Phenylpyrazoles with a herbicidal activity

Details Phenylpyrazoles with a herbicidal activity Phenylpyrazoles with a herbicidal activity

2000-08-03

2001-07-24

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S142000, C548S186000, C548S187000, C548S205000, C548S248000, C548S365100, C548S365700

Reexamination Certificate

active

06265351

ABSTRACT:

The present invention relates to new phenylpyrazoles. More specifically, the present invention relates to new phenylpyrazoles having a high herbicidal activity, the processes for their preparation and their use as herbicides for controlling weeds in agricultural crops.
Phenylpyrazoles with a herbicidal activity are de- scribed, among others, in European patent applications EP 361,114, EP 447,055, EP 839,808 and Japanese patent applications JP 3,151,367, JP 3,163,063.
These products, however, are not always satisfactory from the point of view of herbicidal activity with respect to weeds, and in addition have a poor selectivity, with the result that they are generally phytotoxic also with respect to the most important agricultural crops.
The Applicant has now found new phenylpyrazoles which not only have a high herbicidal activity with respect to numerous weeds but, at the same time, also have a low phytotoxicity towards various crops of agrarian interest and can therefore be used as selective herbicides.
The object of the present invention therefore relates to new phenylpyrazoles having general formula (I):
wherein:
R
1
and R
2
, the same or different, represent a C
1
-C
4
alkyl or haloalkyl group;
X represents a halogen atom;
X
1
represents a hydrogen atom, a chlorine atom or a fluorine atom;
X
2
represents a chlorine atom, a bromine atom, a C
1
-C
4
haloalkyl group, a C
1
-C
4
haloalkoxyl group;
Y represents an oxygen atom or a sulfur atom;
R represents a hydrogen atom or a C
1
-C
4
alkyl group;
n represents 0 or 1;
E represents one of the following heterocyclic groups:
2-furanyl, 3-furanyl, 2-thiophenyl, 3-thiophenyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-triazol-3-on-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 5-tetrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,3,4-oxadiazol-2-yl, 1,3,4-oxadiazol-2-on-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-2-on-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; said groups can be substituted by one or more groups—the same or different—selected from a halogen atom, a C
1
-C
6
alkyl or haloalkyl group, a C
1
-C
6
alkoxyl or haloalkoxyl group, a C
2
-C
6
alkoxyalkyl or haloalkoxyalkyl group, a C
1
-C
6
alkylthio or haloalkylthio group, a C
1
-C
6
alkylsulfinic or haloalkylsulfinic group, a C
1
-C
6
alkylsulfonic or haloalkylsulfonic group, an alkoxycarbonyl or haloalkoxycarbonyl group, an aminocarbonyl group optionally substituted by one or two C
1
-C
4
alkyl groups or by a C
2
-C
5
alkylene chain, a cyano group, a formyl group, an alkylcarbonyl or haloalkylcarbonyl group, an alkoxyiminoalkyl or haloalkoxyiminoalkyl group, a phenyl group optionally substituted, in turn, by halogen atoms, C
1
-C
4
alkyl or haloalkyl groups, C
1
-C
4
alkoxyl or haloalkoxyl groups.
Specific examples of compounds having general formula (I) which are of interest for their herbicidal activity are:
1) 4-chloro-3-[4-chloro-2-fluoro-5-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)phenyl]-5-fluoromethoxy-1-methylpyrazole;
2) ethyl 2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluoro-phenoxymethyl]-3-furancarboxylate;
3) 4-chloro-3-[4-chloro-2-fluoro-5-(5-methyl-1,3,4-thiadiazol-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
4) 4-chloro-3-[4-chloro-2-fluoro-5-(5-ethylthio-1,3,4-thiadiazol-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
5) 4-chloro-3-[4-chloro-2-fluoro-5-(5-ethylsulfonyl-1,3,-4-thiadiazol-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
6) 4-chloro-3-{4-chloro-2-fluoro-5-[5-(1,1,2,2-tetrafluoroethylthio)-1,3,4-thiadiazol-2-yloxy]phenyl}-5-difluoromethoxy-1-methylpyrazole;
7) 4-chloro-3-[4-chloro-2-fluoro-5-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)phenyl]-5-(1,1,2,2-tetrafluoroethoxy)-1-methylpyrazole;
8) ethyl 2-{2-chloro-5-[4-chloro-5-(1,1,2,2-tetrafluoroethoxy)-1-methylpyrazol-3-yl]-4-fluorophenoxymethyl}-3-furancarboxylate;
9) methyl 3-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluoro-phenoxymethyl]-2-thiophenecarboxylate;
10) 4-chloro-3-[4-chloro-2-fluoro-5-(5-formylthiophen-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
11) 4-chloro-3-[4-chloro-2-fluoro-5-(5-methoxyiminomethylthiophen-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
12) 4-chloro-3-[4-chloro-2-fluoro-5-(4-formyl-2-methylthiazol-5-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
13) 4-chloro-3-[4-chloro-2-fluoro-5-(4-ethoxyiminomethyl-2-methylthiazol-5-yloxy)phenyl]-5-difluoromethoxy-1-methyl-pyrazole;
14) 4-chloro-3-[4-chloro-2-fluoro-5-(2-methylthiazol-4-yl)methoxyphenyl]-5-difluoromethoxy-1-methyl-pyrazole;
15) 4-chloro-3-[4-chloro-2-fluoro-5-(5-bromo-2-methylthiazol-4-yl)methoxyphenyl] -5-difluoromethoxy-1-methylpyrazole;
16) 4-chloro-3-[4-chloro-2-fluoro-5-(4-formyl-1,3-dimethylpyrazol-5-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole.
17) 4-chloro-3-[4-chloro-5-(1,3-dimethyl-4-methoxy-imino-methylpyrazol-5-yloxy)-2-fluorophenyl]-5-difluoromethoxy-1-methylpyrazole
18) ethyl 5-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxymethyl-3-isox-azole-carboxylate;
19) ethyl 5-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxymethyl-3-furoate;
20) ethyl 2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxymethyl-4-thiaz-ole-carboxylate;
21) 4-chloro-3-[4-chloro-5-(5-ethyl-1,3,4-thiadiazol-2-yloxy)-2-flurophenyl]-5-difluoromethoxy-1-methylpyrazole;
22) 4-chloro-3-(4-chloro-2-fluoro-5-(5-isopropyl-1,3,4-thiadiazol-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
23) 4-chloro-3-[4-chloro-2-fluoro-5-(5-methoxymethyl-1,3,4-thiadiazol-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
24) 4-chloro-3-{4-chloro-2-fluoro-5-[5-(3-trifluoromethyl-phenyl)-1,3,4-thiadiazol-2-yloxy]phenyl}-5-difluoromethoxy-1-methylpyrazole;
25) 4-chloro-3-[4-chloro-2-fluoro-5-(1-methyl-2-trifluoromethyl-1,3,4-thiadiazol-5-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole;
26) 4-chloro-3-[4-chloro-2-fluoro-5-(3-nitrothien-2-yloxy)phenyl]-5-difluoromethoxy-1-methylpyrazole
A further object of the present invention relates to processes for the preparation of compounds having general formula (I).
The compounds having general formula (I) can be obtained starting from a phenyl-pyrazolone having general formula (II) by reaction with a compound having general formula (III) to give a phenylpyrazolyl ether having general formula (IV) which is subsequently converted to the end product having general formula (I) by treatment with a halogenating agent, according to reaction scheme A.
Alternatively, the compounds having general formula (I) can be obtained from a phenylpyrazole having general formula (V) by treatment with a compound having general formula (VI), according to reaction scheme B.
In these formulae, E, R, R
1
, R
2
, X, X
1
, X
2
, Y and n have the same meanings described above;
L
1
represents a halogen atom or an OSO
2
R
L
group wherein R
L
represents a C
1
-C
4
alkyl or haloalkyl group or a phenyl optionally substituted by C
1
-C
4
alkyl or haloalkyl groups;
L
2
represents an L
1
group or, when n=0, it may also represent an SO
2
R
L
group wherein R
L
has the meanings defined above.
The reaction between the compound having general formula (II) and the compound having general formula (III) is preferably carried out in the presence of one or more inert organic solvents and in the presence of an inorganic or organic base, at a temperature ranging from −10° C. to the boiling point of the reaction mixture.
Organic solvents which can be used for the purpose are for example aromatic hyd

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