JPS58174364A - Novel oxime derivatives, manufacture and plant germ repellent - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to compounds of the general formula l Hl -C-CB -R21 II R4 [wherein R1 is 2-halo, 4-halo or 2,4-dihalo-
represents phenyl, R2 is 6-pyridyl 1-oxide, 2-giradinyl 1
-oxide, 2-pyrazinyl 4-oxide or 2
-pyrazinyl 1,4-dioxide, R3 represents hydrogen or straight chain carbon, -alkyl, and R4 represents 00-6-alkyl, 03-6-cycloalkyl, 03-6-alkenyl or C3 - 6-alkynyl] compounds) and those compounds - initial acid addition field.

Compounds of formula I and their acid additions exhibit fungicidal properties (fu
ngicidal properties);
As fungicidal active substances, they are particularly suitable for use in industry and horticulture.

The invention also relates to processes for the preparation of compounds of formula I and their acid addition salts, compounds of formula I and their acid addition salts as fungicidal active substances, containing compounds of formula I or their acid addition salts as active substances. The present invention also relates to fungicidal compositions for controlling fungi in industry and horticulture.

The term "no-kuchi" in the definition of formula 1 includes fluorine, chlorine, bromine and iodine, with chlorine being preferred. or can be different.

II The terms "C1-6-alkyl", "C3-6-alkenyl" and "C3-6-alkynyl" include straight-chain as well as branched hydrocarbon radicals. Alkyl is understood to include, depending on the number of carbon atoms, for example the following groups: methyl, ethyl, n-protyl, iso-zorogyl, n-butyl, tart.

Butyl, isoamyl and n-hexyl.

When R4 represents 01-4-alkyl, 03-6-alkenyl or C3-6-alkynyl, it is preferably C-, -alkyl, C3- or C4-alkenyl,
Alternatively, it is C3- or C4-alkynyl. The allyl group is a preferred alkenyl group, and the propargyl group is a preferred alkynyl group.

R1 preferably represents 4-chlorophenyl or 2.4-dichlorophenyl, especially the latter group.

R3 preferably represents hydrogen, methyl or ethyl, especially hydrogen.

2t, 4'-dichloro-2-(5'-bilisol)-
Acetophenone O-methyloxime 1'-oxide is a particularly preferred compound of formula 1.

Other representative compounds of formula l are =2',
4'-dichloro-2-(3'-pyridyl)-acetophenone〇-ethyloxime 1'-oxide, 2', 4'-dichloro-2-(2'-2radinyl)
-Acetophenone O-methyloxime 1'-oxide, 2/, 4/-dichloro-2-(2'-pyrazinyl)
-Acetophenone O-methyloxime 4'-oxide, 4/-chloro-2-(5'-pyridyl)-acetophenone O-methyloxime 1'-oxide, 41-chloro-2-(2'-pyrazinyl)-acetophenone 0 -Methyl oxime 11, i, I-dioxide, 4'-chloro-2-(2'-pyrazinyl)-acetophenone 〇-ethyl oxime 11. , al-dioxide, 4'-chloro-2-(2'l?radinyl)-acetophenone○-allyloxime 4'-dioxide, 2', 4'-dichloro-2-(3'-pyridyl)-
Acetophenone O-allyl oxime 1'-oxide, 2'-chloro-2'-(2'-giradinyl)-acetophenone O-methyloxime 4'-oxide, 4'-fluoro-2-(2'-pyrazinyl)- Acetophenone 0
-Methyloxime 1'-oxide, 4'-zolomo2-(2'-pyrazinyl)-acetophenone O-methyloxime 1', 4'-dioxide, 4'-chloro-2-(2'-pyrazinyl)-pro Piophenone O-methyloxime 4'-oxide, 2',4-dichloro-2-(2'-2radinyl)-butyrophenone O-methyloxime 1',4'-dioxide, 2',4'-dichloro- 2-(2'-pyrazinyl)
-Acetophenone 0-allyl oxime 1'-oxide, 2', 4'-dichloro-2-(2'-giradinyl)
-Propiophenone O-methyloxime 11,4'l
-dioxide, 2', 4'-dichloro-2-(3'-gilydyl)-
Acetophenone O-cyclozologylunaxime 1'-oxide, 2', 4'-dichloro-2-(3'-pyridyl)-
'Acetophenone 0-inzorogylunaxime 1'-oxide, 2', 4'-dichloro-2-(3'-pyridyl)-
Acetophenone O-proparyloxime 1'-oxide, 4'-chloro-2-(2'-pyrazinyl)-acetophenone O-propargyloxime 4',-oxide, 2', 4'-dichloro-2-(2 '-pyrazinyl)
-acetophenone 0-deropaly lunaxime 1'-oxide, and 4'-iodo 2- (3'-giridyl)-acetophenone 0-cyclohexyl oxime 1'-oxime 1'-oxide) 11
．． 3 Geometric isomerism (E- and 2-isomers) arises due to the presence of C═N double bonds in compounds of formula 1.

In addition, because of the presence of asymmetric carbon atoms, compounds can exist as optical antipodes. Therefore, formula l is intended to include all of their possible isomeric forms.

As acid addition salts of the compounds of formula I, physiologically compatible salts with strong acids come into consideration. Preference is given herein to the salts of the compounds of formula I with inorganic acids such as hydrochloric acid, nitric acid and phosphoric acid and with sulfonic acids such as 1,5-naphthalene-disulfonic acid.

The process according to the invention for the preparation of compounds of formula l and their salts comprises (al general formula n 3 R1-C-C) (-R" 11 R4 [wherein R1% R3 and R4 are as indicated above) 1q-oxidation of the pyridine or pyrazine conductor of 3 RCCHRm 1 [wherein R1, R2 and R3 have the meanings shown above], a ketone of the general formula ■ R41ONI (2■ [wherein R41 represents C]~6-alkyl, 03-6-cycloalkyl or C3-6-alkenyl)] No〇－
It consists of reacting with a substituted hydroxylamine and, if desired, converting the resulting compound of general formula I into an acid addition salt.

Process variant fal may be conveniently carried out by oxidizing the starting material of formula (1) with hydrogen peroxide or peracid in the presence of an inert diluent.

When hydrogen peroxide is used as oxidizing agent, lower alkanols such as methanol, ethanol and isopropanol come into consideration as diluents, and the oxidation is preferably carried out from 0° to 60°C, especially from 20° to 40°C. carried out within a temperature range.

As peracids, preferably peracetic acid, perbenzoic acid and m
- Chloroperbenzoic acid is considered, and the oxidation is preferably carried out in a halogenated hydrocarbon (for example methylene chloride or chloroform) as diluent. The oxidation with peracids is preferably carried out in the temperature range from 0° C. to the reflux temperature of the reaction mixture, in particular from 0° C. to room temperature. A highly preferred embodiment of this process consists of carrying out the oxidation with m-chloroperbenzoic acid in chloroform in the temperature range from 0°C to room temperature.

A variant method leading to compounds of formula l denoting 3-6-cycloalkyl or C3-6-alkenyl (according to BL, the reaction is carried out in an organic solvent such as methanol or ethanol) The reaction is conveniently carried out in an alcohol, a bialkylamide such as dimethylformamide, or a tertiary amine such as pyridine.
The reaction is preferably carried out within a temperature range from room temperature to the reflux temperature of the reaction mixture. Since the starting materials of formula (1) are preferably used in the form of acid addition salts (eg hydrochloride or hydrogen sulfate), bases such as sodium or potassium carbonate, triethylamine or pyridine are expediently added to the reaction mixture.

For the preparation of acid addition salts, the compounds of formula I can, if desired, be reacted with the desired acid, such as hydrochloric acid, nitric acid, phosphoric acid or sulfonic acid.

Isolation and purification of the compounds of formula I and their acid addition salts thus produced are carried out according to methods known per se.

The starting material of the formula H is an oxime of the general formula ■ 3 R1-C-CH-R" V I H [wherein R1, R" and 'R3 have the meanings indicated above]. Reaction with a compound of R4U■ in which R4 has the meaning given above and U represents the group to be removed (e.g. chlorine, bromine, iodine, mesyloxy, tosyloxy or alkyl sulfate group) Alternatively, the ketone of the general formula ■ 3 RCCHR ■ 1 [wherein R1, R'' and R3 have the meanings shown above] is converted into the ketone of the general formula ■ R41ONH2N [wherein R41 is 00-6-alkyl, C3-6-cycloalkyl or 03-6-alkenyl] O-
It can be produced by reacting with substituted hydroxylamine.

The reaction of an oxime of formula V with a compound of formula ■ is carried out by treating the oxime of formula ■ with a compound of formula ■ in the presence of a base in an organic solvent within a temperature range from 0° C. to the reflux temperature of the reaction mixture. This can be conveniently done. Solvents can be protic or non-protic. When using protic solvents such as alcohols, especially methanol or ethanol, alkali metal hydroxides (eg sodium or potassium hydroxide) or alkali metal alcoholates are preferably used as bases. When using non-zolotic solvents, such as aliphatic or cycloaliphatic ethers, in particular tetrahydrofurano or dimethoxyethane, or dialkylamides, in particular dimethylformamyl, alkali metal hydrides (for example sodium hydride) are preferably used as bases. Ru. In a preferred embodiment of this process, sodium hydride is used as base and an aliphatic or cycloaliphatic ether, especially tetrahydrofuran or dimethoxyethane, or a dialkylamide, especially dimethylformamide, is used as solvent.

The reaction of the ketone of the formula (2) with the hydroxylamine of the formula (2), which is a compound of the general formula (1) representing R4-alkyl, 03-6-cycloalkyl or C3-6-alkenyl, can be carried out by the above modified method (bl This is conveniently done in a similar manner.

The starting material for the formula (■) is the ketone of the general formula (■) obtained by the above modified method (
It can be produced by N-oxidation in the same manner as al.
Ru.

The compounds of the formulas I'll', V, Vl and ■ which can be used as starting materials are either known or can be prepared according to methods known per se. for example,
Oximes of the formula V can be prepared from the corresponding ketones of the formula ■ by reaction with hydroxylamine, and the ketones themselves are described in German Patent Application No. 2.221.546, German Patent Publication No. 2,800.010. No. 2,01 and British Patent No. 2,01
No. 5,524, ie, for example, by condensing the corresponding methylated auracyclic compound with a halobinated benzoic acid ester.

The compounds according to the invention (i.e. the metals of formula I and their acid addition salts) have fungicidal activity.
activity) and therefore can be used to control fungi in agriculture and horticulture. They are particularly suitable for checking or eradicating the growth of plant pathogens on plant parts (e.g. leaves, stems, roots, rhizomes, fruits or flowers) and seeds, and at the same time preventing Botrytis cinerea (Botlytis cinerea).
rytis cinerae) [Grizzly mosquito e (
gray mold); powdery mildew fungus (powdew)
derymildew fungi), for example, Uncinula n.
ctor ) (grape vine povrder
y mildew)), Elisifi: I-e shi:
lff racearum (Erysiphe cichora)
cearum') [Cucurbit mildew], Podosphaera leucotricha (Podosphaera 1eu)
cotricha) [Linza powdery mildew] and Erysiphe graminis (Erysiphe graminis)
minig) [powdery mildew of cereals];
Inequal
is ) [app1e8Cab]; Helminthosporium oryzae (' Helminthosp
oriumoryzae) (rice brown spot disease ('br)
own 5potdisθa,se)]'.

and Puccinia, Uromyces, and Rhizoctonia.
ctonia), Penicillium (Pen1c"il'
It is particularly effective in controlling harmful fungi of the genera S. lium ), Sedetria and Csrcospora .

Individual representatives of the compounds according to the invention furthermore include wood-destroying fungi such as Coniophyla deteana (Con1ophora deteana).
ora puteana) and Gloeophyllum trabeum
) has remarkable activity against

The compounds according to the invention are distinguished by local and/or systemic activity.

The compounds according to the invention are active under greenhouse conditions even at concentrations of from 10 to 500 caps of active substance per 11 spray liquid. In the field, concentrations of from 501 to 2000 g of active substance of formula 1 per hectare and per treatment are advantageously used.

The compounds according to the present invention, i.e., the fungicidal active substances, can be prepared using formulation auxiliaries in the usual formulations, such as dusting powders, powders, granules, solutions, emulsions, suspensions, diluted concentrates, pastes, etc. Convert to Vine. The fungicidal composition according to the invention contains an effective amount of at least one acid addition salt of a compound of general formula 1 or of a compound such as 7 as defined above, and at the same time also as a formulation adjuvant. The compositions conveniently contain at least one of the following formulation auxiliaries: solid carrier materials; solvents or dispersion media; surfactants (wetting agents and emulsifiers)-dispersing agents (without surface-active action);
and stabilizers.

The following can basically be considered as solid carrier materials: natural inorganic substances such as kaolin, alumina, silica, talc, bentonite, chalk (for example white),
Magnesium carbonate, limestone, quartz, lomite, atapalite, montmorillonite and quartzite, combined inorganic substances such as bf, highly dispersed silicic acid, aluminum oxide and silicates; organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers such as phosphates and nodates; such carrier substances may even be present in the form of reso-granules or powders.

As solvents or dispersion media, those of the arrows come into consideration in principle; aromatic substances such as benzene, toluene, xylem/alkylnaphthalenes; chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzene,
chloroethylene and methylene chloride; aliphatic hydrocarbons such as cyclohexane and paraffins (e.g. petroleum fractions); alcohols such as butanol and glycols simultaneously their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; Polar solvents or dispersion media such as dimethylformamide, N-methylpyrrolidone, N-methylgyrrolidone and dimethylsulfoxide (such solvents or dispersion media preferably have a flash point of at least 5 Q °C and a flash point of at least 50 °C boiling point), and water. As solvents or dispersion media, so-called liquefied gas bulking agents or carrier substances may also be considered, which are substances that are gaseous at room temperature and normal pressure. Examples of such substances 11.111.1 are in particular aerosol propellants and halogenated hydrocarbons (
For example, dichlorodifluoromethane). When water is used as solvent, organic solvents can for example also be used as co-solvents.

Surfactants (wetting agents and emulsifiers) are nonionic compounds such as condensation products of fatty acids, fatty alcohols or fatty substituted phenols with ethylene oxide; fatty acid esters of sugars or polyhydric alcohols; products obtained by condensation of ethylene oxide with ethylene oxide; Zoroku polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.

Surfactants may also include anionic compounds such as soaps; fatty sulfate esters (such as sodium dodecyl sulfate, sodium octadecyl sulfate and sodium cetyl sulfate); alkyl sulfonates, arylsulfonates and fatty-aromatic sulfonates such as alkylbenzene sulfonates ( e.g. calcium dodecylbenzene sulfonate) approximately butylnaphthalene sulfonate; and more complex fatty sulfonates (e.g. the amide condensation product of oleic acid with N-methyltafrine and the sodium sulfonate of dioctyl succinate)
It can be.

Finally, surfactants can be cationic compounds such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.

As dispersing agents (without surface-active effect) the following are basically considered: lignin, sodium and ammonium salts of ligninsulfonic acids, sodium salts of maleic anhydride-diisobutylene copolymers, naphthalene and formaldehyde tonosulfone. oxidation & IJ condensation products and sulfite lye
.

Suitable dispersing agents as thickening agents or anti-sedimentation agents include, for example, methylcellulose, carbonyl dimethylcellulose, hydroxymethylcellulose, polyhinyl alcohol, alkali*, caseinate and blood albumin.

Examples of suitable stabilizers are acid binders (e.g. shrimp chlorophyllin, haenylcricidyl ether and soybean ester oxide); antioxidants (e.g. gallic acid esters and butyloxytoluene); UV-absorbers (e.g. substituted pent-phenones, diphenylacrylonitrile esters and cinnamate esters); and deactivating agents (e.g. salts of ethylenediaminotetraacetic acid and polyglycols).

The fungicidal composition according to the invention comprises, in addition to the active substance of formula I,
Other active substances may be contained, such as other fungicides, insecticides and acaricides, bactericides, plant growth regulators and fertilizers. Such combination compositions are suitable for broadening the spectrum of activity or for specifically influencing plant growth.

The fungicidal compositions according to the invention generally contain between 0.0001 and 95% by weight, depending on the type, of one or more compounds according to the invention as active substance. They may be in any form suitable for storage and transportation. In such forms (eg circulated concentrates) the active substance concentration is usually in the higher region of the above concentration range. The forms may be diluted with equal or different formulation auxiliaries to give active substance concentrations suitable for practical use, and such concentrations usually lie in the lower region of the above concentration ranges. Circulation concentrates generally contain from 5 to 95 parts by weight, preferably from 25 to 75 parts by weight, of one or more compounds of formula I. The form of use is inter alia, for example as a spray liquid in a suitable vehicle.
(dy-for-use) solutions, emulsions or suspensions come into consideration. In such 'X fog liquids, for example, concentrations from 0.0001 to 20 t% may be present. Ultra-Low -Vo method
In the lume process), a spray liquid with an active substance concentration of preferably from 0.5 to 20% can be formulated, while spray II liquid 1 can be prepared and applied in a low-volume method and a high-volume method, respectively. have

The fungicidal composition according to the invention may be prepared by mixing at least one Ibi compound of general formula I or an acid addition salt of such a compound with a formulation auxiliary.

The compositions are prepared in a known manner, for example by mixing the active substance with a solid carrier material in a suitable solvent or dispersion medium, using surfactants as wetting agents or emulsifying agents or dispersing agents, if necessary. Dissolution or suspension can be carried out by diluting a pre-adjusted Uramachi emulsion concentrate with a solvent or dispersion medium.

In the case of powder compositions, the active substance can be mixed with a solid carrier material (for example, by milling them together), or the solid carrier material can be seeded with a solution or suspension of the active substance and then mixed with a solvent or The dispersion medium may be removed by evaporation, heating or suction over vacuum. By adding surfactants or dispersing agents, such powder compositions can be rendered easily wettable with water so that they can be converted into suitable aqueous suspensions, for example as powder compositions. It can be done.

The compounds according to the invention may also be mixed with surfactants and solid carrier materials to form dispersible powders that are dispersible in water;
Alternatively, they may be mixed with a solid pregranulated phase material to provide the product in the form of jaws.

If desired, the compounds according to the invention may be dissolved in a water-immiscible solvent such as an alicyclic ketone, which conveniently contains a dissolved emulsifier so that the solution self-emulsifies on addition of water, and separately the active substance is can be mixed with an emulsifier, and the mixture is then diluted with water to achieve the desired result! I can give you 1 degree. Furthermore, the active substance can be dissolved in a solvent and the solution can then be mixed with an emulsifier. Such mixtures may similarly be diluted with water to give the desired concentration. In this way, circadian concentrates and ready-to-use emulsions are obtained.

The use of the composition according to the invention can be carried out according to the application methods customary in plant protection or agriculture, for example liquid spraying (s
prinkling), spraying
), dusting, pourin
g) and scattering)
It can be done with The method according to the invention for the control of fungi comprises treating the area to be kept (for example plants, plant parts or seeds) with an effective amount of a compound according to the invention or a composition according to the invention. The invention will now be illustrated by the following examples.

1. Preparation example 1 of active substance of formula l 2',4'-dichloro-2- in 100N chloroform
(5-tlysyl)-acetophenone. - A solution of 10 g of methyl oxime was added to a solution of 7 g of m-chloroperbenzoic acid at 0°C.
．． 2 g and the mixture was subsequently placed in a refrigerator at 4°C.
Store the mixture for 24 hours in chloroform.
diluted with 0U and 10% potassium carbonate solution 25ON
Extract with

The organic layer is dried over anhydrous sodium sulfate and concentrated. 2/, 4/-dichloro-2-(3
'-flysyl)-acetophenone o-methyloxime 1'-oxide is obtained as a mixture of E, Z isomers in the form of a yellowish paste.

In a similar manner, 2',4'-dichloro-2-(2-pyrazinyl) was prepared using m-chloroperbenzoic acid as the oxidizing agent.
Acidification of acetophenone 0-ethyl oxime gives the product, which is chromatographed with 2',4'-dichloro-
2-(2'-pyrazinyl)-acetophenone 0-ethyloxime 1'-oxide and 2',4'-dichloro-2-(2'-pyrazinyl)-acetophenone 0-ethyloxime 4'-oxide (viscous oil) and at the same time also 2', 4'-dichloro-2-(2'-pyrazinyl)-acetophenone 0-ethyloxime 1'.

It separates into 4'-dioxide (melting point 164-168°C).

Example 2 1.41 g of '2',4'-dichloro-2-(3'-pyridyl)-acetophenone 1'-oxide was evaporated with 5 ml of ethanol, and the solution was dissolved in 1 g of sodium carbonate and 0.0 g of O-methylhydroxylamine hydrochloride. .83S and the mixture is subsequently heated under reflux for 6 hours. The mixture is then poured onto ice and extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and subsequently concentrated. The residue is 2'.

It consists of 4'-dichloro-2-(5'nigiridyl)-acetophenone O-methyloxime 1'-oxide.

■, Starting material production example 6 2'',4'-dichloro-2-(6
After 4 hours, a solution of 13.3 g of acetophenone is treated with 10 g of sodium carbonate and 8.6 g of -methylhydroxylamine hydrochloride, and the mixture is subsequently heated to reflux temperature with stirring. Pour the mixture onto ice and extract with ethyl acetate. The organic layer was washed, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2'',4'-dichloro-2-(3-pyridyl)-acetophenone O-methyloxime, a mixture of E,z-isomers. It is obtained in the form of a yellowish oil.

In a similar manner, 2',4'-dichloro-2-(2-
2/,4/-dichloro-2-(2-pyrazinyl-)-acetophenone 0-ethyloxime is obtained from pyrazinyl)-acetophenone and 0-ethylhydroxylamine hydrochloride in the form of an oil.

Example 4 2',4'-dichloro-2 in chloroform 2OInt
-(5-g++dyl)-acetophenone 5g solution,
It is treated with 6.6 g of m-chloroperbenzoic acid at 0° C. and the mixture is subsequently stored in the refrigerator at about 4° C. for 24 hours.

The mixture is then diluted with 100 WLt of chloroform and extracted with 100 l of 10% potassium carbonate solution. The organic layer is dried over anhydrous sulfuric acid and concentrated. 2/, 4/-dicoo-2-(3'-pyridyl)-acetophenone 1'-oxide (melting point 137-1
40°C) is obtained.

Example 5 A mixture of 27.6 g of ethyl 2,4-dichlorobent) and 20.819 of ethyl 6-pyridyl acetate is treated in small portions with 10.59.9 of sodium methyl 2) at 20-25°C. do. The mixture is subsequently heated to 65-70° C. and the easily volatile products formed are removed with dry nitrogen. After 20 hours, the mixture is treated with concentrated hydrochloric acid 401 and heated at reflux temperature for 18 hours. The mixture is washed with diethyl ether and the aqueous layer is made basic by addition of concentrated ammonia and then extracted with methylene chloride. The organic layer was concentrated and the crude product was purified on silica del with methylene chloride/methanol (9
8:2). Generate? ! +2', 4
'-Cycloro-2-(6-gyridyl)-acetophenone can be crystallized from diethyl ether/n-pentane and melts at 55-56°C.

■, Formulation Example 6 1. Spray powder (for liquids or active substances that melt at below 75°C) Parts by weight Active substance of formula l 50 hydrated silicic acid 67 kaolin
5 Alkylphenol ethoxylate 4 Sodium polynaphthalene sulfonate 40
0 The liquid or molten active substance is taken up on the silicic acid, the remaining ingredients are mixed and the mixture is finally ground in a suitable mill.

2. Spray powder (for solid active substances that melt above 75°C) Parts by weight Active substance of formula l 50 Hydrated silicic acid 5 Kaolin
42 Sodium lauryl MCe 1 Sodium lignosulfonate
The 200 ingredients are mixed together and the mixture is finally ground in a suitable mill.

Example 7 Condensation concentrate (for active substance liquid at 20-25°C) Parts by weight Active substance of formula 1 500 Castor oil ethoxylate 100 r Calcium decylbenzenesulfonate 25C 0° - Appropriate amount of a mixture of alkylbenzenes Total amount 1000 parts by volume Ingredients Mixed with each other until a clear bath liquid was obtained.

Agent Asamura Hao 4 other people

Claims (1)

[Claims] (1) General formula l 3 R4 [wherein R is 2-halo, 4-halo or 2,4-dihalo-
represents phenyl, R2 is 6-pyridyl 1-oxide, 2-pyrazinyl 1
-oxide, 2-pyrazinyl 4-oxide or 2
-pyrazinyl 1,4-dioxide, R3 represents hydrogen or linear C1-4-alkyl, and R4 represents C1-6-alkyl, 03-6-cycloalkyl, C! ! -6-alkenyl or C3-6-alkynyl] and acid addition salts of these compounds. +21 Compounds according to claim 1, wherein R1 represents 4-chlorophenyl or 2,4-dichlorophenyl. +3) Compounds according to claim 1 or 2, wherein R3 represents hydrogen. +4) A compound according to claim 1 which is 2',4'-dichloro-2-(3'-pyridyl)-acetophenone o-methyloxime 1'-oxide. (5) Compounds according to claim 1 selected from: 2', 4'-dichloro-2-(2'-pyrazinyl)
-acetophenone 0-ethyloxime 1'-oxyr
1 2', 4'-dichloro-2-(2'-pyrazinyl)
-acetophenone 0-ethyloxime 4'-oxide, and 2',4'-dichloro-2-(2'-pyrazinyl)-acetophenone 0-ethyloxime 1',4'-dioxide. (6) Compounds or acid addition salts according to any one of claims 1 to 5 as fungicidally active substances. (7) General formula l 3 RCCHR1 1 R4 [In the formula, B1 represents 2-halo, 4-)-rho or 2,4-dihalo-phenyl, and R2 represents 6-pyridyl 1-oxide, 2-pyrazinyl 1
-oxide, 2-pyrazinyl 4-oxide or 2
- pyrazinyl 1,4-dioxide, R3 represents hydrogen or linear Cel4-alkyl, and R1': IC-6-alkyl, 05-6-cycloalkyl, 03-6-alkenyl or 03-6-alkynyl] or an effective amount of at least one such compound, as well as a formulation auxiliary. +8) 2',4'-dichloro-2-(3'-giridyl)
- A fungicidal composition according to claim 7, characterized in that an effective amount of acetophenone 0-methyloxime 1'-oxide and at the same time also a formulation auxiliary. (9) General formula l 3 R1-C-CH-R21 1 R4 [wherein R1 is 2-halo, 4-halo or 2,4-dihalo-
represents phenyl, R2 is 6-pyridyl 1-oxide, 2-pyrazinyl 1
-oxide, 2-2radinyl 4-oxa'. or 2-pyrazinyl 1,4-dioxide, R3 represents hydrogen or straight chain C1-dialkyl, and R4 represents c1-6-alkyl, 03-6-cycloalkyl, C5-6-alkenyl or C3-6-alkynyl] and their acid addition salts, (al General formula ■ 3 1 R4 [wherein Hl, R3 and R4 have the meanings indicated above in the scope of this patent claim. and R2/ represents 3-bilisol or 2-pyrazinyl] or by N-oxidizing the Schiff or pyrazine visiting conductor, or (bl general formula ■ 3 RCCHRII1 1 [wherein R1, R2 and R3 are A ketone of the general formula % [having the meaning given above in the scope of the claims] [wherein R41 is C~6-alkyl, C!!~6-cycloalkyl or 03~6-alkenyl] 0 of]
= A process consisting of reacting with a substituted hydroxylamine and, if desired, converting the compound of general formula I obtained into an acid addition salt. Uα The site to be latched is covered with an effective lid of at least one of the compounds according to claims 1 to 5 or the composition according to claims 7 or 8. A method for controlling fungi in agriculture and horticulture, consisting of treatment. 0υ Use of one of the compounds according to claims 1 to 5 or the compositions according to claims 7 or 8 for the control of fungi in agriculture and horticulture. (1) Compounds of formula I insofar as they are produced by the process according to claim 9.