Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1994-10-25
2001-11-13
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S256000, C514S269000, C514S347000, C514S357000, C514S359000, C514S424000, C514S427000, C514S438000, C514S445000, C514S471000, C544S311000, C544S319000, C544S335000, C546S292000, C546S335000, C546S337000, C548S267400, C548S550000, C548S561000, C549S065000, C549S077000, C549S479000, C549S496000
Reexamination Certificate
active
06316459
ABSTRACT:
The present invention relates to novel O-benzyloxime ethers and a method for controlling pests, in particular fungi, insects, nematodes and spider mites with these compounds.
It is known that substituted phenylacetic acid oxime derivatives can be used as fungicides (European Patent 253,213). However, their action is unsatisfactory.
We have found, surprisingly, that O-benzyloxime ethers of the general formula I
where
X is CH
2
, CH—C
1
-C
4
-alkyl, CH—C
1
-C
4
-alkoxy, CH—C
1
-C
4
-alkylthio or N—C
1
-C
4
-alkoxy,
Y is O, S or NR
5
,
R
1
, R
2
and R
5
are each H or C
1
-C
4
-alkyl,
Z
1
and Z
2
are identical or different and are each H, halogen, methyl, methoxy or cyano,
R
3
and R
4
are identical or different and are each hydrogen, cyano, straight-chain or branched C
1
-C
10
-alkyl, C
1
-C
4
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-halocycloalkyl, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, arylthio-C
1
-C
4
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
5
-haloalkenyl, C
3
-C
6
-cycloalkenyl, C
3
-C
6
-halocycloalkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
4
-alkylthio, benzylthio, C
1
-C
4
-alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C
1
-C
4
-alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C
1
-C
4
-alkyl, unsubstituted or substituted aryl-C
1
-C
4
-alkenyl, unsubstituted or substituted aryloxy-C
1
-C
4
-alkyl, unsubstituted or substituted arylthio-C
1
-C
4
-alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted hetaryl-C
1
-C
4
-alkyl, unsubstituted or substituted hetaryl-C
2
-C
4
-alkenyl, unsubstituted or substituted hetaryloxy-C
1
-C
4
-alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R
6
)
2
, where the radicals R
6
are identical or different and are each H, C
1
-C
6
-alkyl or unsubstituted or substituted phenyl, or
—CO—N(R
7
)
2
, where the radicals R
7
are identical or different and are each H or C
1
-C
4
-alkyl, substituents, in addition to hydrogen, being halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, C
1
-C
10
-alkoximino-C
1
- or C
2
-alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C
3
-C
6
-cycloalkyl, heterocyclyl or heterocyclyloxy, or
R
3
and R
4
together may form a carbocyclic or heterocyclic ring which may be substituted by the abovementioned substituents, and R
3
or R
4
may be halogen, or
may be
where
n is an integer from 1 to 4, and
R
8
is, or, when n>1, the R
8
's are identical or different and are each , H, halogen, cyano, nitro or substituted or unsubstituted C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,
have excellent fungicidal, insecticidal, nematicidal and acaricidal activity which is better than that of the known phenylacetic acid derivetives.
The fungicidal action is preferred.
The radicals stated for the general formula I may, for example, have the following meanings:
X may be C
1
-C
4
-alkylidene (eg. methylidene, ethylidene, n- or isopropylidene, n-, iso-, sec- or tert-butylidene), C
1
-C
4
-alkoxymethylidene (eg. methoxy-, ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tert-butoxymethylidene), C
1
-C
4
-alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene) or C
1
-C
4
-alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino),
Y may be O, S or NR
5
,
R
1
, R
2
and R
5
may each be H or C
1
-C
4
-alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl), Z
1
and Z
2
may be H, halogen (eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano, and
R
3
and R
4
may be identical or different and are each hydrogen, cyano, straight-chain or branched C
1
-C
10
-alkyl (eg. methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neopentyl, n-hexyl or n-decyl), C
1
-C
4
-haloalkyl (eg. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl), C
3
-C
6
-cycloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), C
3
-C
6
-halocycloalkyl (eg. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl), C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl), C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl (eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl,2-methylthioprop-2-yl,2-ethylthioprop-2-yl, 2-n- or isopropylthioprop-2-yl or 2-n-, iso-, sec- or tert-butylthioprop-2-yl), aryl(phenyl)thio-C
1
-C
4
-alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl), C
2
-C
6
-alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2-butenyl or 2-methyl-2-penten-5-yl), C
2
-C
5
-haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl), C
3
-C
6
-cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl), C
3
-C
6
-halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl), C
2
-C
4
-alkynyl (eg. ethynyl, 1-propynyl or 1-propargyl), C
1
-C
4
-alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy), C
1
-C
4
-alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or benzylthio, C
1
-C
4
-haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy),
N(R
6
)
2
(eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino), C
1
-C
4
-alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl or pivaloyl),
unsubstituted or substituted phenylcarbonyl (eg. benzoyl or 4-chlorobenzoyl),
unsubstituted or substituted benzylcarbonyl (eg.benzylcarbonyl), C
1
-C
4
-alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl or n-, iso-, sec- or tert-butoxycarbonyl),
unsubstituted or substituted phenoxycarbonyl (eq. phenoxycarbonyl or 4-chlorophenoxycarbonyl),
unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl),
—CO—N(R
7
)
2
(eg. aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl or N-methyl-N-phenylaminocarbonyl),
unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl),
unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy or anthryloxy),
unsubstituted or substituted arylthio (eg. phenylthio),
unsubstituted or substituted aryl-C
1
-C
4
-alkyl (eg. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl),
unsubstituted or substituted aryl-C
1
-C
4
-alkenyl (eg. phenyl-1-ethenyl, 2-phenyl-1-propenyl, 2,2-diphenylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl),
unsubstituted or substituted aryloxy-C
1
-C
4
-alkyl (eg. phenoxymethyl),
unsubstituted or substituted arylthio-C
1
-C
4
-alkyl (eg. phenylthiomethyl),
unsubstituted or substituted hetaryl (eg. pyridyl, 2-pyridyl, 3-pyridyl,
Ammermann Eberhard
Brand Siegbert
Harreus Albrecht
Kardorff Uwe
Kirstgen Reinhard
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