GB823208A - New herbicidal compounds - Google Patents
New herbicidal compoundsInfo
- Publication number
- GB823208A GB823208A GB1711755A GB1711755A GB823208A GB 823208 A GB823208 A GB 823208A GB 1711755 A GB1711755 A GB 1711755A GB 1711755 A GB1711755 A GB 1711755A GB 823208 A GB823208 A GB 823208A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- chloro
- dichloro
- acid
- ester
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 230000002363 herbicidal effect Effects 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 5
- 150000001408 amides Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 230000008635 plant growth Effects 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 abstract 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 abstract 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 1
- WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 abstract 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- MGDNLGRMXPBCOR-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;dodecanoate Chemical compound OCCNCCO.CCCCCCCCCCCC(O)=O MGDNLGRMXPBCOR-UHFFFAOYSA-N 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 150000001989 diazonium salts Chemical group 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002780 morpholines Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229960004418 trolamine Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a number of specified halo-methyl-alpha-phenoxypropionic acids, substituted as follows: 3-chloro-2-methyl-, 2-chloro - 3 - methyl-, 2 - chloro - 5 - methyl, 2 : 4 - dichloro - 3 - methyl-, 4 : 5 - dichloro - 2 - methyl-, 2 : 4 - dichloro - 5 - methyl-, 3 : 5 - di chloro - 2 - methyl-, and their esters, salts and amides; the preparation of all the above compounds by the condensation of the appropriately substituted phenol with an ester or other suitable derivative of an alpha-chloro- or bromopropionic acid, followed, if desired, by conversion of the product to the free acid or a salt or amide thereof; and plant-growth compositions containing the products (see Group VI). In an example, 3-chloro-o-cresol condenses with ethyl a -bromo-propionate to give, on hydrolysis, a -(3-chloro-2-methylphenoxy) propionic acid; other products of the above list are obtained similarly; the acids may be esterified with benzyl alcohol, ethyl hexanol and other alcohols, and 2-(2 : 4-dichlorophenoxy) ethyl bromide and 3-(2 : 4-dichlorophenoxy)-propyl bromide as examples. Esters with monoethers of ethylene glycol and similar products are also specified. The preparation of certain amides from the corresponding acid via the acid chloride, or from an ester, is also exemplified. The second Provisional Specification comprises generally compounds in which the phenyl group contains one methyl and two chlorine substituents. p Starting material. 3 : 5 - Dichloro - 2 - methylphenol is obtained from 2 : 4-dichloro-6-nitrotoluene by reduction, diazotization, and decomposition of the diazonium compound.ALSO:Herbicidal and plant growth regulant compositions contain, in admixture with a diluent or carrier, an a -phenoxypropionic acid, or salt, ester or amide thereof, substituted as follows: 3 - chloro - 2 - methyl -, 2 - chloro - 3 - or 5 - methyl-, 2 : 4-dichloro-3- or 5-methyl-, or 4 : 5- or 3 : 5-dichloro-2-methyl-. The compositions may take the form of dusts, aqueous solutions or dispersions, oil-in-water emulsions, or concentrates to be diluted before use. Examples of the last comprise aqueous solutions, containing an octylphenyl-ethylene oxide condensate as wetting agent, of the sodium and diethanolamine salts of the 3-chloro-2-methyl-acid and of the ammonium, mono-, di- and tri-ethanolamine, diethylamine and morpholine salts of the 2 : 4-dichloro-3-methyl-acid, and an aqueous emulsion of a solution of the ethyl ester of the 3-chloro-2-methyl- or 2 : 4-dichloro-3-methyl-acid in a mixture of xylene and an emulsifying agent consisting of lauric diethanolamine and an octylphenol-ethylene oxide condensate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1711755A GB823208A (en) | 1955-06-14 | 1955-06-14 | New herbicidal compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1711755A GB823208A (en) | 1955-06-14 | 1955-06-14 | New herbicidal compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823208A true GB823208A (en) | 1959-11-11 |
Family
ID=10089565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1711755A Expired GB823208A (en) | 1955-06-14 | 1955-06-14 | New herbicidal compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB823208A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1229065B (en) * | 1961-11-06 | 1966-11-24 | Jean Claude Rouge | Process for the preparation of fine-grained amorphous amides from optionally substituted chlorophenoxycarboxylic acids |
| US3439018A (en) * | 1963-09-30 | 1969-04-15 | Boots Pure Drug Co Ltd | Alpha-(4-chloro-2-methylphenoxy) propionanilides |
| JPS5547640A (en) * | 1978-08-28 | 1980-04-04 | Ppg Industries Inc | Trichlorophenoxyalkanoic acid containing no chlorinated dibenzooppdioxine |
-
1955
- 1955-06-14 GB GB1711755A patent/GB823208A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1229065B (en) * | 1961-11-06 | 1966-11-24 | Jean Claude Rouge | Process for the preparation of fine-grained amorphous amides from optionally substituted chlorophenoxycarboxylic acids |
| US3439018A (en) * | 1963-09-30 | 1969-04-15 | Boots Pure Drug Co Ltd | Alpha-(4-chloro-2-methylphenoxy) propionanilides |
| JPS5547640A (en) * | 1978-08-28 | 1980-04-04 | Ppg Industries Inc | Trichlorophenoxyalkanoic acid containing no chlorinated dibenzooppdioxine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB901553A (en) | New compounds having herbicidal activities and process of making same | |
| GB930296A (en) | The preparation of acylamino compounds | |
| GB893234A (en) | Phosphonic acid esters | |
| GB823208A (en) | New herbicidal compounds | |
| IL54665A (en) | Preparation for substituted benzyl esters of 2,2-dimethyl-3-(2,2-disubstituted vinyl)cyclopropane carboxylic acids and insecticical compsitions containing them | |
| US2787633A (en) | Acceleration of fatty amine addition reactions | |
| GB909372A (en) | Selective herbicides and process for their manufacture | |
| US3031501A (en) | Preparation of 2, 5-diarylamino-tereph-thalic acid and salts thereof | |
| GB924762A (en) | New derivatives of 1,4-bis-styryl-benzene and optical brightening therewith | |
| JPS5616475A (en) | Quinoxaline derivative and herbicide containing the same as effective component | |
| GB988074A (en) | Herbicidal compositions containing hormone weedkillers | |
| GB640109A (en) | Photographic elements containing urethanes of n-substituted j acids as color formers | |
| GB820180A (en) | New salts of alpha-(4-chloro-2-methylphenoxy)-propionic acid and herbicidal compositions containing them | |
| GB843883A (en) | New aromatic ethers | |
| ES8604579A1 (en) | A PROCEDURE TO PREPARE A NEW ZABICICLE (3.3.1) -NONANO | |
| GB998656A (en) | Process for the manufacture of ortho-aminophenol-ª‰-hydroxyethyl-sulphone sulphuric acid esters | |
| GB1005238A (en) | New pyrazolone compounds and processes for their preparation | |
| GB808106A (en) | -a-(4-chloro-2:3 or 2:5-dimethyl-phenoxy) propionic acid and herbicidal compositionscontaining it | |
| GB485377A (en) | Improvements in the manufacture and production of aminoketones | |
| GB706440A (en) | Improvements in or relating to trichloroacetic acid, esters of trichloroacetic acid and salts of trichloroacetic acid | |
| GB833218A (en) | Preparation of 2, 3, 5, 6-tetrachlorobenzoyl halides and their derivatives, particularly for the production of herbicidal compositions | |
| GB598484A (en) | Compositions of matter for use in killing weeds | |
| GB864720A (en) | A process for the production of 3,5-dihydrocarbonsubstituted-4-hydroxy benzoic acids and their esters | |
| GB720826A (en) | Improvements in or relating to substituted thiobarbituric acids and their salts and process of preparing the same | |
| GB924349A (en) | Herbicidal compositions containing dipyridylium quaternary salts |