Substituted 3-aryl-pyrazoles

Details Substituted 3-aryl-pyrazoles Substituted 3-aryl-pyrazoles

2002-10-24

2003-05-06

Rotman, Alan L. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S375100, C514S406000

Reexamination Certificate

active

06559102

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted 3-aryl-pyrazoles, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is known that certain substituted 3-aryl-pyrazoles have herbicidal properties (cf. EP-A-361114, EP-A-447055, WO-A-92/02509, WO-A-92/06962, WO-A-94/26109, WO-A-95/33728, WO-A-97/40018, WO-A-97/46535). However, the herbicidal activity of these compounds and their compatibility with crop plants are not always entirely satisfactory.
SUMMARY OF THE INVENTION
Substituted 3-aryl-pyrazoles have the general formula (I)
n, Q, R
1
, R
2
, R
3
, R
4
, R
5
, and X are as described.
DETAILED DESCRIPTION
This invention, accordingly, provides the novel substituted 3-aryl-pyrazoles of the general formula (I)
in which
n represents the numbers 0, 1, 2, 3, 4 or 5,
Q represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(C
1
-C
4
-alkyl),
R
1
represents hydrogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carton atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,
R
2
represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy or alkinylthio having in each case 2 to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,
R
3
represents hydrogen, halogen or optionally cyano-, halogen-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl- or C
1
-C
4
-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms,
R
4
represents hydrogen, cyano, thiocarbamoyl or halogen,
R
5
represents cyano, thiocarbamoyl, halogen, or represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, and
X represents hydroxyl, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, represents in each case optionally hydroxyl-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-(C
1
-C
4
-alkyl)-amino-carbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkoxy-substituted, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents dialkylaminocarbonyl having 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkoxy-carbonyl-, C
1
-C
4
-alkylamino-carbonyl- or di-(C
1
-C
4
-alkyl)-amino-carbonyl-substituted alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl having in each case up to 6 carbon atoms,
except for the previously known compounds 4-chloro-3-[4-chloro-2-fluoro-5-(4-nitro-phenoxy)-phenyl]-1-methyl-5-trifluoromethyl-1H-pyrazole, 4-chloro-3-[4-chloro-2-fluoro-5-(4-trifluoromethyl-phenoxy)-phenyl]-1-methyl-5-trifluoromethyl-1H-pyrazole, 4-chloro-3-[4-chloro-2-fluoro-5-(2-nitro-4-trifluoromethyl-phenoxy)-phenyl]-1-methyl-5-trifluoromethyl-1H-pyrazole and 4-chloro-3-[4-chloro-2-fluoro-5-(2-chloro-4-trifluoromethyl-phenoxy)-phenyl]-1-methyl-5-trifluoromethyl-1H-pyrazole (cf. WO-A-92/06962 and U.S. Pat. No. 5,281,571).
In the definition, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy.
Preferred substituents of the radicals listed in the formula (I) shown above are explained below:
n preferably represents the numbers 0, 1, 2 or 3.
Q preferably represents O (oxygen), S (sulphur), SO, SO
2
, NH or N(CH
3
).
R
1
preferably represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
R
2
preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propinyl, butinyl, propinyloxy, butinyloxy, propinylthio or butinylthio, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
R
3
preferably represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulfonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl.
R
4
preferably represents hydrogen, cyano, thiocarbamoyl, fluorine, chlorine or bromine.
R
5
preferably represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
X preferably represents hydroxyl, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, represents in each case optionally hydroxyl-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-p

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