ES2162633T5 - PESTICIDES - Google Patents

Abstract

The invention relates to imino-alkyl-imino-oxy-tolyl derivatives having the formula (I): and to the isomers thereof, as well as to mixtures of said isomers, to the processes for their preparation, to the composition and method for pest control and prevention.

Description

Pesticides

The invention relates to new compounds with Pesticide action of formula I:

one

and its possible isomers and mixtures of isomers, in where:

to)

X is an atom of N e

Y is OR_ {11} or N (R 12) R 13 or

b)

X is CH e

And it is OR_ {11}

and where also:

R 11 is 1-4C alkyl;

R 12 and R 13 are independently hydrogen or 1-4C alkyl;

A is an O atom or the group NR4;

R1 is alkyl 1-4C, halo-alkyl 1-4C, cyclopropyl, cyano or methylthio;

R2 is a group

2

or a group;

3

D radicals are identical or different and are 1-4C alkoxy, 1-2C haloalkoxy, 3-6C alkyloxy, alkylenedioxy
1-4C;

n is 0, 1, 2, 3 or 4;

Z is - (alkyl 1-4C) -O, -S (O) m, -(I rent 1-4C) -S (O) m or -S (O) m (1-4C alkyl) -,

m is 0, 1 or 2;

B is halo-alkyl 1-6C, cycloalkyl 3-6C or alkenyl 2-6C or alkynyl (2-4C) alkyl 1-2C, each of which is unsubstituted or substituted by 1 to 3 halogen atoms; or is aryl, or heterocyclyl, where each of the two independently is unsubstituted or substituted by one to five substituents selected from alkyl 1-6C, halo-alkyl 1-6C, halogen, alkoxy 1-6C or halo-alkoxy 1-6C, or is a group

4

or trimethylsilyl;

R 5, R 6, R 7, R 8, and R 9 independently of each other, they are each hydrogen, alkyl 1-4C or halogen;

Y

p is 0, 1, 2 or 3;

R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, (1-4C) alkoxycarbamoyl-alkyl 1-2C, phenyl-alkyl 1-3C which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or by alkylenedioxy 1-4C, being possible that the group phenyl is mono- to tri-substituted by substituents identical or different; phenyl that is unsubstituted or substituted by one or two independently selected substituents between 1-4C alkyl, 1-4C alkoxy, halogen, halo-alkyl 1-2C which it has 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 halogen, nitro or cyano atoms;

R 4 is 1-4C alkyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S.

The compounds according to the invention they have fungicidal, acaricidal and insecticidal properties and are appropriate as active ingredients for use in agriculture, in horticulture and in the hygiene sector.

The invention also relates to a procedure for the preparation of the compounds according to the invention, with fungicidal compositions, acaricides and insecticides containing such compounds as ingredients assets, as well as with the use of such compounds and compositions in the control of phytopathogenic fungi, mites and insects and in the prevention of attacks by such organisms.

When in the compounds of formula I are asymmetric carbon atoms present, the compounds are presented in optically active form. Simply based on the presence of the aliphatic double bonds, the oximino and the hydrazono, the Compounds will be presented in each case in the forms [E] and / or [Z]. In addition, atropisomería may also occur. The formula I intends to understand all these possible isomeric forms as well as their mixtures, for example racemic mixtures and any mixtures [E / Z].

WO 90/07493 describes methyl esters of aldimino acid and cetimino-oxy-ortho-tolylacrylic as fungicides, which are structurally different from those compounds of the present invention.

The general terms used previously and which will be used below have the following meanings unless they are defined in some other way.

Halogen represents fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, first of all fluorine or chlorine.

Alkyl is straight chain, for example methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl or of branched chain, for example isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, Neopentyl or isohexyl.

Alkenyl is straight chain alkenyl or branched, such as vinyl, 1-methylvinyl, allyl, 1-butenyl or isopropenyl, especially ally

Alkynyl represents, for example, ethynyl, 1-propynyl or 1-butynyl, especially propargyl.

Under cycloalkyl is meant cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Halogen substituted groups, such as haloalkyl and haloalkoxy, may be partially or completely halogenated by identical or different halogen substituents. Examples of haloalkyl are methyl which is mono- or trisubstituted. by fluorine, chlorine and / or bromine, such as CHF2, CF3 or CH 2 Cl; ethyl which is mono- to pentas substituted by fluorine, chlorine and / or bromine, such as CH 2 CF 3, CF 2 CF 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, CF 2 CHClF, CF 2 CHBrF or CClFCHClF; very particularly prefers trifluoromethyl.

Linear chain alkylenedioxy 1-4C represents -O-CH2 -O-, -O-CH2CH2 -O-, -O-CH2CH2CH2- O- or -O-CH 2 CH 2
CH 2 -CH 2 -O-.

Aryl represents, for example, phenyl or naphthyl, preferably phenyl.

The term heterocyclyl represents a ring aromatic or non-aromatic 5 to 7 members containing 1 to 3 heteroatoms selected from N, O or S. Rings are preferred 5 and 6 member aromatics that have a nitrogen atom as heteroatom and, if appropriate, another heteroatom, preferably nitrogen or sulfur, in particular nitrogen.

The 5 to 7 member rings that are formed by the radicals R 3 and R 4 together with the atom of nitrogen, to which they are attached, especially include pyrrolidine,  piperidine, morpholine, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, isoxazole, oxazole, isoxazolidine, oxazolidine, thiazole, isothiazole, thiazoline e isothiazolidine.

Within the scope of the invention, prefer:

(1) Compounds of formula I where:

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also:

A is an O atom or the group NR4;

R1 is alkyl 1-4C, halo-alkyl 1-4C, cyclopropyl, cyano or methylthio;

R2 is a group

5

or a group

6

D radicals are identical or different and are 1-4C alkoxy, 1-2C haloalkoxy, 3-6C alkyloxy, alkylenedioxy
1-4C;

n is 0, 1, 2, 3 or 4;

Z is - (alkyl 1-4C) -O, -S (O) m, -(I rent 1-4C) -S (O) m - or -S (O) m (1-4C alkyl) -,

m is 0, 1 or 2;

B is halo-alkyl 1-6C, cycloalkyl 3-6C or alkenyl 2-6C or alkynyl (2-4C) alkyl 1-2C, each of which is unsubstituted or substituted by 1 to 3 halogen atoms; or is aryl, or heterocyclyl, where each of the two independently is unsubstituted or substituted by one to five substituents selected from alkyl 1-6C, halo-alkyl 1-6C, halogen, alkoxy 1-6C or halo-alkoxy 1-6C, or is a group

7

R 5, R 6, R 7, R 8, and R 9 independently of each other, they are each hydrogen, alkyl 1-4C or halogen;

Y

p is 0, 1, 2 or 3;

R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy 1-2C alkyl, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, (1-4C) alkoxycarbamoyl-alkyl 1-2C, phenyl-alkyl 1-3C which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or by alkylenedioxy 1-4C, it being possible that the group phenyl is mono- to tri-substituted by substituents identical or different; phenyl that is unsubstituted or substituted by one or two independently selected substituents between 1-4C alkyl, 1-4C alkoxy, halogen, halo-alkyl 1-2C which it has 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having from 1 to 3 halogen, nitro or cyano atoms;

R 4 is 1-4C alkyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S.

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(2) Compounds of formula I of item (1) in where X is N and Y is OCH 3;

(3) Compounds of formula I of item (1) in where X is CH;

(4) Compounds of formula I of item (1) in where X is N, Y is NHCH 3 and R 1 is CH 3, cyclopropyl or CN;

(5) Compounds of formula I of item (1) in where A is oxygen, NCH 3 or n-C 6 H 5, in  particular oxygen or NCH3, very particularly oxygen;

(6) Compounds of formula I of item (1) in where R 1 is methyl, cyclopropyl or cyano, in particular methyl;

(7) Compounds of formula I of item (1) in where:

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also:

A is an O atom or the group NR4;

R1 is halo-alkyl 1-4C;

R2 is 1-4C alkyl or cyclopropyl, in particular methyl or cyclopropyl;

R 3 is hydrogen, 1-6C alkyl, halo-1-6C alkyl having 1 to 5 halogen atoms, (1-4C) alkoxy 1-2C alkyl, (2-4C) alkenyl 1-2C alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, (2-4C) alkynyl 1-2C alkyl, 3-6C cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl
1-4C which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-1-4C alkyl; (1-4C) alkoxycarbonyl 1-2C, alkoxy (1-4C) carbamoyl-1-2C alkyl, phenyl-1-3C alkyl which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo - 1-4C alkyl, cyano, nitro, or 1-4C alkylenedioxy, it being possible that the phenyl group is mono- to tri-substituted by identical or different substituents; phenyl which is unsubstituted or substituted by one or two substituents independently selected from 1-4C alkyl, 1-4C alkoxy, halogen, 1-2C halo-alkyl having 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from 1-4C alkyl, 1-4C alkoxy, halogen, 1-2C halo-alkyl having 1 to 3 halogen, nitro or cyano atoms;

R 4 is 1-4C alkyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S.

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(9) Compounds of formula I of item (1) in where R2 is a group

8

Y

Z is - (alkyl 1-4C) -O-, -S (O) 2 -, - (alkyl 1-4C) -S (O) 2 -, -S (O) 2 - (1-4C alkyl),

in particular -O-, -CH2 -O- or -O-CH2 -,

very particularly -O-CH2;

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(10) Compounds of formula (1) of item (1) in where R2 is a group

9

and B is haloalkyl 1-4C or is 2-4C alkenyl or alkynyl 2-4C-1-2C alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or is aryl or aryl that is monosubstituted or disubstituted, independently, by 1-2C alkyl, haloalkyl 1-2C, halogen, alkoxy 1-2C or haloalkoxy 1-2C, or is it a group

10

R 5, R 6, R 7, R 8, and R 9 they are independently hydrogen, 1-2C alkyl or halogen; Y

p is 0, 1, 2 or 3;

B is in particular alkyl 1-2C, haloalkyl 1-3C or is allyl or propargyl, each of which it is unsubstituted or in each case replaced by 1 or 2 halogen atoms or 1 or 2 methyl groups, or phenyl, phenyl that is replaced by a substituent chosen from the group consisting of fluorine, chlorine, bromine and CF3, or a group

eleven

(11) Compounds of formula I of item (1) in where R2 is a phenyl group that is substituted in the position 4 times -Z-B;

(14) Compounds of formula I where

X is CH; Y is OCH 3; A is oxygen;

R2 is 4-methylphenyl or 4-allyloxyphenyl or 4- (3-Trifluoromethyl-benzyloxy) phenyl or 4- (2,2-dichlorocyclopropylmethoxy) phenyl Y

R 3 is CH 3;

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(15) Compounds of formula I where

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also:

A is an O atom or the group NR4;

R1 is 1-4C alkyl; cyclopropyl; cyano or methylthio;

R2 is hydrogen; I rent 1-6C; 3-6C cycloalkyl; phenyl that is unsubstituted or monosubstituted to disubstituted, so independent, by halogen, alkyl 1-4C, alkoxy 1-4C, haloalkyl 1-2C, haloalkoxy 1-2C, 3-6C alkenyloxy, alkynyloxy 3-6C, alkylenedioxy 1-4C, cyano or nitro; or thienyl; R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, (1-4C) alkoxycarbamoyl-alkyl 1-2C, phenyl-alkyl 1-3C which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or by alkylenedioxy 1-4C, it being possible that the group phenyl is mono- to tri-substituted by substituents identical or different; phenyl that is unsubstituted or substituted by one or two independently selected substituents between 1-4C alkyl, 1-4C alkoxy, halogen, halo-alkyl 1-2C which it has 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having from 1 to 3 halogen, nitro or cyano atoms;

R 4 is 1-4C alkyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S.

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(16) Compounds of formula I of item (15) in where

X is CH or N;

Y is OCH 3;

A is O or N-R4;

R1 is methyl, cyclopropyl or methylthio;

R2 is methyl; cyclopropyl; phenyl that is unsubstituted or monosubstituted to disubstituted, so independent, by halogen, alkyl 1-4C, alkoxy 1-4C, 1-2C alkyl which is substituted by 1-5 halogen atoms, haloalkoxy 1-2C, 3-6C alkenyloxy, alkynyloxy 3-6C, alkylenedioxy 1-4C, cyano or nitro; or thienyl; and where

R_ {3} is defined as in formula I and

R 4 is methyl or phenyl, or

R 3 and R 4 together with the atom of Nitrogen to which they are attached are pyrolidine, piperidine, morphorelin, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole or 1,2,3-triazole;

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(17) Compounds of formula I of item (15) in where

X is N;

Y is NHCH 3;

A is O or N-R4;

R1 is methyl, cyclopropyl or methylthio;

R2 is methyl; cyclopropyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, 1-4C alkyl, 1-4C alkoxy, 1-2C alkyl that is substituted by 1-5 halogen atoms, haloalkoxy
1-2C, 3-6C alkenyloxy, 3-6C alkynyloxy, 1-4C alkylenedioxy, cyano or nitro; or thienyl; and where

R_ {3} is defined as in formula I and

R 4 is methyl or phenyl, or

R 3 and R 4 together with the atom of Nitrogen to which they are attached are pyrrolidine, piperidine, morphorelin, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole or 1,2,3-triazole;

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(18) Compounds of formula I of item (15) in where

A is oxygen;

R1 is methyl;

R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, alkyl 1-4C, alkoxy 1-4C, 1-2C alkyl which is substituted by 1 to 5 atoms of  halogen, haloalkoxy 1-2C, alkenyloxy 3-6C, alkynyloxy 3-6C, 1-4C alkylenedioxy, cyano or nitro; or thienyl; Y

R 3 is 1-6C alkyl;

while X and Y are defined as in the formula I of point (15);

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(19) Compounds of formula I where

R1 is methyl;

R2 is methyl; Y

R 3 is as already described; Y

R 4 is methyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached form a 5 to 7 member ring, saturated or unsaturated, which is unsubstituted or substituted by 1-4C alkyl and which may have 1 to 3 additional heteroatoms selected from N, O and S;

while A, X and Y are defined as in the formula I of item (15);

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(20) Compounds of formula (1) where

R 3 is hydrogen; I rent 1-4C; haloalkyl 1-4C having 1 to 3 halogen atoms; Alkoxy 1- 2C-alkyl 1-2C; propenyl that is unsubstituted or substituted for 1 to 3 halogen atoms; propargyl; cycloalkyl 3-6C; cycloalkyl (3-6C) methyl which is unsubstituted or substituted by 1 to 2 halogen atoms; cyano-alkyl-1-2C; (1-2C) alkoxy carbonyl alkyl 1-2C; phenyl-alkyl-1-2C which is unsubstituted or substituted by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano, nitro or 1-2C alkylenedioxy, the group being possible phenyl is monosubstituted to substituted by substituents identical or different; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen atoms, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen, cyano or nitro;

R 4 is methyl or phenyl; or

R 3 and R 4 together with the atom of nitrogen to which they are attached form a 5 to 7 member ring, saturated or unsaturated, which is unsubstituted or substituted by 1-4C alkyl and which may have 1 to 3 additional heteroatoms selected from N, O and S;

while A, X, Y, R1 and R2 are defined as in formula I of item (15);

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(21) Among the compounds of formula I mentioned in (20), those in which R 3 and R 4 together with the nitrogen atom to which they are attached are triazolyl, morpholinyl, 2,6-dimethylmorpholinyl, azepinyl, piperidyl or pyrrolidinyl;

(22) Compounds of formula I where

A is oxygen;

R1 is methyl;

R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, alkyl 1-4C, alkoxy 1-4C, 1-2C alkyl which is substituted by 1 to 5 atoms of  halogen, haloalkoxy 1-2C, alkenyloxy 3-6C, alkynyloxy 3-6C, 1-4C alkylenedioxy, cyano or nitro; or thienyl; Y

R 3 is hydrogen; I rent 1-4C; haloalkyl 1-4C having 1 to 3 halogen atoms; alkoxy 1-2C-alkyl 1-2C; propenyl that is unsubstituted or substituted by 1 to 3 atoms of halogen; propargyl; 3-6C cycloalkyl; cycloalkyl (3-6C) methyl which is unsubstituted or substituted by 1 to 2 halogen atoms; cyano-alkyl-1-2C; (1-2C) alkoxy carbonyl alkyl 1-2C; phenyl-alkyl-1-2C which is unsubstituted or substituted by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano, nitro or 1-2C alkylenedioxy, the group being possible phenyl is monosubstituted to substituted by substituents identical or different; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen atoms, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen, cyano or nitro;

while X and Y are defined as in the formula I of point (15);

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(23) Among the compounds of formula I mentioned in (22), those where

A is oxygen;

R1 is methyl;

R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, trifluoromethyl, or trifluoromethoxy; Y

R 3 is methyl;

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(24) Compounds of formula I where

A is NCH 3;

R1 is methyl;

R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, trifluoromethyl, or trifluoromethoxy;

R 3 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen atoms, cyano or nitro;

while X and Y are defined as in the formula I of point (15);

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(25) Compounds of formula I where

X is an atom of N;

Y is OR 11;

R 11 is 1-4C alkyl; Y

A, R 1 R 2 and R 3 are defined as in formula I;

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(28) Compounds of formula I where 3

X is an atom of N;

Y is N (R 12) R 13;

R 12 and R 13 are independently hydrogen or 1-4C alkyl; Y

A, R1, R2 and R3 are defined as in formula I;

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(31) Compounds of formula I where double link X = C is in the form E.

The compounds of formula I can be prepared as follows:

A) To obtain a compound of formula I in where Y is N (R_ {12}) R_ {13}, a compound of formula 1 wherein Y is OR 11 with HN (R 12) R 13. The reaction takes place conveniently in an inert organic diluent, for example in a alcohol such as ethanol, in an ether such as tetrahydrofuran or dioxane, an ester such as ethyl acetate, a sulfoxide such as dimethylsulfoxide, an amide such as dimethylformamide or a ketone such as methyl isobutyl ketone. Methylamine can be used in the form gaseous or otherwise dissolved, for example, in the form of a solution in ethanol. The process temperature is included conveniently between or and 40 ° C, preferably the room temperature.

B) To prepare a compound of formula I in where X, Y, A and R_ {1} -R_ {3} are defined as in formula I (and where R 3 is not hydrogen), is made react a compound of general formula

12

where A and R_ {1} -R_ {3} are defined as above, with a compound of formula general

13

where X and Y are defined as previously and U is a group outgoing.

This reaction is a substitution reaction. nucleophile that can be performed under the reaction conditions traditionally used in that case. The outgoing group U is preferably chlorine, bromine, iodine, mesyloxy or tosyloxy. The reaction is conveniently carried out in an organic diluent inert such as a cyclic ether, for example tetrahydrofuran or dioxane, a ketone such as acetone, an amide such as dimethylformamide, a sulfoxide such as dimethylsulfoxide, in presence of a base such as sodium hydride, sodium carbonate, potassium carbonate, sodium amide, a tertiary amine, for example trialkylamine, in particular diazabiciclononano or diazabicycloundecane, or silver oxide, at temperatures between -20 ° C and 80 ° C, preferably at a temperature of 0 ° C to 50 ° C.

Alternatively, the reaction can be carried out. with phase transfer catalysis in an organic solvent, for example methylene chloride, in the presence of a solution aqueous alkaline, for example sodium hydroxide solution, and of a phase transfer catalyst, for example bisulfate Tretrabutylammonium, at room temperature.

The resulting compounds of formula I can be isolated and purified by methods known per se . Likewise, the isomeric mixtures obtained, for example the mixtures of E / Z isomers, can be separated by methods known per se to provide the pure isomers, for example by means of chromatography or fractional crystallization.

The oximes of general formula II that are used as starting materials are known or can be prepared by known methods (J. Chem. Soc., Perkin Trans II 537 (1990); See. Deutsch. Chem. Ges. 62 , 866 (1929); Gazz. Chim. Ital. 37 II, 147 (1907); Liebigs Ann. Chem. 262 , 305 (1891)).

The invention also relates to compounds of formula II wherein A and R 1 to R 3 are defined as in the formula I, except those compounds wherein R 1 is methylthio.

Likewise, the starting materials of formula III can be prepared in a manner known per se , for example as described in European Patent Publication EP-A-203 606 (BASF) and in the literature cited therein, or as described in Angew. Chem. 71 , 349-365 (1959).

C) To prepare a compound of formula I in where A is oxygen and X, Y and R1 -R3 are defined as in formula I, a compound of General Formula

14

wherein X, Y R_ {1} and R2_ are defined as above, with a compound of formula general

V, U-R 3

where R_ {3} is defined as in formula I and U is defined as in formula III (and R 3 is not hydrogen neither phenyl nor pyridyl).

This reaction is a substitution reaction. nucleophilic as described in B).

D) To prepare a compound of formula IV in where X, Y, R_ {1} and R2 are defined as in formula I, follows a procedure in which a compound of is reacted General Formula

fifteen

wherein X, Y, R_ {1} and R2 are defined as above with hydroxylamine or a salt thereof, for example hydrochloride. The reaction is conveniently carried out. in pyridine or methanol as solvent at temperatures comprised between -20 ° C and + 80 ° C or the boiling point of methanol, preferably at a temperature of 0 to 50 ° C, requiring a base in case methanol is used, for example a carbonate alkali metal, such as potassium carbonate, a tertiary amine such as triethylamine, or diazabicyclononane, pyridine or oxide of silver.

The ketone of general formula VI is prepared from analogous to the method described in B). Formula Ketones General VI and its preparation are described, for example, in EP-370 629, EP-506 149, EP-403 618, EP-414 153, EP-463 488, EP-472 300, EP-460 575, W0-92 / 18494 and others publications.

E) To prepare a compound of formula I in where A, X, Y and R_ {1} -R_ {3} are defined as in formula I but where R 3 is not hydrogen, a procedure in which, for example, a compound of general formula

16

where A, X, Y and R_ {1} -R_ {3} are defined as above, with a methylation agent, for example methyl iodide, sulfate dimethyl or diazomethane. The reaction is conveniently carried out in presence of a base, for example potassium carbonate or hydride sodium, in a suitable solvent and at reaction temperatures suitable (see, for example, H. S. Anker und H. T. Clarke; Organic Syntheis, Coll. Vol. 3, 172).

F) To prepare a compound of formula VII in where A, X, Y and R_ {1} -R_ {3} are defined as in formula I, a procedure is conveniently followed in which a compound of formula is reacted

17

where A, Y and R_ {1} -R_ {3} are defined as above, with a format in the presence of a base, analogous to the method described in EP-A-178 826, for form compounds where X is CH; or undergoes nitrosation with nitrous acid or a nitrite in the presence of a base, so analogous to the method described in EP-A-254 426, to form compounds where X is N.

Another possibility for the synthesis of a compound of formula VII consists in reacting

A compound of formula

18

where A; Y and R 1 to R 3 defined as above, with methoxymethylenetriphenylphosphorane, analogously to the method described in EP-A-178 826 to form compounds where X is CH, or with O-methylhydroxylamine (or a salt thereof) analogously to the method described in EP-A-254 426, to form compounds where X is N.

The new compounds of formulas II, IV, VII, VIII and IX are also provided by the invention, in in particular the compounds of formulas II.1 and II.2.

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19

It has now been found that the compounds of formula I present, by needs in practice, a spectrum microbicide especially suitable for controlling microorganisms phytopathogens, especially fungi. They possess healing qualities, preventive and especially systemic very advantageous and can be Apply to protect numerous plants. With the compounds of formula I can inhibit or destroy pests that occur in plants or parts of plants (flowers, fruits, foliage, stems, tubers, roots) of different plant crops useful, while also protecting those parts of plants that subsequently grow against microorganisms phytopathogens

The compounds of formula I can also be apply as coating agents to protect seeds (fruits, tubers, grains) and plant cuts against infections fungal as well as against phytopathogenic fungi that occur in soil.

The compounds of formula I are effective, for example, against phytopathogenic fungi belonging to the following classes: Fungi imperfecti (especially Botrytis, Pyricularia, Helminthosporium, Fasarium, Septoria, Cercospora, Cercosporella and Altenaria ); Basidiomycetes (for example, Rhizoctonia, Hemileia, Puccinia ); Ascomycetes (for example, Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula ), Oomycetes (for example, Phytophthora, Peronospora, Bremia, Pythium, Phasmopara ).

The compounds of formula I according to the present invention are also valuable active ingredients against insects and pests of the genus Acarina, such as those present in useful and ornamental plants in agriculture, horticulture, particularly in rice crops, cotton, vegetables and fruits, and in afforestation, while they are well tolerated by warm-blooded animals, fish and plants. The compounds of formula I are especially suitable for controlling insects in vegetable, fruit and rice crops, in particular harmful insects for plants. Other fields of application of the active compounds according to the invention are the protection of stored products and materials and in the sector of hygiene, in particular the protection of domestic animals and productive cattle The compounds of formula I are effective against stages of individual development or against all stages of development of pest species of normal sensitivity, but also against species of resistant pests of parasites. its action is manifested, for example, in the death of pests, what which takes place immediately or only after a certain time, for example, during the formation of the skin, or in a lower setting of eggs and / or hatching rate.

The aforementioned animal pests include, for example:

from the genus of Lepidoptera, for example:

Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp. , Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., Diparopsp. Spider, Earias spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lybesia botp., Lybesia botp. ., Malacosoma spp., Mamestra brassicae, Manduca sixth, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylos. Scirpophaga spp., S esamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusiani and Yponomeuta spp .;

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from the genus of the Coleoptera; for example:

Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melp spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp . and Trogoderma spp. ;

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from the genus of Orthoptera, for example:

Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp . and Schistocerca spp .;

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from the genus of the Isoptera, for example:

Reticulitermes spp .;

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from the genus of the Psocópteros, for example:

Liposcelis spp .;

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of the genus Anoplura, for example:

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp . and Phylloxera spp .;

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from the genus of the Malofagos, for example:

Damalinea spp. and Trichodectes spp .;

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from the genus of the Thysanoptera, for example:

Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii ;

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from the genus of the Heteroptera, for example:

Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp. Eurygaster spp. Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp . and Triatoma spp .;

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from the genus of Homoptera, for example:

Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidp, Empoaspian sporum. , Laodelphax spp., Lecanium comi, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococyl sp. ., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri ;

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from the genus of Heminoptera, for example:

Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp .; from the genus of Diptera, for example:

Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoinaderpp. ., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxysp. , Tabanus spp., Tannia spp . and Tipula spp .;

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from the genus of Siphonaptera, for example:

Ceratophyllus spp . and Xenopsylla cheopis ;

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from the Tisanura genus, for example:

Lepisma saccharina , and

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from the genus of the Mites, for example:

Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpp. Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp . and Tetranychus spp .

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The target crops to protect within the framework of this invention comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, corn, sorghum and related species); beet (sugar beets and fodder); fruit of carozo, of bone and berries (apples, pears, plums, peaches, almonds, cherries, strawberries, currants, raspberries and blackberry); leguminous plants (beans, lentils, peas, soy); oil crops (rapeseed, mustard, poppy, olive, sunflower, coconut, castor, cocoa, peanut); crops of cucurbitaceae (cucumbers, zucchini, melons); fibrous cultures (cotton, linen, hemp, jute); citrus fruits (oranges, lemons, grapefruit, tangerines); varieties of vegetables (spinach, lettuce, asparagus, cabbage varieties, carrots, onions, tomatoes, potatoes, peppers); Laurel type crops (avocados, cinnamon, camphor), or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper and other spice plants, vine, hops, eggplants, banana crops and natural rubber as well like flowers and ornamental plants.

The action of the compounds I according to the invention and the compositions containing them, can be greatly expanded and adapted to the prevailing circumstances by the addition of other microbicides, insecticides and / or acaricides. Suitable additives include, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons, and preparations of Bacillus thuringiensis .

The active compounds of formula I apply generally in the form of compositions and can be applied simultaneously or successively, together with other active compounds on the crop surface or on the plants to be treated. These others active compounds can be both fertilizers and donors of micronutrients or other compositions that influence Plant growth It is also possible to use selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these  compositions, if desired together with other vehicles, surfactants and other auxiliaries that favor the application, normally used in the technique of formulations.

Suitable vehicles and auxiliaries can be both solid and liquid and correspond to substances ordinarily employed in the art of formulations, by for example, natural or regenerated mineral substances, solvents, dispersants, humectants, adhesives, thickeners, binders or fertilizers

As suitable solvents they enter consideration: aromatic hydrocarbons, preferably fractions containing 8 to 12 carbon atoms, as per example mixtures of xylenes or substituted naphthalenes, phthalates such as dibutyl- or dioctylphthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols as well as their ethers and esters, such as ethanol, ethylene glycol, ethylene glycolmonomethyl- or -ethyl ether, ketones such as cilohexanone, solvents strongly polar like N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, as well as vegetable oils epoxidized or not, such as epoxidized coconut or soybean oils; or Water.

As suitable solid vehicles, for For example, for dusting agents and dispersible powders, they generally use crushed natural rocks, such as calcite, talc, kaolin, montmorillonite or attapulgite.

Auxiliary substances especially advantageous that favor the application and that can lead to a noticeable reduction of the amount of application, are also the natural (animal or vegetable) or synthetic phospholipids of series of cephalins and lecithins, which can be obtained, by example, from soy.

As active surface compounds enter consideration, according to the type of active compound a formulate of formula I, nonphonic, cationic and / or surfactants anionics with good emulsifying, dispersing and moisturizers The term "surfactants" has to be understood also as comprising the mixtures of surfactants.

Suitable anionic surfactants can be so-called water-soluble soaps as well as Water soluble synthetic active surface compounds.

As suitable soaps, mention should be made of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted fatty acid ammonium salts higher (10-22C) such as, for example, sodium or potassium salts of oleic or stearic acid, or of mixtures of natural fatty acids, such as those obtainable, for example, from coconut oil or tallow oil. They also have to Mention is also made of fatty acid methyl restaurants.

As non-phonic surfactants enter consideration of polyglycol ether derivatives of alcohols aliphatic or cycloaliphatic, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 groups glycol ether and 8 to 20 carbon atoms in the hydrocarbon half (aliphatic) and from 6 to 18 carbon atoms in the alkyl half of the  alkylphenols

As examples of non-phonic surfactants, mention the nonylphenolpolyethoxyethanes, polyglycol ethers of castor oil, oxide adducts polypropylene-polyethylene, Tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

In addition they also come into consideration as nonionic surfactants fatty acid esters of polyoxyethylene sorbitan, such as trioleate polyoxyethylene sorbitan.

In the case of cationic surfactants, it deals primarily with quaternary ammonium salts that contain, such as N-substituent, at least one alkyl radical 8-22C and, like other substituents, present lower alkyl radicals, halogenated or free, benzyl or hydroxyalkyl lower.

Agrochemical compositions contain in overall between 0.1 and 99%, especially between 0.1 and 95% of a active compound of formula I, between 99.9 and 1%, especially between 99.9 and 5% of a solid or liquid adjuvant and between 0 and 25%, especially between 0.1 and 25% of a surfactant.

While commercial products will be preferably formulated as concentrates, the end user It will generally use diluted formulations.

The compositions may also contain other adjuvants such as stabilizers, defoamers, regulators of viscosity, binders, adherent agents as well as fertilizers or other active ingredients to obtain effects special.

The formulations, that is the compositions, preparations or mixtures containing the active ingredient of formula I and, optionally, a solid or liquid adjuvant, is prepare in the known manner, for example, by mixing and / or grinding homogeneously the active ingredient with a diluent, such as, for example, with a solvent (mixture), a solid carrier and, eventually, active surface compounds (surfactants).

A preferred method for applying a active compound of formula I or of an agrochemical composition that It contains at least one of these compounds, it is the application on the leaves (foliar application). The frequency and proportion of application depend on the risk of pathogen infestation in question. However, the compounds of formula I can also penetrate the plant from the ground through the root system (systemic action), if the place of growth of the plant with a liquid formulation or if the compounds are introduced  on the ground in solid form, for example in the form of granules (application on the ground). In flooded rice crops, it they can add such granules in measured quantities to the rice paddy flooded. However, the compounds of formula I can also be apply on seeds (coating), either by impregnation of the seeds with a liquid formulation of the active ingredient or by coating them with a solid formulation. In principle it can protect all types of plant reproduction material with the compounds of formula I, for example, seeds, roots, Stems, branches or buds. The invention also relates to seeds treated with a compound of formula I.

The compounds of formula I can be applied in unaltered form or preferably together with the adjuvants Conventionals used in formulation techniques. To do this, it formulated in a known manner, conveniently for example, as emulsifiable concentrates, brush pastes, solutions to spray directly or to dilute, diluted emulsions, powders wettable, soluble powders, dusting agents, granules (by encapsulation in polymeric substances, for example). The application methods such as spraying, spraying, sprinkling, dispersion, application by brush or irrigation, are selected, like the type of the composition, according to the desired objectives and the conditions given. The proportions of Favorable applications are normally between 1 g and 2 kg of active ingredient (ia.) per hectare, preferably between 25 g and 800 g of active ingredient per hectare, and especially preferred between 50 g and 400 g of active ingredient per hectare. In its Application as seed coating agents, apply advantageously amounts ranging from 0.001 g to 1.0 g of active ingredient per kg of seeds.

The following examples serve to illustrate with greater detail the invention without limiting it.

Preparation Examples

Example H-1

Preparation from

twenty

1.32 g of hydrochloride are added hydroxylamine to a solution of 5.2 g of 3-methoxy-2 - [([(3-oxo-2-butyl) imino] oxy) o-tolyl] acrylate of methyl (EP-A-370 629, No. 156) in 20 ml of pyridine. After stirring the mixture for 6 hours at 30 ° C, ice-water is added, filtered off the crystal cake he had formed after a few hours, and the crystals are washed with water. Recrystallization in ethanol / water provides 4.8 g of 3-methoxy-2 - [([(3-hydroxyimino-2-butyl) imino] oxy) o-tolyl] acrylate of methyl (Comp. No. 1.73) as yellow crystals of melting 104-107 ° C.

Example H-2

Preparation from

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twenty-one

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In a pressure tube, 5 ml of dimethylformamide at 0.2 g of a 65% sodium hydride suspension approximately washed with hexane. 1.6 g of 3-methoxy-2 - [([(3-hydroxyimino-2-butyl) imino] oxy) o-tolyl] acrylate of methyl and then 1.1 g of iodide 2,2,2-trifluorethyl. After the cessation of hydrogen evolution, the pressure tube closes Hermetically and the mixture is stirred for 5 hours at 50 ° C. The reaction solution is then poured into ice-water and extracted using ethyl acetate and the product is chromatographed on silica gel using acetate ethyl / hexane (1: 3). 1.2 g of 3-methoxy-2 - [([(3- (2,2,2-trifluoroethoxyimino) -2-butyl) imino] oxy] o-tolyl] acrylate of methyl (Comp. No. 1.74) as a colorless oil.

1 H NMR in CDCl 3: chemical change of two imino-substituted methyl groups: 1.99 and 2.04 ppm.

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Example H-3

Preparation from

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22

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A solution of 15 g of p-methylpropiophenone and 20 ml of isopentyl nitrite in 30 ml of methanol, slowly add dropwise to 20 ml of sodium methylate (30% in methanol). After stirring the mixture for 5 hours, 30 ml of water is added dropwise and the mixture is subsequently acidify using acetic acid. The mixture is extracted with ethyl acetate and the extract is washed with water, dried (Na 2 SO 4) and concentrated in vacuo. The residue is recrystallize from diethyl ether / n-hexane. Is obtained So α-hydroxyimino-4-methylpropiophenone as colorless crystals of a melting point of 122-124 ° C.

8.1 g of the compound are refluxed for 1 hour previously obtained and 4.6 g of hydrochloride o-methylhydroxylamine in 40 ml of pyridine. After if toluene is added, the mixture is concentrated in vacuo, treated with water and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and concentrated in vacuo. The O-methyl oxime of α-hydroxyimino-4-methylpropiophenone crystallizes from diethyl ether / n-hexane in the form of colorless crystals with a melting point of 156-157 ° C.

1.87 g of the oxime is added above obtained and 2.58 g of 2 - (α-bromo-o-tolyl) -3-methoxyacrylate of methyl to a suspension of 0.41 g of sodium hydride in 25 ml of N, N-dimethylformamide and the reaction mixture are stir for 3 hours. It is then acidified using acetic acid It is treated with water and extracted with ethyl acetate. The organic phase it is washed twice with saturated sodium bicarbonate solution and a once with saturated sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent is distilled off in empty. The compound H-3 crystallizes in ether diethyl / n-hexane in the form of colorless crystals with a melting point of 98-101 ° C (Comp. No. 1,117).

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Example H-4

Preparation from

2. 3

0.37 g of a hydride suspension is washed approximately 65% sodium with hexane and 10 ml of dimethylformamide To this suspension is added a mixture of 2.59 g of O-methyl oxime of Methyl 2- (2-bromomethylphenyl) glyoxylate and 2.42 g of 2- (diphenylhydrazono) -3-hydroxyiminobutane and the mixture is then heated to 40-50 ° C using a hot air blower until hydrogen is released from vigorous form The mixture is then stirred for 1 hour with exclusion of moisture and poured into ice-water. The extraction with ethyl acetate and chromatography on gel silica using ethyl acetate / hexane (1: 2) provides 3.7 g of O-methyl oxime of 2 - [([(3-diphenylhydrazono-2-butyl) -imino] oxy) o-tolyl] glycoxylate of methyl (Comp. No. 2.19) as a yellow oil.

1 H NMR in CDCl 3: chemical change of two imino-substituted methyl groups: 1.64 and 2.12 ppm.

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Example H-5

Preparation from

24

1.9 g of O-methyl oximex is stirred from 2 - [({(3-diphenylhydrazono-2-butyl) -imino} oxy) o-tolyl] glycoxylate of methyl for 2 hours at room temperature in 10 ml of a 33% methylamine solution in ethanol. Ethanol and excess of Methylamine are distilled off. The residue is received in ether diethyl, the solution is filtered, the filtrate is evaporated until dryness, the product remaining as a crystalline solid. He washing with hexane provides 1.8 g of O-methyl oxime from 2 - [({(3-diphenylhydrazono-2-butyl) imino} oxy) o-tolyl] glyoxylamide of N-monomethyl (Comp. No. 3.19) as crystals of pale beige with a melting point of 135-136 ° C.

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Example H-6

Preparation from

25

1.74 g of 1- (O-methyl oxime) -2-oxime from 1- [4- (2,2-Dichlorocyclopropylmethoxy) phenyl] propane-1,2-dione of formula (AA) to 0.13 g of sodium hydride in 25 ml of N, N-dimethylformamide. 1.5 g of 2- (2-bromomethylphenyl) -3-methoxyacrylate of methyl of formula (BB) and the mixture is stirred for 3 hours at room temperature. The mixture is acidified using acetic acid and water and ethyl acetate are added. The aqueous layer separates and the phase Organic is washed once with saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent evaporates in vacuum and the residue obtained is purified on silica gel using hexane / ethyl acetate (3: 1). The title compound is obtained Like an oil Separation by column chromatography on gel silica (hexane / ethyl acetate solution 3: 1) provides 3 isomers: isomer A, m.p. 86-88 ° C, isomer B, oil, isomer C, oil (Compound 5.9).

26

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27

The following compounds can be prepared in this way or analogously to one of the methods described previously.

(Abbreviations: Me = methyl, Et = ethyl, Δ = cyclopropyl, Ph = phenyl, m.p. = melting point). NMR: The Chemical changes are offered as δ (ppm) in CDCl 3.

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(Table goes to page next)

TABLE 1

28

29

30

31

** p.f. or 1 H NMR of R 1 / R 2 or R 3

The compounds 1,120 and 1,121 are not part of the invention.

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TABLE 2

32

33

3. 4

35

 ** p.f. or 1 H NMR of R 1 / R 2 or R 3

The compounds 2,120 and 2,121 are not part of the invention.

TABLE 3

36

37

38

39

 ** p.f. or 1 H NMR of R 1 / R 2 or R 3

 The compounds 3,120 and 3,121 are not part of the invention.

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TABLE 4

40

41

42

43

44

Four. Five

46

* The sign "-" in column Z means that the compound does not have a -Z-B substituent.

** Data Physical: p.f. or <1> H NMR of R1 or R3, R3 are always CH 3 according to the structural formula in the Table heading.

*** The Z radicals have to be read in such a way that the skeleton of the structure is to the left of the structural element in issue, while substituent B is on the right.

For example, him Z-B substituent in compound 4.107 is -CH 2 O-phenyl.

The compounds 4.1-4.8 and 4.10-4.12 are not part of the invention.

The compound 4.20 is not part of the invention.

The compounds 4.73-4.80 are not part of the invention.

The compounds 4.83-4.84 and 4.92 are not part of the invention.

The compounds 4,118. 4,122 and 4,123 are not part of the invention.

The compounds 4,155 and 4,157 are not part of the invention.

TABLE 5

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47

48

and the compounds

480

isomer 1: 113-115 ° C / isomer 2: oil

49

isomer 1: oil / isomer 2: oil

fifty

resin

51

155-160 ° C

52

isomer 1: 109-110 ° C / isomer 2: resin

53

isomer 1: 131-133 ° C / isomer 2: resin

** Data Physical: p.f or 1 H NMR of R 1 / R 2 or R 3

The compound 5.53 is not part of this invention.

TABLE 6

54

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TABLE 7

55

56

57

58

The compounds 7.27-7.34 and 7.40-7.41 do not form part of this invention.

The compounds 7.83-7.86 are not part of this invention.

The compounds 7.88-7.90 and 7.96-7.97 do not form part of this invention.

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2. Examples of active ingredient formulations of formula I (% = weight percentage)

2.1. Wettable powders to) b) C) Ingredient active of the Tables 1-7. 25% fifty% 75% Lignosulfonate sodium 5% 5% - Lauryl sulfate sodium 3% - 5% Diisobutylnaphthalenesulfonate sodium - 6% 10% Octylphenol-polyethylene glycol ether - 2% - (7-8 moles of oxide ethylene) Silica highly scattered 5% 10% 10% Kaolin 62% 27% -

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The active ingredient is thoroughly mixed with the additives and the mixture is completely ground in a suitable mill. Thus wettable powders are obtained that can be diluted with water to provide suspensions of any concentration desired.

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2.2 Concentrated on emulsion Ingredient active of the Tables 1-7. 10% Octylphenol-polyethylene glycol ether (4-5 moles of oxide ethylene) 3% Dodecylbenzenesulfanate calcic 3% Cyclohexanone 3. 4% Mixture of xylenes fifty%

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Emulsions of any kind can be prepared desired dilution from this concentrate by dilution of Same with water.

2.3. Powder to) b) Ingredient active of the Tables 1-7 5% 8% talcum powder 95% - Kaolin - 92%

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Powders ready for use are obtained by mixing in active ingredient with the vehicle and moving the mixture in a suitable mill.

2.4. Granules of extruder Ingredient active of the Tables 1-7 10% Lignosulfonate sodium 2% Carboxymethyl cellulose one% Kaolin 87%

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The active ingredient is mixed with the additives and the obtained mixture is ground and hydrated with water. This mixture is Extruded subsequently dried in a stream of air.

2.5 Granules coated Ingredient active of the Tables 1-7 3% Polyethylene Glycol (PM 200) 3% Kaolin 94% (P.M = molecular weight)

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In a mixer, the finely active ingredient ground is applied evenly to the kaolin that has been moistened with polyethylene glycol. Coated granules are thus obtained dust free

2.6. Concetrado in suspension Ingredient active of the Tables 1-7 40% Ethylene glycol 10% Nonylphenolpolyethylene glycol ether (15 moles of oxide ethylene) 6% Lignosulfonate sodium 10% Carboxymethyl cellulose one% Solution 37% aqueous formaldehyde 0.2% Oil silicone in the form of an aqueous emulsion at 75% 0.8% Water 32%

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The finely ground active ingredient is mixed intimately with additives. A concentrate is thus obtained in suspension from which suspensions of any desired dilution by diluting it with water.

3. Biological Examples A) Microbicidal action

Example B-1

Action against Phytophthora infestans in tomatoes a) Healing action

Plants are grown for three weeks tomato of the "Roter Gnom" variety and then pulverized with a suspension of fungus zoospores and incubation proceeds in a cabinet at a temperature of 18 to 20 ° and at atmospheric humidity saturated After 24 hours the humidification is interrupted. A once the plants have dried, they are sprayed with a mixture comprising the active ingredient, formulated as a powder wettable, at a concentration of 200 ppm. Once the spray applied coating, plants are returned to the humidity chamber for 4 days. The number and the size of typical spots on the leaves that developed after this period, to evaluate the activity of the test substances

b) Preventive-systemic action

The active ingredient, formulated as a wettable powder, is applied in a concentration of 60 ppm (with respect to the volume of soil) to the surface of the potting soil where three-week-old tomato plants of the "Roter" variety are found Gnom. " Once the plants have remained at rest for 3 days, the underside of the leaves is sprayed with a suspension of zoospores from Phytophthora infestans . The plants are then kept for 5 days in a spray cabinet at 18-20 ° C and saturated atmospheric humidity. After this period, the typical spots on the leaves develop, the number and size of which are used to evaluate the activity of the test substances.

At the same time as control plants without treat, but infected, showed a 100% infestation, the active ingredients of formula I according to any of the tables, in  particular compounds No. 1.5, 1.24, 1,117, 2.24, 2.74 and 3.24, allow to reduce the infestation in both trials to 20% or less.

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Example B-2

Action against Plasmopara viticultural (Bert. Et Curt.) (Berl. Et De Toni) in vines a) Residual-preventive action

Cuttings are grown in the greenhouse vine of the variety "Chasselas". When they have reached the 10-leaf phase, 3 plants are sprayed with a mixture (200 ppm active ingredient). Once the coating applied by spraying on the plants, the side Lower leaves are uniformly inoculated with a suspension of spores of the fungus. The plants are then kept in a chamber of humidity for 8 days. After this period, they develop clearly the symptoms of disease in control plants. Be employ the number and size of plant lesions treated to evaluate the activity of the substances in the test.

b) Healing action

Vine cuttings of the "Chasselas" variety are grown in the greenhouse and, when they have reached the 10-leaf phase, they are inoculated on the underside of the leaves with a spore suspension of Plasmopara viticola . Once the plants have remained in a humidity chamber for 24 hours, they are sprayed with a mixture of active ingredient (200 ppm of active ingredient). The plants are then kept for another 7 days in the humidity chamber. After this period, disease symptoms have developed in the control plants. The number and size of the lesions in the treated plants are used to evaluate the activity of the active substances. Compared to control plants, the infestation of plants that have been treated with the active ingredients of formula I is 20% or less.

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Example B-3

Action against Pythium debaryanum in beet ( Beta vulgaris ) a) Action after application on land

The fungus is grown on oat grains sterile and added to a mixture of soil and sand. Earth like that inoculated is introduced into flower pots and seeds are sown Beet Immediately after planting, the preparations of the test, formulated as wettable powders, are poured onto the soil in the form of an aqueous suspension (20 ppm ingredient active with respect to the volume of land). Following, the pots are placed in the greenhouse for 2-3 weeks at 20-24 ° C. At all times, the earth is keep uniformly wet by gently spraying it with water. When the test is evaluated, the plant sprout is determined of beet and the proportion of healthy and diseased plants.

b) Action after seed coating

The fungus is grown on oat grains sterile and added to a mixture of soil and sand. Earth like that inoculated is introduced into flower pots and seeds are sown of beet that had been coated with the preparations of test, formulated as powder for seed coating (1,000 ppm of active ingredient with respect to the weight of the seeds). The sherds along with the seeds are placed in the greenhouse at 20-24 ° C for 2-3 weeks The earth is kept uniformly moist by spraying it gently with water. When evaluating the trial, it is determined the sprout of beet plants and the proportion of plants Healthy and sick

After treatment with the ingredients assets of formula I, in particular with compounds No. 1.5, 1.24, 1,117, 2.24, 2.74 and 3.24, more than 80% of the plants sprouted And they looked healthy. In the control pots, only a few sickly-looking plants sprouted.

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Example B-4

Residual-protective action against Cercospora arachidicola in peanuts

Peanut plants are sprayed from 10-15 cm high to the point of dripping with a Acus spray mixture (0.02% active ingredient) and after 48 hours are inoculated with a conidia suspension of the fungus. The plants are incubated for 72 hours at 21 ° and atmospheric humidity elevated and then placed in the greenhouse until it is They develop the typical spots on the leaves. The action of active ingredient is evaluated 12 days after inoculation in based on the number and size of leaf spots.

The active ingredients of formula I cause a reduction in leaf spots at a value less than 10% about the surface area of the leaves. In some cases, the disease is completely reduced (0-5% of infestation).

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Example B-5

Action against Puccinia graminis in wheat a) Residual-protective action

Wheat plants are sprayed, 6 days later from sowing, to the point of dripping with a spray mixture aqueous (0.02% active ingredient) and after 24 hours inoculate with a suspension ureidopores of the fungus. After a incubation time 48 hours (conditions: relative humidity: 95 at 100% at 20 ° C), the plants are placed in the greenhouse at 22 ° C. 12 days after inoculation, the development is evaluated of pustules of blast.

b) Systemic action

After 5 days of planting, it is poured, near wheat plants, an aqueous spray mixture (0.006% active ingredient with respect to the volume of soil). Be carefully avoid any contact of the sprayable mixture with the aerial parts of the plants. After 48 hours, the plants are inoculated with a suspension of uridoid spores of the fungus. After an incubation time of 48 hours (conditions: humidity relative from 95 to 100% at 20 °), the plants are placed in the greenhouse at 22 °. After 12 days from inoculation, it evaluates the development of blight pustules.

The compounds of formula I, in particular those of Table 1, especially compounds No. 1.5, 1.24, 1,117, 2.74, cause a marked reduction in infestation by the fungus, in some cases up to 10-0%.

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Example B-6

Action against Pyricularia oryzae in rice a) Residual-protective action

Rice plants are grown for 2 weeks and then sprayed to the point of dripping with a sprayable aqueous spray mixture (0.02% ingredient active) and after 48 hours they are inoculated with a suspension of Conidia of the fungus. The fungus infestation is evaluated 5 days after inoculation, during which period the humidity atmospheric relative remained at 95-100% and the temperature at 22 °.

b) Systemic action

An aqueous spray mixture (0.006% of active ingredient with respect to the volume of land) is poured near 2 week old rice plants. It is carefully avoided  any contact of the sprayable mixture with the aerial parts of the plants. The pots are then filled with a quantity of water such that the lower parts of the plant stems of Rice are submerged. After 96 hours, the plants are inoculate with a conidia suspension of the fungus and remain for 5 days at a relative atmospheric humidity remained at 95 at 100% and at a temperature of 24 ° C. In many cases, the compounds of formula I prevent the development of disease in plants infected.

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Example B-7

Residual-protective action against Venturia inaequalis in apple trees

Apple cuttings that have new shoots of 10 to 20 cm in length are sprayed to the drip point with a spray mixture (0.02% active ingredient) and After 24 hours they are inoculated with a suspension of conidia of the fungus The plants are incubated for 5 days at a humidity atmospheric relative from 90 to 100% and kept in the greenhouse for another 10 days at 20-24 °. The infestation by Roña is evaluated 15 days after inoculation. Most the compounds of formula I of one of Tables 1, 2 or 3 have a sustainable action against diseases of roña.

Example B-8

Action against Erysiphe graminis in barley a) Residual-protective action

8 cm barley plants are sprayed height approximately to the point of dripping with a mixture water spray (0.02% active ingredient) and after 3-4 hours are sprinkled with conidia of the fungus. The inoculated plants are placed in the greenhouse at 22 °. The fungus infestation is evaluated 10 days after the inoculation.

b) Systemic action

An aqueous spray mixture (0.002% of active ingredient with respect to the volume of land) is poured near barley plants approximately 8 cm high. Be carefully avoid contact of the spray mixture with the aerial parts of the plants. After 48 hours, the plants are sprinkle with conidia of the fungus. The inoculated plants are placed in the greenhouse at 22 °. The fungus infestation is Evaluate 10 days after inoculation. The compounds of formula I, in particular compounds No. 1,117, 2,14 and 3,24, are in generally able to reduce the disease to less than 20%, and in Some cases also completely.

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Example B-9

Action against Podosphaera leucotricha on apple tree buds Residual-protective action

Apple cuttings are sprayed that have new yolks approximately 15 cm long with a mixture sprayable (0.06% active ingredient). After 24 hours, the  treated plants are inoculated with a suspension of conidia of the fungus and placed in a controlled environment cabin at a relative atmospheric humidity of 70% and at 20 ° C. The infestation by The fungus is evaluated 12 days after inoculation. The active ingredients of formula I allow to reduce the disease to less than 20% Control plants show a level of 100% disease.

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Example B-10

Action against Botrytis cinerea in apples Residual-protective action

To artificially damaged apples is applied drop by drop a spray mixture (0.02% active ingredient) In wounds The treated fruits are subsequently inoculated with a spore suspension of the fungus and incubate during a week at high atmospheric humidity and at approximately 20 ° C. The fungal action of the test substance is deduced from number of wounds showing signs of rot. The active ingredients of formula I are able to reduce the extent of rot, in some cases so complete.

Example B11

Action against Helminthosporium gramineum

Wheat grains are contaminated with a suspension of spores of the fungus and then allowed to dry. The grains contaminated are coated with a suspension of the substance of test (600 ppm active ingredient with respect to the weight of the seeds). After 2 days, the beans are arranged in dishes suitable containing agar and, after another 4 days, is evaluated the development of fungal colonies around grains. The test substance is evaluated based on the number and size of fungal colonies In some cases, the compounds of formula I show a good action, that is, colony inhibition fungal

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Example B-12

Action against Colletotrichum lagenarium in cucumbers

Cucumber plants are grown for 2 weeks and then sprayed with a spray mixture (concentration 0.002%). After 2 days, the plants are inoculated with a spore suspension (1.5 x 10 5 spores / ml) of the fungus and incubate for 36 hours at 23 ° and at high atmospheric humidity The incubation is then continued at normal atmospheric humidity at 22-23 ° C approximately. The fungus infestation that has developed It is evaluated 8 days after inoculation. Control plants untreated, but infected, show a fungal infestation of the 100% In some cases, the compounds of formula I, in particular Compounds No. 1.5 and 3.24, show an inhibition virtually complete disease infestation.

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Example B-13

Action against Fusarium nivale in rye

Rye of the Tetrahell variety, naturally infected with Fusararium nivale , is coated with the test fungicide using a mixing cylinder, using the following concentrations: 20 or 6 ppm ai (with respect to the weight of the seed).

Using a seed drill, rye infected and treated is sown in October in the field in plots 3 meters of 6 seed rows. 3 replicas are made per concentration.

Until the infestation is evaluated, the plants assay are grown under normal field conditions (preferably in a snow-covered region completely during the winter months).

To assess phytotoxicity, the seed bud in autumn and the number of plants per unit of area / number of shoots per plant in spring.

To determine the activity of the active ingredient, the percentage of Fusarium- infested plants is counted immediately after the snow melts. In the present case, the number of infested plants was less than 5%. The sprouted plants had a healthy appearance.

Example B-14

Action against Septoria nodorum in wheat

Wheat plants are sprayed in the phase of three sheets with a spray mixture (60 ppm a.i.) prepared with a wettable powder of the active ingredients (2.8: 1).

After 24 hours, the treated plants are inoculate with a conidia suspension of the fungus. The plants are then incubate for 2 days at a relative atmospheric humidity 90-100% and placed in the greenhouse at 20-24 ° C for 10 more days. After 13 days from inoculation, the fungus infestation is evaluated. Less 1% of wheat plants were infested.

Example B15

Action against Rhizoctonia solani in rice Protective-local application on land

The soil around 10-day-old rice plants was irrigated with a suspension (spray mixture) prepared with a formulated test substance without the aerial parts of the plants coming into contact with the suspension. After 3 days, the plants were inoculated by placing a stem of barley straw infected with Rhizoctonia solani between the rice plants of each pot. After incubating for 6 days in a controlled environment cabin at 29 ° C during the day and 26 ° C at night and at a relative atmospheric humidity of 95%, the fungus infestation is evaluated. Less than 5% of rice plants were infested. The plants had a healthy appearance.

Foliar protective-local application

12-day rice plants are sprayed age with a suspension prepared with the test substances formulated One day later, the inoculation is performed by placing a barley straw stem infected with Rhizoctonia solani among Rice plants from each pot. Plants are evaluated after incubation for 6 days in an environment cabin controlled at 29 ° C during the day and 26 ° C at night and at relative atmospheric humidity of 95%. Control plants without treat, but inoculated, showed a fungal infestation of the 100% The compounds of formula I cause in certain cases a complete inhibition of infestation with the disease.

B. Insecticidal action

Example B-16

Action against Aphis craccivora

Pea seedlings are infected with Aphis craccivora , subsequently sprayed with a spray mixture comprising 400 ppm of active ingredient and then incubated at 20 °. The percentage of population reduction (% action) is determined after 3 and 6 days by comparing the number of dead aphids in the treated and untreated plants. In this test, the compounds of Tables 1-7 have a good action. Compound No. 4.5, isomer 1, in particular, has an action greater than 80%.

Example B-17

Action against Diabrotica balteata

Corn seedlings are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after drying the spray applied coating, they are infected with 10 larvae of the second stage of Diabrotica balteata and subsequently placed in a plastic container . The population reduction in percentage (% action) is determined 6 days later by comparing the number of dead larvae in the treated and untreated plants.

In this test, the compounds of the Tables 1-7 have a good deed. In particular the Compounds 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, isomer 1 and 5.51 Isomer 1, have an action greater than 80%.

Example B-18

Action against Heliothis virescens

Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after drying the spray applied coating, they are infected with 10 caterpillars of the first stage of Heliothis virescens , and then placed in a container of plastic. The percentage of population reduction and feeding damage (% action) are determined 6 days later by comparing the number of dead caterpillars and feeding damage in treated and untreated plants.

In this test, the compounds of the Tables 1-7 show a good deed. In particular the Compounds 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 an action greater than 80%.

Example B-19

Action against Spodoptera littoralis

Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after drying the spray applied coating, they are infected with 10 caterpillars of the third stage of Spodoptera littoralis , and then placed in a container of plastic. The percentage reduction of the population and the percentage reduction of food damage (% action) are determined after 3 days by comparing the number of dead caterpillars and the food damage of the treated and untreated plants.

In this test, the compounds of the Tables 1-7 show a good deed. In particular the Compounds 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 an action greater than 80%

C. acaricidal activity

Example B-20

Action against Tetranychus urticae

Young bean plants are infected with a mixed population of Tetranychus urticae and, after 1 day, they are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient, incubated for 6 days at 25 ° and then the evaluation is performed . The percentage of population reduction (% action) is determined by comparing the number of eggs, larvae and dead adults in the treated and untreated plants.

In this test, the compounds of the Tables 1-6 show a good action. In particular, the Compounds No. 1.5, 1.24, 2.24 and 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 action greater than 80%.

Example B-21

Action against Boophilus microplus

Adult female ticks full of blood will They are arranged on a PVC plate and covered with a wool ball of cotton and 10 ml of aqueous solution are poured over the ticks Test comprising 125 ppm of active ingredient. The Cotton wool ball and ticks are incubated for 4 weeks until oviposition. The action manifests itself in the case of females, in the form of mortality or sterility or, in the case of eggs, in the form of an ovicidal action.

Claims (45)

1. A compound of formula I 59 and its possible isomers and mixtures of isomers, in where:

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also A is an O atom or the group NR4; R1 is 1-4C alkyl; cyclopropyl; cyano or methylite; R2 is hydrogen; I rent 1-6C; 3-6C cycloalkyl; phenyl that is unsubstituted or monosubstituted to disubstituted, so independent, by halogen, alkyl 1-4C, alkoxy 1-4C, haloalkyl 1-2C, haloalkoxy 1-2C, 3-6C alkenyloxy, alkynyloxy 3-6C, alkylenedioxy 1-4C, cyano or nitro; or thienyl; R 3 is hydrogen, 1-6C alkyl, halo-1-6C alkyl having 1 to 5 halogen atoms, (1-4C) alkoxy 1-2C alkyl, (2-4C) alkenyl 1-2C alkyl which it is unsubstituted or substituted by 1 to 3 halogen atoms; alkynyl (2-4C) alkyl
1-2C; 3-6C cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms; cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen atoms; cyano-alkyl 1-4C; (1-4C) alkoxycarbonyl
1-2C, phenyl-1-3C alkyl which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-1-4C alkyl, cyano, nitro, or 1-4C alkylenedioxy, the group being possible phenyl is mono- to tri-substituted by identical or different substituents; phenyl which is unsubstituted or substituted by one or two substituents independently selected from 1-4C alkyl, 1-4C alkoxy, halogen, 1-2C halo-alkyl having 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from 1-4C alkyl, 1-4C alkoxy, halogen, 1-2C halo-alkyl having 1 to 3 halogen, nitro or cyano atoms; R 4 is 1-4C alkyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S. 2. A compound of formula I according to the claim 1, wherein X is CH or N; Y is OCH 3; A is O or N-R4; R1 is methyl, cyclopropyl or methylthio; R2 is methyl; cyclopropyl; phenyl which is unsubstituted or monosubstituted to disubstituted, independently, by halogen, 1-4C alkyl, 1-4C alkoxy, 1-2C alkyl which is substituted by 1 5 halogen atoms, haloalkoxy
1-2C, 3-6C alkenyloxy, 3-6C alkynyloxy, 1-4C alkylenedioxy, cyano or nitro; or thienyl; and where R_ {3} is defined as in formula I and R 4 is methyl or phenyl, or R 3 and R 4 together with the atom of Nitrogen to which they are attached are pyrrolidine, piperidine, morphorelin, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole or 1,2,3-triazole. 3. A compound of formula I according to the claim 1, wherein X is N; Y is NHCH 3; A is O or N-R4; R1 is methyl, cyclopropyl or methylthio; R2 is methyl; cyclopropyl; phenyl which is unsubstituted or monosubstituted to disubstituted, independently, by halogen, l-4C alkyl, 1-4C alkoxy, 1-2C alkyl which is substituted by 1 5 halogen atoms, haloalkoxy
1-2C, 3-6C alkenyloxy, 3-6C alkynyloxy, 1-4C alkylenedioxy, cyano or nitro; or thienyl; and where R_ {3} is defined as in formula I and R 4 is methyl or phenyl, or R 3 and R 4 together with the atom of Nitrogen to which they are attached are pyrrolidine, piperidine, morphorelin, thiomorpholine, hexamethyleneimine, imidazole, pyrazole, pyrrole, 1,2,4-triazole or 1,2,3-triazole. 4. A compound of formula I according to the claim 1, wherein A is oxygen; R1 is methyl; R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, alkyl 1-4C, alkoxy 1-4C, 1-2C alkyl which is substituted by 1 to 5 atoms of  halogen, haloalkoxy 1-2C, alkenyloxy 3-6C, alkynyloxy 3-6C, 1-4C alkylenedioxy, cyano or nitro; or thienyl; Y R 3 is 1-6C alkyl. 5. A compound of formula I according to the claim 1, wherein R1 is methyl; R2 is methyl; Y R_ {3} is as already described in the claim 1; Y R 4 is methyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached form a 5 to 7 member ring, saturated or unsaturated, which is unsubstituted or substituted by 1-4C alkyl and which may have 1 to 3 additional heteroatoms selected from N, O and S. 6. A compound of formula I according to the claim 1, wherein R 3 is hydrogen; I rent 1-4C; haloalkyl 1-4C having 1 to 3 halogen atoms; alkoxy 1-2C-alkyl 1-2C; propenyl that is unsubstituted or substituted by 1 to 3 atoms of halogen; propargyl; 3-6C cycloalkyl; cycloalkyl (3-6C) methyl which is unsubstituted or substituted by 1 to 2 halogen atoms; cyano-alkyl-1-2C; (1-2C) alkoxy carbonyl alkyl 1-2C; phenyl-alkyl-1-2C which is unsubstituted or substituted by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano, nitro or 1-2C alkylenedioxy, the group being possible phenyl is monosubstituted to substituted by substituents identical or different; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen atoms, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen, cyano or nitro; R 4 is methyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached form a 5 to 7 member ring, saturated or unsaturated, which is unsubstituted or substituted by 1-4C alkyl and which may have 1 to 3 additional heteroatoms selected from N, O and S. 7. A compound of formula I according to the claim 6, wherein R 3 and R 4 together with the atom of Nitrogen to which they are attached are triazolyl, morpholinyl, 2,6-dimethylmorpholinyl, azepinyl, piperidyl or pyrrolidinyl 8. A compound of formula I according to the claim 1, wherein A is oxygen; R1 is methyl; R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, alkyl 1-4C, alkoxy 1-4C, 1-2C alkyl which is substituted by 1 to 5 atoms of  halogen, haloalkoxy 1-2C, alkenyloxy 3-6C, alkynyloxy 3-6C, 1-4C alkylenedioxy, cyano or nitro; or thienyl; Y R 3 is hydrogen; I rent 1-4C; haloalkyl 1-4C having 1 to 3 halogen atoms; alkoxy 1-2C-alkyl 1-2C; propenyl that is unsubstituted or substituted by 1 to 3 atoms of halogen; propargyl; 3-6C cycloalkyl; cycloalkyl (3-6C) methyl which is unsubstituted or substituted by 1 to 2 halogen atoms; cyano-alkyl-1-2C; (1-2C) alkoxy carbonyl alkyl 1-2C; phenyl-alkyl-1-2C which is unsubstituted or substituted by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano, nitro or 1-2C alkylenedioxy, the group being possible phenyl is monosubstituted to substituted by substituents identical or different; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen atoms, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 halogen, cyano or nitro 9. A compound of formula I according to the claim 8, wherein A is oxygen; R1 is methyl; R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, trifluoromethyl, or trifluoromethoxy; Y R 3 is methyl. 10. A compound of formula I according to the claim 1, wherein A is NCH 3; R1 is methyl; R2 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, trifluoromethyl, or trifluoromethoxy; R 3 is methyl; phenyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano or nitro; or pyridyl that is unsubstituted or monosubstituted to disubstituted, independently, by halogen, methyl, methoxy, halomethyl having 1 to 3 atoms of halogen, cyano or nitro. 11. A composition to control pests, which comprises, as active ingredient, a compound according to any of claims 1 to 10 together with a suitable vehicle. 12. Method to control and prevent pests, which comprises applying a compound according to any of the claims 1 to 10 to pests or their environment. 13. A compound of formula II 60 where A, and R_ {1} -R_ {3} are defined as in formula I of claim 1, except for the compounds wherein R 1 is methylthio 14. Compounds of formulas II.1 and II.2 according to the claim 13 61 15. A compound of formula IV 62 wherein X, Y, R_ {1} and R2 are defined as in formula I of the claim one. 16. A compound of formula VII 63

to)

X is an atom of N e

Y is OR_ {11} or N (R 12) R 13 or

b)

X is CH e

And it is OR_ {11}

and where also: R 11 is 1-4C alkyl; R 12 and R 13 are independently hydrogen or 1-4C alkyl; A is an O atom or the group NR4; R1 is alkyl 1-4C, halo-alkyl 1-4C, cyclopropyl, cyano or methylthio; R2 is hydrogen, alkyl 1-6C, cycloalkyl 3-6C, a group 64 a group; 65 or thienyl; the radicals D are identical or different and are halogen, alkyl 1-4C, alkoxy 1-4C,  halo-alkyl 1-2C, halo-alkoxy 1-2C, alkenyloxy 3-6C, alkynyloxy 3-6C, 1-4C alkylenedioxy, cyano or nitro; n is 0, 1, 2, 3 or 4; Z is -O-, -O- (alkyl 1-4C) -, - (1-4C alkyl) -O, -S (O) m, - (1-4C alkyl) -S (O) m - or -S (O) m (alkyl 1-4C) -, m is 0, 1 or 2; B is alkyl 1-6C, halo-alkyl 1-6C, cycloalkyl 3-6C or 2-6C alkenyl or alkynyl (2-4C) alkyl 1-2C, each of which is unsubstituted or substituted by 1 to 3 halogen atoms; or is it aryl, or heterocyclyl, where each of the two independently is unsubstituted or substituted by one to five substituents selected from 1-6C alkyl, halo-alkyl 1-6C, halogen, alkoxy 1-6C or halo-alkoxy 1-6C, or is it a group 66 or trimethylsilyl; R 5, R 6, R 7, R 8, and R 9 independently of each other, they are each hydrogen, alkyl 1-4C or halogen; Y p is 0, 1, 2 or 3; R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, (1-4C) alkoxycarbamoyl-alkyl 1-2C, phenyl-alkyl 1-3C which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or by alkylenedioxy 1-4C, it being possible that the group phenyl is mono- to ti-substituted by substituents identical or different; phenyl that is unsubstituted or substituted by one or two independently selected substituents between 1-4C alkyl, 1-4C alkoxy, halogen, halo-alkyl 1-2C which it has 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 halogen, nitro or cyano atoms; R 4 is 1-4C alkyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S.

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17. A compound of formula VIII 67 where A, Y and R 1 -R 3 is defined as in formula VII of the reinvidication 16. 18. A compound of formula IX 68 where A, Y and R 1 -R 3 is defined as in formula VII of the reinvidication 16. 19. A compound of formula I 69 and its possible isomers and mixtures of isomers, in where:

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also A is an O atom or the group NR4; R1 is haloalkyl 1-4C; R2 is 1-4C alkyl or cyclopropyl; R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, phenyl-1-3C alkyl which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or alkylenedioxy 1-4C, it being possible that the phenyl group is mono- to tri-substituted by identical substituents or different; phenyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents selected in a manner independent between 1-4C alkyl, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 atoms of halogen, nitro or cyano; R 4 is 1-4C alkyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S. 20. A compound of formula I 70 and its possible isomers and mixtures of isomers, in where X is CH; Y is OCH 3; R 1 is CH 3; A is oxygen; R2 is 4-methylphenyl or 4-allyloxyphenyl or 4- (3-Trifluoromethyl-benzyloxy) phenyl or 4- (2,2-dichlorocyclopropylmethoxy) phenyl Y R 3 is CH 3. 21. A compound of formula I 71 and its possible isomers and mixtures of isomers, in where

to)

X is an atom of N e

Y is OR_ {11} or N (R 12) R 13 or

b)

X is CH e

And it is OR_ {11}

and where also: R 11 is 1-4C alkyl; R 12 and R 13 are independently hydrogen or 1-4C alkyl; A is an O atom or the group NR4; R1 is alkyl 1-4C, halo-alkyl 1-4C, cyclopropyl, cyano or methylthio; R2 is a group 72 or a group; 73 D radicals are identical or different and are 1-4C alkoxy, 1-2C haloalkoxy, 3-6C alkyloxy, alkylenedioxy
1-4C; n is 0, 1, 2, 3 or 4; Z is - (alkyl 1-4C) -O, -S (O) m, - (1-4C alkyl) -S (O) m or -S (O) m (1-4C alkyl) -, m is 0, 1 or 2; B is halo-alkyl 1-6C, cycloalkyl 3-6C or alkenyl 2-6C or alkynyl (2-4C) alkyl 1-2C, each of which is unsubstituted or substituted by 1 to 3 halogen atoms; or is aryl, or heterocyclyl, where each of the two independently is unsubstituted or substituted by one to five substituents selected from alkyl 1-6C, halo-alkyl 1-6C, halogen, alkoxy 1-6C or halo-alkoxy 1-6C, or is a group 74 or trimethylsilyl; R 5, R 6, R 7, R 8, and R 9 independently of each other, they are each hydrogen, alkyl 1-4C or halogen; Y p is 0, 1, 2 or 3; R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl 1-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, (1-4C) alkoxycarbamoyl-alkyl 1-2C, phenyl-alkyl 1-3C which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or by alkylenedioxy 1-4C, it being possible that the group phenyl is mono- to tri-substituted by substituents identical or different; phenyl that is unsubstituted or substituted by one or two independently selected substituents between 1-4C alkyl, 1-4C alkoxy, halogen, halo-alkyl 1-2C which it has 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having from 1 to 3 halogen, nitro or cyano atoms; R 4 is 1-4C alkyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S. 22. A compound of formula I according to claim 21, wherein X is an atom of N; Y is OR 11; R 11 is 1-4C alkyl; and in where A 1 R 1, R 2 and R 3 are defined as in claim 21. 23. A compound of formula I according to claim 21, wherein X is an atom of N; Y is N (R 12) R 13; R 12 and R 13 are, independently, a hydrogen atom or 1-4C alkyl; Y A 1 R 1, R 2 and R 3 are defined as in claim 21. 24. A compound of formula I according to claim 21, wherein the double bond X = C is at the form E. 25. A compound of formula I according to claim 21, wherein:

to)

X is an atom of N e

Y is OCH_ {3} or NHCH 3 or

b)

X is CH e

And it is OCH_ {3},

and where also: A is an O atom or the group NR4; R1 is alkyl 1-4C, halo-alkyl 1-4C, cyclopropyl, cyano or methylthio; R2 is a group 75 or a group; 76 D radicals are identical or different and are 1-4C alkoxy, 1-2C haloalkoxy, 3-6C alkyloxy, alkylenedioxy
1-4C; n e s 0, 1, 2, 3 or 4; Z is - (alkyl 1-4C) -O, -S (O) m, - (1-4C alkyl) -S (=) m or -S (O) m (1-4C alkyl) -, m is 0, 1 or 2; B is halo-alkyl 1-6C, cycloalkyl 3-6C or alkenyl 2-6C or alkynyl (2-4C) alkyl 1-2C, each of which is unsubstituted or substituted by 1 to 3 halogen atoms; or is aryl, or heterocyclyl, where each of the two independently is unsubstituted or substituted by one to five substituents selected from alkyl 1-6C, halo-alkyl 1-6C, halogen, alkoxy 1-6C or halo-alkoxy 1-6C, or is a group 77 R 5, R 6, R 7, R 8, and R 9 independently of each other, they are each hydrogen, alkyl 1-4C or halogen; Y p is 0, 1, 2 or 3; R 3 is hydrogen, alkyl 1-6C, halo-alkyl 1-6C having 1 to 5 halogen atoms, (1-4C) alkoxy alkyl 1-2C, alkenyl (2-4C) alkyl 1-2C which is unsubstituted or substituted by 1 to 3 halogen atoms, alkynyl (2-4C) alkyl l-2C, cycloalkyl 3-6C which is unsubstituted or substituted by 1 to 4 halogen atoms, cycloalkyl (3-6C) alkyl 1-4C which is unsubstituted or substituted by 1 to 4 halogen, cyano-alkyl atoms 1-4C; alkoxy (1-4C) carbonyl-alkyl 1-2C, phenyl-1-3C alkyl which is unsubstituted or substituted halogen, 1-3C alkyl, 1-4C alkoxy, halo-alkyl 1-4C, cyano, nitro, or alkylenedioxy 1-4C, it being possible that the phenyl group is mono- to tri-substituted by identical substituents or different; phenyl that is unsubstituted or substituted by one or two substituents independently selected from alkyl 1-4C, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 halogen, nitro or cyano atoms; or pyridyl that is unsubstituted or substituted by one or two substituents selected in a manner independent between 1-4C alkyl, alkoxy 1-4C, halogen, halo-alkyl 1-2C having 1 to 3 atoms of halogen, nitro or cyano; R 4 is 1-4C alkyl or phenyl; or R 3 and R 4 together with the atom of nitrogen to which they are attached, form a 5 to 7 member ring saturated or unsaturated, unsubstituted or substituted by alkyl 1-4C, and which may contain 1 to 3 heteroatoms additional selected between N, O and S. 26. A compound of formula I, according to the claim 25, wherein X is N e And it is OCH_ {3}. 27. A compound of formula I according to the claim 25, wherein X is CH. 28. A compound of formula I according to claim 25, wherein X is N, Y is NHCH 3 and R1 is CH3, cyclopropyl or CN. 29. A compound of formula I according to claim 25, wherein A is oxygen, NCH3 or n-C 6 H 5. 30. A compound of formula I according to the claim 25, wherein R1 is methyl, cyclopropyl or cyano. 31. A compound of formula I according to the claim 25, wherein R2 is a group

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78 Y Z is - (alkyl 1-4C) -O-, -S (O) 2 -, - (alkyl 1-4C) -S (O) 2 -, -S (O) 2 - (1-4C alkyl). 32. A compound of formula I according to claim 25, wherein R2 is a group

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79 Y B is haloalkyl 1-4C or is 2-4C alkenyl or alkynyl 2-4C-1-2C alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or is aryl or aryl that is monosubstituted or disubstituted, independently, by 1-2C alkyl, haloalkyl 1-2C, halogen, alkoxy 1-2C or haloalkoxy 1-2C, or is it a group

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80

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R 5, R 6, R 7, R 8 and R 9 they are independently hydrogen, 1-2C alkyl or halogen, and p is 0, 1, 2 or 3. 33. A compound of formula I according to claim 25, wherein R2 is a phenyl group that is substituted in position 4 by -Z-B. 34. Procedure for the preparation of a compound of formula I according to claim 21, which understands: A) prepare a compound of formula I wherein Y is N (R_ {12}) R_ {13}, reacting a compound of formula I wherein Y is OR 11 with HN (R 12) R 13 in a solvent at 0-40 °; B) prepare a compound of formula I wherein X, Y, A and R_ {1} -R_ {3} are defined as in the claim 21 (and wherein R 3 is not hydrogen), making react an oxime of general formula II

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81

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where A and R_ {1} -R_ {3} are defined as above, with a benzyl derivative of the formula general

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82

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where X and Y are defined as above and U is a leaving group, in an organic diluent inert, in the presence of a base and in the presence or absence of a phase transfer catalyst at a temperature of 0 to 50 °; C) prepare a compound of formula I wherein A it is oxygen and X, Y and R1 -R3 are defined as in claim 21, reacting an oxime of formula general IV

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83

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wherein X, Y, R_ {1} and R2 are defined as above, with a compound of general formula V VU-R_ {3} where R_ {3} is defined as in formula I and U is defined as in formula III (and where R 3 is not hydrogen or phenyl or pyridyl); D) prepare a compound of formula IV wherein X, Y, R1 and R2 are defined as in claim 21, by reacting a ketone of general formula VI

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84

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wherein X, Y, R_ {1} and R2 are defined as above, with hydroxylamine or a salt thereof, in a solvent and at a temperature of 0 to 50 ° C; E) prepare a compound of formula I wherein A, X, Y and R_ {1} -R_ {3} are defined as in the claim 21 (and wherein R 3 is not hydrogen), making reacting an enol or oxime of general formula VII

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85

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where A, X, Y and R_ {1} -R_ {3} are defined as above, with a methylating agent, such as methyl iodide, sulfate dimethyl or diazomethane, in the presence of a base and in a solvent suitable. 35. A composition to control pests, which comprises, as active ingredient, a compound according to any of claims 21-23 together with a vehicle suitable. 36. Use of a compound of formula I according to the claim 21 in pest control. 37. Method to control and prevent pests, which comprises applying a compound according to any of the claims 21-33 to pests or their environment. 38. Method according to claim 37, wherein The seeds are treated. 39. Seed that has been treated according to claim 38. 40. A compound of formula II

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86

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where A, and R_ {1} -R_ {3} is defined as in formula I of claim 21, except for the compounds in which R1 is methylthio. 41. A compound of formula IV

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87

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wherein X, Y, R_ {1} and R2 are defined as in formula I of claim 21, except those compounds where R1 is methylthio 42. A compound of formula

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88

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where X, Y, R1, Z *, n, B and D have the following meanings:

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(Table goes to page next) 90 91 92 93

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The character "-" in column Z means the compound that does not have a -Z-B substituent.

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43. A compound of formula

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95

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where X, Y, A, R1, R3, R6, R7 and p They have the following meanings:

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96 97 and the compounds

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98 99

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100

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101

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102

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103 44. A compound of formula 104 in where X, Y, R_ {1}, Z *, n, B or D have the following meanings: 105 45. A compound of formula 106 in where Y, A, R 1, R 2, R 3 and NR 3 R 4 have the following meanings: 107 108 109