EA042940B1 - PYRIDINE AND PYRAZINE COMPOUNDS - Google Patents

Description

The present invention relates to pyridine and pyrazine compounds and their salts for controlling phytopathogenic fungi, and to uses and methods for controlling phytopathogenic fungi, and to seeds coated with at least one such compound. The invention also relates to methods for the preparation of such compounds, intermediates, methods for the preparation of such intermediates, and compositions containing at least one compound I.

In many cases, in particular at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, the aim of the present invention was to provide compounds having improved activity and/or a broader spectrum of activity against phytopathogenic harmful fungi.

Surprisingly, this object has been achieved by the use of pyridine compounds of the formula I according to the invention, which have a favorable fungicidal activity against phytopathogenic fungi.

Accordingly, the present invention relates to compounds of formula I

Where

R ¹ means C ₁ -C ₆ -alkyl;

R ² means C ₁ -C ₆ -alkyl;

U means N or CR ³ ;

R ³ means H;

R ⁴ is selected from H, C ₁ -C ₆ alkyl;

Y means O;

Z means CR ⁵ ;

R ⁵ means H;

X is independently selected from halogen;

n means 1;

Q ¹ is selected from C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl;

Q ² is selected from H, C ₁ -C ₆ -alkyl;

W means O or NQ ⁴ ;

Q ³ is selected from C1-C15-alkyl substituted with phenyl, where phenyl is unsubstituted or substituted by halogen, C(=O)C1-C15-alkyl, C(=O)phenyl, where aliphatic fragments of the Q ³ group, with the exception of substituted C1- The C ₁₅ alkyl moieties are unsubstituted or substituted with the same or different Q ^3a groups independently selected from the following:

Q ^3a halogen, C ₁ -C ₆ -alkoxy, phenyl, where the phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q ^31a selected from the group consisting of halogen, where the phenyl group Q ³ is not substituted or substituted with 1, 2, 3, 4, 5 or up to the maximum possible number of the same or different Q ^3b groups, which are independently selected from the following:

Q ^3b halogen, phenyl, where the phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q ^311b selected from the group consisting of halogen;

Q ⁴ means H;

provided that if

U stands for CR ³

W cannot be O;

and their agriculturally acceptable salts.

The numbering of the ring members in the compounds of the present invention is as indicated in formula I above.

Type I compounds can be prepared by reacting type II compounds with a suitable Q ³ LG electrophile in an organic solvent, preferably NMP or halocarbon, and in the presence of a base at temperatures between -20 and 100°C, most preferably between 0 and 40°C. LG is a suitable leaving group, preferably a halogen or a sulfonate.

- 1 042940

Alternatively, compounds I can be prepared by reacting compounds II* with compounds Q3-W-H under the conditions described for the reaction between compounds II and Q3-LG to give compounds I.

Compounds of type I-1 can also be prepared by reacting compounds II** with compounds Q3*-CN under the conditions described for the reaction between compounds II and Q3-LG to give compounds I-1

By

Compounds of type I-2 can be prepared onionically, preferably by reaction with a Q4-LG reactive group. The reactions are C _g C ₈ -alkyl halides, C ₂ -C ₆ alkenyl halides, C ₂ -C 6 alkynyl halides, benzyl halides, aldehydes, esters, acid chlorides, amides, sulfates, silyl halides or phosphates, for example, carboxylic acids (LG \u003d OH) , aldehydes (LG = H), acid chlorides (LG = Cl), amides (LG = NMe ₂ ) or phosphates (LH = OCH3).

Typically, the reaction is carried out at a temperature in the range between 0° C. and ambient temperature in the presence of a reactive group and an organic base. A suitable base is preferably NEt ₃ , pyridine, NaOH, TEBAC, K ₂ CO ₃ , NaCO ₃ or KOH. The most preferred solvents are THF, DMF, DMSO, MeOH or water (see, for example, Journal of Medicinal Chemistry, 1989, 32(6), 1242-1248; European Journal of Medicinal Chemistry, 2009, 44(10), 4034- 4043).

Type II compounds can be prepared as described, for example, in JP 2010/202530 or Angewandte Chemie, International Edition, 45(35), 5803-5807; 2006 and as set out below. Type III compounds (where Hal is halogen, most preferably Br or I) can be metallated by treatment with the appropriate organometallic reagent [M] in an ethereal solvent at low temperatures. Preferably, an organolithium or organomagnesium compound is used, the reaction being best carried out in THF and at a temperature between -78 and 0°C. Intermediate organometallic compounds can be captured by carbonyl, thiocarbonyl or imine type IV compounds to form type II compounds after treatment with water. Type IV compounds are readily available, either from commercial suppliers or by methods that are obvious to those skilled in the art.

- 2 042940

For the preparation of type III compounds, it may be preferable to react compounds V by nucleophilic aromatic substitution with type VI compounds, which are either commercially available or can be prepared according to procedures that are obvious to the person skilled in the art. LG is a suitable leaving group, with fluorine being particularly preferred (see, for example, WO 2007/117381, WO 2012/037782, or Bioorganic & Medicinal Chemistry, 21(4), 979-992; 2013) for examples. The reaction is best carried out at temperatures between 0 and 100°C, preferably in the range between room temperature and 80°C. In addition, it may be useful to carry out the reaction in an organic solvent, preferably, but not limited to, DMF or NMP, and in the presence of a base, preferably, but not limited to, potassium carbonate or sodium hydride.

Alternatively, compounds III can be synthesized by reacting compounds V* and VI* using the conditions already described for the reaction of compounds V with compounds VI.

Alternatively, compounds III* can be prepared by reacting compounds V* with compounds VI** using the conditions already described for the reaction of V* with VI* to give compounds III*. Compounds III* can then be converted to compounds II using the methods already described for the reaction of compounds III with compounds IV to give compounds II

can be obtained by the reaction of compounds V with compounds VI***,

In addition, compounds III* using the conditions already described for the reaction of V* with VI* to obtain compounds III*.

Type V compounds can be prepared from type VII nitro compounds in a two-step sequence as previously described (for examples see Journal of Medicinal Chemistry, 35(20), 3667-71; 1992, WO 2005/123668 or US 20060293364). In the first step, the nitro group is chemoselectively reduced to its amino derivative by using a suitable reducing agent such as iron, zinc or hydrogen in the presence of a transition metal catalyst such as palladium. Preferably the reduction is carried out in an organic solvent, more preferably

- 3 042940 respectfully in an alcoholic solvent, if necessary at elevated temperatures and/or elevated pressures. The corresponding amino compounds can be converted to type V compounds by a Sandmeyer reaction, starting with their reaction with a suitable source of nitrite at low temperatures, preferably, but not limited to, sodium nitrite or t-BuONO. To prepare compounds in which Y is oxygen, the diazonium salt intermediate can be treated with a suitable acid, such as, but not limited to, HCl or HBF4. It may be helpful to increase the temperature as the acid is added. Compounds in which Y is S can be prepared by reacting said diazonium salt with a suitable source of sulfur, preferably an alkali metal xanthate such as potassium xanthate, followed by base mediated cleavage of the thioester. An example can be found, for example, in Journal of Medicinal Chemistry, 36(8), 953-66; 1993.

_d 2 1. restore ^R VV ^NO? yh i JL JL l ^{2 reaction} IJ

R'^NR Sandmeier rI^^N'^R ⁴

VIIv

It will be clear to one skilled in the art that Type VII compounds are either commercially available or can be prepared according to standard procedures.

N-oxides can be obtained from the compounds of the invention according to conventional oxidation methods, for example by treating compounds I with an organic peracid such as metachloroperbenzoic acid (see WO 03/64572 or J. Med. Chem. 38(11), 1892- 903, 1995); or inorganic oxidants such as hydrogen peroxide (see J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (see J. Am. Chem. Soc. 123(25), 5962-5973, 2001). Oxidation can lead to pure MOHO-N-oxides, or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

The intermediate compounds are further described in the following. The person skilled in the art will readily appreciate that substituent preferences, in particular also those indicated in the tables below for the respective substituents given herein in connection with compounds I, apply respectively to the intermediates. Thus, the substituents in each case have the meanings as defined herein independently of each other or, more preferably, in combination with each other.

If the synthesis yields mixtures of isomers, separation is usually not necessary, since in some cases the individual isomers may interconvert during their processing before use or during use itself (for example, under the action of light, acids or bases). Such transformations can also take place after application, for example, in a plant treatment in the treated plant, or in the harmful fungus to be controlled.

In the definitions of the variables above, collective terms are used that are generally representative of the substituents in question. The term C _n -C _m indicates the number of carbon atoms possible in each case in the substituent or fragment of the substituent in question.

The term halogen refers to fluorine, chlorine, bromine and iodine.

The term C ₁ -C ₆ alkyl refers to a straight or branched chain saturated hydrocarbon group containing from 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, pentyl, 1-methylbutyl, 2methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl , 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1.1 ,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2methylpropyl. Similarly, the term C ₂ -C ₄ -alkyl refers to a straight chain or branched alkyl group containing from 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec -butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl).

The term C ₁ -C ₆ -haloalkyl refers to an alkyl group containing from 1 to 6 carbon atoms, as defined above, where some or all of the hydrogen atoms in these groups can be replaced by halogen atoms, as mentioned above. Examples are C1- _C2 haloalkyl groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2trichloroethyl or pentafluoroethyl.

The term C ₁ -C ₆ -hydroxyalkyl refers to an alkyl group containing 1 or 6 carbon atoms, as defined above, where some or all of the hydrogen atoms in these groups may be replaced by OH groups.

The term C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl refers to alkyl containing from 1 to 4 carbon atoms

- 4 042940 (according to the above definition), where one hydrogen atom of the alkyl radical is replaced by

a C1-C4 alkoxy group (as defined above). Similarly, the term C ₁ -C ₆ alkoxy-C 1 -C ₄ -alkyl refers to alkyl containing from 1 to 4 carbon atoms (as defined above), where one hydrogen atom of the alkyl radical is replaced by C ₁ -C ₆ -alkoxy group (according to the above definition).

The term C ₂ -C ₆ alkenyl refers to a straight chain or branched unsaturated hydrocarbon radical containing from 2 to 6 carbon atoms and a double bond in any position. Examples are C ₂ -C ₄ -alkenyl groups such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2- methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.

The term C2-C6 alkynyl refers to a straight chain or branched unsaturated hydrocarbon radical containing 2 to 6 carbon atoms and at least one triple bond. Examples are C ₂ -C ₄ alkynyl groups such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl, 1- methylprop-2-ynyl.

The term C ₁ -C ₆ -alkoxy refers to a straight chain or branched alkyl group containing from 1 to 6 carbon atoms, which is attached through an oxygen atom at any position in the alkyl group. Examples are C ₁ -C ₄ alkoxy groups such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.

The term C ₁ -C ₆ haloalkoxy refers to a C ₁ -C ₆ alkoxy radical as defined above, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are C1- _C4 haloalkoxy groups such as OCH2F, OCHF2, OCF ₃ , OCH ₂ Cl, OCHCl ₂ , OCCl ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 ,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2fluoropropoxy , 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3trichloropropoxy , OCH2-C2F5, OCF2-C2F5, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, or nonafluorobutoxy.

The term C ₂ -C ₆ -alkenyloxy refers to a straight chain or branched alkenyl group containing from 2 to 6 carbon atoms, which is attached through an oxygen atom at any position in the alkenyl group. Examples are C ₂ -C ₄ -alkenyloxy groups.

The term C2-C6 alkynyloxy refers to a straight chain or branched alkynyl group containing from 2 to 6 carbon atoms, which is attached via an oxygen atom at any position in the alkynyl group. Examples are C2-C4 alkynyloxy groups.

The term C3-C6-cycloalkyl refers to monocyclic saturated hydrocarbon radicals containing from 3 to 6 carbon atoms - ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered carbocyclyl or carbocycle is a C ₃ -C ₁₀ cycloalkyl.

The term C ₃ -C ₆ -cycloalkenyl refers to a monocyclic partially unsaturated 3-, 4-, 5- or 6-membered carbocycle containing from 3 to 6 carbon atoms - ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexadienyl . Accordingly, a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocyclyl or carbocycle is a C ₃ -C ₁₀ -cycloalkenyl.

The term C ₃ -C ₈ -cycloalkyl-C1-C ₄ -alkyl refers to alkyl containing from 1 to 4 carbon atoms (as defined above), where one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical containing from 3 to 8 atoms carbon (according to the above definition).

The term C ₁ -C ₆ -alkylthio in the context of this document refers to straight chain or branched alkyl groups containing from 1 to 6 carbon atoms (as defined above) attached via a sulfur atom. Accordingly, the term Ο ₁ -Ο ₆ haloalkylthio as used herein refers to a straight chain or branched haloalkyl group containing from 1 to 6 carbon atoms (as defined above) attached via a sulfur atom at any position in the haloalkyl group.

The term C(=O)-C1-C ₆ alkyl refers to a radical that is attached via a carbon atom of a C(=O) group as indicated by the valence number of the carbon atom. The valence number of carbon is 4, and nitrogen is 3. The following terms should be interpreted in a similar way: NH (C ₁ -C ₄ -alkyl), N (C ₁ -C ₄ -alkyl) ₂ , NH (C ₃ -C ₆ -cycloalkyl) , N(C ₃ -C ₆ -cycloalkyl) ₂ , C (=O)-NH (C ₁ -C ₆ -alkyl), C (=O) -N (C ₁ -C ₆ -alkyl) ₂ .

The term saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered heterocyclyl or heterocycle, where the heterocyclyl or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, should be understood to mean both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include, in addition to carbon atoms, 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, N, and S. For example:

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3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members, such as oxirane, aziridine, thiirane, oxetane, azetidine, thietane, [1,2] dioxetane, [1,2]dithiethane, [1,2]diazetidine; And

A 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1, 2 or 3 heteroatoms from the group consisting of O, N and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2oxazolidinyl, 4-oxazolidinyl, 5- oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin- 3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3- yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin- 4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5- yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2, 3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol- 1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3- yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazine- 2-yl and 1,2,4-hexahydrotriazin-3-yl as well as the corresponding ylidene radicals and a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl such as 2,3,4,5tetrahydro[1H] azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3- , -4-, -5-, -6 or -7-yl, 2,3,4,7-tetrahydro[1H]azepine-1-, -2-, -3-, -4-, -5-, - 6-or-7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydro-oxepinyl such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl , 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or-7-yl, hexahydroazepin-1-, -2-, -3 or -4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl and the corresponding ylidene radicals.

The term substituted refers to substitution with 1, 2, 3 or up to the maximum possible number of substituents.

The term 5- or 6-membered heteroaryl or 5- or 6-membered heteroaromatic refers to aromatic ring systems containing, in addition to carbon atoms, 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, O, and S, e.g. , means

5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazole -1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl , oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3 -yl, isothiazol-4-yl, isothiazol-5yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl or

6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidine -5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl, and 1,2,4-triazin-3-yl.

The agriculturally acceptable salts of the compounds according to the invention mainly comprise the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the fungicidal action of said compounds. Thus suitable cations are in particular alkali metal ions, preferably sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, transition metals, preferably manganese, copper, zinc and iron, as well as ammonium ions, which, may optionally carry one to four C1- _C4 alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium ions, in addition phosphonium ions, sulfonium ions, preferably tri(C1- _C4 -alkyl)sulfonium; and sulfoxonium ions, preferably tri(C1- _C4 alkyl)sulfoxonium. Suitable acid addition salt anions are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1- _C4- alkanoic acids. , preferably formate, acetate, propionate and butyrate. They can be obtained by reacting such a compound according to the invention with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

Compounds according to the invention may be present as atropisomers resulting from limited rotation around a single bond linking asymmetric groups. They also form part of the subject matter of the present invention.

Depending on the substitution scheme, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers, or as a mixture of enantiomers or diastereomers. Both pure enantiomers or diastereomers and mixtures thereof are the subject of the present invention.

The following describes individual embodiments of the compounds according to the invention. In the course of this, the specific meanings of the respective substituents are further detailed, where the meanings in each case, both alone and in any combination with each other, represent separate embodiments of the present invention.

Moreover, as far as variables are concerned, compound variants I generally also apply to intermediates.

According to one variant of formula I, R1 is C ₁ -C ₆ alkyl, in particular C 1 -C ₄ alkyl, such as CH3 or C2H5, in particular CH3 or CH2CH3.

Particularly preferred variants of R in accordance with the invention are presented in table. P1 below, where each line of lines P1-1 -P1-9 corresponds to one single embodiment of the invention, where P1-1 - P1-9 in any combination with each other also represent a preferred embodiment of the present invention. The place of attachment of R ¹ to the carbon atom is marked on the structural formulas with #.

Table P1

No. ^R1 R1-1 CH ₃ R1-2 C ₂ H ₅ R1-3 CH (CH ₃ ) ₂ R1-4 CH ₂ CH ₂ CH ₃ R1-5 CH ₂ CH ₂ CH ₂ CH ₃ R1-6 CH ₂ CH (CH3) ₂ R1-7 C (CH ₃ ) R1-8 CH ₂ CH ₂ CH ₂ CH ₂ CH ₃ R1-9 CH ₂ CH ₂ CH (CH3) ₂

According to one variant of formula I, R ² is C ₁ -C ₆ alkyl, in particular C 1 -C ₄ alkyl, such as CH ₃ or C ₂ H ₅ , in particular CH ₃ or CH ₂ CH ₃ .

Particularly preferred variants of R ² in accordance with the invention are presented in table. P2 below, where each line of lines P2-1 - P2-9 corresponds to one particular embodiment of the invention, where P2-1 - P2-9 in any combination with each other also represent a preferred embodiment of the present invention. The place of attachment of R ² to the carbon atom is marked on the structural formulas by #.

Table P2

No. ^R2 R2-1 SNz R2-2 from ₂ to ₅ R2-3 CH (CH ₃ ) ₂ R2-4 CH ₂ CH ₂ CH ₃ R2-5 CH ₂ CH ₂ CH ₂ CH ₃

No. ^R2 R2-6 CH ₂ CH (CH ₃ ) ₂ R2-7 C (CH ₃ ) R2-8 CH ₂ CH ₂ CH ₂ CH ₂ CH3 R2-9 CH ₂ CH ₂ CH (CH ₃ ) ₂

U according to the invention means N or CR3. According to one version of Formula I, U is N. According to another version of Formula I, U is CR ³ . In accordance with another variant of formula I, R ³ means hydrogen. In accordance with another variant of formula I, R ⁴ means hydrogen. In accordance with another variant of formula I, R ⁴ means C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl, such as CH3 or CH2CH3.

Particularly preferred variants of R ⁴ in accordance with the invention are presented in table. R4

- 7 042940 below, where each line of lines P4-1 - P4-3 corresponds to one separate embodiment of the invention. Thus, for each R ⁴ group that is present in the compounds according to the invention, these particular embodiments and preferences apply regardless of the meaning of any other R ⁴ that may be present on the ring:

Table P4

According to one variant of Formula I, Y is O.

Z according to the invention means CR ⁵ .

According to one particular embodiment, R ⁵ is H.

According to one particular embodiment, n is 1.

According to one particular embodiment, X is halogen, in particular F, Cl, Br or I, more in particular F, Cl or Br, in particular F or Cl.

In accordance with another variant of formula I, X means F.

In accordance with another variant of the formula I X means Cl.

In accordance with another variant of formula I, X is Br.

According to a further specific embodiment, Q ¹ is C1-C ₆ -alkyl, in particular C1-C ₄ -alkyl, such as CH ₃ or CH ₂ CH ₃ .

According to a further specific embodiment, Q ¹ is C ₁ -C ₆ haloalkyl, in particular C 1 -C ₄ haloalkyl, such as CF ₃ , CHF 2 , CH 2 F, CCl ₃ , CHCl ₂ or CH ₂ Cl.

Particularly preferred options for Q ¹ in accordance with the invention are presented in table. Q1 below, where each line of lines Q1-1 - Q1-12 corresponds to one single embodiment of the invention, where Q1-1 - Q1-12 in any combination with each other also represent a preferred embodiment of the present invention.

Table Q1 No. ^Q1 Q1-1 CH ₃ Q1-2 CH ₂ CH ₃ Q1-3 iso-Pr Q1-4 _CF3 Q1-5 chf ₂ Q1-6 ch ₂ f Q1-7 SS1 ₃ Q1-8 SNS1 ₂ Q1-9 CH ₂ C1 Q1-10 ch ₂ cf ₃ Q1-11 CH ₂ SS1z Q1-12 chf ₂ cf ₂

According to a further specific embodiment, Q ² is C1-C ₆ -alkyl, in particular C1-C ₄ -alkyl, such as CH ₃ or CH ₂ CH ₃ .

Particularly preferred options for Q ² in accordance with the invention are presented in table. Q1 below, where each line of lines Q2-1 - Q2-4 corresponds to one single embodiment of the invention, where Q2-1 - Q2-4 in any combination with each other also represent a preferred embodiment of the present invention:

Table Q2

No. X Q2-1 n Q2-2 SNz Q2-3 CH ₂ CH ₃ Q2-4 z/zo-Pr ^b

W in accordance with the invention means O or NQ ⁴ . According to one version of the formula, IW means O. According to another version of the formula, IU means CR ³ and W means NQ ⁴ .

According to one most preferred embodiment of formula I, U is N and W is O.

In accordance with one additional most preferred variant of formula I, U is N and W is NQ ⁴ .

In accordance with another variant of formula I, Q ³ means CrC ^-haloalkyl, in particular C ₁ -C ₇ -haloalkyl, such as CF ₃ , CCl ₃ , FCH2, ClCH ₂ , F2CH, Cl ₂ CH, CF ₃ CH ₂ , CCl ₃ CH ₂ or CF2CHF2.

In accordance with an additional special variant of the formula IQ ³ means C(=O)C1-C ₁₅ -alkyl, where alkyl means CH ₃ , C ₂ H ₅ , n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n -pentyl or isopentyl.

In accordance with an additional special variant of the formula IQ ³ means C(=O)phenyl, where the phenyl group is unsubstituted or carries one, two, three, four or five substituents R ^78a selected from the group consisting of halogen.

In accordance with another variant of the formula IQ ³ in each case independently selected from substituted C1-C15-alkyl, C(=O)C1-C15-alkyl, C(=O)phenyl, where acyclic fragments of the group Q ³ with the exception of substituted C1 -C ₁₅ -alkyl fragments are unsubstituted or substituted by the same or different groups Q ^3a as defined and preferably defined in this application; and where the substituted C ₁ -C ₁₅ -alkyl fragments of the group Q ³ substituted by the same or different groups Q ^3c as defined and preferably defined in this application.

Q ^3a means possible substituents for aliphatic fragments of the group Q ³ with the exception of substituted C ₁ -C ₁₅ -alkyl fragments.

In accordance with one preferred embodiment, Q ^3a is in each case independently selected from C ₁ -C6 alkoxy, such as OCF ₃ .

According to one preferred embodiment, Q ^3a is at each occurrence independently selected from phenyl, wherein the phenyl is substituted with a halogen selected from the group consisting of F, Cl and Br.

According to one preferred embodiment, Q ^3a is in each case independently selected from halogen, C ₁ -C 6 -alkoxy, phenyl; where phenyl is substituted with halogen selected from the group consisting of F, Cl and Br.

In accordance with one additional preferred embodiment, Q ^3a is independently selected from halogen, phenyl, where phenyl is substituted by halogen selected from the group consisting of F, Cl and Br, in particular selected from F and Cl.

In accordance with one additional preferred embodiment, Q ^3a is independently selected from halogen, C ₁ -C ₆ -alkoxy, phenyl, where phenyl is substituted by halogen selected from the group consisting of F, Cl and Br.

In accordance with one additional preferred embodiment, Q ^3a is independently selected from halogen and phenyl in each occurrence, where phenyl is substituted by halogen selected from the group consisting of F, Cl and Br, in particular selected from F and Cl.

Q ^3b means possible substituents for phenyl fragments of the group Q ³ .

Q ^3b according to the invention is independently selected from halogen, phenyl; and where the phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q ^311b selected from the group consisting of halogen.

In accordance with one further separate embodiment, Q ^3b is independently selected from halogen such as Cl, Br, F at each occurrence.

In accordance with another variant of formula I, Q ³ means C ₁ -C ₆ -alkyl, such as CH ₃ , C ₂ H ₅ , npropyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl, which is substituted by at least one R ^4c group, which in each case is independently selected from the following:

halogen, C1-C4 alkoxy, phenyl; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

In accordance with another variant of the formula IQ ³ means a group of CH3, which is substituted by at least one group Q ^3c which in each case, independently of each other, is selected from the following: halogen, C1-C ₄ -alkoxy, phenyl; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

In accordance with another variant of the formula IQ ³ means the group Et, which is substituted by at least one group Q ^3c in each case, independently of each other selected from the following: halogen, C1-C ₄ -alkoxy, phenyl and five-, six - or ten-membered heteroaryl, heterocycloxy, heteryloxy; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

In accordance with another variant of formula I, Q ³ means a group Pr, which is substituted by at least one group Q ^3c which in each case independently of each other is selected from the following: halogen, C 1 -C ₄ -alkoxy, phenyl; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

According to yet another variant of formula I, Q ³ is an iso-Pr group which is substituted by at least one Q ^3c group, which in each case is independently selected from the following: halogen, C1- _C4 - alkoxy, phenyl; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

In accordance with another variant of the formula IQ ³ means butyl group, which is substituted by at least one group Q ^3c which in each case independently of each other is selected from the following: halogen, C ₁ -C ₄ -alkoxy, phenyl; where the phenyl groups are independently substituted or carry one, two, three, four or five substituents Q ^31c selected from the group consisting of halogen.

In accordance with an additional special variant of formula I, Q ³ means C ₁ -C ₁₅ -alkyl-C ₁ -C ₆ alkoxy, in particular C ₁ -C ₇ -alkyl-C ₁ -C ₄ -alkoxy, more specifically C ₁ -C ₄ -alkyl-C ₁ -C ₂ -alkoxy, such as CH 2 OCH 3 , CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 , CH 2 CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 2 CH 3 .

In accordance with an additional special variant of the formula IQ ³ means C ₁ -C ₁₅ -alkyl-C ₁ -C ₆ haloalkoxy, in particular C ₁ -C ₇ -alkyl-C ₁ -C ₄ -haloalkoxy, more specifically C ₁ -C ₄ -alkyl-C ₁ -C ₂ haloalkoxy, such as CH2OCF3, CH2CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCC13, CH2OCHCI2 or CH2OCH2C1, in particular CH2OCF3, CH2OCHF2, CH2OCCI3 or CH2OCHCb

Particularly preferred options for Q ³ in accordance with the invention are presented in table. Q3 below, where each line of lines Q3-1-Q3-38 corresponds to one single embodiment of the invention, where Q3-1 to Q3-38 in any combination with each other also represent a preferred embodiment of the present invention:

No. Q ³ Q3-1 _CF3 Q3-2 chf ₂ Q3-3 CH ₂ CH ₂ DOS ₃ Q3-4 CH ₂ OCH ₂ F Q3-5 ch ₂ ochf ₂ Q3-6 ch ₂ ocf ₃ Q3-7 ch ₂ ocf ₂ chf ₂ Q3-8 -CH ₂ -C ₆ H ₅ Q3-9 -CH ₂ -C ₆ H ₄ -4-F Q3-10 -CH ₂ -C ₆ H ₄ -4-CH ₃ Q3-11 -CH ₂ -C ₆ H ₄ -3-CH ₃ Q3-12 -CH ₂ -C ₆ H ₄ -2-CH ₃ Q3-13 -CH(CH ₃ )-C ₆ H ₅ Q3-14 CH(CH ₃ )-C ₆ H ₄ -4-F Q3-15 CH(CH ₃ )-C ₆ H ₄ -4- CH ₃ Q3-16 CH(CH ₃ )-C ₆ H ₄ -3-CH ₃ Q3-17 CH(CH ₃ )-C ₆ H ₄ -2-CH ₃ Q3-18 COCH ₃ Q3-19 COCH ₂ CH ₃

No. Q ³ Q3-20 COCH ₂ CH ₂ CH ₃ Q3-21 CO(CH ₂ ) ₃ CH ₃ Q3-22 CO(CH ₂ ) ₄ CH ₃ Q3-23 CO(CH ₂ ) ₅ CH ₃ Q3-24 CO(CH ₂ ) ₆ CH ₃ Q3-25 COCC1 ₃ Q3-26 COCH ₂ C1 Q3-27 COCH ₂ -N(CH ₃ ) ₂ Q3-28 COPh Q3-29 _COCH2 Ph Q3-30 _COCH2 Ph-4-F Q3-31 _COCH2 Ph-4- _CH3 Q3-32 _COCH2 Ph-3- _CH3 Q3-33 _COCH2 Ph-2- _CH3 Q3-34 COCH( _CH3 )Ph Q3-35 COCH(CH ₃ )4-F Q3-36 COCH(CH ₃ )-4-CH ₃ Q3-37 COCH(CH ₃ )-3-CH ₃ Q3-38 COCH(CH ₃ )-3-CH ₃

In accordance with a variant of the IQ formula ^{, 4} means H.

Separate embodiments of compounds I are the following compounds: II-A, II-B, II-C, II-D, II-E, II-F. In these formulas, the substituents Q ¹ , Q ² and Q ³ independently of each other have the meanings as defined in paragraph 1 or preferably as defined below:

- 10 042940

Table 2-1. Compounds of formulas II-A, II-B, II-C, II-D, II-E, II-F, in which the values for the combination of Q ¹ , Q ² and Q ³ for each individual compound correspond in each case to one line of the table . A (compounds II-A.2-1.A-1 - I-A.2-1.A-45, II-B.2-1.A-1 - II-B.2-1.A-45 , H-C.2-1.A-1 - II-C.2-1.A-45,

II-D.2-1.A-1 - II-D.2-1.A-45, II-E.2-1.A-1 - I-E.2-1.A-45, II- F.2-1.A-1 - II-F.2-1.A-45).

Table A

No. Q ^{3 Q1 Q2} A-1 COSNz g/zo-CsN? H A-2 SOSN ₂ CH ₃ g/zo-SzN ₇ H A-3 COCH ₂ CH ₂ CH ₃ g/zo-CsN? n A-4 CO (CH ₂ ) CH ₃ g/zo-CsN? n A-5 CO (CH ₂ ) ₄ CH ₃ g/zo-CsN? n A-6 CO (CH ₂ ) ₅ CH ₃ iso-C ₃ H ₇ n A-7 CO (CH ₂ ) ₆ CH W30-C3H7 n A-8 SOSS13 g / zo-C ₃ H ₇ n A-9 COCH ₂ C1 W30-C3H7 n A-10 COPh iso-C ₃ H ₇ n A-11 _COCH2 Ph W30-C3H7 n A-12 _COCH2 Ph-4-F МЗ0-С3Н7 n A-13 COCH( _CH3 )Ph W30-C3H7 n A-14 COCH(CH ₃ )-4-F W30-C3H7 n A-15 COCH(CH ₃ )-4-CH3 W30-C3H7 n A-16 COCH(CH ₃ )-3-CH3 W30-C3H7 n A-17 COCH(CH ₃ )-3-CH3 W30-C3H7 n A-18 _CF3 iso-C ₃ H ₇ n A-19 chf ₂ W30-C3H7 n A-20 CH ₂ CH ₂ OCH ₃ W30-C3H7 n A-21 CH ₂ -C ₆ H ₅ iso-C ₃ H ₇ n A-22 CH ₂ -C ₆ H ₄ -4-F W30-C3H7 n A-23 CH (CH ₃ ) -C ₆ H ₅ iso-C ₃ H ₇ n A-24 CH(CH ₃ )-C ₆ H ₄ -4-F W30-C3H7 n A-25 COSNz W30-C3H7 SNz A-26 SOSN ₂ CH ₃ iso-C ₃ H ₇ SNz A-27 SOSN ₂ CH ₂ CH3 iso-C ₃ H ₇ SNz A-28 CO (CH ₂ ) CH ₃ W30-C3H7 SNz A-29 CO (CH ₂ ) ₄ CH3 ISO-C3H7 SNz A-30 CO (CH ₂ ) ₅ CH W30-C3H7 SNz A-31 CO (CH ₂ ) ₆ CH W30-C3H7 SNz A-32 SOSS13 U30-C3H7 SNz A-33 COCH ₂ C1 U30-C3H7 SNz A-34 COPh iso-Sznu SNz A-3 5 _COCH2 Ph U3O-C3H7 SNz A-36 _COCH2 Ph-4-F iso-CsH ₇ SNz A-37 COCH( _CH3 )Ph U30-C3H7 SNz A-3 8 COCH(CH ₃ )-4-F iso-Sznu SNz A-39 _CF3 1/30-С3Н7 SNz A-40 chf ₂ 1/30-С3Н7 SNz A-41 CH ₂ CH ₂ OCH ₃ 1/30-С3Н7 SNz A-42 CH ₂ -C ₆ H ₅ iso-CsH ₇ SNz A-43 CH ₂ -C ₆ H ₄ -4-F iso-C ₃ H ₇ SNz A-44 CH (CHz) -C ₆ H ₅ 1/30-С3Н7 SNz A-45 CH(CH ₃ )-C ₆ H ₄ -4-F 1/30-С3Н7 SNz

Separate embodiments of compounds I are the following compounds: IV-A, IVB, IV-C, IV-D, IV-E, IV-F, IV-G, IV-H, IV-I. In these formulas, the substituents R ¹ , R ² , R ⁴ and Q ³ independently of each other have the meanings as defined in paragraph 1 or preferably defined below:

- 11 042940

Table 4-1. Compounds of formulas IV-A, IV-B, IV-C, IV-D, IV-E, IV-F, IV-G, IV-H, IV-I, in which the values for the combination of Q ¹ , Q ² and Q ³ for each individual connection corresponds in each case to one line of the table. B (connections IV-A.4-1.B-1 - IV-A.4-1.B-48, IV-B.4-1.B-1 - IV-B.4-1.B-48 , IVC.4-1.B-1 - IV-C.4-1.B-48, IV-D.4-1.B-1 - IV-D.4-1.B-48, IV-E .4-1.B-1 - IV-E.4-1.B-48, IV-F.4-1.B-1 - IVF.4-1.B-48, IV-G.4-1 .B-1 - IV-G.4-1.B-48, IV-H.4-1.B-1 - IV-H.4-1.B-48, IV-I.4-1.B -1 - IV-I.4-1.B-48).

Table B

No. Q ^{3 R1 R2 R4} IN 1 COSNz SNz SNz H AT 2 SOSN ₂ SNz SNz SNz H AT 3 COCH2CH2CH3 SNz SNz n AT 4 CO (CH ₂ ) CH ₃ SNz SNz n AT 5 CO (CH ₂ ) ₄ CH ₃ SNz SNz n AT 6 CO (CH ₂ ) ₅ CH ₃ SNz SNz n AT 7 CO (CH ₂ ) ₆ CH SNz SNz n AT 8 SOSS13 SNz SNz n AT 9 COCH ₂ C1 SNz SNz n AT 10 COPh SNz SNz n AT 11 COCH2R11 SNz SNz n AT 12 COCH2P11-4-F SNz SNz n B-13 COCH( _CH3 )Ph SNz SNz n B-14 COCH(CH ₃ )-4-F SNz SNz n B-15 COCH(CH ₃ )-4-CH3 SNz SNz n B-16 COCH(CHz)-3-CH ₃ SNz SNz n B-17 COCH(CHz)-3-CH ₃ SNz SNz n B-18 _CF3 SNz SNz n B-19 chf ₂ SNz SNz n IN 20 CH2CH2OSH3 SNz SNz n AT 21 sn ₂ -s _b n ₅ SNz SNz n B-22 CH ₂ -C ₆ H ₄ -4-F SNz SNz n B-23 CH (CH ₃ ) -C ₆ H ₅ SNz SNz n B-24 CH(CH ₃ )-C ₆ H ₄ -4-F SNz SNz n B-25 COCH3 SNz SNz SNz B-26 COCH2CH3 SNz SNz SNz B-27 COCH2CH2CH3 SNz SNz SNz B-28 CO (CH ₂ ) CH ₃ SNz SNz SNz B-29 CO (CH ₂ ) ₄ CH ₃ SNz SNz SNz B-30 CO (CH ₂ ) ₅ CH ₃ SNz SNz SNz B-31 CO (CH ₂ ) _b CH ₃ SNz SNz SNz B-32 COCC1 ₃ SNz SNz SNz B-33 COCH ₂ C1 SNz SNz SNz B-34 COPh SNz SNz SNz B-35 _COCH2 Ph SNz SNz SNz B-36 _COCH2 Ph-4-F SNz SNz SNz

- 12 042940

B-37 COCH( _CH3 )Ph sn ₃ sn ₃ sn ₃ B-38 COCH(CH ₃ )-4-F sn ₃ sn ₃ sn ₃ B-39 COCH(CH ₃ )-4-CH ₃ sn ₃ sn ₃ sn ₃ B-40 COCH(CH ₃ )-3-CH ₃ sn ₃ sn ₃ sn ₃ B-41 COCH(CH ₃ )-3-CH ₃ sn ₃ sn ₃ sn ₃ B-42 _CF3 sn ₃ sn ₃ sn ₃ B-43 chf ₂ sn ₃ sn ₃ sn ₃ B-44 CH ₂ CH ₂ DOS ₃ sn ₃ sn ₃ sn ₃ B-45 sn ₂ -s ₆ n ₅ sn ₃ sn ₃ sn ₃ B-46 CH ₂ -C ₆ H ₄ -4-F sn ₃ sn ₃ sn ₃ B-47 CH (CH ₃ ) -C ₆ H ₅ sn ₃ sn ₃ sn ₃ B-48 CH(CH ₃ )-C ₆ H ₄ -4-F sn ₃ sn ₃ sn ₃

Compounds I and compositions according to the invention are suitably suitable as fungicides. They are distinguished by excellent efficacy against a wide range of phytopathogenic fungi, including soil fungi, which, in particular, come from the classes of Plasmodiophoromycetes, Peronosporomycetes (syn. oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. imperfect fungi). Some are systemically effective and can be used for crop protection as foliar fungicides, seed dressing fungicides and soil fungicides. In addition, they are suitable for the control of harmful fungi, which, among other things, are found in wood or plant roots.

Compounds I and compositions according to the invention are of particular value in controlling a variety of pathogenic fungi on various crops such as cereals, for example wheat, rye, barley, triticale, oats or rice; beets, such as sugar or fodder beets; fruits such as pome, stone fruit or berry fruits such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; legumes such as lentils, peas, alfalfa or soybeans; oil plants such as rapeseed, mustard, olives, sunflowers, coconut, cocoa beans, castor beans, oil palms, peanuts or soybeans; cucurbits such as pumpkin, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetable plants such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, squash or capsicum; bay plants such as avocado, cinnamon or camphor; energy and raw material plants such as corn, soybean, rapeseed, sugarcane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapes (table and wine grapes); hop; turf; sweet grass (also called stevia); rubber plants or ornamental and woodland plants such as flowers, shrubs, deciduous trees or evergreens such as conifers; and on plant propagation material, such as seeds, and the harvested crop of these plants.

Preferably, the compounds I and their compositions, respectively, are used to control a variety of fungi in field crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruit; grapes; ornamental plants; or vegetable crops such as cucumbers, tomatoes, beans or pumpkins.

The term plant propagation material should be understood to mean all generative parts of a plant such as seeds and vegetative plant parts such as cuttings and tubers (eg potatoes) that can be used to propagate a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, seedlings and other parts of plants, including seedlings and young plants that are transplanted after germination or emergence from the ground. These young plants can also be protected before replanting by full or partial treatment by dipping or watering.

Preferably, the treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used to control a variety of fungi on crops such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

The term crop plants also covers those plants that have been modified by breeding, mutagenesis, or genetic engineering techniques, including, but not limited to, biotech agricultural products on the market or in development (see http://cera-gmc.org/, see there is a database of GM crops). Genetically modified plants are plants whose genetic material has been altered in a manner using recombinant DNA technology that, under natural conditions, cannot readily be obtained by cross-breeding, mutation or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, post-translational modifications of protein(s), oligopeptides, or polypeptides, for example, by glycosylation or polymer additions such as prenylated, acetylated, or farnesylated moieties or PEG moieties.

Also covered are plants that have been modified by breeding, mutagenesis, or genetic engineering, for example, that have been rendered tolerant to the use of particular classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylurea or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; inhibitors of protoporphyrinogen-GC oxidase; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACC) inhibitors; or oxynyl herbicides (ie, bromoxynil or ioxynil) as a result of conventional breeding or genetic engineering techniques. In addition, plants have been produced that, through various genetic modifications, are resistant to many classes of herbicides, for example, resistant to glyphosate and glufosinate, or to glyphosate and a herbicide from another class, such as ALS inhibitors, HPPD inhibitors, auxin herbicides and ACC inhibitors. . These herbicide tolerance technologies are described in, for example, Pest Managem. sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sc. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and in the references cited there. Through conventional breeding (mutagenesis) techniques, some crop plants have acquired herbicide tolerance, such as Clearfield® rape (Canola, BASF SE, Germany), which is tolerant to imidazolinones, such as imazamox, or ExpressSun® sunflower (DuPont, USA), which possesses tolerance to sulfonylurea, for example, to tribenuron. Genetic engineering techniques have been used to make crops such as soybeans, cotton, corn, beets and canola tolerant to herbicides such as glyphosate and glufosinate, some of which are in development or are commercially available under the trade names RoudupReady® (tolerant glyphosate, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and Liberty Link® (glufosinate tolerant, Bayer CropScience, Germany).

Also covered are plants which, using recombinant DNA techniques, are capable of synthesizing one or more insecticidal proteins, in particular those known from the bacterial genus Bacillus, in particular Bacillus thuringiensis, such as 5-endotoxins, e.g. CryIA(b), CryIA(c ), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIPs), eg VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacterial colonized nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; animal-produced toxins such as scorpion toxins, spider toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi such as streptomycete toxins; plant lectins such as pea or barley lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosomin-activating proteins (RIPs) such as ricin, maize RIBs, abrin, luffin, saporin, or bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase, cholesterol oxidase, ecdysone or HMG-CoA reductase inhibitors; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbensynthase, bibenzyl synthase, chitinases and glucanases. In the context of the present invention, these insecticidal proteins or toxins are to be explicitly understood as also pretoxins, fusion proteins, truncated or otherwise modified proteins. Fusion proteins are distinguished by a novel combination of protein domains (see, for example, WO 02/015701). Other examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073. Methods for obtaining such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the above publications. These insecticidal proteins, found in genetically modified plants, confer tolerance to animal pests from all taxonomic classes of arthropods, in particular beetles (Coeloptera), dipterans (Diptera), and lepidoptera (Lepidoptera), and nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above publications, and some of them are commercially available, such as YieldGard® (corn varieties that produce Cry1Ab toxin), YieldGard® Plus (corn varieties, which produce Cry1Ab and Cry3Bb1 toxins), Starlink® (maize varieties that produce Oy9c toxin), Herculex® RW (maize varieties that produce Cry34Ab1, Cry35Ab1 toxins and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties that produce Cry1Ac toxin), Bollgard® I (cotton varieties that produce Cry1Ac toxin),

- 14 042940

Bollgard® II (cotton varieties that produce CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton varieties that produce VIP toxin); NewLeaf® (potato varieties that produce Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (maize varieties that produce Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties that produce a modified version of the Oy3A toxin, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (maize varieties that produce the C33A toxin), IPC 531 from Monsanto Europe S.A.,

Belgium (cotton varieties that produce a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the Cry1F toxin and the PAT enzyme).

Also covered are plants that, using recombinant DNA technologies, are capable of synthesizing one or more proteins that cause increased resistance or tolerance of such plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called pathogenesis-dependent proteins (PR proteins, see e.g. EP-A 392225), plant disease resistance genes (e.g. potato varieties that express resistance genes active against Phytophthora infestans, bred from the Mexican wild potato Solarium bulbocastaniim) or T4-lysozyme (e.g. potato varieties that are able to synthesize these proteins with increased resistance to bacteria such as Erwinia amylvord). Methods for obtaining such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications cited above.

In addition, also covered are plants that, through the use of recombinant DNA technologies, are capable of synthesizing one or more proteins to improve productivity (e.g., biomass production, grain yield, starch content, oil content, or protein content), tolerance to drought, salinity, or other growth-limiting environmental factors or the tolerance of such plants to animal pests and fungal, bacterial and viral pathogens.

In addition, plants are also covered which, through the use of recombinant DNA technologies, contain a modified amount of substances contained or new substances, in particular for improving the nutrition of humans and animals, for example, oilseeds that produce healthy long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera® rapeseed, DOW Agro Sciences, Canada).

In addition, plants are also covered which, thanks to the use of recombinant DNA technologies, contain a modified amount of substances contained or new substances, in particular to improve the production of raw material, for example, potatoes that produce increased amounts of amylopectin (for example, potatoes Amflora®, BASF SE, Germany).

Compounds I and their compositions, respectively, are particularly suitable for combating the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (eg A. candida) and sunflowers (eg A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e.g. A. solani or A. alternata), tomatoes ( eg A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris spp. and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. corn leaf spot (D. maydis) or helminthosporium leaf blight (B. zeicola) on corn, e.g. helminthosporium root rot (B. sorokiniana) on cereals and e.g. B. oryzae on rice and sod; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (eg wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (eg strawberries), vegetables (eg lettuce, carrots, celery and cabbage), rapeseed, flowers, vines, woodland plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis spp. (syn. Ophiostoma) (rot or wilt) on deciduous and evergreen trees, eg C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spot) on corn (e.g. gray leaf spot: C. zeae-maydis), rice, sugar beets (e.g. C. beticola), sugarcane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (eg C. fulvum: leaf mold) and cereals, eg C. herbarum (olive mold) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus spp. (anamorph: Helminthosporium from Bipolaris) (leaf spot) on corn (C. carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana) and rice (e.g. C. miyabeanus, anamorph: H. oryzae) ] Colletotrichum spp. (teleomorph: Glomerella) (anthracnose) on cotton (e.g. C. gossypii), corn (e.g. C. graminicola: anthracnose stem rot), berries, potatoes (e.g. C. coccodes: anthracnose of potatoes and tomatoes), beans (eg C. lindemuthianum) and soybeans (eg C. truncatum or C.

- 15 042940 gloeosporioides); Corticium spp., eg C. sasakii (stem and sheath blight) on rice; Corynespora cassiicola (black spot) on soybeans and ornamental plants; Cycloconium spp., eg C. oleaginum on olive trees; Cylindrocarpon spp. (eg necrosis of fruit trees or vines, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (eg C. liriodendri, teleomorph: Neonectria liriodendri: blackleg disease) and ornamental plants; Dematophora necatrix (teleomorph: Rosellinia) (root and stem rot) on soybeans; Diaporthe spp., eg D. phaseolorum (blackleg) on soybeans; Drechslera spp. (syn. Helminthosporium, teleomorph: Pyrenophora) on corn, cereals such as barley (eg D. teres, net spot) and wheat (eg D. triticirepentis: pyrenophora), rice and turf; Esca on grapes caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), berries (E. veneta: anthracnose) and grapes (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum species (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (eg E. pisi) such as cucurbits (eg E. cichoracearum), cabbage, rapeseed (eg E. cruciferarum); Eutypa lata (eutyposis, cancer or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental shrubs; Exserohilum spp. (syn. Helminthosporium) on corn (eg E. turcicum); Fusarium spp. (teleomorph: Gibberella) (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or Fusarium) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani (a wisteria species, now syn. F. virguliforme) and F. tucumaniae and F. brasiliense, each causing sudden death syndrome, on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (damping off) on cereals (eg wheat or barley) and corn; Gibberella spp. on cereals (eg G. zeae) and rice (eg G. fujikuroi: Bakanae disease); Glomerella cingulata on grapes, pome fruits and other plants and G. gossypii on cotton; grain coloring complex on rice; Guignardia bidwellii (black rot) on grapes; Gymnosporangium spp. on rosaceae and junipers, eg G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., eg H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on grapes; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (eg wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monrlinia spp., eg M. laxa, M. fructicola and M. fructigena (dryness of flowers and leaf tips, brown rot) on stone fruit and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, berries and peanuts, such as, for example, M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (Black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae), rapeseed (e.g. P. parasitica), bulbs (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsorapachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp., for example on grapes (eg P. tracheiphila and P. tetraspora) and soybeans (eg P. gregata: stem rot); Phoma lingam (root and stem rot) on rapeseed and cabbage and P. betae (root rot, black spot and blackleg) on sugar beets; Phomopsis spp. on sunflowers, vines (eg P. viticola: black spot) and soybeans (eg stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem rot) on various plants such as paprika and cucurbits (eg P. capsici), soybeans (eg P. megasperma, syn. P. sojae), potatoes and tomatoes (eg P. infestans: late blight) and hardwoods (eg P. ramorum: sudden oak death); Plasmodiophora brassicae (Kila) on cabbage, rapeseed, radish and other plants; Plasmopara spp., eg P. viticola (vine downy mildew) on grapes and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceae, hops, pome fruits and berries, eg P. leucotricha on apple trees; Polymyxa spp., for example on cereals such as barley and wheat (P. graminis) and sugar beet (P. betae), and the resulting viral diseases; Pseudocercosporella herpotrichoides (eye spot, teleomorph: Tapesia yallundae) on cereals such as wheat or barley; Pseudoperonospora (downy mildew) on various plants, eg P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (vine leaf rubella, anamorph: Phialophora) on grapes; Puccinia spp. (rust) on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (striation or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals such as, for example, wheat, barley or rye, P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) triticirepentis (pyrenophorosis) on wheat or P. teres (net spot) on barley; Pyricularia spp., eg P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium species (black leg) on turf, rice, corn,

- 16 042940 wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and other plants (eg P. ultimum or P. aphanidermatum); Ramularia spp., eg R. collocygni (ramularia black spot, physiological black spot) on barley and R. beticola on sugar beet; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rapeseed, tomatoes, sugar beets, vegetables and other plants, e.g. R. solani (root and stem rot) on soybeans, R. solani (stem and sheath rhizoctoniosis) on rice or R. cerealis (rhizoctoniosis) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbages, grapes and tomatoes; Rhynchosporium secalis (Rhynchosporus scorch) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white rot) on vegetables and field crops such as rapeseed, sunflowers (eg S. sclerotiorum) and soybeans (eg S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, eg S. glycines (brown spot) on soybeans, S. tritici (septoria spot) on wheat, and S. (syn. Stagonospora) nodorum (stagonospora spot) on cereals; Uncinula necator (syn. Erysiphe) (powdery mildew, anamorph: Oidium tuckeri) on grapes; Setospaeria spp. (leaf spot) on corn (eg S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (eg S. reiliana: smut smut), sorghum and sugarcane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and resulting viral diseases; Stagonospora spp. on cereals, eg S. nodorum (stagonospore spot, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato cancer); Taphrina species, eg T. deformans (leaf curl) on peaches and T. pruni (plum pockets) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, eg T. basicola (syn. Chalara elegans); Tilletia spp. (bunt or stink smut) on cereals, such as, for example, T. tritici (syn. T. caries, bunt of wheat) and T. controversa (dwarf smut) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., eg U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables such as beans (eg U. appendiculatus, syn. U. phaseoli) and sugar beets (eg U. betae); Ustilago spp. (loose smut) on cereals (eg U. nuda and U. avaenae), corn (eg U. maydis: blister smut) and sugar cane; Venturia spp. (scab) on apple trees (eg V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants such as fruit and ornamental plants, vines, berries, vegetables and field crops, eg V. dahliae on strawberries, rapeseed, potatoes and tomatoes.

Compounds I and their compositions, respectively, are also suitable for the control of harmful fungi in the protection of stored products or harvested products and in the protection of materials.

The term material protection is to be understood as meaning the protection of technical and inanimate materials such as, for example, adhesives, adhesives, wood, paper and cardboard, textiles, leather, dye dispersions, synthetic materials, cutting fluids, fibers and fabrics, from damage and destruction by harmful microorganisms such as fungi and bacteria. When protecting wood and other materials, the following harmful fungi are taken into account in particular: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp. zygomycetes such as Mucor spp., and in addition, the following yeast fungi deserve attention in protecting stored products and harvested crops: Candida spp. and Saccharomyces cerevisae.

The treatment method according to the invention can also be applied in the field of protecting stored products or harvested crops from attack by fungi and microorganisms. For the purposes of the present invention, stored products are to be understood as natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is required. Stored products that originate from crops, such as plants or parts thereof, such as stems, leaves, tubers, seeds, fruits or grains, may be protected in a freshly harvested state or in a processed form such as pre-dried, moistened, ground, milled, pressed or fried, which process is also known as post-harvest processing. Also included in the definition of stored products is timber, both in the form of raw timber, such as construction timber, power poles and fences, and in the form of finished products, such as furniture or objects made of wood. Stored animal products are hides, leather, fur, wool, and the like. Combinations in accordance with the present invention can prevent undesirable effects such as rotting, discoloration or mold formation. Preferably, stored products should be understood as natural substances of plant origin and their processed forms,

- 17 042940 more preferably fruits and their processed forms, such as pome fruits, stone fruits, berries and citrus fruit crops and their processed forms.

Compounds I and their compositions, respectively, can be used to improve the viability of the plant. The invention also relates to a method for improving the viability of a plant by treating the plant, its propagation material and/or the place where the plant grows or is to grow, with an effective amount of compounds I and their compositions, respectively.

The term plant viability should be understood as the state of the plant and/or its products, which is determined by various indicators alone or in combination with each other, such as, for example, yield (for example, increased biomass and/or increased content of valuable components), plant vigor (for example, , increased plant growth and/or greener leaves (greening effect), quality (e.g. increased content or composition of certain components) and tolerance to abiotic and/or biotic stress The above indicators for plant health status may be interdependent or may result from each other. from friend.

The compounds of formula I may be present in various crystalline modifications, the biological activity of which may differ. They are likewise the subject of the present invention.

The compounds I are applied as such or in the form of compositions by treating harmful fungi or plants to be protected against fungal attack, plant propagation materials such as seeds, soils, surfaces, materials or rooms with a fungicidally effective amount of active substances. Application can take place both before and after fungal infection of plants, plant propagation materials such as seeds, soils, surfaces, materials or rooms.

Plant propagation materials can be treated with the compounds I as such, or with a composition containing at least one compound I, prophylactically, either during or before planting or transplanting.

The invention also relates to agrochemical compositions containing an adjuvant and at least one compound I in accordance with the invention.

The agrochemical composition contains a fungicidally effective amount of compound I. The term effective amount means an amount of the composition or compounds I which is sufficient to control harmful fungi on crop plants or to protect materials and which does not result in significant damage to the treated plants. This amount can vary over a wide range and depends on many factors such as the species of fungus being controlled, the crop or material being treated, climatic conditions and the specific compound I used.

The compounds I, their N-oxides and salts can be formulated into conventional types of agrochemical compositions, for example solutions, emulsions, suspensions, fine powders, powders, pastes, granules, compacted products, capsules and mixtures thereof. Examples of formulation types are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg CS, ZC), pastes, lozenges, wetted powders or fine powders (e.g. WP, SP, WS, DP, DS), compressed products (e.g. BR, TV, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal products ( eg LN) as well as gel formulations for treating plant propagation material such as seeds (eg GF). These and other composition types are defined in the Catalog of pesticide formulation types and international coding system, Technical Monograph No. 2, ^6th ed., May 2008, CropLife International.

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, Agrow Reports DS243, T&F Informa, London, 2005.

Suitable excipients are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration agents, protective colloids, adhesion promoters, thickeners, wetting agents, repellants, attractants, eating stimulants, compatibilizers, bactericides, antifreezes, antifoams, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions such as kerosene, diesel oil; oils of vegetable or animal origin, aliphatic, cyclic or aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, eg ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, eg lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acid; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and their mixtures.

- 18 042940

Suitable solid carriers or fillers are mineral earths, for example silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose starch; fertilizers, eg ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; vegetable products such as cereal flour, tree bark flour, wood flour, nutshell flour and mixtures thereof.

Suitable surfactants are surface active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are given in McCutcheon's Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International ed. or North American ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts - sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalenes sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalenes and alkylnaphthalenes sulfonates, sulfosuccines. ates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

Suitable non-ionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 eq. the corresponding reagent. For alkoxylation, ethylene oxide and/or propylene oxide, preferably ethylene oxide, can be used. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose-glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or A-B-C type block polymers comprising alkanol, 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 polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds which in themselves have very little or even no pesticidal activity and which improve the biological effectiveness of the compounds I on the target. Examples are surfactants, mineral or vegetable oils and other adjuvants. For more examples, see Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

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

Suitable antifreezes are ethylene glycol, propylene glycol, urea and glycerin.

Suitable antifoam agents are silicones, long chain alcohols and salts of fatty acids.

Suitable dyes (eg red, blue or green) are pigments with low water solubility and water soluble dyes. Examples are inorganic dyes (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg alizarin, azo and phthalocyanine dyes).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.

Examples of types of compositions and their preparation are:

I) Water-soluble concentrates (SL, LS) 10-60 wt.% of compound I and 5-15 wt.% of a wetting agent (for example, alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (for example, alcohols), taken in an amount up to 100 wt.%. When diluted with water, the active substance dissolves.

II) Dispersible concentrates (DC) 5-25% by weight of compound I and 1-10% by weight of a dispersant (eg polyvinylpyrrolidone) are dissolved in an organic solvent (eg cyclohexanone) up to 100% by weight. Dilution with water gives a dispersion.

III) Emulsifiable concentrates (EC) 15-70 wt.% compound I and 5-10 wt.% emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (for example, an aromatic hydrocarbon), taken in an amount up to 100 wt.%. When diluted with water, an emulsion is obtained.

IV) Emulsions (EW, EO, ES) 5-40 wt.% of compound I and 1-10 wt.% of emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt.% of a water-insoluble organic solvent ( such as an aromatic hydrocarbon). This mixture is added by means of an emulsifying device to water, taken in an amount up to 100 wt.%, and brought to a homogeneous emulsion. When diluted with water, an emulsion is obtained.

V) Suspensions (SC, OD, FS)

In a ball mill with a stirrer, 20-60 wt.% of compound I is ground to a fine suspension of the active substance with the addition of 2-10 wt.% of dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt.% of a thickener (for example, xanthan gum) and water, taken in an amount up to 100 wt.%. When diluted with water, a stable suspension of the active substance is formed. For an FS type composition, up to 40% by weight of a binder (eg polyvinyl alcohol) is added.

VI) Water-dispersible and water-soluble granules (WG, SG) 50-80 wt.% of compound I is finely ground by adding dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), taken in an amount up to 100 wt.%, and through technical devices (for example, extrusion device, spray tower, fluidized bed) receive water-dispersible or water-soluble granules. When diluted with water, a stable dispersion or solution of the active substance is formed.

VII) Water-dispersible and water-soluble powders (WP, SP, WS) % wetting agents (for example, alcohol ethoxylate) and a solid carrier (for example, silica gel), taken in an amount up to 100 wt.%. When diluted with water, a stable dispersion or solution of the active substance is formed.

VIII) Gel (GW, GF)

In a ball mill with a stirrer, 5-25 wt.% of compound I is ground to a fine suspension of the active substance with the addition of 3-10 wt.% of dispersants (for example, sodium lignosulfonate), 1-5 wt.% of a thickener (for example, carboxymethylcellulose) and water, taken in an amount up to 100 wt.%. When diluted with water, a stable suspension of the active substance is formed.

IX) Microemulsion (ME) 5-20 wt.% of compound I is added to 5-30 wt.% of a mixture of organic solvents (for example, fatty acid dimethylamide and cyclohexanone), 10-25 wt.% of a mixture of surfactants (for example, ethoxylate alcohol and arylphenol ethoxylate) and water taken in an amount up to 100 wt.%. This mixture is stirred for 1 hour, spontaneously producing a thermodynamically stable microemulsion.

X) Microcapsules (CS)

An oil phase containing 5-50 wt.% compound I, 0-40 wt.% water-insoluble organic solvent (for example, aromatic hydrocarbon), 2-15 wt.% acrylic monomers (for example, methyl methacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50% by weight of a compound I according to the invention, 0-40% by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethane-4,4'- diisocyanate), dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers up to 1-10 wt.% refers to the total CS composition.

XI) Fine powders (DP, DS) 1-10 wt.% of compound I are finely ground and thoroughly mixed with a solid carrier (for example, finely dispersed kaolin), taken in an amount of up to 100 wt.%.

XII) Granules (GR, FG) 0.5-30 wt.% of compound I are finely ground and associated with a solid carrier (eg silicate), taken in an amount up to 100 wt.%. Granulation is achieved with the help of ex-

- 20 042940 trusion, spray drying or fluid bed.

XIII) Ultra-Low Volume Liquids (UL) 1-50% by weight of Compound I is dissolved in an organic solvent (eg aromatic hydrocarbon) up to 100% by weight.

Composition types I) to XIII) may optionally contain other adjuvants, for example 0.1-1 wt.% bactericides, 5-15 wt.% antifreezes, 0.1-1 wt.% antifoams and 0.1-1 wt. .% dyes.

As a rule, agrochemical compositions contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, more preferably between 1 and 70% and in particular between 10 and 60% by weight of the active substance. The active substances are used in a purity of 90 to 100%, preferably 95 to 100% (according to NMR spectrum).

For the treatment of plant propagation materials, in particular seeds, seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water-dispersible slurry treatment powders (WS ), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF). The compositions in question, after two to tenfold dilution, give concentrations of the active substance in ready-to-use preparations from 0.01 to 60 wt.%, preferably from 0.1 to 40%. Application can be carried out before or during sowing. Methods for applying compounds I and compositions thereof, respectively, to plant propagation material, especially seeds, include dressing, coating, panning, dusting, and soaking, as well as furrow application methods. Preferably, Compound I or compositions thereof, respectively, is applied to the plant propagation material in a manner that does not induce germination, for example by dressing, panning, coating and dusting the seeds.

When used for plant protection, the amounts of active substances used, depending on the type of effect desired, are from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and , in particular from 0.1 to 0.75 kg per ha.

When treating plant propagation materials such as seeds, for example by dusting, coating or impregnating seeds, the active substance is usually required in an amount of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g, per 100 kg of plant propagation material (preferably seeds).

When used in the protection of materials or stored products, the amount of active substance used depends on the type of application and on the desired effect. Amounts commonly used in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of active substance per cubic meter of treated material.

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and additional pesticides (eg, herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) can be added to the active substances or compositions containing them as a premix, or, if necessary, only immediately before use (tank mix). Such agents can be mixed into the compositions according to the invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.

A pesticide is generally a chemical or biological agent (such as a pesticidal active, compound, composition, virus, bacterium, antimicrobial, or disinfectant) that repels, incapacitates, kills, or otherwise counteracts pests. Target pests may include insects, plant pathogens, weeds, shellfish, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause harm, spread disease, or carry diseases. The term pesticide also includes plant growth regulators that alter the expected rate of growth, flowering, or reproduction of plants; defoliants, which cause the plant to drop leaves or other foliage, usually to facilitate harvesting; desiccants that dry out living tissues such as unwanted plant tops; plant activators that activate plant physiology to protect against certain pests; safeners, which reduce the undesirable herbicidal effect of pesticides on agricultural plants; and plant growth stimulants which affect plant physiology, for example, to increase plant growth, biomass, yield, or any other quality parameter of the crop plant to be harvested.

Biopesticides have been defined as a form of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds such as metabolites, proteins, or extracts from biological or other natural sources) (US Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides are divided into two main classes, microbial and biochemical pesticides:

(1) Microbial pesticides are composed of bacteria, fungi, or viruses (and often include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticides despite being multicellular.

- 21 042940 (2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively non-toxic to mammals.

The composition according to the invention is typically applied by the user from a pre-dosing device, a backpack sprayer, a spray tank, a spray aircraft or an irrigation system. Typically, the agrochemical composition is diluted with water, buffer and/or other adjuvants to the desired application concentration, and thus a ready-to-use spray liquid or agrochemical composition according to the invention is obtained. Typically, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid per hectare of agricultural land are used.

In accordance with one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank or any other type of vessel used for application (for example, seed treatment drums). , seed coating equipment, knapsack sprayer) and, in addition, other auxiliaries can be added if necessary.

If live micro-organisms such as microbial pesticides from groups L1), L3) and L5) are part of such a kit, it should be taken into account that the choice and amounts of components (e.g. chemical pesticides) and other adjuvants should not affect the viability of microbial pesticides. in user-mixed compositions. Particularly for bactericides and solvents, compatibility with the respective microbial pesticide must be taken into account.

Therefore, one embodiment according to the invention is a kit for the preparation of a usable pesticidal composition, the kit comprises a) a composition containing component I as defined herein and at least one excipient; and b) a composition containing component 2) as defined herein and at least one excipient; and optionally c) a composition comprising at least one excipient and optionally another active ingredient 3) as defined herein.

Mixing compounds I or compositions containing them in the form of use as fungicides with other fungicides in many cases leads to an extension of the spectrum of fungicidal activity obtained or to the prevention of the development of resistance to fungicides. In addition, in many cases, synergistic effects are obtained.

The following list of pesticides II (e.g., pesticide actives and biopesticides) with which Compounds I may be used is intended to illustrate, but not limit, possible combinations:

A) Respiratory inhibitors inhibitors of complex III at the Qo site: azoxystrobin (A.1.1), cumethoxystrobin (A.1.2), cumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), phenaminestrobin (A. 1.6), phenoxystrobin/fluphenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), methominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)- 1-methylallylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methylacetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodinecarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21), methyl N-[2-[(1,4-dimethyl-5-phenylpyrazol-3-yl)oxylmethyl]phenyl]-N-methoxycarbamate (A.1.22), 1-[3-chloro-2-[[1-( 4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyltetrazol-5-one (A.1.23), 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazole -3-yl]oxymethyl]phenyl]-4-methyltetrazol-5-one (A.1.24), 1[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]- 4-methyltetrazol-5-one (A.1.25), 1-[2-[[1-(4chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluorophenyl]-4-methyltetrazol-5-one (A.1.26 ), 1-[2-[[1-(2,4-Dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluorophenyl]-4-methyltetrazol-5-one (A.1.27), 1-[3- cyclopropyl 2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyltetrazol-5-one (A.1.30), 1-[3(difluoromethoxy)-2-[ [2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyltetrazol-5-one (A.1.31), 1-methyl-4-[3-methyl-2-[ [2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one (A.1.32), (Z,2E)-5-[ 1 -(2,4-dichlorophenyl )pyrazol-3-yl]-hydroxy-2-methoxyimino-K,3-dimethylpent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl ]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunji (A.1.37), 2-(ortho-((2,5dimethylphenyloxymethylene) methyl ester) phenyl)-3-methoxyacrylic acid (A. 1.38);

complex III inhibitors at the Qi site: cyazofamide (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3), phenpicoxamide (A.2.4);

complex II inhibitors: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalide (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A. 3.7), flutolanil (A.3.8), fluxapiroxad

- 22 042940 (A.3.9), furametpyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxine (A.3.14), penflufen (A.3.15) , penthiopyrad (A.3.16), pidiflumethofen (A.3.17), pyraziflumide (A.3.18), sedaxan (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), 3-(difluoromethyl)-1 -methyl-N(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4 -yl)pyrazol-4-carboxamide (A.3.23), 1,3-dimethyl-N-(1,1,3-trimethylindαn-4-yl)pyrαzol-4carboxamide (A.3.24), 3-(trifluoromethyl)- 1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1,3,5-trimethyl-N-(1,1,3-trimethylindan -4-yl)pyrazole-4-carboxamide (A.3.26), 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A .3.27), 3-(difluoromethyl)N-(7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide (A.3.28), N[(5-chloro-2 -isopropylphenyl)methyl]-N-cyclopropyl-5-fluoro-1,3-dimethylpyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2[(5-cyano-2-methylphenoxy)methyl] phenyl]-3-methoxyprop-2-enoate (A.3.30), N[(5-chloro-2-isopropylphenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4- carboxamide (A.3.31), 2(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)-pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R) 1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridin-3 - carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N -(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-pronilindan-4 -yl]niridin-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide (A.3.38), 2- (difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethylindan-4-yl]pyridin-3-carboxamide (A.3.39);

other respiratory inhibitors: diflumetorim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimsone (A.4.7); organometallic compounds: salts of fentin, for example fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); amethoctradine (A.4.11); silthiopham (A.4.12);

B) Sterol biosynthesis inhibitors (IHD fungicides) C14 demethylase inhibitors: triazoles: aconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), fluzilazole (B.1.11), flutriafol (B.1.12) , hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2(chloromethyl)-2-methyl-5-(p-tolylmethyl )-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforin (B.1.51), [3-(4-chloro-2-fluorophenyl)5-(2,4-difluorophenyl)isoxazol- 4-yl]-(3-pyridyl)methanol (B.1.52);

delta-14 reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidine (B.2.6) , piperalin (B.2.7), spiroxamine (B.2.8);

3-ketoreductase inhibitors: fenhexamide (B.3.1);

other inhibitors of sterol biosynthesis: chlorfenomysole (B.4.1);

C) Nucleic acid synthesis inhibitors phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), chiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2- (p-tolylmethoxy)pyrimidine-4amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidine-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidine-4 -amine (C.2.8);

D) Inhibitors of cell division and cytoskeleton tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chlorine -4-(2,6-difluorophenyl)-6methyl-5-phenylpyridazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7 ), Nethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy ]-2-methylsulfanilacetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3- ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxyacetamide (D.1.11), 2[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N- propylbutanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propylacetamide (D.1.13), 2-[(3-ethynyl-8-methyl -6-quinolyl)oxy]-2-methylsulfanyl-N-propylacetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanylacetamide ( D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine (D.1.16);

other cell division inhibitors: dietofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriophenone (D .2.7);

E) Inhibitors of amino acid and protein synthesis Inhibitors of methionine synthesis: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);

protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasu-hamycin hydrochloride hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E .2.6);

F) Signal transduction inhibitors MAP kinase/histidine kinase inhibitors: fluorimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozoline (F.1.4), fludioxonil (F.1.5);

G-protein inhibitors: quinoxifene (F.2.1);

G) Inhibitors of lipid and membrane synthesis Inhibitors of phospholipid biosynthesis: edifenphos (G.1.1), iprobenphos (G. 1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);

lipid peroxidation inhibitors: diclorane (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclophosmethyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiasol (G .2.7);

inhibitors of phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamide (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

compounds affecting cell membrane permeability and fatty acids: propamocarb (G.4.1);

oxysterol-binding protein inhibitors: oxathiapiproline (G.5.1), 2-{3-[2-(1-{[3,5bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1, 3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1-{[3,5-bis( difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3- chlorophenyl methanesulfonate (G.5.3), 4-[1[2-[3-(difluoromethyl)-5-methylpyrazol-1-yl]acetyl]-4-piperidyl]-M-tetralin-1-ylpyridine-2-carboxamide ( G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-M-tetralin-1-ylpyridine2-carboxamide (G.5.5) , 4-[1-[2-[3-(Difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-Mtetralin-1-ylpyridin-2-carboxamide (G.5.6), 4-[1-[2-[5-Cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.7), 4 -[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.8), 4- [ 1-[2-[5(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.9), 4- [1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1ylpyridine-2-carboxamide (G.5.10), (4-[1 - [2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.11);

H) Multi-site inhibitors inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);

thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metham (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H .2.7), cineb (H.2.8), cyram (H.2.9);

organochlorines: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophene (H.3.7) ), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);

guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guasatin (H.4.4), guasatin acetate (H.4.5), iminoctadine (H.4.6), iminoctadine triacetate (H.4.7), iminoctadintris(albesilate) (H.4.8), dithianone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5 ,6-c']dipyrrole 1,3,5,7(2H,6H)-tetraone (H.4.10);

I) Cell wall synthesis inhibitors glucan synthesis inhibitors: validamycin (1.1.1), polyoxin B (1.1.2);

melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamide (1.2.3), dicyclomet (1.2.4), phenoxanil (1.2.5); J) Plant protection inducers acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isothianil (J.1.3), thiadinyl (J.1.4), prohexadione-calcium (J.1.5); phosphonates: phosethyl (J.1.6), phosethyl aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate ( J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5carboxamide (J.1.10);

K) Unknown mechanism of action bronopol (K.1.1), quinomethionate (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocimet (K .1.7), diclomesin (K.1.8), diphenzoquat (K.1.9), diphenzoquat methyl sulfate (K.1.10), diphenylamine (K.1.11), fenitropan (K.1.12), phenpyrazamine (K.1.13), flumetover ( K.1.14), flusulfamide (K.1.15), fluthianil (K.1.16), harpin (K.1.17), metasulfocarb (K.1.18), nitrapyrine (K.1.19), nitrotalisopropyl (K.1.20), tolprocarb (K .1.21), oxin copper (K.1.22), proquinazid (K.1.23), tebufloquine (K.1.24), teclophthalam (K.1.25), triazoxide (K.1.26), N'-(4-(4chloro- 3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine (K.1.27), K.1.28), N-[4-[[3-[(4chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methylformamidine (K.1.30), N'-[5- 6pom-6-[1(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine (K.1.31), N'-[5-6pom-6-(4isopropylcyclohexoxy )-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidine (K.1.32), N'-[5-6pom-2methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl -N-methylformamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine (K. 1.34), N'-(5-difluoromethyl-2methyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine (K. 1.35), 2-(4-chlorophenyl)-N- 24 042940

[4-(3,4-dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide (K.1.36), 3-[5-(4-chlorophenyl)-2,3dimethylisoxazolidin-3-yl]pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidine- 2-yl)-2-methyl-1H-benzoimidazole (K. 1.39), ethyl (Z)-3-amino-2-cyano-3-phenylprop-2-enoate (K.1.40), picarbutrazox (K.1.41) , pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl N-[ 6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), 2-[2-[(7,8-difluoro- 2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol (K.1.44), 2-[2-fluoro6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl ]propan-2-ol (K.1.45), quinofumeline (K.1.47), 9-fluoro-2,2dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine (K.1.49), 2- (6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlobentiazox (K.1.52 ), N'-(2,5dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (K. 1.53);

L) Biopesticides

L1) Microbial pesticides with fungicidal, bactericidal, virucidal and/or plant protection activating activity: Ampelomyces quisqualis, Aspergillus Jlavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium OKCUsporum, Clonostachys rosea f. catenulate (also called Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowiafructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis , Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and/or plant protection activating activity: harpin protein, Reynoutria sachalinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and/or nematocidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, subspecies B. thuringiensis aizawai, B. t. subspecies israelensis, B. t. subspecies galleriae, B. t. subspecies kurstaki, B. t. subspecies Tenebrionis, Beauveria Bassiana, B. Brongniartii, Types Burkholderia, Chromobacterium Subtsugae, Cydia Pomonella Granuloviru (CPGV), Cryptophia leucotreta granulovirus (Crelegv), Types Flavobacterium, Helicoverpa Armigera virus of nuclear polyedrosis (Hearnpv), Helicoverpa ZEA Nuclear Polyerosis virus (HZNPV) , Helicoverpa zea separate nuclear polyhedrosis virus (HzSNPV) capsid, Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nuclear polyhedrosis virus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus;

L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromone and/or nematocidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2 ,4-ethyldecadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl 1-butanol, methyl eugenol, methyl jasmonate, (E ,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, R1-octen -3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, 2-7-tetradecen-2-one , Z-9-tetradecen-1-yl acetate, Z-11-tetradecenal, Z-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, margosa seed oil, quillaya extract;

L5) Microbial pesticides with plant stress reducing, plant growth regulating, plant growth stimulating and/or plant yield increasing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium species, Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium meliloti;

M) Growth regulators: abscisic acid (M.1.1), amidochlor, ancimidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminoside, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetraline , flurprimidol, flutiacet, forchlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid, maleic acid hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmone, ti diazuron , triapentenol, tributylphosphorothritioate, 2,3,5-triiodobenzoic acid, trinexapak-ethyl, and uniconazole;

N) Herbicides from classes N.1-N.15

N.1 lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxidim, cyhalofop, cyhalofop-butyl, diclofop, diclofop

-25 042940 Methyl, Fenoksaprop, Fenoksapsaprop-Etil, Fenoksaprop-R, Floksapsapsaprop-R-Etil, Flyuzifop, Flyuzifopbutil, Flyuzifop-R, Fluazifop-R-Butil, Galloxif, Galoxifop-Meadtil, Haloxifop-R, Haloxifop-Remethyl, Metamifop , pinoxaden, profoxidim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl -2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2Hpyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H) -on (CaS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)- dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl -2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6tetramethyl-2H -pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl] -3 -yl)-3,6-dihydro2,2,6,6-tetramethyl- 2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H -pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5 methyl ester -oxo-2Hpyran-3-ylcarbonic acid (CAS 1312337-51-1); methyl ester 4-(2',4'-dichloro-4cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6tetramethyl-5-oxo methyl ester -2H-pyran-3-ylcarbonic acid (CAS 1312340-83-2); 4(2',4'-dichloro-4-ethyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo methyl ester -2H-pyran-3-ylcarbonic acid (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazil, triallate and vernolate;

N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuronmethyl, chlorimuron, chlorimuronethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, etametsulfuron, etametsulfuron methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron methyl sodium, foramsulfuron, halosulfuron, halosulfuronmethyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuronmethyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuronmethyl, propirisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuronethyl, rimsulfuron, sulfometuron, sulfometuronmethyl, sulfosulfuron, thifensulfuron, thifensulfuronmethyl, triasulfuron, tribenuron, tribenuronmethyl, trifloxysulfuron, triflusulfuron, triflusulfuronmethyl, tritosulfuron, imazametabenz, imazametabenzmethyl, imazamox, imazapik, imazapyr, imazakhin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, methosulam, penoxulam, pyrimisulfan and pyroxulam; bispyribac, bispyribacsodium, pyribenzoxime, pyrifthalide, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobacsodium, 1-methylethyl ester 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino] benzoic acid (CAS 420138-41-6), 4-[[[2-[(4,6dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid propyl ester (CAS 420138-40-5), N-(4bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone, thiencarbazone methyl; triafamone;

N.3 photosynthesis inhibitors: amicarbazone; chlortriazine; ametrin, atrazine, chloridazone, cyanazine, desmetrin, dimethamethrin, hexazinon, metribuzin, prometon, prometrin, propazine, simazine, simetrin, terbumeton, terbutylazine, terbutrin, trietazine; chlorbromuron, chlortoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, metabenzthiazuron, methobenzuron, methoxuron, monolinuron, neburon, siduron, tebuthiuron, thiadiazuron, desmedifam, carbutylate, phenmedipham, phenmedifam- ethyl, bromophenoxime, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacyl, lenacil, terbacil, bentazon, sodium bentazone, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat dibromide, paraquat, paraquat dichloride, paraquat dimethyl sulfate;

N.4 protoporphyrinogen IX oxidase inhibitors: acifluorfen, acifluorfen sodium, azaphenidin, bencarbazone, benzfendison, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, cynidone-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumi clorac-pentyl , flumioxazine, fluoroglycofen, fluoroglycophen-ethyl, fluthiacet, flutiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiafen acyl, trifludimoxazine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy] acetate (CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl- 3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4 -trifluoromethyl-phenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2

- 26 042940 chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro3-oxo-4-(prop-2- inyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan2,4-dione (CAS 451484- 50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6yl)-4.5 ,6,7-tetrahydroisoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro3-oxo-4-prop-2-ynyl- 3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidin-2,4-dione (CAS 130411305-0), methyl (E)-4-[2-chloro-5 -[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3methoxybut-2-enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro -2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4);

N.5 bleaching herbicides: beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine (CAS 180608-33-7); benzobicyclone, benzofenap, bicyclopyrone, clomazone, fenhintrione, isoxaflutol, mesotrione, pyrasulfotol, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramesone; aclonifen, amitrol, flumeturon;

N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, glyphosattrimesium (sulfosate);

N.7 glutamine synthase inhibitors: bilanafos (bialafos), bilanafos sodium, glufosinate, glufosinate-P, glufosinate ammonium;

N.8 DHP synthase inhibitors: azulam;

N.9 mitosis inhibitors: benfluralin, butralin, dinitramine, etalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprofos, amiprofos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propizamide, tebutam; carbetamide, chlorprofam, flamprop, flampropisopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, profam;

N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-R, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor, tenylchlor, fluphenacet, mephenacet, diphenamide, naproanilide, napropamide, napropamide- M, fentrazamide, anilofos, cafenstrol, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of formulas I1.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

N.11 cellulose biosynthesis inhibitors: chlorothiamide, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1 );

N.12 uncoupling herbicides: dinoseb, dinoterb, DNOC and its salts;

N.13 auxin herbicides: 2,4-D and its salts and esters, claciphos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium , aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazoline, benazolineethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichloroprop-P and its salts and esters, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, galauxifen and its salts and esters (CAS 943832-60-8); MSPA and its salts and esters, MSRAthioethyl, MSRV and its salts and esters, mecoprop and its salts and esters, mecoprop-R and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TVA ( 2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9);

- 27 042940

N.14 auxin transfer inhibitors: diflufenzopyr, diflufenzopyr sodium, naptalam and naptalam sodium;

N.15 other herbicides: bromobutide, chlorflurenol, chloroflurenol-methyl, cinmethylin, cumiluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, diphenzoquat-methyl sulfate, dimetipine, DSMA, dimron, endothal and its salts, etobenzanide, flurenol, flurenolbutyl, flurprimidol, fosamine, ammonium fosamine, indanophane, maleic acid hydrazide, mefluidide, metham, methiozoline (CAS 403640-27-7), methyl azide, methyl bromide, methyl dimron, methyl iodide, MSMA , oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamine, tridifan;

O) Insecticides from classes O.1-O.29

O.1 acetylcholinesterase (AChE) inhibitors: aldicarb, alanicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pyrimicarb, propoxur, thiodicarb , thiophanox, trimetacarb, HMS, xylylcarb and triazamate; acephate, azamethifos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorphenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, epn, ethion, etoprofos, famfur, fenamiphos, fenitrothion, fenthion, fostyazate, heptenophos, imiciaphos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, metidathione, mevinphos, monocrotophos, naled, omethoate, oxydemeton -methyl, parathion, parathion-methyl, phentoate, phorate, fosalon, phosmet, phosphamidon, phoxim, pyrimiphos-methyl, profenophos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinalphos, sulphotep, tebupyrimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlor background, vamidothione;

O.2 antagonists of GABA-regulated chloride channels: endosulfan, chlordane; ethiprol, fipronil, flufiprol, pyrafluprol, pyriprol;

O.3 sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, betacifluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacipermethrin, theta-cypermethrin, zeta-cypermethrin, cyfenotrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperflutri n, metofluthrin, momfluorotrin, permethrin, phenothrin, pralletrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralometrin, and transfluthrin; DDT, methoxychlor;

O.4 nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, cycloxapride, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; (2E)-1-[(6chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; 1-[(6-chloropyridin-3yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine;

O.5 allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram;

O.6 chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;

O.7 juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

O.8 mixed non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, potassium antimonyl tartrate;

O.9 selective food blockers in Homoptera: pymetrozine, flonicamid;

O.10 tick growth inhibitors: clofentezin, hexythiazox, difluvidazine; ethoxazole;

O.11 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt culture proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Ciy34/35Ab1;

O.12 mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargit, tetradifon;

O.13 oxidative phosphorylation uncouplers that disrupt the proton gradient: chlorfenapyr, DNOC, sulfluramide;

O.14 nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, sodium thiosultap;

O.15 type 0 chitin biosynthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

O.16 inhibitors of chitin biosynthesis type 1: buprofezin;

O.17 substances that disrupt the molting process: cyromazine;

- 28 042940

O.18 ecdysone receptor agonists: methoxyfenoside, tebufenoside, halofenoside, fufenoside, chromafenoside;

O.19 Octopamine receptor agonists: amitraz;

O.20 mitochondrial complex III electron transfer inhibitors: hydramethylnon, acequinocyl, fluacripyrim;

O.21 mitochondrial complex I electron transfer inhibitors: phenazakhine, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;

O.22 voltage-gated sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide, N-( 3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]hydrazinecarboxamide;

O.23 acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat;

O.24 mitochondrial complex IV electron transfer inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

O.25 mitochondrial complex II electron transfer inhibitors: cyenopyraphene, cyflumethophen;

O.26 ryanodine receptor modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprol, tetraniliprole; (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-Ni-(1-methyl-2-methylsulfonylethyl)phthalamide , (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-Ni-(1-methyl-2-methylsulfonylethyl) phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl] - 1,2-dimethylhydrazinecarboxylate; N[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloro-2pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; Ν-[4-χλορ-2[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3 -carboxamide; N[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; N-[4,6-dibromo-2-[(dietide-diambda4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-III-pyrazole -5carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5 -carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro2-pyridyl)-1H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1,1-dimethylethyl)αmino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole -5-carboxamide; cyhalodiamide;

O.27. insecticidal active compounds with unknown or undetermined mechanism of action: afidopyropene, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, cryolite, dichloromesothiasis, dicofol, flufenerim, flomethochine, fluensulfone, fluhexafon, fluopyram , flupiradifuron, fluralaner, methoxadiazon, piperonyl butoxide, piflubumide, pyridalil, pyrifluquinasone, sulfoxaflor, thioxazafen, triflumesopyrim, 11-(4-chloro2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11- en-10-one, 3-(4'-fluoro-2,4dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[ 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, Bacillus firmus; (E/Z)-N-[1-[(6chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; (E/2)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[(6chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide; (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide; (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]2,2,2-trifluoroacetamide; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoropropanamide); N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluorothioacetamide; Ν-[1-[(6-χλορ-3nurudyl)methyl]-2-nipyridulidene]-2,2,2-trifluoro-N'-isopronylαcetαmidine; fluazaindolizine; 4-[5-(3,5dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluorobenzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]benzamide; N-[3-[[[2-iodine-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methylbenzamide ; N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]- 4-fluoro-N-methylbenzamide; 4-fluoro-N[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl ]phenyl]-N-methylbenzamide; 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]6(trifluoromethyl)phenyl]amino]carbonyl] phenyl]-N-methylbenzamide; 2-chloro-N-[3-[[[2-iodine-4-[1,2,2,2-tetraαfluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl] -3-pyridinecarboxamide; 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamo

- 29 042940 yl]phenyl]-2-methylbenzamide; 4-cyano-3-[(4-cyano-2-methylbenzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3hexafluoro-1-(trifluoromethyl)propyl] phenyl]-2-fluorobenzamide; N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyanophenyl]-4 -cyano-2-methylbenzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyanophenyl]-4cyano-2-methylbenzamide ; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyanophenyl]-4 -cyano-2-methylbenzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]- 2-methylbenzamide; 4-cyano-M-[2-cyano-5-[[2,6dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyanophenyl]-4-cyano-2methylbenzamide; 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropanamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropanamide; N,2-dimethyl-N[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropanamide; N-[4-χλορ-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthiopropanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthiopropanamide; Ν-[4-χλορ-2(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthiopropanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl3-methylthiopropanamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8nitroimidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide; 1-(1,2dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; N,5-dimethyl-N-pyridazin-4yl-1-(2,2,2-trifluoro-1-methylethyl)pyrazole-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1-methylpropyl)-5-methyl-N-pyridazin4-ylpyrazole-4-carboxamide; 1-(1,2-dimethylpronyl)-N,5-dimethyl-N-niridazin-4-ylpyrazole-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-piridazin-4-ylpirazol-4-carboxamide; N-methyl-1(2-fluoro-1-methylpropyl]-5-methyl-N-pyridazin-4-ylpyrazol-4-carboxamide; 1-(4,4-difluorocyclohexyl)N-ethyl-5-methyl-N- pyridazin-4-ylpyrazol-4-carboxamide; )-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole4-carboxamide; 2-(3 -pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;2-(3-pyridinyl)-N[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5yl]carbonyl]hydrazinecarboxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole- 5carboxamide, N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide, 2-(3-n-pyridinyl)-N-(2pyrimidinylmethyl)-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2Nindazole-5-carboxamide, Ν-[3-χλορ- 1 -(3-pyridyl)pyrazol-4-yl] - N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide;N-[3-xnop-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3.3.3 -trifluoropropylsulfinyl)propanamide; Ν-[3-χλορ-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethylpropanamide; Ν-[3-χλορ-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-Nethylpropanamide; sarolaner, lotilaner.

The active substances under the name component 2, their preparation and their activity against, for example, harmful fungi, are known (see: http://www.alanwood.net/pesticides/); these substances are commercially available. Compounds described by the IUPAC nomenclature, their preparation and their pesticidal activity are also known (see Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141317; EP-A 152031; EP-A 226917; EP-A 243970; EP-A 256503; EP-A 428941; EP-A 532022; EP-A 1028125; EP-A 1035122; EP-A 1201648; DE 19650197; DE 10021412 ; DE 102005009458; US 3296272; US 3325503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO

00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO03/11853;WO

03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO

04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO05/87773;WO

06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/2 4010, WO 13/047441; WO 13/162072; WO 13/092224; WO 11/135833; CN 1907024; CN 1456054; CN 103387541; CN 1309897; WO 09094442, WO 14/60177, WO 13 /116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441).

In addition, the present invention relates to agrochemical compositions containing a mixture of at least one compound I (component 1) and at least one additional active substance suitable for plant protection, for example, selected from groups A)-O) (component 2) , in particular one additional fungicide, for example one or more fungicides from groups A) to K), as described above, and if necessary, one suitable solvent or solid carrier. These mixtures are of particular interest because many of them show higher levels of effectiveness against harmful fungi at the same application rate. In addition, the control of harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more effective than the control of the same fungi with individual compounds I or individual fungicides from groups A)-K).

By using the compounds I together with at least one active substance from groups A) to O), a synergistic effect can be obtained, i.e. more than a simple addition of individual actions (synergistic mixtures) is achieved.

This can be achieved by applying compounds I and at least one additional active substance simultaneously, either together (for example, in the form of a tank mix), or separately, or sequentially, where the time interval between individual applications is chosen so that all still a sufficient amount of the active substance, which was applied first, during the application of additional(s) active(s) substance(s). The order of application is not essential for the implementation of the present invention.

When applying compound I and pesticide II sequentially, the time between both applications may vary, for example, in the range from 2 hours to 7 days. A wider range is also possible, namely from 0.25 hours to 30 days, preferably from 0.5 hours to 14 days, in particular from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferably from 2 hours to 1 day. In the case of a mixture containing a pesticide II selected from group L), it is preferred that pesticide II be used as the last treatment.

In accordance with the invention, the solid (dry matter) of biopesticides (with the exception of oils such as margosa seed oil) are considered as active components (for example, which are obtained after drying or evaporating the extraction or suspension medium in the case of liquid formulations of microbial pesticides).

In accordance with the present invention, the weight ratios and percentages used in the present description for a biological extract, such as quillaia extract, are given in terms of the total weight of the dry matter (solid) content of the corresponding extract(s).

The total weight ratios of compositions containing at least one microbial pesticide in the form of viable microbial cells, including dormant forms, can be determined using the number of CFU of the corresponding microorganism, calculating the total weight of the corresponding active component using the equation according to which 1x10 ¹⁰ CFU equals one gram of total the weight of the respective active ingredient. The colony forming unit is a measure of viable microbial cells, in particular fungal and bacterial cells. In addition, in this context, CFU can also be understood as the number of (immature) individual nematodes in the case of (entomopathogenic) nematode biopesticides such as Steinernema feltiae.

In binary mixtures and compositions according to the invention, the weight ratio of component 1) and component 2) mainly depends on the properties of the active components used, usually in the range from 1:10,000 to 10,000:1, often in the range from 1:100 to 100 :1, typically in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1 and, in particular, in the range from 1:2 to 2:1.

In accordance with additional embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is usually in the range from 1000:1 to 1:1, often in the range from 100:1 to 1:1, usually in the range from 50: 1 to 1:1, preferably in the range of 20:1 to 1:1, more preferably in the range of 10:1 to 1:1, even more preferably in the range of 4:1 to 1:1, and in particular in range from 2:1 to 1:1.

According to additional embodiments of mixtures and compositions, the weight ratio of component 1) and component 2) is typically in the range of 20,000:1 to 1:10, often in the range of 10,000:1 to 1:1, typically in the range of 5,000:1 to 5:1, preferably in the range of 5,000:1 to 10:1, more preferably in the range of 2,000:1 to 30:1, even more preferably in the range of 2,000:1 to 100:1, and in particular in the range from 1,000:1 to 100:1.

In accordance with additional embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is usually in the range from 1:1 to 1:1000, often in the range from 1:1 to 1:100, usually in the range from 1:1: 1 to 1:50, preferably in the range of 1:1 to 1:20, more preferably in the range of 1:1 to 1:10, even more preferably in the range of 1:1 to 1:4, and in particular range from 1:1 to 1:2.

In accordance with additional embodiments of the mixtures and compositions, the weight ratio of component 1) and component 2) is usually in the range from 10:1 to 1:20,000, often in the range from 1:1 to 1:10,000, usually in the range from 1:5 up to 1:5,000, preferably in the range of 1:10 to 1:5,000, more preferably in the range of 1:30 to 1:2,000, even more preferably in the range of 1:100 to 1:2,000, and in particular in the range from 1:100 to 1:1,000.

In ternary mixtures, i.e. compositions according to the invention containing component 1) and

- 31 042940 component 2) and compound III (component 3), the mass ratio of component 1) and component 2) depends on the properties of the active substances used, and is usually in the range from 1:100 to 100:1, usually in the range from 1 :50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, and in particular in the range of 1:4 to 4:1, and the weight ratio component 1) and component 3) is usually in the range from 1:100 to 100:1, usually in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1 :10 to 10:1 and, in particular, in the range from 1:4 to 4:1.

Any other active components, if necessary, are added to component 1) in a ratio of 20:1 to 1:20.

These ratios are also suitable for mixtures according to the invention applied by seed treatment.

When mixtures containing microbial pesticides are used for crop protection, application rates are preferably in the range of from about 1x10 ⁶ to 5x10 ¹⁶ (or more) CFU/ha, preferably from about 1x108 to about 1x10 ¹³ CFU/ha, and even more preferably from approximately 1x10 ⁹ to 5x1015 CFU/ha and particularly preferably 1x10 ¹² to 5x10 ¹⁴ CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e.g. Steinernema feltiae), application rates are preferably in the range of about 1x105 to 1x10 ¹² (or more), more preferably 1x10 ⁸ to 1x1011, even more preferably 5x10 ⁸ to 1x10 ¹⁰ individuals (eg as eggs, juveniles or any other life stages, preferably invasive juveniles) per ha.

When mixtures containing microbial pesticides are used for seed treatment, application rates for plant propagation material preferably range from about 1x10 ⁶ to about 1x10 ¹² (or more) cfu/seed. Preferably the concentration is from about 1x10 ⁶ to about 1x109 cfu/seed. In the case of microbial pesticides II, application rates for plant propagation material are also preferably in the range of from about 1x107 to about 1x10 ¹⁴ (or more) cfu per 100 kg of seed, preferably from about 1x109 to about 1x10 ¹² cfu per 100 kg of seed.

Preference is also given to mixtures containing as component 2) at least one active substance selected from inhibitors of complex III at the Qo site indicated in group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A .1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34) and (A.1.35 ); especially selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A. 1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34) and (A.1.35) .

Preference is also given to mixtures containing as component 2) at least one active substance selected from inhibitors of complex III at the Qi site indicated in group A), more preferably selected from compounds (A.2.1), (A.2.3) and (A.2.4); in particular, selected from (A.2.3) and (A.2.4).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the inhibitors of complex II indicated in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A. 3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18) , (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), ( A.3.28), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A. 3.37), (A.3.38) and (A.3.39); specifically selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A. 3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.29), (A.3.31) , (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38), and (A.3.39).

Preference is also given to mixtures containing as component 2) at least one active substance selected from other respiration inhibitors listed in group A), more preferably selected from compounds (A.4.5) and (A.4.11); in particular, (A.4.11).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the C14 demethylase inhibitors indicated in group B), more preferably selected from compounds (B.1.4), (B.1.5), (B. 1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22) , (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and ( V. 1.46); specifically selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B. 1.33), (B.1.34), (B.1.37), (B.138), (B.1.43) and (B.1.46).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the delta-14 reductase inhibitors indicated in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular, (B.2.4).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the phenylamide and acylamino acid fungicides listed in group C), more preferably selected from compounds (C.1.1), (C.1.2), (C .1.4) and (C.1.5); in particular, selected from (C.1.1) and (C.1.4).

- 32 042940

Preference is also given to mixtures containing as component 2) at least one active substance selected from other inhibitors of nucleic acid synthesis indicated in the group

C), more preferably selected from compounds (C.2.6), (C.2.7) and (C.2.8).

Preference is also given to mixtures containing as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1), (D.1.2), (D.1.5), (D. 2.4) and (D.2.6); in particular, selected from (D.1.2), (D.1.5) and (D.2.6).

Preference is also given to mixtures containing as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and (E. 2.3); in particular (E.1.3).

Preference is also given to mixtures containing as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the group G), more preferably selected from compounds (G.3.1), (G.3.3), (G.3.6), (G. 5.1), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), ( G.5.10) and (G.5.11); especially selected from (G.3.1), (G.5.1), (G.5.2) and (G.5.3).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the group H), more preferably selected from the compounds (H.2.2), (H.2.3), (H.2.5), (H. 2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); specifically selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

Preference is also given to mixtures containing as component 2) at least one active substance selected from group I), more preferably selected from compounds (I.2.2) and (I.2.5).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the group J), more preferably selected from compounds (J.1.2), (J.1.5), (J.1.8), (J. 1.11) and (J.1.12); in particular, (J.1.5).

Preference is also given to mixtures containing as component 2) at least one active substance selected from the group K), more preferably selected from compounds (K.1.41), (K.1.42), (K.1.44), (K. 1.45), (K.1.47) and (K.1.49); especially selected from (K.1.41), (K.1.44), (K.1.45), (K.1.47) and (K.1.49).

Biopesticides from group L1) and/or L2) may also have insecticidal, acaricidal, molluscicidal, pheromone, nematocidal, plant stress reducing, plant growth regulating, plant growth stimulating and/or yield increasing activity. Biopesticides from group L3) and/or L4) may also have fungicidal, bactericidal, virucidal, plant defense activating, plant stress reducing, plant growth regulating, plant growth stimulating and/or yield increasing activity. Biopesticides from group L5) may also have fungicidal, bactericidal, virucidal, plant defense activating, insecticidal, acaricidal, molluscicidal, pheromone and/or nematocidal activity.

Many of these biopesticides have been deposited under the deposit numbers below (prefixes such as ATCC or DSM refer to the acronym of the respective crop collection, for details see for example: http://www.wfcc.info/ccinfo/collection/ by_acronym/), listed in the literature, registered and/or commercially available: mixtures containing Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Kostanz, Germany (e.g. blastospores in BlossomProtect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245, originally isolated in the wheat region of Southern Brazil (Passo Fundo) until at least 1980 (BR 11005; e.g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains AbV5 and Ab-V6 (e.g. , in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US 8,445,255); B. amyloliquefaciens spp., plantarum D747, isolated from the air at Kikugawa-shi, Japan (US 20130236522 A1; FERM BP-8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefaciens spp., plantarum FZB24, isolated from soil in Brandenburg, Germany (also referred to as SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. Taegro® from Novozyme Biologicals, Inc., USA), B. amyloliquefaciens subsp. plantarum FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciens subsp. beans in Sutton Bonington, Nottinghamshire, United Kingdom, until at least 1988 (also referred to as 1430; NRRL B-50595; US 2012/0149571 A1; e.g. Integral® from BASF Corp., USA), species B. amyloliquefaciens, plantarum QST -713 isolated from peach orchards in 1995 in California, USA (NRRL B-21661; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. amyloliquefaciens spp., plantarum TJ1000, isolated in 1992 in South Dakota, USA ( also referred to as 1BE; ATSS VAA-390; SA 2471555 A1; e.g. QuickRoots™ from TJ Technologies, Watertown 33 042940 und, South Dakota, USA), B. firmus CNCM I-1582, a variant of the EIP-N1 parental strain (CNCM I1556) isolated from the soil of the central plains of Israel (WO 2009/ 126473, US 6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; e.g. PRO-MIX® BX from Premier Horticulture, Quebec, Canada ), B. pumilus INR-7, otherwise referred to as BU-F22 and BU-F33, isolated prior to at least 1993 from cucumber infected with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8445255), B. pumilus KFP9F isolated from grass rhizosphere in South Africa up to at least 2008 (NRRL B-50754; WO 2014/029697; e.g. BAC-UP or FUSION-P from BASF Agricultural Specialties (Pty) Ltd., South Africa) , B. pumilus QST 2808 isolated from soil collected in Pohnpei, Federated States of Micronesia in 1998 (NRRL B-30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 ( NRRL B-50304; US 8445255), B. subtilis FB17, also referred to as UD 1022 or UD10-22, isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735 WO 2011/109395); B. thuringiensis subsp. aizawai ABTS-1857, isolated from soil taken from a lawn in Ephraim, Wisconsin, USA, in 1987 (also referred to as ABG-6346; ATCC SD-1372; for example, XenTari® from BioFa AG, Münsingen, Germany), B. t. subspecies kurstaki ABTS-351, identical to HD-1, isolated in 1967 from a diseased black larva of a pink bollworm in Brownsville, Texas, USA (ATCC SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA), B. t. subsp. kurstaki SB4 isolated from carcasses of E. saccharina larvae (NRRL B-50753; e.g., Beta Pro® from BASF Agricultural Specialties (Pty) Ltd., South Africa), B. t. subsp. tenebrionis NB-176-1, mutant of strain NB-125, wild-type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585215 B1; e.g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA ( ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from larvae of the shield beetle Conchylocteniapunctata (NRRL 50757; e.g. Broadband® from BASF Agricultural Specialties (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also referred to as 29W), isolated in Rio de Janeiro, Brazil and SEMIA 587, isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from the fields of Wisconsin in the USA (Nitragin 61A152; Can. J. Plant. sci. 70, 661-666, 1990; e.g., in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28- 35, 2009; Biol Fertil Soils 47, 81-89, 2011); B. japonicum strains deposited in SEMIA known from Appl. Environ. microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in the Cerrados region, Brazil from Embrapa-Cerrados, used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil) , B. japonicum SEMIA 5080, produced under laboratory conditions with the assistance of Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, which is a natural variant of SEMIA 586 (CB1809) originally isolated in the USA (CPAC 7; for example, GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan in 2008 (NRRL B-50319; WO 2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON/M/91-08 isolated from oilseed rape (WO 1996 /021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin protein (alpha-beta) (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N-Tek from Plant Health Care plc, United Kingdom), Helicoverpa armigera nuclear polyhedrosis virus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea nuclear polyhedrosis virus (HzSNPV) single capsid (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nuclear polyhedrosis virus ABA-NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, United Kingdom), Isaria fumosorosea Apopka-97 isolated from mealybug on guinura in Apopka, Florida, USA (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g. PFR97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. anisopliae F52, also referred to as 275 or V275, isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in central Israel (US 6994849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89/030550; WO 1991/02051; Crop Protection 27, 352-361, 2008; e.g. BioAct ® from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from grass rhizosphere in South Africa up to at least 2008 (WO 2014/029697; NRRL B-50755; e.g. BACUP from BASF Agricultural Specialties (Pty) Ltd., South Africa), Pasteuria nishizawae Pnl isolated from

- 34 042940 mid-2000s soybean fields in Illinois, USA (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA) , Penicillium bilaiae (also referred to as P. bilaii) strains ATCC 18309 (=ATCC 74319), ATCC 20851 and/or ATCC 22348 (=ATCC 74318), originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97103, 1994; Can. J. Plant Sci 78(1), 91-102, 1998; US 5,026,417, WO 1995/017806; e.g., Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e.g. Regalia® SC from Marrone Biolnnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, United Kingdom), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, United Kingdom), Streptomyces microflavus NRRL B50550 (WO 2014/124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R, isolated in South Africa (NRRL 50759; also referred to as T. fertile; e.g. Trichoplus® from BASF Agricultural Specialties (Pty) Ltd., South Africa), T. harzianum T-22, also referred to as KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; for example, Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Worth, Ohio, USA).

According to one embodiment of the mixtures according to the invention, at least one pesticide II is selected from groups L1)-L5):

L1) microbial pesticides with fungicidal, bactericidal, virucidal and/or plant protection activating activity: Aureobasidiumpullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), B. amyloliquefaciens subsp. plantarum D747 (L. 1.3), B. amyloliquefaciens subsp. plantarum FZB24 (L.1.4), B. amyloliquefaciens subsp. plantarum FZB42 (L.1.5), B. amyloliquefaciens subsp. plantarum MBI600 (L.1.6), B. amyloliquefaciens subsp. plantarum QST-713 (L. 1.7), B. amyloliquefaciens subsp. plantarum TJ1000 (L.1.8), B. pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7 (L.1.11), B. pumilus KFP9F (L.1.12), B. pumilus QST 2808 (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FBI7 (L.1.15), Coniothyrium minitans CON/M/91-08 ( L.1.16), Metschnikowiafructicola nrrl y-30752 (l.1.17), Paenibacillus alvei nas6g6 (l.1.18), Penicillium Bilaiae ATCC 22348 (L.1.19), P. Bilaiae Atcc 20851 (L.1.20), Penicilli, Penicilli, Penicilli, Penicilli UM Bilaiae ATCC 18309 (L.1.21), Streptomyces microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41R (L.1.23), T. harzianum T-22 (L.1.24);

L2) biochemical pesticides with fungicidal, bactericidal, virucidal and/or plant protection activating activity: harpin protein (L.2.1), Reynoutria sachalinensis extract (L.2.2);

L3) microbial pesticides with insecticidal, acaricidal, molluscicidal and/or nematocidal activity: Bacillusfirmus I-1582 (L.3.1); B. thuringiensis subsp. aizawai ABTS-1857 (L.3.2), B. t. subspecies kurstaki ABTS-351 (L.3.3), B. t. subspecies kurstaki SB4 (L.3.4), B. t. subspecies tenebrionis NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nuclear polyhedrosis virus (HearNPV) (L.3.10), Helicoverpa zea nuclear polyhedrosis virus (HzNPV) ABA-NPV-U (L.3.11), Helicoverpa zea nuclear polyhedrosis virus (HzSNPV) single capsid (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces lilacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema carpocapsae (L.3.18), S. feltiae (L.3.19);

L4) biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromone and/or nematocidal activity: cis-jasmone (L.4.1), methyl jasmonate (L.4.2), quillaia extract (L.4.3);

L5) microbial pesticides with plant stress reducing, plant growth regulating, plant growth stimulating and/or plant yield increasing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), A. brasilense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), B. elkanii SEMIA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5079 (L. 5.7), B. japonicum SEMIA 5080 (L.5.8).

Moreover, the present invention relates to agrochemical compositions containing a mixture of XXX (component 1) and at least one biopesticide selected from group L) (component 2), in particular at least one biopesticide selected from groups L1) and L2) , as described above, and if necessary, at least one suitable excipient.

Moreover, the present invention relates to agrochemical compositions containing a mixture of XXX (component 1) and at least one biopesticide selected from group L) (component 2), in particular at least one biopesticide selected from groups L3) and L4 ), as described above, and if necessary, at least one suitable excipient.

Preference is also given to mixtures containing as pesticide II (component 2) a biopesticide selected from groups L1), L3) and L5), preferably selected from the strains indicated above as (L.1.2), (L.1.3), (L .1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.l.11), (L.1.12), (L.1.13) , (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L .5.6), (L.5.7), (L.5.8); (L.4.2), and (L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.l.ll), (L.1.12), (L.1.13), (L.1.14) ), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for processing propagation materials, ie. for seed treatment purposes and, likewise, for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, corn and legumes such as soybeans.

Preference is also given to mixtures containing as pesticide II (component 2) a biopesticide selected from groups L1), L3) and L5), preferably selected from the strains indicated above as (L1.1), (L.1.2), (L .1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15 ), (L.1.17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L .3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L. 1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11) , (L.3.12), (L.3.15) and (L.4.2). These mixtures are particularly suitable for foliar applications. These foliar mixtures are particularly suitable for vegetables, fruits, grapes, cereals, corn, legume crops such as soybeans.

Mixtures of active substances can be obtained in the form of compositions containing, in addition to the active ingredients, at least one inert component (auxiliary agent), in the usual way, for example, the way given for the compositions of compounds I. With regard to the usual components of such compositions, we hereby refer to the explanations given for compositions containing compounds I.

According to one embodiment, the microbial pesticides selected from groups L1), L3) and L5) encompass not only isolated, pure cultures of the respective microorganism as defined herein, but also its cell-free extract, its suspension in whole broth culture, either as a culture medium containing the metabolite, or as a purified metabolite obtained from a whole broth culture of the microorganism.

When live microorganisms such as pesticides II from groups L1), L3) and L5) form part of the compositions, such compositions can be prepared as compositions containing in addition to the active ingredients at least one adjuvant, in the usual way (for example, H.D. Burges: Formulation of Micobial Biopesticides, Springer, 1998). Suitable conventional types of such compositions are suspensions, fine powders, powders, pastes, granules, compacts, capsules and mixtures thereof. Examples of types of formulations are suspensions, capsules, pastes, lozenges, wettable powders or fine powders, compressed products, granules, insecticidal products, and gel formulations. In doing so, it should be taken into account that each type of composition or choice of adjuvant should not affect the viability of the microorganism during storage of the composition and, ultimately, its use in the treatment of soil, plant or plant propagation material. Suitable formulations are, for example, mentioned in WO 2008/002371, US 6955912, US 5422107.

Synthesis examples

With proper modification of the starting compounds, the procedures shown in the description of the synthesis examples below were used to obtain additional compounds I. The resulting compounds, together with physical data, are listed in table. I below.

HPLC-MS: HPLC column Kinetex XB C18 1.7 µm (50x2.1 mm); eluent: acetonitrile/water + 0.1% TFA (5 st gradient from 5:95 to 100:0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: quadrupole, electrospray ionization, 80 V (positive mode).

1. Synthesis of 2-[2-[(5,6-dimethyl-3-pyridyl)oxy]-6-fluorophenyl]-N,2-dimethylpropanamide (I-1)

To a solution of 2-[2-[(5,6-dimethyl-3-pyridyl)oxy]-6-fluorophenyl]propan-2-ol (1.07 g, 3.9 mmol) in acetic acid (15 ml) at k.t. acetonitrile (3 ml) and sulfuric acid (3 ml) were added. The reaction mixture was stirred for 2 h at 70° C., then ice was added and the reaction mixture was quenched with NaOH until pH>10. The aqueous phase was extracted with ethyl acetate, the organic phase was washed with water, dried over Na ₂ SO ₄ and concentrated. The crude product was purified by HPLC (water/acetonitrile) to give 101 mg (8%) of the title compound as a colorless oil.

¹ H-NMR (CDCl ₃ , δ in ppm): 8.2 (s, 1H); 7.1 (td, 1H); 7.0 (s, 1H); 6.8 (td, 1H); 6.5 (d, 1H); 5.9 (brs, 1H); 2.5(s, 3H); 2.3(s, 3H); 1.8 (s, 6H); 1.7 (s, 3H),

2. Synthesis of 5-[2-(1-benzyloxy-1-methylethyl)-3-fluorophenoxy]-2,3-dimethylpyrazine (I-3)

1H-NMR (CDCl ₃ , δ in ppm): 8.0 (s, 1H); 7.4-7.2 (m, 4H); 7.2 (m, 2H); 7.0 (td, 1H); 6.8 (d, 1H); 5.9 (q, 1H); 4.4 (d, 1H), 4.3 (d, 1H), 2.4 (s, 3H); 2.3(s, 3H); 1.6 (d, 3H).

Table I

- 36 042940

No. And R4 Q1 Q2 W Q3 So pl. f°ci HPLC-MS (R _t [min], M ⁺ +H) 1-1 sn H SNz SNz N COSNz 0.722 min; M ⁺ + H \u003d 317 1-2 N H SNz H ABOUT CH ₂ Ph 70 1.329 min; M ⁺ + H=353.2 1-3 N SNz SNz H ABOUT CH ₂ Ph 1.62 min; M ⁺ + H=367.1 1-4 N CH _{3 CF3} H ABOUT CH ₂ C ₆ H ₄ -4-F 1.405 min; M ⁺ + H = 438.39 1-5 CH H SNz SNz N _{COC6H4-4 -} F 0.881 min; M ⁺ + H=397 1-6 sn H SNz SNz N SOS ₆ H ₄ -4-C1 0.918 min; M ⁺ + H=413 1-7 sn H SNz SNz N COCH ₂ OC ₆ H ₄ -4-F 0.932 min; M ⁺ + H \u003d 427 1-8 sn H SNz SNz N COCH ₂ C1 0.787 min; M ⁺ + H \u003d 351 1-9 sn H SNz SNz N CO(CH ₂ ) ₂ CH ₃ 0.825 min; M ⁺ + H=345.1 1-10 sn H SNz SNz N CO(CH ₂ ) ₄ CH ₃ 0.945 min; M ⁺ + H=373.1 1-11 sn n SNz SNz N CO (CH ₂ ) sCH3 0.896 min; M ⁺ + H=359.0 1-12 sn n SNz SNz N SOSN ₂ SNz 0.789 min; M ⁺ + H=331.2 1-13 sn n SNz SNz N COCH ₂ morpholine 155 0.665 min; M ⁺ + H=402.2 1-14 N SNz SNz SNz ABOUT CH ₂ Ph 1.381 min; M ⁺ + H=381.1 1-15 N SNz _CF3 H ABOUT CH(CH ₃ )C ₆ H ₄ -4-F 1.420 min M ⁺ + H = 453.1

II. Biological research

Microstudy

The active compounds were separately formulated as stock solutions in dimethyl sulfoxide having a concentration of 10,000 ppm.

Example 1 Activity against gray mold Botrytis cinerea in a microtiter plate assay

Stock solutions were mixed in accordance with the specified ratio, pipetted onto a microtiter plate (MTP) and diluted with water to the indicated concentrations. Then a suspension of Botrci cinerea spores in DOB medium solution was added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTP was measured at a wavelength of 405 nm 9 days after inoculation.

In this study, samples that were treated with 31 ppm the active substance from examples I-2, I-3, I-5, I-14 and I-15, respectively, showed no more than 6% growth of pathogens.

Example 2 Activity Against Fusarium culmorum in a Microtiter Plate Assay

Stock solutions were mixed in accordance with the specified ratio, pipetted onto a microtiter plate (MTP) and diluted with water to the indicated concentrations. Then a suspension of Fusarium culmorum spores in an aqueous solution of biomalt or a solution of yeast-bactopeptone-sodium acetate was added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTP was measured at a wavelength of 405 nm 7 days after inoculation.

In this study, samples that were treated with 31 ppm the active substance from examples I-2, I-3, I-14 and I-15, respectively, showed no more than 17% growth of pathogens.

Example 3 Pyricularia oryzae Rice Blast Activity in a Microtiter Plate Assay

Stock solutions were mixed in accordance with the specified ratio, pipetted onto a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Pyricularia oryzae spores in DOB medium solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTP was measured at a wavelength of 405 nm 9 days after inoculation.

In this study, samples that were treated with 31 ppm active substance from examples I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I- 13, I-14 and I-15, respectively, showed no more than 13% pathogen growth.

The measured parameters were compared with the growth of the control variant without active compound (100%) and the value of a blank sample without fungi and active compound to determine the relative growth of pathogens in % in variants with the corresponding active compounds.

Claims (8)

1. Compound of formula I X y Q ^Q rIx^n^r ⁴ j where R ¹ means C _g C ₆ -alkyl; R ² means C _g C ₆ -alkyl; U means N or CR ³ ; R ³ means And; R ⁴ is selected from I, C1-C ₆ alkyl; Y means O; Z means CR ⁵ ; R ⁵ means And; X is independently selected from halogen; η means 1; Q ¹ is selected from C _g C ₆ alkyl, C 1 -C ₆ haloalkyl; Q ² is selected from I, C1-C ₆ alkyl; W means O or NQ ⁴ ; Q ³ is selected from C1-C1 ₅ -alkyl substituted with phenyl, where phenyl is not substituted or substituted by halogen, C (=O)C1-C1 ₅ -alkyl, C (=O) phenyl, where aliphatic fragments of the Q ³ group, with the exception of substituted The C1-C15 alkyl moieties are unsubstituted or substituted with the same or different Q ^3a groups independently selected from the following: Q ^3a halogen, C1-C ₆ -alkoxy, phenyl, where the phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q ^31a selected from the group consisting of halogen, where the phenyl group Q ³ is unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum possible number of the same or different groups Q ^3b , which are independently selected from the following: Q ^3b halogen, phenyl, where the phenyl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q ^311b selected from the group consisting of halogen; Q ⁴ means H; provided that if U stands for CR ³ W cannot be O; and their agriculturally acceptable salts. 2. A compound according to claim 1, wherein U is N and W is O. 3. The connection according to any one of claims 1, 2, where U is N and W is NQ ⁴ . 4. A compound according to any one of claims 1 to 3, wherein U is CR ³ and W is NQ ⁴ , where R ³ is in each case independently selected from H. 5. A fungicidal composition containing one compound of formula I according to any one of claims 1 to 4 or an agriculturally acceptable salt thereof. 6. The use of a compound of formula I according to any one of claims 1 to 4 and an agriculturally acceptable salt thereof for the control of phytopathogenic fungi. 7. A method for controlling phytopathogenic fungi, comprising treating fungi or materials, plants, soil or seeds to be protected from fungal attack with an effective amount of at least one compound of formula I according to any one of claims 1 to 4 or a composition according to claim 5. 8. Seeds coated with at least one compound of formula I according to any one of claims 1 to 4, or an agriculturally acceptable salt thereof, or a composition according to claim 5, in an amount of from 0.1 to 10 kg per 100 kg of seeds.