GB2190293A - Herbicidal composition - Google Patents
Herbicidal composition Download PDFInfo
- 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
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000005690 diesters Chemical class 0.000 claims abstract description 12
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005573 Linuron Substances 0.000 claims abstract description 9
- 239000005574 MCPA Substances 0.000 claims abstract description 8
- 239000002794 2,4-DB Substances 0.000 claims abstract description 6
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims abstract description 6
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 150000002009 diols Chemical class 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical group COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 claims 1
- 229960002939 metizoline Drugs 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 22
- -1 MCPA ethylene glycol ester Chemical class 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- 229960002312 tolazoline Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- 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.
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)
| 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)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2185015B (en) * | 1985-10-04 | 1990-07-11 | J D Campbell & Sons Limited | Herbicidal esters |
-
1987
- 1987-05-11 GB GB8711097A patent/GB2190293B/en not_active Expired - Fee Related
Patent Citations (5)
| 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)
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960511 |