Substituted oxadiazoles for controlling phytopathogenic fungi

Abstract

The present invention relates to novel trifluoromethyldiazoles of formula (I) or N-oxides and / or their agriculturally acceptable salts; to their use for controlling phytopathogenic fungi; to a method for controlling phytopathogenic harmful fungi, which comprises treating the fungi or the plants, soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I or an N-oxide or an agriculturally acceptable salt thereof; to agrochemical compositions comprising at least one of the compounds; and to agrochemical compositions further comprising seeds.

Description

[0001] This invention relates to novel trifluoromethyl compounds of formula I. Diazoles or N-oxides and / or their agriculturally usable salts; their use in controlling plant pathogenic fungi; a method for controlling plant pathogenic harmful fungi, the method comprising treating fungi or plants, soil or seeds to be protected against fungal invasion with an effective amount of at least one compound of formula I or its N-oxide or agriculturally usable salt; an agricultural chemical composition comprising at least one of the compounds; and an agricultural chemical composition further comprising seeds.

[0002] WO 2017 / 055469 A1 and WO 2017 / 055473 A1 describe trifluoromethyl Diazole derivatives and their use in controlling plant pathogenic microorganisms. WO 2015 / 185485 A1 describes trifluoromethyl... Similar derivatives of diazoles and their use in controlling plant pathogenic microorganisms. EP 276432 A2 relates to 3-phenyl-5-trifluoromethyl Diazole derivatives and their uses in controlling plant pathogenic microorganisms. WO 97 / 30047 A1 describes certain trifluoromethyl diazoles with fungicidal activity. diazole analogs, including trifluoromethyl The diazole group and amide functional group are connected to the phenyl ring in an ortho-ortho relationship.

[0003] In many cases, especially at low application rates, the fungicidal activity of known fungicides is unsatisfactory. Therefore, the object of this invention is to provide compounds with improved activity and / or a broader activity spectrum against plant pathogenic fungi. This object is achieved by [the following formula is missing from the original text]. The use of diazoles and / or their agriculturally usable salts in the control of plant pathogenic fungi has been realized.

[0004] Therefore, this invention relates to compounds of formula I or their N-oxides or agriculturally usable salts:

[0005]

[0006] in:

[0007] A is phenyl or thiophene; and wherein the cyclic group A is not substituted or is replaced by 1, 2, 3 or 4 identical or different groups R. A Replace; among them

[0008] R AThe derivative is OH, cyclopropyl, halogen, cyano, di-C1-C6 alkylamino, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkoxy; and any aliphatic or cyclic moiety thereof is unsubstituted or surrounded by 1, 2, 3, or 4 identical or different groups R. a Replace; among them

[0009] R a It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0010] R 1 R 2 Independently, these are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C1-C4 alkoxy, -C(=O)-(C1-C6 alkyl), -C(=O)-(C1-C6 alkoxy), phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, C3-C6 cycloalkyl-C1-C4 alkyl, phenyl, naphthyl, or 3-10 saturated, partially unsaturated, or aromatic monocyclic or bicyclic heterocycles, wherein the ring member atoms of the monocyclic or bicyclic heterocycle, in addition to carbon atoms, include 1, 2, ... The heterocyclic ring has 3 or 4 heteroatoms selected from N, O, and S as ring members, and 1 or 2 carbon ring members of the heterocyclic ring can be replaced by 1 or 2 groups independently selected from -C(=O)- and -C(=S)-; and the heteroaryl group in the heteroaryl-C1-C4 alkyl group is a 5 or 6-membered aromatic heterocycle, wherein the ring members of the heterocycle, in addition to the carbon atom, include 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring members; and any of the above aliphatic or cyclic groups is not substituted or is replaced by 1, 2, 3, or at most the maximum possible number of the same or different groups R. 1a replace;

[0011] Or R 1 and R 2 Together with the nitrogen atoms they are bonded to, they form saturated or partially unsaturated monocyclic or bicyclic 3-10 member heterocycles, wherein the heterocycle contains one, two, or three heteroatoms independently selected from N, O, and S as ring members, in addition to one nitrogen atom and one or more carbon atoms; and wherein one or two CH2 groups of the heterocycle can be replaced by one or two groups independently selected from the group consisting of -C(=O)- and -C(=S)-; and wherein the heterocycle is either unsubstituted or replaced by one, two, three, four, or at most the maximum possible number of identical or different groups R. 1a Replace; among them

[0012] R 1aHalogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl, -NHSO2-C1-C4 alkyl, -(C=O)C1-C4 alkyl, -C(=O)-C1-C4 alkoxy or C1-C6 alkyl Sulfonyl, hydroxy-C1-C4 alkyl, -C(=O)-NH2, -C(=O)-NH(C1-C4 alkyl), C1-C4 alkylthio-C1-C4 alkyl, amino-C1-C4 alkyl, C1-C4 alkylamino-C1-C4 alkyl, di-C1-C4 alkylamino-C1-C4 alkyl, aminocarbonyl-C1-C4 alkyl, or C1-C4 alkoxy-C1-C4 alkyl.

[0013] The agriculturally usable salts of Compound I particularly include salts of cations whose cations and anions do not adversely affect the fungicidal activity of Compound I, or acid addition salts of those acids. Suitable cations are therefore especially alkali metal ions, preferably sodium and potassium ions; alkaline earth metal ions, preferably calcium, magnesium, and barium ions; transition metal ions, preferably manganese, copper, zinc, and iron ions; and, if desired, ammonium ions that can be substituted with 1-4 C1-C4 alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and others. The ions are sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide.

[0014] The useful anions for acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanes, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting compound I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0015] Compound I can exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, hindered rotational isomers resulting from hindered rotation around a single bond of an asymmetric group, and geometric isomers. Those skilled in the art will understand that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to other stereoisomers or when separated from other stereoisomers. Additionally, those skilled in the art know how to separate, enrich, and / or selectively prepare said stereoisomers. The compounds of the present invention can exist as mixtures of stereoisomers, such as racemates, individual stereoisomers, or as optically active forms.

[0016] Compounds of Formula I can exist in different crystalline forms with potentially different biological activities. These also form part of the subject matter of this invention. Compounds of Formula I can also exist as trans-restricted isomers resulting from hindered rotation around a single bond of an asymmetric group. These also form part of the subject matter of this invention.

[0017] With respect to each variable, the embodiment of the intermediate obtained in the preparation of compound I corresponds to the embodiment of compound I. The term "compound I" refers to compound I.

[0018] In the definitions of the variables given above, the collective term "C" is used, typically representing the substituents. n -C m "" indicates the possible number of carbon atoms in the substituent or substituent structure portion in each case.

[0019] Structural portions having two or more connection possibilities shall be applied as follows:

[0020] The structural parts without parentheses in the name are bonded via the last structural part, such as heteroaryl-C1-C4 alkyl bonded via C1-C4 alkyl bond, etc.

[0021] The structural parts in parentheses in the name are bonded via the first structural part, such as C(=O)-(C1-C6 alkyl) bonded via C=O, etc.

[0022] The term "halogen" encompasses fluorine, chlorine, bromine, and iodine.

[0023] The term “C1-C6 alkyl” refers to straight-chain or branched saturated hydrocarbon groups having 1-6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.

[0024] The term "C1-C6 haloalkyl" refers to straight-chain or branched alkyl groups having 1-6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as described above, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, ... Chloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1-fluoromethyl-2-fluoroethyl, 1-chloromethyl-2-chloroethyl, 1-bromomethyl-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

[0025] The term “C1-C6 alkoxy” refers to a straight-chain or branched alkyl group having 1-6 carbon atoms (as defined above) bonded via oxygen at any position in the alkyl group, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0026] The term "C1-C6 haloalkoxy" refers to C1-C6 alkoxy groups as defined above, wherein some or all of the hydrogen atoms can be replaced by halogen atoms as described above, such as OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- ... ,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

[0027] The term “phenyl-C1-C4 alkyl or heteroaryl-C1-C4 alkyl” refers to an alkyl group having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a phenyl or heteroaryl group, respectively.

[0028] The term "C1-C4 alkoxy-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a C1-C4 alkoxy group (as defined above). Similarly, the term "C1-C4 alkylthio-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a C1-C4 alkylthio group.

[0029] As used herein, the term "C1-C6 alkylthio" refers to a straight-chain or branched alkyl group having 1-6 carbon atoms bonded via a sulfur atom (as defined above). Therefore, as used herein, the term "C1-C6 haloalkylthio" refers to a straight-chain or branched haloalkyl group having 1-6 carbon atoms bonded via a sulfur atom at any position on the haloalkyl group (as defined above).

[0030] The term "C1-C6 alkyl sulfinyl" refers to a straight-chain or branched alkyl group having 1-6 carbon atoms (as defined above), such as methyl sulfinyl and ethyl sulfinyl, bonded at any position of the alkyl group via the -S(=O)- structural moiety. Therefore, the term "C1-C6 haloalkyl sulfinyl" refers to a straight-chain or branched haloalkyl group having 1-6 carbon atoms (as defined above), bonded at any position of the haloalkyl group via the -S(=O)- structural moiety.

[0031] The term "C1-C6 alkylsulfonyl" refers to a straight-chain or branched alkyl group (as defined above) having 1-6 carbon atoms bonded at any position of the alkyl group via the -S(=O)2- structural moiety, such as a methanesulfonyl group. Therefore, the term "C1-C6 haloalkylsulfonyl" refers to a straight-chain or branched haloalkyl group (as defined above) having 1-6 carbon atoms bonded at any position of the haloalkyl group via the -S(=O)2- structural moiety.

[0032] The term "hydroxy-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms, wherein one hydrogen atom of the alkyl group is replaced by an OH group.

[0033] The term "amino-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms, wherein one hydrogen atom of the alkyl group is replaced by an NH2 group.

[0034] The term "di-C1-C6 alkylamino" refers to an amino group that is substituted by residues of two independently selected groups as defined by the term C1-C6 alkyl.

[0035] The term "C1-C4 alkylamino-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a nitrogen-bonded C1-C4 alkyl-NH- group. Similarly, the term "di-C1-C4 alkylamino-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a nitrogen-bonded (C1-C4 alkyl)2N- group.

[0036] The term "aminocarbonyl-C1-C4 alkyl" refers to an alkyl group having 1-4 carbon atoms, wherein one hydrogen atom of the alkyl group is replaced by a -(C=O)-NH2 group.

[0037] The term "C2-C6 alkenyl" refers to straight-chain or branched unsaturated hydrocarbon groups having 2-6 carbon atoms and double bonds in any position, such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl.

[0038] The term “C2-C6 ynyl” refers to a straight-chain or branched unsaturated hydrocarbon group having 2-6 carbon atoms and containing at least one triple bond, such as ethynyl, 1-propynyl, 2-propynyl (propynyl), 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl.

[0039] The term “C3-C8 cycloalkyl” refers to monocyclic saturated hydrocarbon groups having 3-8 carbon ring members, such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl.

[0040] The term “C3-C8 cycloalkoxy” refers to cycloalkyl groups having 3-8 carbon atoms (as defined above) bonded via oxygen.

[0041] The term “C(=O)-C1-C4 alkyl” refers to a group that is linked to a carbon atom by a -C(=O) group as indicated by the valence of the carbon atom.

[0042] The term "aliphatic" refers to compounds or groups consisting of carbon and hydrogen that are non-aromatic. Alicyclic compounds or groups are organic compounds that are both aliphatic and cyclic. They contain one or more fully carbon rings, which may be saturated or unsaturated, but do not possess aromatic characteristics.

[0043] The terms "cyclic structural moiety" or "cyclic group" refer to groups that are alicyclic or aromatic rings, such as phenyl or heteroaryl.

[0044] The term "and any aliphatic or cyclic group therein that is not substituted or is occupied by 1, 2, 3, 4 or at most the maximum possible number of identical or different groups R" 1a "Substitution" refers to aliphatic groups, cyclic groups, and groups containing both aliphatic and cyclic structural parts, such as phenyl-C1-C4 alkyl groups; therefore, groups containing both aliphatic and cyclic structural parts can be substituted or not substituted independently of each other.

[0045] The term "aryl" refers to an aromatic monocyclic or polycyclic system that may or may not contain 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, in addition to a carbon atom.

[0046] The term "heteroaryl" refers to an aromatic monocyclic or polycyclic system that contains 1, 2, 3, or 4 heteroatoms independently selected from N, O, and S, in addition to a carbon atom.

[0047] The term "phenyl" refers to an aromatic ring system containing six carbon atoms (commonly known as a benzene ring). In relation to group A, the term "phenyl" should be interpreted as... The diazole structural moiety and -C(=S)NR 1 R 2 -A benzene ring or a phenylene ring to which two groups are connected.

[0048] The term "3-10 member saturated, partially unsaturated, or aromatic monocyclic or bicyclic heterocycles, wherein the ring member atoms of the monocyclic or bicyclic heterocycle further include 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring member atoms in addition to carbon atoms" should be understood to refer to both aromatic monocyclic and bicyclic heteroaromatic ring systems, as well as saturated and partially unsaturated heterocycles, for example:

[0049] Three- or four-membered saturated heterocycles containing one or two heteroatoms selected from N, O and S as ring members, such as ethylene oxide, aziridine, thiapropane, oxacyclobutane, azirane, thiacyclobutane, [1,2]dioxacyclobutane, [1,2]dithiacyclobutane, and [1,2]diazacyclobutane.

[0050] And 5- or 6-membered saturated or partially unsaturated heterocycles containing 1, 2, or 3 heteroatoms selected from N, O, and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-iso azolealkyl, 4-iso azolealkyl, 5-iso Alzolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazoleyl, 4-pyrazoleyl, 5-pyrazoleyl, 2- azolealkyl, 4- azolealkyl, 5- Alzolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4- diazolidin-3-yl, 1,2,4- Diazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4- Diazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-iso Azoline-3-yl, 3-iso Azoline-3-yl, 4-iso Azoline-3-yl, 2-iso Azoline-4-yl, 3-iso Azoline-4-yl, 4-iso Azoline-4-yl, 2-iso Azoline-5-yl, 3-iso Azoline-5-yl, 4-iso Azoline-5-yl, 2-isothiazoline-3-yl, 3-isothiazoline-3-yl, 4-isothiazoline-3-yl, 2-isothiazoline-4-yl, 3-isothiazoline-4-yl, 4-isothiazoline-4-yl, 2-isothiazoline-5-yl, 3-isothiazoline-5-yl, 4-isothiazoline-5-yl, 2,3-dihydropyrazole-1-yl, 2,3-dihydropyrazole-2-yl, 2,3-dihydropyrazole -3-yl, 2,3-dihydropyrazole-4-yl, 2,3-dihydropyrazole-5-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 4,5-dihydropyrazole-1-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,3-dihydro 2-Azazole, 2,3-dihydro Azol-3-yl, 2,3-dihydro Azol-4-yl, 2,3-dihydro Azol-5-yl, 3,4-dihydro 2-Azazole, 3,4-dihydro Azol-3-yl, 3,4-dihydro Azol-4-yl, 3,4-dihydro Azol-5-yl, 3,4-dihydro 2-Azazole, 3,4-dihydro Azol-3-yl, 3,4-dihydro Azoxyl-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-di Alkyl-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiophenyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and the corresponding - subunits; and

[0051] 7-member saturated or partially unsaturated heterocycles such as tetrahydro- and hexahydro-aza radicals, such as 2,3,4,5-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]aza -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6-, or -7- methyl groups, hexahydroaza -1-, -2-, -3-, or -4-yl groups, tetrahydro- and hexahydroxyheptatrienyl groups such as 2,3,4,5-tetrahydro[1H]oxetane-2-, -3-, -4-, -5-, -6-, or -7-yl groups, 2,3,4,7-tetrahydro[1H]oxetane-2-, -3-, -4-, -5-, -6-, or -7-yl groups, 2,3,6,7-tetrahydro[1H]oxetane-2-, -3-, -4-, -5-, -6-, or -7-yl groups, hexahydroxyazo- -1-, -2-, -3- or -4-yl, tetrahydro- and hexahydro-1,3-diaza 1,4-diazine, tetrahydro- and hexahydro-1,4-diaza alkyl, tetrahydro- and hexahydro-1,3-oxazine oxazepinyl, tetrahydro- and hexahydro-1,4-oxazepinyl The groups include tetrahydro- and hexahydro-1,3-dioxepinyl, tetrahydro- and hexahydro-1,4-dioxepinyl and their corresponding - subunits; and

[0052] The terms "5 or 6-membered heteroaryl" or "5 or 6-membered aromatic heterocycle" refer to aromatic ring systems containing 1, 2, 3, or 4 heteroatoms independently selected from N, O, and S, in addition to a carbon atom. Examples of 5-membered heteroaryl groups include pyrrolo-1-yl, pyrrolo-2-yl, pyrrolo-3-yl, thiophenolo-2-yl, thiophenolo-3-yl, furanolo-2-yl, furanolo-3-yl, pyrazololo-1-yl, pyrazololo-3-yl, pyrazololo-4-yl, pyrazololo-5-yl, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, and imidazole-5-yl. 2-Azolium azole-4-yl, Azol-5-yl, isozonol Azol-3-yl, isozonol Azol-4-yl, isozonol 5-yl thiazolyl, 2-yl thiazolyl, 4-yl thiazolyl, 5-yl thiazolyl, 3-yl isothiazol-3, 4-yl isothiazol-4, 5-yl isothiazol-5, 1,2,4-triazol-1-yl, 3-yl 1,2,4-triazol-3, 5-yl 1,2,4-triazol-5, 1,2,4- diazol-3-yl, 1,2,4- Diazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; or

[0053] Six heteroaryl groups, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, and 1,2,4-triazin-3-yl.

[0054] With regard to each variable, the implementation of the intermediate corresponds to the implementation of compound I. Preferred are compounds I, and, where applicable, all the sub-formulas provided herein, such as compounds of formulas (I.1)-(I.8).

[0055] Regarding the variables, the implementation of the intermediate corresponds to the implementation of compound I. Preferably, R... 1 R 2 A, R A R a and R 1a Compounds I that, when their variables are independent of each other or more preferably combined (any possible combination of two or more substituents as defined herein), have the following meanings, as well as, where applicable, all the subformulas provided herein, such as compounds of formulas (I.1)-(I.8):

[0056] In one aspect of the invention, A is an unsubstituted or substituted group R consisting of 1, 2, 3, or 4 identical or different groups as defined or preferably defined herein. ASubstituted phenyl groups and wherein the group -C(=S)NR 1 R 2 Compared to trifluoromethyl The diazole group is attached to the phenyl ring at the para position.

[0057] In one embodiment, A is a thiophene group, wherein the aromatic heterocycle is unsubstituted or replaced by one or two identical or different groups R as defined herein or preferably defined. A Replacement; especially R A It can be chlorine, fluorine, or methyl.

[0058] In one embodiment, the present invention relates to a compound of formula I or its N-oxide or agronomical salt thereof, wherein the cyclic structural portion A is as defined by formulas (A.1)-(A.3):

[0059]

[0060] #1 should represent the bond to trifluoromethyl groups. The position of the diazole structural moiety and #2 indicate the -C(=S)NR of compound I. 1 R 2 The position of the group connection; and wherein the cyclic structure portion A is not substituted or is connected by one or two identical or different groups R. A Replacement and R in it A As defined or preferred herein. In another embodiment, the cyclic moiety A as defined in any of formulas (A.1)-(A.3) is not substituted or is occupied by one or two identical or different groups R. A Replace; and where R A It is chlorine, fluorine, or methyl. In a preferred embodiment, the cyclic structural portion A defined in any of formulas (A.1)-(A.3) is not substituted.

[0061] In a preferred embodiment of the present invention, R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C8 cycloalkyl; and any aliphatic and cyclic moiety thereof is unsubstituted or is occupied by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. a replace.

[0062] In another preferred embodiment of the invention, R AIt is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C8 cycloalkyl; and any aliphatic and cyclic portion thereof is either unsubstituted or substituted with 1, 2, 3, 4, or at most the maximum possible number of the same or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, and C3-C8 cycloalkyl; especially fluorine.

[0063] More preferably R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; especially a halogen or C1-C6 alkyl; more specifically, chlorine, fluorine, or methyl. In a more preferred embodiment, R A It can be chlorine, fluorine, or methyl.

[0064] R a According to the present invention, R is a halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, or C3-C8 cycloalkyl. In a preferred embodiment of the present invention, R a It is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl. More preferably, R a It is a halogen, especially fluorine.

[0065] In one aspect of the invention, R 1 and R 2 Independently thereof, it is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, -C(=O)-(C1-C6 alkyl) or -C(=O)-(C1-C6 alkoxy); and any of the above aliphatic or cyclic groups is not substituted or is replaced by 1, 2, 3 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0066] In one aspect of the invention, R 1 and R 2 Independently comprising hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl; and any of the above aliphatic or cyclic groups not substituted or substituted with one, two, three, or at most the maximum possible number of identical or different groups R as defined or preferably defined herein. 1a replace.

[0067] In another aspect of the invention, R 1It is hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl and R 2 It is a phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, phenyl, or heteroaryl; wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring contains 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring member atoms in addition to the carbon atom; and wherein any of the above-mentioned aliphatic or cyclic groups is not substituted or is occupied by 1, 2, 3, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0068] In another aspect of the invention, R 1 and R 2 Together with the nitrogen atoms to which they are bonded, they form 3-6 member saturated or partially unsaturated heterocycles, wherein the heterocycle contains 1, 2, or 3 heteroatoms independently selected from N, O, and S as ring member atoms in addition to one nitrogen atom and one or more carbon atoms; and wherein one or two CH2 groups of the heterocycle can be replaced by one or two groups independently selected from the group consisting of -C(=O)- and -C(=S)-; and wherein the heterocycle is not substituted or is replaced by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0069] In another aspect of the invention, R 1 and R 2 Together with the nitrogen atoms to which they are bonded, they form 3-6 member saturated or partially unsaturated heterocycles, wherein the heterocycle contains, in addition to a nitrogen atom and one or more carbon atoms, an additional heteroatom selected from N, O, and S as a ring member atom; and wherein the heterocycle is not substituted or is occupied by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0070] In one implementation, R 1 It is hydrogen or methyl and R 2 It is a C3-C6 cycloalkyl group, wherein the cycloalkyl group is not substituted or is surrounded by 1, 2, 3, 4 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0071] In one implementation, R 1 It is hydrogen or methyl and R 2 It is a C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group, wherein the aliphatic group is unsubstituted or is replaced by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0072] In another implementation, R 1 It is hydrogen or methyl and R 2 The radical is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or cyclopropyl; and any aliphatic or cyclic group therein is not substituted or is replaced by 1, 2, 3, 4, or 5 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0073] In another implementation plan, R 1 It is hydrogen or methyl and R 2 It is phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, C3-C6 cycloalkyl-C1-C4 alkyl; and any aliphatic or cyclic group therein is not substituted or is replaced by 1, 2, 3, 4 or 5 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0074] In one implementation, R 1 It is hydrogen or methyl and R 2 It is a heteroaryl-C1-C4 alkyl group, wherein any aliphatic or cyclic group is not substituted or is occupied by 1, 2, 3 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0075] In one implementation, R 1 It is hydrogen or methyl and R 2 The phenyl group is a phenyl group that is not substituted or is surrounded by 1, 2, 3, 4 or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0076] In a preferred embodiment of the present invention, R 1a It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C3-C8 cycloalkyl. In another preferred aspect of the invention, R 1a It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy. In a more preferred aspect of the invention, R 1a It is a halogen or cyano group; especially halogens, and most particularly fluorine.

[0077] In another embodiment, the present invention relates to compounds of formula I (I.1) or their N-oxides or agronomical salts, wherein...

[0078] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0079] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkoxy; and wherein the aliphatic and cyclic structural portions are not substituted or are occupied by 1, 2, 3, or 4 identical or different groups R. a Replace; among them

[0080] R a It can be halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl;

[0081] R 1 It can be hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C(=O)-(C1-C6 alkyl) or C(=O)-(C1-C6 alkoxy);

[0082] R 2 It is a phenyl, a 5- or 6-membered aromatic heterocycle, a phenyl-C1-C4 alkyl, or a heteroaryl-C1-C4 alkyl; wherein the ring member atoms of the aromatic heterocycle include 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring member atoms in addition to carbon atoms; and wherein any cyclic group is not substituted or is substituted by 1, 2, 3, or 4 identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 haloalkoxy.

[0083] In another embodiment, the invention relates to compound (I.1), wherein A is (A.1). In another embodiment, the invention relates to compound (I.1), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.1) wherein A is (A.1) and wherein A is not substituted.

[0084] In another embodiment, the invention relates to compound (I.1), wherein A is (A.2). In another embodiment, the invention relates to compound (I.1), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.1) wherein A is (A.2) and wherein A is not substituted.

[0085] In another embodiment, the present invention relates to a compound of formula I (I.2) or its N-oxide or agronomical salt, wherein...

[0086] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0087] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkoxy; and wherein the aliphatic and cyclic structural portions are not substituted or are occupied by 1, 2, 3, or 4 identical or different groups R. a Replace; among them

[0088] R a It can be halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl;

[0089] R 1 It can be hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C(=O)-(C1-C6 alkyl) or C(=O)-(C1-C6 alkoxy);

[0090] R 2 It is a phenyl group that is not substituted or is substituted with 1, 2, 3 or 4 identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[0091] In another embodiment, the invention relates to compound (I.2), wherein A is (A.1). In another embodiment, the invention relates to compound (I.2), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.2) wherein A is (A.1) and wherein A is not substituted.

[0092] In another embodiment, the present invention relates to a compound (I.2) wherein A is (A.2). In another embodiment, the present invention relates to a compound (I.2) wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.2) wherein A is (A.2) and wherein A is not substituted.

[0093] In yet another embodiment, the present invention relates to a compound of formula I (I.3) or its N-oxide or agronomical salt, wherein...

[0094] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0095] R A It is a halogen, a C1-C6 alkyl, a C1-C6 haloalkyl, a C1-C6 alkoxy, or a C1-C6 haloalkoxy;

[0096] R 1 It can be hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C(=O)-(C1-C6 alkyl) or C(=O)-(C1-C6 alkoxy);

[0097] R 2 It is a phenyl group that is not substituted or is substituted with 1, 2, 3 or 4 identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[0098] In another embodiment, the invention relates to compound (I.3), wherein A is (A.1). In another embodiment, the invention relates to compound (I.3), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.3) wherein A is (A.1) and wherein A is not substituted.

[0099] In another embodiment, the invention relates to compound (I.3), wherein A is (A.2). In another embodiment, the invention relates to compound (I.3), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.3) wherein A is (A.2) and wherein A is not substituted.

[0100] In yet another embodiment, the present invention relates to a compound of formula I (I.4) or its N-oxide or agronomical salt, wherein...

[0101] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0102] R AIt is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0103] R 1 It can be hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

[0104] R 2 It is a phenyl group that is not substituted or is substituted with 1, 2, 3 or 4 identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[0105] In another embodiment, the invention relates to compound (I.4), wherein A is (A.1). In another embodiment, the invention relates to compound (I.4), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.4) wherein A is (A.1) and wherein A is not substituted.

[0106] In another embodiment, the invention relates to compound (I.4), wherein A is (A.2). In another embodiment, the invention relates to compound (I.4), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.4) wherein A is (A.2) and wherein A is not substituted.

[0107] In yet another embodiment, the present invention relates to compounds of formula I (I.5) or their N-oxides or agriculturally usable salts, wherein...

[0108] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0109] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkoxy; and wherein the aliphatic and cyclic structural portions are not substituted or are occupied by 1, 2, 3, or 4 identical or different groups R. a Replace; among them

[0110] R a It can be halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl;

[0111] R1 and R 2 Independently, they are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl; especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or cyclopropyl; and wherein the aliphatic and cyclic groups are not substituted or are replaced by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0112] In another embodiment, the invention relates to compound (I.5), wherein A is (A.1). In another embodiment, the invention relates to compound (I.5), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.5) wherein A is (A.1) and wherein A is not substituted.

[0113] In another embodiment, the invention relates to compound (I.5), wherein A is (A.2). In another embodiment, the invention relates to compound (I.5), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.5) wherein A is (A.2) and wherein A is not substituted.

[0114] In another embodiment, the present invention relates to a compound of formula I (I.6) or its N-oxide or agronomical salt, wherein...

[0115] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0116] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0117] R 1 and R 2 Independently, they are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl; especially hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or cyclopropyl.

[0118] In another embodiment, the invention relates to compound (I.6), wherein A is (A.1). In another embodiment, the invention relates to compound (I.6), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.6) wherein A is (A.1) and wherein A is not substituted.

[0119] In another embodiment, the invention relates to compound (I.6), wherein A is (A.2). In another embodiment, the invention relates to compound (I.6), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.6) wherein A is (A.2) and wherein A is not substituted.

[0120] In another embodiment, the present invention relates to a compound of formula I (I.7) or its N-oxide or agronomical salt, wherein...

[0121] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0122] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkoxy; and wherein the aliphatic and cyclic structural portions are not substituted or are occupied by 1, 2, 3, or 4 identical or different groups R. a Replace; among them

[0123] R a It can be halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl;

[0124] R 1 and R 2 Together with the nitrogen atoms to which they are bonded, they form 3-6 member saturated or partially unsaturated heterocycles, wherein the heterocycle contains no other heteroatoms besides a nitrogen atom and a carbon atom, or contains 1, 2, or 3 heteroatoms independently selected from N, O, and S as ring member atoms; and wherein one or two CH2 groups of the carbon ring or heterocycle can be replaced by one or two groups independently selected from -C(=O)- and -C(=S)-; and wherein the heterocycle is not substituted or is replaced by 1, 2, 3, 4, or at most the maximum possible number of the same or different groups R as defined or preferably defined herein. 1a replace.

[0125] In another embodiment, the invention relates to compound (I.7), wherein A is (A.1). In another embodiment, the invention relates to compound (I.7), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.7) wherein A is (A.1) and wherein A is not substituted.

[0126] In another embodiment, the invention relates to compound (I.7), wherein A is (A.2). In another embodiment, the invention relates to compound (I.7), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.7) wherein A is (A.2) and wherein A is not substituted.

[0127] In another embodiment, the invention relates to compounds of formula I (I.8) or their N-oxides or agronomical salts, wherein...

[0128] A is selected from formulas (A.1)-(A.3), and is either unsubstituted or surrounded by one or two identical or different groups R. A Replace; among them

[0129] R A It is a halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0130] R 1 and R 2 Together with the nitrogen atoms to which they are bonded, they form 3-6 saturated or partially unsaturated heterocycles, wherein the heterocycle contains no other heteroatoms besides a nitrogen atom and a carbon atom, or contains 1, 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein the heterocycle is not substituted or is substituted by 1, 2, 3 or 4 identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[0131] In another embodiment, the invention relates to compound (I.8), wherein A is (A.1). In another embodiment, the invention relates to compound (I.8), wherein A is (A.1) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.8) wherein A is (A.1) and wherein A is not substituted.

[0132] In another embodiment, the invention relates to compound (I.8), wherein A is (A.2). In another embodiment, the invention relates to compound (I.8), wherein A is (A.2) and wherein A is a group R as defined or preferably defined herein. A Substitution. In yet another embodiment, the present invention relates to a compound (I.8) wherein A is (A.2) and wherein A is not substituted.

[0133] According to one embodiment, the present invention relates to the use of compound of formula IA or compound of formula IA in the control of plant pathogenic fungi:

[0134]

[0135] Where R 1 and R 2 As defined or preferred in this paper, Equation I is as follows.

[0136] According to one embodiment, the present invention relates to the use of compounds of formula IB or compounds of formula IB in the control of pathogenic fungi of plants:

[0137]

[0138] Where R 1 and R 2 As defined or preferred in this paper, Equation I is as follows.

[0139] The preferred compounds of the present invention, I and their uses, are compiled in Tables 1 and 2 below. Furthermore, the groups R mentioned in Table A and also mentioned in Tables 1 and 2... 1 and R 2 The combination of these substituents is itself a particularly preferred aspect of the substituents, regardless of any combinations mentioned herein.

[0140] Table 1

[0141] Where R 1 and R 2 For each individual compound, in each case it corresponds to a compound of formula IA (IAA-1 to IAA-473) in one of rows A-1 to A-473 of Table A.

[0142] Table 2

[0143] Where R 1 and R 2 For each individual compound, in each case it corresponds to one of the formula IB compounds (IBA-1 to IBA-473) in rows A-1 to A-473 of Table A.

[0144] Table A:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] Compounds of Formula I can be prepared according to methods described in the prior art or similar methods. Synthesis utilizes readily available starting materials that are known, commercially available, or can be prepared from known compounds using conventional procedures.

[0152] Compounds of Formula I can be prepared by reacting a type II amide with a suitable sulfonating agent, preferably Lawessons' agent, in an organic solvent, preferably at a temperature of 20-150°C, preferably at 110°C, as described above (see, for example, Journal of Organic Chemistry, 2008, 73, 9102 or European Journal of Organic Chemistry, 2015, 30, 6687).

[0153]

[0154] Compounds of Formula II can be prepared in a manner similar to that described in WO 2015 / 185485A1, for example by reacting a type II acyl chloride with the corresponding amine or its hydrochloride in an organic solvent, preferably in a nonpolar hydrocarbon, at a temperature of -20°C to 40°C, preferably at 0°C or at room temperature as previously described (see, for example, Journal of the American Chemical Society, 2012, 134(20), 8298 or Journal of the American Chemical Society, 2005, 127(38), 13150). If a hydrochloride is used, it may be suitable to add an organic base, preferably an amine, to release the free amine in situ.

[0155]

[0156] Compound III can be obtained by reacting a carboxylic acid of formula IV with a suitable chlorinating agent, preferably thionyl chloride, directly or in an organic solvent, preferably a nonpolar hydrocarbon or a halocarbon. This reaction is preferably carried out at elevated temperatures, preferably 40-100°C.

[0157]

[0158] Compound IV can be prepared by reacting an amidine of formula V with trifluoroacetic anhydride in an organic solvent, such as dichloromethane or THF, at a temperature of 0-100°C, preferably at about 25°C, as described above in WO2013 / 008162.

[0159]

[0160] Those skilled in the art will recognize that type IV compounds can be obtained by treating type V nitriles with hydroxylamine (or its HCl salt) in an organic solvent in the presence of a base (see precedents such as WO 2009 / 074950, WO2006 / 013104, EP1932843).

[0161]

[0162] The compounds of Formula I of the present invention, or compositions comprising said compounds, are suitable as fungicides. They are characterized by significant efficacy against a wide range of plant pathogenic fungi, including, in particular, soil-borne fungi derived from or closely related to any of the following: Ascomycota (Ascomycetes), such as, but not limited to, *Cocholiobolus*, *Colletotrichum*, *Fusarium*, *Microdochium*, *Penicillium*, *Phoma*, *Magnaporte*, *Zymoseptoria*, and *Pseudocercosporella*; Basidiomycota Basidiomycetes, including but not limited to genera such as *Phakospora*, *Puccinia*, *Rhizoctonia*, *Sphacelotheca*, *Tilletia*, *Typhula*, and *Ustilago*; Chytridiomycota (Chytridiomycetes), including but not limited to genera such as *Chytridiales* and *Synchytrium*; Deuteromycetes (synonyms: Fungi) imperfecti), such as but not limited to the genera Ascochyta, Diplodia, Erysiphe, Fusarium, Phoopsis, and Pyrenophora; Peronosporomycetes (synonyms for Oomycetes), such as but not limited to the genera Peronospora, Pythium, and Phytophthora; Plasmodiophoromycetes, such as but not limited to the genus Plasmodiophora; Zygomycetes, such as but not limited to the genus Rhizopus.

[0163] Some Formula I compounds and the compositions of this invention are systemic and can be used as foliar fungicides, seed dressing fungicides, and soil fungicides for crop protection. Furthermore, they are suitable for controlling harmful fungi, especially those occurring in wood or plant roots.

[0164] Compound I and the composition of this invention are applicable to various cultivated plants such as cereals, such as wheat, rye, barley, triticale, oats, or rice; beets, such as sugar beets or fodder beets; fruits, such as pome fruits, drupes, or berries, such as apples, pears, plums, peaches, apricots, cherries, strawberries, raspberries, blackberries, or gooseberries; legumes, such as lentils, peas, alfalfa, or soybeans; oilseed plants, such as rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbitaceous plants, such as pumpkins, cucumbers, or melons; fiber plants, such as cotton, flax, hemp, or jute; and citrus fruits, such as oranges, lemons, and grapefruits. Or oranges; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds, or bell peppers; laurel plants such as avocados, cinnamon, or camphor; energy and raw material plants such as corn, soybeans, rapeseed, sugarcane, or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and wine grapes); hops; lawns; stevia (also known as stevia); natural rubber plants or ornamental and forest plants such as flowers, shrubs, broad-leaved trees, or evergreen trees such as conifers, and the prevention of a wide range of plant pathogenic fungi in plant propagation materials such as seeds and crop materials of these plants is particularly important.

[0165] Compound I and its compositions are preferably used to control a large number of fungi on field crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugarcane; fruits; grapevines; ornamental plants; or vegetables such as cucumbers, tomatoes, green beans or pumpkins.

[0166] The term "plant propagation material" should be understood to refer to all propagating parts of a plant, such as seeds, as well as asexual plant material that can be used to propagate plants, such as cuttings and tubers (e.g., potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, branches, buds, and other plant parts, including seedlings and seedlings transplanted from soil after germination or emergence. These seedlings may also be protected prior to transplanting by full or partial treatment via soaking or watering.

[0167] Preferably, the treatment of plant propagation material with compound I and its composition is used to control a large number of fungi on cereals such as wheat, rye, barley and oats; rice, corn, cotton and soybean.

[0168] The term "cultivated plant" should be understood to include plants that have been modified through mutagenesis or genetic engineering to provide new characteristics or to modify existing characteristics.

[0169] Compound I and its combinations are particularly suitable for controlling the following plant diseases: *Albugo* (white rust) on ornamental plants, vegetables (e.g., *A. candida*) and sunflowers (e.g., *A. tragopogonis*); *Alternaria* (alternaria leaf spot) on vegetables, rapeseed (*A. brassicola* or *A. brassicae*), sugar beets (*A. tenuis*), fruits, rice, soybeans, potatoes (e.g., *A. solani* or *A. alternata*), tomatoes (e.g., *A. solani* or *A. alternata*), and wheat; *Aphanomyces* on sugar beets and vegetables; and *Ascochyta* on cereals and vegetables, such as *A. tri* on wheat. Anthracnose and *A. hordei* on barley; *Bipolaris* and *Drechslera* (sexual form: *Cochliobolus*), such as leaf spot on maize (*D. maydis* or *B. zeicola*), leaf blight on cereals (*B. sorokinina*) and *B. oryzae* on rice and turf; wheat powdery mildew (*Blumeria graminis*) on cereals (e.g., wheat or barley); fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, root celery, and cabbage), rapeseed, flowers, grapevines, forest plants, and *Botrytis* on wheat. cinerea (sexual form: Botryotinia fuckeliana: gray mold); Bremialactucae on lettuce (downy mildew); Ceratocystis (synonym Ophiostoma) on broadleaf and evergreen trees (rot or wilt), e.g. C. ulmi on elm (Dutch elm); maize (e.g. gray leaf spot: C. zeae-maydis), rice, sugar beets (e.g. beticola), sugarcane, vegetables, coffee, soybeans (e.g. soybean gray spot (C. sojina) or soybean purple spot (C. kikuchii)) and Cercospora on rice (Cercospora leaf spot); tomatoes (e.g. tomato leaf mold (C. fulvum): leaf mold) and cereals (e.g. wheat c. spp.).Cladosporium on *Helicobacter herbarum* (ear rot); *Claviceps purpurea* on cereals (ergot disease); *C. carbonum* on maize, *C. sativus* (asexual form: *Helicobacter oryzae*) and *C. miyabeanus* (asexual form: *Helicobacter oryzae*) on rice (asexual form: *Helicobacter oryzae*) (leaf spot disease); *C. gossypii* on cotton, *C. graminicola* on maize (*C. graminicola*: anthracnose stem rot), berries, potatoes (… Examples of anthracnose diseases include: *C. coccodes* (watermelon anthracnose): black spot disease; *C. lindemuthianum* (bean anthracnose) and *C. truncatum* (soybean anthracnose) or *C. gloeosporioides* (soybean anthracnose): *Colletotrichum* (sexual form: *Glomerella*) (anthracnose); *Corticium*, such as *C. sasakii* (rice anthracnose): sheath blight; *Corynespora cassiicola* (cucumber brown spot disease) (soybean and ornamental plants); *Cycloconium*, such as *C. oleaginum* (olive rust disease); and *C. liriodendri* (sex form: *Neonectria*) (fruit trees, grapevines). Liriodendri (blackfoot disease) and Cylindrocarpon on ornamental trees (e.g., fruit tree rot or grapevine blackfoot disease, sexual types: Nectria or Neonectria); Dematophora (sexual type: Rosellia) necatrix on soybeans (root rot / stem rot); Diaporthe, for example, on soybeans... D. phaseolorum (root blight) is the pathogen of soybean stem canker; it is also found in maize, cereals such as barley (e.g., D. teres, barley leaf spot), wheat (e.g., D. tritici-repentis, brown spot), rice, and lawns. Other pathogens include *Pyrenophora* (sexual form); and *Formitiporia* (synonym *Phellinus*) punctata, *F.*Esca (vine blight, wilt) on grapevines caused by *Mediterranea*, *Phaeomoniella chlamydospora* (formerly *Phaeoacremonium chlamydosporum*), *Phaeoacremonium aleophilum*, and / or *Botryosphaeria obtusa*; *Elsinoe* species on pome (*E. pyri*), berries (*E. veneta*: anthracnose) and grapevines (*E. ampelina*: anthracnose); and *Entyloma* on rice. Oryzae (leaf smut); Epicoccum (smut) on wheat; Erysiphe (powdery mildew) on sugar beets (E. betaae), vegetables (e.g., E. pisi) such as cucurbitaceous plants (e.g., E. cichoracearum), cabbage, rapeseed (e.g., E. cruciferarum); Eutypa lata (ulcer or wilt disease) on fruit trees, grapevines, and ornamental trees (asexual form: Cytosporina lata, synonym Libertella). blepharis); Exserohilum (synonym: long-horn spores) on maize (e.g., E. turcicum); Fusarium (sexual form: Gibberella) on various plants (wilt, root rot, or stem rot), such as Fusarium graminearum or Fusarium culmorum on cereals (e.g., wheat or barley) (root rot, black spot, or silver tip), and Fusarium acicularis on tomatoes. (F. oxysporum), F. solani (f. sp. glycines, now synonymous with F. virguliforme, the North American soybean sudden death syndrome pathogen, and F. tucumaniae and F. brasiliense, which each cause sudden death syndrome, and F. verticillioides on maize; Gaeumannomyces graminis (take-all disease) on cereals (e.g., wheat or barley) and maize; and G. zeae (grains) and G. zeae (rice) on cereals and rice (e.g., G. zeae).Fujikuroi: *Fujitella* on seedling blight; *Glomerella cingulata* on apple vines, pome and other plants, and *G. gossypii* on cotton; *Grainstaining Complex* on rice; *Guignardia bidwellii* (black rot) on grapevines; *Gymnosporangium* on Rosaceae and juniper, such as *G. sabinae* (rust) on pears; *Hemileia* (synonym: *Hemileia*, sexual form: *Hemileia*) on corn, cereals and rice; *H. vastatrix* (coffee leaf rust) on coffee; *Isariopsis clavispora* (synonym: *Cladosporium*) on grapevines. vitis); Macropomina phaseolina (synonym phaseoli) on soybeans and cotton (root rot / stem rot); Microdochium nivale (snow mold) on cereals (e.g., wheat or barley); Microsphaeradiffusa (powdery mildew) on soybeans; Monilinia, such as M. laxa, M. fructicola, and M. fructigena (flower and branch rot, brown rot) on drupes and other Rosaceae plants; Mycosphaerella on cereals, bananas, berries, and peanuts, such as M. graminicola on wheat (asexual form: Septoria) *Tritici*, *Sigatoka* black spot, or *M. fijiensis* on bananas; *Peronospora* on cabbage (e.g., *P. brassicae*), rapeseed (e.g., *P. parasitica*), onions (e.g., *P. destructor*), tobacco (*P. tabacina*), and soybeans (e.g., *P. manshurica*) (downy mildew); *Phakopsora pachyrhizi* and *P. Meibomiae* on soybeans (soybean rust); *P. Tracheiphila* and *P. tetraspora* on grapevines and soybeans (e.g., *P. soybean stem brown rot*).Phialophora on gregata (stem diseases); Phomalingam (root rot and stem rot) on rapeseed and cabbage, and P. betae (root rot, leaf spot, and damping-off) on sugar beets; Phopsis on sunflower, grapevines (e.g., P. viticola: vine rot and leaf spot) and soybeans (e.g., stem rot: P. phaseoli, sexual form: Diaporthe phaseolorum); Physoderma on corn. Maydis (brown spot disease); Phytophthora (wilt, root rot, leaf rot, stem rot, and fruit tree rot) on various plants such as bell peppers and cucurbitaceae (e.g., *Phytophthora capsici*), soybeans (e.g., *Phytophthora megasperma*, synonym *P. sojae*), potatoes and tomatoes (e.g., *Phytophthora infestans*: late blight) and broad-leaved trees (e.g., *Phytophthora ramorum*: oak sudden death); Plasmodiophora abrassicae (clump rot) on cabbage, rapeseed, radishes, and other plants; and downy mildew (*Plasmo...*). Para), such as *P. viticola* (downy mildew on grapevines) and *P. halstedii* on sunflowers; *Podosphaera* (powdery mildew) on Rosaceae plants, hops, pome fruits, and berries, such as *P. leucotricha* (powdery mildew fungus on apples); *Polymyxa* on cereals such as barley and wheat (*P. graminis*) and sugar beets (*P. betaae*), and the viral diseases transmitted by these fungi; *Pseudocercosporella* (wheat basal rot fungus on cereals such as wheat or barley). *Pseudoperonospora* (eye spot disease, sexual form: *Tapesia yallundae*); various plants with *Pseudoperonospora* (downy mildew), such as *P. cucumbersis* on cucurbitaceous plants or *P. humili* on hops; *Pseudopezicula tracheiphila* (grape angular leaf scorch fungus or 'rotbrenner', asexual form: *Phialophora*) on grapevines; various plants with *Puccinia* (rust disease), such as *P. wheat rust* on cereals such as wheat, barley, or rye.Triticina (brown rust or leaf rust), P. striiformis (striped rust or yellow rust), P. hordei (barley yellow dwarf leaf rust), P. graminis (stem rot or black rust) or P. recondita (wheat leaf rust) (brown rust or leaf rust), P. kuehnii (orange rust) on sugarcane and P. asparagi (asparagi) on asparagus; small Wheat leaf blight pathogen (Pyrenophora (asexual form: Drechslera) tritici-repentis) (yellow spot disease) on wheat or barley net spot pathogen (P. teres) (net spot disease) on barley; *Pyricularia*, such as *P. oryzae* (sexual form: Magnaporthegrisea, rice blast) on rice and *P. grisea* on turf and cereals; *Pythium* (damping-off) on turf, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables, and various other plants (e.g., *P. ultimum* or *P. aphanidermatum*); *Ramularia*, such as *R. collo-cygni* (physiological leaf spot) on barley and *R. beet* (beet leaf spot pathogen) on sugar beet. icola); Rhizoctonia species on cotton, rice, potatoes, lawns, corn, rapeseed, sugar beets, vegetables, and various other plants, such as Rhizoctonia solani on soybeans (root rot / stem rot), Rhizoctonia solani on rice (sheath blight), or Rhizoctonia cerealis on wheat or barley (wheat sheath blight); Rhizopus on strawberries, carrots, cabbage, grapevines, and tomatoes. * *Stolonifer* (black mold, soft rot); *Rhynchosporium secalis* on barley, rye, and triticale (leaf spot); *Sarocladium oryzae* and *S. attenuatum* on rice (leaf sheath rot); *Sclerotinia* on vegetables and field crops such as rapeseed, sunflower (e.g., *Sclerotiorum*) and soybean (e.g., *S. rolfsii* or *S. sclerotiorum*) (stem rot or white mold); *Septoria* on various plants, such as *S. glycines* on soybean (brown spot), and *S. wheat* on wheat.Tritici (leaf spot disease) and S. noodorum (leaf spot disease) on cereals; Uncinula necator (powdery mildew, asexual form: Oidium tuckeri) on grapevines; Helminthosporium turcicum (leaf blight) on maize and Setospaeria (leaf blight) on lawns; Sphacelotheca (smut) on maize, sorghum, and sugarcane; Sphaerotheca (smut) on cucurbitaceous plants. Powdery mildew (S. fuliginea); powdery mildew fungus (Spongospora subterranea) on potatoes and viral diseases transmitted by it; Stagonospora on cereals, such as S. nodorum on wheat (spot blight, sexual form: Leptosphaeria nodorum); Synchytrium on potatoes. endobioticum (potato cancer); *Taphrina*, such as *T. deformans* (leaf curl) on peaches and *T. pruni* (plum bud) on plums; *Thielaviopsis* (black root rot) on tobacco, pome fruits, vegetables, soybeans, and cotton, such as *T. basicola* (synonym *Chalaraelegans*); *Tilletia* (smut or glossy smut) on cereals, such as *T. tritici* (synonym *T. caries*, wheat smut) and *T. controversa* (dwarf smut) on wheat; *Typhula* on barley or wheat. Incarnata (gray snow rot); smut fungi, such as *Urocystis* on rye (*U. occulta*) (streaked smut); rust fungi on vegetables such as beans (e.g., *U. appendiculatus*, synonym *U. phaseoli*) and sugar beets (e.g., *U. betaae*) (rust); cereals (e.g., *U. nuda* and *U. avaenae*), and maize (e.g., *U. maize*).Maydis: *Ustilago* (smut) on corn and sugarcane; *V. inaequalis* (apple scab) and *Venturia* (spot scab) on apples and pears; and *Verticillium* (wilt) on various fruit and ornamental trees, grapevines, berries, vegetables, and field crops, such as *V. dahliae* on strawberries, rapeseed, potatoes, and tomatoes.

[0170] In a preferred embodiment, compound I and its compositions are particularly suitable for controlling the following plant diseases: various rust fungi (rusts) on plants, such as, but not limited to, wheat rust (P. triticina) (brown rust or leaf rust), stripe rust (P. striiformis) (stripe rust or yellow rust), barley rust (P. hordei) (barley yellow dwarf leaf rust), graminis (stem rot or black rust) or wheat leaf rust (P. recondita) (brown rust or leaf rust) on cereals such as wheat, barley or rye, and various Phakoporaceaespp. on plants, especially Phakoporora pachyrhizi and Phakoporomeae (soybean rust) on soybeans.

[0171] Compound I and its compositions are also suitable for the protection of stored or harvested products and for the prevention of harmful fungi in the protection of materials.

[0172] The term “material protection” should be understood to mean the protection of industrial and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, coolant lubricants, fibers or fabrics, from harmful microorganisms such as fungi and bacteria. For the protection of wood and other materials, special attention should be paid to the following harmful fungi: Ascomycetes, such as *Aureobasidium pullulans*, *Sclerophoma* spp., *Chaetomium* spp., *Humicola* spp., *Petriella* spp., and *Trichurus* spp.; Basidiomycetes, such as *Coniophora* spp., *Coriolus* spp., *Gloeophyllum* spp., *Lentinus* spp., *Pleurotus* spp., *Poria* spp., *Serpula* spp., and *Tyromyces*. Fungi belonging to the class Deuteromycetes, such as *Aspergillus* spp., *Cladosporium*, *Penicillium* spp., *Trichoderma* spp., *Alternaria*, *Paecilomyces* pp., and Zygomycetes, such as *Mucor* spp., should also be noted in the protection of stored and harvested products. Additionally, the following yeasts should be monitored: *Candida* spp. and *Saccharomyces cerevisae*.

[0173] The processing method of this invention can also be used in the field of protecting stored or harvested products from fungal and microbial invasion. According to the invention, the term "stored product" should be understood to refer to natural substances of plant or animal origin and their processed forms, which are derived from their natural life cycle and are desired to be preserved for a long period. Stored products of crop origin, such as plants or parts thereof, such as stems, leaves, tubers, seeds, fruits, or grains, can be protected in a freshly harvested state or in a processed form, such as pre-drying, moistening, crushing, grinding, pressing, or roasting, methods also known as post-harvest processing. Also falling under the definition of stored products is wood, whether in unprocessed form, such as building timber, power line towers and fences, or in finished form, such as wooden furniture or articles. Stored products of animal origin are raw hides, leather, fur, hair, etc. The combination of the present invention can prevent adverse effects such as spoilage, discoloration, or mold. Preferably, "stored product" should be understood to refer to natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pome fruits, drupes, berries, and citrus fruits and their processed forms.

[0174] Compounds of Formula I can exist in different crystalline forms with varying biological activities. They are also the subject of this invention.

[0175] Compound I is used directly or in combination by treating fungi or plants, plant propagation materials such as seeds, soil, surfaces, materials, or spaces where fungal infection needs to be prevented, with an effective amount of the active substance. Application can be carried out before or after fungal infection of the plant, plant propagation material such as seeds, soil, surfaces, materials, or spaces.

[0176] Plant propagation material may be preventively treated with compound I itself or a composition containing at least one compound I during or before planting or transplanting.

[0177] The present invention also relates to an agricultural chemical composition comprising an adjuvant and at least one compound I of the present invention.

[0178] Agricultural chemical compositions contain a fungicide-effective amount of compound I. The term "effective amount" means an amount of composition or compound I sufficient to control harmful fungi on cultivated plants or in the protection of materials without causing significant damage to the treated plants. This amount can vary over a wide range and depends on various factors such as the species of fungus to be controlled, the cultivated plant or material being treated, climatic conditions, and the specific compound I used.

[0179] Compound I, its N-oxide, and salt can be converted into types commonly used in agrochemical compositions, such as solutions, emulsions, suspensions, powders, pastes, granules, molded products, capsules, and mixtures thereof. Examples of composition types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or granules (e.g., WP, SP, WS, DP, DS), molded products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and other composition types are defined in "Catalogue of pesticide formulation types and international coding system," Technical Monograph, Vol. 2, 6th edition, May 2008, CropLife International.

[0180] The compositions are prepared in a known manner as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, AgrowReports DS243, T&F Informa, London, 2005.

[0181] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solvents, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and binders.

[0182] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, and cyclohexanol; diols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.

[0183] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as cereal flour, bark flour, wood flour, and nut shell flour, as well as mixtures thereof.

[0184] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solvents, wetting agents, penetration enhancers, protective colloids, or auxiliaries. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0185] Suitable anionic surfactants are alkali metal, alkaline earth metal, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, as well as mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamides. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0186] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated by 1-50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitol, ethoxylated sorbitol, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0187] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing blocks of alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[0188] Suitable adjuvants are compounds that possess negligible pesticide activity or even no pesticide activity themselves, but which improve the biological properties of compound I against the target analyte. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Other examples are listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0189] Suitable thickeners are polysaccharides (such as xanthan gum and carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0190] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0191] Suitable antifreeze agents include ethylene glycol, propylene glycol, urea, and glycerin.

[0192] Suitable defoamers are polysiloxanes, long-chain alcohols, and fatty acid salts.

[0193] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[0194] Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.

[0195] Examples of composition types and their preparation are as follows:

[0196] i) Water-soluble concentrates (SL, LS)

[0197] Dissolve 10-60 wt% of Compound I and 5-15 wt% of wetting agent (e.g., alcohol alkoxylate) in water and / or a water-soluble solvent (e.g., alcohol) added to 100 wt%. The active substance dissolves upon dilution with water.

[0198] ii) Dispersible concentrate (DC)

[0199] Dissolve 5-25 wt% of Compound I and 1-10 wt% of a dispersant (e.g., polyvinylpyrrolidone) in an organic solvent (e.g., cyclohexanone) added up to 100 wt%. Dilute with water to obtain a dispersion.

[0200] iii) Emulsifiable concentrate (EC)

[0201] Dissolve 15-70 wt% of Compound I and 5-10 wt% of emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) in a water-insoluble organic solvent (e.g., an aromatic hydrocarbon) added to 100 wt%. Dilute with water to obtain an emulsion.

[0202] iv) Emulsions (EW, EO, ES)

[0203] 5-40 wt% of Compound I and 1-10 wt% of emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). The mixture is then introduced into 100 wt% water using an emulsifier to form a homogeneous emulsion. The emulsion is diluted with water to obtain a final emulsion.

[0204] v) Suspension (SC, OD, FS)

[0205] In a stirred ball mill, 20-60 wt% of Compound I is subjected to underwater milling with the addition of 2-10 wt% dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e.g., xanthan gum), and up to 100 wt% water to obtain a finely ground active substance suspension. The suspension is then diluted with water to obtain a stable active substance suspension. For FS type compositions, up to 40 wt% binder (e.g., polyvinyl alcohol) is added.

[0206] vi) Water-dispersible particles and water-soluble particles (WG, SG)

[0207] Compound I (50-80 wt%) is finely ground with up to 100 wt% dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble particles using industrial equipment (e.g., extruder, spray tower, fluidized bed). Diluting with water yields a stable dispersion or solution of the active substance.

[0208] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0209] 50-80 wt% of Compound I was milled in a rotor-stator mill with the addition of 1-5 wt% dispersant (e.g., sodium lignosulfonate), 1-3 wt% wetting agent (e.g., alcohol ethoxylate), and up to 100 wt% solid support (e.g., silica gel). The mixture was diluted with water to obtain a stable dispersion or solution of the active substance.

[0210] viii) Gel (GW, GF)

[0211] In a stirred ball mill, 3-10 wt% of a dispersant (e.g., sodium lignin sulfonate), 1-5 wt% of a thickener (e.g., carboxymethyl cellulose), and 5-25 wt% of compound I were added and submerged in water to 100 wt% to obtain a fine suspension of the active substance. The suspension was then diluted with water to obtain a stable suspension of the active substance.

[0212] ix) Microemulsion (ME)

[0213] Add 5-20 wt% of Compound I to 5-30 wt% of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and 100 wt% of water. Stir the mixture for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0214] x) Microcapsules (CS)

[0215] An oil phase comprising 5-50 wt% Compound I, 0-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15 wt% acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylates) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% Compound I of the present invention, 0-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbons), and isocyanate monomers (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. wt% refers to the entire CS composition.

[0216] xi) Sprinkleable powder (DP, DS)

[0217] 1-10% by weight of compound I is finely ground and thoroughly mixed with a solid support (e.g., finely crushed kaolin) added up to 100% by weight.

[0218] xii) Particles (GR, FG)

[0219] 0.5-30 wt% of Compound I is finely ground and combined with up to 100 wt% of a solid support (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0220] xiii) Ultra-low volume liquids (UL)

[0221] Dissolve 1-50% by weight of compound I in an organic solvent (e.g., an aromatic hydrocarbon) added up to 100% by weight.

[0222] Composition types i)-xiii) may optionally contain other adjuvants, such as 0.1-1 wt% bactericide, 5-15 wt% antifreeze, 0.1-1 wt% defoamer and 0.1-1 wt% colorant.

[0223] Agricultural chemical compositions typically contain 0.01-95% by weight, preferably 0.1-90% by weight, more preferably 1-70% by weight, and especially 10-60% by weight of active material. The active material is used at a purity of 90-100%, preferably 95-100% (based on NMR spectroscopy).

[0224] For treating plant propagating material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. The compositions, after dilution 2-10 times, provide an active substance concentration of 0.01-60% by weight, preferably 0.1-40% by weight, in ready-to-use formulations. Application can be carried out before or during sowing. Methods of applying compound I and its compositions to plant propagating material, especially seeds, include seed dressing, coating, granulation, dusting, soaking, and furrow application. Preferably, compound I or its compositions are applied to the plant propagating material by methods that do not induce germination, such as seed dressing, granulation, coating, and dusting.

[0225] When used for plant protection, the amount of active substance applied depends on the type of desired effect and is 0.001-2 kg / ha, preferably 0.005-2 kg / ha, more preferably 0.05-0.9 kg / ha, and especially 0.1-0.75 kg / ha.

[0226] In the treatment of plant propagation materials such as seeds, for example by powdering, coating or soaking, the amount of active substance is generally required to be 0.1-1000g / 100kg, preferably 1-1000g / 100kg, more preferably 1-100g / 100kg, and most preferably 5-100g / 100kg of plant propagation material (preferably seeds).

[0227] When used to protect materials or store products, the amount of active substance applied depends on the type of area to be treated and the desired effect. Commonly used application rates for material protection include, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[0228] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and other pesticides (e.g., herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) can be added as premixes to active substances or compositions containing them, or, if appropriate, added (in a barrel mix) immediately before use. These agents can be mixed with the compositions of the present invention at a weight ratio of 1:100-100:1, preferably 1:10-10:1.

[0229] Pesticides are generally chemical or biological agents (such as phytotoxic active ingredients, compounds, compositions, viruses, bacteria, antimicrobial agents, or disinfectants) that, through their effects, prevent, disable, kill, or otherwise thwart harmful substances. Targeted harmful substances can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that damage property, cause trouble, spread disease, or act as disease vectors. The term "pesticide" also includes plant growth regulators that alter the expected growth, flowering, or reproductive rate of plants; defoliants that cause leaves or other foliage to fall from the plant, which generally promotes harvesting; desiccants that promote the drying of living tissues, such as unwanted above-ground parts of plants; plant activators that activate plant physiological functions to defend against certain harmful substances; safeners that reduce the undesirable herbicidal effects of pesticides on crops; and plant growth promoters that affect plant physiological functions, such as enhancing plant growth, biomass, yield, or any other quality parameter of the harvestable product of the crop.

[0230] Users typically use the compositions of this invention in pre-dosing devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. The agrochemical composition is usually formulated with water, buffers, and / or other adjuvants to the desired application concentration to obtain a ready-to-use spray or the agrochemical composition of this invention. 20-2000 liters, preferably 50-400 liters, of ready-to-use spray are typically applied per hectare of agricultural land.

[0231] According to one embodiment, the user can mix the components of the composition of the present invention in a spray can or any other type of container for application (e.g., seed treatment drum, seed granulator, backpack sprayer), such as parts of a package or parts of a binary or ternary mixture, and other adjuvants may be added if appropriate.

[0232] Therefore, one embodiment of the present invention is a kit for preparing useful pesticide compositions, the kit comprising a) a composition comprising component 1) as defined herein and at least one adjuvant; and b) a composition comprising component 2) as defined herein and at least one adjuvant; and optionally c) a composition comprising at least one adjuvant and optionally another active component 3) as defined herein.

[0233] I. Synthesis

[0234] I.1) Preparation of 4-[(Z)-N'-hydroxymethylamidinoyl]benzoic acid

[0235] Hydroxylamine hydrochloride (495 g, 2.0 eq.) and potassium carbonate (751 g, 1.5 eq.) were added to a solution of 4-cyanobenzoic acid (500 g, 1.0 eq.) in a mixture of ethanol and water (5 L / 2 L). 8-Hydroxyquinoline (6.5 g, 0.1 eq.) was added to the resulting mixture and heated under reflux until HPLC showed complete conversion of the starting material. After cooling to ambient temperature, water was added, and the resulting precipitate was collected and dried to give the title compound, which was of sufficient purity for direct use without further purification.

[0236] I.2) Preparation of 4-[5-trifluoromethyl-1,2,4- [diazol-3-yl]benzoic acid

[0237] A solution of 4-[(Z)-N'-hydroxymethylammonium]benzoic acid (200 g, 1.0 eq.) in tetrahydrofuran (2.5 L) was treated with trifluoroacetic anhydride (350 g, 1.5 eq.). The resulting mixture was stirred overnight at ambient temperature, then diluted with methyl tert-butyl ether and washed with a saturated aqueous sodium bicarbonate solution. The solvent was removed under reduced pressure to give a crude product, which was recrystallized from diisopropyl ether to give the title compound (220 g, 76%) as a light brown solid. 1 H NMR (400MHz, DMSO-d6, 298K): δ [ppm] = 13.40 (br.s, 1H), 8.22-8.10 (m, 4H).

[0238] I.3) Preparation of 4-[5-trifluoromethyl-1,2,4- [diazol-3-yl]benzoyl chloride

[0239] Add 4-[5-trifluoromethyl-1,2,4-] to a 250 mL round-bottom flask Diazol-3-yl]benzoic acid (20 g, 1.0 eq.) was added dropwise with thionyl chloride (50 mL, 5 eq.). Two drops of N,N-dimethylformamide were added to the suspension, and the mixture was warmed to gentle reflux and maintained for 2 hours. When HPLC showed complete conversion of the starting material, the mixture was cooled to room temperature and all volatiles were removed under reduced pressure. The residue was dissolved in toluene and co-evaporated to remove residual thionyl chloride. The title compound (20.7 g, 97%) was isolated as a light brown solid. 1 H NMR (400MHz, CDCl3, 298K): δ [ppm] = 8.35-8.25 (m, 4H).

[0240] I.4) Preparation of N,N-dimethyl-4-[5-trifluoromethyl-1,2,4- [diazol-3-yl]benzamide

[0241] 4-[5-trifluoromethyl-1,2,4- A solution of diazol-3-yl]benzoyl chloride (1.5 g, 1.0 eq.) and dimethylamine (10.8 mL, 2 M, in THF, 4 eq.) in tetrahydrofuran (120 mL) was stirred overnight, then the reaction was terminated by adding water and the product was extracted into dichloromethane. The combined organic layers were washed successively with dilute aqueous hydrochloric acid and dilute aqueous sodium bicarbonate solution, dried over sodium sulfate and the solvent was removed under reduced pressure to give the title compound (1.46 g) which could be used directly without further purification.

[0242] I.5) Preparation of N,N-dimethyl-4-[5-trifluoromethyl-1,2,4- [Diazol-3-yl]phenylthiocarboxamide (Compound Example 7)

[0243] To N,N-dimethyl-4-[5-trifluoromethyl-1,2,4- [Diazol-3-yl]benzamide (200 mg, 1.0 eq.) was added to a solution of 2,4-bis(4-methoxyphenyl)-2,4-dithio-1,3,2,4-dithiadiphosphetane (170 mg, 0.6 eq.) in toluene (2.5 mL). The resulting mixture was heated under reflux until HPLC showed complete conversion of the starting material. After cooling to ambient temperature, the mixture was concentrated under reduced pressure. The residue was purified by rapid chromatography to give the title compound (0.10 g, 79%). 1 H NMR (400MHz, CDCl3, 298K): δ [ppm] = 8.16 (d, 2H), 7.48 (d, 2H), 3.61 (s, 3H), 3.20 (s, 3H).

[0244] Prepare the compounds listed in Table I in a similar manner.

[0245] Table I: Examples 1-29 of compounds of formula I, wherein A corresponds to formula (A.2), wherein the group (A.2) is not substituted, and wherein R 1 and R 2 The meaning is as defined in each line.

[0246]

[0247]

[0248] *HPLC: High-performance liquid chromatography; HPLC column: Kinetex XB C18 1.7μm (50×2.1mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient 5:95-100:0 over 1.5 min at 60℃, flow rate gradient 0.8-1.0 ml / min over 1.5 min). MS: Quadrupole electro-ionization, 80V (positive mode). R t Retention time, in minutes.

[0249] II. Biological Examples of Antifungal Activity

[0250] A. Greenhouse Experiment

[0251] The fungicidal activity of the compound of formula I was confirmed by the following tests. A spray solution was prepared in several steps. A mixture of acetone and / or dimethyl sulfoxide in a solvent / emulsifier ratio (volume) of 99:1 with an ethoxylated alkylphenol-based wetting / emulsifier, Wettol, was added to 25 mg of the compound to make a total volume of 5 ml. Water was then added to a total volume of 100 ml. The stock solution was diluted to a given concentration with the solvent-emulsifier-water mixture.

[0252] 1. Therapeutic control of soybean rust caused by *Pseudomonas beanus* rust fungus on soybeans.

[0253] The leaves of potted soybean seedlings were inoculated with spores of *Solanum spp.* rust. To ensure successful artificial inoculation, the plants were transferred to a humid room at approximately 95% relative humidity and 20-24°C for 24 hours. The following day, the plants were cultivated in a greenhouse for 3 days at 23-27°C and 60-80% relative humidity. The plants were then sprayed to drip level with an aqueous suspension containing the active ingredients or mixtures thereof at the concentrations described below. The plants were then air-dried. The test plants were then cultivated in a greenhouse for 14 days at 23-27°C and 60-80% relative humidity. The degree of fungal infection on the leaves was assessed visually as a percentage of diseased leaf area.

[0254] In this experiment, plants treated with 32 ppm of the active compound in Examples 1, 2, 3, 4, 5, 7, 8, 9, 11, 12, 13, 15, 16, 17, 18, 19, 20, 21, 28, 32, 39, 43, 44 and 45 showed up to 15% diseased leaf area, while untreated plants showed 90% diseased leaf area.

[0255] 2. Protective control of soybean rust caused by *Solanum tumefaciens* on soybeans.

[0256] Spray the leaves of potted soybean seedlings with an aqueous suspension containing the active ingredients or mixtures thereof at the concentrations described below until dripping. Allow the plants to air dry. Cultivate the test plants in a greenhouse for 2 days at 23-27°C and 60-80% relative humidity. Then inoculate the plants with spores of *Potamogeton crispus*. To ensure successful artificial inoculation, transfer the plants to a humid chamber at approximately 95% relative humidity and 20-24°C for 24 hours. Cultivate the test plants in a greenhouse for 14 days at 23-27°C and 60-80% relative humidity. Assess the degree of fungal infection on the leaves visually as a percentage of diseased leaf area.

[0257] In this experiment, plants treated with 32 ppm of the active compound in Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 25, 27, 28, 30, 32, 34, 35, 36, 39, 40, 42, 43, 44, and 45 showed up to 15% diseased leaf area, while untreated plants showed 90% diseased leaf area.

[0258] 3. Therapeutic control of brown rust caused by wheat leaf rust fungus on wheat.

[0259] The first two leaves of potted wheat seedlings were powdered with spores of wheat leaf rust fungus. To ensure successful artificial inoculation, the plants were transferred to a dark, humid chamber at 95-99% relative humidity and 20-24°C for 24 hours. The next day, the plants were cultivated in a greenhouse at 20-24°C and 65-70% relative humidity for 3 days. The plants were then sprayed with an aqueous suspension containing the active ingredients or mixtures thereof at the concentrations described below until dripping. The plants were then air-dried. The test plants were then cultivated in a greenhouse at 20-24°C and 65-70% relative humidity for 8 days. The degree of fungal infection on the leaves was assessed visually as a percentage of diseased leaf area.

[0260] In this experiment, plants treated with 63 ppm of the active compound in Examples 1, 2, 3, 4, 9, 10, 17, 18, 19, 21, 28, 29, 43, 44 and 45 showed up to 15% diseased leaf area, while untreated plants showed 90% diseased leaf area.

[0261] 4. Preventive control of brown rust caused by wheat leaf rust fungus on wheat.

[0262] Spray the first two leaves of potted wheat seedlings with an aqueous suspension containing the active ingredients or mixtures thereof at the concentrations described below, until dripping. Seven days later, inoculate the plants with spores of wheat leaf rust fungus. To ensure successful artificial inoculation, transfer the plants to a dark, humid chamber at 95-99% relative humidity and 20-24°C for 24 hours. Then, cultivate the test plants in a greenhouse at 20-24°C and 65-70% relative humidity for 6 days. Assess the degree of fungal infection on the leaves visually as a percentage of diseased leaf area.

[0263] In this experiment, plants treated with 63 ppm of the active compound in Examples 1, 3, 4, 8, 9, 10, 12, 13, 16, 17, 18, 19, 28, 43, 44 and 45 showed up to 15% diseased leaf area, while untreated plants showed 80% diseased leaf area.

Claims

1. A compound of formula I or an agriculturally usable salt thereof: in: A is phenyl; and the cyclic group A is not substituted. R 1 It is hydrogen or methyl; and wherein the above aliphatic group is not substituted; and R 2 It is a C1-C6 alkyl group; and wherein the above-mentioned aliphatic group is not substituted.

2. The compound according to claim 1, wherein the trifluoromethyl group is... diazole group and -C(=S)NR 2 -R 1 The groups are located in the para position on the phenyl ring to which they are attached.

3. The compound according to claim 1 or 2, wherein R 1 It is hydrogen or methyl and R 2 It is methyl, ethyl, n-propyl, isopropyl, n-butyl, or isobutyl; and any aliphatic group therein is not substituted.

4. The compound according to claim 1 or 2, wherein R 1 It is hydrogen and R 2 It is methyl; and any aliphatic group therein is not substituted.

5. The compound according to claim 1 or 2, wherein R 1 It is methyl and R 2 It is an ethyl group; and any aliphatic group therein is not substituted.

6. An agricultural chemical composition comprising an adjuvant and at least one compound of formula I according to any one of claims 1-5 or an agriculturally usable salt thereof.

7. The agricultural chemical composition according to claim 6, wherein the adjuvant is selected from the group consisting of ionic or nonionic surfactants.

8. The agricultural chemical composition according to claim 6 or 7, comprising at least one other pesticide active substance selected from herbicides, safeners, fungicides, insecticides and plant growth regulators.

9. The agricultural chemical composition according to claim 6 or 7, further comprising seeds, wherein the amount of the compound of formula I or its arable salt is 0.1 g to 10 kg / 100 kg of seeds.

10. Use of the compound or its agriculturally usable salt according to any one of claims 1-5 in the control of pathogenic harmful fungi in plants.

11. A method for controlling plant pathogenic harmful fungi, the method comprising treating the fungi or plants, soil or seeds to be protected against fungal invasion with an effective amount of at least one compound of formula I as defined in any one of claims 1-5 or an agriculturally usable salt thereof.

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