Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1998-08-07
2001-01-30
Tsang, Cecilia (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S263200
Reexamination Certificate
active
06180567
ABSTRACT:
The invention relates to novel substituted sulphonylamino(thio)carbonyl compounds, to a plurality of-processes and novel intermediates for their preparation and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyl compounds such as, for example, the compounds N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide (cf EP 569810, Example 204), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide (cf. EP 569810, Example 239), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide (cf. EP 569810, Example 278), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide (cf. EP 569810, Example 329), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxarnide (cf. EP 569810, Example 366), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide (cf. EP 569810, Example 441), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide (cf. EP 569810, Example 532), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide (cf. EP 569810, Example 576), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide (cf. EP 569810, Example 607), N-(2-chloro-6-methoxy-carbonyl-phenylsulphonyl)- 1,3,4-oxadiazole-2-carboxamide (cf. EP 569810, Example 641), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide (cf. EP 569810, Example 701), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide (cf. EP 569810, Example 735), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide (cf. EP 569810, Example 757), N-(2-chloro-6-methoxy-carbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide (cf. EP 569810, Example 791), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide (cf. EP '569810, Example 861), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide (cf. EP 569810, Example 871), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide (cf. EP 569810, Example 918) and N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide (cf. EP 569810, Example 925) have herbicidal properties (cf. also EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). However, the activity of these compounds is not satisfactory in every respect.
This invention, accordingly, provides the novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I),
in which
A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N— or —N═CH—, or —CH═CH—,
Q represents oxygen or sulphur,
R
1
represents respectively optionally substituted alkyl, alkenyl, alkinyl. cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R
2
represents cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and
R
3
represents respectively optionally substituted heterocyclyl having 5 ring members of which at least one represents oxygen, sulphur or nitrogen and a further one to three may represent nitrogen,
and salts of compounds of the formula (I),
except for the prior art compounds N-(2-chloro-6-methoxycarbonyl-phenyl-sulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide (cf. EP 569810, Example 204), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide (cf. EP 569810, Example 239), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide (cf. EP 569810, Example 278), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide (cf. EP 569810, Example 329), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxamide (cf. EP 569810, Example 366), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide (cf. EP 569810, Example 441), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide (cf. EP 569810, Example 532), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide (cf. EP 569810, Example 576), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide (cf. EP 569810, Example 607), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide (cf. EP 569810, Example 641), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)- 1,3,4-thiadiazole-2-carboxamide (cf. EP 569810, Example 701), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxarnide (cf. EP 569810, Example 735), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide (cf. EP 569810, Example 757), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide (cf. EP 569810, Example 791), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide (cf. EP 569810, Example 861), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide (cf. EP 569810, Example 871), N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide (cf EP 569810, Example 918) and N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide (cf. EP 569810, Example 925) which are excluded by disclaimer.
The novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I), are obtained when
(a) sulphonamides of the general formula (II)
in which
A, R
1
and R
2
are each as defined above, are reacted with (thio)carboxylic acid derivatives of the general formula (III)
in which
Q and R
3
are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(b) sulphonyl iso(thio)cyanates of the general formula (IV)
in which
A, Q, R
1
and R
2
are each as defined above, are reacted with heterocycles of the general formula (V)
H—R
3
(V)
in which
R
3
is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) sulphonyl chlorides of the general formula (VI)
in which
A, R
1
and R
2
are each as defined above, are reacted with heterocycles of the general formula (V)
H—R
3
(V)
in which
R
3
is as defined above, and metal (thio)cyanates of the general formula (VII)
MQCN (VII)
in which
Q is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(d) sulphonyl chlorides of the general formula (VI)
in which
A, R
1
and R
2
are each as defined above,
are reacted with (thio)carboxamides of the general formula (VIII)
in which
Q and R
3
are each as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)
in which
A, Q, R
1
and R
2
are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
are reacted with heterocycles of the general formula (V)
H—R
3
(V)
in which
R
3
is as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by processes (a), (b), (c), (d) or (e) are, if desired, converted into salts by customary methods.
The novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
A represents oxygen, sulphur, NH, N-C
1
-C
4
-alkyl, N-phenyl, —CH═N— or —N═CH— or —CH═CH—,
Q represents oxygen or sulphur,
R
1
represents optionally cyano-, nitro-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl, represents respectively optionally cyano- or halogen-substituted C
2
-C
6
-alkenyl or C
2
-C6-alkinyl, represents resp
Dollinger Markus
Drewes Mark Wilhelm
Findeisen Kurt
Gesing Ernst Rudolf F.
Jansen Johannes R.
Bayer Aktiengesellschaft
Norris McLaughlin & Marcus P.A.
Tsang Cecilia
Wright Sonya
LandOfFree
Substituted sulphonylamino(thio)carbonyl compounds as... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted sulphonylamino(thio)carbonyl compounds as..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted sulphonylamino(thio)carbonyl compounds as... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2443108