide tolerance, deposited with ATCC PTA-8296, described in US-A 2009-137395 or WO 08/112019); event DP-305423-1 (soybean, quality trait, no Deposit, described in US-A 2008-312082 or WO2008/054747); Event DP-32138-1 (maize, hybrid system, deposited as ATCC PTA-9158, described in US-A 2009-0210970 or WO2009/103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited with ATCC PTA-8287, described in US-A 2010-0184079 or WO2008/002872); event EE-I (eggplant, insect control, not deposited, described in WO 07/091277); event Fil 17 (maize, herbicide tolerance, deposited with ATCC 209031, described in US-A 2006-059581 or WO 98/044140); event FG72 (soybean, herbicide tolerance, deposited are PTA-11041, described in WO2011/063413), event GA21 (maize, herbicide tolerance, deposited with ATCC 209033, described in US-A 2005-086719 or WO 98/044140); event GG25 (maize, herbicide) Tolerance, deposited with ATCC 209032, described in US-A 2005-188434 or WO98/044140); Event GHB119 (cotton, insect control - herbicide tolerance, deposited with ATCC PTA-8398, described in WO2008/151780) ; event GHB614 (cotton, herbicide tolerance, deposited with ATCC PTA-6878, described in US-A 2010-050282 or WO2007/017186); event GJ11 (maize, herbicide tolerance, deposited with ATCC 209030, described in US-A 2005-188434 or WO98/044140); event GM RZ13 (beet, virus resistance, deposited as NCIMB-41601, described in WO2010/076212); Incident H7-1 (beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004/074492); event JOPLIN1 (wheat, disease tolerance, not deposited, described in US-A 2008-064032); Event LL27 (Soybean, herbicide tolerance, deposited as NCIMB41658, described in WO2006/108674 or US-A 2008-320616); Event LL55 (Soybean, herbicide tolerance, deposited as NCIMB 41660, described in WO 2006/108675 or US-A 2008-196127); event LLcotton25 (cotton, herbicide tolerance, deposited with ATCC PTA-3343, described in WO2003/013224 or US-A 2003-097687); Event LLRICE06 (rice, herbicide tolerance, deposited with ATCC 203353, described in US 6,468,747 or WO2000/026345); event LLRice62 (rice, herbicide tolerance, deposited with ATCC 203352, described in WO2000/026345), event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A 2008-2289060 or WO2000/026356); event LY038 (maize, quality trait, deposited as ATCC PTA-5623, described in US- A 2007-028322 or WO2005/061720); event MIR162 (maize, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007/142840); event MIR604 (maize, insect control, not deposited, described in US-A 2008-167456 or WO2005/103301); event MON15985 (cotton, insect control, deposited with ATCC PTA-2516, described in US-A 2004-250317 or WO2002/100163); event MON810 (maize, insect control, Not deposited, described in US-A 2002-102582); event MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO2004/011601 or US-A 2006-095986); event MON87427 (maize, pollination control, Deposited as ATCC PTA-7899, described in WO2011/062904); event MON87460 (maize, stress tolerance, deposited as ATCC PTA-8910, described in WO2009/111263) or US-A 2011-0138504); Event MON87701 (Soybean, insect control, deposited with ATCC PTA-8194, described in US-A 2009-130071 or WO2009/064652); event MON87705 (soybean, quality trait - herbicide tolerance, deposited with ATCC PTA-9241, described in US-A 2010-0080887 or WO2010/037016); event MON87708 (soybean, herbicide agent tolerance, deposited as ATCC PTA-9670, described in WO2011/034704); event MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012/051199), event MON87754 (soybean, quality trait, deposited as ATCC PTA-9385, described in WO2010/024976); event MON87769 (soybean, quality trait, deposited with ATCC PTA-8911, described in US-A 2011-0067141 or WO2009/102873); event MON88017 (maize, insect control - herbicide) Tolerance, deposited with ATCC PTA-5582, described in US-A 2008-028482 or WO2005/059103); Event MON88913 (cotton, herbicide tolerance, deposited with ATCC PTA-4854, described in WO2004/072235 or US -A 2006-059590); event MON88302 (rape, herbicide tolerance, deposited as PTA-10955, described in WO2011/153186), event MON88701 (cotton, herbicide tolerance, deposited as PTA-11754, described in WO2012/134808), event MON89034 (maize, insect control, deposited with ATCC PTA-7455, described in WO 07/140256 or US-A 2008-260932); event MON89788 (soybean, herbicide tolerance, deposited with ATCC PTA) -6708, described in US-A 2006-282915 or WO2006/130436); event MS1 1 (rape, pollination control - herbicide tolerance, deposited with ATCC PTA-850 or PTA-2485, described in WO2001/031042); Event MS8 (canola, pollination control - herbicide tolerance, deposited with ATCC PTA-730, described in WO2001/041558 or US-A 2003-188347); event NK603 (maize, herbicide tolerance, deposited with ATCC PTA) -2478, described in US-A 2007-292854); event PE-7 (rice, insect control, not deposited, described in WO2008/114282); event RF3 (oilseed rape, pollination control - herbicide tolerance, deposited with ATCC PTA-730 , described in WO2001/041558 or US-A 2003-188347); event RT73 (rape, herbicide tolerance, unregistered, described in WO2002/036831 or US-A 2008-070260); event SYHT0H2/SYN-000H2-5 (soybean, herbicide tolerance, Deposited as PTA-11226, described in WO2012/082548), event T227-1 (beet, herbicide tolerance, not deposited, described in WO2002/44407 or US-A 2009-265817); event T25 (maize, herbicide) Tolerance, not deposited, described in US-A 2001-029014 or WO2001/051654); Event T304-40 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010) -077501 or WO2008/122406); event T342-142 (cotton, insect control, unregistered, described in WO2006/128568); event TC1507 (maize, insect control - herbicide tolerance, not deposited, described in US-A 2005-039226 or WO2004/099447); event VIP1034 (maize, insect control - herbicide tolerance, deposited with ATCC PTA-3925, described in WO2003/052073), event 32316 (maize, insect control - herbicide tolerance) , deposited as PTA-11507, described in WO2011/084632), event 4114 (maize, insect control - herbicide tolerance, deposited as PTA-11506, described in WO2011/084621), event EE-GM3/FG72 (soybean, Herbicide Tolerance, ATCC Accession No. PTA-11041) selectively stacks with Event EE-GM1/LL27 or Event EE-GM2/LL55 (WO2011/063413A2), Event DAS-68416-4 (Soybean, herbicide tolerance) sex, ATCC accession number PTA-10442, WO2011/066360A1), event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, WO2011/066384A1), event DP-040416-8 (maize, Insect Control, ATCC Accession No. PTA-11508, WO2011/075593A1), Event DP-043A47-3 (Corn, Insect Control, ATCC Accession No. PTA-11509, WO2011/075595A1), Event DP-004114-3 (Corn, Insect Control , ATCC Accession No. PTA-11506, WO2011/084621A1), Event DP-032316-8 (Corn, Insect Control, ATCC Accession No. PTA- 11507, WO2011/084632A1), event MON-88302-9 (Canola, Herbicide Tolerance, ATCC Accession No. PTA-10955, WO2011/153186A1), Event DAS-21606-3 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-11028, WO2012/033794A2), Event MON-87712-4 (Soybean, Quality Traits, ATCC Accession No. PTA-10296, WO2012/051199A2), Event DAS-44406-6 (Soybean, Stacked Herbicide Tolerance, ATCC Accession No. PTA-11336, WO2012/075426A1 ), event DAS-14536-7 (soybean, herbicide tolerance stacked, ATCC accession number PTA-11335, WO2012/075429A1), event SYN-000H2-5 (soybean, herbicide tolerance, ATCC accession number PTA) -11226, WO2012/082548A2), event DP-061061-7 (rape, herbicide tolerance, no accession number obtained, WO2012071039A1), event DP-073496-4 (rape, herbicide tolerance, no accession number obtained , US2012131692), Event 8264.44.06.1 (Soybean, Stacked Herbicide Tolerance, Accession No. PTA-11336, WO2012075426A2), Event 8291.45.36.2 (Soybean, Stacked Herbicide Tolerance, Accession No. PTA-11335, WO2012075429A2 ), event SYHT0H2 (soybean, ATCC accession number PTA-11226, WO2012/082548A2), event MON88701 (cotton, ATCC accession number PTA-11754, WO2012/134808A1), event KK179-2 (alfalfa grass, ATCC accession number PTA-11833) , WO2013/003558A1), event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC accession number PTA-11993, WO2013/010094A1), event MZDT09Y (maize, ATCC accession number PTA-13025, WO2013/012775A1 ).

In addition, these lists of transgenic events are provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found in its Global Information NET's website at aphis.usda.gov. For the purposes of this application, the status of this list is relative to the filing date of this application.

Genes/events conferring the desired trait in question can also be present in transgenic plants in combination with each other. Examples of transgenic plants mentioned are important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rape, and fruiting plants (fruits are apples, pears, citrus and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco and rape. Traits of particular emphasis are increased plant resistance to insects, arachnids, nematodes and slugs and snails, and increased plant resistance to one or more herbicides.

Commercially available examples of such plants, plant parts or plant seeds which may preferably be treated according to the invention include GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO® , BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY® 2 XTEN ^DTM , INTACTA RR2 PRO®, VISTIVE GOLD®, and/or XTENDFLEX ^TM trade names of commercial products, such as plant seeds.

pathogen

Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include:

Diseases caused by the following powdery mildew pathogens: eg Blumeria species, eg Blumeria graminis; Podosphaera species, eg Blumeria graminis Podosphaera leucotricha; Sphaerotheca species, eg Sphaerotheca fuliginea; Uncinula species, eg Uncinula necator;

Diseases caused by rust pathogens such as Gymnosporangium species, such as Gymnosporangium sabinae); Hemileia species such as Hemileia vastatrix; Phakopsora species such as Phakopsora pachyrhizi or Phakopsora pachyrhizi (Phakopsora meibomiae); Puccinia species such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; Puccinia Uromyces species) such as Uromyces appendiculatus;

Diseases caused by pathogens of the following Oomycetes group: eg Albugo species, eg Albugo candida; Bremia species, eg Bremia lactucae); Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans ); Plasmopara species such as Plasmopara viticola; Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis ; Pythium species, such as Pythium ultimum;

Leaf spot and leaf blight caused by eg: Alternaria species, eg Alternaria solani; Cercospora species, eg Cercospora beet (Cercospora beticola), Cladosporium species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidal form: Drechslera, synonyms: Helminthosporium or Cochliobolus miyabeanus); Colletotrichum species, e.g. Colletotrichum lindemuthanium); Corynespora species, for example Such as Corynespora cassiicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri ); Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species ), such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans ); Magnaporthe species such as Magnaporthe grisea; Microdochium species such as Microdochium nivale; Mycosphaerella species , eg Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, eg Phaeosphaeria nodorum; Pyrenophora species such as Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species such as Ramularia collo -cygni) or Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria Septoria apii or Septoria lycopersici; Stagonospora species such as Stagonospora nodorum; Typhula species such as Typhula incarnata ); Venturia species, such as Venturia inaequalis;

Root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Plasmodiophora species, such as Plasmodiophora brassicae; Rhizoctonia species, such as Lithocarpus Rhizoctonia solani; Sarocladium species, eg Sarocladium oryzae; Sclerotium species, eg Sclerotium oryzae; Eye spots Tapesia species, eg Tapesia acuformis; Thielaviopsis species, eg Thielaviopsis basicola;

Ear and panicle diseases (including corn cobs) caused by, for example, Alternaria species, such as Alternaria spp.; Aspergillus species, such as Yellow Koji Bacteria; Cladosporium species such as Cladosporium cladosporioides; Claviceps species such as Claviceps purpurea; Fusarium species , eg Fusarium culmorum; Gibberella species, eg Gibberella zeae; Monographella species, eg Monographella nivalis ); Stagnospora species such as Stagnospora nodorum;

Diseases caused by the following smut fungi: e.g. Sphacelotheca species, e.g. Sphacelotheca reiliana; Tilletia species, e.g. wheat Tilletia caries or Tilletia controversa; Urocystis species) such as Urocystis occulta; Ustilago species such as Ustilago nuda;

Fruit rot caused, for example, by: Aspergillus species, such as Yellow yeast; Botrytis species, such as Botrytis cinerea; Monilinia species , such as Monilinia laxa; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Rhizopus species, such as Rhizopus stolonifera ( Rhizopus stolonifera); Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species, such as Verticilium alboatrum;

Seed- and soil-borne rot and wilt diseases, as well as seedling diseases, caused by, for example: Alternaria species, eg Alternaria brassicicola; Aphanomyces species , e.g. Aphanomyces euteiches; Ascochyta species, e.g. Ascochyta lentis; Aspergillus species, e.g. Aspergillus; Mycospores Cladosporium species, eg Cladosporium herbarum; Cochliobolus species, eg Cochliobolus sativus (Conidium form: Drexosporum) (Drechslera), Bipolaris, synonyms: Helminthosporium); Colletotrichum species, e.g. Colletotrichum coccodes; Alternaria (Fusarium species, such as Fusarium culmorum); Gibberella species, such as Gibberella zeae; Macrophomina phaseolina); Microdochium species, e.g. (Microdochium nivale); Monographella species, eg Monographella nivalis; Penicillium species, eg Penicillium expansum; Phoma species) such as Phoma lingam; Phomopsis species such as Phomopsis sojae; Phytophthora species such as Phytophthora cactorum ); Pyrenophora species, eg Pyrenophora graminea; Pyricularia species, eg Pyricularia oryzae; Pythium species, eg Ultimate Pythium ultimum; Rhizoctonia species, eg Rhizoctonia solani; Rhizopus species, eg Rhizopus oryzae; Sclerotium species), such as Sclerotium rolfsii); Septoria species, such as Septoria nodorum; Typhula species, such as Endosporium Typhula incarnata; Verticillium species such as Verticillium dahliae;

Carcinomas, root nodules and leaf cluster diseases caused by, for example, Nectria species, such as Nectria galligena;

Fusarium wilt caused by, for example, Verticillium species, such as Verticillium longisporum; Fusarium species, such as Fusarium oxysporum;

Leaf, flower and fruit deformities caused by, for example: Exobasidium species such as Exobasidium vexans; Taphrina species such as Taphrina deformans );

Degenerative diseases of woody plants caused by, for example: Esca species, for example Phaeomoniella chlamydospora, Acremonium (Phaeoacremonium aleophilum) or Fomitiporia mediterranea; Ganoderma species such as Ganoderma boninense;

Plant tuber diseases caused by, for example, Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani);

Diseases caused by bacterial pathogens such as Xanthomonas species, eg Xanthomonas campestris pv. oryzae; Pseudomonas species ), eg Pseudomonas syringae pv. lachrymans; Erwinia species, eg Erwinia amylovora; Liberibacter species, eg Liberibacter asiaticus ); Xyella species, such as Xylella fastidiosa; Ralstonia species, such as Ralstonia solanacearum; Dickya species, such as potato blackleg Dickya solani; Clavibacter species, eg Clavibacter michiganensis; Streptomyces species, eg Streptomyces scabies.

Soybean Diseases:

For example, fungal diseases on leaves, stems, pods and seeds caused by: Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Alternaria Colletotrichum gloeosporoides dematium var.truncatum), brown spot ( Septoria glycines ), cercospora leaf spot and blight (Cercospora kikuchi ( Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (soybean thrush Sclerotinia fungus (Dactuliophora glycines), Sclerotinia (Peronospora manshurica), Drexospora leaf blight (Drechslera glycini), Frogeye leaf spot (frogeye leaf spot) (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllosticta leaf spot) (Phyllosticta sojaecola), pod and stem blight (Pymphoma bean), powdery mildew (Microsphaera diffusa), Acanthospora leaf Pyrenochaeta leaf spot (Pyrenochaeta glycines), Rhizoctonia aerial (aerial) blight, leaf blight and blight (Rhizoctonia solani), rust (Pyramid yam) Rust fungus, Puccinia cordata), Scab (Sphaceloma glycines), Stemphylium leaf blight (Stemphylium botryosum), Sudden Death Syndrome (Fusarium rods) fungus (Fusarium virguliforme), ring spot (Corynespo ra cassiicola)).

Fungal diseases on roots and stem bases caused, for example, by: black root rot (Calonectria crotalariae), char rot (Macrophomina phaseolina), Fusarium leaf rot Blight or blight, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equisetum Fusarium equiseti), Mycoleptodiscus terrestris, Neocosmospora (Neocosmospora vasinfecta), Viburnum blight (M. terrestris) Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), blight rot (Phytophthora megasperma), brown stem rot (large Beanstalk brown rot (Phialophora gregata), Pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum), Pythium ultimum), Rhizoctonia root rot, stem rot, and damping off (R. solani), Sclerotinia sclerotiorum stem decay (Sclerotinia sclerotiorum), Sclerotinia white Silk disease (Sclerotinia rolfsii), Trichoderma root rot (Thielaviopsis basicola).

Mycotoxins

In addition, the compounds and compositions of the present invention can reduce the levels of mycotoxins in harvested material and foods and feeds prepared therefrom. Mycotoxins include in particular but not exclusively the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxins, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin , enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids ) and aflatoxins, which can be produced, for example, by the following fungi: Fusarium spec., such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (G. maize ( Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. stratum (F.proliferatum), Fusarium bluegrass (F.poae), Wheat crown rot fungus (F.pseudograminearum), Fusarium elderberry (F.sambucinum), Fusarium spp. (F.scirpi), semi-naked Fusarium (F. semitectum), Solanum F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. (F. tricinctum), F. verticillioides, and Aspergillus spec., such as A. flavus, A. parasiticus, A. parasiticus (A.nomius), A.ochraceus, A.clavatus, A.terreus, A.versicolor, Penicillium spec. ), such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. claviforme Molds (P. roqueforti), Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec. and others.

material protection

The compounds and compositions of the present invention can also be used for the protection of materials, especially for the protection of industrial materials from attack and destruction by phytopathogenic fungi.

In addition, the compounds and compositions of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

Industrial material is understood herein to mean inanimate material prepared for industrial use. For example, industrial materials to be protected from microbial alteration or destruction can be adhesives, viscose, paper, wallpaper and cardboard/cardboard, textiles, carpets, leather, wood, fibers and tissues, coatings and plastics, cooling lubricants and Other materials that can be infected or destroyed by microorganisms. Within the scope of the material to be protected mention may also be made of parts of production plants and buildings that can be damaged by the proliferation of microorganisms, such as cooling water circuits, cooling and heating systems and ventilation and air conditioning units. Industries within the Scope of the Invention Materials preferably include adhesives, glues, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

The compounds and compositions of the present invention prevent adverse effects such as spoilage, decay, discoloration, discoloration or mold formation.

In the case of wood treatment, the compounds and compositions of the present invention may also be used to combat fungal diseases that tend to grow on or in wood.

Wood means all types of wood species, and all types of processing for which such wood is intended for construction, such as solid wood, high density wood, laminated wood, and plywood. In addition, the compounds and compositions of the present invention can be used to protect objects in contact with salt water or brackish water, especially ship hulls, screens, fishing nets, buildings, moorings and signalling systems, from fouling.

The compounds and compositions of the present invention may also be used to protect stored goods. Storage goods are understood to mean natural substances of vegetable or animal origin or their processed products of natural origin and requiring long-term protection. Stored goods of vegetable origin (for example plants or plant parts such as stems, leaves, tubers, seeds, fruits, grains) may be protected immediately after harvest or may be Protect after pressing or baking. Stored goods also include both lumber, raw (such as construction lumber, utility poles, and fences) or in the form of final products (such as furniture). Stored goods of animal origin are, for example, hides, leathers, furs and hairs. The compounds and compositions of the present invention prevent adverse effects such as spoilage, decay, discoloration, discoloration or mold formation.

Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeast, algae, and slime organisms. The compounds and compositions of the present invention are preferably directed against fungi (especially moulds), wood discolouration and wood destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes). Zygomycetes)), and works against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Koji (Aspergillus), such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; 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., Paecilomyces spp., Mucor spp., Escherichia, such as Escherichia coli ( Escherichia coli); Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp., and Saccharomyces spp., such as Saccharomyces cerevisae.

seed treatment

The compounds and compositions of the present invention can also be used to protect seeds from undesired microorganisms (such as phytopathogenic microorganisms, eg, phytopathogenic fungi or phytopathogenic oomycetes). The term seed as used herein includes dormant seeds, osmotic-conditioned seeds, pre-germinated seeds, and seeds with germinated roots and leaves.

Accordingly, the present invention also relates to a method of protecting seeds from unwanted microorganisms comprising the step of treating the seeds with a compound or composition of the present invention.

Treatment of seeds with the compounds or compositions of the present invention protects the seeds from phytopathogenic microorganisms, and also protects germinated seeds, germinated seedlings, and plants after germination from the treated seeds. Accordingly, the present invention also relates to a method of protecting seeds, germinated seeds and germinated seedlings.

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

When the seed treatment is carried out before sowing (eg so-called on-seed application), the seed treatment can be carried out by placing the seed in a mixer with the desired amount of the compound or composition of the invention, mixing the seed with the invention The compound or composition is mixed until uniform distribution on the seed is achieved. If appropriate, the seeds can then be dried.

The present invention also relates to a seed coated with a compound or composition of the present invention.

Preferably, the seed lines are treated in a state in which they are sufficiently stable that no damage occurs during treatment. In general, the seeds can be treated at any time between harvest and a period of time after sowing. It is customary to use seeds that have been isolated from the plant and do not contain cobs, shells, stalks, epidermis, hairs or the pulp of the fruit. For example, it is also possible to use seeds that have been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that have been dried (e.g. have been treated with water and then dried again), or have been primed, or have been stored under primed conditions, or have been pregerminated, Or seeds sown on seedling trays, seedling tapes or seedling paper.

The amount of the compound or composition of the present invention applied to the seed is generally such that the germination of the seed is not damaged, or the resulting plant is not damaged. This must be ensured in particular where the compounds of the invention will exhibit phytotoxic effects at specific application rates. The inherent phenotype of transgenic plants should also be taken into account when determining the amount of the compounds of the present invention to be applied to seed for optimal seed and germinating plant protection with the least amount of compound used.

The compounds of the present invention can be applied directly to the seed as such, ie without using any other components and undiluted. Furthermore, the composition of the present invention can also be applied to seeds.

The compounds and compositions of the present invention are suitable for protecting the seeds of any plant species. Preferred seeds are cereals (such as wheat, barley, rye, millet, triticale, and oats), canola, corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, peas, sugar beets (such as sugar beets and forage beets) ), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), seeds of lawn and ornamental plants. More preferred are the seeds of wheat, soybean, rape, corn and rice.

The compounds and compositions of the present invention can be used to treat transgenic seeds, especially plant seeds capable of expressing polypeptides or proteins that act against pests, herbicide damage or abiotic stress, thereby increasing the protective effect. Plant seeds capable of expressing a polypeptide or protein that act on pests, herbicide damage, or abiotic stress may contain at least one heterologous gene that allows expression of the polypeptide or protein. Such heterologous genes in transgenic seeds can be derived from, for example, Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma Microorganisms of the genus Trichoderma, Clavibacter, Glomus or Gliocladium. These heterologous genes are preferably derived from Bacillus sp., in which case the gene product is effective against European corn borer and/or Western corn rootworm. Particularly preferably, the heterologous genes are derived from Bacillus thuringiensis.

administer

The compounds of the invention can be concentrated as such or, for example, as ready-to-use solutions, emulsions, aqueous or oily suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for spreading, suspoemulsions It is applied in the form of substances, natural products impregnated with the compounds of the present invention, synthetic substances impregnated with the compounds of the present invention, fertilizers or microencapsulated in polymers.

Application is accomplished in a conventional manner, eg, by watering, spraying, atomizing, sowing, dusting, foaming, dusting. It is also possible to formulate the compounds of the present invention by ultra-low volume methods via drip irrigation systems or wet application to apply them in furrows or inject them into soil stems or tree trunks. It is also possible to apply the compounds of the invention by means of wrap seals, paints or other wrap dressings.

The effective and phytocompatible amount of a compound of the present invention applied to a plant, plant part, fruit, seed or soil will depend on various factors, such as the compound/composition used, the subject of the treatment (plant, plant part, fruit, seed or soil), type of treatment (dusting, spraying, companion seeding), purpose of treatment (healing and protection), type of microorganisms, stage of development of microorganisms, susceptibility of microorganisms, stage of crop growth and environmental conditions.

When using the compounds of the present invention as fungicides, the application rate can be varied within wide limits, depending on the type of application. For the treatment of plant parts such as leaves, application rates may range from 0.1 to 10000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of watering or drip application) , especially when using inert substrates such as rock wool or perlite, it is even possible to reduce the application rate). For the treatment of seed, application rates may range from 0.1 to 200 g per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed. For soil treatment, application rates may range from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.

These application rates are examples only and are not intended to limit the scope of the invention.

The compounds and compositions of the present invention can be used in combination with models, such as embedded in computer programs for site-specific crop management, satellite farming, precision farming, or precision agriculture. The models are based on data from various sources such as soil, weather, crops (eg type, growth stage, plant health), weeds (eg type, growth stage), diseases, pests, nutrients, water, moisture, biomass, Satellite data, yields, etc. support location-specific management of agricultural locations with the aim of optimizing Environmental profitability, sustainability and protection. In particular, these models can help optimize agronomic decisions, control the precision of pesticide application, and document work done.

As an example, if the model simulates the development of a fungal disease and the calculation has reached a threshold at which application of the compounds of the invention to crop plants is recommended, the compounds of the invention can be applied to crop plants according to an appropriate dosage regimen.

Commercially available systems including agronomic models are eg FieldScripts ^™ from The Climate Corporation, Xarvio ^™ from BASF, AGLogic ^™ from John Deere.

The compounds of the present invention may also be used with intelligent spraying equipment such as, for example, spot spraying attached to or mounted in agricultural vehicles such as tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs) such as drones, etc. or in combination with precision spraying equipment. Such equipment typically includes an input sensor (such as a camera) and a processing unit configured to analyze the input data and to provide decisions based on the analysis of the input data, in a specific and precise manner. The compounds of the present invention are applied to crop plants (individual weeds). The use of such intelligent spraying equipment usually also requires positioning recorded data and a positioning system (such as a GPS receiver) for guiding or controlling agricultural vehicles; The map presents the geographic information system (GIS) of the information and the appropriate agricultural vehicles to perform the required farm actions such as spraying.

In one example, fungal disease can be detected from imagery acquired from a camera. In one example, fungal diseases can be identified and/or classified based on images. Such identification and/or classification may utilize image processing algorithms. Such image processing algorithms may utilize machine learning algorithms, such as trained neural networks, decision trees, and algorithms utilizing artificial intelligence. In this manner, only the compounds described herein can be administered when necessary.

Aspects of the present teachings can be further understood in light of the following examples, which should not be construed in any way to limit the scope of the present teachings.

Example

Introduction

Measurement of LogP Values

The measurements of the LogP values provided herein were carried out by HPLC (High Performance Liquid Chromatography) on a reverse column according to EEC Directive 79/831 Annex V.A8 using the following method:

^[a] LogP values were measured by LC-UV in the acidic range using 0.1% formic acid/water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

^[b] LogP values were measured by LC-UV in the neutral range using 0.001 molar ammonium acetate solution/water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile) .

^[c] LogP values were measured by LC-UV in the acidic range using 0.1% phosphoric acid and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

If more than one LogP value can be obtained in the same method, all values are given and separated by "+".

Calibration is performed on linear alkan-2-ones (having 3 to 16 carbon atoms) with known LogP values (measured by linear interpolation between successive alkanones using residence time). The λ-maxima were determined using the peaks of the UV-spectral and chromatographic signals from 200 nm to 400 nm.

¹ H-NMR data

¹ H NMR data for selected examples as provided herein are written as a list of ¹ H NMR peaks. For each signal peak, the delta value is listed in ppm and the signal strength in parentheses. The delta value-signal strength pair is separated by a semicolon.

An example peak list thus has the following form:

δ ₁ (intensity ₁ ); δ ₂ (intensity ₂ ); ...; δ _i (intensity _i ); ...; δ _n (intensity _n )

The intensity of the sharp signal in the printed example of the NMR spectrum (in cm) is related to the height of the signal and shows the true relationship of the signal intensity. From a broad signal, several peaks or signal middles and their relative intensities compared to the strongest signal in the spectrum can be displayed.

To correct the chemical shifts of the ¹ H NMR spectra, we used the chemical shifts of tetramethylsilane and/or the solvent used, especially if the spectra were measured in dimethylsulfoxide (DMSO). Therefore, in the NMR peak list, the tetramethylsilane peak can appear but not necessarily.

The ¹ H-NMR peak list series is similar to the classical NMR print and therefore generally contains all peaks listed in the classical NMR interpretation.

In addition they may show classical ¹ H-NMR print signals of peaks such as solvents, stereoisomers that are also subject compounds of the invention, and/or impurities.

To show compound signals in the delta range of solvents and/or water, peaks for common solvents such as in DMSO-D ₆ for DMSO and for water are shown in our ¹ H-NMR peak list and are usually averaged Has high strength.

The peaks of stereoisomers of the target compound and/or the peaks of impurities typically have lower intensity on average than the target compound (eg, with >90% purity).

Such stereoisomers and/or impurities may be representative of specific preparation methods. Their peaks can thus help identify the reproducibility of our preparation method via a "by-product fingerprint".

Experts calculating the peaks of the target compound in known methods (MestreC, ACD-simulations, but also using empirically estimated expectations) can optionally use additional intensity filters to separate out the peaks of the target compound. This separation would be analogous to the associated peak picking of classical1H ^- NMR interpretation.

Further details on NMR data descriptions and peak listings can be found in the publication Research Disclosure Database Number 564025 In "Citation of NMR Peaklist Data within Patent Applications".

The following examples illustrate, in a non-limiting manner, the preparation and biological activity of compounds of formula (I) according to the present invention.

Synthesis of compounds of formula (I)

Table 1 does not illustrate, in a non-limiting manner, examples of compounds of formula (I) according to the present invention:

The compounds of formula (I) referred to in Table 1 herein below were prepared according to the procedures detailed below for specific examples and general descriptions of the methods disclosed herein.

In Table 1, logP values are determined according to method ^[a] .

Table 1:

Table 2 provides NMR data ( ¹ H) for selected numbered compounds from Table 1 .

Table 2: List of NMR peaks

Preparation example

二唑-2-基]嘧啶-2-基}胺基)-3-(2-氟苯基)環丁醇(化合物I.003) Preparation Example 1: cis-3-({5-[5-(difluoromethyl)-1,3,4-

Diazol-2-yl]pyrimidin-2-yl}amino)-3-(2-fluorophenyl)cyclobutanol (Compound I.003)

Step 1: Preparation of 2-Chloro-N'-(difluoroacetyl)pyrimidine-5-carbohydrazide

A solution of 41.0 g of 2,2-difluoroacethydrazine (373 mmol) in 30 mL of tetrahydrofuran was slowly added to 33.0 g of 2-chloropyrimidine-5-carbonyl chloride (187 mmol) under nitrogen at -60°C A solution in 300 mL of dichloromethane. The reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction mixture was concentrated under reduced pressure to provide 233 g (quantitative yield) of the title compound as a white solid. The product was used in the next step without further purification.

二唑-2-基]-嘧啶的製備 Step 2: 2-Chloro-5-[5-(difluoromethyl)-1,3,4-

Preparation of oxadiazol-2-yl]-pyrimidine

87.5 g of p-toluenesulfonyl chloride (459 mmol) followed by 128 mL of triethylamine (918 mmol) were slowly added to 46.0 g of 2-chloro-N'-(difluoroacetamide under nitrogen at -20°C ) pyrimidine-5-carbohydrazide (184 mmol) in 400 mL of acetonitrile and 50 mL of N,N-dimethylformamide. The reaction mixture was stirred at -20°C for 3 hours. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (gradient petroleum ether/ethyl acetate) on silica gel followed by trituration with tertiary butyl methyl ether at 20°C for 3 hours to yield 100 g (100% purity, 47% yield). rate) of the title compound as an off-white solid.

二唑-2-基]嘧啶-2-基}胺基)-3-(2-氟苯基)環丁醇(化合物I.003)的製備 Step 3: cis-3-({5-[5-(difluoromethyl)-1,3,4-

Preparation of oxadiazol-2-yl]pyrimidin-2-yl}amino)-3-(2-fluorophenyl)cyclobutanol (compound 1.003)

二唑-2-基]-嘧啶在5mL的1,4-二

烷中之溶液。將反應混合物在105℃下攪拌18小時。將所得混合物冷卻至室溫，用水稀釋並用乙酸乙酯萃取。將合併的有機萃取物用無水硫酸鎂乾燥，過濾並在減壓下濃縮。將殘餘物藉由管柱層析法在矽膠上(正庚烷/乙酸乙酯)純化以產生620mg(98%純度，94%產率)的呈黃色固體之標題化合物。LogP=2.11[方法A]。質量(M+H)=378。 1.20 mL (6.88 mmol) of N,N-diisopropylethylamine was added to 393 mg (1.80 mmol) of cis-3-amino-3-(2-fluorophenyl)cyclobutanol and 400 mg under argon (1.72 mmol) of 2-chloro-5-[5-(difluoromethyl)-1,3,4-

oxadiazol-2-yl]-pyrimidine in 5 mL of 1,4-bis

solution in alkane. The reaction mixture was stirred at 105°C for 18 hours. The resulting mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-heptane/ethyl acetate) to give 620 mg (98% purity, 94% yield) of the title compound as a yellow solid. LogP=2.11 [Method A]. Mass (M+H)=378.

二唑-2-基]嘧啶-2-基}胺基)-3-(2-氟苯基)環丁基酯(化合物I.002) Preparation Example 2: cis-3-({5-[5-(difluoromethyl)-1,3,4-acetic acid)

Diazol-2-yl]pyrimidin-2-yl}amino)-3-(2-fluorophenyl)cyclobutyl ester (Compound I.002)

二唑-2-基]嘧啶-2-基}胺基)-3-(2-氟苯基)環丁醇(化合物I.003)和69μL(0.39mmol)的N,N-二異丙基 乙胺在1.5mL的乾燥四氫呋喃中之溶液。將反應混合物在室溫下攪拌4.5小時。滴加額外的25mg(0.31mmol)的乙醯氯並將反應混合物在室溫下攪拌18小時。將所得混合物用水稀釋並用乙酸乙酯萃取3次。將合併的有機萃取物用飽和碳酸氫鈉之水溶液、鹽水洗滌，用無水硫酸鎂乾燥，過濾並在減壓下濃縮。將殘餘物藉由管柱層析法在矽膠上(正庚烷/乙酸乙酯)純化以產生44mg(97%純度，38%產率)的呈白色固體之標題化合物。LogP=2.94[方法A]。質量(M+H)=420。 25 mg (0.31 mmol) of acetyl chloride was added dropwise to 100 mg (0.26 mmol) of 1cis-3-({5-[5-(difluoromethyl)-1,3,4- at 0°C

oxadiazol-2-yl]pyrimidin-2-yl}amino)-3-(2-fluorophenyl)cyclobutanol (Compound I.003) and 69 μL (0.39 mmol) of N,N-diisopropyl A solution of ethylamine in 1.5 mL of dry tetrahydrofuran. The reaction mixture was stirred at room temperature for 4.5 hours. An additional 25 mg (0.31 mmol) of acetyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 18 hours. The resulting mixture was diluted with water and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-heptane/ethyl acetate) to give 44 mg (97% purity, 38% yield) of the title compound as a white solid. LogP=2.94 [Method A]. Mass (M+H)=420.

Light Stability Data

Measurement of UV stability, reported as photodegradation half-life, was performed by irradiating the sample for 24 h with the available full UV/VIS spectrum of SUNTEST XLS+ running from 250 nm to 800 nm, followed by using UV-detection coupled to single quadrupole mass spectrometry using the following method Analytes and their possible degradation products are analyzed by reversed-phase liquid chromatography of the instrument:

Analytes were determined by LC-UV-MS with 0.085% (v/v) formic acid/water and 0.1% (v/v) formic acid in acetonitrile as eluents (linear from 5% acetonitrile to 95% acetonitrile) .

Analytes were identified and determined via UV and MS spectroscopy. Half-life was measured over the course of 5 time points of 0h, 2h, 4h, 6h and 24h, with triplicates for each time point. All time points were normalized to detector responses received at 0 h. Half-life is determined by fitting the results to a ^1st order degradation function and returned in units [h].

Table 3 provides half-lives for selected numbered compounds from Table 1 and some reference compounds known from WO2019/122323. The following compounds are used as reference examples:

二唑-3-基]嘧啶-2-胺 Reference 1: N-[1-(2-pyridyl)cyclobutyl]-5-[5-(trifluoromethyl)-1,2,4-

oxadiazol-3-yl]pyrimidin-2-amine

二唑-3-基]嘧啶-2-胺 Reference 2: N-(1-phenylcyclopropyl)-5-[5-(trifluoromethyl)-1,2,4-

oxadiazol-3-yl]pyrimidin-2-amine

table 3:

biological example

Example: In vivo preventive testing against Puccinia recondita (brown rust on wheat)

Solvent: 5% by volume of dimethyl sulfoxide

10 vol% acetone

Emulsifier: 1 μl of polyoxyethylene sorbitan monooleate (Tween ^® 80) per mg of active ingredient

The active ingredient was dissolved and homogenized in a mixture of dimethylsulfoxide/acetone// ^Tween® 80 and then diluted with water to the desired concentration.

Seedlings of wheat are treated by spraying with the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethylsulfite/Tween ^® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The infected wheat plants were incubated at 20°C and 100% relative humidity for 24 hours and then at 20°C and 70-80% relative humidity for 10 days.

The test was assessed 10 days after inoculation. 0% means efficacy corresponding to control plants, while 100% efficacy means no disease is observed.

In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1.003; 1.006

In this test, the following compounds according to the invention showed an efficacy between 70% and 79% at a concentration of 250 ppm of active ingredient: I.004; I.011

In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 250 ppm of active ingredient: I.001; I.013; I.014; I.016

In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I.007; I.010; I.012; I.018

Example: In vivo preventive testing against Phakospora pachyrhizi (soybean rust)

Solvent: 5% by volume of dimethyl sulfoxide

10 vol% acetone

Emulsifier: 1 μl of polyoxyethylene sorbitan monooleate (Tween ^® 80) per mg of active ingredient

The active ingredient was dissolved and homogenized in a mixture of dimethylsulfoxide/acetone// ^Tween® 80 and then diluted with water to the desired concentration.

Soybean seedlings are treated by spraying with the active ingredient prepared as described above. Control plants were treated with an aqueous solution of acetone/dimethylsulfite/Tween ^® 80 only.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of Phakospora pachyrhizi spores. Contaminated soybean plants were incubated at 20°C and 100% relative humidity for 24 hours and then at 20°C and 70-80% relative humidity for 10 days.

The test was assessed 11 days after vaccination. 0% means efficacy corresponding to control plants, while 100% efficacy means no disease is observed.

In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1.003; 1.006

In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 250 ppm of active ingredient: 1.005; 1.008; 1.009; 1.011

In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I.001; I.002; I.004; I.007; I. 012;I.013;I.014;I.016;I.017;I.018

Example: In vivo prophylactic test against Phakospora pachyrhizi (soybean)

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To produce a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for prophylactic activity, young plants are sprayed with the preparation of active compound at the stated application rates. After the spray coating has dried, the plants are inoculated with an aqueous spore suspension of the causative agent of soybean rust (Phakopsora pachyrhizi) and grown in an incubator at about 24°C and 95% relative atmospheric humidity Stand in the dark for 24 hours.

Plants are maintained in an incubation cabinet at a temperature of about 24°C and a relative atmospheric humidity of about 80% with a day/night interval of 12 hours.

The test was assessed 7 days after inoculation. 0% means efficacy corresponding to the untreated control group, while 100% efficacy means no disease is observed.

Example: In Vivo Healing Test Against Phakopsora (Soybean)

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethyl sulfoxide

Emulsifier: 1 part by weight of polyethoxyethylene sorbitan monooleate

To produce a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for curative activity, plants were inoculated with an aqueous spore suspension of the causative agent of soybean rust (Phakopsora pachyrhizi) and incubated without light in an incubation cabinet at about 24°C and 95% relative atmospheric humidity Let stand for 24h.

Plants were maintained in an incubation cabinet at about 24°C and a relative atmospheric humidity of about 80% with a day/night interval of 12 h.

Plants are sprayed with the formulation of active compound at the stated application rates 2 days after inoculation and further maintained in the incubation cabinet.

The test was assessed 7 days after inoculation. 0% means efficacy corresponding to the untreated control group, while 100% efficacy means no disease is observed.

Example: In vivo long-acting activity test against layer rust (soybean)

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethyl sulfoxide

Emulsifier: 1 part by weight of polyethoxyethylene sorbitan monooleate

To produce a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for long-term activity, young plants are sprayed with the formulation of active compound at the stated application rates. After the spray coating has dried, the plants are placed in an incubation cabinet at about 24°C and a relative atmospheric humidity of about 80% with a 12 h day/night interval.

Eight days after application, plants were inoculated with an aqueous spore suspension of the causative agent of soybean rust (Phakopsora pachyrhizi) and kept free in an incubator at about 24°C and 95% relative atmospheric humidity. The light was left to stand for 24h.

Plants were maintained in an incubation cabinet at about 24°C and a relative atmospheric humidity of about 80% with a day/night interval of 12 h.

The test was assessed 7 days after inoculation. 0% means efficacy corresponding to the untreated control group, while 100% efficacy means no disease is observed.

Example: In vivo prophylactic Puccinia triticina test (wheat)

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethyl sulfoxide

Emulsifier: 1 part by weight of polyethoxyethylene sorbitan monooleate

To produce a suitable formulation of the active compound, 1 part by weight of the active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for prophylactic activity, young plants are sprayed with the formulation of active compound or active compound combination at the stated application rate.

After the spray coating had dried, the plants were sprayed with a spore suspension of Puccinia triticina. Plants are maintained for 48 hours in an incubator at about 20°C and a relative atmospheric humidity of about 100%.

Plants are placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80%.

The test was assessed 8 days after inoculation. 0% means efficacy corresponding to the untreated control group, while 100% efficacy means no disease is observed.

Claims (15)

A compound of formula (I):

in X is hydrogen or fluorine; R ¹ and R ² together with the carbon atom to which they are attached form a C ₃ -C ₅ -cycloalkyl group, wherein the C ₃ -C ₅ -cycloalkyl group is substituted with one or more R ^1b substituents; ^R is aryl or heteroaryl, wherein the aryl and heteroaryl may be substituted with one or more R ^substituents ; R ^1b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfanyl, pentafluoro-λ ⁶ -sulfanyl, carboxyl, carbamoyl Acyl, urethane, _C1 -C8 _- alkyl, C3-C7-cycloalkyl, _{C1 -} C8-haloalkyl with ₁ to ₅ halogen atoms, with 1 to 5 C ₃ -C ₇ -halocycloalkyl of halogen atoms, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C _{8 -Alkyl} )-N-(C3 _- C7 _- cycloalkyl)amino, C3 _- C7-cycloalkylamino, di-( _{C1 -} C8 _- alkyl)amino, C1- C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 C ₁ -C 8 -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C 1 -C _{8 -alkanecarbonyl with 5 halogen atoms, C 1 -C 8 - with 1} to 5 halogen atoms Haloalkanecarbonyl, C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylaminocarboxy, C ₃ -C ₇ -cycloalkylaminocarboxy, N-(C ₁ -C ₈ - Alkyl)-N-(C ₃ -C ₇ -cycloalkyl)aminocarboxyl, di-(C ₁ -C ₈ -alkyl)aminocarboxyl, C ₁ -C ₈ -alkoxycarbonyl, with C ₁ -C ₈ -haloalkoxycarbonyl with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ with 1 to 5 halogen atoms -C ₈ -haloalkcarbonyloxy, C ₃ -C ₇ -cycloalkanecarbonyloxy, C ₁ -C ₈ -alkanecarbonylamino, C ₁ -C ₈ -haloalkanecarbonyl with 1 to 5 halogen atoms Amine, C3 _- C7-cycloalkanecarbonylamino, _C1 -C8 _- alkoxycarbonylamino, C1 _{- C8} -haloalkoxycarbonylamino with ₁ to ₅ halogen atoms, C3 -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkylsulfinyl, C ₁ -C ₈ -haloalkylsulfinyl with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -ring Alkylsulfonamido, _C1 -C8-alkylsulfonamido, C1 _{- C8 -} haloalkylsulfonamido with ₁ to ₅ halogen atoms, C3-C7-cycloalkyl sulfonamido, arylsulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfamoyl, C ₃ -C ₇ -cycloalkyl sulfamoyl and bis-(C ₁ -C8-Alkyl) _sulfamoyl ; and/or The two geminal R ^1b substituents may together with the carbon atom to which they are attached form a C ₃ -C ₇ -cycloalkyl or 3- to 7-membered heterocyclyl, or The two twin R ^1b substituents may together with the carbon atom to which they are attached form a C=O, C=CH ₂ or C=NO-(C ₁ -C ₈ -alkyl) group; R ^3b is selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amine, sulfhydryl, pentafluoro-λ ⁶ -sulfhydryl, carboxyl, carbamoyl, Carbamates, C ₁ -C ₈ -alkyl, C ₃ -C ₇ -cycloalkyl, C 1 -C 8 -haloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -haloalkyl with 1 to 5 halogen atoms C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₈ -alkylamino, N-(C ₁ -C ₈ -alkyl )-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ - Alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with 1 to 5 halogen Atoms C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl, C ₁ -C ₈ -haloalkylcarbonyl with 1 to 5 halogen atoms , C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylamine carboxyl, C ₃ -C ₇ -cycloalkylamine carboxyl, N-(C ₁ -C ₈ -alkyl) -N-(C ₃ -C ₇ -cycloalkyl)aminocarboxy, di-(C ₁ -C ₈ -alkyl)carbamoyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 C ₁ -C ₈ -haloalkoxycarbonyl with halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, C ₁ -C ₈ with 1 to 5 halogen atoms -Haloalkanecarbonyloxy, C3-C7-cycloalkanecarbonyloxy, _{C1 -} C8 _- alkanecarbonylamino, _C1 -C8-haloalkanecarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonylamino, C ₁ -C ₈ -alkoxycarbonylamino, C ₁ -C ₈ -haloalkoxycarbonylamino with 1 to 5 halogen atoms, C ₃ -C ₇ -Cycloalkoxycarbonylamino, _C1 -C8-alkylsulfinyl, C1 _{- C8 -} haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3-C7-ring Alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms; C ₃ -C ₇ -cycloalkylsulfonyl Acyl, C ₁ -C ₈ -alkylsulfonamido, C ₁ -C ₈ -haloalkylsulfonamido with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkylsulfonamido sulfonamido, arylsulfonamido, sulfamoyl; C ₁ -C ₈ -alkyl sulfonamido, C ₃ -C ₇ -cycloalkyl sulfonamido and di-(C ₁ -C ₈ - alkyl wherein the C ₁ -C ₈ -alkyl group may be substituted with one or more R ^x substituents; R ^x is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amine, thiol, pentafluoro-λ ⁶ -thiol, carboxyl, carbamoyl, Carbamates, C ₃ -C ₇ -cycloalkyl, C ₃ -C ₇ -halocycloalkyl with 1 to 5 halogen atoms, C ₁ -C ₈ -alkylamino, N-(C ₁ - C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl)amino, C ₃ -C ₇ -cycloalkylamino, di-(C ₁ -C ₈ -alkyl)amino, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxy, C ₁ -C ₈ -alkylthio, with C ₁ -C ₈ -haloalkylthio, C ₃ -C ₇ -cycloalkylthio, C ₁ -C ₈ -alkylcarbonyl with 1 to 5 halogen atoms, C ₁ -C with 1 to 5 halogen atoms ₈ -Haloalkanecarbonyl, C ₃ -C ₇ -cycloalkanecarbonyl, C ₁ -C ₈ -alkylaminecarboxyl, C ₃ -C ₇ -cycloalkylaminecarboxyl, N-(C ₁ -C ₈ -Alkyl)-N-(C ₃ -C ₇ -cycloalkyl) carbamoyl, di-(C ₁ -C ₈ -alkyl) carbamoyl, C ₁ -C ₈ -alkoxycarbonyl , C ₁ -C ₈ -haloalkoxycarbonyl with 1 to 5 halogen atoms, C ₃ -C ₇ -cycloalkoxycarbonyl, C ₁ -C ₈ -alkoxycarbonyl, with 1 to 5 halogen atoms C ₁ -C ₈ -haloalkanecarbonyloxy, C ₃ -C ₇ -cycloalkanecarbonyloxy, C ₁ -C ₈ -alkanecarbonylamino, C ₁ -C ₈ -haloalkanes with 1 to 5 halogen atoms Carbonylamino, C3-C7-cycloalkanecarbonylamino, _{C1 -} C8 _- alkoxycarbonylamino, C1- _C8 -haloalkoxycarbonylamino with ₁ to ₅ halogen atoms, C ₃ -C7-cycloalkoxycarbonylamino, _{C1 -} C8-alkylsulfinyl, C1 _{- C8} -haloalkylsulfinyl with ₁ to ₅ halogen atoms, C3- C ₇ -cycloalkylsulfinyl, C 1 -C ₈ -alkylsulfonyl, C ₁ -C ₈ -haloalkylsulfonyl with 1 to 5 halogen atoms _{; C 3 -C 7} - Cycloalkylsulfonamido, _C1 -C8-alkylsulfonamido, C1 _{- C8 -} haloalkylsulfonamido with ₁ to ₅ halogen atoms, C3-C7-cycloalkane sulfonamido, sulfamoyl, C ₁ -C ₈ -alkyl sulfamoyl and di-(C ₁ -C ₈ -alkyl) sulfamoyl; or its salt, N-oxide or solvate. A compound of formula (I) according to claim 1 or a salt, N-oxide or solvate thereof, wherein the R ^1b substituent is selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ -alkane radicals, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkcarbonyloxy and C ₁ -C ₄ - Haloalkoxy, and/or two twin R ^1b substituents together form -O-(CH ₂ ) ₂ -O- or -O-(CH ₂ ) ₃ -O- group or two twin R ^1b substituents The groups together with the carbon atoms to which they are attached form a C=O group. A compound of formula (I) according to claim 1 or 2, or a salt, N-oxide or solvate thereof, wherein the C3 _{- C5} -cycloalkyl ring is a cyclopropyl or cyclobutyl ring, which is One to three R ^1b substituents are substituted. A compound of formula (I) according to any one of the preceding claims, or a salt, N-oxide or solvate thereof, wherein the C3 _{- C5} -cycloalkyl ring system is one or two selected from the group consisting of Substituent substitutions for R ^1b of the group: fluoro, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy. A compound of formula (I) or a salt, N-oxide, or solvate thereof according to any one of the preceding claims, wherein X is hydrogen. A compound of formula (I) according to any one of the preceding claims, or a salt, N-oxide or solvate thereof, wherein the aryl or heteroaryl group may be substituted with one to three ^R3b substituents independently selected from Substituted: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 halogen atoms, C ₁ - _C4 -alkoxy, _C1 - _C4 -haloalkoxy and _C1 - _C4 -alkoxycarbonyl having 1 to 5 halogen atoms. A compound of formula (I) according to any one of the preceding claims, or a salt, N-oxide or solvate thereof, wherein the aryl or heteroaryl group may be independently selected from the group consisting of one to three groups R ^3b Substituent substitution: fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, tributyl Fluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl. A compound of formula (I) according to any one of the preceding claims, or a salt, N-oxide or solvate thereof, wherein R ³ is phenyl, naphthyl or heteroaryl selected from the group consisting of furan base, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, iso

azolyl,

azolyl,

oxadiazolyl, isothiazolyl, thiazolyl, pyridyl, pyridyl

base, pyrimidinyl, pyridine

group, indolyl, isoindolyl, quinolinyl and isoquinolinyl. A compound of formula (I) or a salt, N-oxide or solvate thereof according to any one of the preceding claims, wherein R ³ is unsubstituted or substituted phenyl. A compound of formula (I) or a salt, N-oxide or solvate thereof according to claim 1, wherein X is hydrogen or fluorine; R ¹ and R ² together with the carbon atoms to which they are attached form a cyclobutyl or cyclopropyl ring, wherein the cyclobutyl or cyclopropyl ring is one to three R independently selected from the group consisting of ^1b Substituent substitution: fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoro Methyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl; and ^R is phenyl, which may be substituted with one to three R ^substituents independently selected from the group consisting of fluoro, chloro, bromo, nitro, cyano, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tertiary butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy , methoxycarbonyl, ethoxycarbonyl and tertiary butoxycarbonyl. A composition for controlling harmful microorganisms in crop protection, comprising at least one compound of formula (I) according to any one of claims 1 to 10 and at least one carrier and/or surfactant. Use of one or more compounds of formula (I) according to any one of claims 1 to 10 and/or a composition according to claim 11 for the control of harmful microorganisms in crop protection. A method for controlling harmful microorganisms in crop protection, characterized in that at least one compound of formula (I) according to any one of claims 1 to 10 or a composition according to claim 11 is applied to harmful microorganisms and/or or its habitat. A method for preparing a compound of formula (I) according to any one of claims 1 to 10, comprising the following steps (a) Preparation of a compound of formula (II)

wherein X, R ¹ , R ² and R ³ are as defined in compounds of formula (I) (a-1) by making a formula (III) carbohydrazide (carbohydrazide)

wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and (II), with a compound of formula (IV-a) or (IV-b),

wherein X is as defined in compounds of formula (I) and (II), in the presence of an organic solvent and optionally an organic base to produce a compound of formula (II), or (a-2) makes a compound of formula (V),

wherein LG1 is ^a leaving group and R1 and R2 are as defined in ^compounds of formula (I) and (II), with a compound of formula (IVc)

wherein X is as defined in compounds of formula (I) and (II), in the presence of an organic solvent and optionally in the presence of an organic base to produce a compound of formula (II), and (b) reacting the compound of formula (II) obtained in step (a-1) or (a-2) with a dehydrating agent in the presence of an organic solvent to produce the compound of formula (I). A compound of formula (II) or a salt, N-oxide or solvate thereof,

wherein R ¹ , R ² , R ³ and X are as defined for compounds of formula (I) in any one of claims 1 to 10.