EP1000037A1 - Pyrimidyl oxyphenylacetic acid derivatives - Google Patents

Abstract

The invention relates to novel pyrimidyl oxyphenylacetic acid derivatives, several methods for producing them, and to their use as fungicides. The invention also relates to novel intermediate products and a method for producing the same.

Description

Pyrimidyloxyphenylacetic acid derivatives

The invention relates to new pyrimidyloxyphenylacetic acid derivatives, several processes for their preparation and their use as fungicides, as well as new intermediates and a process for their production.

It has already been known that certain pyrimidyloxyphenylacetic acid derivatives, such as, for example, 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester, 2- ( Methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -2 - [[4- (2.2 , 2-tri- fluoro-1-methylethoxy) -2-pyrimidinyl] oxy] phenylacetic acid, methyl ester and 2- (methoxyimino) -N-methyl-2- [[4- (2, 2, 2-trifluoro-1 - methyl lethoxy) -2-pyrimidinyl] oxy] phenyl acetamide, which are constitutionally similar to those described below, have fungicidal properties (compare, for example, WO 95-24396 or EP 398692). The fungicidal activity of these compounds, however, leaves something to be desired, especially at low application rates.

The new pyrimidyloxyphenylacetic acid derivatives of the general formula (I) have now been found

in which

R stands for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, with the exception of 2,2,2-trifluoroethyl and l-methyl-2,2,2-trifluoroethyl, Q represents oxygen or -NH-, and

I_ 1, Lp-, iß and IJ * are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine

Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings

Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings

It was also found that the new pyπmidyloxyphenylacetic acid derivatives of the general formula (I) are obtained if (process a) 4-halo-2-phenoxypyrimidines of the general formula (II)

in which

Q, ß, ß, ß and ß have the meanings given above and

X represents halogen,

with an alcohol of the general formula

R-O-H (III),

in which

R has the meaning given above,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,

or if (process b) alkylsulfonylpyrimidines of the general formula (IV)

in which

R has the meaning given above and

R ^{1 represents} alkyl or arylalkyl,

with a 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivative of the general formula in which

Q, iΛ l L ³ and L ^{4 have} the meanings given above,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Finally, it was found that the new pyrimidyloxyphenylacetic acid derivatives of the general formula (I) show a very strong fungicidal activity.

Surprisingly, the substances according to the invention show a better fungicidal activity than 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester, 2- (methoxyimino) -N -methyl-2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoro-1 -methyl-ethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester and 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy ] -phenylacetamide, which are constitutionally similar, previously known active ingredients with the same direction of action.

The compounds of the invention can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, or optical isomers are present. Both the E and the Z isomers, the individual enantiomers, the racemates and any mixtures of these isomers are claimed.

Pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which R represents optionally up to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) alkyl with 4 to 12 carbon atoms substituted by halogen and / or 1 to 2 alkoxy groups having 1 to 8 carbon atoms,

Q stands for oxygen or -NH- and

Ll, iß, iß and L ^{4 are the} same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or

Alkylsulfonyl each having 1 to 6 carbon atoms, preferably for

Are hydrogen or methyl and especially hydrogen.

Also preferred are pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R for methyl which is optionally mono-, disubstituted or trisubstituted by halogen or optionally mono-, disubstituted, disubstituted, quadruplicate or pentavalent by halogen and / or 1 to 2 alkoxy groups having 1 to 8 carbon atoms, or optionally disubstituted by one, two, three or four times , fivefold, sixfold or sevenfold n-propyl substituted by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms or for optionally single, twofold, fourfold, fivefold, sixfold or sevenfold by halogen and / or 1 or 2 alkoxy groups with 1 to 8 carbon atoms substituted i-propyl,

Q stands for oxygen or -NH- and

ß, ß, ß and ß are the same or different and are independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, preferably hydrogen or methyl and in particular hydrogen.

Also preferred are pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms and / or 1 to 2 cycloalkyl groups with 3 to 6 carbon atoms (the in turn in turn optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl with 2 to 4 carbon atoms and 1 to 3 halogen atoms) or substituted alkenyl) Alkynyl having 2 to 12 carbon atoms,

Q stands for oxygen or -NH- and

iß, ß, iß and iß are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or

Alkylsulfonyl each having 1 to 6 carbon atoms, preferably for

Are hydrogen or methyl and especially hydrogen.

Also preferred are pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R represents cycloalkyl, cycloalkenyl which is optionally mono- to pentasubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl having 2 to 4 carbon atoms and 1 to 3 halogen atoms , Cycloalkylalkyl or cycloalkenylalkyl with 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl part and 1 to 4 carbon atoms in the alkyl part,

Q stands for oxygen or -NH- and

1.1, iß, ß xmά lß are the same or different and are independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms alkyl, alkoxy, alkylthio, alkylsulfinyl or

Alkylsulfonyl each having 1 to 6 carbon atoms, preferably hydrogen or methyl and in particular hydrogen.

Pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by fluorine, chlorine or bromine and / or n-, i-, s- or t- substituted once to twice by methoxy or ethoxy Butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3- , 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2nd - (2,3-dimethylbutyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl,

Q stands for oxygen or -NH- and

iß, iß, iß and iß are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluorifluoromethyl, difluorifluoromethyl, difluoromethyl, difluorifluoromethyl, difluoromethyl, difluoromethyl sulfonyl, preferably hydrogen or methyl and in particular hydrogen.

Pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R for methyl which is optionally mono-, disubstituted or trisubstituted by fluorine, chlorine or bromine or optionally mono-, disubstituted, in four, or five times by fluorine, chlorine, bromine and / or ethyl which is monosubstituted or disubstituted by methoxy or ethoxy, or optionally, monosubstituted or double , triple, quadruple, fivefold, sixfold or sevenfold by fluorine, chlorine, bromine and / or n-propyl substituted once or twice by methoxy or ethoxy or for optionally single, double, fourfold, fivefold, sixfold or sevenfold by fluorine, chlorine, bromine and / or i-propyl which is mono- to disubstituted by methoxy or ethoxy,

Q stands for oxygen or -NH- and

L *, L.2, L- and L ^{4 are} identical or different and are each independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethio, trifluoromifluoromethyl, trifluoromifluoromethyl, Trifluoromethylsulfinyl or trifluoromethylsulfonyl, preferably hydrogen or methyl and in particular hydrogen.

Pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which R represents allyl, but-2-en-1-yl, propargyl or but-2-in-1-yl which is optionally monosubstituted to n-fold, where the atoms and groups mentioned below are preferred as substituents: in each case 1 to n (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) fluorine, chlorine or bromine atoms, in each case 1 to 2

Methoxy or ethoxy groups and / or in each case 1 to 2 cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl groups, where the cycloalkyl groups mentioned are in each case optionally substituted once to five times by fluorine, chlorine, methyl or ethyl,

Q stands for oxygen or -NH- and

I_ I, ß, ß and L ^{4 are the} same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthioifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, especially trifluoromethyl, trifluoromethyl

Stand hydrogen.

Also particularly preferred are pyrimidyloxyphenylacetic acid derivatives of the formula (I) in which

R for single, double, triple, quadruple or quintuple if necessary

Fluorine, chlorine, bromine, methyl, ethyl, vinyl, allyl, trifluoromethyl, dimethylvinyl or dichlorovinyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl or cycloheptylmethyl cyclopropyl, cyclopropyl, cyclopropyl

Cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclopropenylmethyl, cyclobu- tenylmethyl, cyclopentenylmethyl, cyclohexenylmethyl or cycloheptenylmethyl,

Q stands for oxygen or -NH- and

I_l, iß, iß and L ^{4 are the} same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,

Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, preferably for hydrogen or methyl and in particular for hydrogen.

The general or residual definitions given above or in the preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

The radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.

Formula (II) provides a general definition of the 4-halo-2-phenoxypyrimidines required as starting materials for carrying out process a) according to the invention. In this formula (II), Q, β, ß, ß and ß preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Q, ß, ß, ß and ß were specified. X represents halogen, preferably chlorine. The 4-halo-2-phenoxypyrimidines of the formula (II) are not yet known; they are also the subject of the present application as new substances.

They are obtained (process c) if 4-halo-2-alkylsulfonylpyrimidines of the general formula (VI)

in which

X has the meaning given above and

R ^{2 represents} alkyl or arylalkyl,

with a 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivative of the general

Formula (V), optionally in the presence of a diluent and optionally in the presence of an acid acceptor.

Formula (VI) provides a general definition of the 4-halo-2-alkylsulfonylpyrimidines required as starting materials for carrying out process c) according to the invention. In this formula (VI), X preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for X in connection with the description of the intermediates of the formula (II) according to the invention. R ² represents alkyl or arylalkyl, preferably methyl or benzyl.

The 4-halo-2-alkylsulfonylpyrimidines of the formula (VI) are known and can be prepared by known processes (see, for example, Heterocycles (1985), 23 (3), 611-16). Formula (V) provides a general definition of the 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivatives which are further required as starting materials for carrying out process c) according to the invention. In this formula (V), Q, iß, L ² , iß and iß preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Q. , I_l, L ² , iß and iß were specified.

The 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivatives of the formula (V) are known and can be prepared by known processes (see, for example,

WO 95-24396 or GB 2249092).

Formula (III) provides a general definition of the alcohols required as starting materials for carrying out process a) according to the invention. In this formula (III), R preferably or in particular has those meanings which have already been stated as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention.

The alcohols of the formula (III) are known synthetic chemicals.

Formula (IV) provides a general definition of the alkylsulfonylpyrimidines required as starting materials for carrying out process b) according to the invention. In this formula (IV), R preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention. R ^Ϊ represents alkyl or arylalkyl, preferably methyl or benzyl.

The alkylsulfonylpyrimidines of the formula (IV) are known and can be prepared by known processes (compare, for example, WO 95-24396 or Chem. Ber., 101,

1968, 2132). The 3- (1-hydroxyphenyl-1-alkoximinomethyl) dioxazines required as starting materials for carrying out process b) according to the invention have already been described above in the description of process c) according to the invention.

Suitable diluents for carrying out processes a), b) and c) are all inert organic solvents. These preferably include ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;

Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides, such as dimethyl sulfoxide; or sulfones, such as sulfolane.

Processes a), b) and c) according to the invention are optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, amides, hydroxides, alcoholates, carbonates, hydrogen carbonates, and alkaline earth metal or alkali metal alkyl compounds, such as sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide,

Potassium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or butyllitium.

The reaction temperatures can be varied within a substantial range when carrying out processes a), b) and c). In general, temperatures from -20 ° C to 130 ° C, preferably at temperatures from -10 ° C to 80 ° C.

To carry out process a) according to the invention for the preparation of the compounds of the formula (I), 4-halo-2-phenoxypyrimidine of the formula are employed per mole

(II) generally 0.5 to 5 mol, preferably 0.8 to 2 mol of an alcohol of the formula (III). To carry out process b) according to the invention for the preparation of the compounds of the formula (I), 0.5 to 5 mol, preferably 0.8 to 2 mol, of a 2- (l-hydroxyphenyl-) are generally employed per mol of alkylsulfonylpyrimidine of the formula (IV). l-methoximino) acetic acid derivatives of the formula (V)

In order to carry out process c) according to the invention for the preparation of the compounds of the formula (II), in general 0.5 to 5 mol, preferably 0.8 to 2 mol of a second per mole of 4-halo-2-alkylsulfonylpyrimidine of the formula (VI) - (l-Hydroxyphenyl-l-methoximιno) acetic acid derivative of the formula (V)

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar

The reaction is carried out, worked up and isolated by the generally customary processes (see also the preparation examples).

The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria

Plant protection and material protection are used

Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes

Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteπaceae, Corynebacteπaceae and Streptomycetaceae

Some pathogens of fungal and bacterial are exemplary but not limiting

Diseases that fall under the generic names listed above Xanthomonas species, such as, for example, Xanthomonas campestπs pv oryzae,

Pseudomonas species, such as, for example, Pseudomonas syπngae pv lachrymans,

Erwinia species, such as, for example, Erwinia amylovora,

Pythium species, such as Pythium ultimum,

Phytophthora species, such as, for example, Phytophthora infestans,

Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or

Pseudoperonospora cubensis,

Plasmopara species, such as, for example, Plasmopara viticola,

Bremia species, such as, for example, Bremia lactucae,

Peronospora species, such as, for example, Peronospora pisi or P brassicae,

Erysiphe species, such as, for example, Erysiphe gramrnis,

Sphaerotheca species, such as, for example, Sphaerotheca fuhrinea,

Podosphaera species, such as, for example, Podosphaera leucotπcha,

Ventuπa species, such as, for example, Ventuπa inaequalis,

Pyrenophora species, such as, for example, Pyrenophora teres or P graminea

(Conidial form Drechslera, Syn Helminthospoπum), Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides. The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be particularly successful

Control of cereal diseases, such as against Erysiphe species, Leptosphaeria or Pyrenophora species, diseases in wine, fruit and vegetable cultivation, such as against Venturia, Podosphaera and Phytophtora species, use. Rice diseases, such as, for example, Pyricularia species, are also combated with good success.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.

Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV - Cold and warm fog formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfone oxide, as well as water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Possible solid carriers are: for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. Solid carrier materials for granules come into question: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and

Tobacco stem. Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: e.g. Lignin liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum mariabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and

Zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

Fungicides:

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,

Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cuffaneb, cymoxanil, cyphodaminazol, cypodamconazole, cypodinconol

Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo h, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole, Famoxadone, Fenapanil, Fenarimol, FenbuconazoL, Fenfüram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimol, Flusilazidol, Flusilazidol, Flusilazidol, Flusilazidol, Flusilazid, Flusilazid, Flusilazid Fosetyl sodium, fthalide, fuberidazole,

Furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,

Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,

Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,

Metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofürace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, Pefürazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifen, Pyifen, Pyroquilanil

Pyroxyf r, Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen,

Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin, Triticonazole,

Uniconazole,

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G,

OK-8705,

OK-8801,

α- (1,1-dimethylethyl) -ß- (2-phenoxyethyl) -1 H-1,2,4-triazole-1-ethanol,

α- (2,4-dichlorothenyl) -ß-fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol,

α- (2,4-dichloφhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1-ethanol,

α- (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-triazol-1-ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone, (E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

{2-Methyl- 1 - [[[1 - (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester

1 - (2,4-dichloφhenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) -oxime,

1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2, 5-dione,

l- (3,5-dichloro phhenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

l - [(diiodomethyl) sulfonyl] -4-methyl-benzene,

1 - [[2- (2,4-dichlorophenyl) -1, 3-dioxolan-2-yl] methyl] - 1H-imidazole,

1 - [[2- (4-Chlθφhenyl) -3-phenyloxiranyl] methyl] - 1 H- 1, 2,4-triazole,

1 - [1 - [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] - 1 H-imidazole,

1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6 ^, -dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-t-mazole-5-carboxanilide,

2,2-dichloro-N- [1 - (4-chloro-phenyl) ethyl] - 1-ethyl-3-methylcyclopropanecarboxamide,

2,6-dicrdor-5- (methylthio) -4-pyrirnidinyl-thiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,

2,6-DicUor-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole, 2 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -1, 3,4-thiadiazole,

2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] -arnino] -4-methoxy-lH-pyrrolo [2,3-d] pyridrid -5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) pentandinitrile,

2-Cuor-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,

2-phenylphenol (OPP),

3,4-dichloro-l- [4- (difluoromethoxy) phenyl] -IH-pyrrole-2,5-dione,

3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,

3 - (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile,

3- [2- (4-Chlθφhenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-Cuor-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -IH-imidazole-l-sulfonamide,

4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (1, 1-dimethylethyl) -N-ethyl-N-propyl-1, 4-dioxaspiro [4.5] decane-2-methanamine,

8-hydroxyquinoline sulfate, 9H-xanthene-9-carboxylic acid 2- [henylamino) carbonyl] hydrazide,

bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate,

Eis- 1 - (4-Chlθφhenyl) -2- (1 H- 1, 2,4-triazol-1 -yl) -cycloheptanol,

cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dύnethyl-moφholin hydrochloride,

Ethyl - [(4-chlθφhenyl) azo] cyanoacetate,

Potassium hydrogen carbonate,

Methane tetrathiol sodium salt,

Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate,

Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexane carboxamide.

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,

N- (2-Cuor-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,

N- (4-cyclohexylphenyl) -l, 4,5,6-tetrahydro-2-pyrirrddinamirι,

N- (4-hexylphenyl) - 1,4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,

N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,

N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,

N- [3-chloro-4,5-bis- (2-propynyloxy) phenyl] -N'-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,

O-methyl-S-phenyl-phenylpropylphosphoramidothioate,

S-methyl-1, 2,3-benzothiadiazole-7-carbothioate,

spiro [2H] - 1 -Benzopyran-2, 1 '(3 Η) -isobenzofüran] -3' -one,

Bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz,

Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, 4-bromo-2- (4-chloro-phenyl) - 1 - (ethoxymethyl) -5- (trifluoromethyl) - 1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chloπnephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanim , Chloφyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,

Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,

Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,

Lamda-cyhalothrin, Lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Peimethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymethosphos, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridlhrin, Pyridl Pyrethrum, Pyridaben, Pyrirnidifen, Pyriproxifen,

Quinalphos,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,

Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenhriazon, Tralomenhriazon, Tronomenhrononium,

Vamidothione, XMC, xylylcarb, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the

Inject active ingredient into the soil yourself. The seeds of the plants can also be treated. When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

Preparation Examples:

Example 1)

Procedure b)

To a solution of 1.1 g (0.005 mol) of 4-isopropoxy-2-methylsulfonylpyrimidine and

1.0 g (0.005 mol) of 2- (2-hydroxyphenyl) -2-methoxyimino-N-methylacetamide in 20 ml of dimethylformamide is added to 0.2 g (0.005 mol) of 80% sodium hydride suspension and stirred for 48 hours at room temperature. The mixture is taken up in ethyl acetate, washed twice with water, dried over sodium sulfate and concentrated under reduced pressure. 1.4 g (65% of theory) of 2- [2- (4-isopropoxypyrimidin-2-yloxy) phenyl] -2-methoxyimino-N-methylacetamide are obtained. HPLC: logP = 2.20

The logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0, 1% aqueous phosphoric acid)

Analogously to Example (1) and in accordance with the general description of the production processes a) and b) according to the invention, the compounds of the formula (I-a) according to the invention listed in Table 1 below are also obtained:

Table 1

Examples of use:

Example A

Erysiphe test (wheat) / curative

Solvent: 25 parts by weight of N, N-dimethylacetamide emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed

Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for curative activity, young plants with spores of Erysiphe graminis fsp. tritici pollinated. 48 hours after inoculation, the plants are treated with the

Sprayed drug preparation in the specified application rate.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds of preparation examples (3) and (129) show an efficiency of 100% compared to the untreated control at an exemplary application rate of active ingredient of 125 g / ha. Example B

Erysiphe test (barley) / protective

Solvent: 25 parts by weight of N, N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate.

After the spray coating has dried on, the plants are covered with spores of Erysiphe gra inis fsp. hordei pollinated.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds of preparation examples (3) and (129) show an efficiency of 100% compared to the untreated control at an exemplary application rate of active ingredient of 125 g / ha. Example C

Leptosphaeria nodorum test (wheat) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for curative activity, young plants are sprayed with a conidia suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours and are then sprayed with the active compound preparation in the stated application rate.

The plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of approx. 80%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, e.g. the compound of preparation example (1) at an exemplary application rate of active ingredient of 125 g / ha has an efficiency of more than 60% compared to the untreated control. In contrast, the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester, 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-tri-fluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro- l-methylethoxy) -2-pyrimidinyl] oxy] phenylacetamide under the same

Conditions only efficiencies between 0% and 18%. Example D

Pyrenophora teres test (barley) / curative

Solvent. 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration

To test for curative efficacy, young plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabin at 20.degree. C. and 100% relative atmospheric humidity for 48 hours. The plants are then sprayed with the Wukstoft preparation in the stated application rate

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no infection is observed

In this test, for example, the compound of preparation example (1) shows an efficiency of 70% compared to the untreated control at an exemplary application rate of active ingredient of 250 g / ha. In contrast, the known compounds achieve 2- (methoxyimino) -2 - [[ 4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] - phenylacetic acid, methyl ester, 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoroethoxy) -2 -pyrimidinyl] oxy] -phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoro-1-methylethoxy) -2-pyrimidinyl] oxy] -phenylacetic acid methyl ester and 2- (methoxy-imino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy] phenyl acetamide under the same conditions only efficiencies between 16%> and 25% Example E

Phytophthora test (tomato) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then in an incubation cabin at approx. 20 ° C and

100% relative humidity set up.

Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds of preparation examples (3) and (129) show an efficiency of at least 75% compared to the untreated control at an exemplary application rate of active ingredient of 100 g / ha. In contrast, the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester and 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-trifluoro-1-methylethoxy) -2-pyrimidinyl] oxy] phenylacetamide under the same conditions only efficiencies below 70%. Example F

Podosphaera test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the powdery mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 ° C. and a relative humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compound of preparation example (3) shows an efficiency of at least 80% at an exemplary application rate of active ingredient of 10 g / ha compared to the untreated control. In contrast, the known compounds achieve 2- (methoxyimino) -2 - [[4- (2,2,2-trifluoroethoxy) -2-pyrimidinyl] oxy] phenylacetic acid methyl ester, 2- (methoxyimino) -N-methyl-2- [[4- (2,2,2-tri-fluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide, 2- (methoxyimino) -2 - [[4- (2,2,2-tri-fluoro-l- methylethoxy) -2-pyrimidinyl] oxy] phenylacetic acid and 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy] -phenyl acetamide under the same conditions only efficiencies between 0 and 55%. Example G

Venturia test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of wixkstoff 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the scab pathogen Venturia inaequalis and then remain at about 20 ° C. for 1 day

100% relative humidity in an incubation cabin.

The plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.

Evaluation is carried out 12 days after the inoculation. 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, e.g. the compounds of preparation examples (3) and (129) at an exemplary application rate of active ingredient of 10 g / ha an efficiency of more than 90% compared to the untreated control. In contrast, the known compounds achieve 2- (methoxyimino) -N-methyl-2 - [[4- (2,2,2-tri-fluoroethoxy) -2-pyrimidinyl] oxy] phenylacetamide and 2- (methoxyimino) -N- methyl-2- [[4- (2,2,2-trifluoro-l-methylethoxy) -2-pyrimidinyl] oxy] phenylacetamide among the same

Conditions only efficiencies below 80%>.

Claims

claims

Pyrimidyloxyphenylacetic acid compounds of the general formula (I),

in which

R represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, 2,2,2-trifluoroethyl and 1-methyl-2,2,2-trifluoroethyl being excluded,

Q represents oxygen or -NH-, and

Ll, L ² , L ³ and iß are the same or different and each independently represents hydrogen, halogen, cyano, nitro, each optionally substituted by halogen substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl.

Compounds of formula (I) according to claim 1, in which

R represents optionally up to n-fold (where n represents the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) alkyl having 4 to 12 carbon atoms substituted by halogen and / or 1 to 2 alkoxy groups having 1 to 8 carbon atoms,

Q stands for oxygen or -NH- and L, L ² , iß and iß are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, preferably represent hydrogen or methyl and in particular hydrogen.

Compounds of formula (I) according to claim 1, in which

R for methyl which is optionally mono-, disubstituted or trisubstituted by halogen or optionally mono-, disubstituted, disubstituted, quadruple or pentahedral by ethyl and / or 1 to 2 alkoxy groups having 1 to 8 carbon atoms, or optionally disubstituted by one, two, three, four or four , fivefold, sixfold or sevenfold n-propyl substituted by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms or for optionally single, twofold, fourfold, fivefold, sixfold or sevenfold by halogen and / or 1 or 2 alkoxy groups with 1 to 8 carbon atoms substituted i-propyl,

Q stands for oxygen or -NH- and

Ll, L ² , iß and iß are the same or different and independently of one another in each case for hydrogen, halogen, cyano, nitro, in each case optionally substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms , preferably represent hydrogen or methyl and especially hydrogen.

Compounds of formula (I) according to claim 1, in which R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by halogen and / or 1 to 2 alkoxy groups with 1 to 8 carbon atoms and / or 1 to 2 cycloalkyl groups with 3 to 6 carbon atoms (the in turn, optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl with 2 to 4 carbon atoms and 1 to 3 halogen atoms) or substituted alkenyl) Alkynyl having 2 to 12 carbon atoms,

Q stands for oxygen or -NH- and

L, L ² , iß and iß are identical or different and independently of one another in each case for hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each optionally substituted by 1 to 5 halogen atoms, each having 1 to 6 carbon atoms , preferably represent hydrogen or methyl and especially hydrogen.

5. Compounds of formula (I) according to claim 1, in which

R for cycloalkyl optionally substituted up to five times by halogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or haloalkenyl having 2 to 4 carbon atoms and 1 to 3 halogen atoms , Cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl having 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl part and 1 to 4 carbon atoms in the alkyl part,

Q stands for oxygen or -NH- and L, L ² , iß and iß are the same or different and are each independently hydrogen, halogen, cyano, nitro, each optionally substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, preferably represent hydrogen or methyl and in particular hydrogen.

Compounds of formula (I) according to claim 1, in which

R for optionally single to n-fold (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) by fluorine, chlorine or bromine and / or n-, i-, s- or t- substituted once to twice by methoxy or ethoxy Butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3- ,

4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl,

Q stands for oxygen or -NH- and

L, L ² , ß and ß are the same or different and are each independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethyl, preferably hydrogen or methylifluoromethyl or trifluoromethyl.

7. Compounds of formula (I) according to claim 1, in which R for methyl which is optionally mono-, disubstituted or trisubstituted by fluorine, chlorine or bromine or optionally mono-, disubstituted, in four, four or five times by fluorine, chlorine, bromine and / or ethyl which is monosubstituted or disubstituted by methoxy or ethoxy, or optionally mono- or disubstituted by two , triple, quadruple, fivefold, sixfold or sevenfold by fluorine, chlorine, bromine and / or n-propyl substituted once or twice by methoxy or ethoxy or for optionally single, double, fourfold, fivefold, sixfold or sevenfold by fluorine, chlorine , Bromine and / or simply through twice

Methoxy or ethoxy substituted i-propyl,

Q stands for oxygen or -NH- and

L, L ² , iß and iß are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethormethylmethyl, difluoromethylfluorifluoromifluoromethyl, difluoromethylfluorifluoromifluoromifluoromethyl, difluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromethylfm preferably represent hydrogen or methyl and in particular hydrogen.

Compounds of formula (I) according to claim 1, in which

R for allyl, but-2-en-l-yl which is optionally monosubstituted to n-fold,

Propargyl or but-2-yn-l-yl, the following atoms and groups being preferred as substituents: 1 to n in each case (where n stands for the number of hydrogen atoms of the respective unsubstituted hydrocarbon radical) fluorine, chlorine - Or bromine atoms, each 1 to 2 methoxy or ethoxy groups and / or in each case 1 to 2 cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl groups, where the cycloalkyl groups mentioned are each optionally mono- to fivefold substituted by fluorine, chlorine, methyl or ethyl,

Q stands for oxygen or -NH- and

L, L ² , iß and iß are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, fluoromethoxy, trifluoroethyl, di-, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, tri fluoromethylsulfinyl or Trifluoromethylsulfonyl, preferably hydrogen or methyl and in particular hydrogen.

9. Compounds of formula (I) according to claim 1, in which

R for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropylmethyl, cyclobutylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclobutylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl, cyclohexylmethyl or cycloheptylmethyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclopropenylmethyl, cyclobutenylmethyl, cyclopentenylmethyl, cyclohexenylmethyl or cycloheptenylmethyl,

Q stands for oxygen or -NH- and L, L ² , iß and iß are the same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl,> methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, di- fluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl , preferably represent hydrogen or methyl and especially hydrogen.

10. Agent, characterized by a content of at least one compound of formula (I) according to claim 1.

1 1. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat.

12. Use of compounds of formula (I) or agents according to claims 1 to 10 for controlling pests. 0

13. A process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claims 1 to 9 are mixed with extenders and / or surface-active agents.

14. Process for the preparation of compounds of the formula (I), characterized in that (process a) 4-halo-2-phenoxypyrimidines of the general formula (II) in which

Q, L, L ² , ß and ß have the meanings given in claim 1 and

X represents halogen,

with an alcohol of the general formula

R-O-H (HI),

in which

R has the meaning given in claim 1,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,

or that (process b) alkylsulfonylpyrimidines of the general formula (IV)

in which

R has the meaning given in claim 1 and R ^{1 represents} alkyl or arylalkyl,

with a 2- (l-hydroxyphenyl-l-methoximino) acetic acid derivative of the general formula

in which

Q, L, L ² , ß and ß have the meanings given in claim,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.