Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-03-16
2001-06-26
Raymond, Richard L. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S189000, C548S338100, C548S366700, C558S417000, C560S024000, C560S029000, C560S030000
Reexamination Certificate
active
06252083
ABSTRACT:
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-dichlorophenylcarbamate (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
where the substituents have the following meanings:
Z is methoxy, NH
2
, NHCH
3
, N(CH
3
)
2
, CH
3
, C
2
H
5
, CF
3
or CCl
3
,
X and Y independently of one another are each hydrogen, F, Cl, Br, CF
3
, CN, NO
2
, alkoxy, alkenyloxy, alkynyloxy, alkyl, 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,
R
1
is unsubstituted or substituted alkyl, alkenyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, —CN
3
—CN, —CH
2
OCH
3
, —CO
2
CH
3
or —S—R
5
, O-alkyl, O-alkenyl, O-alkynyl, O-cycloalkyl, O-cycloalkenyl or O—CO
2
-alkyl,
A is —O—, —S—, —CR
2
═CR
3
—, CHR
2
—O—, —CHR
2
—S—, —CHR
2
—O—N═C(R
4
)—, —CR
2
═N—O—, —O—N═C(R
4
)—, —C≡C—, —CHR
2
—CHR
3
—, —CHR
2
—O—CO—, —O—CHR
2
— or a single bond,
B can be unsubstituted or substituted and is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, heterocyclyl, hydrogen, unsubstituted or substituted alkylaryl, unsubstituted or substituted alkylhetaryl, unsubstituted or substituted alkylcycloalkyl or unsubstituted or substituted alkylcycloalkenyl,
R
2
and R
3
independently of one another are each hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl,
R
4
is hydrogen, CN, alkyl, alkenyl, alkynyl, alkoxy or cycloalkyl,
R
5
is alkyl, cyclopropyl, cyclopropylmethyl or cyclobutyl, and their 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
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 subutituents R
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
6
.
The abovementioned 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 substituents R
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
6
.
Two adjacent substituents R
6
, together with the carbon atoms of which they are substituents, may form a carbocyclic hydrogenated, partially unsaturated or aromatic ring having 3 to 14 carbon atoms or a heterocyclic hydrogenated, partially unsaturated or heteroaromatic ring having 3 to 14 carbon atoms, including 1 to 4 hetero atoms selected from the group consisting of N, O and S.
R
6
may be unsubstituted or substituted, for example by 1 to 4 identical or different substituents R
7
, and R
6
is, for example, hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoxyimino, cycloalkenyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl or cycloalkenylsulfinyl.
R
7
is is any substituent and is, for example, hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaiminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, alkylsulfoxyl; alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl or cycloalkenylsulfinyl.
The abovementioned alkyl radicals may be substituted, are preferably of 1 to 6 carbon atoms and are, in particular, methyl, ethyl, propyl, such as n-propyl or isopropyl, butyl, such as n-butyl, isobutyl, tert-butyl or sec-butyl, pentyl or hexyl.
The abovementioned alkenyl radicals may be substituted, are preferably of 2 to 6 carbon atoms
Ammermann Eberhard
Doetzer Reinhard
Lorenz Gisela
Mueller Bernd
Roehl Franz
BASF - Aktiengesellschaft
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Raymond Richard L.
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