3-aryl-1,2,4-triazone derivatives with herbicidal properties

Details 3-aryl-1,2,4-triazone derivatives with herbicidal properties 3-aryl-1,2,4-triazone derivatives with herbicidal properties

2000-09-20

2002-07-30

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S263400, C548S263600

Reexamination Certificate

active

06426318

ABSTRACT:

The invention relates to novel substituted N-aryl nitrogen-containing heterocyclic compounds, processes for their preparation and their use as herbicides.
It is known that certain N-aryl nitrogen-containing heterocyclic compounds have herbicidal properties (cf. EP 11693, DE 2952685, DE 3026739, U.S. Pat. Nos. 4,276,420, 4,326,878, WO 94/14817). However, the compounds known from the patent applications mentioned have not acquired noteworthy importance.
The novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I)
in which
Q
1
represents oxygen or sulfur,
Q
2
represents oxygen or sulfur,
R
1
represents hydrogen, cyano or formyl or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkenyloxy, alkylthio, alkenylthio, alkenylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,
R
1
furthermore represents alkenyl or alkinyl, in each case optionally substituted by halogen,
R
1
furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
R
1
furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl,
R
2
represents hydrogen, cyano or formyl, or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkenylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,
R
2
furthermore represents alkenyl or alkinyl, in each case optionally substituted by halogen,
R
2
furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
R
2
furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl, and
Ar represents the substituted monocyclic or bicyclic aryl or heteroaryl grouping defined below.
in which
R
3
represents hydrogen or halogen,
R
4
represents hydrogen or halogen,
R
5
represents cyano, carboxyl, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl or halogen, or represents alkyl alkoxy or alkoxycarbonyl, in each case optionally substituted by halogen,
R
6
represents the following grouping
—A
1
—A
2
—A
3
in which
A
1
represents a single bond, or represents oxygen, sulfur, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl alkoxy, aryl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl,
A
1
furthermore represents alkanediyl, alkenediyl azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
A
2
represents a single bond, or represents oxygen, sulfur, —SO—, —SO
2
—, or the grouping —N—A
4
—, in which A
4
represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A
2
furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
A
3
represents hydrogen, with the proviso that in this case A
1
and/or A
2
do(es) not represent any single bond,
A
3
furthermore represents hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl or halogen, or represents alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)-phosphoryl, in each case optionally substituted by halogen or alkoxy,
A
3
furthermore represents alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkenylthio, alkinylamino or alkinyloxycarbonyl, in each case optionally substituted by halogen,
A
3
furthermore represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, in each case optionally substituted by halogen, cyano, carboxyl, alkyl and/or alkoxy-carbonyl,
A
3
furthermore represents aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, in each case optionally substituted by nitro, cyano, carboxyl, halogen, alkyl, halogenalkyl, alkyloxy, halogenalkyloxy and/or alkoxycarbonyl,
A
3
furthermore represents in each case optionally completely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy or furylalkoxy, or represents perhydropyranylalkoxy or pyridylalkoxy, and
R
7
represents hydrogen or halogen,
or in each case two adjacent radicals —R
3
and R
4
,R
4
and R
5
, R
5
and R
6
or R
6
and R
7
—together represent one of the following groupings
—Q
3
—CQ
4
—, —Q
3
—CQ
4
—Q
5
—, —Q
3
—C(R
8
,R
9
)—Q
5
—, —C(R
8
,R
9
)—CQ
4
—, —C(R
8
,R
9
)—Q
3
—CQ
4
—, —Q
3
—C(R
8
,R
9
)—C(R
8
,R
9
)—, —Q
3
—C(R
8
,R
9
)—C(R
8
,R
9
)—Q
5
—, C(R
8
,R
9
)—C(R
8
,R
9
)—CQ
4
—, —Q
3
—C(R
8
)═C(R
8
)—, —C(R
8
)═C(R
8
)—CQ
4
—, —Q
3
—C(R
8
,R
9
)—CQ
4
—, —N(R
10
)—C(R
8
,R
9
)—CQ
4
—, —C(R
8
)═N—, —Q
3
—CQ
4
—C(R
8
,R
9
)—, —Q
3
—CQ
4
—N(R
10
)—, —Q
3
—C(R
8
,R
9
)—CQ
4
—N(R
10
)—, —C(R
8
,R
9
)—Q
3
—CQ
4
—N(R
10
)—, —C(R
8
,R
9
)—C(R
8
,R
9
)—N(R
10
) —, —C(R
8
,R
9
)—C(R
8
,R
9
)—CQ
4
—N(R
10
)—, —C(R
8
)═C(R
8
)—N(R
10
)—, —C(R
8
)═C(R
8
)—CQ
4
—N(R
10
)—, —C(R
8
,R
9
)—CQ
4
—N(R
10
)—, —N(R
10
)—C(R
8
,R
9
)—CQ
4
—N(R
10
)—, —C(R
8
)═N(R
10
)—, —Q
3
C—Q
4
—C(R
8
,R
9
)—N(R
10
)—, Q
3
—C(R
8
R
9
)—(R
8
,R
9
)—CQ
4
—N(R
10
)—
in which
Q
3
, Q
4
and Q
5
are identical or different and in each case represent oxygen or sulfur,
R
8
and R
9
are identical or different and individually represent hydrogen halogen or alkyl or together represent alkanediyl, and
R
10
represents hydrogen or hydroxyl, or represents alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl which are optionally substituted by cyano, halogen, alkoxy, alkyl-carbonyl or alkoxy carbonyl, or represents alkenyl or alkinyl, in each case optionally substituted by halogen, or represents cycloalkyl or cycloalkylalkyl, in each case optionally substituted by halogen or alkyl, or represents alkoxy or alkenyloxy, in each case optionally substituted by halogen, or represents arylalkyl or arylalkoxy, in each case optionally substituted by cyano, halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy,
have now been found, the already known compounds 4-(3,4-dichlorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and 4-(4-choro-3-trifluoromethylphenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one (cf DE 2952685 and DE 3026739) being excluded by disclaimer.
The compounds isomeric to the substituted N-aryl nitrogen-containing heterocyclic compounds of the formula (I), of the formulae (Ia) and (Ib)
in which
Q
1
, Q
2
, R
1
, R
2
and Ar have the abovementioned meanings, have furthermore also been found.
The novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I) and, where appropriate, the compounds of the formulae (Ia) or (Ib) are obtained when
(a) (thio)semicarbazide derivatives of the general formula (II)
in which Ar
Q
1
, Q
2
, R
1
, R
2
and Ar have the abovementioned meanings and
R represents alkyl,
are subjected to a cyclizing condensation reaction, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and thereafter, if appropriate, electrophilic or nucleophilic substitution reactions are carried out in the customary manner in the context of the definition of the substituents,
or when
(b) aryliminoheterocyclic compounds of the general formula (III)
in which
Q
1
, Q
2
, R
1
, R
2
and Ar have the abovementioned meanings,
or compounds of the formula (Ia) or (Ib)—above—
are isome

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