DD200710A1 - FUNGICIDAL AGENTS - Google Patents

Abstract

The invention relates to new fungicidal agents. As active ingredient they contain 0,0-dialkyl- (1-hydroxy-1-phenyl-2-chloro-ethyl) -phosphonic acid ester of the general formula in which R = methyl or ethyl; R & ind1! = Hydrogen, chlorine, bromine, nitro, methyl or methoxy; R & ind2! = Hydrogen or chlorine and n = the numbers 1 or 2. formula

Description

-ι-

YlB CH3MIEK0MBINAT BITTERPSLD Bitterfeld ,. 1.9. 1981

2182 WP A 01 N / 233 025/2

Fungicidal agent Field of application of the invention

The agents according to the invention can be used to combat fungal diseases on crop plants.

Characteristic of the known technical solutions

It is known that to combat fungal diseases on plants to a large extent metal-organic compounds are used. In addition to the known organometallic compounds of the Äththylen-bis-dithiocarbaminsäure Maneb (US-PS 2504 · 404 and 2 × 10 822), Mancozeb (DE-PS 996 264, US-PS 2504 404) and Zineb (US-PS 2457 674), inorganic metal compounds as fungicides are still widely used today. The inorganic copper compounds are known to have the greatest practical importance for the control of fungal crabs in potato, tomato, vine and banana cultivation. Copper orsychloride, the most important representative of inorganic metal compounds, is used against late blight on tomatoes and potatoes, but it is disadvantageous that many organometallic compounds are not well tolerated by plants.

- 2 object of the invention;

233025 2

The aim of the invention is to develop new, effective phosphonic acid esters for combating fungal crys- tics on eggplant patches.

Explanation of the essence of the invention r

This object is achieved in that the fungicidal composition in addition to conventional adjuvants and iürägerstoffen as active compound compounds of the general formula

GHClE ₂

in the .. .

R s is methyl or ethyl

3L · = hydrogen, alkyl, methoxy, nitro, halogen,

Ep = hydrogen or chlorine and

η = the numbers 1 and 2 mean.

It has been found that the 0, O-dialkyl- (1-hydro 2-yl-4-phenyl-2-chloroethyl) -phosphonic esters, in addition to a good action against Alternaria tenuis, Betrytis cinerea and Fusarium culmorum especially very good fighting properties against Phytophthora infestans respectively. Compared to commercially available preparations, for example copper oxychlorides, the compositions according to the invention have a higher fungicidal activity against Phytophthora infestans and are better plant-tolerant than the finial preparations.

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The 0,0-dialkyl- (1-hydrosy-1-piperyl-2-clilor-ethyl) phosphoQ-acid esters may be prepared by reaction of dialkylphosphine with side-chain halogenated acetophenones in the presence of catalytic or aliphatic amounts of a BaBe _5, for example Trialkylamine. It is advantageous to carry out the reaction in inert solvents from which the phosphonic acid esters gradually precipitate as crystalline, white substances.

Analogously to the provisions 1 and 2, the 0.0-dialkyl- (1-hydroxy-1-phenyl-2-chloroethyl) -phosphonic acid esters listed in Table I can be prepared.

Regulation 1:

Preparation of the Q, 0-dimethyl- (1-hydroxy-1- (4-methylphenyl) -2-chloroethyl) -phosphonic acid ester (Compound 1)

A reaction solution of 16.9 g (0.1 mol) of OJ- chloro-4-methylacetophenone, 12.0 g (0.1 mol) dime my Ip hosph.it and 100 ml of benzene is added gradually with stirring with 10, 8 g (0.1 mol) of triethylamine, which separates out of the solution, a crystalline substance. The reaction solution is allowed to stand overnight. Thereafter, the precipitate is filtered off with suction, dried and washed with water. After recrystallization from n-heptane 22 g (79% of theory) of a crystalline white substance from 5p 161 to 162 ⁰ O are obtained.

Elemental analysis:

P 01

Calculated: 11.11 12.72

found: 10.95 12.60

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Regulation 2:. .

Preparation of OjO-Dimetbyl-Ci-hydroxy-i-C 1-6-chlorophenyl) -2-chloroethyl) -phosphonic Acid Ester (Compound 2)

To a reaction mixture of 18.9 g (0.1 mol) of OJ , 4-dichloroacetophenone, 100 ml of benzene and 11.5 S (0.1 mol) Dimethylphospn.it is added dropwise with stirring 2 g of triethylamine. The precipitate formed is filtered off with suction, dried, washed with water and dried. After recrystallization from n-heptane, 23 g (77% of theory) of a crystalline white powder of mp 14-3 to 14-6 ⁰ G are obtained.

Elemental analysis:

P 01

Calculated: 10.36 23.71

'found: 10,25 23,40

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2182

Table I: Compilation of fungicidal active compounds according to the invention

connection

Mp C ⁰ C)

Yield (% of theory)

GH

4-Br H 160 to 163 3,4-GH ₃ H 181 to 183 4-CH ₃ O H 138 to 142 4,5-Cl H 166 to 168 4-NO ₂ H 139 to 143 3-01 4-NO ₂ . H 137 to 143 3,4-Gl H. 120 to 122 4-01 H 115 to 117 4-NO ₂ H 137 to 143 4-Br Cl 166 to_ .168 4-Cl Cl 153 to 156

90.5

54

63 81

74.5 83

87.5

65

35.5

45

The active compounds according to the invention can be converted into emulsifiable concentrates, pastes, granules and wettable powders. The forms of application of the active compounds according to the invention are prepared by mixing the active compounds with extenders, where appropriate using surface-active substances, such as emulsifying and / or dispersing agents.

When water is used as an extender, organic solvents, for example, 2-ol, cyclohexanone, benzene, chlorobenzene, alcohol or dimethylformamide may also be used.

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Suitable solid extenders are minerals such as alumina, talc, kaolins, chalk or ground synthetic minerals, such as silicates and silicates.

Emulsifiers are non-ionic and anionic emulsifiers and used as dispersants Suifitablaugen and methylcellulose.

The active compounds are used in the form of their formulations or of solutions, emulsions, suspensions, pastes or granules prepared therefrom, by spraying, spraying or dusting.

The active ingredient data in the exemplary embodiments correspond to the information from Table I "

embodiments Example 1 :

In vitro test of the agents according to the invention

The test fungi are inoculated on agar plates containing drug concentrations of 0.1% by weight, 0.01% by weight, and 0.001% by weight. The growth of the fungi was scored after 12 days as follows:

1 = no growth inhibition

2 = weak growth inhibition

3 = strong growth inhibition

4 = complete growth inhibition

~~ & B O w K) £ n> ν w »

2182

Table II: effect against Alternaria tenuis culmorum , Botrytis cinerea and Eusarium Botrytis connection Conc. (%) Alternaria cinerea Pusarium (AS). tenuis 4 culmorum 1 0.1 4 4 4 0.01 4 4 4 0.001 1 4 1 δ ο, ι 4 4 4 0.01 4 4 1 0.001 1 , 4 1 10 0.1 * 4 4. 4 0.01 4 1 4 0.001 1 1

Example 2:

In vitro test against Phytophthora infestans

Tomato plants were treated with the corresponding active ingredient concentrations and, after the spray coating had dried on, were infected with the test fungus.

The incubation was carried out at 20 ⁰ G and 96. to 100% relative humidity and the evaluation on the 5th day.

The percentage of leaf infestation by the harmful fungus was recorded in credit notes:

1 = no control success

2 = low control success

3 = average control success

4 = good control success

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Table III: Control of Phytophthora infestans

connection Conc. (%) Boniturnote untreated and infected - m 1 Copper ero-chloride 0.1 0.01 4 2 1 0.1 0.01 4 3.3 2 0.1 0.01 4 1 3 0.1 0.01 4 4 4 0.1 0.01 4 4 5 0.1 0.01 4 4 6 0.1 0.01 4 1 12 0.1 0.01 4 4

Claims (1)

WP A 01 N / 233 025/2 233025 invention claim ! fungicidal agent, characterized in that it is in addition to conventional excipients and carriers as the active ingredient a compound of the general formula in the R = methyl or ethyl iL s is hydrogen, alkyl, methoxy, nitro or halogen R ₂ = hydrogen or Ohlor and η = the numbers 1 or 2, included.