Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2001-09-05
2003-02-04
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S266000, C504S271000
Reexamination Certificate
active
06514910
ABSTRACT:
The present invention relates to a herbicidal mixture of a 3-heterocyclyl-substituted benzoyl derivative and an adjuvant, said mixture having synergistic action.
3-Heterocyclyl-substituted benzoyl derivatives are known and described, for example, in WO 96/26206, WO 97/41116, WO 97/41117 and Wo 97/41118.
EP-B-0584 227 discloses herbicidal compositions comprising substituted cyclohexanediones and nitrogen fertilizers.
The German-application P 19825588.8 discloses herbicidal mixtures based on a 3-heterocyclyl-substituted benzoyl derivative, a nitrogen-containing fertilizer and an adjuvant.
It is an object of the present invention to provide a herbicidal mixture which comprises 3-heterocyclyl-substituted benzoyl derivatives and whose herbicidal activity is higher than the activity of the pure active compound.
This object was achieved by a herbicidal mixture, comprising
a) a herbicidally effective amount of a 3-heterocyclyl-substituted benzoyl derivative of the formula I
where:
R
1
,R
2
are hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy;
R
3
is hydrogen, halogen, C
1
-C
6
-alkyl;
X is a heterocycle from the group consisting of isoxazolyl, 4,5-dihydroisoxazolyl and thiazolyl, where the heterocycle may be unsubstituted or mono- or polysubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio;
R
4
is a pyrazole of the formula II
which is attached in the 4-position and where
R
5
is hydrogen or C
1
-C
6
-alkyl,
R
6
is C
1
-C
6
-alkyl,
or their environmentally compatible salts;
b) an adjuvant comprising
i) a C
1
-C
5
-alkyl C
5
-C
22
-alkanoate,
ii) a C
10
-C
20
-carboxylic acid,
iii) a partial phosphoric ester or a partial sulfuric ester of a monohydroxy-functional polyalkyl ether and
iv) if appropriate an alkyl polyoxyalkylene polyether in a synergistically effective amount.
The herbicidal mixture according to the invention displays a synergistic effect and is selective for those crop plants which are also compatible with the individual compounds.
With respect to the synergistic herbicidal action, particular preference is given to 3-heterocyclyl-substituted benzoyl derivatives of the formula Ib in which
R
1
, R
2
are chlorine, methyl, ethyl, SCH
3
, SOCH
3
, SO
2
CH
3
;
R
3
is hydrogen or methyl;
R
5
is hydrogen, methyl, trifluoromethyl;
R
6
is methyl, ethyl, isopropyl;
X is a heterocycle from the group consisting of: isoxazolyl, 4,5-dihydroisoxazolyl and thiazolyl, where the heterocycle may be unsubstituted or mono- or polysubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio,
or their environmentally compatible salts.
Preferred compounds of the formula Ib are compiled in the table below:
No.
R
1
R
2
R
3
R
5
R
6
X
1.
Cl
SO
2
CH
3
H
CH
3
CH
3
2-thiazolyl
2.
Cl
SO
2
CH
3
H
H
CH
3
2-thiazolyl
3.
Cl
SO
2
CH
3
H
CH
3
CH
3
4,5-dihydroisoxazol-3-yl
4.
Cl
Cl
H
CH
3
CH
3
4,5-dihydroisoxazol-3-yl
5.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydroisoxazol-3-yl
6.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-
methylisoxa-zol-3-yl
7.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5,5-
dimethyl-isoxazol-3-yl
8.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-ethylisoxa-
zol-3-yl
9.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5,5-diethyl-
isoxazol-3-yl
10.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-
chloromethyl-
isoxazol-3-yl
11.
Cl
SCH
3
H
H
CH
3
4,5-dihydroisoxazol-3-yl
12.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-
ethoxyisoxa-zol-3-yl
13.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-
methoxyisoxa-zol-3-yl
14.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydroisoxazol-3-yl
15.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-4,5-
dimethyl-isoxazol-3-yl
16.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-thioethyl-
isoxazol-3-yl
17.
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-trifluoro-
methylisoxazol-3-yl
18.
SCH
3
SCH
3
H
H
CH
3
4,5-dihydroisoxazol-3-yl
19.
Cl
SO
2
CH
3
H
H
C
2
H
5
2-thiazolyl
20.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydroisoxazol-3-yl
21.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-
methylisoxa-zol-3-yl
22.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5,5-
dimethyl-isoxazol-3-yl
23.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-ethylisoxa-
zol-3-yl
24.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5,5-diethyl-
isoxazol-3-yl
25.
Cl
SCH
3
H
H
C
2
H
5
4,5-dihydroisoxazol-3-yl
26.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-
chloromethyl-
isoxazol-3-yl
27.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-
ethoxyisoxa-zol-3-yl
28.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-4,5-
dimethyl-isoxazol-3-yl
29.
CH
3
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydroisoxazol-3-yl
30.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-thioethyl-
isoxazol-3-yl
31.
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-
trifluorome-
thylisoxazol-3-yl
32.
SCH
3
SCH
3
H
H
C
2
H
5
4,5-dihydroisoxazol-3-yl
33.
Cl
SO
2
CH
3
H
H
i-C
4
H
9
4,5-dihydroisoxazol-3-yl
34.
Cl
SO
2
CH
3
H
H
CH
3
3-methylisoxazol-5-yl
35.
Cl
SO
2
CH
3
H
H
C
2
H
5
3-methylisoxazol-5-yl
36.
CH
3
SO
2
CH
3
H
H
C
2
H
5
3-methylisoxazol-5-yl
37.
CH
3
SO
2
CH
3
H
CH
3
CH
3
4,5-dihydroisoxazol-3-yl
38.
CH
3
Cl
H
CH
3
CH
3
4,5-dihydroisoxazol-3-yl
39.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-
methylisoxa-
zol-3-yl
40.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5,5-
dimethyl-isoxazol-3-yl
41.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-ethyl-
isoxazol-3-yl
42.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5,5-ethyl-
isoxazol-3-yl
43.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydroisoxazol-3-yl
44.
CH
3
SO
2
CH
3
H
H
CH
3
4,5-dihydro-4,5-
dimethyl-isoxazol-3-yl
45.
CH
3
Cl
H
H
C
2
H
5
4,5-dihydroisoxazol-3-yl
46.
CH
3
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-
methylisoxa-zol-3-yl
47.
CH
3
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5,5-
dimethyl-isoxazol-3-yl
48.
CH
3
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-ethyl-
isoxazol-3-yl
49.
CH
3
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-4,5-
dimethyl-isoxazol-3-yl
50.
CH
3
SO
2
CH
3
H
H
i-C
4
H
9
4,5-dihydroisoxazol-3-yl
Very particular preference is given to the compounds
4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1H-pyrazole,
4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1H-pyrazole,
4-[2-chloro-3-(3-methylisoxazol-5-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1H-pyrazole and/or their environmentally compatible salts.
Suitable environmentally compatible salts are, for example, salts of alkali metals, alkaline earth metals, ammonia or amines.
Suitable adjuvants b) comprise a mixture of
i) a C
1
-C
5
-alkyl C
5
-C
22
-alkanoate,
ii) a C
10
-C
20
-carboxylic acid,
iii) a partial phosphoric ester or a partial sulfuric ester of a monohydroxy-functional polyalkyl ether and
iv) if appropriate an alkyl polyoxyalkylene polyether.
These adjuvants are described, for example, in U.S. Pat. No. 4,834,908, EP 356 812 and EP 553 074.
Suitable C
1
-C
5
-alkyl C
5
-C
22
-alkanoates (i) are alkyl esters of a carboxylic acid, where the carboxylic acid contains 5-22 carbon atoms and the alkanol used for esterification contains 1-5 carbon atoms, such as, for example, methyl oleate, palmitate, myristate, linolenate, laurate, stearate, pelargonate, ethyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate, n-propyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate, isopropyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate, n-butyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate, isobutyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate, n-pentyl oleate, palmitate, myristate, linolenate, linoleate, laurate, stearate, pelargonate. Preference is given to methyl oleate, methyl palmitate, ethyl oleate and mixtures thereof.
Suitable C
10
-C
20
-carboxylic acids (ii) include saturated and mono- and polyunsaturated carboxylic acids, such as, for example, oleic acid, palmitic acid, myristic acid, linoleic acid, linolenic acid, lauric acid and stearic acid. Preference is given to oleic acid.
Suitable partial phosphoric esters and partial sulfuric esters of a
Berghaus Rainer
Bratz Matthias
Kibler Elmar
Otten Martina
Sievernich Bernd
Clardy S. Mark
Keil & Weinkauf
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