CA1129665A - Method of combating weeds in cereal crops and herbicidal formulation therefor - Google Patents
Method of combating weeds in cereal crops and herbicidal formulation thereforInfo
- Publication number
- CA1129665A CA1129665A CA331,754A CA331754A CA1129665A CA 1129665 A CA1129665 A CA 1129665A CA 331754 A CA331754 A CA 331754A CA 1129665 A CA1129665 A CA 1129665A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- rate
- stated
- bifenox
- 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.)
- Expired
Links
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
Abstract
ABSTRACT
The selective control of weeds in post-emergence treatment of cereal crops employing a combination of a compound of formula I
(I) and a compound of formula II
The selective control of weeds in post-emergence treatment of cereal crops employing a combination of a compound of formula I
(I) and a compound of formula II
Description
~Z9665 METHOD OF COMBATING WEEDS IN CEREAL CROPS
AND HERBICIDAL FORMULATIONS THEREFOR
The invention relates to a method of combating weeds in cereal crops and to herbicidal formulations for use in such method.
Heretofore, the broadleaf weed species Matricaria spp has proved particularly resistant to conventional herbicides, causing much damage to winterand spring cereal crops such as wheat, barley, oats and rye. We have now found that by using a combination of particular known herbicides this weed species is controlled to a surprisingly high level, synergism, in accordance with the well-known "Colby Equation" tW~, 15, 20-22, 1967), being observed.
Additionally, control of other problematic weed species has been found to be very satisfactory when using the combination, synergism again being observed in several cases.
Thus, according to the present invention a method of combating weeds in a cereal crQp locus comprises applying to said locus, post emergence the crop, acompound of formula 1, ., ID
CH3D- C:l 02N __~3 0 ~ Cl and one or more compounds of formula 11, ' .~
~CH3 (II) Cl ~ ~0- X- COOH
/
6~5 wherein X is -~H2- or -(CH2)3-, said compound of ormula II be mg optionally ~n a salt or ester form which is non-phytotoxic to cereal c.rops; where a compound of formLla II, m which X is -C~ -, is employed, t~ compound of formLla I being applied at a rate of 0.7 to 2.0 kg/ha and the compound of formula II being applied at a rate of 0.7 to 3.0 kg/ha, and where a co~pound of formNla II, in which X is -(CH2)3-, is employed, the co~pound of formula I being applied at a rate of 0.25 t~ 3.0 k~/ha and the compound of formula II being applied at a rate of 0.1 to 3.5 kg/ha.
In general, the compound of formula I is applied at a rate of from û.7 to
AND HERBICIDAL FORMULATIONS THEREFOR
The invention relates to a method of combating weeds in cereal crops and to herbicidal formulations for use in such method.
Heretofore, the broadleaf weed species Matricaria spp has proved particularly resistant to conventional herbicides, causing much damage to winterand spring cereal crops such as wheat, barley, oats and rye. We have now found that by using a combination of particular known herbicides this weed species is controlled to a surprisingly high level, synergism, in accordance with the well-known "Colby Equation" tW~, 15, 20-22, 1967), being observed.
Additionally, control of other problematic weed species has been found to be very satisfactory when using the combination, synergism again being observed in several cases.
Thus, according to the present invention a method of combating weeds in a cereal crQp locus comprises applying to said locus, post emergence the crop, acompound of formula 1, ., ID
CH3D- C:l 02N __~3 0 ~ Cl and one or more compounds of formula 11, ' .~
~CH3 (II) Cl ~ ~0- X- COOH
/
6~5 wherein X is -~H2- or -(CH2)3-, said compound of ormula II be mg optionally ~n a salt or ester form which is non-phytotoxic to cereal c.rops; where a compound of formLla II, m which X is -C~ -, is employed, t~ compound of formLla I being applied at a rate of 0.7 to 2.0 kg/ha and the compound of formula II being applied at a rate of 0.7 to 3.0 kg/ha, and where a co~pound of formNla II, in which X is -(CH2)3-, is employed, the co~pound of formula I being applied at a rate of 0.25 t~ 3.0 k~/ha and the compound of formula II being applied at a rate of 0.1 to 3.5 kg/ha.
In general, the compound of formula I is applied at a rate of from û.7 to
2.0 kg/ha and the compound(s) of formuta 11 at a rate of from 0.7 to 3.0 kg/ha.
The compound of formula I is known as bifenox, the preparation thereof being described in United Kingdom Patent Specification No. 11232,368 and its use as a herbicide being described in Proc. N E.~. 1973~ 27, 31.
The compound of formula 11, where X is -CH2_, is known as M.C.P.A.
The compound of formula 11, wherein X is -tCH2)3_, is known qs M.C.P.B.
M.C.P.A., M.C.P.B., their salts and esters, their manufacture and their herbicidal properties are well documented in the literature.
The compounds of formula 11 may be employed in free acid form or in a salt or ester form which is non-phytotoxia to cereals. As examples of sqlt forms may be giv~ the alkali-metal, e.g. sodium and potassium salt forms and the ammonium, alkylammonium and aikanolammonium salt forms, e.g. the ethanolammonium salt form. As examples of ester forms may be given the lower, e.g. C~ 8' alkyl ester forms, e.g. the methyi and octyl ester forms. The use ~f such salts and ester forrns is embraced by the present invention.
In the method of the present invention, the compound of formula I
(bifenox) is preferably employed at an applicGtion rate of from 0.7 to 1.5 kg/ha and more preferably at a rate of about 0.75 to 1.0 kg/ha.
~LZ~66s The compound of formula 11, wherein X is -(CH2)3_, i.e. A~.C.P.B., is preferablyemployed at an application rate of from 1.0 to 2.0 kg/ha. The compound of formula 11, wherein X is -CH2_, i.e. M.C.P.A., is preferably employed at an application rate of from 0.7 to 1.5 kg/ha and more preferably at a rate of about0.75 to l.Okg/ha.
The weight ratio of the compound of formula I to the compound(s) of formula 11 is generally in the range of from 1:4 to 3:1. Where the bifenox is employed together with All.C.P.B., the weight ratio of the former to the latter is preferably in the range of from i:3 to 1.5:1, more preferqbly about 1:2. Where the bifenox is employed together with l~A.C.P.A., the weight rqtio of the formerto the latter is preferqbly in the r~nge of from 1:2 to 2:1, more preferably about 1:1.
In the case of the cornpounds of formula 11, the above weights and ratios are based on the acid equivalent thereof if a sqlt or ester is employed.
The method of the present invention is preferably carried out when the
The compound of formula I is known as bifenox, the preparation thereof being described in United Kingdom Patent Specification No. 11232,368 and its use as a herbicide being described in Proc. N E.~. 1973~ 27, 31.
The compound of formula 11, where X is -CH2_, is known as M.C.P.A.
The compound of formula 11, wherein X is -tCH2)3_, is known qs M.C.P.B.
M.C.P.A., M.C.P.B., their salts and esters, their manufacture and their herbicidal properties are well documented in the literature.
The compounds of formula 11 may be employed in free acid form or in a salt or ester form which is non-phytotoxia to cereals. As examples of sqlt forms may be giv~ the alkali-metal, e.g. sodium and potassium salt forms and the ammonium, alkylammonium and aikanolammonium salt forms, e.g. the ethanolammonium salt form. As examples of ester forms may be given the lower, e.g. C~ 8' alkyl ester forms, e.g. the methyi and octyl ester forms. The use ~f such salts and ester forrns is embraced by the present invention.
In the method of the present invention, the compound of formula I
(bifenox) is preferably employed at an applicGtion rate of from 0.7 to 1.5 kg/ha and more preferably at a rate of about 0.75 to 1.0 kg/ha.
~LZ~66s The compound of formula 11, wherein X is -(CH2)3_, i.e. A~.C.P.B., is preferablyemployed at an application rate of from 1.0 to 2.0 kg/ha. The compound of formula 11, wherein X is -CH2_, i.e. M.C.P.A., is preferably employed at an application rate of from 0.7 to 1.5 kg/ha and more preferably at a rate of about0.75 to l.Okg/ha.
The weight ratio of the compound of formula I to the compound(s) of formula 11 is generally in the range of from 1:4 to 3:1. Where the bifenox is employed together with All.C.P.B., the weight ratio of the former to the latter is preferably in the range of from i:3 to 1.5:1, more preferqbly about 1:2. Where the bifenox is employed together with l~A.C.P.A., the weight rqtio of the formerto the latter is preferqbly in the r~nge of from 1:2 to 2:1, more preferably about 1:1.
In the case of the cornpounds of formula 11, the above weights and ratios are based on the acid equivalent thereof if a sqlt or ester is employed.
The method of the present invention is preferably carried out when the
3 crop is between the one leaf stage and appearance of the second node .
The preferred crops for treatment by the method of the present invention are winter wheat, spring barley and winter bqrley.
The compound of formulq I and the compound(s~ of formulq 11 may be applied together or separately. If the latter, the time period between applications is preferably short, sqy one day or less. It is by far preferred, however, for the compounds to be applied simultaneously as a single formulation. In order to simplify mqnufacture, storage and transport, herbicidalformulations will normally be produced in concentrate form intended for dilutionin w~ter to the degree necessqry to enable the above qpplicqtion rates to be Gchieved. Such concentrate formulations may contain from I to 9û%, preferably 15 to 85%, by weight of qctive ingredients qssociated with one or more inert, non phytotoxic, carriers therefor. Such formulations will usually be in the form of a wettable powder, an emulsifiable concentrate or ~n aqueous suspension or so~uti on.
.
', : ' .
' ' :
~12~6~S
Herbicidal formulations form a further aspect of the present invention.
Thus, there is provided a herbicidal formulation to be used in the method of theinvention, after dilution if appropriate, and comprising a compound of formula Iand one or more compounds of formula 11, or a salt or ester thereof, in a weightratio range of from 1:4 to 3:1 (based on the acid equivalent of the compound(s) of formula 11) together with a non-phytotoxic diluent or carrier. The preferred weight ratio ranges are as given above.
As a further separate aspect of the present invention, there is provided a herbicidal formulation comprising a compound of formula l,stated above, together with a compound of formula- Il, in which X is -(CH2)3_, or a salt or ester thereof, in a weight ratio range of from 1:4 to 3:1 (based on the acid equivalent of the compound of formula 11), together with q non-phytotoxic diluent or carrier. Again, the preferred weight ratio ranges are as given above.
The herbicidal formulations of the present invention are intended to embrace not only the so-called concentrate formulation forms, but also ready-to-use dilute formulations such as tank mixes and application spray liquors. Such dilute formulations are generally produced by dilution down to theappropriate degree of concentrate formulations but, if desired, may be produced by the sepclrate <Iddition of appropriate amounts of the individual components to an appropriate diluent or carrler.
Turning, however, to the concentrate formulations, wettable powders comprise an intimote mixture of the active ingredients, one or more inert carriers and one or more appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins, micas, talcs and purified silicates. Effective surfactants may be found among the sulphonated lignins, the naphthalene sulphonates and condensed naphthalene sulphonates, the alkyl succinates, the alkylbenzene sulphonates, ~2~3t665 the alkyl sulphates and non-ionic surfactants such as ethylene oxide adducts of phenol. Illustrative wettable powders are those having the following composition WETTABLE POWDERS
% by weight.
Compound of f ormu la I I to 73 Compound of formula 11* I to 79 Surf actant(s) I to I û
DispersingAgent Oto 10 Anticaking Agent û to lû
Inert carrier(s) to lûû
* based on acid equivalent Emulsifiable concentrates comprise the active ingredients dissolved in one or more suitable solvents, together with a surfactant. As examples of solvents may be given qlkyl substituted benzenes, o-chlorotoluene, heavy aromatic naphthalenes, glycol ethers and cyclic ketones. Illustrative emulsifiable concentrates are those having the following composition:
.
% weight/volume Compound of formula II to 55 Compound of formula 11* I to 60 SurfactGnt(s) 2 to 10 Co-solvent 0 to 40 Solvent to 100 * Based on acid equivalent Aqueous suspensions and solutions comprise the active ingredients suspended or dissolved in water together with any desired surfactants, thickening agents, cntifreezing agents or p~eservcltivesO
~.
. ; :
', .
~LZ~6~5 Suitable surfactants may be chosen from those mentioned above in connection with wettable powders. Thickening agents, if used, are normally chosen from appropriate cellulose materials 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 various paraben antibacteriqls, phenol, o-chlorocresol, phenyl mercuric nitrate Qnd formaldehyde. Illustrqtive aqueous suspensions are those having the following composition:
AQUEOUS SUSPENSIONS
% weight/volume l o Compound of formula 4 to 59 Compound of formula 11* 5 to 65 Wetting Agent 0 to 10 Dispersing Agent 0 to 6 Thickening/Suspending Agent 0 to 5 Antifree2e Agent 0 to 15 Preservative 0 to ;~
Water to lû0 * Based on acid eauivalent The aqueous suspension and wettable powder formulations are preferred o for use in the method of the present invention, giving significantly lower phytotoxicity to the cereal crop than the emulsifiable concentrate formulations.The followîng Examples further illustrate the invention '. In qll Examples, the amount of M.C.P.A and M.C.P.B used is based on the acid equivalent.
The following wettable powders were prepared, in each case having the ingredients shown:
6~5 % by weight (!\ R~jfenox ?!~
M.C.P.B. (sodium salt) 45 Sodium lauryl sulphate Sodium lignin sulphonate 3 Precipitated silica 5 Montmorillonite to lû0 Y by weight ~2) Bifenox 30 1 h~.C.P.A. (sodium salt) 30 Sodium lauryl sulphate 2 Sodium lignin sulphonate 3 Precipitated siliw 5 Montmori!lonite to 100 In each ~xample, the active ingredients were carefully blended with the specified excipients in conventional mixing equipment. The blend was then further milled in a fluid energy mill to a size range of from I to 10 microns .
;~o The following emulsifiable concentrqtes were prepared having the constituents shown below:
by volume (3) Bifenox 20 M.C.P.B. (rnixed butyl esters) 3û
Calcium dodecylbenzene sulphonate 3 Alkyl phenoxypolyoxyethylene ethanols 4 Isophorone 30 Orthochlorotoluene to 100 , ,, ,':
~ .. : ~ . ~ . !
-' ' ' ' ~"'';~ .
~Z~6~j .
% by weight/
by volume
The preferred crops for treatment by the method of the present invention are winter wheat, spring barley and winter bqrley.
The compound of formulq I and the compound(s~ of formulq 11 may be applied together or separately. If the latter, the time period between applications is preferably short, sqy one day or less. It is by far preferred, however, for the compounds to be applied simultaneously as a single formulation. In order to simplify mqnufacture, storage and transport, herbicidalformulations will normally be produced in concentrate form intended for dilutionin w~ter to the degree necessqry to enable the above qpplicqtion rates to be Gchieved. Such concentrate formulations may contain from I to 9û%, preferably 15 to 85%, by weight of qctive ingredients qssociated with one or more inert, non phytotoxic, carriers therefor. Such formulations will usually be in the form of a wettable powder, an emulsifiable concentrate or ~n aqueous suspension or so~uti on.
.
', : ' .
' ' :
~12~6~S
Herbicidal formulations form a further aspect of the present invention.
Thus, there is provided a herbicidal formulation to be used in the method of theinvention, after dilution if appropriate, and comprising a compound of formula Iand one or more compounds of formula 11, or a salt or ester thereof, in a weightratio range of from 1:4 to 3:1 (based on the acid equivalent of the compound(s) of formula 11) together with a non-phytotoxic diluent or carrier. The preferred weight ratio ranges are as given above.
As a further separate aspect of the present invention, there is provided a herbicidal formulation comprising a compound of formula l,stated above, together with a compound of formula- Il, in which X is -(CH2)3_, or a salt or ester thereof, in a weight ratio range of from 1:4 to 3:1 (based on the acid equivalent of the compound of formula 11), together with q non-phytotoxic diluent or carrier. Again, the preferred weight ratio ranges are as given above.
The herbicidal formulations of the present invention are intended to embrace not only the so-called concentrate formulation forms, but also ready-to-use dilute formulations such as tank mixes and application spray liquors. Such dilute formulations are generally produced by dilution down to theappropriate degree of concentrate formulations but, if desired, may be produced by the sepclrate <Iddition of appropriate amounts of the individual components to an appropriate diluent or carrler.
Turning, however, to the concentrate formulations, wettable powders comprise an intimote mixture of the active ingredients, one or more inert carriers and one or more appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins, micas, talcs and purified silicates. Effective surfactants may be found among the sulphonated lignins, the naphthalene sulphonates and condensed naphthalene sulphonates, the alkyl succinates, the alkylbenzene sulphonates, ~2~3t665 the alkyl sulphates and non-ionic surfactants such as ethylene oxide adducts of phenol. Illustrative wettable powders are those having the following composition WETTABLE POWDERS
% by weight.
Compound of f ormu la I I to 73 Compound of formula 11* I to 79 Surf actant(s) I to I û
DispersingAgent Oto 10 Anticaking Agent û to lû
Inert carrier(s) to lûû
* based on acid equivalent Emulsifiable concentrates comprise the active ingredients dissolved in one or more suitable solvents, together with a surfactant. As examples of solvents may be given qlkyl substituted benzenes, o-chlorotoluene, heavy aromatic naphthalenes, glycol ethers and cyclic ketones. Illustrative emulsifiable concentrates are those having the following composition:
.
% weight/volume Compound of formula II to 55 Compound of formula 11* I to 60 SurfactGnt(s) 2 to 10 Co-solvent 0 to 40 Solvent to 100 * Based on acid equivalent Aqueous suspensions and solutions comprise the active ingredients suspended or dissolved in water together with any desired surfactants, thickening agents, cntifreezing agents or p~eservcltivesO
~.
. ; :
', .
~LZ~6~5 Suitable surfactants may be chosen from those mentioned above in connection with wettable powders. Thickening agents, if used, are normally chosen from appropriate cellulose materials 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 various paraben antibacteriqls, phenol, o-chlorocresol, phenyl mercuric nitrate Qnd formaldehyde. Illustrqtive aqueous suspensions are those having the following composition:
AQUEOUS SUSPENSIONS
% weight/volume l o Compound of formula 4 to 59 Compound of formula 11* 5 to 65 Wetting Agent 0 to 10 Dispersing Agent 0 to 6 Thickening/Suspending Agent 0 to 5 Antifree2e Agent 0 to 15 Preservative 0 to ;~
Water to lû0 * Based on acid eauivalent The aqueous suspension and wettable powder formulations are preferred o for use in the method of the present invention, giving significantly lower phytotoxicity to the cereal crop than the emulsifiable concentrate formulations.The followîng Examples further illustrate the invention '. In qll Examples, the amount of M.C.P.A and M.C.P.B used is based on the acid equivalent.
The following wettable powders were prepared, in each case having the ingredients shown:
6~5 % by weight (!\ R~jfenox ?!~
M.C.P.B. (sodium salt) 45 Sodium lauryl sulphate Sodium lignin sulphonate 3 Precipitated silica 5 Montmorillonite to lû0 Y by weight ~2) Bifenox 30 1 h~.C.P.A. (sodium salt) 30 Sodium lauryl sulphate 2 Sodium lignin sulphonate 3 Precipitated siliw 5 Montmori!lonite to 100 In each ~xample, the active ingredients were carefully blended with the specified excipients in conventional mixing equipment. The blend was then further milled in a fluid energy mill to a size range of from I to 10 microns .
;~o The following emulsifiable concentrqtes were prepared having the constituents shown below:
by volume (3) Bifenox 20 M.C.P.B. (rnixed butyl esters) 3û
Calcium dodecylbenzene sulphonate 3 Alkyl phenoxypolyoxyethylene ethanols 4 Isophorone 30 Orthochlorotoluene to 100 , ,, ,':
~ .. : ~ . ~ . !
-' ' ' ' ~"'';~ .
~Z~6~j .
% by weight/
by volume
(4) Bifenox 20 Nl.C.P.A 20 Calcium dodecylbenzene sulphonate 3 Alkylphenoxypolyoxyethylene ethanols 4 Isophorone 30 : Orthochlorotoluene to 10û
The cctive ingredients were added to the appropriate solvent(s) with stirring and optional heating to facilitate dissolution of the active materials.The surfactants were then added. The solutions were then filtered to remove E~ insoluble impurities.
The following aqueous suspensions were prepared hcving the constituents shown below:
The cctive ingredients were added to the appropriate solvent(s) with stirring and optional heating to facilitate dissolution of the active materials.The surfactants were then added. The solutions were then filtered to remove E~ insoluble impurities.
The following aqueous suspensions were prepared hcving the constituents shown below:
(5) ,~o by weight Bifenox 30 M.C.P.A (amine salt~ 3û
; (Ethyl)hydroxyethyl cellulose û.2 Lignin sulphonate 3 Propylene glycol 2 Water to 100 .
.. . :
:, . . . .. . :
: . ~ . . .
.:
,. ~
; (Ethyl)hydroxyethyl cellulose û.2 Lignin sulphonate 3 Propylene glycol 2 Water to 100 .
.. . :
:, . . . .. . :
: . ~ . . .
.:
,. ~
6 Ei~
/~ by weight t~ Bifenox ~n M.C.P.B (amine salt) 35 Hydroxyethyl cellulose û.2 Amine ethoxylate 3 Wqter to lOû
The following Examples serve to illustrqte the synergistic effect demonstrated by the method of the invention Several field trials were carried out on winter wheat and one on spring barley on sandy and clay loam soils. Applications was made as tank mixtures with a knapsack sprayer at a volume of 3ûû-8ûO l/ha. The crop stage at application varied from the start of tillerir1g to the stage at which the secondnode was visible. Visual assessments of herbicidal activity were made from 2 to 15 weeks after application using the 8arratt and Horsfall (1945) rating system.
In the following table is set out the average of the results obtained in terms of percent control of the weed species Matricariq spp for the individual herbicides Bifenox, and M.C.P.A and for the tank mix combination of Bifenox +
M.C.P.A., there also being given the control value estimated by the Colby formula for additive effect..The concentrates from which the aqueous spray liquors were formed were Bifenox 8û% wettable power, and M.C.P.A 40~0 aqueous solution.
~: . ; , :
s TABLE
Yn fontro!
Dosage Rate Kg/ha Observed Colby formula Bifenox 1.0 16.1 N/A
Bifenox 1.5 25.5 N/A
Bifenox 2.0 4û.3 N/A
hl.C.P.A (amine salt) 0.8 38.5 N/A
M.C.l'.A.(amine salt) 1.6 64.8 N/A
E~ifenox + M.C.P.A.
(amine salt) 1.0 + 0.8 85.1 4804 " 1.5+0.8 93.4 54.2 " 2.0+ 1.6 95.3 79.û
Thus, from the above it can be seen that a genuine synergistic effect is observed when employing the method of the present invention.
Slight scorching of the crop was noted, which was subsequently out-grown.
As well as excellent control of the Matricaria spp, the following weed species were well controlled (greater than û0%) employing? in separate tests, the above combined tank mixes: Anethum ~raveolens9 Capsella bursa-pas~
Centaurea cyanus, Fumaria officinQlis, Lamium amplexicaule, Papaver rhoeas, Silene spp and Stellaria media.
Anagallis arven~, C od , Polygonum aviculare Ranunculus arvensis, Ranuncules repens, Raphanus r~phanistrum, Rumex crispus, Sinapis arvensis, Sonchus arvensis cnd Veronica hederifolia .
-The following greenhouse test was carried out to aSsess the efficac~, of bifenox combined with M.C.P.E~.
~ . .
.
: .
. ..
NIETHOD Seeds: Galium aparine ~ atricaria recutita Veronica persica Planting 0.5cm depth.(A/~atricaria sp light covering) Temperature/li,a,hting: Greenhouse (cool) Watering: when required Fertilisation- none Experiment design: randomised block (4 repl icates) Plot size treated 10 x 10cm pots Soi I texture: loam Application equipment: single nozzle microsprayer, 50cm band width, volume rate per area 50 ml per sq metre.
Weed Stage at Application: 3-5 true leaves In the following table is set out the average of the results obtained in terms of per cent control of the weed species together with the control ~ value estimated by the Colby formula. For the Veronica persica a visual control rating was made. For the other two species fresh weight of shoots was obtained. The bifenox from which the spray li~uorwas formed was an 80% wettable powder. the M.C.P.B. was a 48Y~ aqueous solution, the combination being a tank mix.
25~6~i5 WEED SPECIES % CONTROL
P~ate ~atricariaSp Galium Veronica kg/ha aparine persica Observed Colby Observed Colby Observed Colby Bifenox 0.75 56.5 N/A 62.5 N/A 77.0 N/A
M.C.P.B 1.0 7.5 N/A 0.0 N/A 73.0 N/A
M.C.P.B 1.5 2.4 N/A 0.0 N/A 78.0 N/A
Bifenox + MCPB 0.75+1.0 73.0 60.0 72.1 62.5 100.0 94.0 " 0.75+ I.S 82.0 57.5 78.3 62.5 100.0 96.0 Thus, from the above, it can be seen that a genuine synergistic effect is observed when employing the method of the present invention.
. ~ .
' ~ ' ' .;
/~ by weight t~ Bifenox ~n M.C.P.B (amine salt) 35 Hydroxyethyl cellulose û.2 Amine ethoxylate 3 Wqter to lOû
The following Examples serve to illustrqte the synergistic effect demonstrated by the method of the invention Several field trials were carried out on winter wheat and one on spring barley on sandy and clay loam soils. Applications was made as tank mixtures with a knapsack sprayer at a volume of 3ûû-8ûO l/ha. The crop stage at application varied from the start of tillerir1g to the stage at which the secondnode was visible. Visual assessments of herbicidal activity were made from 2 to 15 weeks after application using the 8arratt and Horsfall (1945) rating system.
In the following table is set out the average of the results obtained in terms of percent control of the weed species Matricariq spp for the individual herbicides Bifenox, and M.C.P.A and for the tank mix combination of Bifenox +
M.C.P.A., there also being given the control value estimated by the Colby formula for additive effect..The concentrates from which the aqueous spray liquors were formed were Bifenox 8û% wettable power, and M.C.P.A 40~0 aqueous solution.
~: . ; , :
s TABLE
Yn fontro!
Dosage Rate Kg/ha Observed Colby formula Bifenox 1.0 16.1 N/A
Bifenox 1.5 25.5 N/A
Bifenox 2.0 4û.3 N/A
hl.C.P.A (amine salt) 0.8 38.5 N/A
M.C.l'.A.(amine salt) 1.6 64.8 N/A
E~ifenox + M.C.P.A.
(amine salt) 1.0 + 0.8 85.1 4804 " 1.5+0.8 93.4 54.2 " 2.0+ 1.6 95.3 79.û
Thus, from the above it can be seen that a genuine synergistic effect is observed when employing the method of the present invention.
Slight scorching of the crop was noted, which was subsequently out-grown.
As well as excellent control of the Matricaria spp, the following weed species were well controlled (greater than û0%) employing? in separate tests, the above combined tank mixes: Anethum ~raveolens9 Capsella bursa-pas~
Centaurea cyanus, Fumaria officinQlis, Lamium amplexicaule, Papaver rhoeas, Silene spp and Stellaria media.
Anagallis arven~, C od , Polygonum aviculare Ranunculus arvensis, Ranuncules repens, Raphanus r~phanistrum, Rumex crispus, Sinapis arvensis, Sonchus arvensis cnd Veronica hederifolia .
-The following greenhouse test was carried out to aSsess the efficac~, of bifenox combined with M.C.P.E~.
~ . .
.
: .
. ..
NIETHOD Seeds: Galium aparine ~ atricaria recutita Veronica persica Planting 0.5cm depth.(A/~atricaria sp light covering) Temperature/li,a,hting: Greenhouse (cool) Watering: when required Fertilisation- none Experiment design: randomised block (4 repl icates) Plot size treated 10 x 10cm pots Soi I texture: loam Application equipment: single nozzle microsprayer, 50cm band width, volume rate per area 50 ml per sq metre.
Weed Stage at Application: 3-5 true leaves In the following table is set out the average of the results obtained in terms of per cent control of the weed species together with the control ~ value estimated by the Colby formula. For the Veronica persica a visual control rating was made. For the other two species fresh weight of shoots was obtained. The bifenox from which the spray li~uorwas formed was an 80% wettable powder. the M.C.P.B. was a 48Y~ aqueous solution, the combination being a tank mix.
25~6~i5 WEED SPECIES % CONTROL
P~ate ~atricariaSp Galium Veronica kg/ha aparine persica Observed Colby Observed Colby Observed Colby Bifenox 0.75 56.5 N/A 62.5 N/A 77.0 N/A
M.C.P.B 1.0 7.5 N/A 0.0 N/A 73.0 N/A
M.C.P.B 1.5 2.4 N/A 0.0 N/A 78.0 N/A
Bifenox + MCPB 0.75+1.0 73.0 60.0 72.1 62.5 100.0 94.0 " 0.75+ I.S 82.0 57.5 78.3 62.5 100.0 96.0 Thus, from the above, it can be seen that a genuine synergistic effect is observed when employing the method of the present invention.
. ~ .
' ~ ' ' .;
Claims (16)
1. A method of combating broadleaf weeds in a cereal crop locus comprising applying to said locus, post emergence the crop, a compound of formula I, (I) and one or more compounds of formula II
(II) wherein X is - CH2- or -(CH2)3-, said compound of formula II being optionally in a salt or ester form which is non-phytotoxic to cereal crops; where a compound of formula II, in which X is -CH2- is employed, the compound of formula I being applied at a rate of 0.7 to 2.0 kg/ha and the compound of formula II being applied at a rate of 0.7 to 3.0 Kg/hs, and where a compound of formula II, wherein X is -(CH2)3-, is employed the compound of formua I being applied at a rate of 0.25 to 3.0 kg/ha and the compound of formua II being applied at a rate of 0.1 to 3.5 kg/ha.
(II) wherein X is - CH2- or -(CH2)3-, said compound of formula II being optionally in a salt or ester form which is non-phytotoxic to cereal crops; where a compound of formula II, in which X is -CH2- is employed, the compound of formula I being applied at a rate of 0.7 to 2.0 kg/ha and the compound of formula II being applied at a rate of 0.7 to 3.0 Kg/hs, and where a compound of formula II, wherein X is -(CH2)3-, is employed the compound of formua I being applied at a rate of 0.25 to 3.0 kg/ha and the compound of formua II being applied at a rate of 0.1 to 3.5 kg/ha.
2. A method according to claim 1, wherein the compound of formula I is applied at a rate of 0.7 to 2.0 kg/ha and the compound(s) of formula II at a rate of 0.7 to 3.0 kg/ha.
3. A method according to claim 1, wherein the compound of formula I is applied at a rate of from 0.7 to 1.5 kg/ha.
4. A method of claim 3, wherein the compound of formula I is applied at a rate of from 0.75 to 1.0 kg/ha.
5. A method of claim 1, wherein, in the compound of formula II, X is II, x is -(CH2)-.
6. A method according to claim 5 wherein the compound of formula II is applied at a rate of 0.7 to 1.5 kg/ha.
7. A method according to claim 6, wherein the compound of formula II
is applied at a rate of from 0.75 to 1.0 kg/ha.
is applied at a rate of from 0.75 to 1.0 kg/ha.
8. A method according to claim 1, wherein, in the compound of formula II, X is -(CH2)3-.
9. A method according to claim 8, wherein the compound of formula II
is applied at a rate of from 1.0 to 2.0 kg/ha.
is applied at a rate of from 1.0 to 2.0 kg/ha.
10. A method according to claim 8, wherein the weight ratio of the compound of formula I to the compound of formula II is in the range of 1:3 to 1.5:1.
11. A method according to claim 5, wherein the weight ratio of the compound of formula I to the compound of formula II is in the range of 1:2 to 2:1.
12. A method according to claim 1, wherein the crop is a winter wheat, spring barley or winter barley crop.
13. A method according to claim 1, wherein the compound of formula I is in a salt or ester form non-phytotoxic to cereal crops.
14. A herbicidal composition comprising a compound of formula I, stated in claim 1, and a compound of formula II, stated in claim 1, to be used at the rates and in the crops stated in claim 1, the weight ratio of the compound of formula I to the compound of formula II being in the range of 1:4 to 3:1.
15. A composition according to claim 14 in the form of an aqueous suspension or a wettable powder.
16. A herbicidal composition comprising a compound of formula I, stated in claim 1, together with a compound of formula II, stated in claim 1, in which X is -(CH2)3-, the weight ratio of the compound of formula I to the compound of formula II being in the range of from 1:4 to 3:1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7849440 | 1978-12-21 | ||
| GB49440/78 | 1978-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129665A true CA1129665A (en) | 1982-08-17 |
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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA342,403A Expired CA1131036A (en) | 1978-12-21 | 1979-12-20 | Herbicidal treatments and formulations |
Country Status (24)
| Country | Link |
|---|---|
| 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) |
| RO (1) | RO78398A (en) |
| SG (1) | SG44385G (en) |
| TR (1) | TR20965A (en) |
Families Citing this family (6)
| 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 |
| AU612347B2 (en) * | 1987-02-24 | 1991-07-11 | Rhone-Poulenc Agrochimie | Herbicidal composition and method |
| 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 |
| JPS562527B2 (en) * | 1973-08-20 | 1981-01-20 | ||
| 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 |
| 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 |
| 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 IL IL58962A patent/IL58962A0/en unknown
- 1979-12-14 MX MX798559U patent/MX6293E/en unknown
- 1979-12-15 MA MA18880A patent/MA18678A1/en unknown
- 1979-12-15 DE DE19792950682 patent/DE2950682A1/en not_active Withdrawn
- 1979-12-17 GB GB7943358A patent/GB2042339B/en not_active Expired
- 1979-12-17 CH CH1114279A patent/CH641932A5/en not_active IP Right Cessation
- 1979-12-17 NZ NZ192415A patent/NZ192415A/en unknown
- 1979-12-17 RO RO7999570A patent/RO78398A/en unknown
- 1979-12-18 NL NL7909099A patent/NL7909099A/en active Search and Examination
- 1979-12-18 FR FR7930949A patent/FR2444407A1/en active Granted
- 1979-12-19 BR BR7908349A patent/BR7908349A/en unknown
- 1979-12-19 PL PL22052879A patent/PL220528A1/xx unknown
- 1979-12-20 JP JP16626679A patent/JPS5589204A/en active Pending
- 1979-12-20 NO NO794206A patent/NO794206L/en unknown
- 1979-12-20 CA CA342,403A patent/CA1131036A/en not_active Expired
- 1979-12-20 DD DD79217958A patent/DD147993A5/en unknown
- 1979-12-20 BE BE6/47042A patent/BE880782A/en not_active IP Right Cessation
- 1979-12-20 LU LU82017A patent/LU82017A1/en unknown
- 1979-12-20 IE IE2488/79A patent/IE49337B1/en not_active IP Right Cessation
- 1979-12-20 IT IT51151/79A patent/IT1162429B/en active
- 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 JP1028521A patent/JPH01308208A/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 JP1028520A patent/JPH01308207A/en active Pending
- 1989-02-07 JP JP1028523A patent/JPH01287003A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2042339B (en) | 1982-10-20 |
| GB2042339A (en) | 1980-09-24 |
| BE880782A (en) | 1980-06-20 |
| HK73985A (en) | 1985-10-04 |
| DD147993A5 (en) | 1981-05-06 |
| RO78398A (en) | 1982-02-26 |
| TR20965A (en) | 1983-03-07 |
| NZ192415A (en) | 1982-03-30 |
| IE49337B1 (en) | 1985-09-18 |
| DE2950682A1 (en) | 1980-07-17 |
| IT7951151A0 (en) | 1979-12-20 |
| MX6293E (en) | 1985-03-18 |
| BR7908349A (en) | 1980-09-23 |
| JPH01287003A (en) | 1989-11-17 |
| IL58962A0 (en) | 1980-03-31 |
| IT1162429B (en) | 1987-04-01 |
| LU82017A1 (en) | 1981-07-23 |
| CA1131036A (en) | 1982-09-07 |
| NO794206L (en) | 1980-06-24 |
| JPS5589204A (en) | 1980-07-05 |
| JO985B1 (en) | 1979-12-01 |
| JPH01308208A (en) | 1989-12-12 |
| FR2444407B1 (en) | 1984-09-28 |
| MA18678A1 (en) | 1980-07-01 |
| JPH01308209A (en) | 1989-12-12 |
| JPH01287004A (en) | 1989-11-17 |
| NL7909099A (en) | 1980-06-24 |
| SG44385G (en) | 1986-01-17 |
| JPH01308207A (en) | 1989-12-12 |
| FR2444407A1 (en) | 1980-07-18 |
| IE792488L (en) | 1980-06-21 |
| PL220528A1 (en) | 1980-09-22 |
| CH641932A5 (en) | 1984-03-30 |
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