Imidic acid derivatives and their use as pesticides

Details Imidic acid derivatives and their use as pesticides Imidic acid derivatives and their use as pesticides

1999-04-28

2001-02-27

Kumar, Shailendra (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S523000, C558S409000, C564S103000, C564S105000

Reexamination Certificate

active

06194464

ABSTRACT:

The present invention relates to new imidic acid derivatives, to a plurality of processes for their preparation, and to their use as pesticides.
It is known that various substituted alkoximino- and alkoxymethyleneacetamides 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 efficacy 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 imidic acid derivatives have been found of the general formula (I)
in which
R represents hydrogen, cyano or the groups —CO—R
1
, —CS—R
2
and —S(O)
m
—R
3
,
where
R
1
, R
2
and R
3
in each case represent alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and
m represents the numbers 0, 1 or 2;
X represents alkoxy, alkylthio, amino, alkylamino or dialkylamino, or
X and R together with the carbon or nitrogen atom to which they are bonded represent a triazole radical of the formula
where
R
6
represents alkyl, hydroxyl, mercapto, amino, alkylamino or dialkylamino;
Ar represents in each case optionally substituted arylene or heteroarylene;
G represents a single bond, represents oxygen, or represents in each case optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl, alkenediyl, oxaalkenediyl, alkinediyl or 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
—, -Q—C(R
4
)=N—O—CH
2
—, —NH—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
Q represents oxygen or sulphur,
n represents the numbers 0, 1 or 2,
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; and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl,
with the exception of those compounds in which simultaneously R represents hydrogen, G represents oxygen or the group —OCH
2
— and Z represents in each case optionally substituted aryl or 2-pyridyl.
Furthermore, it has been found that the new imidic acid derivatives of the general formula (I) are obtained when
a) nitrites of the general formula (II)
in which
Ar, G and Z have the abovementioned meanings are reacted with (thio)alcohols of the general formula (III)
H—X
1
  (III)
in which
X
1
represents alkoxy or alkylthio,
or with their alkali metal salts, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
or
b) the imidates which can be obtained by process (a) which have the general formula (Ia)
in which
Ar, G, Z and X
1
have the abovementioned meanings,
are reacted with reactive acid derivatives, in particular with acid halides of the general formula (IV)
Hal-R   (IV)
in which
R has the abovementioned meaning and
Hal represents halogen,
or with the corresponding anhydrides, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
or
c) the imidates which can be obtained by process (a) which have the general formula (Ia)
in which
Ar, G, Z and X
1
have the abovementioned meanings, are reacted with cyanamide, of the formula (V),
NH
2
—CN   (V)
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
or
d) the imidic acid derivatives which can be obtained by processes (b) and (c) which have the general formula (Ib)
in which
Ar, G, Z and X
1
have the abovementioned meanings and
R′ represents cyano or the groups —COR
1
, —CSR
2
and —S(O)
m
R
3
, where R
1
, R
2
, R
3
and m have the abovementioned meanings,
are reacted with amines of the general formula (VI)
H—X
2
  (VI)
in which
X
2
represents amino, alkylamino or dialkylamino,
if appropriate in the presence of a diluent;
or
e) the imidic acid derivatives which can be obtained by processes (b) and (c) which have the general formula (Ic)
in which
Ar, G, Z and R′ have the abovementioned meanings,
are reacted with hydrazine or hydrazine hydrate, if appropriate in the presence of a diluent;
or
f) the imidates which can be obtained by process (a) which have the general formula (Ia)
in which
Ar, G, Z and X
1
have the abovementioned meanings,
are reacted with amines of the general formula (VI)
H—X
2
  (VI)
in which
X
2
has the abovementioned meaning,
if appropriate in the presence of a diluent.
Finally, it has been found that the new imidic acid derivatives of the general formula (I) exhibit a powerful fungicidal activity.
If appropriate, the compounds according to the invention can exist in the form of mixtures of various isomeric forms which are possible, in particular E and Z isomers. The invention claims not only the E and Z isomers, but also any mixtures of these isomers.
The invention preferably relates to compounds of the formula (I) in which
R represents hydrogen, cyano or the groups —CO—R
1
, —CS—R
2
and —S(O)
m
—R
3
,
where
R
1
, R
2
and R
3
represent in each case straight-chain or branched alkyl, alkoxy or alkylthio, each of which has 1 to 4 carbon atoms; amino or in each case straight-chain or branched alkylamino and dialkylamino, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, and
m represents the numbers 0, 1 or 2,
X represents in each case straight-chain or branched alkoxy or alkylthio, each of which has 1 to 4 carbon atoms;
 amino or in each case straight-chain or branched alkylamino and dialkylamino, each of which has 1 to 4 carbon atoms in the individual alkyl moieties,
X and R together with the carbon or nitrogen atom to which they are bonded represent a triazole radical of the formula
where
R
6
represents straight-chain or branched alkyl having 1 to 4 carbon atoms, hydroxyl, mercapto, amino or in each case straight-chain or branched alkylamino and dialylano, each of which has 1 to 4 carbon atoms in the individual alkyl moieties,
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, sulphur or nitrogen and, if appropriate, one or two further ring members represent nitrogen, the substituents which are possible preferably being selected from the following enumeration:
 halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, 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, halogenoalkylsulphinyl or halogenoalkylsulphonyl, 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, alkyl-sulphonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, and 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 ha

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