EP0865432A1 - Phenylacetic acid derivatives, process and intermediates for their preparation and their use as pesticides and/or fungicides - Google Patents

Abstract

The invention relates to phenylacetic acid derivatives of the formula (I), in which the substituents and the index have the following meaning: X is NOCH3, CHOCH3, CHCH3 and CHCH2CH3; Y is NRa and O; Ra, R1 are hydrogen and alkyl; R2 is cyano, nitro, halogen, alkyl, alkyl halide and alkoxy; m is 0, 1 or 2; R3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, alkyl halide, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino; A is a 5 or 6 membered hetero-aromatic ring; R4 is a substituted aryl; R5 is hydrogen, optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl. The invention also relates to the salts of said derivatives, a process and intermediates for the preparation and use thereof.

Description

 PHENYL ACETIC DERIVATIVES, METHODS AND INTERMEDIATE PRODUCTS FOR THE PRODUCTION THEREOF AND THEIR USE AS PESTICIDES AND / OR FUNGICIDES. description

The present invention relates to phenylacetic acid derivatives of the formula I.

in which the substituents and the index have the following meaning:

X NOCH ₃ , CHOCH ₃ , CHCH ₃ and CHCH ₂ CH ₃ ;

Y NR ^a and O;

R ^a , R ^{1 are} hydrogen and alkyl;

R ² cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R ^{2 to be} different if m is 2;

R ^{3 is} hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;

A is a 5- or 6-membered heteroaromatic ring;

R ⁴ substituted aryl;

R ⁵ hydrogen, optionally subst. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl, and their salts. The invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi. Phenylacetic acid derivatives for pest control are known from the literature [WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A

95 / 21,154].

The present invention was based on new compounds with improved activity as an object.

We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. In addition, processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use were found in this sense.

The compounds I are obtainable in various ways according to methods known per se in the literature.

In the synthesis of the compounds I, it is fundamentally irrelevant whether the group -C (X) -COYR ¹ or the group -CH ₂ ON = C (R ³ ) -C (AR ⁴ ) = NOR ^{5 is} built up first. The structure of the grouping -C (X) -COYR ¹ is, for example, from the literature cited at the beginning and from EP-A 242 070, EP-A 254 426, EP-A 370 629, EP-A 422 597, EP-A 463 488 , EP-A 472 300, EP-A 513 580, EP-A 656 352, EP-A 398 692 and PCT / EP 95 / 02,013.

The type of synthesis of the grouping -CH ₂ ON = C (R ³ ) -C (AR ⁴ ) = NOR ⁵ depends essentially on the type of the substituent R ³ .

1. In the event that R ³ does not mean halogen, the structure of the grouping -CH ₂ ON = C (R ³ ) -C (AR ⁴ ) = NOR ⁵ is generally carried out in such a way that a benzyl derivative of the formula II reacted with a hydroxyimine of the formula III. ()

L ¹ in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.

The required hydroxyimine III is obtained, for example, by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI

L ² in formula VI represents a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,

P. 307f, p. 370f and p. 385f; Houben-Weyl, Vol. 10/4, p. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f. 1.1 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula v, where v is then converted to I with the nucleophilically substituted reagent VI.

 The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,

 Pp. 1189f; Houben-Weyl, vol. E 14b, p. 307f, p. 370f and

 P. 385f; Houben-Weyl, Vol. 10/4, p. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f.

1.2 Analogously, it is also possible to prepare the required hydroxyimine of the formula III from a carbonylhydroxyimine VII by reaction with a hydroxylamine IXa or its salt IXb.

Q ^Ө in formula IXb stands for the anion of an acid, in particular an inorganic acid, for example. Halide like

Chloride.

The reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73f; Houben-Weyl, vol. E 14b, p. 369f and p. 385f.

1.3 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VII into a corresponding benzyloxyimine of the formula VIII, VIII being subsequently converted to I with the hydroxylamine IXa or its salt IXb.

The reaction is carried out in a manner known per se in an inert organic solvent according to the in Houben-Weyl, vol. E 14b, p. 369f; Houben-Weyl, Vol. 10/1, pp. 1189f and Houben-Weyl, Vol. 10/4, pp. 73f or EP-A 513 580.

1.4 A further possibility for the preparation of the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to give the benzylhydroxylamine Ha and the further reaction of Ha with a carbonyl compound X.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488, DE-Anm. No. 42 28 867.3 methods described.

The required carbonyl compound X is obtained, for example, by reacting a corresponding hydroxyiminocarbonyl compound VIa with a nucleophilically substituted reagent VI

or by reacting a corresponding dicarbonyl compound XI with a hydroxylamine IXa or its salt IXb

The reactions are carried out in a manner known per se in an inert organic solvent in accordance with the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55f, p. 73f, p. 180f and p. 217f; Houben-Weyl, vol. E 14b, pp. 307f and 369f, Houben-Weyl, vol. E 5, pp. 780f. 1.5 Correspondingly, the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyimino derivative VIa in the corresponding benzyloxyimino derivative of the formula V, V being subsequently converted to I with the nucleophilically substituted reagent VI as described above.

1.6 Analogously, the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl derivative of the formula XI into the benzyloxyimino derivative of the formula VIII and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.

2. Compounds I in which R ^{3 represents} a halogen atom are obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, p. 631; J. Org. Chem. 36, 233 (1977); J. Org. Chem. 57, 3245 (1992)]. The corresponding reactions to the halogen derivative are preferably carried out at stages I and VIII.

3. Compounds I in which R ³ is bonded to the skeleton via an O, S or N atom are obtained from the corresponding precursors in which the radical in question represents a halogen atom by methods known per se [cf. . Houben Weyl, Vol. E5, pp. 826f. and 1280f; J. Org. Chem. 36, 233 (1977);

J. Org. Chem. 46, 3623 (1981)]. The corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII. 4. Compounds I in which R ³ is bonded to the skeleton via an oxygen atom are in some cases also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, pp. 826f; Aust. J. Chem. 27, 1341-9 (1974)]. The corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII.

5. Compounds I in which Y is oxygen and R ^{3 is} not halogen are preferably obtained by compound X according to those described in EP-A 493 711

Methods with a lactone XII first converted into the corresponding benzoic acid XIII and XIII via the corresponding halides into the cyanocarboxylic acids XIV, which by way of the Pinner reaction (Angew. Chem. 94, 1 (1982)) into the α-keto esters XV and are subsequently converted into derivatives I (cf. EP-A 348 766, DE-A 37 05 389, EP-A 178 826, DE-A 36 23 921).

Compounds I in which R ^{1 is} hydrogen are obtained by this process by saponification of the esters XV and subsequent conversion to I.

Compounds I in which Y is NR ^a and R ^{3 is} not halogen are preferably obtained by converting a compound X according to the methods described in EP-A 493 711 with a lactone XII into the corresponding benzoic acid XIII and XIII about the corresponding

Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the α-keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)). The corresponding carboxamides are obtained from the derivatives XV by amidation and are subsequently converted into the compounds I.

7. In a modification of the process described under 6, the compounds XVI in which R ^{a is} hydrogen can also be obtained directly from the carboxylic acid halides by reaction with isocyanates and subsequent hydrolysis (EP-A 547 825).

8. In a further variant, compounds XVI are obtained by converting an ortho-halogen compound after metalation with oxalyl chloride into the corresponding keto acid chloride, which is then converted into the corresponding amide XVI with an amine (cf. J. Org.

 Chem. 46, 212f (1981); DE-A 40 42 280; Houben Weyl, Vol. E5, p. 972 f).

9. In a further variant, the compounds I in which Y denotes NR ^{a are obtained} , starting from the keto esters XV, by first derivatizing the keto function and converting the derivatives thus obtained to the amide using a corresponding amine (Houben-Weyl, Vol. E5, p. 941 f.)

The compounds II are known (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 585 751, EP-A 400 417, EP-A 251 082) or can be prepared by the methods described therein become. Particularly preferred intermediates for the preparation of the compounds I are the compounds III '

in which the substituents have the following meaning:

U ¹ oxygen or NOH,

U ^{2 is} oxygen, NOH or NOR ⁵ , where the radicals A, R ³ , R ⁴ and R ⁵ in general and in particular have the meaning given above.

Furthermore, intermediates of the general formula V are preferred for the preparation of the compounds I

in which U represents oxygen or NOH and the radicals A, X, Y, R ¹ , R ² , R ³ and R ⁴ and the index in general and in particular have the meaning given above.

Due to their C = C and C = N double bonds, the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.

If isomer mixtures are obtained in the synthesis, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (for example under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled. With regard to the C = X double bond, the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH ₃ or the -CH ₃ group in relation to the (O = C) YR ¹ group).

With regard to the -C (R ³ ) = NOCH ₂ double bond, the ice isomers of the compounds I are generally preferred with regard to their activity (configuration based on the radical R ³ in relation to the -OCH ₂ group).

The configuration of the -C (AR ⁴ ) = NOR ⁵ double bond generally has little influence on the activity of the compounds. If the effectiveness is influenced, the cis isomers (configuration based on the group AR ⁴ in relation to OR ⁵ ) are usually preferred.

In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example C ₁ -C ₆ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1 -Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl , 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2 Ethyl butyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; Alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;

Dialkylamino: an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;

Alkylcarbonyl: straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-); Alkylsulfonyl: straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-SO ₂ -); Alkylsulfoxyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via a sulfoxyl group (-S (= O) -); Alkylaminocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);

Dialkylaminocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);

Alkylaminothiocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);

Dialkylaminothiocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-); Haloalkyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C ₁ -C ₂ -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via an oxygen atom (-O-), e.g.

C ₁ -C ₆ alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trime thylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyl oxy and 1-ethyl-2-methylpropyloxy;

Alkoxycarbonyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via an oxycarbonyl group (-OC (= O) -);

Halogenalkoxy: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, and where these groups are bonded to the skeleton via an oxygen atom;

Alkylthio: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g.

C ₁ -C ₆ alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2- Dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; Alkenyl: straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C ₂ -C ₆ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2- Dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4- Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-p entenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1, 2-dimethyl-1- butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl -2-methyl-2-propenyl;

Alkenyloxy: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via an oxygen atom (-O-);

Alkenylthio: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via a sulfur atom (-S-);

Alkenylamino: an amino group which carries a straight-chain or branched alkenyl group having 2 to 6 carbon atoms as mentioned above; Alkenylcarbonyl: straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-); Alkynyl: straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C ₂ -C ₆ -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl 2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3- pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2- Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2- propinyl;

Alkynyloxy: straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via an oxygen atom (-O-); Alkynylthio: straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a sulfur atom (-S-);

Alkynylamino: an amino group which carries a straight-chain or branched alkynyl group having 2 to 6 carbon atoms as mentioned above; Alkynylcarbonyl: straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-); Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Cycloalkoxy: monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-);

Cycloalkylthio: monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-); Cycloalkylamino: an amino group bearing a monocyclic alkyl group having 3 to 6 carbon ring members as mentioned above;

Cycloalkenyl: monocyclic alkenyl groups with 5 to 8 carbon ring members, e.g. Cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; Cycloalkenyloxy: monocyclic alkenyl groups with 5 to 8

 Carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-); Cycloalkenylthio: monocyclic alkenyl groups with 5 to 8

Carbon ring members as mentioned above, which are bonded to the structure via a sulfur atom (-S-); Cycloalkenylamino: an amino group which carries a monocyclic alkenyl group with 5 to 8 carbon ring members as provided for above; Heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hereroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or (heterocyclyloxy) are bound to the skeleton via an oxygen atom, or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example, 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidone -Pyrrolidinyl, 3-isoxazoldinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 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, 2,3-dihydrofur-4-yl, 2,3-dihydro-fur-5 -yl, 2,5-dihydro-fur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothiene -4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrole -3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazole -3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazole -5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol3-yl, 2,3-dihydroisopyrazol-4 -yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3 -yl, 2,5-dihydroisopyrazole- 4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazole 3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazole 5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol 4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazole 2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazole 5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydro pyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3, 1-benzothiazin-2-yl, 1, 1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2- yl, 1,3-dithian-2-yl,

Aryl or aryloxy, arylthio, arylamino, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon residues which directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (arylamino) via a nitrogen atom or (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-SO ₂ -) are bound to the structure, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl - and sulfonyl residues;

Hetaryl or hetaryloxy, hetarylthio, hetarylamino, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-O-) or (hetarylthio) a sulfur atom (-S-), (hetarylamino) via a nitrogen atom or (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a Sulfonyl group (-SO ₂ -) are bound to the skeleton, for example

 5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2- yl;

5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom:

5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl , 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadi azol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazole 3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

 - Benzo-condensed 5-membered heteroaryl, containing one to three nitrogen atoms or a nitrogen atom and / or an oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen - Or can contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1,4-diyl group;

 - 5-membered heteroaryl bound via nitrogen, containing one to four nitrogen atoms. or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one

 Nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-the-n-1,4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;

6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1, 2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

- Benzo-fused 6-membered heteroaryl containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline, or the corresponding oxy, thio, amino, carbonyl or sulfonyl groups.

The expression "partially or completely halogenated" is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above. The term "substituted" in relation to the radicals mentioned in the definition of R ⁴ is intended to express that the groups in question are partially or completely halogenated and / or carry one to three of the following groups:

 - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

- C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfoxyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylaminocarbonyl, di -C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ alkylaminothiocarbonyl, di-C ₁ -C ₆ alkylaminothiocarbonyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy,

C (= NOR ^b ) -Z _n -R ^c or unsubstituted or substituted by usual groups benzyl, benzyloxy and benzylthio;

- C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylthio, aryl-C ₁ -C ₄ -alkyl, aryl-C ₁ -C ₄ -alkoxy, hetaryl , Hetaryloxy and Hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₆ - Alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfoxyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylaminocarbonyl, di-C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ - Alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl,

C ₂ -C ₆ alkenyloxy, C (= NOR ^b ) -Z _n -R ^c , or unsubstituted or substituted by conventional groups, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio.

The expression "substituted by conventional groups" is intended to express that the radicals in question can be partially or completely halogenated and / or can carry one to three of the following substituents: cyano, nitro, hydroxy, amino, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, di-C ₁ -C ₄ - alkylamino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, phenyl, phenoxy, benzyl and benzyloxy, and / or a C ₃ -C ₅ alkylene, C ₂ -C ₄ alkyleneoxy bonded to two adjacent atoms , C ₁ -C ₄ -Oxyalkylenoxy, and / or a group C (= NOR ^b ) -Z _n -R ^c .

5- or 6-membered heteroaromatic rings in the definition of A are to be understood in particular as the following groups A-1 to A-88. In the positions marked with * the bonds to R ^{4 take place} , the positions marked with # mark the bond to the rest of the molecule. The nitrogen atoms the 5-ring heteroaromatics with free valences can carry hydrogen or C ₁ -C ₆ alkyl in this position.

With regard to their biological action, preference is given to compounds of the formula I in which Y is oxygen and R ^{1 is} methyl.

Equally preferred are compounds of the formula I in which

X is NO ₃ and Y is NR ^a and R ^{a is} hydrogen or methyl.

Equally preferred are compounds of the formula I in which

X is NO ₃ and Y is NR ^a and R ^{1 is} hydrogen or methyl.

Also preferred are compounds of formula I in which X is NOCH ₃ and Y is NR ^a and R ^a and R ^{1 are} independently hydrogen or methyl.

Furthermore preferred are compounds of formula I in which

X is NO ₃ and Y is NR ^a and R ^{a is} hydrogen and R ^{1 is}

Methyl stands.

Also preferred are compounds of the formula I in which X is NOCH ₃ and Y is NR ^a and R ^{a is} hydrogen and R ^{1 is} hydrogen.

In addition, compounds of the formula I are preferred in which X

CHCH ₃ and Y means oxygen. In addition, compounds of the formula I are preferred in which X is CHCH ₂ CH ₃ and Y is oxygen.

In addition, compounds of the formula I are preferred in which X is NOCH ₃ and Y is O.

In addition, preference is given to compounds of the formula I in which X is CHOCH ₃ and Y is O. Compounds of the formula I in which R ^{1 is} methyl are particularly preferred.

In addition, compounds of the formula I are preferred in which Y is O and R ^{1 is} hydrogen.

Compounds of the formula I are also preferred in which m represents 0 or 1, in particular 0.

If m is 1, preference is given to compounds of the formula I in which R ^{2 is} halogen, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -alkoxy, in particular fluorine, chlorine, methyl and methoxy.

In addition, compounds I are preferred in which R ^{3 represents} one of the following substituents: hydrogen, hydroxy, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio and C ₃ -C ₆ cycloalkyl, in particular hydrogen, hydroxy, chlorine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, methylthio and cyclopropyl. In addition, compounds I are preferred in which R ^{3 represents} one of the following substituents: hydrogen, halogen,

C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and C ₃ -C ₆ cycloalkyl, in particular hydrogen, chlorine, methyl, ethyl, n -Propyl, iso-propyl, trifluoromethyl, methoxy, methylthio and cyclopropyl.

In addition, compounds I are preferred in which R ^{3 represents} hydrogen or C ₁ -C ₄ alkyl, in particular methyl. In addition, compounds I are preferred in which R ^{4 represents} substituted phenyl.

Furthermore, compounds I are preferred in which R ^{4 represents} phenyl substituted by customary groups. Likewise preferred are compounds I in which R ^{4 is} phenyl which carries at least one of the following substituents: cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ - Alkoxy, especially fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy and ethoxy.

Likewise preferred are compounds I in which R ^{4 is} phenyl which carries at least one trifluoromethyl group.

Likewise, preference is given to compounds I in which R ^{4 is} phenyl which carries a group C (= NOR ^b ) -Z _n -R ^c and can additionally carry one to three of the following substituents: cyano, nitro, halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl and

C ₁ -C ₄ alkoxy.

In addition, compounds I are preferred in which A represents one of the following radicals: A-2, A-6, A-10, A-11, A-12, A-17, A-18, A-20, A- 21, A-27, A-29, A-33, A-35, A-39, A-43, A-44, A-45, A-46, A-49, A-50, A-51, A-52, A-55, A-59, A-60, A-61, A-62, A-63, A-65, A-67, A-68, A-69, A-71, A- 72, A-76, A-78, A-79, A-80, A-81 and A-83.

In addition, compounds I are preferred in which A represents one of the following radicals: A-2, A-20, A-21, A-39, A-55, A-59, A-67, A-68, A- 69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-20.

In addition, compounds I are preferred in which A represents one of the following radicals: A-10, A-II, A-12, A-27, A-29, A-43, A-44, A-45, A- 46, A-63 and A-65, particularly preferably A-44.

In addition, compounds I are preferred in which A represents one of the following radicals: A-17, A-18, A-33, A-35, A-49, A-50, A-51, A-52, A- 60, A-61 and A-62, particularly preferably A-50.

In addition, compounds I are preferred in which A is A-2, A-20, A-21 and A-39, particularly preferably A-20. In addition, compounds I are preferred in which A is A-10, A-II and A-12, particularly preferably A-10.

In addition, compounds I are preferred in which A is A-17 and A-18, particularly preferably A-18. In addition, compounds I are preferred in which A is A-27, A-29, A-33 and A-35, particularly preferably A-33 and A-35.

In addition, compounds I are preferred in which A is A-43, A-44, A-45 and A-46, particularly preferably A-44 and A-46.

In addition, compounds I are preferred in which A is A-49, A-50, A-51 and A-52, particularly preferably A-50 and A-52. In addition, compounds I are preferred in which A is A-55, A-59, A-60, A-61, A-62, A-63 and A-65, particularly preferably A-60, A-62 and A- 65, stands.

In addition, compounds I are preferred in which A is A-67, A-68, A-69, A-71 and A-72, particularly preferably A-67 and A-68.

In addition, compounds I are preferred in which A is A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-79.

In addition, compounds of the formula I are preferred in which R ^{5 is} hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkoxy-C ₁ -C ₄ -alkyl, cyano-C ₁ -C ₄ -alkyl, amino-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylamino-C ₁ -C ₄ -alkyl, di- C ₁ -C ₄ alkylamino-C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl.

In addition, preference is given to compounds I in which R ^{5 represents} one of the following substituents: hydrogen, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, in particular hydrogen, methyl, ethyl, n-propyl, iso-propyl and methoxyethyl.

In addition, compounds I are preferred in which R ^{5 represents} one of the following substituents: hydrogen and C ₁ -C ₄ -alkyl, in particular methyl, ethyl, n-propyl and isopropyl, particularly preferably methyl.

In addition, compounds I are preferred in which R ^{5 is} C ₃ -C ₆ alkenyl and C ₃ -C ₆ haloalkenyl.

In addition, compounds I are preferred in which R ^{5 is} allyl. In addition, compounds I are preferred in which R ^{5 is}

trans-3-chloro-prop-2-enyl. Likewise, compounds I are preferred in which R ^{5 is} C ₃ -C ₆ alkynyl and C ₃ -C ₆ haloalkynyl.

In addition, compounds I are preferred in which R ^{5 is} propargyl.

In particular, in view of their use, the compounds I compiled in the tables below are preferred.

The compounds I are suitable as fungicides.

The compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides. They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans and Pumpkin family, as well as on the seeds of these plants.

They are particularly suitable for combating the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia types on cereals, Rhizoctonia and rice species Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Cereospora arachidicola on peanuts, Pseudocrichosidesella on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.

The compounds I are also suitable for combating

Harmful fungi in material protection (e.g. wood, paper, fibers or fabric) and in storage protection.

The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.

They can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compounds according to the invention. The formulations are prepared in a known manner for example, by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. Ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.

The application rates in crop protection, depending on the type of effect desired, are between 0.01 and 2.0 kg of active ingredient per ha. In the case of seed treatment, amounts of active ingredient generally range from 0.001 to 0.1 g, preferably 0.01 to 0.05 g required per kilogram of seed.

When used in material or storage protection, the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates are in

Material protection, for example 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material. The agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations: Sulfur, dithiocarbamates and their derivatives, such as iron, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, Tetramethylthiuramdisulfide, ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), ammonia complex of Zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl4,6-dinitrophenyl-isopropyl carbonate, 5-nitro-isophthalic acid diisopropyl ester ; heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethylphthalimidophosphonothioate, 5-amino-1- [bis- (dimethylamino) -phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoyl ) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl (4)) -benzimidazole, N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide,

N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl-sulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1, 2,3-thiadiazole, 2-rhodanmethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1, 4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, 2-methyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide, N- Cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide, 2-methyl-benzoic acid anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino-2, 2,2-trichloroethane, 2,6 -Dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecyl-mo rpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethyl-morpholine, N- [3- (p-tert-butylphenyl) -2 -methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, 1- [2nd - (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2nd , 4,6-trichlorophenoxyethyl) -N'-imidazol-yl urea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3-dimethyl- 1- (1H-1,2,4-triazol-1-yl) -2-butanol, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidinemethanol, 5-butyl-2-dimethylamino- 4-hydroxy-6-methyl-pyrimidine, bis (p-chlorophenyl) -3-pyridine methanol, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl -2-thioureido) -benzene, as well as various fungicides, such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2, 6-dimethyl-phenyl) -N-furoyl (2) -alaninate, DL-N- (2,6-dimethyl-phenyl) -N- (2'-methoxyacetyl) -alanine methyl ester, N- (2,6- Dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5- dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl] -1,3-oxazolidine-2,4-dione, 3- (3rd , 5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dime thylcyclopropane-1,2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4- triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl) -5- trifluoromethyl-3-chloro-2-aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

Strobilurins such as methyl-E-methoxyimino- [α- (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl } -3-methoxyacrylate, methyl-E-methoxyimino- [α- (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [α- (2,5-dimethylphenoxy) -o-tolyl] acetamide.

Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 -cyclopropyl-pyrimidin-2-yl) aniline.

Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile.

Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide.

The compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, storage protection and veterinary sectors. The harmful insects from the order of the butterflies (Lepidoptera) include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobisturaumumone, Cheimatobisturaumumone Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Helium, Heliothiothiothi, Heliothiothiothiothiothiis, Heliothiothiothiisi, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais , Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege stymicaliaiaia, monella lymphoma malachia lympia, monachroma, lympia triaxia triaxia, lympia ustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis eitrella, Pieris brassicae, Plathypena xabylaciaellaellaiaellaellaellaiaellaellaellaiaella pella Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Byus Bruchus pisorusum , Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornisis, Diabrotica, diabrotica, Epibrotusisinotilisisinodisinotis, Epabritus histopathy , Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema orynhiachono , Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria. From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropucitae, Cordylobia anthropucaga, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropacea, brassylaciaacropaceacita, brassylaciaacropia , Fannia canicularis, Gasterophilus intestinalis,

Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae,

Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria peetoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysoeyami, Phorbia antiqua, Phorbia brassicae, Phorbiaagomoletis, Phorbiaagolellais, Phorbiaagolellais ,

Tipula oleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenoptera, for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invieta.

From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leueopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensidata, Nezara pratensidata, Sol .

From the order of the plant suckers (Homoptera), for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui,

Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megourophusumisodishod , Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii. From the order of the termites (Isoptera), for example Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus,

Termes natalensis. From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinataus, Melanopladusana, Melanopladipana Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the arachnoid, for example arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata Otobius megnini, Paratetranyehus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus paeificus, Tetranychus telarius, Tetranychus urticae.

From the class of nematodes, for example, root gall nematodes, e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinetus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus elaytoni, Tylenchorhynchusus Prubus negate, Prelateus, chelate

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied. The application forms depend entirely on the purposes; she should ensure the finest possible distribution of the active compounds according to the invention in any case.

The active substance concentrations in the ready-to-use preparations can be varied over a wide range.

In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives. The application rate of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.

To produce directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions from medium to high boiling points, such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, by means of wetting agents,

 Adhesives, dispersants or emulsifiers are homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.

Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids as well as their alkali and alkaline earth metal salts, salts of sulfonated fatty alcohol alcohols, condensation products of sulfonated fatty alcohol alcohols and condensation products Naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, Laurylalkoholpolyglykoletheracetal, sorbitol esters , Lignin sulfite liquor and methyl cellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A preparation of the active ingredient with good adhesiveness (active ingredient content 23% by weight) is obtained in this way.

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2% by weight

Parts of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil are present (active ingredient content 9% by weight).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone,

30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 16% by weight). V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenalphasulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and in grind in a hammer mill (active ingredient content 80% by weight).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for use in the form of very small drops (active substance content 90% by weight).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight. -Share the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives one

 Spray liquor containing 0.1% by weight of the active ingredient.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers. Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.

Synthesis examples

The instructions given in the synthesis examples below were used with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are listed in the tables below with physical details. Example 1: Synthesis of (E, E, E) -2 - [[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] -α- (methoxyimino) phenylacetic acid methyl ester

 A solution of 2.7 g (9.23 mmol) of E, E-1- (1- (4-chlorophenyl) pyra¬zol-4-yl) -1-methoxyimino) propan-2-one-2-oxime 1.7 g of 30% sodium methylate solution (in methanol) were added to 20 ml of N, N-dimethylformamide and the mixture was stirred at room temperature (approx. 25 ° C.) for 15 min.

 After addition of 2.7 g (1 eq.) Of 2-bromomethyl-α-methoxyimino-phenylacetic acid methyl ester in 20 ml of N, N-dimethylformamide, the mixture was stirred for a further hour at room temperature. The mixture was then poured onto ice water and pentane was added, the product precipitating as a solid. The solid was isolated and purified by stirring with methanol. 4.2 g (91%) of the title compound were obtained (mp: 146-149 ° C.).

¹ H NMR (d ₆ -DMSO; δ in ppm): 2.07 (s, 3H); 3.71 (s, 3H); 3.87

 (s, 3H); 4.02 (s, 3H); 5.06 (s. 2H); 7.27 (m. 1H); 7.43

(m, 3H); 7.57 (d. 2H); 7.68 (d. 2H); 8.01 (s, 1H); 8.56 (s, 1H) Example 2 Synthesis of (E, E, E) -2 - [[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino ] oxy] methyl] -α- (methoxyimino) phenylacetic acid monomethylamide

 A solution of 1.6 g (3.2 mmol) of the compound from Example 1 in 50 ml of tetrahydrofuran was mixed with 2.5 g of 40% monomethylamine solution (in water) and for 24 hours at room temperature (approx. 25 ° C) stirred. The reaction mixture thus obtained was mixed with water and extracted with tert-butyl methyl ether. The organic phase was isolated, washed, dried and concentrated under reduced pressure. The residue obtained was stirred with methanol, the product crystallizing. 1.3 g (82%) of the title compound (mp: 100-103 ° C.) were obtained.

¹ H NMR (d ₆ -DMSO; δ in ppm): 2.09 (s, 3H); 2.66 (d. 3H); 3.81

 (s, 3H); 4.01 (s, 3H); 5.05 (s. 2H); 7.17 (m. 1H); 7.36

 (m, 3H); 7.54 (d. 2H); 7.65 (d. 2H); 8.03 (s, 1H); 8.21

 (m, 1H); 8.52 (s, 1H)

Example 3: Synthesis of (E, E, E) -2 - [[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] -α- (methoxyimino) phenylacetic acid amide

A mixture of 1.6 g (3.2 mmol) of the compound from Example 1, 20 ml of methanol, 30 ml of tetrahydrofuran and 20 ml of 25% ammonia solution (in water) was for 3 days at room temperature (approx. 25 ° C) stirred. The reaction mixture thus obtained was poured into ice water and extracted with dichloromethane. The organic phase was isolated, washed, dried and at min reduced pressure. The residue obtained was purified by column chromatography (silica gel; n-hexane / tert-butyl methyl ether 1: 1). 1.0 g (82%) of the title compound (mp: 164-167 ° C.) were obtained.

¹ H NMR (d ₆ -DMSO; δ in ppm): 2.12 (s, 3H); 3.82 (s, 3H); 4.02

 (s, 3H); 5.06 (s. 2H); 7.20 (m. 1H); 7.36-7.68 (m, 9H); 8.06

(s, 1H); 8.54 (s, 1H)

 Examples of the action against harmful fungi The fungicidal action of the compounds of the general formula I could be shown by the following experiments:

The active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight. % Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration. A) Efficacy against powdery mildew

Leaves of potted wheat seedlings of the "Frühgold" variety were washed with an aqueous spray mixture containing a stock solution of 10% active ingredient, 63% cyclohexanone and 27%

Emulsifier was prepared, sprayed and dusted with spores of powdery mildew (Erysiphe graminis var. Tritici) 24 hours after the spray coating had dried on. The test plants were then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area. In this test, those with 250 ppm of compounds no. 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.22 and 1.32 treated plants were 0 to 15% infected, while the untreated plants were 75% infected.

B) Efficacy against Plasmopara viticola

Leaves of potted vines of the "Müller-Thurgau" variety were sprayed with an aqueous spray mixture which had been prepared with a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier. In order to be able to assess the long-term effect of the substances, the plants were divided in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola. The vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually. In this test, those with 63 ppm of compound no.

1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.23, 1.24 and 1.32 treated plants 0 to 15% infestation, while the untreated plants too 70% were infected. Examples of the action against animal pests

The activity of the compounds of the general formula I against animal pests was demonstrated by the following tests:

The active ingredients were

 a. as a 0.1% solution in acetone or

b. as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) processed and with the desired concentration with acetone in the case of a. or with water in the case of b. diluted.

After the end of the tests, the lowest concentration was determined at which the compounds still caused 80 to 100% inhibition or mortality compared to untreated control tests (threshold of action or minimum concentration).

Effect against Tetranychus urticae (bean spider mite), contact effect, spray test

Potted bush beans with a fully developed pair of leaves were sprayed to runoff point in the spray booth with the aqueous active ingredient solution. The plants were guided over a running rail to the turntable of the spray booth and sprayed on all sides with 3 differently oriented nozzles when 30 cm ^{3 of} active ingredient solution was applied. The spraying process took about 20 seconds. The plants were heavily infested with mites and abundant oviposition. The effect was assessed after 5 days using a binocular. It was determined whether all stages were recorded evenly. The plants were under normal greenhouse conditions during this time. In this experiment, substance 1.17 from the table showed an activity threshold of 200 ppm.

Claims

claims

1. Phenylacetic acid derivatives of the formula I.

in which the substituents and the index have the following meaning:

X NOCH ₃ , CHOCH ₃ , CHCH ₃ and CHCH ₂ CH ₃ ;

Y NR ^a and O; R ^a , R ^{1 are} hydrogen and alkyl;

R ² cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R ^{2 to be} different if m is 2;

R ^{3 is} hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;

A is a 5- or 6-membered heteroaromatic ring;

R ⁴ substituted aryl;

R ⁵ hydrogen, optionally subst. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl, and their salts.

2. phenylacetic acid derivatives of the formula I according to claim 1, in which the substituents and the index have the following meaning: X NOCH ₃ , CHOCH ₃ , CHCH ₃ and CHCH ₂ CH ₃ ;

Y NR ^a and O; R ^a , R ^{1 are} hydrogen and C ₁ -C ₄ alkyl;

R ² cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkoxy; m is 0, 1 or 2, it being possible for the radicals R ^{2 to be} different if m is 2;

R ^{3 is} hydrogen, hydroxy, amino, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ alkylamino and di-C ₁ -C ₄ alkylamino;

A is a 5- or 6-membered heteroaromatic ring; R ⁴ substituted aryl;

R ^{5 is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl and C ₂ -C ₆ alkynyl, where these groups can be partially or completely halogenated and / or can carry one to three of the following radicals:

 - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

- C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, di- C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfoxyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ - haloalkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ alkylamino , Di-C ₁ -C ₆ alkylamino, C ₂ -C ₆ alkenyloxy,

- C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C ₁ -C ₄ -alkoxy, arylthio, aryl-C ₁ -C ₄ -alkylthio, hetaryl, hetaryloxy , Hetaryl-C ₁ -C ₄ -alkoxy, hetarylthio and hetaryl-C ₁ - C ₄ -alkylthio, where the cyclic radicals in turn can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, Hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfoxyl, C ₃ -C ₆ - Cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylaminocarbonyl, Di-C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ alkylaminothiocarbonyl, di-C ₁ -C ₆ alkylaminothiocarbonyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy, benzyl, benzyloxy, aryl, Aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR ^b ) -Z _n -R ^c ;

C ₃ -C ₆ cycloalkyl, _C5 -C ₈ cycloalkenyl, heterocyclyl, aryl and hetaryl, where the cyclic radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl,

C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfoxyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ haloalkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C ₁ - C ₆ alkylaminothiocarbonyl, di-C ₁ -C ₆ alkylaminothiocarbonyl, C ₂ -C ₆ alkenyl, C ₂ -C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylcarbonyl, hetaryl, hetaryloxy, hetarylcarbonyl, C (= NOR ^b ) -Z _n -R ^c or NR ^f -CO-DR ^g ;

Z oxygen, sulfur, or nitrogen, the

Nitrogen carries hydrogen or C ₁ -C ₆ alkyl; D is a direct bond, oxygen or NR ^h ; n 0 or 1;

R ^b , R ^c independently of one another are hydrogen or C ₁ -C ₆ -alkyl;

R ^{f is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl and C ₂ -C ₆ alkynyl;

R ^g , R ^h independently of one another hydrogen and C ₁ -C ₆ alkyl.

3. A process for the preparation of the compounds of formula I according to claim 1, in which R ^{3 is} not halogen, characterized in that a benzyl derivative of formula II in which L ^{1 represents} a nucleophilically exchangeable leaving group, in a manner known per se, with a hydroxyimine of the formula III

 implements.

4. A process for the preparation of the compounds of formula I according to claim 1, in which R ^{3 is} not halogen, characterized in that a benzyl derivative of formula II according to claim 3 in a manner known per se with a dihydroxyimine of formula IV

 to a compound of formula V

reacted and V then with a compound of formula VI

in which L ^{2 represents} a nucleophilically exchangeable leaving group, converts to I.

5. Process for the preparation of the compounds of the formula I according to claim 1, in which R ^{3 is} not halogen, characterized in that a benzyl derivative of the formula II according to claim 3 in a manner known per se with a carbonylhydroxyimine of the formula VII

 to a compound of formula VIII

VIII, then either a) first with hydroxylamine or its salt and then with a compound of formula VI (R ⁵ -L ² ) according to claim 4 or

b) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb

in which Q ^{θ stands} for the anion of an acid, converts to I.

6. Agents against animal pests or harmful fungi, containing conventional additives and an effective amount of a compound of formula I according to claim 1.

7. Composition according to claim 6 for combating animal pests from the class of insects, arachnids or nematodes.

8. A method for controlling animal pests or harmful fungi, characterized in that the pests or harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them are treated with an effective amount of a compound of the formula I according to claim 1.

9. Use of the compounds I according to claim 1 for the preparation of agents against animal pests or harmful fungi.

10. Use of the compounds I according to claim 1 for controlling animal pests or harmful fungi.

11. Compounds of the formula III '

in which the substituents have the following meaning: U ^{1 is} oxygen or NOH,

U ^{2 is} oxygen, NOH or NOR ⁵ , where the radicals A, R ³ , R ⁴ and R ^{5 have} the meaning given in claim 1.

12. Use of the compounds III 'according to claim 11 as intermediates.

13. Compounds of formula V

in which U represents oxygen or NOH and the radicals A, X, Y, R ¹ , R ² , R ³ and R ⁴ and the index have the meaning given in claim 1.

14. Use of the compounds V according to claim 13 as intermediates.