Herbicidal compositions

Details Herbicidal compositions Herbicidal compositions

1999-03-09

2001-04-10

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S139000, C504S141000

Reexamination Certificate

active

06214770

ABSTRACT:

CROSS-REFERENCE TO PRIORITY APPLICATION
This application claims priority under 35 U.S.C. §119 of United Kingdom Patent Application No. 98 04986.9, filed Mar. 9, 1998, expressly incorporated by reference herein in its entirety and relied upon.
This invention relates to new herbicidal compositions comprising a mixture of 4-benzoylisoxazoles or 2-cyano-1,3-diones and herbicidal urea compounds. It also relates to the use of the mixture per se and to a method of controlling weeds.
Herbicidal 4-benzoylisoxazoles are disclosed in the literature, for example see European Patent Publication Nos. 0418175, 0487357, 0527036 and 0560482. Herbicidal 2-cyano-1,3-dione derivatives are known from EP 0213892, EP 0496630, EP 0496631 and EP 0560482. The first commercially available 4-benzoylisoxazole is isoxaflutole [5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)benzoylisoxazole]. Urea herbicides are well known in the literature. Examples of such herbicides include as fenuron, fluometuron, monuron and monolinuron, chlortoluron, isoproturon, diuron, linuron, neburon, methabenzthiazuron and tebuthiuron, all of which are described in the Pesticide Manual 10th edition (British Crop Protection Council).
The present invention provides a method for controlling the growth of weeds (i.e. undesired vegetation) at a locus which comprises applying to the locus an effective amount of
(a) a urea herbicide, preferably a compound of the general formula (I):
R
11
N(R
12
)CON(R
13
)R
14
  (I)
wherein R
11
represents an optionally substituted cyclic hydrocarbyl (which is preferably aromatic e.g. phenyl) or aromatic heterocyclyl (e.g. thiadiazol-2-yl) group, R
12
represents hydrogen or straight or branched chain alkyl containing from 1 to 6 carbon atoms, R
13
represents straight or branched chain alkyl containing from 1 to 6 carbon atoms or an optionally substituted cyclic hydrocarbyl (e.g. 2-methylcyclohexyl) group and R
14
represents hydrogen or straight or branched chain alkyl or alkoxy containing from 1 to 6 carbon atoms; and
(b) a 4-benzoylisoxazole herbicide or a 2-cyano-1,3-dione herbicide, an enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof;
which are herbicidally effective in combination. For this purpose, the urea herbicide and (b) are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers and/or surface-active agents suitable for use in herbicidal compositions), for example as hereinafter described.
Preferred compounds of general formula I are those wherein R
12
represents the hydrogen atom or the methyl group and R
13
represents the methyl group.
Preferred compounds of general formula I are those wherein R
12
represents the hydrogen atom, R
13
represents a phenyl, 3-trifluoromethylphenyl or 4-chlorophenyl group and R
14
represents the methyl group;
or (b) R
11
represents a 4-chlorophenyl group and R
14
represents the methoxy group, which are known respectively as fenuron, fluometuron, monuron and monolinuron, and more especially compounds of general formula I wherein R
12
represents the hydrogen atom and R
13
represents the methyl group and (c) R
11
represents a 3-chloro-4-methylphenyl or 4-isopropylphenyl group and R
14
represents the methyl group;
or (d) R
11
represents the 3,4-dichlorophenyl group and R
14
represents methyl, methoxy or butyl; or (e) R
11
represents the benzothiazol-2-yl group, R
12
represents methyl and R
13
represents methyl and R
14
represents hydrogen or (f) R
11
represents 5-t-butyl-thiadiazol-2-yl; R
12
and R
13
represent methyl and R
14
represents hydrogen; which are known respectively as chlortoluron, isoproturon, diuron, linuron, neburon, methabenzthiazuron and tebuthiuron.
Preferably (a) is tebuthiuron.
Preferably (b) is a 4-benzoylisoxazole herbicide. Preferably the 4-benzoylisoxazole has the formula (II):
wherein
R is hydrogen or —CO
2
R
3
;
R
1
is C
1-4
alkyl or C
3-6
cycloalkyl optionally substituted by C
1-6
alkyl;
R
2
is selected from halogen, nitro, cyano, —(CR
4
R
5
)
q
S(O)
p
R
6
, —S(O)
p
R
6
, —N(R
7
)SO
2
R
6
, C
1-6
alkoxy, —OSO
2
R
6
, C
1-4
haloalkoxy, C
1-4
alkyl and C
1-4
haloalkyl, wherein R
4
, R
5
, R
6
, R
7
, p and q are as defined below;
or two groups R
2
, on adjacent carbon atoms of the phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 membered saturated or unsaturated heterocyclic ring containing up to three ring heteroatoms selected from nitrogen, oxygen and sulfur, which ring may be optionally substituted by one or more groups selected from halogen, nitro, —S(O)
p
R
6
, C
1-4
alkyl, C
1-4
alkoxy, C
1-4
haloalkyl and C
1-4
haloalkoxy, wherein R
6
and p are as defined below, it being understood that a sulphur atom, where present in the ring, may be in the form of a group —SO— or —SO
2
—;
n is an integer from one to five; p is zero, one or two;
q is one or two; where q is two the groups (CR
4
R
5
) may be the same or different;
R
3
is C
1-4
alkyl;
R
4
and R
5
are independently hydrogen or C
1-4
alkyl;
R
6
is C
1-4
alkyl, or phenyl or benzyl, each of phenyl and benzyl optionally bearing from one to five substituents which may be the same or different selected from the group consisting of halogen, C
1-4
alkyl, C
1-4
alkoxy, C
1-4
haloalkyl, C
1-4
haloalkoxy, nitro and —S(O)
p
CH
3
, wherein p is as defined above;
and R
7
is hydrogen or C
1-6
alkyl.
In this description the term “agriculturally acceptable salts” means salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable salts with bases include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.
It will be understood that in certain cases the groups R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
may give rise to stereoisomers and geometric isomers. All such forms are embraced by the present invention.
Throughout this description the terms “alkyl” and “alkoxy” refer to straight or branched chains. The terms “haloalkyl” and “haloalkoxy” refer to alkyl and alkoxy respectively, each substituted by at least one halogen. The term “halogen” refers to fluorine, chlorine, bromine and iodine.
In formula (II) above, compounds in which n is three and the groups (R
2
)
n
occupy the 2,3 and 4-positions of the benzoyl ring; or in which n is two and the groups (R
2
)
n
occupy the 2 and 4-positions of the benzoyl ring are preferred.
In formula (II) above, R
2
is preferably selected from halogen (preferably chlorine or bromine), —S(O)
p
Me and trifluoromethyl.
In formula (II) above, preferably one of the groups R
2
is —S(O)
p
Me.
Compounds of formula (II) above in which R is hydrogen are also preferred.
The compounds of formula (II) of particular interest include the following: 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)benzoylisoxazole (isoxaflutole); 5-cyclopropyl-4-(4-methylsulphonyl-2-trifluoromethyl)benzoylisoxazole; 4-(2-chloro-4-methylsulphonyl)benzoyl-5-cyclopropylisoxazole; 4-(4-chloro-2-methylsulphonyl)benzoyl-5-cyclopropylisoxazole; 4-(4-bromo-2-methylsulphonyl)benzoyl-5-cyclopropylisoxazole; and ethyl 5-cyclopropyl-4-(2-methylsulphonyl4-trifluoromethyl)benzoylisoxazole-3-carboxylate.
When component (b) is a 2-cyano-1,3-dione derivative, it is generally a compound of formula (III):
wherein R
30
is C
1-4
alkyl or C
3-6
cycloalkyl optionally substituted by C
1-6
alkyl;
R
31
is selected from halogen, nitro, cyano, —S(O)
r
R
32
, —(CR
33
R
34
)
v
S(O)
r
R
32
, —N(R
35
)SO
2
R
32
, C
1-6
alkoxy, —OSO
2
R
32
, C
1-4
haloalkoxy, C
1-4
alkyl and C
1-4
haloalkyl;
or two groups R
31
, on adjacent carbon atoms of the phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 membered saturated or unsaturated heterocyclic ring containing up to three ring heteroatoms selected

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