Oxime derivatives and their use as pesticides

Details Oxime derivatives and their use as pesticides Oxime derivatives and their use as pesticides

1996-09-03

2001-01-23

Rotman, Alan L. (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S561000, C514S562000, C514S599000, C514S602000, C514S603000, C514S617000, C514S618000, C514S619000, C514S620000, C558S411000, C558S413000, C558S414000, C562S434000, C562S435000, C562S437000, C562S438000, C564S074000, C564S162000, C564S163000, C564S164000, C564S166000, C564S180000, C564S183000, C564S256000, C564S257000

Reexamination Certificate

active

06177463

ABSTRACT:

The invention relates to new oxime derivatives, to a plurality of processes for their preparation, and to their use as pesticides.
It is known that various substitutive alkoximino- and alkoxymethylene acetamides have fungicidal properties (cf., for example, EP-A 398 692, EP-A 468 775, DE-A 40 30 038 and WO-A 92/13 830).
However, the activity of these prior-art compounds is not entirely satisfactory in all fields of application, in particular when low application rates and concentrations are used.
New oxime derivatives of the general formula (I)
have been found,
in which
Ar represents in each case optionally substituted arylene or heteroarylene,
E represents a direct bond, or a 1-alkene-1,1-diyl group which has a radical R
1
in the 2-position, or represents a 2-aza-1-alkene-1,1-diyl group which has a radical R
2
in the 2-position, or represents a 3-aza-1-propene-2,3-diyl group which has a radical R in the 3-position and a radical R
1
in the 1-position, or represents a 1-aza-1-propene-2,3-diyl group which has a radical R
2
in the 1-position, or represents a 1,3-diaza-1-propene-2,3-diyl group which has a radical R in the 3-position and a radical R
2
in the 1-position, or represents an optionally substituted imino group (“azamethylene”, N—R
3
),
where
R represents alkyl,
R
1
represents hydrogen, halogen, cyano, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R
2
represents hydrogen, amino, cyano, or in each case optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R
3
represents hydrogen, cyano, or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,
G represents oxygen, or represents alkanediyl, alkenediyl, oxaalkenediyl or alkinediyl, each of which is optionally substituted by halogen, hydroxyl, alkyl, halogenoalkyl or cycloalkyl, or represents one of the following groups
—Q—CQ—, —CQ—Q—, —CH
2
—Q—; —Q—CH
2
—, —CQ—Q—CH
2
—, —CH
2
—Q—CQ—, —Q—CQ—CH
2
—, —Q—CQ—Q—CH
2
—, —N═N—, —S(O)
n
—, —CH
2
—S(O)
n
—, —CQ—, —S(O)
n
—CH
2
—, —C(R
4
)═N—O—, —C(R
4
)═N—O—CH
2
—, —N(R
5
)—, —CQ—N(R
5
)—, —N(R
5
)—CQ—, —Q—CQ—N(R
5
)—, —N═C(R
4
)—Q—CH
2
—, —CH
2
—O—N═C(R
4
)—, —N(R
5
)—CQ—Q—, —CQ—N(R
5
)—CQ—Q—, —N(R
5
)—CQ—Q—CH
2
—, —CQ—CH
2
— or —N═N—C(R
4
)═N—O—,
 where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R
4
represents hydrogen, cyano, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
5
represents hydrogen, hydroxyl, cyano, or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
X represents the groups —OX
1
, —SX
1
, —SOX
1
, —SO
2
X
1
or —NX
2
X
3
where
X
1
, X
2
and X
3
independently of one another represent hydrogen, or in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl, or
X
2
and X
3
together with the nitrogen atom form an optionally substituted heterocycle,
Y
1
represents hydrogen, or in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl, and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl, aryloxy, arylthio, arylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino.
Furthermore, it has been found that the new oxime derivatives of the general formula (I) are obtained by a process which comprises
a) reacting thiocarbonyl derivatives of the general formula (II)
in which
Ar, E, G, X
1
and Z have the abovementioned meanings,
with hydroxylamine derivatives of the general formula (III)
in which
Y
1
has the abovementioned meaning,
or with their acid addition salts, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary; or
b) alkylating amide derivatives of the general formula (IV)
in which
Ar, E, G, X
3
and Z have the abovementioned meanings,
in the customary manner and reacting the resulting imino derivatives of the formula (IVa)
in which
Ar, E, G, X
3
and Z have the abovementioned meanings and
Alk represents alkyl, preferably methyl,
if appropriate without isolation, with hydroxylamine derivatives of -the general formula (III) or with their acid addition salts, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary; or
c) alkylating amide derivatives of the general formula (V)
in which
Ar, E, G, Y
1
and Z have the abovementioned meanings,
in the customary manner and reacting the resulting oximes of the formula (Va)
(Va),
in which
Ar, E, G, Y
1
, Z and Alk have the abovementioned meanings,
if appropriate without isolation, with amines of the general formula (VI)
HNX
2
X
3
  (VI),
in which
X
2
and X
3
have the abovementioned meanings,
if appropriate in the presence of a diluent.
Compounds of the formula (I) where X=SOX
1
or SO
2
X
1
are obtained by oxidizing corresponding compounds of the formula (I) where X=SX
1
in the generally customary manner, such as, for example, by oxidation by means of hydrogen peroxide or organic peracids.
Finally, it has been found that the new oxime derivatives of the general formula (I) show a very potent fungicidal activity.
If appropriate, the compounds according to the invention may exist in the form of mixtures of various isomeric forms which are possible, in particular in the form of E and Z isomers, but, if appropriate, also in the form of optical isomers and diastereomers. Claimed are the E as well as the Z isomers and also any mixtures of all other isomers which are possible.
The invention preferably relates to compounds of the formula (I), in which
Ar represents in each case optionally substituted phenylene or naphthylene, or represents heteroarylene having 5 or 6 ring members of which at least one represents oxygen, sulfur or nitrogen and, if appropriate, one or two further ring members represent nitrogen, the substituents which are possible preferably being selected from the list which follows: halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl, alkenyloxy or alkinyloxy, each of which has 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each of which has 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or represents in each case divalent alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
E represents a direct bond or one of the groups which follow
 in which
Y represents oxygen, sulfur, methylene (CH
2
) or alkylimino (N—R),
R represents alkyl having 1 to 6 carbon atoms,
R
1
represents hydrogen, halogen, cyano, or represents alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which have 1 to 6 carbon atoms in the alkyl radical and each of which is optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy,
R
2
represents hydrogen, amino, cyano, or represents alkyl, alkoxy, alkylamino or dialkylamino, each of which have 1 to 6 carbon atoms in the alkyl radical and each of which is optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy, and
R
3
repr

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