JP2000119236A - Noxious organism-controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having bactericidal, acaricidal and insecticidal properties and useful as an active component in agricultural, horticultural and hygienic fields. SOLUTION: This noxious organism-controlling agent is a compound of formula I [X is CH; Y is OR11 (R11 is a 1-4C alkyl); A is oxygen atom or the like; R1 is a 1-4C alkyl, a halo 1-4C alkyl, cyclopropyl or the like; R2 is H, a 1-6C alkyl, or the like; R3 is H, a 1-6C alkyl, a 1-6C haloalkyl having 1-5 halogen atoms or the like], e.g. methyl-3-methoxy-2-[([(3-hydroxyimino-2-butyl) imino]oxy)o-tolyl]acrylate. In the compound of the formula I, a compound in which R3 is not H, is obtained by reacting an oxime of formula III with a benzyl derivative of formula IV (U is a leaving group) in an inert solvent, in the presence of a base and in the presence (absence) of a transition catalyst between phases at 0-50 deg.C. The compound of the formula I is effective e.g. for a plant pathogenic microorganism, especially a mold.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to novel pesticidal compounds represented by the following formula I and possible isomers and mixtures of isomers:

Embedded image Wherein a) X represents an N atom and Y represents OR ₁₁ or N (R ₁₂ ) R ₁₃ , or b) X represents CH and Y represents OR ₁₁ And further wherein, in the formula, R ₁₁ represents an alkyl group having 1 to 4 carbon atoms;
R ₁₂ and R ₁₃ independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; A represents an O atom or a group:
It represents NR _4; R ₁ represents a hydrogen atom, C 1 -C 4
R ₂ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 4 carbon atoms, a cyclopropyl group, a cyano group or a methylthio group; A cycloalkyl group of 6,

Embedded image Or a thienyl group; the D groups are the same or different,
Halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 2 carbon atoms, haloalkoxy group having 1 to 2 carbon atoms, 3 to 6 carbon atoms An alkenyloxy group, an alkynyloxy group having 3 to 6 carbon atoms, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group; n represents 0, 1, 2, 3 or 4;
Z is -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O
-, - S (O) _m -, - (C 1 -C 4 _{alkyl) -S (O) m -,} - S (O) m - ( alkyl having 1 to 4 carbon atoms) -, represents M represents 0, 1 or 2; B represents an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms; Or 2 carbon atoms
To 6 alkenyl groups or (C 2 -C 4 alkynyl) -C 1 -C 2 alkyl groups, each of which is unsubstituted or substituted by 1 to 3 halogen atoms. Or an aryl group or a heterocyclic group (these two are independently unsubstituted or C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, halogen Which is mono- or penta-substituted by C1 -C6 alkoxy or halo-C1 -C6 alkoxy).

Embedded image Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom, and p is 0, 1, 2 or 3), or a trimethylsilyl group;

R ₃ is a hydrogen atom, a C 1 -C 6
An alkyl group, a haloalkyl group having 1 to 6 carbon atoms having 1 to 5 halogen atoms, an alkoxy group having 1 to 4 carbon atoms and an alkyl group having 1 to 2 carbon atoms, 4 alkenyl) -C 1 -C 2 alkyl, which is unsubstituted or substituted by 1 to 3 halogen atoms, (C 2 -C 4 alkynyl) -carbon An alkyl group having 1 to 2 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms (which is unsubstituted or substituted by 1 to 4 halogen atoms), (a cycloalkyl group having 3 to 6 carbon atoms) Alkyl) -alkyl group having 1 to 4 carbon atoms (which is unsubstituted or substituted by 1 to 4 halogen atoms), cyano-
C 1-4 alkyl group; (C 1-4 alkoxy) carbonyl-C 1-2 alkyl group, (C 1-4 alkoxy) carbamoyl-C 1-2 carbon atom Alkyl, phenyl-C 1-3 alkyl (unsubstituted or halogen, C 1-3 alkyl, C 1-4 alkoxy, carbon Substituted with 1 to 4 haloalkyl group, cyano group, nitro group or C1 to C4 alkylenedioxy group, and phenyl group mono- or tri-substituted by the same or different substituents. Unsubstituted or C1-C4 alkyl group, C1-C4 alkoxy group, halogen atom, A haloalkyl group having 1 to 2 carbon atoms having 3 halogen atoms, a phenyl group which is monosubstituted or independently disubstituted by a nitro group or a cyano group; or an unsubstituted or 1 to 4 carbon atom Monosubstituted or independently disubstituted by an alkyl group, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a haloalkyl group having 1 to 3 carbon atoms having 1 to 3 halogen atoms, a nitro group or a cyano group. R ₄ represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or R ₃ and R ₄ together with the nitrogen atom to which they are attached are saturated or unsaturated. Saturated 5
A 7- to 7-membered ring, wherein the ring is unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms,
Which may have from 1 to 3 additional heteroatoms selected from O and S, provided that X is CH
Y represents OCH ₃ ; A represents an O atom; R ₁ represents a hydrogen atom and R ₃ represents a methyl group;
₂ represents a group other than a phenyl group substituted by only one or more chlorine atoms. ].

[0003]

The compounds of the present invention have fungicidal, acaricidal and fungicidal properties and are suitable as active ingredients for use in the agricultural, horticultural and hygiene fields. The present invention further provides a method for producing the compound of the present invention, and a fungicidal, acaricidal and fungicidal composition containing the compound of the present invention as an active ingredient, and for controlling plant-pathogenic fungi, mites and insects. And to the use of such compounds to prevent such attacks.

When an asymmetric carbon is present in a compound of formula I, the compound exists in optically active form. The compounds are present in each case in the form of [E] and / or [Z] simply because aliphatic double bonds of the oximino and hydrazo type are present. In addition, atropisomers may be present. Formula I represents all these possible isomers and mixtures thereof, such as racemic mixtures, and any [E /
Z] mixtures.

Unless defined otherwise, the above and following predicates are intended to mean the following: WO 90
/ 07493 discloses the methyl esters of aldimino and ketimino-oxy-ortho-tolylacrylic acid as fungicides, which differ from the compounds of the present invention.

A halogen atom is a fluorine atom, a chlorine atom,
Represents a bromine or iodine atom, especially a fluorine, chlorine or bromine atom, especially a fluorine or chlorine atom.

The alkyl group may be any linear alkyl group, for example, methyl, ethyl, n-propyl, n-propyl.
Butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl, or branched, for example, isopropyl,
It is an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group or an isohexyl group.

Alkenyl groups are straight-chain or branched alkenyl groups, for example vinyl, 1-methylvinyl, allyl, 1-butenyl, isopropenyl, especially allyl. Alkynyl is, for example, ethynyl, 1-propynyl or 1-butynyl, especially propargyl.

The cycloalkyl group is a cyclopropyl group,
It is understood that it means a cyclobutyl, cyclopentyl or cyclohexyl group.

A group substituted by a halogen such as a haloalkyl group or a haloalkoxy group may be partially or wholly halogenated by a different or similar group. Examples of haloalkyl groups are methyl groups mono- or trisubstituted by fluorine, chlorine and / or bromine atoms, such as CHF ₂ , CF ₃ or CH ₂ Cl; fluorine, chlorine and / or bromine atoms. single - or pentasubstituted has been and ethyl group, for example CH ₂ CF _3, CF ₂ C
F ₃ , CF ₂ CCl ₃ , CF ₂ CHCl ₂ , CF ₂ CHF ₂ ,
CF ₂ CFCl ₂ , CH ₂ CH ₂ Cl, CF ₂ CHBR ₂ , C
F ₂ CHClF, CF ₂ CHBrF or CClFCCl
F; trifluoromethyl groups are very particularly preferred.

The linear alkylene dioxy group having 1 to 4 carbon atoms includes -O-CH ₂ -O- and -O-CH ₂ CH
_{2 -O -, - O-CH} 2 CH 2 CH 2 -O- or -O-CH
₂ -CH ₂ CH ₂ is CH ₂ -O-. An aryl group is for example a phenyl or naphthyl group, especially a phenyl group.

The heterocyclic ring is 5- to 7- having 1 to 3 heteroatoms selected from the group consisting of N, O and S.
It is a membered aromatic or non-aromatic ring. Preference is given to aromatic 5- and 6-membered rings having a nitrogen atom as a heteroatom and, where appropriate, further heteroatoms, preferably a nitrogen or sulfur atom, especially a heterocycle with a nitrogen atom.

The predicate of the 5- to 7-membered ring formed by R ₃ and R ₄ together with the nitrogen atom to which they are attached is:
In particular, pyrrolidine, piperidine, morpholine, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole, 1,2,3
-Including triazole, tetrazole, isoxazole, oxazole, isoxazolidine, oxazolidine, thiazole, isothiazole, thiazolidine and isothiazolidine.

Preferred among the invention are the following: (1) wherein a) X represents an N atom and Y represents OCH ₃ or NHCH ₃ , or b) X represents CH and Y Is any of OCH ₃ ; and further, wherein A represents an O atom or a NR ₄ group; R ₁ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halo-carbon atom. R 1 represents an alkyl group, a cyclopropyl group, a cyano group or a methylthio group;
₂ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms,
A cycloalkyl group having 3 to 6 carbon atoms,

Embedded image Or a thienyl group; the D groups are the same or different,
Halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 2 carbon atoms, haloalkoxy group having 1 to 2 carbon atoms, 3 to 6 carbon atoms An alkenyloxy group, an alkynyloxy group having 3 to 6 carbon atoms, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group; n represents 0, 1, 2, 3 or 4;
Z is -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O
-, - S (O) _m -, - (C 1 -C 4 _{alkyl) -S (O) m -,} - S (O) m - ( alkyl having 1 to 4 carbon atoms) -, represents M represents 0, 1 or 2; B represents an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms; Or 2 carbon atoms
To 6 alkenyl groups or (C 2 -C 4 alkynyl) -C 1 -C 2 alkyl groups, each of which is unsubstituted or substituted by 1 to 3 halogen atoms. Or an aryl or heterocyclic group, or an aryl or heterocyclic group (each of which is independently an alkyl group of 1 to 6 carbon atoms,
Halo-C1-C6 alkyl group, halogen atom, C1-C6 alkoxy group or halo-C1-C6 alkoxy group). Or group:

Embedded image Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom, and p is 0, 1, 2 or 3);

R ₃ is a hydrogen atom, 1 to 6 carbon atoms.
An alkyl group, a haloalkyl group having 1 to 6 carbon atoms having 1 to 5 halogen atoms, an alkoxy group having 1 to 4 carbon atoms and an alkyl group having 1 to 2 carbon atoms, 4 alkenyl) -C 1 -C 2 alkyl, which is unsubstituted or substituted by 1 to 3 halogen atoms, (C 2 -C 4 alkynyl) -carbon An alkyl group having 1 to 2 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms (which is unsubstituted or substituted by 1 to 4 halogen atoms), (a cycloalkyl group having 3 to 6 carbon atoms) Alkyl) -alkyl group having 1 to 4 carbon atoms (which is unsubstituted or substituted by 1 to 4 halogen atoms), cyano-
C1 -C4 alkyl; (C1 -C4 alkoxy) carbonyl-C1 -C2 alkyl, phenyl-C1 -C3 alkyl (unsubstituted Or a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, an alkylene dialkyl having 1 to 4 carbon atoms. It is possible that the phenyl group is mono- or trisubstituted by the same or different substituents, substituted by an oxy group.); Unsubstituted or C 1 -C 4 alkyl groups, carbon atoms An alkoxy group of 1 to 4 halogen atoms, a haloalkyl group of 1 to 2 carbon atoms having 1 to 3 halogen atoms, a nitro group or a cyano group A more monosubstituted or independently disubstituted phenyl group; or an unsubstituted or C1-C4 alkyl group, C1-C4 alkoxy group, halogen atom, 1-3 halogen atom Represents a pyridyl group which is monosubstituted or independently disubstituted by a C1 to C2 haloalkyl group, a nitro group or a cyano group having the formula: R ₄ represents a C1 to C4 alkyl group or a phenyl group; Or R ₃ and R ₄ together with the nitrogen atom to which they are attached are a saturated or unsaturated 5- to 7-membered ring, which ring is unsubstituted or has 1 to 7 carbon atoms A compound of formula I, which is substituted by an alkyl group of 4 and can have from 1 to 3 additional heteroatoms selected from N, O and S).

In the formula (2), X represents N and Y represents OCH_Three
A compound of formula I which represents (3) The compound of the formula I, wherein X represents CH. (4) wherein X represents N and Y is NHCH_ThreeRepresent
R₁Is H, CH_Three, A cyclopropyl group or a formula representing CN
Compound of I. (5) wherein A is an oxygen atom, NCH_ThreeOr n-C₆H_Five, Special
An oxygen atom or NCH _ThreeA formula that represents, very particularly, an oxygen atom
Compound of I. (6) R₁Is a hydrogen atom, a methyl group, a cyclopropyl group or
Compounds of the formula I representing a cyano group, in particular a methyl group. (7) where R_TwoIs an alkyl group having 1 to 4 carbon atoms or
Is a cyclopropyl group, especially a methyl group or cyclopropyl
A compound of formula I which represents the group

In the formula (8), R ₂ is a group:

Embedded image D represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, 1
C1 to C2 alkyl, C1 to C2 haloalkoxy, C3 to C6 alkenyloxy, C3 to C6 substituted by 5 to 5 halogen atoms Represents an alkynyloxy group, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group, or a thienyl group; D is particularly a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 4 carbon atoms or compounds of formula I representing a -CF _3.

(9) In the formula, R ₂ is a group:

Embedded image And Z is -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O-, -S (O) ₂ -,- (C 1 -C 4 _{alkyl) -S (O) 2 -,} - S (O) 2 - ( alkyl of 1 to 4 carbon atoms) -, in particular, -O -, -
CH ₂ —O— or —O—CH ₂ —, very particularly —O—CH
A compound of formula I representing _2- .

Wherein R ₂ is a group:

Embedded image And B represents an alkyl group having 1 to 4 carbon atoms, a halogen atom-an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms or (2 to 4 carbon atoms) 4 alkynyl) -C 1-2 alkyl groups, each of which is unsubstituted or substituted by one to three halogen atoms
Or an aryl group, or a group having 1 to 2 carbon atoms.
Mono- or independently di-substituted by an alkyl group, a halo-alkyl group having 1 to 2 carbon atoms, a halogen atom, an alkoxy group having 1 to 2 carbon atoms or an alkoxy group having 1 to 2 carbon atoms. Represents an aryl or a group:

Embedded image Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 2 carbon atoms or a halogen atom, and p is 0, 1, And B represents, in particular, C 1 -C 2 alkyl, halo-C 1 -C 3 alkyl, or allyl or propargyl, each of which is Unsubstituted or substituted in each case by one or two halogen atoms or one or two methyl radicals), or a phenyl radical or a fluorine, chlorine, bromine and CF ₃ radical A phenyl group substituted by a group selected from the group consisting of:

Embedded image A compound of formula I which represents

(11) The compound of the formula I, wherein R ₂ is a phenyl group substituted at the 4-position by -ZB.

In the formula (12), R ₃ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms having 1 to 3 halogen atoms, (1 to 3 carbon atoms) 2 alkoxy) -C1 -C2 alkyl, (C1 -C4 alkoxy) -carbonyl -C1 -C2 alkyl, unsubstituted or C1 -C3 halogen Substituted propenyl, propargyl, cycloalkyl having 3 to 6 carbon atoms, cyclopropylmethyl unsubstituted or substituted by 1 or 2 halogen atoms, cyano-C 1 -C 2 Alkyl, phenyl-C 1-2 alkyl, which is unsubstituted or halogen, methyl,
It is possible for a methoxy group or a halomethyl group having 1 to 3 halogen atoms to be substituted and for the phenyl group to be mono- or disubstituted by the same or different substituents. An unsubstituted or substituted phenyl group mono- or independently disubstituted by a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group; Or a halogen atom, a methyl group, a methoxy group, 1 to 3
Represents a pyridyl group which is monosubstituted or independently disubstituted by a halomethyl group, a cyano group or a nitro group having two halogen atoms; or

R ₃ and R ₄ are taken together with the nitrogen atom to which they are attached to a saturated or unsaturated 5- to 7-membered ring, which is unsubstituted or has 1 to 4 carbon atoms. And may have from 1 to 3 additional heteroatoms selected from N, O and S); preferably, R ₃ is hydrogen, 1 carbon atom A C6 alkyl group or a C1-4 haloalkyl group having 1 to 3 halogen atoms,
(Alkoxy having 1 to 2 carbon atoms) -methyl group, prop-2-en-1-yl group which is unsubstituted or substituted by 1 to 3 halogen atoms, propargyl group, 3 to 6 carbon atoms A cycloalkyl group which is unsubstituted or substituted by one or two fluorine or chlorine atoms, a cyano-alkyl group having 1 to 2 carbon atoms, a phenyl-carbon atom having 1 carbon atom
Or 2 alkyl groups, which are unsubstituted or substituted by halogen atoms, methyl groups, methoxy groups or halomethyl groups having 1 to 3 halogen atoms,
It is possible for the phenyl group to be mono- or disubstituted by the same or different substituents. An unsubstituted or substituted phenyl group mono- or independently disubstituted by a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group; the or halogen atom, a methyl group, a methoxy group, one to a halomethyl group having three halogen atoms, or represents a cyano group or a pyridyl group by a nitro group which is mono- or independently disubstituted; a or R ₃ R ₄
Together with the nitrogen atom to which they are attached,
A compound of the formula I, which represents a 2,4-triazolyl, 4-morpholinyl, 1-azepinyl, 1-piperidinyl or 1-pyrrolidinyl group; R ₃ very particularly represents a methyl group.

(13) Compounds of the formula I wherein R ₄ represents a methyl group or a phenyl group, especially a methyl group. (14) wherein X represents CH; Y represents OCH ₃ ; R ₁
Represents CH ₃ ; A represents an oxygen atom; R ₂ represents a 4-methylphenyl group or a 4-allyloxyphenyl group or 4-
A compound of formula I which represents a (3-trifluoromethyl-benzyloxy) phenyl group or a 4- (2,2-dichlorocyclopropylmethoxy) phenyl group; and R ₃ represents CH ₃ .

(15) wherein a) X represents an N atom and Y represents OCH ₃ or NHCH ₃ , or b) X represents CH and Y represents OCH ₃ ; And further in the formula, A represents an O atom or a NR ₄ group; R ₁ is a hydrogen atom,
Represents an alkyl group having 1 to 4 carbon atoms, a cyclopropyl group, a cyano group or a methylthio group; R ₂ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 3 carbon atoms;
6 to 6 cycloalkyl groups; unsubstituted or halogen atoms, C1 to C4 alkyl groups, C1
C4 to C4 haloalkyl group, C1 to C2 haloalkoxy group, C3 to C6 alkenyloxy group, C3 to C6 alkynyloxy group, carbon atom 1 atom
A phenyl group mono- or independently di-substituted by an alkylenedioxy group, a cyano group or a nitro group;

R ₃ is a hydrogen atom, a C1-6 alkyl group or a C1-6 haloalkyl group having 1-5 halogen atoms; (C1-4 alkoxy) -carbon C1 -C2 alkyl; (C2 -C4 alkenyl)-C1 -C2 alkyl, which is unsubstituted or substituted by C1 -C3 halogen ), (Alkynyl having 2 to 4 carbon atoms) -alkyl group having 1 to 2 carbon atoms; cycloalkyl group having 3 to 6 carbon atoms, which is unsubstituted or has 1 to 4 halogen atoms Substituted), (C 3 -C 6 cycloalkyl) -C 1 -C 4 alkyl, which is unsubstituted or substituted by 1 to 4 halogen atoms Ri is substituted), cyano -
C1 -C4 alkyl; (C1 -C4 alkoxy) carbonyl-C1 -C2 alkyl, phenyl-C1 -C3 alkyl (unsubstituted Or a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, an alkylene dialkyl having 1 to 4 carbon atoms. It is possible that the phenyl group is mono- or trisubstituted by the same or different substituents, substituted by an oxy group.); Unsubstituted or C 1 -C 4 alkyl groups, carbon atoms An alkoxy group of 1 to 4 halogen atoms, a haloalkyl group of 1 to 2 carbon atoms having 1 to 3 halogen atoms, a nitro group or a cyano group A more monosubstituted or independently disubstituted phenyl group; or an unsubstituted or C1-C4 alkyl group, C1-C4 alkoxy group, halogen atom, 1-3 halogen atom Represents a pyridyl group which is monosubstituted or independently disubstituted by a C1 to C2 haloalkyl group, a nitro group or a cyano group having the formula: R ₄ represents a C1 to C4 alkyl group or a phenyl group; Or R ₃ and R ₄ together with the nitrogen atom to which they are attached are a saturated or unsaturated 5- to 7-membered ring, which ring is unsubstituted or has 1 to 7 carbon atoms A compound of formula I substituted by an alkyl group of 4 to form one or more additional heteroatoms selected from N, O and S).

(16) X represents CH or N; Y represents OCH
_ThreeA represents O or N—R_FourR;₁Is a methyl group,
R represents a cyclopropyl group or a methylthio group;_TwoBut
A cyclopropyl group; an unsubstituted or halogen atom,
C1 -C4 alkyl, no C1
4 alkoxy groups and 1 to 5 halogen atoms
A substituted or unsubstituted alkyl group having 1 or 2 carbon atoms,
Haloalkoxy group having 1 or 2 carbon atoms, number of carbon atoms
An alkenyloxy group having 3 to 6 carbon atoms having 3 to 6 carbon atoms
6 alkynyloxy groups, C 1 -C 4 alkyl
Monosubstituted with a killenedoxy group, cyano group or nitro group
Or an independently disubstituted phenyl group;
A carbonyl group; and wherein R_ThreeWas described in Formula I
Street and R_FourRepresents a methyl group or a phenyl group
Or R_ThreeAnd R _FourIs the same as the nitrogen atom to which they are attached.
In the beginning, pyrrolidine, piperidine, morpholine,
Omorpholine, hexamethyleneimine, imidazole,
Pyrazole, pyrrole, 1,2,4-triazole or
Compounds of formula I representing any of the 1,2,3-triazoles
object.

(17) In the formula, X represents N; Y is NHCH
_ThreeA represents O or N—R_FourR;₁Is a methyl group,
R represents a cyclopropyl group or a methylthio group;_TwoBut
A cyclopropyl group; an unsubstituted or halogen atom,
C1 -C4 alkyl, no C1
4 alkoxy groups and 1 to 5 halogen atoms
A substituted or unsubstituted alkyl group having 1 or 2 carbon atoms,
Haloalkoxy group having 1 or 2 carbon atoms, number of carbon atoms
An alkenyloxy group having 3 to 6 carbon atoms having 3 to 6 carbon atoms
6 alkynyloxy groups, C 1 -C 4 alkyl
Monosubstituted with a killenedoxy group, cyano group or nitro group
Or an independently disubstituted phenyl group;
A carbonyl group; and wherein R_ThreeWas described in Formula I
Street and R_FourRepresents a methyl group or a phenyl group
Or R_ThreeAnd R _FourIs the same as the nitrogen atom to which they are attached.
In the beginning, pyrrolidine, piperidine, morpholine,
Omorpholine, hexamethyleneimine, imidazole,
Pyrazole, pyrrole, 1,2,4-triazole or
Compounds of formula I representing any of the 1,2,3-triazoles
object.

(18) In the formula, A represents an O atom; R ₁ represents a methyl group; R ₂ represents a methyl group; unsubstituted or a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a carbon atom number. 1 to 4 alkoxy groups, 1 to 2 carbon atom alkyl groups, 1 to 2 carbon atom haloalkoxy groups, and 3 to 6 carbon atom alkenyloxy groups substituted by 1 to 5 halogen atoms , 3 carbon atoms
6 to 6 alkynyloxy groups, having 1 to 4 carbon atoms
A phenyl group mono- or independently di-substituted by an alkylenedioxy group, a cyano group or a nitro group; or a thienyl group; and R ₃ represents an alkyl group having 1 to 6 carbon atoms; X and Y are compounds of formula I as defined for formula I.

(19) wherein R ₁ represents a methyl group; R ₂ represents a methyl group and R ₃ is as described in claim 1 and R ₄ represents a methyl group or a phenyl group. ,
Or R ₃ and R ₄ are, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered ring, which is unsubstituted or C 1 -C 4 alkyl Substituted with a group, which may have from 1 to 3 additional heteroatoms selected from N, O and S), while X and Y are as defined for formula I A compound of formula I as defined above.

(20) In the formula, R ₃ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms and having 1 to 3 halogen atoms; 2 alkoxy) -alkyl group having 1 to 2 carbon atoms; unsubstituted or substituted with 1 to 3 halogen atoms, propenyl group, propargyl group, cycloalkyl group having 3 to 6 carbon atoms; unsubstituted Or a (C3-C6 cycloalkyl) methyl group, cyano-C1-C2alkyl group, (C1-C2alkoxy) substituted by one or two halogen atoms Carbonyl-alkyl group having 1 or 2 carbon atoms; phenyl-alkyl group having 1 carbon atom
Or 2 alkyl groups, which are unsubstituted or halogen atoms, methyl groups, methoxy groups, halomethyl groups having 1 to 3 halogen atoms, cyano groups, nitro groups or alkylene dialkyl groups having 1 to 2 carbon atoms. Substituted by an oxy group, and the phenyl group can be mono- or di-substituted by the same or different substituents.); Unsubstituted or halogen atom, methyl group, methoxy group, 1-3 A phenyl group mono- or independently di-substituted by a halomethyl group, a cyano group or a nitro group having two halogen atoms; or an unsubstituted or halogen atom, a methyl group, a methoxy group, and 1 to 3 halogen atoms halomethyl group, a mono- or independently disubstituted with which pyridyl group by a cyano group or a nitro group with a; R ₄ is methyl group or Or a phenyl group; or R ₃
And R ₄ together with the nitrogen atom to which they are attached, are saturated or unsaturated, 5- to 7-membered rings, which are unsubstituted or substituted by C 1 -C 4 alkyl groups. 17. The compound of formula I according to claim 16, wherein the compound of formula (I) has from 1 to 3 additional heteroatoms selected from N, O and S. At the same time, A, X,
Y, a compound of formula I, wherein R ₁ and R ₂ are defined the same as defined for formula I.

(21) In the compounds of formula I described in (20), R ₃ and R ₄ together with the nitrogen atom to which they are attached form a triazolyl group, morpholinyl group, ,
A compound representing a 6-dimethylmorpholinyl group, an azepinyl group, a piperidyl group or a pyrrolidinyl group.

(22) wherein A represents an O atom; R ₁ represents a methyl group; R ₂ represents a methyl group; an unsubstituted or halogen atom, an alkyl group having 1 to 4 carbon atoms, and a carbon atom number. 1 to 4 alkoxy groups, 1 to 2 carbon atom alkyl groups, 1 to 2 carbon atom haloalkoxy groups, and 3 to 6 carbon atom alkenyloxy groups substituted by 1 to 5 halogen atoms , 3 carbon atoms
6 to 6 alkynyloxy groups, having 1 to 4 carbon atoms
A phenyl group mono- or independently di-substituted by an alkylenedioxy group, a cyano group or a nitro group; or a thienyl group; and R ₃ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1 to 4 haloalkyl groups having 1 to 3 carbon atoms; (C1 to 2 alkoxy) -alkyl groups having 1 to 2 carbon atoms; unsubstituted or 1 to 3 halogen atoms A propenyl group, a propargyl group, a C3-C6 cycloalkyl group; an unsubstituted or (C3-C6 cycloalkyl) methyl substituted by one or two halogen atoms Groups, cyano-C 1-2 alkyl, (C 1-2 alkoxy) carbonyl-C 1-2 carbon Alkyl group; phenyl - 1 carbon atoms
Or 2 alkyl groups, which are unsubstituted or halogen atoms, methyl groups, methoxy groups, halomethyl groups having 1 to 3 halogen atoms, cyano groups, nitro groups or alkylene dialkyl groups having 1 to 2 carbon atoms. Substituted by an oxy group, and the phenyl group can be mono- or di-substituted by the same or different substituents.); Unsubstituted or halogen atom, methyl group, methoxy group, 1-3 A phenyl group mono- or independently di-substituted by a halomethyl group, a cyano group or a nitro group having two halogen atoms; or an unsubstituted or halogen atom, a methyl group, a methoxy group, and 1 to 3 halogen atoms Represents a pyridyl group monosubstituted or independently disubstituted by a halomethyl group, a cyano group or a nitro group having X; Compounds of formula I that are identical to definition as defined for.

(23) In the compounds of the formula I described in (22), A represents an O atom; R ₁ represents a methyl group;
R ₂ is a methyl group; unsubstituted or halogen atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy mono- or independently disubstituted with which phenyl group by group; and R ₃ is methyl A compound that represents a group.

(24) wherein A represents NCH ₃ ; R ₁ represents a methyl group; R ₂ represents a methyl group; unsubstituted or halogen atom, methyl, methoxy, trifluoromethyl or trifluoromethyl A phenyl group which is monosubstituted or independently disubstituted by a methoxy group; R ₃ is a methyl group; unsubstituted or a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, A phenyl group monosubstituted or independently disubstituted by a cyano group or a nitro group; or an unsubstituted or halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group Represents a pyridyl group which is monosubstituted or independently disubstituted by a group; while X and Y represent the formula I as defined for formula I
Compound.

(25) In the formula, X represents an N atom; Y represents OR
Represents _11; R ₁₁ represents an alkyl group of 1 to 4 carbon atoms; and wherein, A, compounds of formula I R _1, R ₂ and R ₃ are the same as defined for formula I.

(26) In the compounds described in (25), in the formula, A represents an O atom; R ₁ and R ₂ represent a methyl group;
₃ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1
1 to 4 carbon atoms having from 3 to 3 halogen atoms
Haloalkyl group; (C 1-2 alkoxy) -C 1-2 alkyl group; unsubstituted or substituted by 1-3 halogen atoms, propenyl group, propargyl group, carbon atom number 3 to 6 cycloalkyl groups; unsubstituted or substituted by 1 to 2 halogen atoms (C3 to C6 cycloalkyl) methyl group, cyano-C1 to C2 alkyl group, (C1 -C2 alkoxy) carbonyl-C1 -C2 alkyl group;
Phenyl-alkyl having 1 to 2 carbon atoms, which is unsubstituted or halogen, methyl, methoxy, halomethyl having 1 to 3 halogens,
It is possible for the phenyl group to be mono- or disubstituted by the same or different substituents, being substituted by a cyano group, a nitro group or an alkylenedioxy group having 1 or 2 carbon atoms. An unsubstituted or substituted phenyl group mono- or independently disubstituted by a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group; Or a halogen atom, a methyl group, a methoxy group, 1
A compound representing a pyridyl group which is monosubstituted or independently disubstituted by a halomethyl group, a cyano group or a nitro group having 3 to 3 halogen atoms.

(27) In the compounds described in (26), in the formula, R ₃ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a C 1 to C 4 having 1 to 3 halogen atoms. A compound representing a haloalkyl group of

(28) In the formula, X represents an N atom;
(R ₁₂ ) represents R ₁₃ ; R ₁₂ and R ₁₃ independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and wherein A, R ₁ , R ₂ and R ₃ represent A compound of formula I as defined for formula I.

(29) In the compounds described in (28), Y represents NH ₂ , N (CH ₃ ) ₂ or NHC ₂ H ₅ ;
Represents an O atom; R ₁ and R ₂ represent a methyl group; R ₃ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and a haloalkyl having 1 to 3 carbon atoms having 1 to 3 halogen atoms. A group; (C 1-2 alkoxy)-
C1-C2 alkyl; unsubstituted or substituted by 1-3 halogen atoms, propenyl, propargyl, C3-C6 cycloalkyl; unsubstituted or 1-2 (C3-C6 cycloalkyl) methyl, cyano-C1-C2 alkyl, (C1-C2alkoxy) carbonyl-carbon substituted by 3 halogen atoms 1 to 2 alkyl groups; phenyl-C1 to C2 alkyl group, which is unsubstituted or halogen atom, methyl group, methoxy group,
Substituted by a halomethyl group, a cyano group, a nitro group or an alkylenedioxy group having 1 or 2 carbon atoms, wherein the phenyl group is mono- or di-substituted by the same or different substituents. It is possible that An unsubstituted or substituted phenyl group mono- or independently disubstituted by a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group; Or a halogen atom, a methyl group, a methoxy group, 1 to 3
A compound representing a pyridyl group which is monosubstituted or independently disubstituted by a halomethyl group, a cyano group or a nitro group having two halogen atoms.

(30) In the compounds described in (29), in the formula, R ₃ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a carbon atom having 1 to 3 halogen atoms.
A compound representing 1 to 4 haloalkyl. (31) The compound of the formula I, wherein the double bond of X = C is in the E form.

The compound of formula I can be prepared as follows: A) To prepare a compound of formula I wherein Y represents N (R ₁₂ ) R ₁₃ : wherein Y is OR ₁₁ Is reacted with HN (R ₁₂ ) R ₁₃ in a solvent at 0 ° C. to 40 ° C.

The above reaction is advantageously carried out in an inert organic diluent, for example: an alcohol such as ethanol, an ether such as tetrahydrofuran or dioxane, an ester such as ethyl acetate, dimethyl sulfoxide. Sulfoxides such as amides such as dimethylformamide or ketones such as methyl ethyl ketone. Methylamine can be used in gaseous or otherwise dissolved form, for example in the form of an ethanol solution. The treatment temperature is between 0 ° C and 40 ° C, preferably at room temperature.

B) wherein X, Y, A and R ₁ to R ₃ are defined the same as defined for formula I (and in which case R ₃ does not represent a hydrogen atom) To prepare compounds: general formula II

Embedded image (Wherein A and R ₁ to R ₃ are defined as above)
The oxime represented by the general formula

Embedded image Wherein X and Y are as defined above and U is a leaving group.

The above reaction is a nucleophilic reaction and can be carried out under reaction conditions commonly used in such a case. Leaving group U
Is preferably a chlorine atom, a bromine atom, an iodine atom, a mesyloxy group or a tosyloxy group. The reaction is carried out, for example, in an inert organic diluent as described below, in the presence of a base as described below, at a temperature between −20 ° C. and 80 ° C., preferably at 0 ° C.
It is advantageous to work in the temperature range from 50 ° C. to 50 ° C .:
Cyclic ethers such as tetrahydrofuran or dioxane, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide; dibasic agents such as sodium hydride;
Sodium carbonate, potassium carbonate, sodium amide, tertiary amines such as trialkylamines, especially diazabicyclononane or diazabicycloundecane, or silver oxide.

Alternatively, the reaction may be carried out using a phase transfer catalyst, in an organic solvent such as methylene chloride, in the presence of an aqueous alkaline solution such as sodium hydroxide solution and, for example, tetrabutylammonium hydrogen sulfate as the phase transfer catalyst. Below, at room temperature.

The resulting compounds of the formula I can be isolated and purified in a manner known per se. Similarly, isomer mixtures, such as E / Z isomer mixtures, can be separated in a manner known per se, for example by chromatography or fractional crystallization, to give pure isomers.

The oximes of the general formula II used as starting materials are known or can be prepared by known processes [cf. J. Chem. Soc., Perkin Trans II 537 (1990);
Ber. Deutsh. Chem. Ges. 62 , 866 (1629); Gazz Chim.
Ital. 37 II, 147 (1907); Liebigs Ann. Chem. 262 ,
305 (1891)].

The starting materials of the formula III can likewise be prepared in a manner known per se, for example as described below:
EP-A-203606 (BASF) and references cited therein, or Angew. Chem. 7 1,349-365 (1959).

C) wherein A represents an oxygen atom and X,
To prepare a compound of formula I wherein Y and R ₁ to R ₃ are defined as for formula I:

Embedded image (Where X, Y, R ₁ and R ₂ are defined as above)
A compound represented by the general formula

Embedded image U—R ₃ V wherein R ₃ is a group of the formula I
And U is defined as in Formula III (where R ₃ is not a hydrogen atom, a phenyl group or a pyridyl group)]. This reaction is the nucleophilic reaction described in B).

D); D) To prepare a compound of formula IV wherein X, Y, R ₁ and R ₂ are defined as for formula I, the process is as follows: Formula VI

Embedded image (Where X, Y, R ₁ and R ₂ are defined as above)
Is reacted with hydroxylamine or a salt thereof such as hydrochloride at 0 ° C. to 50 ° C. in a solvent. The reaction is carried out in pyridine or methanol as a solvent.
It is advantageous to work at a temperature between -20 ° C. and + 80 ° C. or at the boiling point of methanol, preferably in the temperature range from 0 ° C. to 50 ° C.
A base, for example an alkali metal carbonate such as potassium carbonate,
Requires a tertiary amine such as triethylamine or diazobicyclononane, pyridine or silver oxide.

The ketones of the general formula VI can be prepared analogously to the method described in B). Ketones of the general formula VI and their preparation are described, for example, in the following documents: EP-
370629, EP-506149, EP-40361
8, EP-414153, EP-463488, EP-
472300, EP-460575, WO-92 / 18
494 and other publications.

E) to prepare compounds of the formula I in which A, X, Y and R ₁ to R ₃ are defined as for the formula I (and in which case R ₃ is not a hydrogen atom) Is
The method follows, for example, the following method:

Embedded image Wherein A, X, Y and R ₁ to R ₃ are as defined above, are reacted with a methylating agent such as methyl iodide, dimethyl sulfate or diazomethane. The reaction is advantageously carried out in the presence of a base such as potassium carbonate or sodium hydride and a suitable solvent at a suitable reaction temperature (see, for example, HS Ankerund H.T.C.
Larke; Organic Synthesis, Coll. Vol. 3,172.).

F) wherein A, X, Y and R ₁ to R ₃ are the same as defined for formula I, in order to prepare compounds of the formula VII, it is advantageous to follow the following process:

Embedded image (Wherein A, Y and R ₁ to R ₃ are defined as above), using EP-A-178826.
In the same way as described in
e) in the presence of a base or EP-A-25
The nitrosation reaction with nitrous acid or nitrite in the presence of a base is carried out as described in 4426.

Another possibility for preparing compounds of the formula VII is the following reaction:

Embedded image (Wherein A, Y and R ₁ to R ₃ are defined as above), using EP-A-178826.
Reaction with methoxymethylenetriphenylphosphorane or EP-A
In the same manner as described in US Pat.
React with methylhydroxylamine (or a salt thereof). The novel compounds II, VII, VIII and IX are also provided by the invention, in particular the compounds of the formulas II.1 and II.2:

Embedded image

Surprisingly, the compounds of the formula I have a spectrum of microbicidal action against phytopathogenic microorganisms, especially molds (fungi), which is favorable for practical requirements. That is now found.

These compounds have very useful pathogenic, preventive and, in particular, systemic properties and can be used for the protection of many crops. Pests occurring on plant parts (fruits, flowers, leaves, stems, tubers, roots) in various crops that are plants or useful plants using the compounds represented by formula I Can be arrested or killed, while at the same time the parts of the plants that have subsequently grown remain free of such phytopathogenic microorganisms. The compounds of the formula I are furthermore resistant to soil infection and to soil-borne fungi, seeds (fruits, rhizomes, grains)
And can be used to treat seedling plants.

The compounds of the formula I are active against phytopathogenic fungi belonging, for example, to the following classes: Imperfect fungi [especially Botrytis, Pyricularia, Helminthosporium] , Fusarium, Septoria
a), Cercospora and Alternaria]; Basidiomycetes [eg, Rhizoctonia, Hemireia
ileia), Puccinia); Ascomycetes (eg, Venturia and Ercipe)
he), Podosphaera,
Monilinia, Uncinula (Un
oomycetes] [for example, Phytophthora, Peronospora, Bremia, Pythium, Lasmopara.

The compounds of the formula I only have an even more valuable activity on useful and ornamental plants in agriculture and horticulture, especially on rice, cotton, vegetable and fruit crops, and on insects and mites found in forests. Not resistant to warm-blooded animals, fish and crops. The compounds I are suitable for controlling rice, fruit and vegetable insects, in particular plant pests. Another field of application of the active ingredients according to the invention is the protection of stored goods and materials and, in the hygiene field, in particular the protection of livestock and livestock. The compounds of the formula I are active against all or individual developmental stages of pest species which are not only normally sensitive but also resistant. Their activity is also evident, for example, from the killing of pests immediately after application or after a certain period of time, for example during moulting, or from a reduction in egg production and / or hatchability.

The above-mentioned pests include, for example, the following: from the order Lepidoptera, for example, Acleris spp., Adoxophys sp.
ophyes spp.), Aegeria spp., Agrotis spp., Alabama algiracee (Alab
ama argillaceae), Amylois spp., Anticarsia gemmatalis,
Archips spp., Argylotenia species (Atgyr
otaenia spp.), autographa species (Autographa spp.),
Busseola fusca, Carda cautella, Carposina Nipponensis
(Carposina nipponensis), Chilo spp., Choristoneura sp., Clysia ambiguella, Cnapharocrosis
(Cnaphalocrosis spp.), Cnephasia sp.
p.), Cochlis spp., Coleophora spp.
leophora spp.), Crocidromia vinothalis (Crocido
lomia binotalis), Cryptoflavia leukotreta
(Cryptophlebia leucotreta), Syria species (Cydia sp.
p.), Diatrea spp., Diparopsis castanea, Aerias (Earias)
spp.), Ephestia spp., Eucosma spp., Eupesilia ambiguera (Eupo)
ecillia ambiguella), Euproctis s species (Euproctis s
pp.), Euxoa spp., Graholita sp.
pholita spp.), Hedya nubifera
na), Heliothis spp., Hella sp.
ula spp.), Hyphantria cune
a), Keiferia lycoper
sicella), Leucoptera scitell
a), Lithocollethis spp., Lobesia botrana, Lymantria
hria spp.), Rionetia sp. (Lyonetia spp.), Malakosoma sp. (Malacosoma spp.), Maamestra brassike (Ma
mestra brassicae), Manduka sexta (Manduca sex)
ta), Operophtera spp., Ostrinia nubilalis, Pamené sp.
mmene spp.), Pandemis spp., Panolis flammea, Pectinophora
Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris sp.
p.), Plutella xylostella,
Place species (Prays spp.), Shirpofaga species (Scirpophag
a spp.), Sesamia sp. (Sesamia spp.), Sparganothis sp. (Sparganothis spp.), Spodoptera sp.
pp.), Synanthendon species (Synanthedon spp.), Taumetopea (Thaumetopoea spp.), Tortrix species (Tortrix s.
pp.), Trichoplusia ni and Uponomoita species (Yponomeuta spp.);

From the order Coleoptera, for example, Agriotes spp., Antnomus sp.
(Anthonomus spp.), Atomaria
linearis), Chetocnema tibi
alis), Cosmopolites sp., Curculio spp., Dermestes sp.
p.), Diabrotica species (Diabrotica spp.), Epilacuna species (Epilachna spp.), Elemnus species (Elemnus spp.),
Leptinotarsa decemlineata
ineata), Lissorhoptrus sp.
p.), Melolontha sp. (Oryzaephilus spp.), Otiorhyn sp.
chus spp.), Phlyctinus spp., Popillia sp., Psylliodes sp.
spp.), Rhizopertha spp., Scalabeidae, Sitophilus sp.
p.), Sitotroga spp., Tenebrio sp.
enebrio spp.), Triboliumspp. and Trogoderma spp .;

From the order Orthoptera, for example, species of Blatta spp., Species of Blattell
a spp.), Gryllotalpa spp., Leucophaea maderae, Roxta sp. (Locusta spp.), Periplaneta sp.
p.) and Schistocerca spp.
From the termites (order Isoptera), for example, Reticulitermes spp.
(order Psocoptera) from, for example, the liposelis species (Liposc
elis spp.) and flea eyes (order Anoplura)
Haematopinus spp., Linognathus spp., Pediculus sp.
p.), Pemphigus spp., and phylloxera species (Phylloxera spp.), Order Mellophag
From a), for example, Damalinea spp. and Trichodectes spp .;

From the order Thysanoptera, for example, Frankliniella spp., Herkinothrips spp., Taeniothrips spp., Tripips palmi
(Thrips palmi), Trip Starbucks (Thrips tabaci)
And Scirtothrips
aurantii); from the order Heteroptera, for example, Cimex spp., Distantiella theobroma, Dysdelcus (Dy)
sdercus spp.), Euchytus spp., Eurygaster spp., Leptocorisa sp.
ptocorisa spp.), Nezara spp., Piesma spp.
(Piesma spp.), Rhodnius species (Rhodnius spp.), Sahlbergella singularis,
Scotinophara spp. And Triatoma spp .;

From the order Homoptera, for example,
Aleurothrixus flo
ccosus), Aleyrodes brassicae
sicae), Aonidiella species (Aonidiella spp.), Aphididae, Aphis species (Aphis spp.), Aspidiotus species (Aspidiotus spp.), Bemisia tabaki (Bemisi
a tabaci), Keroplaster spp. (Ceroplaster spp.),
Chrysomphalus aonid
ium), Chrysomphalus
halus dictyospermi), Coccus hesperism (Coccus)
hesperidum), Empoasca sp. (Bmpoasca spp.), Eriozoma larigerum (Briosoma larigerum), Erythroneura sp. (Brythroneura spp.), Gascardia sp. (Gascar
dia spp.), Laodelphax sp.
p.), Lecanium corni, Lepidosaphes spp., Macrosifus sp.
iphus spp.), Myzus spp., nehotetics
(Nephotettix spp.), Nila Parvata (Nilaparvata spp.), Paratoria (Paratoria spp.), Pemphigus (Pemphigu)
s spp.), Planococcus spp., Pseudaulacaspis spp., Pseudodococcus spp., Psylla sp.
spp.), Pulvinaria aethiopi
ca), Quadraspidiotus sp.
p.), Rhopalodishum species (Rhopalosiphum spp.), Sissetia species (Saissetia spp.), Scafoideus species (Scap
hoideus spp.), Schizaphis spp., Sitobion sp., Trialeurodes sp., Triizaurodes spp., Troiza erytreae, and Unaspis citri.
spis citri);

From the order Hymenoptera, for example, Acromyrmex, Atta species (Atta
spp.), Cephus spp., Diprion species (Diprio
n spp.), Diprionidae, Gilpinia
Polypoma (Gilpinia polytoma), Hoplocampa species (Hoploc
ampa spp.), Radius species (Lasius spp.), Monomorium pharaonis (Monomorium pharaonis), Neodiprion species (Neodiprion spp.), Solenopsis species (Solenopsis s)
pp.), and Vespa spp.

From the order Diptera, for example, Aedes spp.
igona soccata), Bibio hortula (Bibio hortula)
nus), Calliphora ery
throcephala), Serratitis sp. (Ceratitis spp.), Chrysomyia sp. (Chrysomyia spp.), Crex sp. (Culexsp.)
p.), Cuterebra spp., Dacus
s spp.), Drosophila melanogaster
melanogaster), Fania species (Fannia spp.), Gastrophilus species (Gastrophilus spp.), Glossina species (Glos
sina spp.), Hypoderma spp., Hippobosca spp., Liriomyza sp.
spp.), Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia sp.
spp.), Oscinella frit, Pegomyia hyoscyami, Forbia
(Phorbia spp.), Lagoletis pomonella (Rhagoletis p
omonella), Sciara spp., Stomoxys sp.
(Stomoxys spp.), Tabanus species (Tabanus spp.), Tania species (Tannia spp.), And Tipura species (Tipula spp.); From the order Siphonaptera, for example, Ceratophyllus species (Ceratophyllus spp.), Xenopsyla cheopis, Order Thysanur
From a), Lepismasaccharina;
as well as

From the order Acarina, for example, Acarus siro, Aceria Cieldoni (Ace)
ria sheldoni), Aculus sheldendari
chlechtendali), Amblyomma spp.,
Argas spp., Boophilus sp.
spp.), Blevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Corioptes sp.
ioptes spp.), Dermanyssus gal
linae), Eotetranychus carpini (Eotetranychus)
carpini), Eriophyes spp., Hyalomma spp., Ixodes spp.,
Oligonychus pratensi
s), Ornithodros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Polyphagotarsonemus latus, P. r. sp. R. sp.
lus spp.), Rhizoglyphus species (Sarcoptes spp.), Tarsonemus species (Tars
onemus spp.) and Tetranychus sp.
p.).

Target crops to be protected within the scope of the present invention are, for example, the following: cereals (wheat, barley, rye, corn, sugar sorghum and related crops), beets (sugar beet and fodder beet), Pear fruits, stone fruits and soft fruits (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries), legumes (broad bean, lentils, peas, soybeans), oil plants (rapeseed, mustard) , Poppy, olive, sunflower, coconut, castor, cocoa bean, peanut), Cucurbitaceae (cucurbit, mallow, melon),
Textile plants (cotton, flax, hemp, jute), orange plants (orange, lemon, grapefruit, tangerine), vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, shii pepper), camphoraceae (Avocado, cinnamon, camphor) or tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapes, hops, bananas, natural rubber plants and ornamental plants.

The action of the compounds of the formula I according to the invention and the compositions containing them can be significantly extended by adding other microbicides, insecticides and / or acaricides and adapted to the controlling environment. Can be done. The following representative examples of active ingredients are examples of suitable additives: organophosphorus compounds, nitrophenols and their derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons and Baccillus thuringiensis.

In general, the active ingredients of the formula I are applied in the form of a composition, which can be applied to the cultivation site or the plant to be treated simultaneously or with the other active ingredients. These other active ingredients can be fertilizers or microelement mediators or other formulations that affect plant growth. Selective herbicides and also insecticides, fungicides, bactericides, nematicides, molluscides or some mixtures of these preparations, carriers, surfactants conventionally used in the preparation arts, Or they may be used with or without application aids.

Suitable carriers and auxiliary substances can be solid or liquid and are substances which are convenient in the art of formulation, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, binders and fertilizers. Suitable solvents are the following: aromatic hydrocarbons, preferably C8-C12 moieties,
Xylene mixtures or substituted naphthalenes; phthalates such as dibutyl phthalate or dioctyl phthalate; aliphatic hydrocarbons such as cyclohexane or paraffin; alcohols and glycols such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether and their ethers And esters; ketones such as cyclohexanone; N
Strong polar solvents such as methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide; and epoxy vegetable oils such as epoxidized coconut oil or soybean oil; or water.

Solid carriers which can be used, for example, in dusts and dispersible powders, are usually ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite. Particularly advantageous application-enhancing auxiliaries which can substantially reduce the application rates are natural (animal or vegetable) or synthetic phospholipids of the cephalin or lecithin type, which are obtained, for example, from soybean.

Suitable surface-active compounds, depending on the nature of the active ingredient of the formula I to be formulated, are nonionic, cationic and / or having good emulsifiability, dispersibility and wetting properties.
Or it is an anionic surfactant. It is to be understood that the term "surfactants" also includes mixtures of surfactants. Suitable anionic surfactants can also be so-called water-soluble salts and water-soluble synthetic surface-active compounds.

The soaps are obtained from alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C ₁₀ -C ₂₂ ), for example oleic acid or stearic acid, or for example coconut oil or tallow. Sodium or potassium salts of natural fatty acid mixtures. Fatty acid methyltaurine salts may also be used. The nonionic surfactant is preferably an aliphatic or cycloaliphatic alcohol, or a polyglycol ether derivative of a saturated or unsaturated fatty acid and an alkyl phenol, said derivative comprising 3 to 30 glycol ether groups, (aliphatic) The hydrocarbon portion contains 8 to 20 carbon atoms and the alkyl portion of the alkylphenol contains 6 to 18 carbon atoms.

Examples of nonionic surfactants are nonylphenol-polyethoxyethanol, castor oil polyglycol ether, polypropylene / polyethylene oxide adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxyethoxyethanol. Another suitable material is polyoxyethylene sorbitan, for example polyoxyethylene sorbitan triolate. The cationic surfactant preferably comprises at least one alkyl group having 8 to 22 carbon atoms as an N-substituent and a lower unsubstituted or halogenated alkyl group, a benzyl group or a lower hydroxyalkyl group as another substituent. And a quaternary ammonium salt.

The pesticidal compositions usually comprise from 0.1 to 99%, preferably from 0.1 to 95%, of the active ingredient of the formula I;
9% to 1%, especially 99.9 to 5% of solid or liquid additives and 0 to 25%, especially 0.1 to 25%
Surfactant. Although concentrated formulations are preferred as commercial products, end consumers generally use diluted compositions.

The composition also contains other additives, such as stabilizers, defoamers, viscosity modifiers, binders, tackifiers, fertilizers or other active ingredients, to achieve a particular effect. it can. Pharmaceutical preparations, ie compositions, preparations or formulations which comprise the compounds of the formula I with or without solid or liquid additives, can be prepared in a known manner, for example by adding the active ingredient to a bulking agent such as a solvent (mixture), a solid carrier and a suitable carrier. In this case, it is produced by uniformly mixing and / or pulverizing with a surfactant compound (surfactant).

A preferred method of applying the pesticidal composition containing the active ingredient of the formula I or at least one of these active ingredients is foliar application (foliar application). The frequency and amount of application depends on the risk of infection by the relevant pathogen. Nevertheless, the compounds of the formula I can be passed through the roots through the soil, either by immersing the plant growth in liquids or by applying them in the form of solids, eg granules, to the soil (soil application). It can also penetrate plants (penetration). In the case of paddy fields, such granules can be metered into flooded paddy fields. Alternatively, the compounds of the formula I can be applied (coated) to seeds by soaking the seeds in a solution of the active ingredient or by coating them with a solid preparation. In principle, propagations of any type of plant, such as seeds, roots or stems, can be protected by using compounds of formula I.

The compounds of the formula I are used pure or preferably with auxiliaries conventionally used in the formulation art. For the purposes of the present invention, those compounds of formula I are
Emulsion stock solution, coatable paste,
It is formulated into solutions that can be directly sprayed or diluted, diluted emulsions, wettable powders, dissolvable powders, powders, granules, and capsules filled with, for example, polymer substances. As with the nature of the composition, the method of application, such as spraying, atomizing, dusting, broadcasting, coating or pouring, is selected to suit the intended purpose and application environment.

The preferred application rate is usually 1 hectare (h
a) Active ingredient per (ai) 1g to 2kg ai / ha,
It is preferably from 25 g to 800 g ai / ha, particularly preferably from 50 g to 400 g ai / ha. When used as a seed coating, the active ingredient application rate is between 0.001 g and 1.0 g per kg of seed. The following examples are provided to further illustrate the present invention and are not intended to be limiting.

[0080]

EXAMPLES Production Examples Example H-1 :

Embedded image Preparation of hydroxylamine hydrochloride (1.32 g) in pyridine 20
5.2 g of methyl 3-methoxy-2-[([(3-oxo-2-butyl) imino] oxy) o-tolyl] acrylate in ml (EP-A-370629, No. 15)
Add to 6). After stirring the mixture at 30 ° C. for 6 hours, ice water is added, after a few hours the crystalline cake formed is filtered off and the crystals are washed with water. Recrystallization from ethanol / water gave methyl 3-methoxy-2-
[([(3-hydroxyimino-2-butyl) imino]
Oxy) o-tolyl] acrylate (4.8 g, compound N)
o. 1.73) as yellow crystals with a melting point of 104-107 ° C.

Example H-2:

Embedded image Preparation of In a pressure tube, 5 ml of dimethylformamide are added to 0.2 g of an approximately 65% sodium hydride suspension washed with hexane. Then, methyl = 3-methoxy-2-
[([(3-hydroxyimino-2-butyl) imino]
1.6 g of oxy) o-tolyl] acrylate and 1.1 g of 2,2,2-trifluoromethylethyl iodide
Is added. After the generation of hydrogen has ceased, the pressure tube is sealed. The mixture is then stirred at 50 ° C. for 5 hours. The reaction solution is then poured into ice water and extracted using ethyl acetate. And the product is put on silica gel,
Chromatograph using ethyl acetate / hexane (1: 3). As a result, 1.2 g of methyl 3-methoxy-2-[([(3- (2,2,2-trifluoroethoxyimino) -2-butyl) imino] oxy) o-tolyl] acrylate (Compound No. 1.74) as a colorless oil. ¹ H-NMR (CDCl ₃ ): chemical shifts of two imino-substituted methyl groups: 1.99 and 2.04 ppm.

Example H-3:

Embedded image Preparation of p-methylpropiophenone 1 in 30 ml of methanol
5.0 g and 20 ml of isopentyl nitrite are slowly added dropwise to 20 ml of sodium methylate (30% in methanol). After stirring the mixture for 5 hours, water 30
ml are added dropwise and the mixture is then acidified using acetic acid. The mixture was extracted using ethyl acetate, and the extract was washed with water, (Na ₂ SO ₄₎ dried and concentrated under reduced pressure. The residue is recrystallized from diethyl ether / n-hexane. As a result, α-
Hydroxyimino-4-methylpropiophenone is obtained as colorless crystals.

8.1 g of the compound obtained above in 40 ml of pyridine and 4.6 parts of O-methylhydroxylamine hydrochloride
g is refluxed for 1 hour. After adding toluene,
The mixture is concentrated under reduced pressure, treated with water and extracted using ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. Crystallizing α-hydroxyimino-4-methylpropiophenone = O-methyloxime from diethyl ether / n-hexane,
Obtained in the form of colorless crystals with a melting point of 156.degree.-157.degree.

1.87 g of the oxime obtained above and 2.58 g of methyl 2- (α-bromo-o-tolyl) -3-methoxyacrylate were combined with 0.5 ml of sodium hydride in 25 ml of N, N-dimethylformamide. Add to 41 g of suspension and stir the reaction mixture for 3 hours. It is then acidified using acetic acid, treated with water and extracted using ethyl acetate. The organic phase is washed twice using saturated sodium bicarbonate solution and once using saturated brine. After drying over anhydrous sodium sulfate,
The solvent is distilled off under reduced pressure. The compound of H-3 has a melting point of 98-
Crystallize from diethyl ether / n-hexane in the form of colorless crystals at 101 ° C. (Compound No. 1.117).

Example H-4:

Embedded image Preparation of 0.37 g of an approximately 65% sodium hydrogen suspension is washed with hexane and then 10 ml of dimethylformamide are added. Methyl 2- (2-bromomethylphenyl) glyoxylate = 2.59 g of O-methyloxime and 2-
2.42 g of (diphenylhydrazono) -3-hydroxyiminobutane are added to this suspension, and the mixture is then heated using a hot air blower to 40-50 g until vigorous evolution of hydrogen.
Heat to ° C. The mixture is then stirred for 1 hour under the exclusion of moisture and then poured into ice water. Extraction using ethyl acetate and chromatography on silica gel using ethyl acetate / hexane (1: 2) yielded methyl 2-[([(3-diphenylhydrazono-2-butyl) -imino] oxy. ) O-Tolyl] glyoxylate = O-methyloxime (Compound No. 2.19) 3.
7 g are obtained as a yellow oil. ¹ H-NMR (CDCl ₃ ):
Chemical shifts of two methyl groups substituted by imino groups: 1.64 and 2.12 ppm.

Example H-5:

Embedded image Preparation of methyl = 2-[({(3-diphenylhydrazono-2-
1.9 g of butyl) -iminodioxy) o-tolyl] glyoxylate = O-methyloxime were added at room temperature over 2 hours to 10 m
Stir in l. The excess of ethanol and excess methylamine is distilled off. The residue is taken up in diethyl ether, the solution is filtered and the filtrate is evaporated to dryness, leaving the product as a crystalline solid. After washing with hexane, N-monomethyl = 2-[({(3-diphenylhydrazono-2-
Butyl) -iminodioxy) o-tolyl] glyoxylamide = O-methyloxime 1.8 g (Compound No. 3.
19) is obtained as light yellow crystals with a melting point of 135-136 ° C.

Example H-6:

Embedded image 1- [4- (2,2-dichlorocyclopropylmethoxy) phenyl] propane-1,2-dione of the formula (AA) =
1.74 g of 1- (O-methyloxime) -2-oxime
Is added to 0.13 g of sodium hydride in 25 ml of N, N-dimethylformamide. Next, 1.5 g of methyl 2- (2-bromomethylphenyl) -3-methoxyacrylate of formula (BB) are added, and
Stir at room temperature for hours. The mixture is acidified using acetic acid and water and ethyl acetate are added. The aqueous phase was separated and the organic phase was separated using saturated sodium bicarbonate solution.
Wash twice and dry over anhydrous sodium sulfate. The solvent is evaporated under reduced pressure and the residue obtained is purified on silica gel using hexane / ethyl acetate (3: 1). The title compound is obtained as an oil. By column chromatography on silica gel (hexane: ethyl acetate = 3: 1 solution), isomer A, mp 86-88.
° C; isomer B, oil; isomer C, oil (compound 5.9).

Embedded image The following compounds are obtained analogously to this method or one of the methods described above; (abbreviations: Me = methyl, Et = ethyl, Δ = cyclopropyl, Ph = phenyl, mp = melting point). NMR: Chemical shift is CDCl
It is described as δ (ppm) in ₃ .

[0088]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

[Table 21]

[Table 22]

[Table 23]

[Table 24]

[Table 25]

[Table 26]

[Table 27]

[Table 28]

[Table 29]

[Table 30]

[Table 31]

[Table 32]

[Table 33]

[Table 34]

[Table 35]

2. Formulation example of active ingredient of formula I (% =% by weight)

Table 36: Hydration that the active ingredient mixture is thoroughly mixed with the auxiliaries, the mixture is thoroughly milled in a suitable mill and diluted with water to obtain a suspension of the desired concentration Agent is obtained.

2.2. Emulsion stock solution

[Table 37] Active ingredients in Table 1-7 10% Octylphenol polyethylene glycol 3% Ether (ethylene oxide 4-5 mol) Calcium dodecylbenzenesulfonate 3% Cyclohexanone 34% Xylene mixture 50% Dilute these stock solutions with water As a result, an emulsion having a desired concentration can be obtained.

2.3. Dust

The active ingredient is mixed with the carrier and the mixture is ground in a suitable mill to give a ready-to-use powder.

2.4. Extruded granules

Table 39 Active ingredients in Tables 1-7 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 87% The active ingredients are mixed with auxiliaries and milled, followed by wetting the mixture with water . The mixture is extruded and then dried in a stream of air.

2.5. Coated Granules

Table 40 Active ingredients in Tables 1-7 3% Polyethylene glycol (molecular weight 200) 3% Kaolin 94% The finely ground active ingredient mixture is applied to kaolin moistened with polyethylene glycol in a mixer. In this way, non-powder coated granules are obtained.

2.6. Stock suspension

[Table 41] Active ingredients in Table 1-7 40% Ethylene glycol 10% Nonylphenol polyethylene 6% Glycol ether (ethylene oxide 15 mol) Sodium lignosulfonate 10% Carboxymethylcellulose 1% 37% Formaldehyde aqueous solution 0.2% 75% aqueous Silicone oil in the form of an emulsion 0.8% Water 32% Suspension in which a finely ground active ingredient mixture can be homogeneously mixed with the auxiliaries and diluted with water to obtain a suspension of any desired concentration An agent stock solution is obtained.

[0095] 3. Biological Test Example A. Test Example B-1 for Microbicidal Action : Phytophthorainf on Tomato Plant
After periods cultivation of action a) Chibyo action Tomato plants so-called "Roter Gnom" 3 weeks for Estans), this tomato plants were sprayed with zoospore suspension of filamentous fungi and 18 to 20 ° C. and saturated atmospheric Keep the room warm in humidity. After 24 hours, wetting is interrupted. After drying the plants, a mixture containing the active ingredient formulated as a wettable powder is sprayed on at a concentration of 200 ppm of the active ingredient. After the spray coat has dried, the plants are returned to the moist chamber for 4 days. The number and size of typical leaf spots developed during this period were used to assess the activity of the test substance.

B) Application of the active ingredient formulated as a preventive osmotic wettable powder at a concentration of 60 ppm (in relation to soil volume) to the soil surface of three-week-old tomato plants, so-called "Roter Gnom", in pots I do. After leaving the plants for 3 days, the spore suspension of the tomato blight is sprayed under the foliage. The plants are then kept in a spray chamber at 18 to 20 ° C. and at a saturated atmospheric humidity. After this period, typical leaf spots grew and their number and size were used to assess the activity of the test substance. The untreated but infected control plants showed an infection rate of 100%, but the active ingredients of formula I in any of the above tables, in particular No. 1.
5, 1.24, 1.117, 2.24, 2.74 and 3.24 active ingredients reduced the infection rate to less than 20% in both tests.

Test Example B-2: Plasmopara on Grapes
Viticola (Plasmola viticola) (Bert. Et Curt) (Ber
l. growing in a greenhouse the action a) Residual preventive action "Chasselas" grape seed cuttings against et De Toni).
When they reach the 10-leaf stage, 3 plants are sprayed with the mixture (200 ppm of active ingredient). After the spray coat on the plant has dried, a spore suspension of the fungus is evenly sprayed under the leaves.
The plants are then placed in a moist box for 8 days. After this period, the symptom of the control plant develops clearly. The number and size of the lesions on the treated plants are used to test the activity of the test substance.

B) Curative action Grape cuttings of the species "Chasselas" are grown in a greenhouse.
When they reach the 10-leaf stage, the lower side of the leaves is inoculated with a spore suspension of Plasmopara viticola. After the plants have been placed in a moist box for 24 hours, the mixture of active ingredients (200 ppm of active ingredient) is sprayed. The plants are then placed in a moist box for a further 7 days. After this period, the symptom of the control plant develops clearly. The number and size of the lesions on the treated plants are used to test the activity of the test substance. Compared to control plants, the infection of plants treated with the active ingredients of the formula I is less than 20%.

Test Example B-3: Sugar beet (Beta vulg)
aris) Pythium debaryanum
Action on num) a) The fungus after soil application is grown on sterile oat kernels and added to a mixture of soil and sand. The inoculated soil is filled in a flower pot and seeds of sugar beet are sown. Immediately after sowing, the test preparations formulated as wettable powders are sprayed on the soil in the form of an aqueous suspension (20 ppm of active ingredient with respect to soil volume). The pots are then placed in a greenhouse at 20-24 ° C for 2-3 weeks. At all times, the soil is maintained at a uniform humidity by gently spraying water on the soil. When evaluating the test results, the germination of sugar beet plants and the ratio of healthy to diseased plants are measured.

B) The active bacteria after seed dressing are grown on sterile oat grains and added to a mixture of soil and sand. The inoculated soil is filled in a flower pot and seeds of sugar beet coated with a test preparation formulated as a seed dressing dust (1000 ppm active ingredient with respect to seed weight) are sown. The seed pots are placed in a greenhouse at 20-24 ° C for 2-3 weeks. The soil is maintained at a uniform humidity by gently spraying water on the soil. When evaluating the test results, the germination of sugar beet plants and the ratio of healthy to diseased plants are measured. The active ingredients of the formula I, in particular the compounds no. After treatment with 1.5, 1.24, 1.117, 2.24, 2.74 and 3.24, more than 80% of the plants germinate and show a healthy appearance. In control pots, a few plants germinate with an unhealthy appearance.

Test Example B-4: On peanuts (Groundnuts)
Cercospora alachidico
action on peanuts 10-15 cm high peanut plants are sprayed with the aqueous spray mixture (active ingredient 0.02%) until dripping, 48
After an hour, the conidia of the fungus are inoculated. The plants are incubated at 21 ° and high atmospheric humidity for 72 hours and then placed in a greenhouse until typical leaf spots have developed. The effect of the active ingredient is measured 12 days after inoculation based on the number and size of leaf spots.
The active ingredients of Formula I reduce leaf spots to less than about 10% of the leaf surface area. In some cases, the disease is completely reduced (degree of infection: 0-5%).

Test Example B-5: Yellow rust on wheat (Pucci
Effect on nia graminis) a) Residual protective action Six days after sowing, wheat plants are sprayed with an aqueous spray mixture (active ingredient: 0.02%) prepared from a test compound wettable powder until dripping. After 24 hours, the treated plants are infected with a suspension of fungus uredospores. The infected plants are incubated at 95-100% relative humidity and a temperature of about 20 ° C. for 48 hours before being placed in a greenhouse at about 22 ° C. Evaluation of the development of rust spots is made 12 days after infection.

B) Osmotic action 5 days after sowing, an aqueous spray mixture (active ingredient: 0.006%) is poured in the immediate vicinity of the wheat plants. Contact of the application mixture with the above-ground parts of the plants is carefully avoided. 48
After an hour, the treated plants are inoculated with a suspension of fungus uredospores. Insulation for 48 hours (conditions: 20 ° C. and relative humidity 95-1)
(00%) hours, the plants are placed in a greenhouse at 22 ° C. Inoculation 12
After a day, the development of rust spots is evaluated. Compounds of the formula I, in particular those of Table 1, in particular Compounds 1.5, 1.24 markedly reduce bacterial infection, in some cases down to 10-0%.

Test Example B-6: Potato disease on rice plant (Pyr
a) Residual protective action Rice plants were cultivated for 2 weeks, then sprayed with an aqueous spray mixture (active ingredient: 0.02%) and after 48 hours a suspension of conidia of the fungus Inoculate. After keeping at a relative atmospheric humidity of 95-100% and 22 ° C. for 5 days, the infection of the filamentous fungi is evaluated.

B) Osmotic action Two week old rice plants are watered with an aqueous spray mixture (0.006% of active ingredient, based on soil volume). Contact of the application mixture with the above-ground parts of the plants is carefully avoided. The pot is then filled with water to such an extent that the lowest part of the stem of the rice plant is submerged. After 96 hours, the drug-treated plants are inoculated with a suspension of conidia of the filamentous fungus, and the inoculated plants are then inoculated.
Incubate for 5 days at 95-100% relative humidity and a temperature of about 24 ° C. In many cases, the compounds of the formula I prevent the development of diseases on infected plants.

Test Example B-7: Scab on apple (Venturi
Residual protective action against a inaequalis) A dripping mixture (0.02% of active ingredient) is sprayed on fresh apple cuttings 10 to 20 cm long.
After a time, the treated plants are inoculated with a conidia suspension of the filamentous fungus.
The plants are then kept warm at 90-100% humidity for 5 days and kept in a greenhouse at 20-24 ° C. for another 10 days. The degree of scab infection is evaluated 15 days after inoculation. Most of the compounds of Formula I in one of Tables 1, 2 or 3 are:
Has a persistent effect on scab

Test Example B-8: Powdery mildew on barley (Erysi
Effect on phe graminis a) Residual protective action A barley plant of about 8 cm in height is dripped with an aqueous spray mixture (0.02% of active ingredient) and, after 3 to 4 hours, is sprinkled with conidia of the fungus. . The inoculated plants are left at about 22 ° C. in a greenhouse. Ten days after inoculation, the fungal infection is evaluated.

B) Osmotic action Immediately in the vicinity of a barley plant about 8 cm high, an aqueous spray mixture (0.002% of active ingredient with respect to soil volume) is poured. Contact of the application mixture with the above-ground parts of the plants is carefully avoided. After 48 hours, sprinkle the conidia of the filamentous fungus. The inoculated plants are left at about 22 ° C. in a greenhouse. Ten days after inoculation, the fungal infection is evaluated. Compounds of formula I, especially compound no. 1.117, 2.24 and 3.24 generally reduce disease to less than 20%, and in some cases even completely.

Test Example B-9: Powdery mildew on apple buds
(Podosphaera leucotricha) Residual protective action A spray mixture (about 0.06% of active ingredient) is sprayed on apple cuttings with fresh young shoots about 15 cm long. After 24 hours, the treated plants are inoculated with a suspension of conidia of the filamentous fungus and placed in a controlled-environment box at 70% relative atmospheric humidity and 20 ° C. The fungal infection is evaluated 12 days after inoculation. Formula I
Active ingredients reduce disease by 20% or less. Control plants show disease levels on the order of 100%.

Test Example B-10: Gray mold on apple (B
Action on otrytis cinerea)-Residual protective action The damaged part of the artificially damaged apple is treated by applying a spray mixture (active ingredient 0.02%) dropwise. The treated fruit is then inoculated with a spore suspension of the fungus and incubated for one week at high atmospheric humidity and about 20 ° C. An evaluation of the bactericidal action of the test compound is made by counting the number of lesions showing signs of spoilage. The active ingredients of the formula I reduce the spread of spoilage and in some cases can reduce it completely.

Test Example B-11: Helmint sporium
Against Gramineum (Helminthosporium gramineum)
The working wheat kernels are infected with a spore suspension of the fungus and dried. The infected grains are dressed with a suspension of the test compound (active ingredient; 600 ppm based on seed weight). Two days later, the seeds are placed on a suitable agar dish, and after another four days, the growth of the fungal colonies around the seeds is evaluated. The test substance is evaluated on the basis of the number and size of the fungal colonies. An excellent effect, namely the suppression of fungal colonies, is observed in some cases with the compounds of the formula I.

Test Example B-12: Collection on Cucumber
Against Colletotrichumlagenarium
The growing cucumber plants are grown for 2 weeks and the spray mixture (concentration:
(0.002%). Two days later, the plants are infected with a fungal spore suspension (1.5 × 10 5 spores / ml) and incubated at 23 ° C. and high atmospheric humidity for 36 hours. Thereafter, the incubation is continued at normal humidity and a temperature of about 22-23 ° C. Infection of the generated bacteria is evaluated 8 days after inoculation. Untreated but infected control plants show 100% fungal infection. Substantially complete suppression of infection by the disease is in some cases achieved by the compounds of the formula I, in particular Indicated by compounds 1.5 and 3.24.

Test Example B-13: Fusarium on Rye
Effect on Fusarium nivale Rye of the species "Tetrahell" infected with Fusarium nivale is coated with a test fungicide using a mixing roll, the concentration is as follows: active ingredient (ai) ₂₀ or 6 ppm
(In terms of seed weight). Infected and treated rye is pierced and sown in the field in October using a seed punch (3 repeats per concentration, 3 m plot of 6 seed furrows). Test plants are grown under normal field conditions (preferably in areas that are completely covered with snow during winter) until infection is assessed. To assess phytotoxicity, seed germination is scored in the fall and the number of plants per unit area and the number of chicks per plant in the spring. To measure the activity of the active ingredient, the number of plants infected with Fusarium
Count immediately after the snow melts. In the case of the present invention, the number of infected plants is less than 5%. The germinated plants have a healthy appearance.

Test Example B-14: Septoram on Wheat
Action on Nodrum (Septoria nodorum) A spray mixture (60 ppm of the active ingredient) prepared using a wettable powder of the active ingredient (2.8: 1) is sprayed on wheat plants at the third leaf stage. After 24 hours, a conidia suspension of the filamentous fungus is inoculated. The plants are then kept at 90-100 relative humidity for 2 days.
% And kept at 20-24 ° C. for a further 10 days. After inoculation, the fungal infection is evaluated. Less than 1% of the wheat plants were infected.

Test Example B-15: Mongare disease on rice (Rhi
Action against zoctonia solani) Protection by local treatment of soil Soil surrounding 10-day-old rice plants was flooded with a suspension prepared with the formulated test substance, so that the above-ground parts of the plants did not come into contact with the suspension. I made it. Three days later, the plants were inoculated by placing straws of barley infected with Mongare disease between rice plants in each pot. 29 ° C during the day
And 26 ° C at night and 95% relative humidity
After incubation in an environmental box for 6 days, the fungal infection is evaluated.
Less than 5% of rice plants are infected. The plants had a healthy appearance.

Protection by Local Leaf Treatment 12 day old rice plants are sprayed with a suspension prepared using the formulated test substance. One day later, inoculation is carried out by placing barley straw infected with Mongare disease between rice plants in each pot. The plants are scored after 6 days of incubation in a controlled-environment box at 29 ° C. during the day and 26 ° C. at night and 95% relative humidity. Untreated but inoculated control plants showed 100% fungal infection.
The compounds of the formula I are in some cases responsible for completely preventing infection by disease.

B. Insecticidal Action Test Example B-16: Aphis crasivora
ccivora) Infects Hidden Bean Saplings with Efficicus clacivora,
The spray mixture containing the active ingredient at 400 ppm is then sprayed on and kept warm at 20 ° C. The percentage reduction in population (% effect) is determined after 3 and 6 days by comparing the number of dead aphids on treated plants to that on untreated plants. In this test, the compounds in Tables 1 to 7 have excellent effects. In particular, Compound No. 4.5 isomer 1 has more than 80% action.

Test Example B-17: Diablotica Baltea
Effects of Dia-brotica balteata on larvae Corn seedlings are sprayed with an aqueous emulsion spray mixture containing 400 ppm of the active substance. After the spray film has dried,
The rice plants are inhabited by ten second instar larvae of Diabrotica barteata and then placed in plastic containers. The percentage reduction in population (% activity) is determined after 6 days by comparing the number of surviving larvae on the treated plants with that on the untreated plants. In this test, the compounds in Tables 1 to 7 have excellent effects. In particular, Compound No. 1.5,
1.24, 2.24, 3.24, 4.5, Isomer 1, 4.14, Isomer 1, 4.
117, both isomers, 4.121, 4.170, 5.9, isomers 1 and 5.
51, Isomer 1 has more than 80% action.

Test Example B-18: Heliotis villasse
To larvae (caterpillars) of Heliosthis virescens
Youth plant action soybean against, delivered a spray mixture turbid aqueous milk containing the active ingredient in 400 ppm. After the spray film has dried, the first stage larvae of Heliotis virensens (cat
erpillars) and place in plastic containers. The rate of reduction of the population or of the damage to the plant (% activity) is determined after 6 days by comparing the number of dead larvae on the treated plants and the extent of the damage to that on the untreated plants. In this test, the compounds of Tables 1 to 7 show excellent effects. In particular, Compound No. 4.5, Isomer 1, 4.14, Isomer 1, 4.18, 4.117, both isomers, 4.121, 5.9, Isomer 1 and 5.52, Isomer 1 have more than 80% activity.

Test Example: B-19: Spodoptera lithola
Action on squirrels (Spodoptera littoralis) Young soybean plants are sprayed with an aqueous emulsion spray mixture containing 400 ppm of the active ingredient. After the spray film has dried, the soybean plants are treated with Spodoptera litoralis.
Inhabit 10 individuals of the third stage larvae (caterpillars) of s) and then place them in plastic containers. The rate of reduction of the population or the rate of feeding damage (% activity) is determined after 3 days by comparing the number of dead larvae on the treated plants and the degree of feeding damage to that on the untreated plants. In this test, the compounds of Tables 1 to 7 show excellent effects. In particular, compound No.1.
5, 1.24, 2.24, 3.24, 4.18, 4.5, Isomer 1, 5.9, Isomer 1 and 5.52, Isomer 1 have more than 80% activity.

C. Acaricidal activity test example B-20: Tetranych
Action on U. urticae) Young plants of Hiramoto bean were inoculated with a mixed system of Tetranicas urticae , and after one day an aqueous emulsion spray mixture containing 400 ppm of the test compound was sprayed, and the treated plants were then sprinkled with 25
C. for 6 days and then evaluated. The percentage reduction (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with those on the untreated plants. In this test, the compounds of Tables 1 to 7 show excellent effects. In particular, compound No. 1.5, 1.24, 2.24, 3.24, 4.5, isomer 1, 4.14, isomer 1, 4.117, both isomers, 5.9, isomer 1 and 5.52, isomer 1 have an activity of more than 80% have.

Test Example B-21: Buchirth microp
Action on lass (Boophilus microplus) The adult female mites that have been fully sucked are placed on a PVC board and covered with absorbent cotton. For treatment, 10 ml of an aqueous test solution containing 125 ppm of the active ingredient are sprayed on the mites. The absorbent cotton is then removed and the treated mites are kept warm for 4 weeks until they lay eggs. The effect is clearly indicated in both cases as mortality and infertility in the case of female worms or as ovicidal effects in the case of eggs.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07C 317/32 C07C 317/32 317/44 317/44 323/47 323/47 C07F 7/10 C07F 7 / 10H (72) Inventor Zalem Farouk Zeha-4422, Switzerland Alicedorf, Kirch-Ackerstraße 27 (72) Inventor Rene Zurfleu, Zeha-4052 Switzerland, Basel, ST. Alban Rheinweg 180

Claims (42)

[Claims] 1. A compound of the formula I Wherein, X is and represents a CH Y represents OR _11; and further wherein, R ₁₁ represents an alkyl group of 1 to 4 carbon atoms; R ₁₂
And R ₁₃ are each independently a hydrogen atom or a carbon atom
A represents an O atom or a group: NR
₄ represents; R ₁ is alkyl of 1 to 4 carbon atoms,
Halo-C 1 -C 4 alkyl, cyclopropyl, cyano or methylthio; R ₂ is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl Group, And the D groups are the same or different and are each a halogen atom,
An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms, an alkenyloxy having 3 to 6 carbon atoms A alkynyloxy group having 3 to 6 carbon atoms, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group; n represents 1, 2, 3 or 4; 2,3
Or 4; Z represents -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O-, -S (O) _m -,- -S (alkyl having 1 to 4 carbon _{atoms) (O) m -, -} S (O) m - ( alkyl having 1 to 4 carbon atoms) -, represents; m is 0,
B represents an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 2 To 6 alkenyl groups or (C 2
Alkynyl) -C 1 -C 2 alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or an aryl or heterocyclic group ( These two are independently unsubstituted or C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, halogen, C 1 -C 6 alkoxy or Halo-mono- or penta-substituted by an alkoxy group having 1 to 6 carbon atoms) or a group represented by the following formula: Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom, and p is 0, 1, R ₃ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 to 5
C 1 -C 6 haloalkyl having 1 halogen atom, (C 1 -C 4 alkoxy) -C 1 -C 2 alkyl, (C 2 -C 4 alkenyl) -C An alkyl group of 1 to 2 (which is unsubstituted or substituted by 1 to 3 halogen atoms), (2 to 4 carbon atoms)
Alkynyl) -alkyl group having 1 or 2 carbon atoms,
C3 -C6 cycloalkyl, which is unsubstituted or substituted by 1 to 4 halogen atoms, (C3 -C6 cycloalkyl)-C1 -C6 4 alkyl groups (which are unsubstituted or substituted by 1 to 4 halogen atoms), cyano-alkyl groups having 1 to 4 carbon atoms; (alkoxy having 1 to 4 carbon atoms) carbonyl An alkyl group having 1 to 2 carbon atoms, (alkoxy having 1 to 4 carbon atoms) carbamoyl-1 carbon atom
Or 2 alkyl groups, phenyl-C 1-3 alkyl group (which is unsubstituted or halogen atom, C 1-3 alkyl group, C 1
Substituted by an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group or an alkylenedioxy group having 1 to 4 carbon atoms, and the phenyl group is simply substituted by the same or different substituents. It can be substituted or trisubstituted. ); 1 carbon atom
Monosubstituted or independently by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a haloalkyl group having 1 to 3 carbon atoms having 1 to 3 halogen atoms, a nitro group or a cyano group. Represents a disubstituted phenyl group; R ₄ represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or R ₃ and R ₄ together with the nitrogen atom to which they are attached are saturated. Or an unsaturated 5- to 7-membered ring, wherein the ring is unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms, and an additional heterocyclic group selected from N, O and S Which can have 1 to 3 atoms). (Including isomers and mixtures thereof). 2. X represents CH; Y represents OCH ₃ ;
Represents an O atom or a NR ₄ group; R ₁ represents an alkyl group having 1 to 4 carbon atoms, a halo-alkyl group having 1 to 4 carbon atoms, a cyclopropyl group, a cyano group or a methylthio group; ₂ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, And the D groups are the same or different and are each a halogen atom,
An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 2 carbon atoms, a haloalkoxy group having 1 to 2 carbon atoms, an alkenyloxy having 3 to 6 carbon atoms A alkynyloxy group having 3 to 6 carbon atoms, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group; n represents 1, 2, 3 or 4; 2,3
Or 4; Z represents -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O-, -S (O) _m -,- -S (alkyl having 1 to 4 carbon _{atoms) (O) m -, -} S (O) m - ( alkyl having 1 to 4 carbon atoms) -, represents; m is 0,
B represents an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 2 To 6 alkenyl groups or (C 2
Alkynyl) -C 1 -C 2 alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or an aryl or heterocyclic group, Or an aryl group or a heterocyclic group (each of which is independently an alkyl group having 1 to 6 carbon atoms, a halo-alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms) Or a mono- or penta-substituted halo-alkoxy group having 1 to 6 carbon atoms) or a group: Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom, and p is 0, 1, R ₃ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms having 1 to 5 halogen atoms, 1
(C4 -C4 alkoxy) -C1 -C2 alkyl, (C2 -C4 alkenyl) -C1 -C2 alkyl (unsubstituted or C1 -C3 alkyl) (Substituted by a halogen atom), (alkynyl having 2 to 4 carbon atoms)-an alkyl group having 1 to 2 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, which is unsubstituted or 1 (C3-C6 cycloalkyl) -C1-C4 alkyl (unsubstituted or substituted by 1-4 halogen atoms) ), Cyano-
C1 -C4 alkyl; (C1 -C4 alkoxy) carbonyl-C1 -C2 alkyl, phenyl-C1 -C3 alkyl (unsubstituted Or a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, an alkylene dialkyl having 1 to 4 carbon atoms. Substituted by an oxy group and the phenyl group can be mono- or tri-substituted by the same or different substituents);
An alkyl group, an alkoxy group having 1 to 4 carbon atoms,
Halogen atoms, one to three 2 haloalkyl groups C 1 -C having halogen atom, a phenyl group by a nitro group or a cyano group which is mono- or independently disubstituted; R ₄ is the number of carbon atoms Represents 1 to 4 alkyl or phenyl groups, or R ₃ and R ₄ together with the nitrogen atom to which they are attached are a saturated or unsaturated 5- to 7-membered ring (this ring may be Is substituted or substituted by an alkyl group having 1 to 4 carbon atoms,
2. The compound of formula I according to claim 1, wherein the compound of formula I forms one to three additional heteroatoms selected from N, O and S). 3. A is an oxygen atom, NCH ₃ or nC ₆ H ₅
3. A compound of formula I according to claim 2, which represents 4. A compound of formula I according to claim 2, wherein R ₁ represents a methyl, cyclopropyl or cyano group. 5. A compound of formula I according to claim 2, wherein R ₂ represents an alkyl group having 1 to 4 carbon atoms or a cyclopropyl group. 6. R ₂ is a group: D represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, 1
C1 to C2 alkyl, C1 to C2 haloalkoxy, C3 to C6 alkenyloxy, C3 to C6 substituted by 5 to 5 halogen atoms 3. A compound of formula I according to claim 2, wherein alkynyloxy, C1 -C4 alkylenedioxy, cyano or nitro are represented; n is 1, 2, 3 or 4. 7. R ₂ is a group: And Z is -O-, -O- (alkyl having 1 to 4 carbon atoms)-,-(alkyl having 1 to 4 carbon atoms) -O-, -S (O) ₂ -,- (C 1 -C 4 alkyl) -S (O) ₂ -, - S (O) ₂ - (alkyl of 1 to 4 carbon atoms) -, a compound of formula I according to claim 2, wherein represents a. 8. R ₂ is a group: And B represents an alkyl group having 1 to 4 carbon atoms, a halogen-alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms or (2 to 4 carbon atoms) Alkynyl) -C 1
Or 2 alkyl groups, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or an aryl group, or an alkyl group having 1 to 2 carbon atoms, a halo-carbon Represents an aryl mono- or independently disubstituted by an alkyl group having 1 or 2 atoms, a halogen atom, an alkoxy group having 1 to 2 carbon atoms or a halo-alkoxy group having 1 to 2 carbon atoms, or Group: Wherein R ₅ , R ₆ , R ₇ , R ₈ and R ₉ independently represent a hydrogen atom, an alkyl group having 1 to 2 carbon atoms or a halogen atom, and p is 0, 1, 3. A compound of formula I according to claim 2, which represents 2 or 3. 9. The compound of formula I according to claim 2, wherein R ₂ is a phenyl group substituted at the 4-position by -ZB. 10. R ₃ is a hydrogen atom, an alkyl group or one to three C 1 -C having halogen atoms of from 4 haloalkyl group having from 1 to 6 carbon atoms, (C 1 -C to 2 alkoxy) -C1 -C2 alkyl, (C1 -C4 alkoxy) -carbonyl -C1 -C2 alkyl, unsubstituted or substituted by C1 -C3 halogen A propenyl group, a propargyl group, a cycloalkyl group having 3 to 6 carbon atoms, a cyclopropylmethyl group which is unsubstituted or substituted by 1 to 2 halogen atoms, a cyano-alkyl group having 1 to 2 carbon atoms, Phenyl-alkyl having 1 to 2 carbon atoms, which is unsubstituted or halogen, methyl, methoxy or 1 to 3 halo; A phenyl group may be mono- or di-substituted by the same or different substituents); a halogen atom, a methyl group, a methoxy group, 1-3. Represents a phenyl group which is mono- or independently di-substituted by a halomethyl group, a cyano group or a nitro group having three halogen atoms; or R ₃ and R ₄ together with the nitrogen atom to which they are attached A saturated or unsaturated 5- to 7-membered ring, which ring is unsubstituted or substituted by C1 -C4 alkyl,
3. The compound of formula I according to claim 2, which forms 1 to 3 additional heteroatoms selected from and S. 11. The compound of formula I according to claim 2, wherein R ₄ represents a methyl group or a phenyl group. 12. Y represents OCH ₃ ; R ₁ represents CH ₃ ; A represents an oxygen atom; R ₂ represents 4-methylphenyl group or 4-allyloxyphenyl group or 4- (3-trifluoro A methyl-benzyloxy) phenyl group or 4-
Represents (2,2-dichloro-cyclopropylmethoxy) phenyl group; and Formula I R ₃ is according to claim 1, wherein representing the CH ₃
Compound. 13. X represents CH; Y represents OCH ₃ ;
A represents an O atom or a NR ₄ group; R ₁ represents an alkyl group having 1 to 4 carbon atoms, cyclopropyl group, cyano group or methylthio group; R ₂ represents a hydrogen atom, 1 carbon atom
To 6 alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms; halogen atoms, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 2 carbon atoms, A haloalkoxy group having 1 to 2 carbon atoms, an alkenyloxy group having 3 to 6 carbon atoms, an alkynyloxy group having 3 to 6 carbon atoms, an alkylenedioxy group having 1 to 4 carbon atoms, a cyano group or a nitro group Represents a phenyl group which is monosubstituted or independently disubstituted by R ₃ is a hydrogen atom,
An alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 6 carbon atoms having 1 to 5 halogen atoms; (alkoxy having 1 to 4 carbon atoms) -alkyl group having 1 to 2 carbon atoms; (2 to 4 carbon atoms
Alkenyl) -alkyl group having 1 to 2 carbon atoms (which is unsubstituted or substituted by 1 to 3 halogen atoms), (alkynyl having 2 to 4 carbon atoms) -carbon atom 1 to 2 alkyl groups; C3 to C6 cycloalkyl groups which are unsubstituted or substituted by 1 to 4 halogen atoms, (C3 to C6 cycloalkyl groups) )-An alkyl group of 1 to 4 carbon atoms, which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-an alkyl group of 1 to 4 carbon atoms; 1-4 alkoxy) carbonyl-C 1-2 alkyl, phenyl-C 1-3 alkyl (unsubstituted or halogen, Substituted by an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, and an alkylenedioxy group having 1 to 4 carbon atoms. And the phenyl group may be mono- or tri-substituted by the same or different substituents.); An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, halogen atom, 1 to represent the three 1 -C having halogen atoms 2 haloalkyl group, a nitro group or a cyano group by a single substituted or independently disubstituted by which the phenyl group; R ₄ is C 1 -C to either an alkyl group or a phenyl group 4, or R ₃ and R ₄ are saturated or unsaturated 5- to 7-membered together with the nitrogen atom to which they are attached (This ring is unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms and can have 1 to 3 additional heteroatoms selected from N, O and S) A compound of formula I according to claim 1 which forms 14. A represents O or N-R _4; R ₁ represents a methyl group, a cyclopropyl group or a methylthio group; R ₂
Is a methyl group, a cyclopropyl group; a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a carbon atom having 1 to 2 carbon atoms which is substituted by 1 to 5 halogen atoms. Alkyl group, haloalkoxy group having 1 to 2 carbon atoms, alkenyloxy group having 3 to 6 carbon atoms, alkynyloxy group having 3 to 6 carbon atoms, alkylenedioxy group having 1 to 4 carbon atoms, cyano group Or a phenyl group monosubstituted or independently disubstituted by a nitro group; and wherein R ₃ is as described in Formula I and R ₄ represents a methyl group or a phenyl group; Or R ₃ and R ₄ together with the nitrogen atom to which they are attached form pyrrolidine,
Piperidine, morpholine, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole,
14. A compound of formula I according to claim 13, which represents either 1,2,4-triazole or 1,2,3-triazole. 15. A represents an O atom; R ₁ represents a methyl group; R ₂ represents a methyl group; a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, 1 C1 to C2 alkyl, C1 to C2 haloalkoxy, C3 to C6 alkenyloxy, C3 to C6 substituted by 5 to 5 halogen atoms R ₃ represents an alkynyloxy group, a C 1 -C 4 alkylenedioxy group, a cyano group or a phenyl group mono- or independently di-substituted independently by a nitro group; and R ₃ represents a C 1 -C 6 alkyl. 14. A compound of formula I according to claim 13, which represents a group. 16. R ₁ represents a methyl group; R ₂ represents a methyl group; R ₃ is as described in claim 1; and R ₄ represents a methyl group or a phenyl group; ₃ and R
₄ is a saturated or unsaturated 5- to 7-membered ring together with the nitrogen atom to which they are attached, which ring is unsubstituted or substituted by C1 -C4 alkyl. 14. A compound of formula I according to claim 13 which forms one to three additional heteroatoms selected from N, O and S). 17. R ₃ is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, C 1 -C having 1 to 3 halogen atoms to 4 haloalkyl group; (carbon atoms 1
C2 -C2 alkoxy) -C1 -C2 alkyl group; unsubstituted or substituted by C1 -C3 halogen atom, propenyl group, propargyl group, C3 -C6 cycloalkyl group; Replacement or 1
(C3-C6 cycloalkyl) methyl, cyano-C1-C2alkyl, (C1-C2)
Or 2 alkoxy) carbonyl-C 1-2 alkyl; phenyl-C 1-2 alkyl, which is unsubstituted or halogen,
A methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group, a nitro group or an alkylenedioxy group having 1 to 2 carbon atoms, wherein the phenyl group is the same or different. Can be monosubstituted or disubstituted. ); Halogen atom, a methyl group, a methoxy group, one to a halomethyl group having three halogen atoms, a phenyl group by a cyano group or a nitro group is disubstituted monosubstituted or independently; R ₄ is a methyl group Or a phenyl group; or R ₃
And R ₄ together with the nitrogen atom to which they are attached, are saturated or unsaturated, 5- to 7-membered rings, which are unsubstituted or substituted by C 1 -C 4 alkyl groups. 14. The compound of formula I according to claim 13, wherein the compound has 1 to 3 additional heteroatoms selected from N, O and S). 18. R ₃ and R ₄ together with the nitrogen atom to which they are attached form a triazolyl, morpholinyl, 2,6-dimethylmorpholinyl, azepinyl,
18. A compound of formula I according to claim 17, which represents a piperidyl or pyrrolidinyl group. 19. A represents an O atom; R ₁ represents a methyl group; R ₂ represents a methyl group; a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, 1 C1 to C2 alkyl, C1 to C2 haloalkoxy, C3 to C6 alkenyloxy, C3 to C6 substituted by 5 to 5 halogen atoms Alkynyloxy, C 1 -C 4 alkylenedioxy, phenyl which is monosubstituted or independently disubstituted by cyano or nitro; and R ₃ is hydrogen, C 1 -C 4 4 alkyl groups, 1 to 3
C 1 -C 4 haloalkyl group having 1 halogen atom; (C 1 -C 2 alkoxy) -C 1 -C 2 alkyl group; unsubstituted or substituted by 1 to 3 halogen atoms A propenyl group, a propargyl group, a C3-C6 cycloalkyl group; an unsubstituted or substituted (C3-C6 cycloalkyl) methyl group by one or two halogen atoms, Cyano-C1 -C2 alkyl, (C1 -C2 alkoxy) carbonyl-C1 -C2 alkyl; phenyl-C1 -C2 alkyl (unsubstituted Or a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group, a nitro group or a carbon atom A phenyl group may be mono- or disubstituted by the same or different substituent (s), and may be substituted by an alkylenedioxy group having 1 or 2 atoms); a halogen atom, a methyl group, a methoxy group 14. The compound of formula I according to claim 13, which represents a phenyl group mono- or independently di-substituted by a halomethyl group, a cyano group or a nitro group having 1 to 3 halogen atoms. A represents an O atom; R ₁ represents a methyl group; R ₂ represents a methyl group; mono-substituted or independently by a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group. 20. The compound of formula I according to claim 19, wherein R ₃ represents a phenyl group which is disubstituted; and R ₃ represents a methyl group. A represents NCH ₃ ; R ₁ represents a methyl group; R ₂ represents a methyl group; mono-substituted or independently by a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group. R ₃ is a methyl group; a halogen atom, a methyl group, a methoxy group, a halomethyl group having 1 to 3 halogen atoms, a cyano group or a nitro group; 14. The compound of formula I according to claim 13, which represents a disubstituted phenyl group. 22. The compound of formula I according to claim 1, wherein the double bond where X = C is in E-form. 23. A process for the preparation of a compound of formula I according to claim 1, wherein Y represents N (R ₁₂ ) R ₁₃ to prepare a compound of formula I: The formula I represents OR ₁₁
The compound of formula (1) was mixed with HN (R ₁₂ ) R ₁₃ in a solvent at 0 ° C to 40 ° C.
How to react. 24. A process for the preparation of a compound of formula I according to claim 1, wherein X, Y, A and R ₁ to R ₃ are
To prepare a compound of formula I defined the same as defined for (and where R ₃ is not a hydrogen atom): (Wherein A and R ₁ to R ₃ are defined as above)
An oxime represented by the general formula: Wherein X and Y are defined as above and U is a leaving group, and an inert solvent in the presence of a base and in the presence or absence of a phase transfer catalyst. At 0 to 50 ° C. 25. A process for the preparation of a compound of formula I according to claim 1, wherein A represents an oxygen atom and X, Y
To prepare a compound of formula I wherein R ₁ and R ₃ are as defined for formula I: (Where X, Y, R ₁ and R ₂ are defined as above)
An oxime represented by the formula V is represented by the formula V—R ₃ V wherein R ₃ is defined as defined for formula I and U is defined as defined for formula III ( And in that case, R ₃ is neither a hydrogen atom nor a phenyl group)]. 26. A process for preparing a compound of formula I according to claim 1, wherein X, Y, R ₁ and R ₂ are defined as defined for formula I. To prepare a compound of formula VI (Where X, Y, R ₁ and R ₂ are defined as above)
A hydroxylamine or a salt thereof in a solvent at 0 ° C to 50 ° C. 27. A composition for controlling pests comprising the compound according to claim 1 as an active ingredient. 28. The active ingredient according to claims 2 to 12
28. The composition according to claim 27, comprising a compound according to any one of the preceding claims. 29. The active ingredient according to claim 13 or 2
28. The compound according to any one of claims 1 to 27.
A composition as described. 30. The composition according to claim 27, comprising the compound according to claim 22 as an active ingredient. 31. The composition according to claim 27, wherein the pest is a plant-pathogenic microorganism. 32. The composition according to claim 31, wherein the microorganism is a fungus. 33. The composition according to claim 27, wherein the pest is an insect or a tick. 34. A method for controlling or preventing pests, comprising applying the compound according to claim 1 to or around pests. 35. The method according to claim 34, wherein the compound according to any one of claims 2 to 12 is applied. 36. The method according to claim 34, wherein the compound according to any one of claims 13 to 21 is applied. 37. The method according to claim 34, wherein the compound according to claim 22 is applied. 38. The method according to any one of claims 34 to 37, wherein the pest is a plant pathogenic microorganism. 39. The method according to claim 38, wherein the microorganism is a fungus. 40. The method according to claim 34, wherein the pest is an insect or a tick. 41. The seed is treated.
8. The method according to any one of items 7 to 7. 42. Seed treated according to the method of claim 41.