N-(ortho-substituted benzyloxy) imine derivatives and their use

Details N-(ortho-substituted benzyloxy) imine derivatives and their use N-(ortho-substituted benzyloxy) imine derivatives and their use

1997-04-03

1999-01-26

Lambkin, Deborah C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

514538, 564254, 564256, 560 35, A01N 3324, A01N 3712, C07C24900, C07C22900

Patent

active

058639519

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/03802 Sep. 26, 1995.
The present invention relates to oxime ethers of the general formula I ##STR2## and to their isomers and isomer mixtures which are possible in which a) alkoxycarbonyl, substituted or unsubstituted di(C.sub.1 -C.sub.6 alkyl)aminocarbonyl, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl-S(O).sub.n, substituted or unsubstituted aryl-S(O).sub.n, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclylcarbonyl; and halogen atoms; C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.2 alkyl; C.sub.2 -C.sub.6 alkenyl which is unsubstituted or substituted by 1 to 3 halogen atoms; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, and
The compounds according to the invention have fungicidal, acaricidal and insecticidal properties and are suitable as agrochemical active ingredients for use in agriculture.
The invention furthermore relates to a process for the preparation of the compounds according to the invention and to fungicidal, acaricidal and insecticidal compositions which comprise such compounds as active ingredients, and to the use of such compounds and compositions for controlling phytopathogenic fungi, Acarina and insects, and for preventing such an attack.
If asymmetric carbon atoms exist in the compounds of the formula I, the compounds occur in optically active form. In any case, the compounds will aliphatic and the oximino double bonds. Atropisomerism may furthermore occur. The formula I is intended to embrace all these isomeric forms which are possible and also their mixtures, for example racemic mixtures and any
Depending on the number of the carbon atoms, alkyl and alkoxy groups are straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, sec-pentyl, tert-pentyl, n-hexyl and the like.
Cycloalkyl is to be understood as meaning cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example vinyl, 1-methylvinyl, allyl, 1-butenyl, isopropenyl.
Alkynyl is, for example, ethynyl, 1-propynyl or 1-butynyl.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Haloalkyl can have identical or different halogen atoms.
Substituents of the substituted alkoxycarbonyl, dialkylaminocarbonyl and alkyl-S(O).sub.n groups are, inter alia, 1 to 5 halogen atoms, cyano, methoxy, methylthio, cyclopropyl, alkenyl, alkynyl, phenyl.
Substituents of the substituted aryl-S(O).sub.n, heteroaryl and heterocyclyl groups are, inter alia, C.sub.1 -C.sub.4 alkyl, halogen, cyano, nitro, C.sub.1 C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, halo-C.sub.1 -C.sub.2 alkyl, halo-C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl.
1 to 3 substituents may exist independently of one another.
Aryl is phenyl or naphthyl, preferably phenyl.
The term heteroaryl includes furan, pyrrole, and aromatic 5-membered rings having two to three and six-membered rings having one to three identical or different hetero atoms N, O or S, all of which can be benzo-fused, and also the radical benzothienyl. Other individual examples which may be mentioned are pyridine, pyrimidine, pyrazine, thiazole, oxazole, isoxazole, isothiazole, triazine, quinoline, isoquinoline, pyridazine, pyrazole, imidazole, quinazoline, quinoxaline, benzimidazole, benzofuran, indole, isoindole, benzothiazole, thiadiazole.
The term heterocyclyl represents 5- to 7-membered rings which have 1-3 identical or different hetero atoms N, O and/or S. Examples are .DELTA..sup.2 -oxazoline, .DELTA..sup.2 -thiazoline; 5,6-dihydro-4H-1,3-thiazine; 5,6-dihydro4H-1,3-oxazine, and furthermore pyrrolidine, piperidine, morpholine, 4-alkylpiperidine, azepine.
Preferred within the scope of the invention are the following combinations of substituents: alkoxycarbonyl or substituted or unsubstituted di(C

REFERENCES:
patent: 5104872 (1992-04-01), Tsubata et al.
patent: 5238956 (1993-08-01), Clough et al.
International Search Report, PCT/EP95/03802, (1996).

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