Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1998-02-10
1999-07-06
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514587, 558413, A01N 4708, C07C25533
Patent
active
059198257
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new hydroximic acid derivatives for use in plant protection. It also relates to the fungicidal and arthropodicidal compositions based on these compounds and to the processes for controlling fungal diseases of crops, as well as destruction of arthropods, using these compounds.
Alkoximino derivatives and oxime ethers compounds are known as fungicides and are respectively disclosed in WO 94/14761 and EP 617014.
Hydroximic acid derivatives for use in controlling fungal diseases are known from EP 463488 and from EP 370629.
One aim of the present invention is to provide a new family of hydroximic acid derivatives so as to have more choice in the available products. It is desirable indeed to have more products available so as to have various spectra of activity and to make it possible to have more appropriate control of fungal diseases according to the particular problems which are to be solved.
Another aim of the present invention is to provide new hydroximic acid derivatives which have improved properties in the treatment of fungal diseases and destructive arthropods of crops.
Another aim of the present invention is to provide compounds which have an improved use spectrum, in the field of fungal diseases, especially for the treatment of fungal diseases of rice, cereals, fruit trees and vegetables, vine grapes and sugar beet.
It has not been found that these aims could be achieved, in all or in part, by means of the products of the invention, described hereinbelow.
The invention provides compounds which are hydroximic acid derivatives of general formula (I): ##STR3## wherein:
G is either G1 or G2 or G3 or G4 of formula: ##STR4##
X.sub.1, X.sub.2, X.sub.3 are independently a hydrogen or halogen atom; a hydroxy, mercapto, nitro, thiocyanato, azido group, cyano group; alkylthio, haloalkylthio, cyanoalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, these alkyl or alkoxy being lower radicals, alkynyloxy, alkenylthio, alkynylthio, these alkyl or alkenyl or alkynyl being lower radicals,
R.sub.1, R.sub.2 are independently a hydrogen atom, or a alkyl or haloalkyl, a cycloalkyl or halocycloalkyl, cyano, alkoxyalkyl, alkoxycarbonyl; or R.sub.1 and R.sub.2 can form together a divalent radical such as an alkylene group, these alkyl or alkoxy or alkylene being lower radicals,
R.sub.3 is a hydrogen atom, or a alkyl or haloalkyl, a cycloalkyl or halocycloalkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, haloalkoxyalkyl, dialkylaminoalkyl, an optionally substituted phenyl or an optionally substituted benzyl group, these alkyl or alkoxy or alkenyl or alkynyl being lower radicals,
W is an oxygen or a sulfur atom, SO or SO.sub.2
R.sub.4, R.sub.5 are a lower alkyl group,
R.sub.6, R.sub.7 are independently a hydrogen atom or a lower alkyl group.
In the compounds of formula (I), there are 4 different stereoisomers (E,E or E,Z or Z,E or Z,Z) depending on the configuration of each of the 2 double bonds. These E or Z denomination could be replaced by the corresponding name of syn and anti, or cis and trans. These denominations are well known in the art. In the instant specification, in such denomination EZ, EE or ZE or ZZ, the first letter refers to the configuration of the G group and the second letter refers to the configuration of the hydroximic group.
There may also be in some cases optically active carbons.
Formula (I) and the present invention include also the stereoisomers (including enantiomers) of these compounds, either separated or in mixtures.
In the present text, the generic terms have the following meanings: up to 6 carbons; "hydroximic acid derivatives" (with O--C.dbd.N--O group) and the "thiohydroximic acid derivatives" (with S--C.dbd.N--O).
More specific examples of groups which may be used in the invention are: isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, tert-pentyl, hexyl group, cyclohexyl group, pentoxy group, isopropylthio, butylthio, pentylthio, dichloromethyl, trifluoromethyl, 1-chloroethyl, 2-iodoethyl, 3-chloropropyl, 2-methyl
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patent: 5292759 (1994-03-01), Brand et al.
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patent: 5449803 (1995-09-01), Watanabe et al.
patent: 5510344 (1996-04-01), Cliff et al.
Gant Daniel B.
Kirio Yoshie
Maeda Takako
Milligan Bruce
Perez Joseph
Rhone-Poulenc Agrochimie
Richter Johann
Sackey Ebenezer
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