Carbamates and crop protection agents containing them

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – N-c doai

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514478, 514486, 514538, 514596, 514625, 560 27, 560 29, 560 34, 560 43, 560 45, 564 49, 564 51, 564 52, 564 53, 564211, A61K 3127, A61K 3117, C07C27128, C07C27528

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058247050

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BRIEF SUMMARY
DESCRIPTION

The present invention relates to carbamates and crop protection agents, in particular for controlling fungi, insects, nematodes and spider mites.
It is known that aniline derivatives, for example isopropyl N-phenylcarbamate or the corresponding 3-chlorophenyl ester (GB 574 995) or methyl N-3,4-dichloro-phenylcarbamate (BE 612 550) can be used as crop protection agents. However, their fungicidal action is unsatisfactory.
It has now been found, surprisingly, that carbamates of the formula I ##STR2## where the substituents have the following meanings: Z is methoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, C.sub.2 H.sub.5, CF.sub.3 or CCl.sub.3, alkenyl or alkynyl or X and Y may be condensed together to form an unsubstituted or substituted aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring, cyclopropylmethyl, cyclobutyl, --CH.sub.2 --CN, --CH.sub.2 OCH.sub.3, --CO.sub.2 CH.sub.3 or --S--R.sup.5, O-alkyl, O-alkenyl, O-alkynyl, O-cycloalkyl, O-cycloalkenyl or O--CO.sub.2 -alkyl, --S--, --CHR.sup.2 --O--N.dbd.C(R.sup.4)--, --CR.sup.2 .dbd.N--O--, --O--N.dbd.C(R.sup.4)--, --C.tbd.--C--, --CHR.sup.2 --CHR.sup.3 --, --CHR.sup.2 --O--CO--, --O--CHR.sup.2 -- or a single bond, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, heterocyclyl, hydrogen, unsubstituted or substituted alkylaryl, unsubstituted or substituted alkylhetaryl, unsubstituted or substituted alkylcycloalkyl or unsubstituted or substituted alkylcycloalkenyl, alkenyl, alkynyl or cycloalkyl, plant-tolerated acid addition products and base addition products have a good fungicidal, acaricidal, insecticidal and nematocidal action.
Acids for addition products are, for example, mineral acids, such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or nitric acid, or carboxylic acids, such as formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid, as well as proton-acidic compounds generally, for example saccharin.
Bases for base addition products are, for example, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and ammonium hydroxide.
The novel compounds of the formula I may be obtained in the preparation as mixtures of stereoisomers (E/Z isomers, diastereomers, enantiomers), which can be separated into the individual components in a conventional manner, for example by crystallization or chromatography. Both the individual isomers and mixtures thereof may be used as fungicides, acaricides, nematocides or insecticides, and form the subject of the present invention.
The abovementioned alkyl radicals may be substituted and are of 1 to 6 carbon atoms.
The abovementioned alkenyl and alkynyl radicals may be substituted and are of 2 to 6 carbon atoms.
The abovementioned cycloalkyl radicals are of 3 to 10 carbon atoms and are unsubstituted or substituted, for example by 1 to 4 identical or different substituents R.sup.6.
The abovementioned aryl radicals are of 6, 10 or 14 carbon atoms and are unsubstituted or substituted, for example by 1 to 4 identical or different substituents R.sup.6.
The abovementioned hetaryl radicals have 5 to 14 ring atoms, including from 1 to 4 hetero atoms selected from the group consisting of N, O and S, are unsaturated and are unsubstituted or substituted, for example by 1 to 4 identical or different substituents R.sup.6.
The above mentioned heterocyclyl radicals have 5 to 14 carbon atoms, including 1 to 4 hetero atoms selected from the group consisting of N, O and S, are saturated or partially unsaturated and are unsubstituted or substituted, for example by 1 to 4 identical or different substitutents R.sup.6.
The abovementioned cycloalkenyl radicals are of 5 to 14 carbon atoms and are unsubstituted or substituted, for example by 1 to 4 identical or different substituents R.sup.6.
Two adjacent substituents R.sup.6, together with the carbon atoms of which they are substituents, may form

REFERENCES:
patent: 4526608 (1985-07-01), Lee
patent: 4608385 (1986-08-01), Noguchi et al.
patent: 4666938 (1987-05-01), Takahashi et al.
patent: 4752615 (1988-06-01), Takahashi et al.
patent: 5100916 (1992-03-01), Johansson et al.
patent: 5436267 (1995-07-01), Komyoji et al.
Glowinski et al., CA 98: 121083, 1983.
CA107:77391, 1986.
CA106:49798, 1986.
CA91:168209, 1979.
CA86:150296, 1977.
CA83:178614, 1975.

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