WO2002094793A1

WO2002094793A1 - Acylated 4-aminopyrazoles

Info

Publication number: WO2002094793A1
Application number: PCT/EP2002/005471
Authority: WO
Inventors: Peter Schäfer; Thomas Grote; Frank Schieweck; Uta Holzenkamp; Markus Gewehr; Wassilios Grammenos; Andreas Gypser; Bernd Müller; Joachim Rheinheimer; Ingo Rose; Hubert Sauter; Jordi Tormo I Blasco; Gisela Lorenz; Eberhard Ammermann; Reinhard Stierl; Siegfried Strathmann
Original assignee: Basf Aktiengesellschaft
Priority date: 2001-05-23
Filing date: 2002-05-17
Publication date: 2002-11-28

Abstract

The invention relates to acylated 4-aminopyrazoles of formula (I), wherein A represents one of the following groups: (A1) and (A2), # represents the bond to -C(R5R6)- and the variables have the meaning given in the description. The invention also relates to a method for producing the compounds (I), to agents containing the same and to their use in the control of animal pests and harmful fungi.

Description

Acylated 4-amino-pyrazoles

description

The invention relates to acylated 4-aminopyrazoles of the formula I,

where A is one of the following groups

where # denotes the bond to -C (R ⁵ R ⁶ ) - and the variables have the following meaning:

X ¹ , ² , Y? independently of one another oxygen or sulfur;

R ¹ H, Ci-Cβ-alkyl, Ci-C _ß -haloalkyl, Ci-Cg-Al oxy-Ci-C _δ - alkyl or C ₃ -C ₆ cycloalkyl;

R ² Ci-C _δ- alkyl, Ci-Ce-haloalkyl, -C-C ₆ - lko y-Cι-C ₆ alkyl or C ₃ -C ₆ cycloalkyl;

R ³ H, halogen, cyano, C ₁ -C ₆ -alkyl, Ci-C _δ -haloalkyl,

-C (= 0) -0R ^α or -C (= 0) -NR ^α R ^ß ;

R ^α , RP independently of one another H or Ci-C _δ alkyl;

R ⁴ H, -CC ₅ alkyl, C -C ₆ cyanoalkyl, -C ₆ alkoxycarbo - nyl-Ci-Cβ-alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or - C (= X ² ) -R ^a ;

R Ci-C _ß -alkoxy, Ci-C _δ -haloalkoxy, C -C ₆ -alkenyloxy,

C -C ₆ -alkynyloxy, Ci-Ce-alkoxy-Ci-Cg-alkoxy, C ₃ -C ₆ -cycloalkoxy, Cι-C ₆ -alkylthio, -C (= 0) -NR R,

Phenoxy or benzyloxy, where the ring systems can carry one to three substituents selected from the group

Group halogen, Ci-Cε-alkyl and Ci-Cg-alkoxy, Phenylthio, which can carry a substituent selected from the group halogen and Ci-Cβ-alkyl;

R ⁵ , R ⁶ independently of one another H, halogen or Ci-C _ß- alkyl or R ⁵ and R ⁶ together with the carbon atom to which they are attached form a three- to six-membered ring;

Q ^1, Q ^2, Q ³ are independently H, halogen, nitro, cyano, hy- droxy, Cι-C ₆ -alkyl, C ₆ haloalkyl, Cι-C ₆ alkoxy,

Ci-Cg-haloalkoxy, C2-C. ₆ -Alkenyloxy, -C-C ₆ -alkylcarbonyloxy, Ci-Cg-alkylthio, Ci-C _ß -haloalkylthio, - C (= 0) -R ^α , -C (= 0) -OR ^α , -Cι-C ₆ -Halogenalkoxycarbonyl, Ci-C _δ -alkoxy-Ci-Cg-alkoxycarbonyl, C ₃ -C ₆ -cycloalkoxycarbonyl, Ci-C _ß -Alkylsulfinyl, Ci-Cg-Alkylsulfonyl, -

C (= 0) -NR ^f R5- C ₃ -C ₆ cycloalkyl,

1 I

-C (R ^b ) -OC (R ^c ) -C (R ^d ) -MO, -C (R ^b ) = N-0-R ^β ,

Phenyl, phenoxy, benzyl, benzyloxy, phenylthio, 2-pyridinoxy, 4-pyridinoxy, 2-pyrimidinoxy, 4-pyrimidinoxy, the ring systems being one to three of the substituents selected from: Ci-Cg-alkylthio, Ci-C _ß - Alkylsulfinyl, Ci-Cg-Alkylsulfonyl and Ci-Cg-Alkylcarbonyl or the group R ^{y can} wear, or

Q ² and Q ³ together form a chain -X ³ -C (R ⁷ ) = N-, -N (R ⁸ ) -N = N-, where X ³ and N (R ⁸ ) either in 3- or in 4 position;

R ^b H or -CC ₆ alkyl;

R ^c , R ^d independently of one another H, Ci-Cβ-alkyl,

Cι-C ₆ haloalkyl, Cι-C ₆ -alkoxy-Cχ-C ₆ alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkynyl, Cι-C ₆ -Alkoxycarbo- nyl, C ₆ -C Alkenyloxy -CC ₆ alkyl,

Phenyl, phenyl-Ci-C _δ- alkyl or phenoxy-Ci-Cg-alkyl, wherein the ring systems can carry one to three substituents selected from the group halogen, -CC ₆ -alkyl and Ci-Cε-alkoxy;

M CH ₂ or a direct bond; R ^e is H, Cι-C ₅ alkyl, C ₂ -C ₆ alkoxycarbonyl-Cι-C ₆ alkyl, C ₃ -C 6 -alkenyl, C ₃ -C ₆ -alkynyl or benzyl, where the aromatic ring one to three Can carry substituents selected from the group halogen, -CC _e alkyl and Ci-C _ß alkoxy;

R ^f , R ^< ? independently of one another H, -CC ₆ alkyl, C ₃ -C ₆ cycloalkyl, or

R ^f and R9 together form a chain - (CH. ₄ -,

- (CH ₂ ) ₅ - or -CH ₂ -CH2-0-CH ₂ -CH ₂ -;

R ^γ halogen, hydroxy, nitro, cyano, Ci-Cg-alkyl,

Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-C _ß -haloalkoxy;

H, halogen, nitro, cyano, hydroxy, SH, -SC≡N, Ci-C _δ -Alk l,

Ci-C _ß -haloalkyl, Ci-Cg-alkylthio, Ci-C _ß -haloalkylthio, C ₂ -C ₆ -cyanoalkyl, Ci-C _δ -alkoxy-Ci-Cg-alkyl, carboxyl-Ci-C _δ -alkyl, C ₂ -C ₆ alkoxycarbonyl -CC-C ₆ alkyl, C -Cg alkenyl,

C ₂ -C ₆ alkynyl, -C-C ₆ alkoxy, Ci-C _ß -haloalkoxy, R ^f R9- -C (= 0) -R ^α , -C (= 0) -OR ^α , -C (= 0) -NR ^f R9, -C (R ^α ) = N-OR ^h , Ci-Cg-alkylsulfinyl, Ci-Cg-alkylsulfonyl, C ₃ -C ₆ - cycloalkyl, Cs-Cg-cycloalkenyl or C ₃ -C ₆ cycloalkoxy,

Phenyl, phenyl-Ci-Cg-alkyl, phenoxy, phenoxy-Ci-Cg-alkyl, phenyl-Cx-C _δ- alkoxy, phenylthio, pyridyl, pyridyl-Ci-Cg-alkyl, pyrazolyl, pyrazolyl-Ci-Cg -alkyl, thienyl, thienyl-Ci-Cg-alkyl, thiazolyl, thiazolyl-Ci-C _ß -alkyl, isoxazolyl or isoxazolyl-Ci-Cg-alkyl, wherein the ring systems can carry one to three groups R ^γ ;

R ^h H, -CC ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl,

Ca-Cg-Alkoxycarbonyl-Ci-Cg-alkyl, or benzyl, which one to three substituents selected from the

Group halogen, Ci-C _δ alkyl and Ci-Cg-alkoxy can carry;

R ^8, R ^9, R ¹⁰ are independently H, Ci-C _ß -alkyl, halo-C ₆ alkyl, Cι-C ₆ -alkoxy-Cι-Cg-alkyl, C ₂ -C ₆ alkenyl,

C ₂ -C ₆ alkynyl, -C-C ₆ alkylcarbonyl, -C (= 0) -OR ^α , -C (= 0) -NR ^f R5, Cι-C ₆ alkylsulfonyl, C ₃ -C ₆ cycloalkyl , Cs-Cg-cycloalkenyl,

Phenyl or phenyl-Ci-C _ß- alkyl, wherein the ring systems can carry one to three groups R; Y ^ Y ² together form a chain = NN (R ⁹ ) -N = or

= NN (R ¹⁰ ) -C (R ^1:) =, where CCR ¹¹ ) is in either position 3 or 4;

R ¹¹ H, halogen, nitro, cyano, -CC ₆ alkyl or Ci-Cg haloalkyl;

Q, Q ⁵ independently of one another H, halogen, hydroxy, C ₁ -C ₆ -alkyl,

Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Cx-Cg-haloalkoxy, phenoxy or benzyloxy, where the ring systems can carry one to three groups R ^γ .

In addition, the invention relates to processes for the preparation of the compounds I, compositions comprising them and the use of the compounds I for controlling animal pests and harmful fungi.

Acylated 5-aminopyrazoles with herbicidal, fungicidal and insecticidal activity are already known, for example from DE-A 36 09 542, WO-A 96/21653 and WO-A 00/11951.

Acylated 4-aminopyrazoles are known as intermediates for pharmaceuticals, for example from J. med. Che. 30 (1987) 91-96 and J. ed. Chem., 31 (1988) 454-461.

It is the object of this invention to provide acylated 4-aminopyrazoles for controlling animal pests and harmful fungi.

We have found that this object is achieved by the acylated 4-aminopyrazoles of the formula I. Furthermore, processes for the preparation of the compounds I and compositions containing them for controlling animal pests and harmful fungi were found. The fungicidal activity is preferred.

Compounds of the formula I differ from compounds from the abovementioned publications by the substitution pattern on the pyrazole ring.

The compounds of formula I are accessible in various ways. For example, compounds of the formula I in which X ^{1 is} oxygen and R ^{4 are} hydrogen are obtained by reacting 4-aminopyrazoles of the formula II

where the variables R ¹ , R ² and R ^{3 have} the meaning given in formula I, with carboxylic acid derivatives of the formula III in which R ⁵ , R ⁶ and A have the meaning given for formula I and L represents a nucleophilically displaceable leaving group. For L are, for example, -C ₄ alkoxy groups or halogen, such as chlorine or bromine, especially chlorine.

This reaction usually takes place at temperatures from 0 ° C. to 100 ° C., preferably 0 ° C. to 50 ° C., in an inert organic solvent in the presence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butylme ethyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone as well as dimethyl sulfoxide, dimethyl formamide and dimethylacetamide and ethyl acetate. Mixtures of the solvents mentioned can also be used.

Bases generally include alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate and alkali metal hydrogen carbonates such as sodium hydrogen carbonate, as well as organic bases, e.g. Tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well as bicyclic amines. Triethylamine, pyridine and 4-dimethylaminopyridine are particularly preferred.

The bases are generally used in equimolar amounts, but they can also be used in excess or, if appropriate, as a solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use one of the reactants in excess. The reaction mixtures are worked up in the customary manner, for example by mixing with dilute acid, water or dilute base, separating the phases and, if appropriate, purifying the crude products chromatographically. The intermediate and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are freed or purified of volatile components under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting.

The starting materials of the formula II required for the preparation of the compounds I are known in the literature, for example from DE-A 3113222, Pharmazie (1998), 53 (5), 346-348 or Bioorg. Med. Chem. Lett. (200), 10 (17), 1983-1986, or can be prepared according to the literature cited.

The starting materials of the formula III required for the preparation of the compounds I are known in the literature, for example from WO-A 95/31448, WO-A 96/21653, WO-A 97/18198,

WO-A 98/02424, WO-A 98/05670, DE-A 198 38 708, WO-A 00/11951 and DE-A 198 46 008 or can be prepared according to the literature cited.

In the definitions of the symbols given in the formulas above, collective terms were used which are generally representative of the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated, straight-chain or branched hydrocarbon radicals with 1 to 4 or 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dirnethylethyl, pentyl , 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,

1,1-Dimethylpropyl, 1,2-Dirnethylpropyl, 1-Methylpenty1, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl, 1,2-Dirnethylbutyl, 1,3-Dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-triethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-l-methyl - propyl and 1-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms (as mentioned above), it being possible in these groups to partially or completely replace the hydrogen atoms by halogen atoms as mentioned above, for example C ₁ -C ₂ -haloalkyl such as chloromethyl, bromomethyl, dichloro ethyl, Trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-di-fluoroethyl, 2,2,2-trifluoroethyl, 2-chloro 2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl;

Cyanoalkyl: straight-chain or branched alkyl groups with 2 to 6 carbon atoms (as mentioned above), in which case the hydrogen atoms in these groups can be partially or completely replaced by cyano groups, such as 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropy1, 2 -Cyanopropy1, 3-cyanopropy1;

Alkoxy: straight-chain or branched alkyl groups with 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);

Haloalkoxy: straight-chain or branched haloalkyl groups with 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);

Alkylthlo: straight-chain or branched alkyl groups with 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (-S-);

Haloalkylthio: straight-chain or branched haloalkyl groups with 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (-S-);

Alkoxyalkyl: an alkoxy group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a straight-chain or branched alkyl group with 1 to 6 carbon atoms (as mentioned above);

(Called as above) a carboxyl group (-C (= 0) -0-), which atoms with a straight-chain or branched alkyl group having 1 to 6 carbon ^¬ bonded to the skeleton; alkoxycarbonylalkyl

Alkylcarbonyl: a straight-chain or branched alkyl group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-C0-);

Alkoxycarbonyl: an alkoxy group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-CO-); Haloalkoxycarbonyl: a haloalkoxy group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-C0-);

Alkylcarbonyloxy: a straight-chain or branched alkyl group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyloxy group (-C0 ₂ -);

Alkylsulfinyl: a straight-chain or branched alkyl group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfinyl group (-SO-);

Alkylsulfonyl: a straight-chain or branched alkyl group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfonyl group (-S0 ₂ -);

Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4 or 6 carbon atoms and a double bond in any position such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl , 1-methyl-l-propenyl, 2-methyl-l-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, l-dimethyl-2-propenyl, 1, 2-dimethyl-l-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-lpropenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l -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 , l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl l-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, l-dimethyl-2-butenyl, 1, l-dimethyl-3-bute- nyl, 1,2-dimethyl-l-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: unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 6 carbon atoms and a double bond in any position not adjacent to the hetero atom. sition (as mentioned above) which are bonded to the structure via an oxygen atom (-0-);

Alkynyl: straight-chain or branched hydrocarbon groups with 2, 3, 4 or 6 carbon atoms and a triple bond in any position, for example C ₂ -C ₆ -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- Butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2- Methyl-3-butynyl, 3-methyl-1-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3- Methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1, 1-dimethyl- 3-butynyl, l, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3- butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl;

Alkynyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a triple bond in any position (as mentioned above) which is not adjacent to the hetero atom and which are bonded to the structure via an oxygen atom (-0-);

Cycloalkyl: monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

Cycloalkenyl: monocyclic unsaturated hydrocarbon groups with 5 to 6 carbon ring members and a double bond in any position such as 1-cyclopentyl, 2-cyclopentyl, 3-cyclopentyl, 1-cyclohexyl, 2-cyclohexyl, 3-cyclohexyl;

Cycloalkoxy: monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, which are bonded to the structure via an oxygen atom (-0-);

Cycloalkoxycarbonyl: monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, which are bonded to the structure via a carboxyl group (-0- (C = 0));

With regard to the intended use of the aminopyrazoles of the formula I, the following meanings of the substituents ten, each individually or in combination, particularly preferred:

Compounds of the formula I in which X ^{1 is} oxygen are preferred.

In addition, compounds of the formula I in which X ^{2 is} oxygen are preferred.

Also preferred are compounds of formula I in which X ^{3 is} oxygen.

Also preferred are compounds of the formula I in which X ^{1 is} oxygen and A is A ² .

Also preferred are compounds of the formula I in which R ^{1 is} hydrogen or Ci-Cg-alkyl.

Compounds of the formula I in which R ^{1 is} methyl are particularly preferred.

Also preferred are compounds of the formula I in which R ^{2 is} Ci-Cg-alkyl.

Preference is furthermore given to compounds of the formula I in which R ^{3 represents} -C (= 0) -0R ^α .

Further preferred are compounds of formula I, in which R ⁴ are hydrogen, C ₆ alkyl, C ₂ -C ₆ cyanoalkyl, Cι-C ₆ -Alkoxycar- carbonyl-Cι-C ₆ alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -alkynyl or -C (= X ² ) -Cχ-Cg-alkoxy means.

Compounds of the formula I in which R ^{4 is} hydrogen are particularly preferred.

Preference is furthermore given to compounds of the formula I in which R ⁵ and R ⁶ independently of one another represent hydrogen, halogen or Ci-Cg-alkyl, in particular hydrogen.

Compounds of the formula I in which Q ¹ and Q ² independently of one another are hydrogen are particularly preferred.

Furthermore, preference is given to compounds of the formula I in which Q ² and Q ³ independently of one another for hydroxy, Ci-Cg-alkoxy, Cχ-Cg-halogenoalkoxy, C ₂ -Cg-alkenyloxy or phenoxy, which one to three substituents selected from R ^r and Ci-Cε-alkylcarbonyl can wear, or -C (R ^b ) -OC (Rc) -c (R ^d ) - -0 s tehen.

Preference is furthermore given to compounds of the formula I in which Q ² and Q ³ together form a chain -0-C (R ⁷ ) = N-.

In addition, particular preference is given to compounds of the formula I in which Q ^{3 is} phenoxy which is substituted in the 4-position by a group R ^γ .

Compounds of the formula I are furthermore preferred in which Q ⁴ , Q ⁵ independently of one another are hydrogen or halogen, in particular hydrogen.

Furthermore, compounds of the formula I are preferred in which R ^c and R ^d independently of one another are hydrogen, Ci-Cg-alkyl, Cχ-Cg-alkoxy-Ci-Cg-alkyl, phenyl or phenoxy-Ci-Cg-alkyl, where the ring systems can carry one to three substituents selected from the group halogen, Cχ-Cg-alkyl and Cχ-Cg-alkoxy.

Preference is furthermore given to compounds of the formula I in which M is a direct bond.

In addition, compounds of the formula I are preferred in which R ^{e is} hydrogen or Ci-Cg-alkyl.

Compounds of the formula I in which R ^f and R9 independently of one another are hydrogen or Cχ-Cg-alkyl are preferred.

Also preferred are compounds of formula I in which R ^{γ is} halogen, hydroxy, nitro, cyano, Cχ-Cg-alkyl or Cχ-Cg-haloalkyl.

In addition, compounds of the formula I are preferred in which R ^{7 is} hydrogen, halogen, hydroxy, SH, Cχ-C ₆ -alkyl, Cχ-C ₆ -haloalkyl, C ₂ -C ₆ -cyanoalkyl, Cχ-Cg-alkoxy- Cχ-C ₆ -alkyl, C-Cg-alkoxycarbonyl-Cχ-Cg-alkyl, Cχ-Cg-alkoxy, Cχ-Cg-alkylthio, C ₂ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl , Phenyl, pyridyl or benzyl, where the ring systems can carry one to three groups R ^y .

Compounds of the formula I in which R ^{7 is} Cχ-Cg-alkyl, phenyl or pyridyl, where the ring systems can carry one to three groups R ^γ , are furthermore particularly preferred.

Preference is furthermore given to compounds of the formula I in which R ^{h is} hydrogen or Cχ-Cg-alkyl. In addition, compounds of the formula I are preferred in which R ⁸ , R ⁹ and R ¹⁰ independently of one another denote hydrogen, Cχ-Cg-alkyl, phenyl or benzyl, where the ring systems can carry one to three groups R ^γ .

Particularly preferred are compounds of formula I in which R ⁸ , R ⁹ and R ¹⁰ independently of one another are Cχ-Cg-alkyl.

Preference is furthermore given to compounds of the formula I in which Y ¹ and Y ² together form a chain = NN (R ⁹ ) -N = or = NN (R ¹⁰ ) -C (R ^{1: L} ) =, where C (R ^{1 : l} ) is either in position 3 or 4 and R ^{11 is} hydrogen or Cχ-C ₆ alkyl.

Compounds of the formula 1.1 are also preferred:

Compounds of the formula 1.2 are also preferred;

Compounds of the formula 1.3 are also preferred:

Compounds of the formula 1.4 are also preferred:

Compounds of the formula 1.5 are also preferred:

Compounds of the formula 1.6 are also preferred:

Also preferred are compounds of the formulas 1.1-1.4, where X ^{1 is} oxygen, R ¹ = hydrogen or Cχ-C ₂ -alkyl, R ² Cχ-C ₃ -alkyl, R ³ Cχ-C-alkyloxycarbonyl and R ⁴ , R ⁵ , R ⁶ , Q ¹ , Q ² , Q ⁴ and Q ^{5 are} hydrogen and Q ^{3 is} Cχ-Cg-alkoxy, Cχ-C ₂ -haloalkoxy or unsubstituted or mono- to trisubstituted phenoxy, the substituents being selected from the group fluorine, chlorine, CH ₃ , CF ₃ , OCH ₃ , 0CF ₂ H, nitro and cyano.

Preference is also given to compounds of the formula 1.5, where X ^{1 is} oxygen, R ^{1 is} hydrogen or -CC ₂ -alkyl, R ^{2 is} Cχ-C ₃ -alkyl, R ^{3 is} Cχ-C-alkyloxycarbonyl and R ⁴ , R ⁵ , R ⁶ , Q. ¹ , Q ⁴ and Q ^{5 are} hydrogen, or Q2 and Q3 together form a chain -0-C (R ⁷ ) = N- and R ^{7 is} hydrogen, Cχ-Cs-alkyl, unsubstituted or mono- to trisubstituted phenyl , wherein the substituents are selected from the group fluorine, chlorine, CH ₃ , CF ₃ , 0CH, 0CF ₂ H, nitro and cyano or pyridyl.

Compounds of the formula 1.6 are also preferred, where

X ^{1 is} oxygen, R ^{1 is} hydrogen or Cχ-C ₂ alkyl, R ² Cχ-C ₃ alkyl, R ³ Cχ-C ₂ alkyloxycarbonyl and R _# R ⁵ , R ⁶ , Q ¹ , Q ⁴ and Q ^{5 are} hydrogen mean Y ¹ and Y ² together form a chain = NN (R ⁹ ) -N = and R ^{9 is} Cχ-C ₄ -alkyl or unsubstituted or mono- to trisubstituted phenyl or unsubstituted or mono- or di-substituted benzyl, where the substituents are each selected from the group consisting of fluorine, chlorine, CH ₃ , CF ₃ , 0CH ₃ , 0CF ₂ H, nitro and cyano.

In particular, in view of their use, the compounds I compiled in the tables below are preferred. The groups mentioned for a substituent in the tables also represent a particularly preferred embodiment of the substituent in question, regardless of the combination in which they are mentioned. Table 1

Compounds of the general formula 1.1 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table 2

Compounds of the general formula 1.1 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table 3

Compounds of the general formula 1.1 in which R ^{1 is} CH ₃ and R ^{3 is} COOCH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table 4

Compounds of the general formula 1.1 in which R ^{1 is} CH ₃ and R ^{3 is} COOCHCH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table 5

Compounds of the general formula 1.1 in which R ^{1 is} CH ₂ CH ₃ and R ^{3 is} COOCH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table 6

Compounds of the general formula 1.1 in which R ^{1 is} CH ₂ CH ₃ and R ^{3 is} COOCHCH ₃ and the combination of the radicals Q ³ and R ² for each compound corresponds to one row of Table A.

Table A

Table 7

Compounds of the general formula 1.2 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table 8 Compounds of the general formula 1.2 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table 9

Compounds of the general formula 1.2 in which R ^{1 is} CH ₃ and R ^{3 is} COOCH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table 10

Compounds of the general formula 1.2 in which R ^{1 is} CH ₃ and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table 11

Compounds of the general formula 1.2 in which R ^{1 is} CH ₂ CH ₃ and R ^{3 is} COOCH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table 12

Compounds of the general formula 1.2 in which R ^{1 is} CHCH ₃ and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals R ^γ and R ² for a compound corresponds in each case to one line of Table B.

Table B

Table 13

Compounds of the general formula 1.3 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₃ and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C.

Table 14

Compounds of the general formula 1.3 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C.

Table 15

Compounds of the general formula 1.3 in which R ^{1 is} CH ₃ and R3 is COOCH ₃ and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C. Table 16

Compounds of the general formula 1. 3, in which R ^{1 is} CH ₃ and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C.

Table 17

Compounds of the general formula 1.3 in which R ^{1 is} CH ₂ CH ₃ and R ^{3 is} COOCH3 and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C.

Table 18

Compounds of the general formula 1.3 in which R ^{1 is} CH ₂ CH ₃ and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals G ¹ , G ² and R ² for a compound corresponds in each case to one line of Table C.

Table C.

Table 19

Compounds of the formula 1.4 in which R ¹ is hydrogen and R ³ is COOCH ₃ and the Korabination of T ^1, T ² and R ² corresponds for each compound corresponds to one line of Table D _1Q speaks

Table 20

Compounds of the general formula 1.4 in which R ^{1 is} hydrogen and R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals T ¹ , _c T ² and R ² for a compound corresponds in each case to one line of Table D.

Table 21

Compounds of the general formula 1.4 in which R ^{1 is} CH3 and ₂₀ R ^{3 is} COOCH ₃ and the combination of the radicals T ¹ , T ² and R ² for a compound corresponds in each case to one line of Table D.

Table 22

Compounds of the general formula 1.4 in which R ^{1 is} CH ₃ and _« , - R ^{3 is} COOCH ₂ CH ₃ and the combination of the radicals T ¹ , T ² and R ² for a compound corresponds in each case to one line of Table D.

Table 23

_C onnectivity of the general formula 1.4, in which R ¹ is CH ₂ CH ₃ and R ³ is COOCH ₃ and the combination of the radicals T ^1, T ² and R ² speaks for each compound corresponds to one line of Table D ent ^¬

Table 24

_C onnectivity of the general formula 1.4, in which R ¹ is CH ₂ CH ₃

35 and R ³ is COOCH ₂ CH ₃ and the combination of the radicals T ^1, T ² and R ² for a compound corresponds to one line of Table D ent ^¬ speaks

45 Table D

Table 25

Compounds of the general formula 1.5 in which R ^{1 is} hydrogen and R ^{2 is} CH ₃ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 26

Compounds of the general formula 1.5 in which R ^{1 is} hydrogen and R ^{2 is} CH ₂ CH ₃ and the combination of the radicals V and R ³ for a compound in each case corresponds to one row of Table E speaks

Table 27

Compounds of the general formula 1.5 in which R ^{1 is} hydrogen and R ^{2 is} (CH ₂ ) ₂ CH ₃ and the combination of the radicals V and R ³ for a compound corresponds in each case to one line of Table E.

Table 28 Compounds of the general formula 1.5 in which R ^{1 is} hydrogen and R ^{2 is} CH (CH ₃ ) ₂ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 29

Compounds of the general formula 1.5 in which R ^{1 is} CH ₃ and R ^{2 is} CH ₃ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 30

Compounds of the general formula 1.5 in which R ^{1 is} CH ₃ and R ^{2 is} CH ₂ CH ₃ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 31

Compounds of the general formula 1.5 in which R ^{1 is} CH ₃ and R ^{2 is} (CH ₂ ) CH ₃ and the combination of the radicals V and R ³ for a compound corresponds in each case to one line of Table E.

Table 32

Compounds of the general formula 1.5 in which R ^{1 is} CH ₃ and R ^{2 is} CH (CH ₃ ) ₂ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 33

Compounds of the general formula 1.5 in which R ^{1 is} CH ₂ CH ₃ and R ^{2 is} CH ₃ and the combination of the radicals V and R ³ for a compound corresponds in each case to one line of Table E.

Table 34

Compounds of the general formula 1.5 in which R ^{1 is} CH ₂ CH ₃ and R ^{2 is} CH ₂ CH ₃ and the combination of the radicals V and R ³ for each compound corresponds to one row of Table E.

Table 35

Compounds of the general formula 1.5 in which R ^{1 is} CH ₂ CH ₃ and R ^{2 is} (CH ₂ ) ₂ CH ₃ and the combination of the radicals V and R ³ corresponds to one row of Table E for a connection

Table 36

Compounds of the general formula 1.5 in which R ^{1 is} CH ₂ CH ₃ and R ^{2 is} CH (CH ₃ ) ₂ and the combination of the radicals V and R ³ 'for each compound corresponds to one row of Table E.

Table E

Table 37 Compounds of the general formula 1.6, in which R ^{1 is} hydrogen and R ^{2 is} CH ₃ and the combination of the radicals W and R ³ for one connection each corresponds to one row of table F.

Table 38

Compounds of the general formula 1.6 in which R ^{1 is} hydrogen and R ^{2 is} CH ₂ CH ₃ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 39 Compounds of the general formula 1.6, in which R ^{1 is} hydrogen and R ^{2 is} (CH2) 2CH ₃ and the combination of the radicals W and R ³ for each compound corresponds to one row of Table F.

Table 40

Compounds of the general formula 1.6 in which R ^{1 is} hydrogen and R ^{2 is} CH (CH ₃ ) ₂ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 41

Compounds of the general formula 1.6 in which R ^{1 is} CH ₃ and R ^{2 is} CH ₃ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 42

Compounds of the general formula 1.6 in which R ^{1 is} CH ₃ and R ^{2 is} CH ₂ CH ₃ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 43

Compounds of the general formula 1.6 in which R ^{1 is} CH ₃ and R ^{2 is} (CH ₂ ) ₂ CH ₃ and the combination of the radicals and R ³ for each compound corresponds to one row of Table F.

Table 44

Compounds of the general formula 1.6 in which R ^{1 is} CH ₃ and R ^{2 is} CH (CH ₃ ) ₂ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 45

Compounds of the general formula 1.6 in which R ^{1 is} CHCH ₃ and R ^{2 is} CH ₃ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 46

Compounds of the general formula 1.6 in which R ^{1 is} CH ₂ CH ₃ and R ^{2 stands} for CHCH ₃ and the combination of the radicals W and R ³ for a compound corresponds in each case to one line of Table F.

Table 47 Compounds of the general formula 1.6, in which R ^{1 is} CH ₂ CH ₃ and R ^{2 is} (CH ₂ ) ₂ CH ₃ and the combination of the radicals W and R ³ for each compound corresponds to one row of Table F.

Table 48 Compounds of the general formula 1.6, in which R ^{1 is} CHCH ₃ and R ^{2 is} CH (CH ₃ ) and the combination of the radicals W and R ³ for each compound corresponds to one row of Table F.

Table F

The compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidio ycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.

They are of particular importance for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, Beans, tomatoes, potatoes and squash, as well as on the seeds of these plants.

They are especially suitable for controlling the following plant health ^¬ units:

Alternaria species on vegetables and fruits,

Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and grapevines ^¬,

Cercospora arachidicola on peanuts,

Erysiphe cichoracearum and Sphaerotheca fuliginea wächsen to Kürbisge ^¬,

Erysiphe graminis (powdery mildew) on cereals,

Fusarium and Verticillium species on different plants,

Helminthosporium species on cereals,

Mycosphaerella species on bananas and peanuts,

Phytophthora infestans on potatoes and tomatoes,

Plasmopara viticola on vines,

Podosphaera leucotricha on apples,

Pseudocercosporella herpotrichoides on wheat and barley,

Pseudoperonospora species on hops and cucumbers,

Puccinia species on cereals,

Pyricularia oryzae on rice,

Rhizoctonia species on cotton, rice and lawn,

Septoria species in cereals,

Uncinula necator on vines,

Ustilago species on cereals and sugar cane, as well • Venturia species (scab) on apples and pears.

The compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.

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. The application can take place both before and after the infection of the materials, plants or seeds by the fungi.

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

Depending on the type of effect desired, the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per hectare.

In the case of seed treatment, amounts of active ingredient of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.

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 in the material protection are, 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 compounds of the formula I are also suitable for effectively combating animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests:

• insects from the order of the butterflies (Lepidoptera), for example Agrotis ypsilon, Agrotis segetu, Alabama argilla- cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Helithiothiotholesana, Grapholithaisotholesana, Grapholithiothebrana, Grapholithaisebroles, Helithiella virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, La bdina fiscellaria, Laphygma exigua, Leucoptera cof- feella, Leucoptera scitella, Lithocolletana- liaxia triaxia liaxia triaxia siaxia, liaocolletana blancostella blancostella blancostella blotoxia , Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculisia Plellaellaellaella pellaellaellaella pellaella pella , Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato-poea pityocampa, Tortrix viridana, Trichoplusia ni and Zeira- phera canadensis

Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruechus pisorum, Bruchus lentisu- losa, Byiscus , Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr- hynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgiferisisobutisis, histobis, histobellisis, epilachnis, varilobinisis, epilachnis, varilobinisis, epilachnis, varilobinisis, epilachnis, varilobin , Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californi- cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus cochleariae, Otiorrhynchus ovatus, Phaedon, Phyllotreta chrysocephala , Phyllophaga sp., Phyllopertha hortico la, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,

• Two-winged (Diptera), e.g. Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata,

Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi- piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fan- nia canicularis, Gasterophilus intestinalis, glipidisisisisisodisisisodisis, glossina misplantis, glossina metrisis, feminine equilibrium, glossina morphisis, glossina misplantis, glossina misoblus Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella hysophilia, Phomorbia, pegomya brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole-racea and Tipula paludosa, Thrips (Thysanoptera), for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

Dermatologist (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,

Bugs (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies

Plant suckers (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce-rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia picisacumaumolaisolapiaaciaacolaicausolaapiaolapiaacolaicausolaapiaolabiaapiaaciosaapiaaciaiaabiaapiaaciaapiaaciaapiaaciaapiaaciaapiaaciaiaapiaumapiaapiaapiaapiaumia Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pe phigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus ascalonicus, Rhaidalosaphapus, Rhaidalosaphapus, Rhaidalosaphapus, Rhaidalosaphapis Schizaphis graminum, Schizoneura lanuginosa, Trialurodes vaporariorum and Viteus vitifolii,

Termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,

Straight wing aircraft (Orthoptera), e.g. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini- pes, Melanoplus spretus, Nomadascocata americanana, Pericascacerana america, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus, • Arachnoidea such as arachnids (Acarina), eg Amblyomma america- num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Ixusususbicinusbum, Ialxxus trichonium, Hyalxxus trichoni me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabieus, Tetranychus cinnabarinus tawchychanyus tawchychanyus tawchychanyus tawchychanyus, Tetranych

• Nematodes such as root-bile nematodes, eg Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming Nematodes, for example Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf aphids, for example Belonolaimus longicaudatus, Dity- lenchus destructor, Ditylenchus dipsaci, Heliocotylenusususus, Rad- longicililinus- Longidilinilus- Longidilinilus- Longidilinilus- Longidilinus chus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenelenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The application rate of active ingredient for controlling animal pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.

The compounds I can be converted into the usual formulations, e.g. 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 compound according to the invention.

The formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as 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 (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite eyes and methyl cellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic sulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids so ^¬ as their alkali metal and alkaline earth salts, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxy lated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenylpolyglycol ether, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, methylglycol ester, lauryl cellulose ether, lauryl cellulose ether, lauryl cellulose ether

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.

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

Granules, for example coated granules, impregnated granules and homogeneous granules, can be produced 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, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium ^¬ niumphosphat, ammonium nitrate, urea and vegetable products such as grain flour, tree bark, wood and nutshell meal, cellulose powders and other solid carriers.

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 mol of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil (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. -Share 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 with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid and 10 parts by weight of the sodium salt

Lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel mixed well and ground 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. Parts of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. The solution share By pouring and finely Ver ^¬ in 100 000 wt. Parts by water gives an aqueous dispersion which contains 0.02 wt .-% of the active ingredient.

VIII.20 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid and 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel mixed well and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, old dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active substances according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water. To prepare emulsions, pastes or old dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. 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.

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.

Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active ingredients, 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.

In the use form as fungicides, the compositions according to the invention can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. When mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides, in many cases an enlargement of the fungicidal spectrum of action is obtained.

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain the possible combinations, but not to limit it:

• Sulfur, dithiocarbamates and their derivatives, such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc ethylenediamine bis-dithiocarbamate, tetramethyl hi-bis-dithiocarbamate, ), Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N '-propylene-bis-dithiocarbamate), N,' -polypropylene-bis- (thiocarbamoyl) disulfide;

Nitroderivate, such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-isopropyl carbonate, 5- Nitro-isophthalic acid-di-isopropyl ester; Heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0.0-diethyl-phthalimidophosphonothioate, 5-amino-l- [ bis- (dimethylamino) phosphinyl] -3-phenyl-l, 2,4-triazole, 2, 3-dicyano-l, 4-di-thioanthraquinone, 2-thio-l, 3-dithiolo [4, 5 -b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benz - i idazole, 2- (thiazolyl- (4)) -benzimidazole, N- (1, 1,2, 2-tetrachloroethylthio) tetrahydrophthalide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide, • N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl- sulfuric acid diamide, 5-ethoxy-3-trichloromethyl-l, 2,3-thiadiazole, 2-rhodanomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl- 5-isoxazolone, pyridine-2-thio-l-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiine,

2, 3-dihydro-5-carboxanilido-6-methyl-l, 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-l-

(2,2,2-richloroethyl) formamide, 1- (3,4-dichloroanilino) -1-forylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecyl-morpholine or its Salts, 2,6-dimethyl-N-cyclododecyl-morpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpro- pyl] -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- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolane -2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl-urea, 1 - (4-Chlorophenoxy) -3,3-dimethyl-l- (1H-l, 2,4-triazol-l-yl) -2-butanone, 1- (4-chlorophenoxy) -3.3 -dimethyl-l- (lH-l, 2,4-triazol-l-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) - oxiran-2-ylmethyl] -lH-l, 2,4-triazole, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidine-methanol, 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, • strobilurins such as methyl-E-methoxyimino- [α- (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- {2- [6- ( 2-cyanophenoxy) pyrimidin-4-yl oxy] phenyl } -3-methoxyacrylate, methyl-E-methoxyimino- [α- (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [α- (2, 5-dimethylphenoxy) -o-tolyl] -acetamide, Methyl E-2- {2- [2-trifluoromethylpyridyl-6-] oxyethyl] phenyl} 3-methoxyacrylate, (E, E) -methoxy ino {2- [1- (3-trifluoromethylphenyl ) -ethylideneaminooxymethyl] -phenyl} -acetic acid methyl ester, methyl-N- (2- {[1- (4-chlorophenyl) -lH-pyrazol-3-yl] oxymethyl} phenyl) N-methoxy-carbamate,

Anilinopyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (l-propynyl) pyrimidin-2-yl] aniline, N- [4-Me- thyl-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,

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'-methoxyace - tyl) -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-me- thyl-5-methoxymethyl-l, 3-oxazolidine-2,4-dione, 3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1, 2- dimethylcyclopropan-l, 2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] -acetamide, 1- [2- (2,4-dichlorophenyD-pentyl] -lH-l, 2,4 -triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl-l-methyl) -benzhydryl alcohol, N- (3-chloro-2, 6-dinitro-4-trifluoromethyl-phenyl) -5 -trifluoromethyl-3-chloro-2- a inopyridine, 1- ((bis- (4-fluorophenyl) methylsilyl) methyl) -1H-1,2 triazole.

synthesis Examples

The instructions given in the synthesis examples below were used with the 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

Preparation of 4- ({[3- (4-chlorophenoxy) phenyl] acetyl} amino) -1, 3-dimethyl-1H-pyrazole-5-carboxylic acid ethyl ester

To a solution of 0.91 g of 4-amino-1, 3-dimethyl-iH-pyrazole-5-carboxylic acid ethyl ester, 0.6 ml of pyridine and 50 mg of 4-dimethylamino pyridine in 20 ml of anhydrous. Dichloromethane, 1.4 g of 3- (4-chlorophenoxy) phenylacetic acid chloride were added dropwise and the mixture was stirred at 20-25 ° C. for about 1 day. After washing the reaction mixture with hydrochloric acid, water and sat. NaHC0 ₃ solution, drying and distilling off the solvent, the residue was digested in diethyl ether / pentane. 1.6 g (76%) of the title compound were thus obtained as white crystals with a melting point of 115 ° C.

Example 2

Preparation of 4 ({[4- (4-trifluoromethylphenoxy) phenyl] acetyl} amino) -1, 3-dimethyl-1H-pyrazole-5-carboxylic acid ethyl ester

To a solution of 2.7 g of 4-amino-l, 3-dimethyl-1H-pyrazole-5-carboxylic acid ethyl ester, 1.8 ml of pyridine and 100 mg of 4-dimethylaminopyridine in 50 ml of anhydrous. Dichloromethane was a solution of 4.7 g of 4- (4-trifluoromethylphenoxy) phenylacetic acid chloride in 20 ml waserfr. Dropped dichloromethane and stirred at 20-25 ° C for about 1 day. After washing the reaction mixture with hydrochloric acid, water and sat. NaHC0 ₃ ~ solution, drying and distilling off the solvent, the residue was by chromatography Silica gel (dichloromethane and dichloromethane / methanol 98: 2) cleaned. 3.1 g (45%) of the title compound were thus obtained as white crystals, mp. 144 ° C.

H

-Q

Table II

Table III

5x

Table IV

45

Examples of the action against harmful fungi

The fungicidal activity of the compounds of the general formula I was demonstrated by the following tests:

The active ingredients were separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® N (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight .-% Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) prepared and diluted with water according to the desired concentration.

Example of use 1 - Activity against Alternaria solani on tomatoes

Leaves of potted plants of the "Large meat tomato St. Pierre" were sprayed to runoff point with an aqueous suspension which was prepared from a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier. The following day, the leaves were infected with an aqueous zoospore suspension of Al ternaria solani in 2% biomalt solution with a density of 0.17 x 10 ⁶ spores / ml. / The plants were then placed in a steam-saturated chamber at 24 ° C. and then for 5 days in a greenhouse at temperatures between 20 and 22 ° C. After 5 days, the blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.

In this test, those with 63 ppm of the active ingredients 1-1, 1-2, 1-3 and 1-4 showed an infection of at most 20%, while the untreated plants were 80% infected.

Example of use 2 - effectiveness against Plasmopara vi ticola

Leaves of potted vines of the "Müller-Thurgau" variety were sprayed to runoff point with aqueous preparation of active compound, which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. In order to be able to assess the long-term effect of the substances, the plants were placed 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 humid chamber for 16 hours to accelerate the sporangia carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

In this test, the plants treated with 63 ppm of the active ingredient 1-5 showed no infection, while the untreated plants were 85% 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 Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) prepared and with the desired concentration with acetone in the case of a. or with water in the case of b. diluted.

At 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 controls (threshold of action or minimum concentration).

Claims

claims

1. acylated 4-aminopyrazoles of the formula I,

where A represents one of the following groups:

X ^ X ^ X ³ oxygen or sulfur;

R ^{1 is} hydrogen, Cχ-Cg-alkyl, Ci-Cg-haloalkyl, Cχ-Cg-alkoxy-Ci-Cg-alkyl or C ₃ -Cg-cycloalkyl;

R ² Cι-C ₆ -alkyl, C ₆ haloalkyl, Cι-Cg-alkoxy-Cι-Cg-al kyl or C ₃ -C ₆ cycloalkyl;

R ^{3 is} hydrogen, halogen, cyano, Ci-Cg-alkyl, -C-C ₆ haloalkyl, -C (= 0) -OR ^α or -C (= 0) - R ⁰ ^;

R ^α , Rß hydrogen or Ci-Cg-alkyl;

R ^{4 is} hydrogen, Ci-Cg-alkyl, C ₂ -Cg-cyanoalkyl, Ci-Cg-alk-oxycarbonyl-Cx-Cg-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -Cg-alkynyl or -C (= X ² ) -R ^a ;

R ^a Ci-Cg-Alko y, Ci-Cg-haloalkoxy, C ₂ -Cg-alkenyloxy, C ₂ -Cg-alkynyloxy, Ci-Cg-alkoxy-Ci-Cg-alkoxy, C ₃ -C ₆ -cycloalkoxy, Ci -Cg-alkylthio, -C (= 0) -NR ^α Rß;

Phenoxy or benzyloxy, where the ring systems can carry one to three substituents selected from the group halogen, Ci-Cg-alkyl and Ci-Cg-AΪ- koxy, Phenylthio, which can carry a substituent selected from the group halogen and Ci-Cg-alkyl.

R ⁵ , R ^{6 are} hydrogen, halogen or Ci-Cg-alkyl or R ⁵ and R ⁶ together with the carbon atom to which they are attached form a three- to six-membered ring;

Q ¹ , Q ² r Q ³ hydrogen, halogen, nitro, cyano, hydroxy, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Cι-C ₆ alkoxy, Ci-Cg-haloalkoxy, C ₂ -Cg-alkenyloxy, Ci-Cg-alkylcarbonyloxy, Ci-Cg-alkylthio, Ci-Cg-haloalkyl hio, -C (= 0) -R ^α , -C (= 0) -0R, Ci-Cg-haloalkoxycarbonyl, Ci-Cg-Alk- oxy-Ci-Cg-alkoxycarbonyl, C ₃ -Cg-cycloalkoxycarbonyl, Ci-Cg-alkylsulfinyl, Ci-Cg-alkylsulfonyl, -C (= 0) -NR ^f R9 <

C ₃ -Cg cycloalkyl,

I I

-C (R) -0-C (R ^c ) -C (R ^d ) -M-0, -C (R ^b ) = N-0-R ^e ,

Phenyl, phenoxy, benzyl, benzyloxy, phenylthio, 2-pyridinoxy, 4-pyridinoxy, 2-pyrimidinoxy, 4-pyrimidinoxy, the ring systems being one to three of the substituents selected from: Ci-Cg-alkylthio, Ci-Cg-alkylsulfinyl , Ci-Cg-alkylsulfonyl and Ci-Cg-alkylcarbonyl or the group R ^{γ can} carry, or

R is hydrogen or Ci-Cg-alkyl;

R ^c , R ^{d is} hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, -C-C ₆ alkoxy-Cι-Cg-alkyl, C ₂ -Cg alkenyl, C ₂ -C ₆ alkynyl, Ci-Cg Alkoxycarbonyl, C-Cg-alkenyloxy-Ci-Cg-alkyl,

Phenyl, phenyl-Ci-Cg-alkyl or phenoxy-Ci-Cg-alkyl, wherein the ring systems can carry one to three substituents selected from the group halogen, Ci-Cg-alkyl and Ci-Cg-alkoxy;

M CH ₂ or a direct bond; R ^e is hydrogen, Ci-Cg-alkyl, C ₂ -CG-Alkoxycarbo- nyl-Ci-Cg-alkyl, C ₃ -C ₆ alkenyl, C ₃ -CG-alkynyl or benzyl, where the aromatic ring one to three substituents selected from the group halogen, Ci-Cg-alkyl and Ci-Cg-alkoxy can wear;

R ^f , R9 are hydrogen, Ci-Cg-alkyl, C ₃ -C ₆ cycloalkyl, or

R ^f and R9 together form a chain - (CH) -, - (CH) ₅ - or -CH ₂ -CH ₂ -0-CH ₂ -CH ₂ -;

R ^γ halogen, hydroxy, nitro, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-C _ß -alkoxy or Ci-Cg-haloalkoxy;

Hydrogen, halogen, nitro, cyano, hydroxy, SH,

-SC ≡N, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkyl thio, Ci-Cg-haloalkyl thio, C ₂ -Cg-cyanoalkyl, Cι-Cg-alkoxy-Cι-Cg-alkyl, Carboxyl-Ci-Cg-alkyl, C ₂ -Cg-alkoxycarbonyl-Cι-Cg-alkyl, C -Cg-alkenyl,

C -Cg-alkynyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, R ^f R9 '-C (= 0) -R ^α , -C (= O) -0R ^α , -C (= 0) -NR ^f R9, -C (R ^α ) = N-0R ^h , Ci-Cg-alkylsulfinyl, Ci-Cg-alkylsulfonyl, C-Cg-cycloalkyl, Cs-Cg-cycloalkenyl or C ₃ -Cg-cycloalkoxy,

Phenyl, phenyl-Ci-Cg-alkyl, phenoxy, phenoxy-Ci-Cg-alkyl, phenyl-Ci-Cg-alkoxy, phenylthio, pyridyl, pyridyl-Ci-Cβ-alkyl, pyrazolyl, pyrazylyl-Ci Cg-alkyl, thienyl, thienyl-Ci-Cg-alkyl, thiazolyl, thiazolyl-Ci-Cg-alkyl, isoxazolyl or isoxazolyl-Ci-Cg-alkyl, wherein the ring systems can carry one to three groups R ^Y ;

R ^{h is} hydrogen, Ci-Cg-alkyl, C ₃ -Cg-alkenyl, C ₃ -Cg-alkynyl, C ₂ -Cg-alkoxycarbonyl-Cι-Cg-alkyl, or benzyl, which one to three substituents selected from the group halogen , Ci-Cg-alkyl and Ci-Cg-alkoxy can wear;

R ^ R ^ R ¹ " ^} hydrogen, -CC ₆ alkyl, Ci-Cg haloalkyl,

-C-Cg-alkoxy-Cι-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, Cι-C ₆ -alkylcarbonyl, -C (= 0) -OR ^α , -C (= 0) - NR ^f R5, -CC ₆ alkylsulfonyl, C ₃ -Cg cycloalkyl, Cs-Cg cycloalkenyl,

Phenyl or phenyl-Ci-Cg-alkyl, where the ring systems can carry one to three groups R ^Y ; Y ^X , Υ ² together form a chain = NN (R ⁹ ) -N = or

= NN (R ¹⁰ ) -C (R ^{1: L} ) =. wherein C (R ^{1: L} ) is in either position 3 or 4;

R ^{11 is} hydrogen, halogen, nitro, cyano, Ci-Cg-alkyl or Ci-Cg-haloalkyl;

Q ⁴ , Q ⁵ hydrogen, halogen, hydroxy, Ci-Cg-alkyl,

Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, phenoxy or benzyloxy, where the ring systems can carry one to three groups R ^r .

2. Compounds of formula I according to claim 1, wherein X ^{1 is} oxygen.

3. Compounds of formula I according to claim 1, wherein the variables have the following meaning:

χ!, X, X ³ oxygen;

R ^{1 is} hydrogen or Ci-Cg-alkyl;

R ² Ci-Cg-alkyl;

R ³ Ci-Cg-alkoxycarbonyl;

R ^{4 is} hydrogen;

R ⁵ , R ^{6 are} hydrogen, halogen or -CC ₆ alkyl;

Q ^{1 is} hydrogen;

Q ² , Q ³ hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy,

C ₂ -Cg-alkenyloxy, phenoxy, which can carry one to three substituents selected from R ^γ and Ci-Cg-alkylcarbonyl,

-C (R ^b ) -OC (R ^c ) -C (R ^d ) -M-0, or

Q ² and Q ³ together form a chain -0-C (R ⁷ ) = N-;

R ^{7 is} hydrogen, halogen, nitro, cyano, hydroxy, SH,

-SC≡N, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, C ₂ -Cg-cyanoalkyl, Cι-Cg-alkoxy-Cι-Cg-alkyl, carboxyl-Ci-Cg-alkyl,

C ₂ -Cg alkoxycarbonyl-Cι-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, NR ^f R ^< ?. -C (= 0) -R ^α , -C (= 0) -OR ^α , -C (= 0) -NR ^f R9, -C (R ^α ) = N-OR ^h , Ci-Cg-alkylsulfinyl, Ci -Cg alkylsulfonyl, C ₃ -Cg cycloalkyl, C ₅ -Cg cycloalkenyl or C ₃ -C ₆ cycloalkoxy,

Phenyl, phenyl-Ci-Cg-alkyl, phenoxy, phenoxy-Ci-Cg-alkyl, phenyl-Ci-Cg-alkoxy, phenylthio, pyridyl, pyridyl-Ci-Cg-alkyl, pyrazolyl, pyrazolyl-Ci Cg-alkyl, thienyl, thienyl-Ci-Cg-alkyl, thiazolyl, thiazolyl-Ci-Cg-alkyl, isoxazolyl or isoxazolyl-Ci-Cg-alkyl, wherein the ring systems one to three

Can carry groups R ^γ ;

R ^{h is} hydrogen, Ci-Cg-alkyl;

R ⁸ , R ⁹ , Rio hydrogen, Ci-Cg-alkyl, phenyl or benzyl, where the ring systems can carry one to three groups R ^γ ;

Y ^ Y ² together form a chain = NN (R ⁹ ) -N = or

= NN (R ¹⁰ ) -C (R ¹¹ ) =, where C (R ^{1: L} ) is in either position 3 or 4;

R ^{11 is} hydrogen or Ci-Cg-alkyl;

Q ⁴ , Q ^{5 are} hydrogen or halogen,

and R ^b , R ^c , R ^a , R ^e , R ^f , R9, M and R ^{γ have} the meaning given in claim 1.

4. Compounds of formula I according to claim 3, wherein the variables have the following meaning:

AA ¹ ;

R ⁵ , R ^{6 are} hydrogen;

Q ^{2 is} hydrogen or

Q ² forms together with Q ³ a chain -0-C (R ⁷ ) = N-;

Q ³ hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C ₂ -Cg-alkenyloxy or

Phenoxy, which can carry one to three groups R ^γ , r

-C (R ^b ) -0-C (R ^c ) -C (R ^d ) -M-0, or

Q ² and Q ³ together form a chain -0-C (R ⁷ ) = N-.

5. Compounds according to claim 4, wherein the variables have the following meaning:

Q ³ hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C ₂ -C ₆ alkenyl i oxy or phenoxy, which can carry one to three groups R ^y ,

I I

-C (R) -OC (R ^c ) -C (R ^d ) -M-0, or

Q ² and Q ³ together form a chain -0-C (R ⁷ ) = N-,

R ^c , R ^d hydrogen, Ci-Cg-alkyl, -C-Cg-alkoxy-Cι-Cg-alkyl, phenyl or phenoxy-Ci-Cg-alkyl, the ring systems selected from one to three substituents from the group halogen, Ci Cg-alkyl and Ci-Cg-alkoxy can wear;

M a direct bond;

R ^{e is} hydrogen or Ci-Cg-alkyl;

R ⁷ Ci-Cg-alkyl,

Phenyl, pyridyl or benzyl, where the ring systems can carry one to three groups R ^r ;

6. A process for the preparation of compounds of the formula I according to claim 1, in which X ^{1 is} oxygen and R ^{4 is} hydrogen, characterized in that 4-aminopyrazoles of the formula II,

where the variables R ¹ , R ² and R ^{3 have} the meaning given in formula I, with carboxylic acid derivatives of the formula III,

where the variables R ⁵ , R ⁶ and A have the meaning given for formula I and L stands for a nucleophilically displaceable leaving group.

7. Suitable for controlling animal pests or harmful fungi, comprising a solid or liquid carrier and a compound of the general formula I according to claims 1 to 5.

8. Use of the compounds I according to claims 1 to 5 for the preparation of an agent suitable for controlling animal pests or harmful fungi.

9. A method of combating harmful fungi, characterized in that the fungi or the materials, plants, the soil or seeds to be protected against fungal attack are treated with an effective amount of a compound of the general formula I according to claims 1 to 5.

10. A method for controlling animal pests, characterized in that the animal pests or the materials, plants, the soil or seeds to be protected from them are treated with an effective amount of a compound of the general formula I according to claims 1 to 5.

Acylated 4-aminopyrazoles

Summary

Acylated 4-aminopyrazoles of the formula I,

where A represents one of the following groups:

where # denotes the bond to -C (R ⁵ R ⁶ ) - and the variables have the meaning given in the description.

Process for the preparation of the compounds I, compositions containing them and their use for controlling animal pests and harmful fungi.