Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2000-06-15
2002-01-22
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S363000, C504S364000
Reexamination Certificate
active
06340655
ABSTRACT:
BACKGROUND OF THE INVENTION
Dinitroaniline herbicides such as pendimethalin and trifluralin, and oxyacetamide herbicides such as fluthiamid are known in the art. Combination treatments using these types of herbicides are disclosed in U.S. Pat. Nos. 4,968,342 and 5,759,955; and in German Application No. 19720367. However, emulsifiable concentrate compositions comprising dinitroaniline and oxyacetamide herbicides are not known in the art.
U.S. Pat. No. 3,898,075 relates to stabilized liquid compositions containing m-biscarbamates and organic acids. U.S. Pat. No. 2,954,396 describes a method for stabilizing carbamate esters with certain hydrolysis inhibitors. However, neither U.S. Pat. No. 3,898,075 nor U.S. Pat. No. 2,954,396 describe any method for the stabilization of oxyacetamide herbicides.
It is therefore an object of the present invention to provide stable emulsifiable concentrate compositions of dinitroaniline herbicides and oxyacetamide herbicides.
Other objects and advantages of the present invention will be apparent to those skilled in the art from the description below and the appended claims.
SUMMARY OF THE INVENTION
The present invention relates to a herbicidal emulsifiable concentrate composition comprising, on a weight to weight basis, about 15% to 40% of a dinitroaniline herbicide, about 1% to 10% of an oxyacetamide herbicide, about 0.01% to 1% phosphoric acid, up to about 30% of an emulsifier or mixture of emulsifiers, up to about 1% of an antifoaming agent, and an organic solvent or mixture of organic solvents.
DETAILED DESCRIPTION OF THE INVENTION
The herbicidal emulsifiable concentrate compositions of this invention comprise, on a weight to weight basis, about 15% to 40% of a dinitroaniline herbicide, about 1% to 10% of an oxyacetamide herbicide, about 0.01% to 1% phosphoric acid, up to about 30% of an emulsifier or mixture of emulsifiers, up to about 1% of an antifoaming agent, and an organic solvent or mixture of organic solvents.
Preferred herbicidal emulsifiable concentrate compositions of the present invention are those comprising, on a weight to weight basis, about 15% to 40% of a dinitroaniline herbicide, about 1% to 10% of an oxyacetamide herbicide, about 0.01% to 1% phosphoric acid, about 2% to 10% of an alkylarylsufonate, about 0.5% to 5% of a polyalkylene glycol ether, about 1% to 5% of an ethoxylated fatty alcohol, up to about 1% of an antifoaming agent, and an aromatic hydrocarbon solvent having a distillation range of about 135° C. to 305° C.
More preferred emulsifiable concentrate compositions of this invention are those comprising, on a weight to weight basis, about 25% to 35% pendimethalin, about 4% to 8% fluthiamid, about 0.05% to 0.2% phosphoric acid, about 2% to 6% of a dodecylbenzenesulfonate, about 1% to 3% of an alkyl capped ethylene oxide/propylene oxide block copolymer, about 1% to 5% of an ethoxylated C
10
-C
16
fatty alcohol having about 8 to 12 moles of ethylene oxide per mole, up to about 1% of an antifoaming agent, and an aromatic hydrocarbon solvent having a distillation range of about 135° to 305° C.
Phosphoric acid is an especially important element of the present compositions because it has been found that oxyacetamide herbicides are more stable in the phosphoric acid containing emulsifiable concentrate compositions of the present invention than in corresponding emulsifiable concentrate compositions which do not contain phosphoric acid. In a preferred embodiment of the present invention, the ratio of the oxyacetamide herbicide to the phosphoric acid, on a weight basis, is preferably about 30:1 to 100:1, and more preferably, is about 40:1 to 70:1.
Dinitroaniline herbicides suitable for use in the compositions of this invention have the structural formula I
wherein
R is hydrogen, C
2
-C
4
alkyl or chloroethyl;
R
1
is C
2
-C
5
alkyl, chloroethyl, 2-methallyl or cyclopropylmethyl;
R
2
is hydrogen, methyl or amino; and
R
3
is trifluoromethyl, C
1
-C
3
alkyl, SO
2
NH
2
or SO
2
CH
3
.
Preferred dinitroaniline herbicides for use in this invention include pendimethalin and trifluralin with pendimethalin being more preferred.
Oxyacetamide herbicides suitable for use in the compositions of the present invention are those described in U.S. Pat. Nos. 4,408,055; 4,509,971; 4,540,430; 4,549,899; 4,585,471; 4,645,525; 4,756,741; 4,784,682; 4,788,291; 4,833,243; 4,968,342; 4,988,380; 5,090,991 and 5,234,896; EP Application Nos. 300344-A and 500934-A1; and WO 97/08160.
Preferred oxyacetamide herbicides for use in the compositions of this invention have the structural formula II
wherein
R
4
is hydrogen, F, Cl, Br, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylsulfonyl or C
1
-C
4
haloalkylsulfonyl;
R
5
is hydrogen or C
1
-C
6
alkyl; and
R
6
is phenyl optionally substituted with any combination
of from one to three F, Cl, Br, CN, NO
2
, C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
More preferred oxyacetamide herbicides for use in the emulsifiable concentrate compositions of this invention are those wherein
R
4
is C
1
-C
4
haloalkyl;
R
5
is C
1
-C
4
alkyl; and
R
6
is phenyl optionally substituted with any combination
of one or two F, Cl or C
1
-C
4
alkyl groups.
Most preferred oxyacetamide herbicides are those of formula II wherein
R
4
is CF
3
, CHF
2
or CFCl
2
;
R
5
is isopropyl; and
R
6
is selected from the group consisting of phenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl and 3,4-dimethylphenyl.
An oxyacetamide herbicide which is especially suitable for use in the compositions of this invention is 4′-fluoro-N-isopropyl-2-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}acetanilide (fluthiamid).
Emulsifiers suitable for use in the compositions of the present invention include, but are not limited to, alkylarylsulfonates including C
8
-C
18
alkylbenzenesulfonates such as calcium dodecylbenzenesulfonate; polyalkylene glycol ethers including alkyl capped ethylene oxide/propylene oxide block copolymers such as butyl capped ethylene oxide/propylene oxide block copolymers; and ethoxylated fatty alcohols including ethoxylated C
10-C
16
fatty alcohols having about 8 to 12 moles of ethylene oxide per mole; and mixtures thereof. Preferred emulsifiers include the alkali metal or alkaline earth metal salts of dodecylbenzene sulfonic acid, such as calcium dodecylbenzenesulfonate including SOPROPHOR® 70 a 60% calcium dodecylbenzene sulfonate solution in isobutanol commercially available from Rhodia, Milan, Italy; butyl capped ethylene oxide/propylene oxide block copolymers including WITCONOL® NS 500K a butyl capped ethylene oxide/propylene oxide block copolymer commerically available from Witco SA, Saint-Pierre Les Elbeuf, France; and ethoxylated C
10
-C
16
fatty alcohols having about 8 to 12 moles of ethylene oxide per mole including RHODASURF® 870 a C
13
ethoxylated fatty alcohol containing 10 moles of ethylene oxide per mole commercially available from Rhodia, Milan, Italy; and mixtures thereof.
Organic solvents suitable for use in the compositions of this invention include aromatic hydrocarbon solvents such as toluene, xylenes, polynuclear aromatic hydrocarbons such as naphthalenes and alkylnaphthalenes and mixtures thereof, many of which are available from the fractionation of crude oil and in general have distillation ranges in the temperature range of about 135° C. to 305° C., with those having a distillation range of from about 183° C. to 290° C. being most preferred. These solvents are commercially available under a variety of tradenames, e.g. SOLVESSO®200 and AROMATIC®200 both commercially available from Exxon, Fareham, Hants, United Kingdom.
Antifoaming agents suitable for use in the compositions of the present invention include conventional antifoaming agents, with silicone based antifoaming agents such as those sold under the SILCOLAPSE® tradename commercially available from Rhodia, Lyon, France being preferred. In a preferred embodiment of this inventio
American Cyanamid Co.
Clardy S. Mark
Maurer Barbara V.
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