Herbicidal compositions

Details Herbicidal compositions Herbicidal compositions

1999-07-07

2004-06-01

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S116100, C504S117000, C504S128000, C504S133000, C504S134000, C504S135000, C504S132000

Reexamination Certificate

active

06743753

ABSTRACT:

This invention relates to new herbicidal compositions comprising a mixture of an alkoxypyrimidyloxybenzoic acid derivative and at least one partner herbicide. Additionally, this invention relates to a method of controlling weeds with the new herbicidal compositions comprising a mixture of an alkoxypyrimidyloxybenzoic acid derivative and at least one partner herbicide.
Pyribenzoxim, which is benzophenone O-{2,6-bis[(4,6-dimethoxypyrimidyl) oxy]benzoyl}oxime is known as a herbicide, see for example European Patent No. 658549.
Bispyribac is also known as sodium 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate.
An object of the present invention is to provide a herbicidally effective mixture for increasing the efficacy of alkoxypyrimidyloxybenzoic acid derivatives, especially pyribenzoxims.
A further object of the present invention is to extend the spectrum of post-emergence herbicidal activity without loss of crop selectivity for an alkoxypyrimidyloxybenzoic acid derivative in combination with a partner herbicide, for example pyribenzoxim in combination with fenoxaprop-P. The term “combination” according to the invention as used in this specification refers to the “combination” of an alkoxypyrimidyloxybenzoic acid derivative and a partner herbicide.
Another object of the present invention is the selectivity of the combination of the invention.
A high level of control of many weeds is desirable to prevent:
1) yield loss, through competition from weeds and/or difficulties with harvest;
2) crop contamination leading to storage and cleaning difficulties; and
3) unacceptable weed seed return to the soil.
The present invention seeks to provide a herbicidal composition which allows lower dose rates of partner herbicides to be applied to the environment without reducing (and preferably increasing) the level of weed control.
A further object of the present invention is to provide a herbicidal composition which provides residual activity against weeds germinating after application, e.g., pyribenzoxim in combination with oxadiargyl.
The objects of the invention can be achieved in whole or part by the present invention.
The present invention provides a composition comprising:
(a) an alkoxypyrimidyloxybenzoic acid derivative of formula (I):
wherein X is a hydrogen atom or a group (C
6
H
5
)
2
C═N—, and agriculturally acceptable salts thereof, for example alkali or alkaline earth metal salts and
(b) a partner herbicide;
the amounts of a and b in combination being herbicidally effective, in association with an agriculturally acceptable diluent or carrier.
The alkoxypyrimidyloxybenzoic acid derivatives used in the invention are advantageously pyribenzoxim or bispyribac, preferably pyribenzoxim. Bispyribac is the compound of formula (I) wherein X is Na. Pyribenzoxim is the compound of formula (I) wherein X is (C
6
H
5
)
2
C═N—.
Partner herbicides are preferably chosen from sulfonylureas, anilides, 2,6-dinitroanilines, carfentrazone, aryloxyphenoxy propionic acids, oxadiazoles, pyrimidyl salicylate, sulfamoylureas, thiocarbamates, hydroxybenzonitriles and pyrazoles.
Advantageous possible partner herbicides for use in the present invention include:
pendimethalin, which is [N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine];
bentazone, which is 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide;
butachlor, which is N-butoxymethyl-2-chloro-2′,6′-diethylacetanilide;
pretilachlor, which is 2-chloro-2′,6′-diethyl-N-(2-propoxyethyl)acetanilide;
oxadiargyl, which is 5 tert-butyl-3-[2,4-dichloro-5-(prop-2-ynyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one;
diflufenican, which is [2′-4′-difluoro-2-(&agr;,&agr;,&agr;-trifluoro-m-tolyloxy) nicotinanilide;
bromoxynil, which is 3,5-dibromo-4-hydroxybenzonitrile;
ioxynil, which is 4-hydroxy-3,5-di-iodobenzonitrile;
propanil, which is 3′,4′-dichloropropionanilide;
carfentrazone, which is ethyl 2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionate;
fenoxaprop, which is [(±)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy) phenoxy]propionic acid;
fenoxaprop-P, which is [(R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy) phenoxy]propionic acid;
cyhalofop, which is butyl(R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionate;
cyclosulfamuron, which is 1-[2-(cyclopropylcarbonyl)anilinosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea;
pyributicarb, which is O-3-tert-butylphenyl 6-methoxy-2-pyridyl(methyl)thiocarbamate;
benzofenap, which is 2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4-′methylacetophenone;
cinosulfuron, which is 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy) phenylsulfonyl]urea;
bensulfuron, which is &agr;-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluic acid;
pyrazosulfuron, which is 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylic acid;
imazosulfuron, which is 1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea; and
azimsulfuron, which is 1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2-H-tetrazol-5-yl)-pyrazol-5-ylsulfonyl]urea.
The preferred partner herbicides are chosen from cyhalofop, fenoxaprop, fenoxaprop-P, bensulfuron, pyrazosulfuron, imazosulfuron, bentazone, benzofenap and oxadiargyl.
The most preferred mixtures are those comprising pyribenzoxim in combination with aryloxyphenoxy propionic acids or sulfonylureas or oxadiargyl. Preferred aryloxyphenoxy propionic acid herbicides are cyhalofop, fenoxaprop and fenoxaprop-P. Preferred sulfonylureas are bensulfuron or pyrazosulfuron or imazosulfuron.
According to another feature of the present invention, there is provided a method for controlling the growth of weeds, i.e. undesired vegetation, at a locus which comprises applying to the locus a herbicidally effective amount of a mixture comprising an alkoxypyrimidyloxybenzoic acid derivative of formula (I) and a partner herbicide as defined hereinabove.
The term ‘post-emergence application’ refers to application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil. The term ‘foliar activity’ refers to herbicidal activity produced by application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil. The term ‘residual activity’ refers to herbicidal activity produced by application to the soil in which weed seeds or seedlings are present before emergence of the weeds above the surface of the soil, whereby seedlings present at the time of application or which germinate subsequent to application from seeds present in the soil, are controlled.
Preferably, compositions of the present invention are applied to an area used, or to be used, for the growing of a crop, for example cereal crops, rice and wheat. The method of the invention is preferably performed where the crop to be protected is rice.
Weeds that may be controlled by this method include;
Echinochloa crus
-
galli, Leptochloa chinensis, Ischaemum rugosum, Sphenoclea zeylanica, Cyperus difformis, Cyperus iria, Cyperus seotinus
, Fimbristylis,
Monochoria vaginalis, Echinochloa colonum
, Sphenoclea, Eleocharis,
Marsilea, Saggitaria, Scirpus maritimus, Scirpus mucronatus
and Sesbania.
The amounts of alkoxypyrimidyloxybenzoic acid derivative of formula (I) and partner herbicide applied depend on many factors, including, but not limited to the weed species to be controlled, the crop present, the timing of the application and the climatic and edaphic conditions. When applied to a crop-growing area, the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop. In general, taking these factors into account, application rates from 0.005 kg to 0.2 kg preferably 0.005 kg to 0.1 kg of alkoxypyrimidyloxybenzoic acid derivative of formula (I) and 0.001 kg to 4 kg of partner herbicide per hectar

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