Aminosulfonylureas with herbicidal activity

Details Aminosulfonylureas with herbicidal activity Aminosulfonylureas with herbicidal activity

1999-10-21

2001-12-11

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S321000, C544S323000, C544S332000

Reexamination Certificate

active

06329323

ABSTRACT:

This invention relates to aminosulfonylureas.
More in particular, this invention relates to aminosulfonylureas possessing a high herbicidal activity, a process for their preparation and their application as herbicides for controlling weeds in agricultural cultures. Aminosulfonylureas with herbicidal activity have, among other things, been described in the U.S. Pat. Nos. 4,515,620, 4,559,081, 4,592,776, 4,622,065 and 4,666,508. However, these products turn out to have a very poor selectivity while generally being toxic to the most important agricultural cultures.
The applicant has now discovered new aminosulfonylureas which have a higher herbicidal activity against numerous weeds, exhibiting at the same time a low phytotoxicity to one or more of the cultivations of prime agricultural interest. Therefore, they have a higher cell selectivity.
The object of this invention are thus aminosulfonylureas of the following general formula (I):
in which:
R represents a halogen atom such as chlorine, fluorine, bromine or iodine; an alkylic or haloalkylic linear or branched C
1
-C
4
group; an alkoxylic or haloalkoxylic linear or branched C
1
-C
4
group;
N represents 0 or 1;
R
1
and R
2
, equal or different from each other, represent an atom of hydrogen; an alkylic or haloalkylic linear or branched C
1
-C
4
group; an alkoxylic or haloalkoxylic linear or branched C
1
-C
4
group; or, jointly, an alkylenic or oxyalkylenic C
2
-C
5
chain;
R
3
and R
4
, equal or different from each other, represent an atom of hydrogen; an alkylic or haloalkylic linear or branched C
1
-C
4
group; an alkoxyalkylic or haloalkoxyalkylic linear or branched C
3
-C
6
group; an alkenylic or haloalkenylic linear or branched C
3
-C
6
group; an alkynylic or haloalkynylic linear or branched C
3
-C
6
group;
R
5
and R
6
, equal or different from each other, represent an atom of hydrogen; a halogen atom such as chlorine, fluorine, bromine or iodine; an alkylic or haloalkylic linear or branched C
1
-C
6
group; an alkylaminic linear or branched C
1
-C
6
group; a dialkylaminic linear or branched C
2
-C
8
group; a cycloalkylic or cycloalkoxylic C
3
-C
6
group; a cycloalkylalkylic or cycloalkylalcoxylic C
4
-C
7
group;
Z represents CH or N.
The aminosulfonylureas of the general formula (I) are endowed with high herbicidal activity. Specific examples of aminosulfonylureas having the general formula (I) which are interesting for their herbicidal activity are:
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethyl- benzamide;
1-[(4,6-dimethoxypyrimidin-2-yl)-3-{[2-(1-pyrrolidinocarbonyl)phenyl]sulfamoyl}urea,
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethyl-N-methylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-ethylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxybenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-methoxy-N-methylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]benzamide;
2-[(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylmethylamino]-N,N-dimethylbenzamide;
N-cyclopropyl-2-[(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino]- benzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N-(2,2,2-trifluoroethyl)benzamide;
4-chloro-6-[(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino]-N,N-dimethylbenzamide;
3-chloro-6-[(4,6-dimethoxypyrimidin-2-yl) carbamoylsulfamoylamino]-N,N-dimethylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-5-fluoro-N,N-dimethylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-6-fluoro-N,N-dimethylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-5-methyl-N,N-dimethylbenzamide;
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-6-methyl-N,N-dimethylbenzamide;
N,N-dimethyl-2-[(4-methoxy-6-methylpyridin-2-yl) carbamoylsulfamoylamino]-benzamide;
N,N-dimethyl-2-[(4-methoxy-6-methylpyrimidin-2-yl) carbamoylsulfamoylamino]-benzamide.
N,N-dimethyl-2-[(4,6-dimethylpyrimidin-2-yl) carbamoylsulfamoylamino] benzamide.
The aminosulfonylureas having the general formula (I) of the present invention have an acidic nature and can therefore form salts with basic substances such as, for example, alkaline metal and alkaline earth hydroxides, amines and other organic bases, and quaternary amine salts.
The aminosulfonylureas having the general formula (I) in their salified form also fall within the scope of this invention and therefore constitute a further object of the same.
A further object of this invention is a process for the preparation of compounds having the general formula (I). The compounds having the general formula (I) may be obtained by a process including:
(a) reacting a heterocyclic amine having the general formula (II):
in which R
4
, R
5
, R
6
, and Z have the meanings as described above, with a halosulfonylisocyanate having the general formula (III):
X—SO
2
—NCO  (III)
in which X represents a halogen atom such as, for instance, chlorine, fluorine, or bromine, preferably chlorine, in the presence of an inert organic solvent, whereby a halosulfamoylurea of the following general formula (IV) is obtained:
in which X, R
4
, R
5
, R
6
, and Z have the meanings as described above;
(b) reacting of halosulfamoylurea having the general formula (IV) obtained in the step (a) with an aniline having the general formula (V):
in which R, R
1
, R
2
, and R
3
have the same meanings described above, in the presence or absence of a base, preferably in the presence of a base, and of an inert organic solvent.
The inert organic solvents useful in the steps (a) and (b) of the process described above are aromatic hydrocarbons (such as for example benzene, toluene, xylene, etc.), chlorinated hydrocarbons (such as for example, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene etc.), and ethers (such as, for example, ethyl ether, dimethoxyethane, tetrahydrofurane, dioxane, etc.).
The bases useful in the step (b) of the process described above are organic bases, preferably aliphatic amines such as, for example, triethylamine, etc.
The subject reaction steps (a) and (b) are performed at temperatures between −70° C. and the boiling temperature of the solvent employed, preferably between −20° C. and +30° C. The reaction of step (b), between aniline having the general formula (V) and halosulfamoylurea having the general formula (IV), may be conveniently performed without isolating said halosulfamoylurea (IV), by adding the aniline (V) and the base (diluted with the same inert organic solvent used in the step (a) of the above process), while operating in the same ambient in which the first passage was performed.
The heterocyclic amines having the general formula (II) and the halosulfonylisocyanates having the general formula (III) are compounds known in the art.
The anilines having the general formula (V) can, if not already known on their own, be prepared according to the methods known in the art.
The compounds having the general formula (I), objects of this invention, have evidenced interesting biological activities and, in particular, a high herbicidal activity which renders them suitable for use in the agricultural field to defend the useful cultures from weeds.
In particular, the compounds having the general formula (I) are effective in controlling, both before and after an emergency, numerous cotyledon and dicotyledon weeds. At the same time, these compounds show a compatibility or absence of toxic effects toward useful cultures, both while treating before and after emergence.
Examples of weeds effectively controlled by using the compounds having the general formula (I) as the object of this invention are:
Abutilon theofrasti, Amaranthus retroflexus, Amni maius, Capsella bursa pastor

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