Pyrrolic compounds having a high herbicidal activity and...

Details Pyrrolic compounds having a high herbicidal activity and... Pyrrolic compounds having a high herbicidal activity and...

2000-06-15

2002-05-21

Higel, Floyd D. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S562000

Reexamination Certificate

active

06391827

ABSTRACT:

The present invention relates to new pyrrolic compounds having a herbicidal activity.
More specifically, the present invention relates to pyrrolic compounds having a high herbicidal activity, the process for their preparation and their use as herbicides for controlling weeds in agricultural crops. Pyrroles with a herbicidal activity are described, for example, in European patent application EP 351,641.
Pyrroles with a herbicidal activity are also described in patent application EP 369,262.
The Applicant has now found new pyrrolic compounds which, in addition to having an excellent herbicidal activity with respect to numerous weeds, also have limited toxicity towards various crops of agrarian interest and can therefore be used as selective herbicides.
The object of the present invention consequently relates to pyrrolic compounds having general formula (I)
wherein:
W represents a hydrogen, fluorine or chlorine atom;
U represents a halogen atom, an alkyl, haloalkyl group, a cyano group, a nitro group;
represents a hydrogen atom, a halogen atom, a C
1
-C
8
alkyl group, a C
1
-C
8
halogenalkyl group, a C
3
-C
6
cycloalkyl group, a C
4
-C
8
cycloalkylalkyl group, an alkenyl group, said groups can in turn be further substituted by one or more substituents selected from halogen atoms, C
1
-C
4
alkoxyl groups, C
1
-C
4
haloalkoxyl groups, C
1
-C
4
alkylthio groups, C
1
-C
4
haloalkylthio groups, C
1
-C
4
alkylsulfinic groups, C
1
-C
4
haloalkylsulfinic groups, C
1
-C
4
alkylsulfonic groups, haloalkylsulfonic groups;
or it represents a ZR, COR
1
, CO
2
R
2
, CH
2
CHR
3
CO
2
R
2
, CH═CHR
3
CO
2
R
2
, CR
4
═NOR
5
, CO—NR
6
R
7
, CN, NO
2
, NR
8
R
9
, NR
10
SO
2
R
11
, N(SO
2
R
11
)
2,
NR
12
—CO—R
13
, NR
14
—CO—OR
15
, NR
16
—CO—NR
17
R
18
group; Groups U and Q can be joined to each other by means of saturated carbon atoms and/or unsaturated carbon atoms, and/or C═Z
1
groups, and/or oxygen atoms, and/or S(O)
m
groups, and/or NR
19
groups to form cyclic rings having up to 9 members, in which the carbon atoms can be substituted with one or more C
1
-C
4
alkyl or haloalkyl groups;
T represents a hydrogen atom, a C
1
-C
8
alkyl or haloalkyl group, a C
1
-C
8
alkoxyalkyl or haloalkoxyalkyl group, a Z
2
R
11
group;
X represents a hydrogen atom, a halogen atom, a C
1
-C
8
halogenalkyl group, a CO
2
R
21
group, a CO—NR
6
R
7
group;
X
1
represents a hydrogen atom, a halogen atom, a C
1
-C
8
halogenalkyl group, a cyano group, a CO
2
R
22
group, a CO—NR
6
R
7
group;
Y represents a C
1
-C
8
alkyl or haloalkyl group, a cyano group, a Z
3
Y
1
group;
Y
1
represents a C
1
-C
8
alkyl or haloalkyl group;
Z, Z
2
, Z
3
represent O or S(O)n wherein n=0-1;
Z
1
represents O or S
m=
0
-2
R represents a hydrogen atom, a C
1
-C
8
alkyl group, a C
3
-C
6
cycloalkyl group, a C
4
-C
8
cycloalkylalkyl group, a C
2-C
8
alkenyl group, a C
2
-C
8
alkynyl group, an aryl group, an arylalkyl group, a heterocyclic group with 5 or 6 terms containing from 1 to 4 heteroatoms, the same or different, selected from N, O, S, a heterocyclylalkyl group; said groups can in turn be further substituted by one or more substituents selected from halogen atoms, C
1
-C
4
alkoxyl groups, C
1
-C
4
haloalkoxyl groups, C
1
-C
4
alkylthio groups, C
1-C
4
haloalkylthio groups, C
1
-C
4
alkylsulfinic groups, C
1
-C
4
haloalkylsulfinic groups, C
1
-C
4
alkylsulfonic groups, C
1
-C
4
haloalkylsulfonic groups, COOH groups, C
2
-C
6
alkoxycarbonyl groups, C
2
-C
6
haloalkoxycarbonyl groups, C
3
-C
8
alkoxycarbonylcarbonyl groups, C
3
-C
8
haloalkoxycarbonylcarbonyl groups, C
2
-C
6
alkylaminocarbonyl groups, C
3
-C
9
dialkylaminocarbonyl groups, C
3
-C
7
alkylaminocarbonylcarbonyl groups, C
4
-C
10
dialkylaminocarbonylcarbonyl groups, C
2
-C
6
alkylcarbonyl groups, C
2
-C
6
aloalkylcarbonyl groups, C
3
-C
8
alkoxyiminoalkyl groups, C
4
-C
8
alkoxyiminohaloalkyl groups, CHO groups, CN groups, NO
2
groups;
R
1
, R
2
, R
4
, R
5
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
, R
16
, R
19
, R
20
, R
21
, R
22
, represent a hydrogen atom, or a C
1
-C
6
alkyl or haloalkyl group, a C
3
-C
6
cycloalkyl group, a C
7
-C
12
arylalkyl group or an aryl group, said arylalkyl and aryl groups also optionally substituted;
R
3
represents a hydrogen atom, a halogen atom, or a C
1
-C
2
alkyl or haloalkyl group;
R
6
, R
7
represent a hydrogen atom, or a C
1
-C
6
alkyl group, a C
3
-C
6
cycloalkyl group, a C
7
-C
12
arylalkyl group or an aryl group, said arylalkyl and aryl groups also optionally substituted, or they jointly represent a C
2
-C
5
alkylene chain;
R
8
, R
9
represent a hydrogen atom, or a C
1
-C
6
alkyl group, a C
3
-C
6
cycloalkyl group, a C
7
-C
12
arylalkyl group or an aryl group, said arylalkyl and aryl groups also optionally substituted, or they jointly represent a C
2
-C
5
alkylene chain;
R
17
, R
18
represent a hydrogen atom, or a C
1
-C
6
alkyl group, a C
3
-C
6
cycloalkyl group, a C
7
-C
12
arylalkyl group or an aryl group, said arylalkyl and aryl groups also optionally substituted, or they jointly represent a C
2
-C
5
alkylene chain.
The pyrroles having general formula (I) have a high herbicidal activity.
Specific examples of arylpyrroles having general formula (I) which are of interest for their herbicidal activity are:
ethyl 5-(2,4-dibromo-1-methyl-5-trifluoromethyl pyrrol-3-yl)-2-chloro-4-fluorophenoxyacetate;
ethyl 5-(2,4-dichloro-1-methyl-5-trifluoromethyl pyrrol-3-yl)-2-chloro-4-fluorophenoxyacetate;
ethyl 2-chloro-5-(4-bromo-2-chloro-1-methyl-5-trifluoromethylpyrrol-3-yl)-4-fluorophenoxyacetate;
ethyl 2-chloro-5-(2-bromo-1-methyl-5-trifluoro methyl pyrrol-3-yl)-4-fluorophenoxyacetate;
3-[4-chloro-2-fluoro-5-(2-propinyloxy)phenyl]-2,4-dibromo-1-methyl-5-trifluoromethylpyrrole;
3-[4-chloro-2-fluoro-5-(2-propinyloxy)phenyl]-2,4-dichloro-1-methyl-5-trifluoromethylpyrrole;
4-bromo-3-[4-chloro-2-fluoro-5-(2-propinyloxy)phenyl]-2-chloro-1-methyl-5-trifluoromethylpyrrole;
2-bromo-3-[4-chloro-2-fluoro-5-(2-propinyloxy)phenyl]-1-methyl-5-trifluoromethylpyrrole;
methyl 2-chloro-5-(2,4-dibromo-1-methyl-5-trifluoromethyl pyrrol-3-yl)-4-fluorobenzoate;
1-methylethyl 2-chloro-5-(2,4-dibromo-1-methyl-5-trifluoro methylpyrrol-3-yl)-4-fluorobenzoate;
ethyl 2-chloro-5-(2,4-dibromo-1-methyl-5-trifluoromethyl pyrrol-3-yl)-4-fluorobenzoate;
N,N-dimethyl 2-chloro-5-(2,4-dibromo-1-methyl-5-trifluoro methylpyrrol-3-yl)-4-fluorobenzamide;
1- [2-chloro-5- (2,4-dibromo-1-methyl-5-trifluoro methylpyrrol-3-yl)-4-fluorobenzoyl]pyrrolidine;
4-chloro-3-(2,4-dichloro-5-nitrophenyl)-1-methyl-5-trifluoromethylpyrrole-2-carbonitrile;
N-[5-(2-cyano-4-chloro-1-methyl-5-trifluoromethylpyrrol-3-yl)-2,4-dichlorophenyl]bismethylsulfonamide;
N-[5-(2-cyano-4-chloro-1-methyl-5-trifluoromethylpyrrol-3-yl)-2,4-dichlorophenyl]methylsulfonamide.
A further object of the present invention relates to processes for the preparation of the compounds having general formula (I).
The pyrroles having general formula (I) can be prepared according to methods known to experts in the field and in particular by adapting to the specific substrates necessary, the known methods described in literature such as, for example, by G. P. Bean in “The Chemistry of Heterocyclic Compounds” “Pyrroles” (1990), vol. 1, chap. 2, pages 105-294 Ed. Wiley-New York and by R. G. Sundberg in “Comprehensive Heterocyclic Chemistry” (1984), vol. IV, chap. 5, pages 313-376.
More specifically, the compounds having general formula (I) can be prepared, for example, by reacting alkynes having general formula II:
with aminoacid derivatives having general formula (III)
The reaction can be carried out in an inert organic solvent and in the presence of a dehydrating agent, at a temperature ranging from 50° C. to the boiling point of the reaction mixture.
Examples of solvents suitable for the embodiment of the process are: benzene, toluene, xylene.
Examples of suitable dehydrating. agents are acetic anhydride, propionic anhydride, butyric anhydride, dicyclohexylcarbo

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