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1. (WO1993016986) ETHERS D'OXIMES AZOIQUES ET LEUR UTILISATION COMME FONGICIDES
Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

WHAT IS CLAIMED IS:

1. A compound of the formula I in the form of the racemic mixtures and/or isomers thereof


in which
X is CH or N,
Rj is hydrogen, Ci-C^alkyl, trifluoromethyl or cyclopropyl,
R2 is aryl or heteroaryl, each of which is unsubstituted or substituted by one or more substituents R,
R is halogen; C1-C6alkyl; C3-C6cycloalkyl; C - haloalkyl; -Qalkoxy; hydroxyl;
phenyl, benzyloxy or aryloxy, each of which is unsubstituted or substituted by halogen,

CrC alkyl, Cj-Cβalkoxy, trifluoromethyl or trifluoromethoxy; C1-C haloalkoxy; cyano; nitro; mercapto; CrC4alkylthio; NR3R4; COM^R^ cyanomethyl; SO2NR3R4; COR5 or

COOR5,
R3 and R4 independently of one another are C1-C4alkyl or
R3 and R together with the N atom form a 5-7-membered ring which can additionally contain 1-2 hetero atoms, and
R5 is hydroxyl, Cι-C4alkyl or aryl.

2. A compound according to claim 1, in which X, Rj and R are as defined above and R is phenyl, naphthyl, tetrahydronaphthyl, indanyl or fluorenyl, each of which is unsubstituted or substituted by one or more R.

3. A compound according to claim 2, in which R2 is phenyl which is unsubstituted or substituted by one or more R.

4. A compound according to claim 3, in which R is fluorine, chlorine, bromine,
C1-C alkyl, cyclopropyl, cyclohexyl, trifluoromethyl, trifluoromethoxy, CrC alkoxy, morpholino, cyano, cyanomethyl, nitro, phenyl, phenoxy, hydroxyl, benzyloxy or
Ci- zalkylthio.

5. A compound according to claim 1, in which X, Rx and R are as defined above and R2, as heteroaryl, is a 5- or 6-membered heterocycle which has aromatic character and which is unsubstituted or substituted by one or more substituents R.

6. A compound according to claim 5, in which R2 is pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, each of which is unsubstituted or substituted by one or more substituents R.

7. A compound according to claim 5, in which R is pyrazolyl, thiazolyl, thiadiazolyl, thienyl, isothiazolyl, isoxazolyl, triazolyl or tetrazolyl, each of which is unsubstituted or substituted by one or more R.

8. A compound according to claim 1, in which X, Rj and R are as defined above and R2 is a heterocycle which is unsubstituted or substituted by one or more R and to which benzene is fused, or a phenyl group to which a heterocycle is fused.

9. A compound according to claim 8, in which R2 is quinolinyl, isoquinolinyl,
benzimidazolyl, benzothiazolyl, benzoxyazolyl, phthalazinyl, benzocoumarinyl, benzothiadiazolyl, carbazyl, indolyl or indazolyl, each of which is unsubstituted or substituted by one or more R.

10. A compound according to claim 1, in which X, Rj and R are as defined above and R2 is methylenedioxyphenyl or ethylenedioxyphenyl, each of which is unsubstituted or substituted by one or more halogen, methyl or methoxy.

11. A compound according to claim 10, in which the methylene or ethylene bridge is substituted by fluorine.

12. A compound according to claim 1, in which X, Rx and R are as defined above and R is a heterocycle which is unsubstituted or substituted by one or more R and to which a second heterocycle is fused.

13. A compound according to claim 12, in which R2 is purinyl, pteridinyl,
pyrazolo[3,4-b]pyridyl or naphthyridinyl, each of which is unsubstituted or substituted by one or more R.

14. A compound according to claim 2, in which X is CH and R2 is phenyl which is monosubstituted to trisubstituted by identical or different substituents from the group comprising halogen, C -C^alkyl, C1-C2alkoxy, CN and CF3.

15. A process for the preparation of compounds of the formula I according to claim 1, which comprises reacting an azo oxime of the formula II


in which Rj and R2 are as defined above, with a benzyl alcohol derivative of the general formula DI


in which U is a leaving group and X is CH or N.

16. A process according to claim 15, in which U is chlorine, bromine, iodine, mesyloxy or tosyloxy.

17. A process for the preparation of compounds of formula I according to claim 1 which comprises reacting a keto ester of the general formula VI


in which Ri and R2 are as defined above, with a methoxymethyltriphenylphosphonium salt of the formula VII or with O-methylhydroxylamin hydrohalide of the formula m, respectively,

CH3-O-NH2.H-Hal (VTH)

in which Ph is phenyl and Z and Hal represent chloride, bromide or iodide.

18. A process for the preparation of compounds of formula I according to claim 1, wherein X is CH which comprises reacting a phenyl acetate derivative of the general formula X


in which Rx and R2 are as defined in claim 1, with methylformate in a basic medium to . obtain, as an intermediate product, the corresponding 3-hydroxy acrylic acid methylester which is then subjected to methylation.

19. A process according to claim 18 wherein the methylation step is effected by methyl iodide, dimethyl sulfate or diazomethan.

20. A fungicidal composition which comprises, as active ingredient, a compound of the formula I according to claim 1 together with a suitable carrier material.

21. A composition according to claim 20 which comprises, as active ingredient, a compound according to one of claims 2 to 13.

22. A composition according to claim 20 which comprises, as active ingredient, a compound according to claim 14.

23. A method for controlling or preventing fungus infestation on plants, parts of plants or the locus where they are growing which comprises the application of a compound of the formula I.

24. A method according to claim 23 which comprises the application of a compound according to one of claims 2 to 13.

25. A method according to claim 23 which comprises the application of a compound according to claim 14.

26. A keto ester of the general formula VI


in which Rx and R2 are as defined in claim 1.

27. A phenyl acetate derivative of the general formula X


in which Rx and R are as defined in claim 1.