SU795436A3 - Fungicide composition - Google Patents

Abstract

1. Alpha-azolyl sulfides, sulfoxides and sulfones of the formula see diagramm : EP0000752,P35,F1 where R**1 denotes hydrogen, alkyl, alkoxycarbonyl, or unsubstituted or substituted aryl, R**2 denotes hydrogen or alkyl, R**3 denotes alkyl, alkenyl, alkynyl, unsubstituted or substituted phenyl, or unsubstituted or substituted aralkyl, Az denotes imidazol-1-yl, pyrazol-1-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, tetrazol-1-yl or tetrazol-2-yl, and n denotes one of the integers 0, 1 and 2, and their salts and metal complexes.

Description

N-AG mules, where AZ has the above value, if appropriate in the presence of a diluent. By oxidizing the thus obtained β -azolyl sulfides of the formula T (h o), o-azolyl sulphoxides of the formula T (Wi 1) and iOC-azolyl sulfones of the formula T (tl 2}) are obtained.

To obtain oi-azole sulfides of the formula T (p O), it is advisable (-Hlock sulfides of the formula TG without a diluent, or in the presence of one, to react with approximately 0.5-2 equivalents of an alkaline metal salt or approximately 0.5-4 equivalents a corresponding azole, if appropriate with the addition of 0.5-4 equivalents of base at temperatures of about 0200 0, preferably 20-1 ° C in a homogeneous or inhomogeneous medium.

The preparation of tert-butyl (2; 4-dichlorophenyl -1,2,4-triazol-1-yl-methyl sulfide is described below.

Compounds of general formula K (0) l

B-C - $ - R

Az

To a solution of 22.1 g of 1,2,4-triazole in 500 ml of anhydrous acetone, 60.5 g of tert-butyl-f (2,4-dichlorophenyl-J-chloromethyl-T-sulfide) are added. By the addition of 44.2 g of potassium carbonate as After stirring, the undissolved components are filtered, the filtrate is concentrated in vacuo to dryness, then 300 ml of water is added to the residue; the aqueous phase is extracted three times with 200 ml of methylene chloride, the combined extracts are washed with 200 ml of water, dried and concentrated in vacuo. Upon addition of 100 ml di 5 ropilovogo ester from residue was isolated 35.6 g (53%) of colorless crystals with m.p. 95-97 fc.

Similarly, compounds are obtained whose Q characteristics are listed in Table. one.

Table 1 I

7 C1

8 C1

9 C

88

 62-64

116-118

136-138

147

104-106

130 10tillci12 .ClH-K 13ClHEG 14Cl15Cl16 / L «Cl Cl I19 Cl 21Cl 22Cl 23Cl 24

 CH,

25-CHj-CH

CH,

Continued table. 1 V / O; V ciCH o ° C CH2-l c {eHj V 0

n. .

ABOUT

45-46; VocHj 116 3 198 GSU 57-58 i (Cll5) 3 95 "" iHjJa 125-128 70-88 101 82-84 b 110-112 148-150 VCl 162-163 3 95-97 Cl100-103

A mixture of tetrazole isomers

Mixture of diastereomers 4X4t Spectrum

Continued table. 1 Forms of application of various. Below are examples of various preparative forms of the active substance of the general formula T. In the examples, weight is often given, unless others are indicated. Example 1, 90 parts of compound 1 was mixed with 10 hours of M-methyl-β-pyrrolidone to obtain a solution suitable for use as the smallest droplets. Example 2 20 parts of the compound are dissolved in a mixture consisting of 80 parts of xylene, 10 hours, an addition product of 8-10 moles of ethylene oxide to 1 mole of oleic acid M-monoethanolamide, 5 parts of dodecylbenzenesulfonic acid calcium salt and 5 hours. an addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 hours. water and its dissolution in it gives an aqueous dispersion containing 0.02% by weight of the active substance. Example 3. 20 parts of the compound are dissolved in a mixture consisting of 40 parts of cyclohexanone, 30 parts of isobutanol, 20 parts of an addition product of 7 mol of ethylene oxide to 1 mol of isorctylphenol and 10 parts of an addition product of 40 mol of ethylene oxide to 1 mole of castor oil. BbuiHsaiftieN solution in 100,000 hours of water and thin. by dissolving it, an aqueous dispersion is obtained containing 0.02% by weight of the active substance. Example 4. 20 parts of the compound are dissolved in a mixture consisting of 25 parts of cyclohexanol, 65 parts of a mineral oil fraction with a boiling point. 210-280 and 10 parts of the product of the addition of 40 mol of ethylene oxide to 1 mol of castor oil. An aqueous dispersion containing 0.02% by weight of the active substance is obtained by pouring the solution into 00,000 parts of water and finely dissolving it. Example 5.20h. the compounds together with 3 parts of diisobutylnaphthalene-O-sulfonic acid sodium salt, 17 h of ligninsulfonic acid sodium salt from spent sulfite liquor and 60 parts of powdered silica gel are thoroughly mixed and crushed into a hammer mill. By finely distributing the mixture in 20,000 parts of water, a spray solution containing 0% by weight of the active substance is obtained,.

Example 6.3h Compounds 3 are thoroughly mixed with 97 parts of kaolin in the form of fine particles, thus obtaining a dust containing 3% by weight of 40 active substances.

Example 7. 30h. Compound 4 was thoroughly mixed with a mixture of 92 parts of powdered silica gel and 8 parts of paraffin oil sprayed onto the surface of this silica gel. Get the drug active substances good adhesion. Example B. 40 parts of the compound are thoroughly mixed with 1U of sodium condensate from phenolsulfonic acid-urea-formaldehyde, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. By diluting with water in an amount of 100,000 hours, an aqueous dispersion containing 0.04% by weight of the active substance is obtained. Example 9.20 parts of compound 2 Mix well with 2 parts of dodecylbenzenesulfonic acid calcium salt, 8 parts of fatty alcohol polyglycolic ether, 2 parts of phenol sulfate-formaldehyde sodium condensate and 68 parts of paraffinic mineral oil. Get a steady oil dispersion. The examples below illustrate the biological activity of the proposed compounds. PRI me R 11. Muffler dew barmen. Fillbecks Union barley sprouts grown in vegetation vessels sprayed with water pulses from 80% by weight of active ingredients and 20% by weight of emulsifier. After the emulsion dries, powdery powdery mildew spores (Erysiphe gram niSvaag. Horde) are sprayed. Experimental plants are then placed in greenhouse conditions at 20-22 ° C and 75-80% relative humidity. After 10 days, the degree of pest development is determined: O — no defeat, then in powers of up to 5 — complete defeat. For purposes of comparison, a known active substance of the formula O- is used: i2 fH- / 0-CH2-CH-CH2. The results are shown in Table. table 2

Continued table. 2

Continued table. 2

Claims (2)

The formula of the invention A fungicidal composition containing derivatives of azole as an active substance and a solid or liquid carrier, characterized in that, in order to enhance fungicidal activity, it contains compounds of the general formula 3S i ⁴ • in * (0) n -CS - ** '* where R ¹ - Cs-C-rakyl normal or isostructure, phenyl, phenyl, 40. substituted once or twice with chlorine, fluorophenyl), trifluoromethylphenyl; R ^ is hydrogen, R ³ is tert-butyl, phenyl, phenyl, 45 substituted with chlorine, methyl, methoxy, benzyl, substituted once or twice with chlorine, ethylene phenyl; Ar - imidazol-1-yl, pyrazol-1-yl, 5Q 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, tetrazol-1-yl or tetrazol-2-yl ; h, 0.1 or 2, in an amount of 3-90 weight:%. 26 0 5s Sources of information taken into account during examination 27 0 1. The patent of Germany No. 2063857, cl. C 07 D 233/60 off 1972 29th 0 40 (prototype). 2. USSR patent No. 664528, thirty 0 class A 01 N 9/22, published. 1979. VNIIIPI Order 9479/5 Circulation 709 Subscription Branch of PPP Patent, Uzhhorod, st. Project, 4 ~