DD149304A5 - SCHAEDLINGSBEKAEMPFUNGSMITTEL - Google Patents

Abstract

Compounds of the formula I in which R & exp1! Halogen, phenyl, C & ind 1-4 -alkyl, C & ind 1-4 -alkoxy, C & ind 1-3 -haloalkoxy, C 1-4 -alkylthio or the CF &sub3; X oxygen or sulfur; R & exp2! C 1-18 alkyl which is optionally substituted, C & ind2-8! -Alkenyl, C & ind2-6! -Alkynyl, C & sub3-8! -Cycloalkyl which is optionally substituted, phenyl which is optionally substituted, benzyl which is optionally substituted or an epoxide-containing alkyl radical having up to 4 C atoms; n is 0, 1, 2, or 3 and azole is the 1,2,4-triazol-1-yl radical or the 1,2,4-triazol-4-yl radical, where the compounds of the formula I are also in the form of their salts with inorganic or organic acids or as metal complex compounds, as well as a process for their preparation and their use as pesticides.

Description

Berlin, July 16, 1980 219 32 2 "I 'AP C 07 D / 219 322

56 973 12

Pesticides

Field of application of the invention

The invention relates to novel substituted by 1,2,4-triazole Hydratropasäurederivate, their preparation and their use as pesticides in crop protection.

Characteristic of the known technical solutions

Commercial crop protection agents are Benomyl, Tridemorph and Binapacryl. However, these compounds are used in fairly high amounts, partially phytotoxic and thus not always satisfactory.

Object of the invention

It is an object of the invention to overcome the disadvantages of the known compounds.

Explanation of the essence of the invention

The invention has for its object to provide new crop protection products based on 1,2,4-triazole substituted hydratropaic acid derivatives.

The new compounds have the general formula I,

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(I)

R is halogen, phenyl, C 1-10 -alkyl, C 1-10 -alkoxy, C 1-10 -alkoxy, C ₄ -haloalkoxy, C ₁ -t-alkylthio or the CF_ group,

X oxygen or sulfur,

RC ₁ o-alkyl, which is optionally substituted by halogen, C ₁ - alkoxy or by alkoxycarbonyl having up to 5 carbon atoms, or by dialkylamino having up to 8 carbon atoms, C ₀ - alkenyl, C ₀ _- Alkynyl, C, -Cycloalkyl, which is optionally substituted by C ₁ v-alkyl radicals. Phenyl which is optionally substituted by halogen atoms, C ₁ _ -alkyl radicals, C ₁ , -alkoxy radicals or the CF_-Gruppo, benzyl which is optionally substituted by halogen, or an alkyl radical containing the epoxy ring with up to 4 C atoms,

η β O, 1, 2 or 3 and

Azole the 1,2,4-triazol-1-yl radical - / N-N

or the 1,2,4-triazol-4-yl radical

mean.

The compounds of the F _o sleeves I may also be in the form of their salts with inorganic or organic acids or metal complex compounds, preferably complex compounds of copper are present, the latter in a usual V / else, for example - - 3 -

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from CuCl ₀ and compounds of the formula I can be obtained

In formula I, R is preferably halogen, in particular chlorine, X is oxygen, η is O or 1 and azole is the 1,2,4-triazol-1-yl radical.

The compounds of the formula I can be prepared by reacting compounds of the general formula II

1 '2 in which R, R, X and η have the meanings as in formula I and Hal is halogen, preferably chlorine or bromine, in particular chlorine, at higher temperatures, preferably between 60 and 120 C in the presence of a hydrogen halide-binding agent, preferably at least a stoichiometric or excess amount of an agent, for example a basic compound, such as. For example, potassium carbonate, sodium carbonate, triethylamine or N, N-Dimothylanilin either with at least 2 moles of 1,2,4-triazole per mole of the compound of formula II directly to the compounds of formula I, or at least one mole of 1,2,4 Triazole per mole of the compound of formula II first to the likewise new Monotriazolderivaten of formula III (see reaction Scheme 1). These reactions are advantageously carried out in inert organic solvents, such as. As acetone, acetonitrile, dimethylformamide or xylene by.

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Reaction Scheme 1

1,2,4-triazole

base

C-C-XR ^

Il

C h \ zol

(II)

(III)

The compounds of formula III are then either in the isolated state, or in the reaction mixture with at least one further mole of 1,2,4-triazole per mole of the compound of formula III with the addition of a catalytic excess of an inorganic or organic base, preferably triethylamine, at temperatures between 20 and 120 ^° C., preferably 60 to 100 ^° C., advantageously in organic solvents, according to reaction scheme 2 to give the compounds of the formula I according to the invention

Reaction scheme 2

H-C-XR '

(III)

(I)

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The two-stage reaction of the compounds of the formula II via the intermediate of the compounds of the formula III to give the compounds of the formula I may be advantageous in some cases, for. B. in such starting compounds of the formula II, whose direct, single-stage reaction leads only to unsatisfactory yields of compounds of formula I ·

The partially new precursors of formulas IV and V can, for. -B. according to Reaction Scheme 3 or 4 are obtained in the following way:

Reaction scheme 3

HCOOCH

OCH.

- C COOCH.

(IV)

This type of reaction is described in Liebigs Annalen der Chemie, 413 , 206 (1917).

According to Reaction Scheme 4, the products of Formula V are obtained by chlorination of the compounds of Formula IV. The chlorination with PCI, which proceeds in poor yields, is reported in Dtsch. Ehem. Ges. Jtt, 1368 (1918).

for η = 0 described. The extending with substantially better yields chlorination with ^p OCl, in dimethylformamide (DMF) is not yet described. Instead of POCl, or '

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PCI can be ζ. For example, it is also possible to use thionyl chloride, phosphorus trichloride or phosgene.

Reaction scheme 4

P0C1- / DMF

(IV)

(V)

Higher esters can be prepared from the Methyleetern of formula V by known methods by transesterification.

Another synthetic route for higher esters (Va) is outlined in Scheme 5.

Reaction scheme 5

^r n

- C COOCH

(IV)

PCI

(Va)

^rn + R ² OH

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The chlorination IV -. VI is for η = O in Ber. Dtsch · former Ges. 51, 1368 (1918).

The compounds of the formula I according to the invention are distinguished by an outstanding fungicidal action. Fungal pathogens already infiltrated into the plant tissue can be successfully combated successfully. This is particularly important and beneficial in those fungal diseases that can not be effectively controlled after infection with the usual fungicides. Pas Wirkungsspektrura the claimed compounds detected ζ. Especially next to Piricularia oryzae and various types of rust, especially powdery mildew fungi in fruit, vegetable, cereal and ornamental plant growing · Particularly noteworthy is the excellent effect of the compounds against mildews, which are resistant to benzimidazole derivatives (eg benomyl, carbendazim).

The compounds of the formula I are also suitable for use in the technical field, for example in wood preservatives, in the paint sector, all preservatives, for. B. in cooling lubricants for metalworking.

For the use in crop protection, the fungicidal verb indungen of formula I can be formulated as dusts ise, wettable powders, seed-dressing, dispersions, solutions, or emulsifiable concentrates in a conventional W _e. The content of active ingredients of the formula I is generally between 2 and 95 wt .-%, preferably 10 to 90 wt - . %, In addition, the active ingredient formulations mentioned optionally contain the usual juice, wetting, dispersing, emulsifying , Penetration, Solvent, Fill and

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- 8 carriers.

Also, mixtures or blends with other peptidic agents, such. As insecticides, acaricides, herbicides or fungicides and fertilizers or growth regulators may be possible.

AusfOhrunqsbeispiel

The invention is illustrated by the following examples.

A. PREPARATIONS for the Preparations

1) 2- (4-chlorophenyl) "- 3-chloroacrylic acid methyl ester

A mixture of 504 g (2.73 mol) of p-chloro-phenylacetic acid methyl ester, 164 g (2.73 mol) is added to a Natriuniusus3 tion prepared from 65.5 g (2.85 g-atom) of sodium and 800 ml of absolute toluene. Run methyl formate and 30 g of methanol so that the temperature does not rise above 40 ⁰ C. After completion of the feed is stirred for 4 hours at 40 C and 12 hours at room temperature. The precipitated Natriutasalz dee 2- (4-chlorophenyl) -3-hydroxyacrylic acid methyl ester is filtered off, washed with 200 ml of toluene, added to 3 1 of water and acidified with dilute sulfuric acid (pH 2). The 2- (4-chlorophenyl) -3-hydroxyacrylic acid methyl ester is extracted with methylene chloride, the extract is dried and concentrated. 516 g of a semicrystalline product are obtained, which is dissolved without further purification in 600 ml of absolute dimethylformamide. After dropwise addition of 430 g (2.8 mol) of phosphorus oxychloride at 25 ⁰ C is allowed

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Stirring for 1 hour and then heated to 110 ⁰ C for 1 hour. After cooling, poured 4 1 of ice water, extracted with methylene chloride, the extract is dried, the solvent is evaporated off and the residue is distilled off tAll · 406 g of 2- (4-chlorophenyl) 3-chloro-acrylic acid methyl ester, corresponding to a yield of 64.4 % of theory.

^K Pl, 8 mbar ¹²¹ ° ^C '* ⁿ f ¹ ^ ⁶¹⁵

2. 2-f4-chlorophenyl) -3-chloro-acrylic acid 3-propyl ether

115 g (0.5 mol) of methyl 2- (4-chlorophenyl) -3-chloroacrylate are refluxed with 108 g of isopropanol and 5.0 g of zirconium (IV) acetylacetonate for 8 hours. During this time, 300 ml of alcohol are distilled off and set off by fresh isopropanol. Thereafter, it is distilled under vacuum.

M _a n is obtained 78 g of 2- (4-chlorophenyl) -3-chloro-acrylic acid isopropyl ester · Kp from _Q ^ _MDAR ^{92 c un <n} ^ o ^ * ⁵³⁹⁵ * corresponding to a yield of 60.2% of theory.

3. 2 "(4" chlorophenyl) -3-chloro-acrylic acid 3-butyl-3-tert

115 g (0.5 mol) of 2- (4-chlorophenyl) -3-chloro-acrylic acid methyl ester are refluxed for 14 hours with 153 g of isobutanol and 4 g of p-toluene-3-sulphonic acid. During this time, 5 times 100 ml of alcohol are distilled off and replaced with fresh isobutanol. Thereafter, the reaction mixture is allowed to cool, the excess alcohol is taken off, the residue is taken up in methylene chloride, the solution is washed with water,

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it is dried, concentrated and distilled. 82 g of 2- (4-chlorophenyl) -3-chloro-acrylic acid isobutyl ester are obtained, corresponding to a yield of 60 % of theory.

mbar ^{115 bi3}

4. 3 »Chloro 2-phenyl-acrylic acid ethyl ester

With stirring at 40 to 45 C to a mixture of 140.8 g (0.733 mol) of ethyl 3-hydroxy-2-phenyl-acrylate and 53.5 g (0.735 mol) of dimethylformamide added dropwise 112.3 g (0.733 mol) Phsophoroxychlorid. Thereafter, 90 minutes at 105 ⁰ C is stirred. After cooling, the mixture is stirred into ice-water and the separated oil taken up with methylene chloride. After the neutral washing is dried and distilled. Ee 133.5 g of the main fraction of 3-chloro-2-phenylacrylic acid ethyl ester, bp 76 to 78 ⁰ C / 0.3 to 0.4 mbar; Yield: 86 % of theory.

5 x 3-hydroxy-2-phenyl'-acrylic acid ethyl esters

24 g of sodium (1.04 g-atom) are suspended in 500 ml of finely divided toluene. At 20 to 22 ⁰ C, a mixture of 164 g (1.0 mol) of ethyl phenylacetate and 74.1 g (l, o mol) of ethyl arsenic acid with stirring and ice water cooling within about 1 hour is added dropwise and stirred for 5 hours ·. After standing for 15 hours, another 1 hour at 45 ⁰ C is heated.

The reaction mixture is carefully mixed with 1 liter of Ei3 water. After phase separation, the aqueous phase is worked up by acidification with acetic acid,

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shake with methylene chloride, dry the methylene chloride extract and distill. Ee 140.8 g of 3-hydroxy-2-phenyl-acrylic acid ethyl ester, Kp _{0 4 m} b _ar ^{7Q Dis 79} ° ^C '* yield: 73.3 % of theory.

B. PREPARATION EXAMPLES Example 1

2- (4-chlorophenyl-3,3-bis (1,2,4-triazol-1-yl) -propionic acid ^ so per pyl ester

H-COOCH (CH).

25 g (0.069 mol) of 2- (4-chlorophenyl) -3- (l, 2,4-triazol-l- _3- yl) -acrylic acid isopropyl ester are mixed with 13.8 g (0.2 mol) of 1,2, 4-triazole in 100 ml of thiethylamine for 3 hours at 80 ⁰ C stirred. After cooling the reaction mixture, the solid P _r is oduct filtered off with suction, dried and times digested with 80 ml of toluene. 2 This gives 20 g of a colorless powder of 2- (4-chlorophenyl) -3,3-bis (l, 2,4-triazol-l-yl) propionic acid isopropyl ester of mp. 172 C, corresponding to a yield of 80 , 3 % of

theory • C 53 .26 3 ^H 17 ^C IN ₆ C 4th 75 M % t - '360 .8th % analysis • • C 53 .1 % i H 4, 5 %. N 23 .29 % calc .: (V / O *) H N 23 .0 Found .:

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Example 2

2 ~ phenyll-3,3-bis- (l, 2,4-triazol-1-yl) -propionic acid ester

CH-COOC ₂ H

• Κ

21.0 g (0.10 mol) of 3-chloro-2-phenyl-acrylic acid ethyl ether, 15.2 g (0.22 mol) of 1,2,4-triazole and 17.9 g (0.13 mol) of potassium carbonate in 100 ml of dimethylformamide for 4 hours at 82 ⁰ C gerührt.Dann 30 ml of triethylamine and additional 6.9 g (0.1 mol) of triazole was added and stirred for a further 4 hours at 80 C. The result is an orange-yellow suspension. After the solution has been suctioned off from the potassium salt, the main part of dimethylformamide is distilled off under reduced pressure, the residue is diluted with methyleneformamide and washed with VVaseer. After distilling off the methylene chloride, 35.8 g of pale yellow, crystalline residue are obtained from the dried methylene chloride solution. It is triturated with 70 ml of toluene, mixed with 70 ml of cyclohexyn and filtered with suction. There are obtained 20 g of crystalline, colorless product of 2-phenyl-3,3-bis (l, 2,4-triazoll-yl) -propionic acid ethyl ester, mp. 158 ⁰ C, corresponding to a yield of 64.1 % of theory ,

Analysis: ^c i ₅ ^H 16 ^N 6 ° 2 ^{M =} 312.3 calc .: C 57.68 %; H 5.16 %; N 26.91 % Found: C 57.70 %; H 4.90 %; N 26.60 %

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Example 3

2 '(4-Chlorphenvl) ~ 3 _t 3-bis (l _t 2 _t 4-triäzol-l-yl) -propionsgureisobutylester

Cl \ C)) CH-COOCH ₂ CH (CH ₃ ) ₂

29.8 g (0.091 mol) of crude 2- (4-chlorophenyl) -l, 2,4-triazole-.alpha-acrylic acid-isobutyl ether are mixed with 13.8 g (0.2 mol) of 1,2,4- Triazole in 100 ml of triethylamine for 3 hours at 80 ⁰ C roasted. After cooling, the reaction mixture is concentrated on a Rotavapor, the residue taken up in 800 ml of methylene chloride, the solution carefully washed with water, dried and concentrated. The crystalline residue is triturated with 200 ml of toluene / hexane = 1/1 and filtered off with suction. Ea remain 26.9 g of a colorless powder of 2- (4-chlorophenyl) -3,3-bis (1,2,4-triazol-1-yl) -propionic acid isobutyl ester, mp. 163-165 C, respectively a yield of 78.9 % of theory.

Analysis: ^{C H} i7 ig ^ClN 6 ° ^{M =} 2 ³⁷⁴ · ⁸¹ via _e: C 54.47%; H 5.07 %; N 22.43 % Found: C 54.10 %; H 5.10 %; N 22.20 %

Examples 4-39

In an analogous W _e ise Examples 4 to 10 and 18 to 22 are as described in Example 1 carried out while

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Examples 11 to 17 and 29 to 39 analogously to Example 2 and Examples 23 to 28 analogous to Example 3 except

1 leads. In Table 1, the radicals R and R and η in formula I of the compounds prepared according to Examples 4 to 39 from the corresponding compounds of formula II and their melting points are listed.

Table 1

Formula I:

example R ¹ η R ² Mp. No. ⁰ C 4 0 -CH ₃ 168-171 5 0 -CH ₂ CH ₂ CH ₃ 140-141 6 0 -CH (CH ₃ J ₂ 157 / 7 0 -PH ₂ J ₃ CH ₃ 141 8th 0 -CH ₂ CH (CH ₃ J ₂ 98-99 9 0 - (CH ₂ J ₄ CH ₃ 139-140 10 0 - (CH ₂ J ₂ CH (CH ₃ J ₂ 165 11 0 -CH ₂ CH-CH ₂ CH ₃ CH ₃ 145-146

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Example Λ R- η 2 , CuCIp 2 Mp. No. j O Z ⁰ Q 12 R * ² 191 0 -CH-CHgCH (CH ₃ ) g 13 0 CH ₃ 108 14 0 -PHg) ₅ CH ₃ 156 15 0 -CHg- ^) 146-147 16 -Chg-CH = CHg 172-173 4-Cl 1 -CH (CHg) ₂ CH ₃ 17 4-Cl 1 CH ₃ 186-189 18 4-CL 1 -CH ₃ 175 19 4-CL 1 - (CH 2) ₄ CH ₃ 156 20 4-Cl 1 - (CH 2) ₅ CH ₃ 187 21 4-Cl 1 - (CH ₃ ) ₃ CH ₃ . 156 22 4-Cl 1 -CH ₂ CH ₂ CH ₃ 207-208 23 4-Cl 1 -CHgCHgCH (CH ₃₎ g 182 24 4-Cl 1 -C ₂ H ₅ 198-200 25 4-Cl 1 -CH - tij # 207 26 4-Cl 1 "" Ω 221 27 -CH-CHgCH (CH ₃ ) g 217 0 -CH-CHgCHgCH ₃ 28 ^CH 3 / QS-CH-COOCH ₃ 251 4-Cl 1 - "" 29 -Chg-CH = CHg 158

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Example no. R ¹ 3-CF ₃ η R ² CH ₃ Schmelp. 30 4 3-CF ₃ 1 -C ₂ H ₅ 219 31 3-0CF ₂ CF ₂ H 1 -CH ₃ 137 32 2-Cl 1 153 33 2-Cl 1 -CH-C ₂ H ₅ 114 34 3,4-Cl ₂ 0 CH ₃ -CH ₃ 158 35 4-CH ₃ O 1 -C ₂ H ₅ 144-145 36 4-CH ₃ O 1 -CH ₃ 115-119 37 2 -CH ₃ 172-173 38 1 - ^C 2 ^H 5 184-186 39 1 142-146

C. Discussion Example A

A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert material and comminuting in a hammer mill

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Example B

A wettable powder readily dispersible in water is obtained by adding 25 parts by weight of active ingredient 64 parts by weight of kaolin-containing quartz as an inert substance 10 parts by weight of trisulphonic acid 3 potassium

and 1 part by weight of oleoylmethyltaurine sodium as wetting and dispersing agent

mixed and ground in a pin mill.

Example C

A readily dispersible dispersion of water in water is obtained by

20 parts by weight of active compound with 6 parts by weight of alkylphenol polyglycol ether

(Triton X 207) 3 parts by weight isotridecanol polyglycol ether

(8 Ae0) ⁺⁾ and 71 parts by weight of paraffinic mineral oil

(Boiling range, for example, about 255 to about 377 ⁰ C) and milled in a ball mill to a fineness of less than 5 microns.

Example D

The emulsifiable concentrate is obtained from 15 parts by weight of active ingredient

75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyäthylierte3 nonylphenol (10 AeO) ⁺ 'as an emulsifier.

♦) Number AeO = number of ethylene oxide units in the polyglycol ether

molecule

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D. BIOLOGICAL EXAMPLES

The letters A, B and C stand for the following commercial comparison means?

A: methyl 1- (butylcarbamoyl) -2-benzimidazole carbamate (benomyl)

B: N-Tridecyl-2 _# 6-dimethyl-morpholine (Tridemorph) C: 2- (sec-butyl) -4,6-dinitrophenyl (3-methyl-2-butenoate) (binapacryl).

Example I

Wheat plants are strongly inoculated in the 3-leaf stage with conidia of wheat powdery mildew (Erysiphe graminis) and placed in a greenhouse at 20 ⁰ C and a relative humidity of 90 to 95 % . 3 days after inoculation, the plants are sprayed to drip point with the compounds listed in Table I in the active compound concentrations of 500, 250, 125, 60, 30 and 15 mg / liter of spray. As a comparison, the comparison agent B is used in analogous W _e ise. After an incubation period of 10 days, the plants are examined for infestation with wheat powdery mildew. The degree of infestation is expressed in % of infected leaf area, based on untreated, infected control pests (= 100 % infestation). The result is summarized in Table I.

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Table I

Compound infected with wheat powdery mildew according to In % at mg active substance / liter spray mixture no.

500

250

125

60

15

0-3

5-10

0-3

0-3

0-3

Comparison means B

phytotoxic

15

25

raw hand.

infiz.

plants

100

Example II

Barley plants are strongly inoculated in the 3-leaf stage with conidia of the barley powdery mildew (Erysiphe graminis 3p. Hordei) and placed in a greenhouse at 20 ⁰ C and a relative humidity of 90 to 95 % . 3 days after inoculation, the plants are sprayed to drip point with the compounds listed in Table II in the active compound concentrations of 500, 250, 125, 60, 30 and 15 mg / liter of spray. On comparison, the comparison agent B is used in an analogous manner. After an incubation period of 10 days, the plants are examined for infestation with barley powdery mildew. The infestation

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degree is expressed in % of affected leaf fl ower, based on untreated, infected control plants (= 100 % infestation). The result is summarized in Table II.

Table II

Connection according to example no. with C in % 500 Jeratenta at mg W 250 Flour: active substance 125 fall / liter S 60 BlattfL pritzbr 30 area 15 100 17 O O O O O O 2 O O O O 0-3 3 7 O O O 0-3 5 3 O O O O 0-3 3-5 / comparisons B 3 3-5 5 5-10 15 jnbehand · Lnfiz. plants

Example III

Cucumber plants (variety Delikateß) are strongly inoculated in the 2-leaf stage with a conidia suspension of cucumber powdery mildew (erysiphe cichoracearum). After a drying time of Sporensusperi3ion of 30 minutes, the plants are placed in a greenhouse at 22 ⁰ C and 90 % relative humidity. 3 days after infection, the plants are sprayed to drip point with the compounds listed in Table III and drug concentrations. As a comparison, the comparison agent A is used in an analogous manner. After 10 days, the rating is done. The degree of infestation

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is expressed in % of infected leaf area, based on untreated, infected control plants (= 100 % infestation). The result i3t summarized in Table III.

Table III

Connection according to example no. with Gu in % b 500 mgmehlti egg mg .Virl 250 excepted substance / L 125 lene B3 iter Sf 60 Lattfl iritzbr 30 before the 15th 17 O O 0 0 0 0 5 O 0-3 3 5 15 2 O O 0-3 3 5 10 7 O 0-3 5 10 15 3 O O 0 0 3 Comparison means A 3 5 10 15 25 35 raw hand. infiz. plants 100

Example IV

Cucumber plants (variety Oelikateß) are strongly inoculated in a 2-leaf stadiuij ) with a conidia suspension of a Nenomyl-resistant cucumber powdery strain (Erysiphe cichoracearum). After a Antrocknurcpzöit the spore suspension of 30 minutes, the plants are placed in a greenhouse at 22 ⁰ C and up 90% relative humidity

-

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posed. 3 days after infection, the plants are sprayed to drip point with the compounds listed in Table IV and drug concentrations. As a comparison, the comparison agent A is used in an analogous manner · After 10 days, the Bonitur done. The degree of infestation is expressed in% of infected leaf area, relative to untreated, infected control plants (= 100 % infestation). The result is summarized in Table IV.

Table IV

Connection according to example no. with C Stamn mg VVi 500 iurkenmehlt j) infested material / Li 250 au (Benomy e leaf sprayer 125 l-re3 is before % broth 60 enter at 30 O 10 jnbehand. ,, Lnfiz. Plant ¹⁰ ° 17 0 0 O O O 5 0 0-3 3-5 5 15 5 2 0 0 3 3-5 5 100 7 0 0-3 5 10 15 3 0 0 0 O 3-5 Compensation A 35 60 100 100 100

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Claims (3)

* 16. 7. 1980 AP C 07 D / 219 322 219 322 Invention claim 1. Pesticides, characterized in that they have a content of 2 to 95 wt .-% of a compound of general formula I, CH-C-XR ² (I) azole wherein R is halogen, phenyl, C,. Alkyl, C _1-. -Alkoxy, C ₁ haloalkoxy, C _1-4 alkylthio or CF, group, X oxygen or sulfur, RC * "-alkyl which is optionally substituted by halogen, C" alkoxy or alkoxycarbonyl having up to 5 carbon atoms, _f or by dialkylamino radicals having up to 8 carbon atoms, C ₂ _ ₈ alkenyl, C ₂ _ _g "phenyl alkynyl, C, g-cycloalkyl, which is optionally substituted by C ^ .- alkyl optionally substituted by halogen atoms, C * --Alkylreste, C ₁ -alkoxy or CF - group is substituted. Benzyl, which is optionally substituted by halogen, or an epoxide-containing alkyl radical having up to 4 C atoms, η O, 1, 2 or 3 and -.NN azole the 1, 2,4-triazol-1-yl radical \\ _N / 219 322 _ ₂₄ _ or the 1,2,4-triazol-4-yl radical and their salts with inorganic or organic acids or their metal complex compounds as active ingredient and customary formulation auxiliaries. j2 · Use of compounds of the formula I according to item 1, characterized in that they are used for pest control in crop protection. Method for combating harmful fungi, characterized in that the surfaces and / or plants and / or substrates affected by them are brought into contact with a fungicidally effective amount of active compounds of the formula I according to points 1 and 2