Herbicidal mixture containing a 3-heterocyclyl-substituted...

Details Herbicidal mixture containing a 3-heterocyclyl-substituted... Herbicidal mixture containing a 3-heterocyclyl-substituted...

2000-12-05

2002-11-12

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S269000, C504S271000

Reexamination Certificate

active

06479437

ABSTRACT:

This application is a 371 of PCT/EP99/03676 filed May 27, 1999.
The present invention relates to a synergistically acting herbicidal mixture of a 3-heterocyclyl-substituted benzoyl derivative, a nitrogenous fertilizer and an adjuvant.
3-Heterocyclyl-substituted benzoyl derivatives are known and are described, for example, in WO 96/26206, WO 97/41116, WO 97/41117 and WO 97/41118.
Herbicidal compositions of substituted cyclohexanediones and nitrogen fertilizers are disclosed in EP-B-0584 227.
It is an object of the present invention to provide a herbicidal mixture which comprises 3-heterocyclyl-substituted benzoyl derivatives and whose herbicidal action exceeds the action of the pure active ingredient.
We have found that this object is achieved by a herbicidal mixture which comprises
a) a herbicidally active amount of a 3-heterocyclyl-substituted benzoyl derivative of the formula I
 in which the variables have the following meanings:
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 amongst the group consisting of isoxazolyl, 4,5-dihydroisoxazolyl and thiazolyl, it being possible for the heterocycle to be optionally monosubstituted 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 linked 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) a nitrogenous fertilizer in a synergistically effective amount and
c) an adjuvant in a synergistically effective amount.
The herbicidal mixture according to the invention exhibits a synergistic effect and is selective for those crop plants which also tolerate the individual compounds themselves.
3-Heterocyclyl-substituted benzoyl derivatives of the formula Ib which are especially preferred with a view to the synergistic herbicidal action are those in which
R
1
, R
2
are chlorine, methyl, ethyl, SCH
3
, SOCH
3
, SO
2
CH
3
;
R
3
is hydrogen and methyl;
R
5
is hydrogen, methyl, trifluoromethyl;
R
6
is methyl, ethyl, isopropyl;
X is a heterocycle from amongst the group: isoxazolyl, 4,5-dihydroisoxazolyl and thiazolyl, it being possible for the heterocycle to be optionally monosubstituted 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 which follows:
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-ethyl-
isoxazol-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-chloro-
methylisoxazol-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-ethoxy-
isoxazol-3-yl
13
Cl
SO
2
CH
3
H
H
CH
3
4,5-dihydro-5-methoxy-
isoxazol-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-methyl-
isoxazol-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-ethyl-
isoxazol-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-chloro-
methylisoxazol-3-yl
27
Cl
SO
2
CH
3
H
H
C
2
H
5
4,5-dihydro-5-ethoxy-
isoxazol-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-trifluoro-
methylisoxazol-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-methyl-
isoxazol-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-methyl-
isoxazol-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 especially preferred are 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,
or their environmentally compatible salts.
Suitable environmentally compatible salts are salts of, for example, alkali metals, alkaline earth metals, ammonia or amines.
Suitable nitrogenous fertilizers b) are ammonia and ammonium salts, urea, thiourea and mixtures of these.
Examples of suitable fertilizers are aqueous ammonia solution, ammonium nitrate, ammonium sulfate, ammonium hydrogen sulfate, ammonium chloride, ammonium acetate, ammonium formate, ammonium oxalate, ammonium carbonate, ammonium hydrogen carbonate, ammonium nitrate, ammonium thiosulfate, ammonium phosphate, ammonium hydrogen diphosphate, ammonium dihydrogen monophosphate, ammonium sodium hydrogen phosphate, ammonium thiocyanate, urea and thiourea, and mixtures of these, and also ammonium nitrate/urea solutions (UAN or AHL solutions).
Preferred nitrogenous fertilizers are urea, ammonium nitrate, ammonium nitrate/urea solutions, ammonium sulfate, ammonium phosphate, ammonium hydrogen diphosphate, ammonium dihydrogen monophosphate and ammonium sodium hydrogen phosphate.
Very especially preferred are urea, ammonium nitrate and ammonium nitrate/urea solutions. The ammonium nitrate/urea solutions preferably have a total nitrogen content of 28-33% (w/w) and are commercially available from BASF, for example under the brand name Ensol® 28.
Suitable adjuvants c) are vegetable oils which can be partially hydrogenated and hydrogenated, modified vegetable oils, mineral oils, alcohol alkoxylates, alcohol ethoxylates, alkylated EO/PO block copolymers, alkylphenol ethoxylates, polyols, EO/PO block copolymers, organosilicon compounds, alkylglycosides, alkyl polyglycosides, alkyl sulfates, sulfated alcohol alkoxylates, alkylarylsulfonates, alkylsulfonates, dialkylsulfosuccinates, phosphated alcohol alkoxylates, fatty amine alkoxylates, esters, carboxylates, ester ethoxylates, dialkyl adipates, dicarboxylic acid derivatives, such as alkenylsuccinic anhydride condensates with polyalkylene oxides or polyhydroxyamines; dialkyl phthalates, ethoxylated sorbit

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