CA1131036A - Herbicidal treatments and formulations - Google Patents
Herbicidal treatments and formulationsInfo
- Publication number
- CA1131036A CA1131036A CA342,403A CA342403A CA1131036A CA 1131036 A CA1131036 A CA 1131036A CA 342403 A CA342403 A CA 342403A CA 1131036 A CA1131036 A CA 1131036A
- Authority
- CA
- Canada
- Prior art keywords
- bifenox
- herbicide
- salt
- ester
- rate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
HERBICIDAL TREATMENTS AND FORMULATIONS
ABSTRACT OF THE INVENTION
Disclosed is a method of controlling weeds in a cereal crop locus, which method comprises applying to said locus, post-emergence the crop, bifenox, being a compound of formula I, I
and one or more further active ingredients selected from (1) a benzoic acid herbicide which is dicamba or 2,3,6-TBA or a salt or ester therof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide which is DNOC, dinoteb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which is ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof, and herbicidal formulations for use in such method.
ABSTRACT OF THE INVENTION
Disclosed is a method of controlling weeds in a cereal crop locus, which method comprises applying to said locus, post-emergence the crop, bifenox, being a compound of formula I, I
and one or more further active ingredients selected from (1) a benzoic acid herbicide which is dicamba or 2,3,6-TBA or a salt or ester therof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide which is DNOC, dinoteb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which is ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof, and herbicidal formulations for use in such method.
Description
1:133L~3~
HERBICIDA~ 3 71/~ D F~RM~ ONS
The inventio~ relate.s to a method of controlling weeds in c2real crops and to herbicidal fo~mulations useful inter alia in such method.
In order to control a broad ranye of weeds in cro~s, such as cereal crops~ it is o~ten necessary to employ more than one herbicide.
Despite the use of such mixtures, weeds ~re still resistant to herbicide traatment, causing damage to both winter and spring cereal crops such as, for example, wheatr barley, oats and rye.
It ha~ now been found that speci~ic combinations of herbicides not only give a broad spectrum of control but are also unexpectedly effective against ~eeds, especially broadleaf weedæ, in cereal crops.
Accordingly, the invention provides a method of controlling weed9, especially broadleaf w~eds, in a cereal crop loous, which method comprise~ applying to ~aid locus, post emergence the crop, bifenox, being - a compound of ~ormula I, ~2 ~ D ~ ~ - Cl and one or more further active ingredient~ selec~ed from (l) a benzoic acid herbicide which is dioamba or 2,3,6-TBA or a salt or ester thereof,
HERBICIDA~ 3 71/~ D F~RM~ ONS
The inventio~ relate.s to a method of controlling weeds in c2real crops and to herbicidal fo~mulations useful inter alia in such method.
In order to control a broad ranye of weeds in cro~s, such as cereal crops~ it is o~ten necessary to employ more than one herbicide.
Despite the use of such mixtures, weeds ~re still resistant to herbicide traatment, causing damage to both winter and spring cereal crops such as, for example, wheatr barley, oats and rye.
It ha~ now been found that speci~ic combinations of herbicides not only give a broad spectrum of control but are also unexpectedly effective against ~eeds, especially broadleaf weedæ, in cereal crops.
Accordingly, the invention provides a method of controlling weed9, especially broadleaf w~eds, in a cereal crop loous, which method comprise~ applying to ~aid locus, post emergence the crop, bifenox, being - a compound of ~ormula I, ~2 ~ D ~ ~ - Cl and one or more further active ingredient~ selec~ed from (l) a benzoic acid herbicide which is dioamba or 2,3,6-TBA or a salt or ester thereof,
(2) a phenoxy a~id herbicide which is dichlorprop or 2,4-DB or a salt ox ester thereo~, (3) a dinitrophenol herbicide which i~ DNOC/ dinoterb or dinoseb or a salt or estex thereof~ (4) a ben~onitrile herbicide ~hich ~ is ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereo~, (6) bentazone, and (7) 3,6-DCP or a salt or ester thereof.
3~36 It will be appreciated that more than one of the acti~e ingredients (1) to (7) may be employed in the method of the invention and, indeed, that further or additional herbicidally active compounds may be employed alongside such ingredients (1) to (7). Where the active ingredient is acidic or phenolic, derivatives such as salts and esters may be employed, provided, of course, that they are non-phytotoxic to the cropl that is to say not substantially more phytotoxic than the Eree acid or phenoI. The nature of such salts and esters is well-known to those skilled in the art.
The preparation o~ bifenox, methyl 5~(2,4-dichlorophenoxy)-2-nitrobenæoate, is described in United Ringdom Patent 1,232,368 and its use as a herbicide in Proc. N.E. Weed Sci Con 1973, 27, 31.
Similarly, the benzoic acid herbicide dicamba, which is 3,6-dichloro~2-me~hoxybenzoic acid, is disclosed in U.S. Patent 3,013,054, and 2,3,6-TBA, which is 2,3,6-trichlorobenzoic acid, in U.S.
Patents 2,848,470 and 3,0~1,162. The phenoxy acid herbicides are a well-knGwn group of compounds and have been widely available for some considerable time. Dichlorprop is a common name for 2-(2,4-dichlorophenoxy) propionic acid, otherwise known as 2,4-DP; 2,4-DB
is the common name for 4-(2,4-dichlorophenoxy) butyric acid. The.
dinitrophenol herbicide, DNOC (chemical name 2-methyl-4,6-dinitrophenol3 was introduced under the protection of British Patent 425,295; dinoseb is the common name for 2-sec-butyl-4,6-dinitrophenol, disclosed in U.S.
Patent 2,192,197; and dinoterb, 2-tert-butyl-4,6-dinitrophenol is disclosed in, for example, British Patent 1,126,658. The benzonitrile herbicides ioxynil (4-hydro~y-3,5-dl-iodoben2Onitrile) and bromoxynil (3,5-dibromo-4-hydroxybenzonltrile) are both disclosed in, for example, British Patent 977,755. Benazolin, having the chemical structure
The preparation o~ bifenox, methyl 5~(2,4-dichlorophenoxy)-2-nitrobenæoate, is described in United Ringdom Patent 1,232,368 and its use as a herbicide in Proc. N.E. Weed Sci Con 1973, 27, 31.
Similarly, the benzoic acid herbicide dicamba, which is 3,6-dichloro~2-me~hoxybenzoic acid, is disclosed in U.S. Patent 3,013,054, and 2,3,6-TBA, which is 2,3,6-trichlorobenzoic acid, in U.S.
Patents 2,848,470 and 3,0~1,162. The phenoxy acid herbicides are a well-knGwn group of compounds and have been widely available for some considerable time. Dichlorprop is a common name for 2-(2,4-dichlorophenoxy) propionic acid, otherwise known as 2,4-DP; 2,4-DB
is the common name for 4-(2,4-dichlorophenoxy) butyric acid. The.
dinitrophenol herbicide, DNOC (chemical name 2-methyl-4,6-dinitrophenol3 was introduced under the protection of British Patent 425,295; dinoseb is the common name for 2-sec-butyl-4,6-dinitrophenol, disclosed in U.S.
Patent 2,192,197; and dinoterb, 2-tert-butyl-4,6-dinitrophenol is disclosed in, for example, British Patent 1,126,658. The benzonitrile herbicides ioxynil (4-hydro~y-3,5-dl-iodoben2Onitrile) and bromoxynil (3,5-dibromo-4-hydroxybenzonltrile) are both disclosed in, for example, British Patent 977,755. Benazolin, having the chemical structure
4-chloro-2-oxo~3-benzothiazolineacetic acid, is disclosed in aritish Patent 862,226 and bentazone, which is the common name ~or 3-isopropyl-(lH)-benzo-2,1,3-thiadiazin-4-one 2,2-dioxide, is described in U.S. Patent 3,708,277. 3,6-DCP, which is 3,6-dichloropicolinic acid is disclosed in U.S. Patent 3,317,549.
~3~3~
~3-The cereal crop can be, for example, wheat, barley, oats or rye, and the method of the invention finds its greatest potential in the treatment of wheat and barley, particularly winter wheat and spring and winter barley. Crop sensitivity and also the severity of the weed problem determine the amount of active ingredients applied. In general, however, the bi~enox is applied at a rate of 0.25 to 3.0 kilogram per hectare, preferably from 0.5 ~o 1.5 kilogram per hectare and particularly from 0.5 to 0.75 kilogram per hectare.
Set out below are the preferred application rates for the further active ingredients (1) to ~7). Wh@re a component is derived from an acid or phenol, the quantities are based on the free acid or phenol equivalent.
Thu , where a benzoic acid herbicide, which is dicamba or 2,3,6-TBA, is e~ployed, such is preferably applied at a rate of ~rom 0.05 to 0.2 kilogram per hectare, the weight ratio cf the bifenox to the benzoic acid herbicide suitably being in the ratio of 60:1 to 1:1, preferably 30:1 to 4:1. The benzoic acid herbioide may be employed in ~he fcrm of a salt thereof, especially an alkali metal salt such as a sodium or potassium salt, or in the form of an ester $hereof, e.g. a Cl-C8 alkyl ester.
.
~here a phenoxy acid herbicide, which i5 dichloroprop or 2,4-DB, Z5 i~ employed, such is preferably applied at a rate o~ 0.1 ~o 3.5 kilogram per hectare, the weight ratio of the bifenox to the phenoxy acid herbicide suitably being in the ratio of 30:1 to 1:15, especially from 8:1 to 1:6. In a particularly preferred embodiment, the bifenox is applied at a rate of 0.5 to 0.75 kilogram per hectare, the phenoxy acid herbicide at a rate of 1.5 to 3.0 kilogram per hectare. The phenoxy acid herbicide is suitably employed in the ~orm of a salt thereof, for example as an alkali metal salt, especially the sodium or potassium salt, or as an amine or ammonium salt. AS examples of ester forms of the phenoxy acid herbicide may be given those containing from 1 to 8 carbon atoms in the ester grouping, for example the ethyl, isopropyl and butyl esters.
~3~ 6 Where a dinitrophenol herbicide, which is DNOC, dinoterb or dinoseb is employed, such is preferably applied at a ra~e of from 0.5 to
~3~3~
~3-The cereal crop can be, for example, wheat, barley, oats or rye, and the method of the invention finds its greatest potential in the treatment of wheat and barley, particularly winter wheat and spring and winter barley. Crop sensitivity and also the severity of the weed problem determine the amount of active ingredients applied. In general, however, the bi~enox is applied at a rate of 0.25 to 3.0 kilogram per hectare, preferably from 0.5 ~o 1.5 kilogram per hectare and particularly from 0.5 to 0.75 kilogram per hectare.
Set out below are the preferred application rates for the further active ingredients (1) to ~7). Wh@re a component is derived from an acid or phenol, the quantities are based on the free acid or phenol equivalent.
Thu , where a benzoic acid herbicide, which is dicamba or 2,3,6-TBA, is e~ployed, such is preferably applied at a rate of ~rom 0.05 to 0.2 kilogram per hectare, the weight ratio cf the bifenox to the benzoic acid herbicide suitably being in the ratio of 60:1 to 1:1, preferably 30:1 to 4:1. The benzoic acid herbioide may be employed in ~he fcrm of a salt thereof, especially an alkali metal salt such as a sodium or potassium salt, or in the form of an ester $hereof, e.g. a Cl-C8 alkyl ester.
.
~here a phenoxy acid herbicide, which i5 dichloroprop or 2,4-DB, Z5 i~ employed, such is preferably applied at a rate o~ 0.1 ~o 3.5 kilogram per hectare, the weight ratio of the bifenox to the phenoxy acid herbicide suitably being in the ratio of 30:1 to 1:15, especially from 8:1 to 1:6. In a particularly preferred embodiment, the bifenox is applied at a rate of 0.5 to 0.75 kilogram per hectare, the phenoxy acid herbicide at a rate of 1.5 to 3.0 kilogram per hectare. The phenoxy acid herbicide is suitably employed in the ~orm of a salt thereof, for example as an alkali metal salt, especially the sodium or potassium salt, or as an amine or ammonium salt. AS examples of ester forms of the phenoxy acid herbicide may be given those containing from 1 to 8 carbon atoms in the ester grouping, for example the ethyl, isopropyl and butyl esters.
~3~ 6 Where a dinitrophenol herbicide, which is DNOC, dinoterb or dinoseb is employed, such is preferably applied at a ra~e of from 0.5 to
5.0 kilogram per hectare, more preferably, particularly in the case of dinoterb or dinoseb, at a rate of 0.5 to 2.0 kilogram per hectare. The weight ra~io of bifenox to dinitrophenol herbicide is preferably from 6:1 to 1:20, more preferably from 3:1 to 1:6. As examples of suitable salt forms of the dinitrophenol herbicide may be given those formed with both inorganic and organic bases, especially the amine and ammonium salts. As examples o~ esters may be given those formed with organic acids, e.g.
carboxylic acids, for example dinoseb acetate.
Where a benzonitrile herbicide, which is io~ynil or bromoxynil, is employed, su~h is prePerably applied at a rate of from 0.05 to 0.5 kilogram per hectare, more preferably at a rate of from 0.1 ~o 0.35 kilogram per hectare. The weight ratio of bifenox to the benzonitrile herbicide is preferably from 60:1 to 1:2, more preferably from 15:1 to 2:1. In a particular embodiment, both ioxynil and bromoxynil are employed together with the bi~enox, in which case the preferred rates of application and weight ratios given above are based on the total weight of bo~h the ioxynil and brom~synil. Preferred salt forms of the ioxynil and bromoxynil are the alkali metal, such as sodium and potassium, salt forms. PrePerred esters include ioxynil octanoake a~d bromo~ynil octanoate.
Where benazolin is employed, such is preferably applied at a rate of from 0.05 to 0.25 kilogram per hectare. The ~eight ratio of bifenox to benazolin is preferably from 60:1 to l:l, m~re preferably from 15:1 to 5:2. Suitable salt forms of the benazolin include the alkali metal, especially the sodium and potassium, salt forms. The preferred esters are those containing from l to 4 carbon atoms in the ester grouping, especially the ethyl ester.
Where bentazone is employed, such is preferably applied at a rate of from 0.1 to 1.5, more preferably 0.2 to 1.5 and most preferably 0.5 ~o 1.5 kilogram per hectare. A preferred weight ratio of bifenox to bentazone is from 6:1 to 1:6, more preferably 3:1 to 1:2.
3~
Where 3,6 DCP is employed, such is preferably applied at a rate of from 0.025 to 0.15 kilogram per hectare, more preferably at a rate of from O.OS to 0.1 kilogram per hectare. A preferred weight ratio of biEenox to 3,6 DCP is from 30:1 to 3:1, more preferably from 15:1 to 5:1. As examples of salt forms of the 3,6 DCP may be given the alkali metal, e.g. sGdium and potassium, salt forms and ~he amine and ammonium salt forms, e.g. the monoethanolamine salt form. As examples of esters may be given those containing from 1 to 8 carbon atoms in the ester grouping.
~;
The meth~d of the present inventicn is preferably carried out when the cereal crop is between the one leaf stage and the appearance of the second node.
Where the bifenox is employed together with the benzoic acid herbicide, particularly good control of the weed species ~tellaria media, Pol~on m spp, ~E~ arvensis, _ril~leuroapermum marit um, Viola sPP
and Veronica ~Ee is observed.
,: ~
Where the bienox is employe~ together with the phenoxy acid herbicide, particularly good control of the weed species Galium aparine.
Stellaria media and Veronica spp is observ~d.
Where the bifenox is employed together with the dinitrophenol herbicide, particularly good control of the weed specie~ Galeopsis tetrahit, Fumaria officinalis, Polygonum convolvulus and Gal~um aparine is observed.
Where the bifenox is employed together with the ben~onitrile herbicide, particularly good control of the weed species Matricaria spp, Polygonum ~e and Galium aparine is observed.
Where the bifanox is employed together with bena~olin, particularly good control of the weed spe~ies Stellarla ~ L Galium aearine and iola s~e is observed.
,~ ', ~L33L~3~
Where the bifenox is employed together with benta~one, particularly good control of the weed species Viola ~, Veronica ~e and Matricaria sPP is observed.
Where the bifenox is employed together with 3,6 DCP, particularly good control of the weed species Veronica ~e and Matricaria spp is observedO
AR e~amples of further or additional herbicidally active compounds which may be employed together with the bife~ox and çomponent (l) to (7), above, may be given MCPA, MCPB and mecoprop, all of which are well kncwn herbicides, well documented in the literature and listed in the "Pesticide Manualn, fifth editionl issued by the British Crop Protection Council.
The bifenox and the active ingredient(s) ~l) to (7), abo~e, optionally alcng with any further or additional herbicidally active compound may be applied to the crop locus either simultaneously or separa~ely. I~ the latter, the time period between applications is preferably short, say one day or les;. It is b~ far preferred, however, for the compounds W be applied 6imultaneou~ly as a single formulation.
In order to simplify manufacture, storage and transport, herbicidal ~ormulations will normally be produced in concentrate form intended for dilution with water to the degree necessary to enable the above application rates ~o be achieved, which dilution is generally such that the formulation to be applied to the crop loc~s contains from 0.05 to 3.0 per cent by weight of the active herbicide ingredients. The concentrate formulaticns generally contain from l to 90%, preferably 15 to 85% of active ingredients assGciated with one or more non-phytotoxic carriers or diluent Concentrate formulations form part of the present invention.
Thus, there i5 provided a concentrated herbicidal ~ormulation which can particularly, though by no means e~clusively, be employed in the method of the present invention, which formulation comprises bifeno~, one or ~L~3~13~
more further active ingredients selected from (l) a benzoic acid he}bicide which is dicamba or 2,3,6~TBA or a salt or ester thereof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide ~hich is DNOC, dinoterb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which i5 ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof~ in association with one or more non-phytotoxic carriers or diluents.
- In such formulation, the weight ratios of bifenox to each of the ingredients (l) to (7) are preferably as set out a~ove in connection with the method of the invention.
The concentrate formulations according to the invention will usually be in the form of a wettable pcwder, an emulsifiable concentrate or an aqueous s~spension. Aqueous suspension and wettable powder formulations are preferred for use in the method of the invention, giving significantly lower phytotoxlcity to ~he cereal crop ~han the emulsifiable concentrate.
Wettable powders comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may, ~or example, be chos~n from the attapulgite clays, the monbmorillonite clays, thç diatomaceous earths, kaolins, micas, talcs and puriied silicates. Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and nonionic sur~a~tants such as ethylene oxide adducts o~
phenol.
Emulsifiable concentrates comprise the active ingredients dissolved in a suitable solvent or suitable solvents, together with a surfactant. Suitabie surfactants may, for example, be chosen from those mentioned above in connection with wettable powders. Suitable solvents include alkyl substituted benzenes, o-chlorotoluene, heavy aromatic naphthalenes, glycol ethers and cyclic ketones.
Aqueous suspensions and solutions comprise the active ingredients suspended or dissolved in water or suitable solvents r&spectively together with any desired surfactants, thickening aqentsy antifreezing agents or preservatives. Suitable surfactants may be chosen from those mentioned a~o~e in connection with wettable powdersO
Thickening agents, if used, are no~mally chosen from appropriate cellulose material~ and natural gums whilst glycols will generally be used when an antifreezing agent is required. Preservatives may be chosen - from a wide range of materials such as the ~arious paraben antibacterials, phenol, o-chlorocresol, phenyl mercuric nitrate and formaldehyde.
Alternatively, herbicidal formulations may be formed by mi~ing tha two or more active ingredients with water in a spray tank just prior to use, the water thus acting as a non-phytotoxic carrier. Such formulations are called "tank mixes" and form a further aspect of the invention. ID such tank mixes, the weight ratios of bifenox to the other ingredient (1) to ~7) are again p~eferably those given for the method of the invention.
The ~ollowing ~xa~ples illustriate concentrated herbicidal for~ulations according to the invention. Where a herbicidal ingredient is a aerivative of an asid or phenol the amount is based on the acid or phenol equivalent.
EXAMPLBS 1 to lO
The ~ollo~ing wettable powders were prepared in each ase with the ingredients shown.
% b;~ weight ~l) Bifeno~ 25 ~entazone 25 Sodium alkyl ether sulphate 3 Sulphonated lignin 2 3~
9 .
Preclpitated silica 6 Talc tolO0 (2) Bifenox 50 Ioxynil 5 ~odium salt of condensed naphthalene Sulphonic aclds 2 Ethoxylat~d alkyl phenol 4 Fumed silica 5 Montmor illonite to100 (3) Bifenox 42 BrGmoxynil 6 Sodium lauryl sulphate 5 Sodium lignin sulphonate 3 Precipitated silica 8 Raolin tolO0 ~43 Bi~enox 48 Benazolin (ethyl ester) 4 Ethoxylated nonyl phenol 4 Sulphite lye pawder 4 Fumed silica 5 Attapulgite ~olO0 (5) Bl~eno~ 4 3,6 DCP (monoethanolamine sal~) 4 Sodium lauryl sulphate 4 Sodium lignin sulphonate 3 Precipitated silica 8 Raolin ~olO0 .
: ., .
:
, ;
' ~3~
carboxylic acids, for example dinoseb acetate.
Where a benzonitrile herbicide, which is io~ynil or bromoxynil, is employed, su~h is prePerably applied at a rate of from 0.05 to 0.5 kilogram per hectare, more preferably at a rate of from 0.1 ~o 0.35 kilogram per hectare. The weight ratio of bifenox to the benzonitrile herbicide is preferably from 60:1 to 1:2, more preferably from 15:1 to 2:1. In a particular embodiment, both ioxynil and bromoxynil are employed together with the bi~enox, in which case the preferred rates of application and weight ratios given above are based on the total weight of bo~h the ioxynil and brom~synil. Preferred salt forms of the ioxynil and bromoxynil are the alkali metal, such as sodium and potassium, salt forms. PrePerred esters include ioxynil octanoake a~d bromo~ynil octanoate.
Where benazolin is employed, such is preferably applied at a rate of from 0.05 to 0.25 kilogram per hectare. The ~eight ratio of bifenox to benazolin is preferably from 60:1 to l:l, m~re preferably from 15:1 to 5:2. Suitable salt forms of the benazolin include the alkali metal, especially the sodium and potassium, salt forms. The preferred esters are those containing from l to 4 carbon atoms in the ester grouping, especially the ethyl ester.
Where bentazone is employed, such is preferably applied at a rate of from 0.1 to 1.5, more preferably 0.2 to 1.5 and most preferably 0.5 ~o 1.5 kilogram per hectare. A preferred weight ratio of bifenox to bentazone is from 6:1 to 1:6, more preferably 3:1 to 1:2.
3~
Where 3,6 DCP is employed, such is preferably applied at a rate of from 0.025 to 0.15 kilogram per hectare, more preferably at a rate of from O.OS to 0.1 kilogram per hectare. A preferred weight ratio of biEenox to 3,6 DCP is from 30:1 to 3:1, more preferably from 15:1 to 5:1. As examples of salt forms of the 3,6 DCP may be given the alkali metal, e.g. sGdium and potassium, salt forms and ~he amine and ammonium salt forms, e.g. the monoethanolamine salt form. As examples of esters may be given those containing from 1 to 8 carbon atoms in the ester grouping.
~;
The meth~d of the present inventicn is preferably carried out when the cereal crop is between the one leaf stage and the appearance of the second node.
Where the bifenox is employed together with the benzoic acid herbicide, particularly good control of the weed species ~tellaria media, Pol~on m spp, ~E~ arvensis, _ril~leuroapermum marit um, Viola sPP
and Veronica ~Ee is observed.
,: ~
Where the bienox is employe~ together with the phenoxy acid herbicide, particularly good control of the weed species Galium aparine.
Stellaria media and Veronica spp is observ~d.
Where the bifenox is employed together with the dinitrophenol herbicide, particularly good control of the weed specie~ Galeopsis tetrahit, Fumaria officinalis, Polygonum convolvulus and Gal~um aparine is observed.
Where the bifenox is employed together with the ben~onitrile herbicide, particularly good control of the weed species Matricaria spp, Polygonum ~e and Galium aparine is observed.
Where the bifanox is employed together with bena~olin, particularly good control of the weed spe~ies Stellarla ~ L Galium aearine and iola s~e is observed.
,~ ', ~L33L~3~
Where the bifenox is employed together with benta~one, particularly good control of the weed species Viola ~, Veronica ~e and Matricaria sPP is observed.
Where the bifenox is employed together with 3,6 DCP, particularly good control of the weed species Veronica ~e and Matricaria spp is observedO
AR e~amples of further or additional herbicidally active compounds which may be employed together with the bife~ox and çomponent (l) to (7), above, may be given MCPA, MCPB and mecoprop, all of which are well kncwn herbicides, well documented in the literature and listed in the "Pesticide Manualn, fifth editionl issued by the British Crop Protection Council.
The bifenox and the active ingredient(s) ~l) to (7), abo~e, optionally alcng with any further or additional herbicidally active compound may be applied to the crop locus either simultaneously or separa~ely. I~ the latter, the time period between applications is preferably short, say one day or les;. It is b~ far preferred, however, for the compounds W be applied 6imultaneou~ly as a single formulation.
In order to simplify manufacture, storage and transport, herbicidal ~ormulations will normally be produced in concentrate form intended for dilution with water to the degree necessary to enable the above application rates ~o be achieved, which dilution is generally such that the formulation to be applied to the crop loc~s contains from 0.05 to 3.0 per cent by weight of the active herbicide ingredients. The concentrate formulaticns generally contain from l to 90%, preferably 15 to 85% of active ingredients assGciated with one or more non-phytotoxic carriers or diluent Concentrate formulations form part of the present invention.
Thus, there i5 provided a concentrated herbicidal ~ormulation which can particularly, though by no means e~clusively, be employed in the method of the present invention, which formulation comprises bifeno~, one or ~L~3~13~
more further active ingredients selected from (l) a benzoic acid he}bicide which is dicamba or 2,3,6~TBA or a salt or ester thereof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide ~hich is DNOC, dinoterb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which i5 ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof~ in association with one or more non-phytotoxic carriers or diluents.
- In such formulation, the weight ratios of bifenox to each of the ingredients (l) to (7) are preferably as set out a~ove in connection with the method of the invention.
The concentrate formulations according to the invention will usually be in the form of a wettable pcwder, an emulsifiable concentrate or an aqueous s~spension. Aqueous suspension and wettable powder formulations are preferred for use in the method of the invention, giving significantly lower phytotoxlcity to ~he cereal crop ~han the emulsifiable concentrate.
Wettable powders comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may, ~or example, be chos~n from the attapulgite clays, the monbmorillonite clays, thç diatomaceous earths, kaolins, micas, talcs and puriied silicates. Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and nonionic sur~a~tants such as ethylene oxide adducts o~
phenol.
Emulsifiable concentrates comprise the active ingredients dissolved in a suitable solvent or suitable solvents, together with a surfactant. Suitabie surfactants may, for example, be chosen from those mentioned above in connection with wettable powders. Suitable solvents include alkyl substituted benzenes, o-chlorotoluene, heavy aromatic naphthalenes, glycol ethers and cyclic ketones.
Aqueous suspensions and solutions comprise the active ingredients suspended or dissolved in water or suitable solvents r&spectively together with any desired surfactants, thickening aqentsy antifreezing agents or preservatives. Suitable surfactants may be chosen from those mentioned a~o~e in connection with wettable powdersO
Thickening agents, if used, are no~mally chosen from appropriate cellulose material~ and natural gums whilst glycols will generally be used when an antifreezing agent is required. Preservatives may be chosen - from a wide range of materials such as the ~arious paraben antibacterials, phenol, o-chlorocresol, phenyl mercuric nitrate and formaldehyde.
Alternatively, herbicidal formulations may be formed by mi~ing tha two or more active ingredients with water in a spray tank just prior to use, the water thus acting as a non-phytotoxic carrier. Such formulations are called "tank mixes" and form a further aspect of the invention. ID such tank mixes, the weight ratios of bifenox to the other ingredient (1) to ~7) are again p~eferably those given for the method of the invention.
The ~ollowing ~xa~ples illustriate concentrated herbicidal for~ulations according to the invention. Where a herbicidal ingredient is a aerivative of an asid or phenol the amount is based on the acid or phenol equivalent.
EXAMPLBS 1 to lO
The ~ollo~ing wettable powders were prepared in each ase with the ingredients shown.
% b;~ weight ~l) Bifeno~ 25 ~entazone 25 Sodium alkyl ether sulphate 3 Sulphonated lignin 2 3~
9 .
Preclpitated silica 6 Talc tolO0 (2) Bifenox 50 Ioxynil 5 ~odium salt of condensed naphthalene Sulphonic aclds 2 Ethoxylat~d alkyl phenol 4 Fumed silica 5 Montmor illonite to100 (3) Bifenox 42 BrGmoxynil 6 Sodium lauryl sulphate 5 Sodium lignin sulphonate 3 Precipitated silica 8 Raolin tolO0 ~43 Bi~enox 48 Benazolin (ethyl ester) 4 Ethoxylated nonyl phenol 4 Sulphite lye pawder 4 Fumed silica 5 Attapulgite ~olO0 (5) Bl~eno~ 4 3,6 DCP (monoethanolamine sal~) 4 Sodium lauryl sulphate 4 Sodium lignin sulphonate 3 Precipitated silica 8 Raolin ~olO0 .
: ., .
:
, ;
' ~3~
(6) Bifenox 20 2,4 DB (po~assi~n salt)30 Etboxylated alkyl phenol 2 Sulphite lye powder 4 Fu~ed silica 5 Attapulgite to.. 100
(7) ~3ifenox 20 Dichlorprop ~potag8i~n salt) 40 Sodium dialkylsulpho uccinate 3 Lignosulphonate 2 Micronised sllica 7 Dia'~o~ac~ls earth to 100
(8) Bifenox 45 Io~:yn il 2 . 5 Bro~o~nil 3 Sodium lauryl sulphate 2 Sodium llgnin sulphQnate 3 Preclpitated silica Mon~morillonite to 100 ~9) Bifeno~ 40 2,3~6~q~A (sodiUrQ ~alt1 5 Sodilm~ lauryl sulphate 3 Sodium lignin 3ulphonate 3 Precipitated ~illca 4 ~aolin to 100 ~10), 3i~enox 40 Dicamba ~ 50d iU~I sal~) 4 Ethoxylated alkyl phenol 4 Lignosulphonate 2 Fumed silica Sod ium alumino silicate to 100 ~$
, "
~3~3~k~ !
In each Example, the active ingre~ient6 were carefully blended with the sp~cified exolpients in conventional mixing equipment. The blend wa~ then fur~her milled in a fluid energy mill to a size range of from 1 bD 10 microns.
EXAMP~ES 11 TO 2~
The following emulsi~iable concentrat~s were p~epared having ~he con8tituents RhaWn below :
~ll) Bifenox 25 Io~ynil toctanoate~ 3 Cal~ium dodecylbenzene ~ulphonate 4 AlkylphenQxypolyD~yethylene ethanol~ 2 Cyclohexanone 35 Xylene tol00 ~l2). Bifenox 20 Bromoxynil (octanoate3 Amine salt of d~decylbenzene ~ulphoic acid 3 Polyoxyethylene triglyceride 3 Cyclohexanona 30 Orthochlorotolu~ne tol00 25 ~13) Bi~enox 20 Benazolin ~ethyl e~ter) 2 Calciu~ dcdecylbenzene sulphonate 2 ~thoxylatYd alkyl phenol 4 Isophorone 35 ~eavy aro~atic naphtha tol00 ~14) Bi~nox 6 Calc~um dodecylbenzene sulphonate 3 EthoxylatPd alkyl pbenol 3 C~clohexanone 25 ~eævy aromatic naphtha tol00 ~' i' r '; ' ~' ~L3~3~
(15) Bifenox 20 Dinoterb 10 Al!cyl aryl sulphonate 2 Alkylphenoxypolyoxyethylene ethanol s Isophorone 30 O}thochlorotoluene to 100 (1~) Bifenox 15 Dinoseb 15 1o Amine ~alt of dedecylbenzenesulphonic acid 4 Pol~oxyethylene triglyceride 3 Isophorone 20 Heavy aromatic naphtha to 100 ~17) Bifenox 20 3,6 ncP 4 Calciu~ dodecylbenzene sulphonate Ethoxyla~ed alkyl phenol 4 Isophorone 30 ~eavy aro~atic naphtha to 100 (18) Bifenox lS
2,4-DB (isopropyl ester) 30 U kyl aryl sulphonate Polyoxyethylene triglyceride Cy~lohexanone 25 Xylene to 100 (19) Bifenox 15 Dichlorprop (butyl ester) 45 Amine salt of dodecylbenzene sulphonate 3 Alkylpheno~ypolyoxyethylene ethanols 3 Cyclohexanone 25 ~eavy aromatic naphtha to 100 (20) Bifenox 20 Ioxynil ~o~tanoate) 1.5 Bromoxynil (octanoate) 2 Calcium dodecylbenzene sulphonate 3 Alkylphenoxypolyoxyethylene ethanols 4 Isophorone 30 Orthochlorotoluene to100 (21~ Bifenox 25 2~3,6-TBA (ester) 3 Calcium dodecylbenzene sulphonate 3 Ethoxylated alkyl phenol 3 Isophorone 30 Osthochlorotoluene to100 (22) Bifenox 20 Dica~ba 2 Alkyl aryl sulphonate 4 Alkylphenoxypoloxyethylene ethanols 2 Cyclohexanone 25 ~ylene to100 The active ingredient~ were added to the appropriate solvent(s) with stirxing and optional heating to facilitate solubilisation of the active materials. ~he surfactants were then add~d. After solubilisation the solu~ion was filtered to remove insoluble impuritie~.
~0 ~he following aqueous suspensions were prepared ~rom the constituents hown below :
% by_w qht/b~ volume (23) Bifeno~ 20 Bentazone 20 ~3~
Alkyl aryl sulphonate 2 Phosphate ester of an ethoxylated polyarylphenol neu~ralised with triethanolamine~ 2 Xanthan gum 0.2 5ilicone antifoam 0.1 Formaldehyde 0.2 Water tolO0 (24) Bifenox 40 Ioaynil (sodium salt) 4 Ethoxylated nonyl phenol - 3 ~ydro~ymethyl cellulose 2 Siliaone antifoam O.l Water tolO0 (25) 8ifenox 35 Bromoxynil (potassium salt~ 3.5 Ethoxylated nonyl phenol 2.5 Hydroxymethyl cellulose l.7 Silicone antifoam O.l Water tolO0 (26) Bifenox 48 Benazolin ~potassium salt) 8 Sodi~n lauryl ~ulphate 3 Attapulgite 1. 5 Silicone antifoam 0.15 Wa~er tolO0 The herbicide ingredients were mlxed with surfactants and antifoaming agent, then vigorou~ly stirred in water to form a coarse aqueous suspension. This was then wet-milled to reduce the particle si~e of the active ingredients to 0.5 to 20 microns. To this wet milled preparation was then added an aqueous suspension of the thickening or suspending agent ~hydrated).
,~ ~
~3L31~33~
The following Example 2~ is of the test method employed to asses the efficacy of the method and formula~ion o~ the invention EX~MP~E 2? TEST M~T~OD
: 5 The appropriate quantity of formulated produc~ (for example of one of the co~centrate formulations of the foregoing Examples 1 to 261 is added to water in a micro-spra~er which i~ subsequently agitated ~o ensure dispersion. The ~prayer is adjusted to deliver a volume equivalent to 200 litres per hectare at a press~re of 40 p.s.i~ (ca 2.72 atm3. A standard nozzle (Allman No.-0) delive~ing a fan shaped jet is fitted to the ~prayer~
Application is made post emergence to both crop and weeds, the crop size for diff~rent applications varying from the 3 leaf stage to beginning of stem extension. Weed ~ize at application can also be variable, ranging from the cotyledon stage ~o the small plant stage.
2~ .
. . , ,~
,' :
, .. . .
,
, "
~3~3~k~ !
In each Example, the active ingre~ient6 were carefully blended with the sp~cified exolpients in conventional mixing equipment. The blend wa~ then fur~her milled in a fluid energy mill to a size range of from 1 bD 10 microns.
EXAMP~ES 11 TO 2~
The following emulsi~iable concentrat~s were p~epared having ~he con8tituents RhaWn below :
~ll) Bifenox 25 Io~ynil toctanoate~ 3 Cal~ium dodecylbenzene ~ulphonate 4 AlkylphenQxypolyD~yethylene ethanol~ 2 Cyclohexanone 35 Xylene tol00 ~l2). Bifenox 20 Bromoxynil (octanoate3 Amine salt of d~decylbenzene ~ulphoic acid 3 Polyoxyethylene triglyceride 3 Cyclohexanona 30 Orthochlorotolu~ne tol00 25 ~13) Bi~enox 20 Benazolin ~ethyl e~ter) 2 Calciu~ dcdecylbenzene sulphonate 2 ~thoxylatYd alkyl phenol 4 Isophorone 35 ~eavy aro~atic naphtha tol00 ~14) Bi~nox 6 Calc~um dodecylbenzene sulphonate 3 EthoxylatPd alkyl pbenol 3 C~clohexanone 25 ~eævy aromatic naphtha tol00 ~' i' r '; ' ~' ~L3~3~
(15) Bifenox 20 Dinoterb 10 Al!cyl aryl sulphonate 2 Alkylphenoxypolyoxyethylene ethanol s Isophorone 30 O}thochlorotoluene to 100 (1~) Bifenox 15 Dinoseb 15 1o Amine ~alt of dedecylbenzenesulphonic acid 4 Pol~oxyethylene triglyceride 3 Isophorone 20 Heavy aromatic naphtha to 100 ~17) Bifenox 20 3,6 ncP 4 Calciu~ dodecylbenzene sulphonate Ethoxyla~ed alkyl phenol 4 Isophorone 30 ~eavy aro~atic naphtha to 100 (18) Bifenox lS
2,4-DB (isopropyl ester) 30 U kyl aryl sulphonate Polyoxyethylene triglyceride Cy~lohexanone 25 Xylene to 100 (19) Bifenox 15 Dichlorprop (butyl ester) 45 Amine salt of dodecylbenzene sulphonate 3 Alkylpheno~ypolyoxyethylene ethanols 3 Cyclohexanone 25 ~eavy aromatic naphtha to 100 (20) Bifenox 20 Ioxynil ~o~tanoate) 1.5 Bromoxynil (octanoate) 2 Calcium dodecylbenzene sulphonate 3 Alkylphenoxypolyoxyethylene ethanols 4 Isophorone 30 Orthochlorotoluene to100 (21~ Bifenox 25 2~3,6-TBA (ester) 3 Calcium dodecylbenzene sulphonate 3 Ethoxylated alkyl phenol 3 Isophorone 30 Osthochlorotoluene to100 (22) Bifenox 20 Dica~ba 2 Alkyl aryl sulphonate 4 Alkylphenoxypoloxyethylene ethanols 2 Cyclohexanone 25 ~ylene to100 The active ingredient~ were added to the appropriate solvent(s) with stirxing and optional heating to facilitate solubilisation of the active materials. ~he surfactants were then add~d. After solubilisation the solu~ion was filtered to remove insoluble impuritie~.
~0 ~he following aqueous suspensions were prepared ~rom the constituents hown below :
% by_w qht/b~ volume (23) Bifeno~ 20 Bentazone 20 ~3~
Alkyl aryl sulphonate 2 Phosphate ester of an ethoxylated polyarylphenol neu~ralised with triethanolamine~ 2 Xanthan gum 0.2 5ilicone antifoam 0.1 Formaldehyde 0.2 Water tolO0 (24) Bifenox 40 Ioaynil (sodium salt) 4 Ethoxylated nonyl phenol - 3 ~ydro~ymethyl cellulose 2 Siliaone antifoam O.l Water tolO0 (25) 8ifenox 35 Bromoxynil (potassium salt~ 3.5 Ethoxylated nonyl phenol 2.5 Hydroxymethyl cellulose l.7 Silicone antifoam O.l Water tolO0 (26) Bifenox 48 Benazolin ~potassium salt) 8 Sodi~n lauryl ~ulphate 3 Attapulgite 1. 5 Silicone antifoam 0.15 Wa~er tolO0 The herbicide ingredients were mlxed with surfactants and antifoaming agent, then vigorou~ly stirred in water to form a coarse aqueous suspension. This was then wet-milled to reduce the particle si~e of the active ingredients to 0.5 to 20 microns. To this wet milled preparation was then added an aqueous suspension of the thickening or suspending agent ~hydrated).
,~ ~
~3L31~33~
The following Example 2~ is of the test method employed to asses the efficacy of the method and formula~ion o~ the invention EX~MP~E 2? TEST M~T~OD
: 5 The appropriate quantity of formulated produc~ (for example of one of the co~centrate formulations of the foregoing Examples 1 to 261 is added to water in a micro-spra~er which i~ subsequently agitated ~o ensure dispersion. The ~prayer is adjusted to deliver a volume equivalent to 200 litres per hectare at a press~re of 40 p.s.i~ (ca 2.72 atm3. A standard nozzle (Allman No.-0) delive~ing a fan shaped jet is fitted to the ~prayer~
Application is made post emergence to both crop and weeds, the crop size for diff~rent applications varying from the 3 leaf stage to beginning of stem extension. Weed ~ize at application can also be variable, ranging from the cotyledon stage ~o the small plant stage.
2~ .
. . , ,~
,' :
, .. . .
,
Claims (8)
1. A method of controlling weeds in a cereal crop locus, which method comprises applying to said locus, post-emergence the crop, bifenox being a compound of formula I, I
and one or more further active ingredients selected from (1) a benzoic acid herbicide which is dicamba or 2,3,6-TBA or a salt or ester thereof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide which is DNOC, dinoterb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which is ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof; and wherein the benzoic acid herbicide is applied at a rate of from 0.05 to 0.2 kilogram per hectare, the phenoxy acid herbicide is applied at a rate of 0.1 to 3.5 kilogram per hectare, the dinitrophenol herbicide is applied at a rate of 0.5 to 5.0 kilogram per hectare, the benzonitrile herbicide is applied at a rate of 0.05 to 0.5 Kilogram per hectare, the bentazone is applied at a rate of from 0.05 to 0.25 kilorgram per hectare, the bentazone is applied at a rate of from 0.1 to 1.5 kilogram per hectare and the 3,6-DCP is applied at a rate of from 0.025 to 0.15 kilogram per hectare.
and one or more further active ingredients selected from (1) a benzoic acid herbicide which is dicamba or 2,3,6-TBA or a salt or ester thereof, (2) a phenoxy acid herbicide which is dichlorprop or 2,4-DB or a salt or ester thereof, (3) a dinitrophenol herbicide which is DNOC, dinoterb or dinoseb or a salt or ester thereof, (4) a benzonitrile herbicide which is ioxynil or bromoxynil or a salt or ester thereof, (5) benazolin or a salt or ester thereof, (6) bentazone and (7) 3,6-DCP or a salt or ester thereof; and wherein the benzoic acid herbicide is applied at a rate of from 0.05 to 0.2 kilogram per hectare, the phenoxy acid herbicide is applied at a rate of 0.1 to 3.5 kilogram per hectare, the dinitrophenol herbicide is applied at a rate of 0.5 to 5.0 kilogram per hectare, the benzonitrile herbicide is applied at a rate of 0.05 to 0.5 Kilogram per hectare, the bentazone is applied at a rate of from 0.05 to 0.25 kilorgram per hectare, the bentazone is applied at a rate of from 0.1 to 1.5 kilogram per hectare and the 3,6-DCP is applied at a rate of from 0.025 to 0.15 kilogram per hectare.
2. A method according to claim 1 wherein the bifenox is applied together with both ioxynil and bromoxynil.
3. A method according to claim 1 wherein the bifenox is applied at a rate of from 0.5 to 1.5 kilogram per hectare.
4. A method according to claim 1, 2 or 3 wherein the rate of application of bifenox is from 0.5 to 0.75 kilogram per hectare.
5. A method according to claim 1 or 3 wherein the bifenox is applied at a rate of 0.5 to 0.75 kilogram per hectare and the phenoxy acid herbicide is applied at a rate of 1.5 to 3.0 kilogram per hectare.
6. A herbicidal formulation which is a concentrate or a tank mix and comprising bifenox and one or more of the active ingredients (1) to (7), given in claim 1, in association with one o- more non-phytotoxic diluents or carriers, said formulation comprising an aqueous suspension or a wettable powder.
7. A herbicidal formulation according to claim 6, wherein the weight ratio of bifenox to the benzoic acid herbicide is from 60:1 to 1:1, the weight ratio of bifenox to the phenoxy acid herbicide is from 30:1 to 1:15, the weight ratio of bifenox to the dinitrophenol herbicide is from 6:1 to 1:20, the weight ratio of bifenox to the benzonitrile herbicide is from 60:1 to 1:2, the weight ratio of bifenox to benazolin is from 60:1 to 1:1, the weight ratio of bifenox to bentazone is from 6:1 to 1:6 and the weight ratio of bifenox to 3,6 DCP is from 30:1 to 3:1.
8. A herbicidal formulation according to claim 6 or 7 which is a concentrate formulation and which contains from 15 to 85% of active ingredients.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49440/78 | 1978-12-21 | ||
| GB7849440 | 1978-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131036A true CA1131036A (en) | 1982-09-07 |
Family
ID=10501858
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,754A Expired CA1129665A (en) | 1978-12-21 | 1979-07-13 | Method of combating weeds in cereal crops and herbicidal formulation therefor |
| CA342,403A Expired CA1131036A (en) | 1978-12-21 | 1979-12-20 | Herbicidal treatments and formulations |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,754A Expired CA1129665A (en) | 1978-12-21 | 1979-07-13 | Method of combating weeds in cereal crops and herbicidal formulation therefor |
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|---|---|
| JP (6) | JPS5589204A (en) |
| BE (1) | BE880782A (en) |
| BR (1) | BR7908349A (en) |
| CA (2) | CA1129665A (en) |
| CH (1) | CH641932A5 (en) |
| DD (1) | DD147993A5 (en) |
| DE (1) | DE2950682A1 (en) |
| FR (1) | FR2444407A1 (en) |
| GB (1) | GB2042339B (en) |
| HK (1) | HK73985A (en) |
| IE (1) | IE49337B1 (en) |
| IL (1) | IL58962A0 (en) |
| IT (1) | IT1162429B (en) |
| JO (1) | JO985B1 (en) |
| LU (1) | LU82017A1 (en) |
| MA (1) | MA18678A1 (en) |
| MX (1) | MX6293E (en) |
| NL (1) | NL7909099A (en) |
| NO (1) | NO794206L (en) |
| NZ (1) | NZ192415A (en) |
| PL (1) | PL220528A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8304102D0 (en) * | 1983-02-15 | 1983-03-16 | Rohm & Haas France | Herbicidal compositions |
| GB8403342D0 (en) * | 1984-02-08 | 1984-03-14 | Velsicol Chemical Ltd | Herbicidal compositions |
| EP0186971A1 (en) * | 1984-11-28 | 1986-07-09 | Ivon Watkins-Dow Limited | Herbicidal compositions and methods |
| GB8511998D0 (en) * | 1985-05-11 | 1985-06-19 | Fbc Ltd | Herbicides |
| NZ223585A (en) * | 1987-02-24 | 1990-09-26 | Rhone Poulenc Agrochimie | Herbicidal mixture of picolinic acid or 2-pyridyloxyacetic acid derivatives and a phenoxy benzoic acid derivative |
| DE4223465A1 (en) * | 1992-07-16 | 1994-01-20 | Bayer Ag | Herbicidal agents based on heteroaryloxyacetamides |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR751855A (en) * | 1932-06-04 | 1933-09-11 | Selective destruction of weeds and improvement of crops | |
| US2192197A (en) * | 1936-09-03 | 1940-03-05 | Dow Chemical Co | Dinitro-alkyl-phenol |
| US3081162A (en) * | 1956-11-27 | 1963-03-12 | Heyden Newport Chemical Corp | Controlling bindweed with 2, 3, 6-trichlorobenzoic acid and salts thereof |
| NL222768A (en) * | 1957-09-26 | |||
| US3013054A (en) * | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | 2-methoxy-3, 6-dichlorobenzoates |
| NL108409C (en) * | 1958-10-29 | |||
| GB977755A (en) * | 1962-09-04 | 1964-12-16 | Nippon Catalytic Chem Ind | Method of preparing aromatic nitriles |
| US3317549A (en) * | 1963-03-25 | 1967-05-02 | Dow Chemical Co | Picolinic acid compounds |
| FR1475686A (en) * | 1965-11-30 | 1967-04-07 | Pechiney Progil Sa | Selective weed control of cereals |
| US3708277A (en) * | 1966-08-30 | 1973-01-02 | Basf Ag | Herbicidal method |
| US3652645A (en) * | 1969-04-25 | 1972-03-28 | Mobil Oil Corp | Halophenoxy benzoic acid herbicides |
| NL175780C (en) * | 1972-11-17 | 1985-01-02 | Rhone Poulenc Inc | PROCESS FOR PREPARING A HERBICIDE PREPARATION CONTAINING AT LEAST A PHENOXYNITROBENZOATE |
| JPS5857403B2 (en) * | 1973-08-20 | 1983-12-20 | ホクコウカガクコウギヨウ カブシキガイシヤ | Japanese porridge |
| JPS5924122B2 (en) * | 1973-08-20 | 1984-06-07 | 北興化学工業 （株） | herbicide composition |
| JPS5857402B2 (en) * | 1973-08-20 | 1983-12-20 | ホクコウカガクコウギヨウ カブシキガイシヤ | Japanese porridge |
| JPS562527B2 (en) * | 1973-08-20 | 1981-01-20 | ||
| JPS50125030A (en) * | 1974-03-23 | 1975-10-01 | ||
| JPS5919081B2 (en) * | 1975-04-28 | 1984-05-02 | 三井東圧化学株式会社 | Herbicide composition for paddy fields |
| JPS52139719A (en) * | 1976-04-19 | 1977-11-21 | Mitsui Toatsu Chem Inc | Herbicidal composition |
| EP0001328A1 (en) * | 1977-09-23 | 1979-04-04 | FISONS plc | Method and composition for combating weeds |
-
1979
- 1979-07-13 CA CA331,754A patent/CA1129665A/en not_active Expired
- 1979-08-15 JO JO1979985A patent/JO985B1/en active
- 1979-12-14 MX MX798559U patent/MX6293E/en unknown
- 1979-12-14 IL IL58962A patent/IL58962A0/en unknown
- 1979-12-15 DE DE19792950682 patent/DE2950682A1/en not_active Withdrawn
- 1979-12-15 MA MA18880A patent/MA18678A1/en unknown
- 1979-12-17 GB GB7943358A patent/GB2042339B/en not_active Expired
- 1979-12-17 NZ NZ192415A patent/NZ192415A/en unknown
- 1979-12-17 RO RO7999570A patent/RO78398A/en unknown
- 1979-12-17 CH CH1114279A patent/CH641932A5/en not_active IP Right Cessation
- 1979-12-18 FR FR7930949A patent/FR2444407A1/en active Granted
- 1979-12-18 NL NL7909099A patent/NL7909099A/en active Search and Examination
- 1979-12-19 PL PL22052879A patent/PL220528A1/xx unknown
- 1979-12-19 BR BR7908349A patent/BR7908349A/en unknown
- 1979-12-20 NO NO794206A patent/NO794206L/en unknown
- 1979-12-20 JP JP16626679A patent/JPS5589204A/en active Pending
- 1979-12-20 IT IT51151/79A patent/IT1162429B/en active
- 1979-12-20 IE IE2488/79A patent/IE49337B1/en not_active IP Right Cessation
- 1979-12-20 DD DD79217958A patent/DD147993A5/en unknown
- 1979-12-20 CA CA342,403A patent/CA1131036A/en not_active Expired
- 1979-12-20 BE BE6/47042A patent/BE880782A/en not_active IP Right Cessation
- 1979-12-20 LU LU82017A patent/LU82017A1/en unknown
- 1979-12-21 TR TR20965A patent/TR20965A/en unknown
-
1985
- 1985-06-11 SG SG44385A patent/SG44385G/en unknown
- 1985-09-26 HK HK739/85A patent/HK73985A/en not_active IP Right Cessation
-
1989
- 1989-02-07 JP JP1028523A patent/JPH01287003A/en active Pending
- 1989-02-07 JP JP1028520A patent/JPH01308207A/en active Pending
- 1989-02-07 JP JP1028524A patent/JPH01287004A/en active Pending
- 1989-02-07 JP JP1028522A patent/JPH01308209A/en active Pending
- 1989-02-07 JP JP1028521A patent/JPH01308208A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MA18678A1 (en) | 1980-07-01 |
| BE880782A (en) | 1980-06-20 |
| GB2042339A (en) | 1980-09-24 |
| HK73985A (en) | 1985-10-04 |
| PL220528A1 (en) | 1980-09-22 |
| JPH01287004A (en) | 1989-11-17 |
| SG44385G (en) | 1986-01-17 |
| IT7951151A0 (en) | 1979-12-20 |
| FR2444407A1 (en) | 1980-07-18 |
| IL58962A0 (en) | 1980-03-31 |
| NL7909099A (en) | 1980-06-24 |
| GB2042339B (en) | 1982-10-20 |
| NZ192415A (en) | 1982-03-30 |
| JPH01308207A (en) | 1989-12-12 |
| DD147993A5 (en) | 1981-05-06 |
| IT1162429B (en) | 1987-04-01 |
| CH641932A5 (en) | 1984-03-30 |
| TR20965A (en) | 1983-03-07 |
| FR2444407B1 (en) | 1984-09-28 |
| JPH01308208A (en) | 1989-12-12 |
| JPH01308209A (en) | 1989-12-12 |
| MX6293E (en) | 1985-03-18 |
| IE49337B1 (en) | 1985-09-18 |
| NO794206L (en) | 1980-06-24 |
| IE792488L (en) | 1980-06-21 |
| JPS5589204A (en) | 1980-07-05 |
| LU82017A1 (en) | 1981-07-23 |
| BR7908349A (en) | 1980-09-23 |
| JPH01287003A (en) | 1989-11-17 |
| JO985B1 (en) | 1979-12-01 |
| CA1129665A (en) | 1982-08-17 |
| RO78398A (en) | 1982-02-26 |
| DE2950682A1 (en) | 1980-07-17 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |