GB2190293A - Herbicidal composition - Google Patents

Herbicidal composition Download PDF

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Publication number
GB2190293A
GB2190293A GB08711097A GB8711097A GB2190293A GB 2190293 A GB2190293 A GB 2190293A GB 08711097 A GB08711097 A GB 08711097A GB 8711097 A GB8711097 A GB 8711097A GB 2190293 A GB2190293 A GB 2190293A
Authority
GB
United Kingdom
Prior art keywords
herbicidal composition
herbicidal
phenoxy
composition
phenoxy alkanoic
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.)
Granted
Application number
GB08711097A
Other versions
GB8711097D0 (en
GB2190293B (en
Inventor
Wallace Crawshaw
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
J D Campbell & Sons Ltd
Original Assignee
J D Campbell & Sons Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB868611445A external-priority patent/GB8611445D0/en
Application filed by J D Campbell & Sons Ltd filed Critical J D Campbell & Sons Ltd
Priority to GB8711097A priority Critical patent/GB2190293B/en
Publication of GB8711097D0 publication Critical patent/GB8711097D0/en
Publication of GB2190293A publication Critical patent/GB2190293A/en
Application granted granted Critical
Publication of GB2190293B publication Critical patent/GB2190293B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • A01N43/72—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
    • 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
    • A01N43/88—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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

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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)

Abstract

A herbicidal composition comprising a herbicidal diester formally derived from one mole of a diol esterified with one mole of a first phenoxy alkanoic acid and with one mole of a second phenoxy alkanoic acid, and at least one additional herbicidal compound which is not based on a phenoxy alkanoic acid. A preferred composition comprises a diester formed from ethylene glycol and MCPA and 2,4-DB together with Linuron.

Description

SPECIFICATION Herbicidal compositions The present invention relates to herbicidal compositions.
Our co-pending U.K. Patent Application No. 86 23939 (GB-A-2185015) proposes herbicidal diesters formally derived from one mole of a diol esterified one mole of a first phenoxy alknoic acid and with one mole of a second phenoxy alknoic acid (different from the first said acid).
The diester of GB-A-2185015 may be prepared by esterifying a mixture of the phenoxy alkanoic acids with the diol such that the product obtained comprises the "mixed" diester as well as the bisesters of the two phenoxy alkanoic acids. Such an admixture of esters may be used in the herbicidal formulations proposed in GB-A-2185015.
According to the present invention there is now provided a herbicidal composition which comprises a herbicidal diester as proposed in the above Patent Application and at least one additional herbicidal compound which is not based on a phenoxy alknoic acid.
Preferably the additional herbicidal compound is selected from Dicamba, Dinoseb, Linuron, Bentazone and Benzolin, most preferably Linuron.
Preferably the phenoxy alkanoic acids from which the herbicidal diesters are derived are selected from the following compounds (I)
in which R is lower alkyl (particularly C1-4), e.g. methyl) or Cl, R1 is H or lower alkyl (particularly C1-4, e.g. methyl) and n is 0-3.
Specific examples of such acids are listed below.
2,4-D (R=CI; R,=H; n=O) 2,4DP (R=CI; R,=Me; n=O CMPP (R=Me; R,=Me; n=O MCPA (R=Me; R,=H; n=O 2,4-DB (R=CI; R,=H; n=2) MCPB (R=Me; R,=H; n=2) The diols used to produce the diesters are preferably selected from ethylene glycol, and propylene glycol.
Thus the preferred diesters of the invention are of the general formula (II)
in which R2 is H or methyl R, R, and n are as defined above, R', R,' and n' are selected from the same group as R, R, and n respectively with the proviso that the two acid residues in the molecule are not the same.
The most preferred formulations in accordance with the invention comprise (a) a mixed diester derived from ethylene glycol, 2,4-DB, and MCPA, (possibly in admixture with the bisesters derived from each of the two phenoxy alkanoic acids) and (b) Linuron.
Preferably the weight ratio of the additional herbicide (e.g. Linuron) to the total amount of phenoxy alkanoic ester(s) is 1:250 to 250:1, preferably 1:100 to 100:1, more preferably 1:10 to 10:1.
The compositions may be applied to the land such that the additional herbidide (e.g. Linuron) is applied in an amount of 5-300 (preferably 50-200) grammes per hectare and the phenoxy alkanoic ester(s) is applied in a total amount of 50-6000 (preferably 500-2500) grammes per hectare.
The herbicidal compositions of this invention may of course be formulated with conventional carriers, surfactants, solvents etc.
The compositions of this invention are particularly suitable for the control of broad leafed weeds (e.g. common chickweed) in undersown cereals.
The invention is illustrated by the following Example.
Example A non-volatile ester as proposed in GB-A-2185015 was prepared from the following reactants: 2209 2,4 dichlorophenoxy butyric acid 309 2-methyl-4-chlorophenoxy acetic acid 349 ethylene glycol 200mix xylene This mixture was heated to reflux and water azeotroped off until esterification was complete.
The xylene was then distilled off under a vacuum of 5mm to a boiler temperature of 1900C.
The product was a brown liquid which solidifies on standing over a few weeks to give a low melting solid of the following composition: 1- 2% mono MCPA ethylene glycol ester 4- 6% mono 2,4-DB ethylene glycol ester 2- 3% bis MCPA ethylene glycol ester 19-20% MCPA/DB ethylene glycol ester 68-729b bis 2,4-DB ethylene glycol ester An emulsifible concentrate can be prepared from 2809 of the above ester mixture, 319 of Linuron (97%), 359 of Calcium Dodecyl benzene sulphonate, 709 alkylphenol ethoxylates and 660my of high boiling aromatic solvent.

Claims (14)

1. A herbicidal composition which comprises a herbicidal diester formally derived from one mole of a diol esterified with one mole of a first phenoxy alkanoic acid and with one mole of a second phenoxy alkanoic acid, and at least one additional herbicidal compound which is not based on a phenoxy alkanoic acid.
2. A herbicidal composition as claimed in claim 1 wherein the herbicidal diester is of the general formula II
where R2 is H or methyl R and R' are lower alkyl or Cl, R, and R,' are H or lower alkyl, and n and n' are 0-3 with the proviso that the two acid residues in the molecule are not the same.
3. Herbicidal composition as claimed in claim 2 wherein one phenoxy alkanoic residue is derived from MCPA (R=Me, R1=H, n=0) and the other is derived from 2,4-DB (R'=CI, R,'=H, no=2).
4. A herbicidal composition as claimed in any one of claims 1 to 3 wherein the additional herbicide is selected from Dicamba, Dinoseb, Linuron and Benazolin.
5. A herbicidal composition as claimed in claim 4 wherein the additional herbicide is Linuron.
6. A herbicidal composition as claimed in any one of claims 1 to 5 wherein the weight ratio of the additional herbicide to the total amount of phenoxy alkanoic esters is 1:250 to 250:1.
7. A herbicidal composition as claimed in claim 6 wherein the weight ratio is 1:100 to 100:1.
8. A herbicidal composition as claimed in claim 7 wherein the weight ratio is 1:10 to 10:1.
9. A herbicidal composition as claimed in any one of claims 1 to 8 which is formulated with a solvent and/or carrier and/or surfactant.
10. A herbicidal composition substantially as hereinbefore described with reference to the foregoing Example.
11. A method of combatting weeds comprising applying to an area of land to be treated a herbicidally effective amount of a composition as claimed in any one of claims 1 to 10.
12. A method as claimed in claim 11 wherein the application rate of the composition to the land is 5-300 grammes per hectare of the additional herbicide and 50-6000 grammes per hectare of the phenoxy alkanoic esters.
13. A method as claimed in claim 12 wherein the additional herbicide is applied at a rate of 50-200 grammes per hectare and the phenoxy aklanoic ester is applied at a rate of 500-2000 grammes per hectare.
14. A method of combatting weeds substantially as hereinbefore described.
GB8711097A 1986-05-10 1987-05-11 Herbicidal compositions containing phenoxy alkanoic esters Expired - Fee Related GB2190293B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB8711097A GB2190293B (en) 1986-05-10 1987-05-11 Herbicidal compositions containing phenoxy alkanoic esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB868611445A GB8611445D0 (en) 1986-05-10 1986-05-10 Herbicidal compositions
GB8711097A GB2190293B (en) 1986-05-10 1987-05-11 Herbicidal compositions containing phenoxy alkanoic esters

Publications (3)

Publication Number Publication Date
GB8711097D0 GB8711097D0 (en) 1987-06-17
GB2190293A true GB2190293A (en) 1987-11-18
GB2190293B GB2190293B (en) 1990-12-19

Family

ID=26290748

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8711097A Expired - Fee Related GB2190293B (en) 1986-05-10 1987-05-11 Herbicidal compositions containing phenoxy alkanoic esters

Country Status (1)

Country Link
GB (1) GB2190293B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2103234A1 (en) * 1995-03-09 1997-09-01 Agrides S A A herbicidal product with pre- and post-emergence action.
EP3135113A1 (en) * 2015-08-31 2017-03-01 Basf Se Use of herbicidal compositions for controlling unwanted vegetation
US10477863B2 (en) 2015-08-06 2019-11-19 Basf Se Use of herbicidal compositions for controlling unwanted vegetation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1405590A (en) * 1971-11-19 1975-09-10 Fisons Ltd Herbicide
GB1453772A (en) * 1973-08-31 1976-10-27 Hoechst Ag Herbicidal compositions
GB1494532A (en) * 1975-06-04 1977-12-07 Dow Chemical Co Herbicidal compositions
GB1593167A (en) * 1976-12-18 1981-07-15 Hoechst Ag Herbicidal mixtures and compsitioms
GB2115283A (en) * 1982-02-11 1983-09-07 Albright & Wilson Herbicidal composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2185015B (en) * 1985-10-04 1990-07-11 J D Campbell & Sons Limited Herbicidal esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1405590A (en) * 1971-11-19 1975-09-10 Fisons Ltd Herbicide
GB1453772A (en) * 1973-08-31 1976-10-27 Hoechst Ag Herbicidal compositions
GB1494532A (en) * 1975-06-04 1977-12-07 Dow Chemical Co Herbicidal compositions
GB1593167A (en) * 1976-12-18 1981-07-15 Hoechst Ag Herbicidal mixtures and compsitioms
GB2115283A (en) * 1982-02-11 1983-09-07 Albright & Wilson Herbicidal composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2103234A1 (en) * 1995-03-09 1997-09-01 Agrides S A A herbicidal product with pre- and post-emergence action.
US10477863B2 (en) 2015-08-06 2019-11-19 Basf Se Use of herbicidal compositions for controlling unwanted vegetation
EP3135113A1 (en) * 2015-08-31 2017-03-01 Basf Se Use of herbicidal compositions for controlling unwanted vegetation

Also Published As

Publication number Publication date
GB8711097D0 (en) 1987-06-17
GB2190293B (en) 1990-12-19

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Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19960511