CA1103270A - Higher halophenoxy benzoic acid esters - Google Patents
Higher halophenoxy benzoic acid estersInfo
- Publication number
- CA1103270A CA1103270A CA227,557A CA227557A CA1103270A CA 1103270 A CA1103270 A CA 1103270A CA 227557 A CA227557 A CA 227557A CA 1103270 A CA1103270 A CA 1103270A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dichlorophenoxy
- nitrobenzoate
- nitro
- oil
- 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
- 150000001558 benzoic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- -1 3-Butyn-2-yl Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 4
- XRNGYLWNKHEIFB-UHFFFAOYSA-N but-3-yn-2-yl 5-(2,4-dichloro-6-fluorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C#C)=CC(OC=2C(=CC(Cl)=CC=2F)Cl)=C1 XRNGYLWNKHEIFB-UHFFFAOYSA-N 0.000 claims description 3
- BGIKZJURPXCKTD-UHFFFAOYSA-N cyclohexyl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate Chemical compound C1=C(C(=O)OC2CCCCC2)C([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl BGIKZJURPXCKTD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- JSGYQNAGJCFNIR-UHFFFAOYSA-N octan-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)CCCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 JSGYQNAGJCFNIR-UHFFFAOYSA-N 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 2
- CHISELFNYSMPKZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)(C)C#C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 CHISELFNYSMPKZ-UHFFFAOYSA-N 0.000 claims 2
- NUBRDNKMTMATQV-UHFFFAOYSA-N cyclohexyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C(C(=O)OC2CCCCC2)C([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl NUBRDNKMTMATQV-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- DPINWNNJFYNDDE-UHFFFAOYSA-N but-3-yn-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C#C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DPINWNNJFYNDDE-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 8
- 239000004009 herbicide Substances 0.000 abstract description 7
- 235000010233 benzoic acid Nutrition 0.000 abstract description 2
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- IUSYSZLVZMUVDO-UHFFFAOYSA-N 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 IUSYSZLVZMUVDO-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- ZTDSOTUGZCBMMB-UHFFFAOYSA-N 2-methylpropyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(C)C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 ZTDSOTUGZCBMMB-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- AZIPXXGCTIHUDY-UHFFFAOYSA-N 3-methylbutyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCC(C)C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 AZIPXXGCTIHUDY-UHFFFAOYSA-N 0.000 description 1
- UYHJDXSRZUCSNA-UHFFFAOYSA-N 5-(2,4-dichlorophenoxy)-2-nitrobenzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl UYHJDXSRZUCSNA-UHFFFAOYSA-N 0.000 description 1
- 101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000220243 Brassica sp. Species 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000160765 Erebia ligea Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 description 1
- OXHVHZRGKJEMFO-UHFFFAOYSA-N butyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 OXHVHZRGKJEMFO-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- COHBVAXDFGNNBA-UHFFFAOYSA-N cyclohexyl 5-(2,4-dichloro-6-fluorophenoxy)-2-nitrobenzoate Chemical compound C1=C(C(=O)OC2CCCCC2)C([N+](=O)[O-])=CC=C1OC1=C(F)C=C(Cl)C=C1Cl COHBVAXDFGNNBA-UHFFFAOYSA-N 0.000 description 1
- RSKJHRNJPWRXNW-UHFFFAOYSA-N decan-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)CCCCCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 RSKJHRNJPWRXNW-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- MUSBIVDDCNKCDH-UHFFFAOYSA-N dodecyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCCCCCCCCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 MUSBIVDDCNKCDH-UHFFFAOYSA-N 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- IGJBAMLROGRBLH-UHFFFAOYSA-N heptan-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)CCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 IGJBAMLROGRBLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RLPMQLBYZITAGM-UHFFFAOYSA-N oct-1-yn-3-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(CCCCC)C#C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 RLPMQLBYZITAGM-UHFFFAOYSA-N 0.000 description 1
- BKLICPGZXDNACE-UHFFFAOYSA-N octyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCCCCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 BKLICPGZXDNACE-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FURLEXVKGJUCFJ-UHFFFAOYSA-N pentyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCCCC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 FURLEXVKGJUCFJ-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- AQMHGHYGFOLTMP-UHFFFAOYSA-N prop-1-en-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(=C)C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 AQMHGHYGFOLTMP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000021217 seedling development Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GVRKPCZXJMLEDI-UHFFFAOYSA-N tert-butyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)(C)C)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 GVRKPCZXJMLEDI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US477233A US3907866A (en) | 1974-06-07 | 1974-06-07 | Higher halophenoxy benzoic acid esters |
| US477233 | 1974-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1103270A true CA1103270A (en) | 1981-06-16 |
Family
ID=23895075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,557A Expired CA1103270A (en) | 1974-06-07 | 1975-05-22 | Higher halophenoxy benzoic acid esters |
Country Status (13)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32243E (en) * | 1969-04-25 | 1986-09-09 | Rhone-Poulenc Agrochimie | Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| USRE32216E (en) * | 1969-04-25 | 1986-07-29 | Rhone-Poulenc Agrochimie | Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| US4164409A (en) * | 1971-02-11 | 1979-08-14 | Mobil Oil Corp. | Substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| US4164410A (en) * | 1971-02-11 | 1979-08-14 | Mobil Oil Corp. | Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| US4164408A (en) * | 1971-02-11 | 1979-08-14 | Mobil Oil Corp. | Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| USRE32215E (en) * | 1971-02-11 | 1986-07-22 | Rhone-Poulenc Agrochimie | Substituted phenoxybenzoic acids compositions of the same and herbicidal use thereof |
| US4681622A (en) * | 1973-09-19 | 1987-07-21 | Rhone-Poulenc Agrochimie | Substituted phenoxybenzoic acids and derivatives thereof as herbicides |
| CH588210A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-07-15 | 1977-05-31 | Ciba Geigy Ag | |
| US4401828A (en) * | 1978-08-04 | 1983-08-30 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| US4344789A (en) * | 1979-05-11 | 1982-08-17 | Ppg Industries, Inc. | Acids and esters of 5-(2-optionally substituted-4-trifluoromethyl-6-optionally substituted phenoxy)-2-nitro, -halo, or-cyano alpha substituted phenyl carboxy oximes, and method of controlling weeds with them |
| US4263227A (en) * | 1979-05-14 | 1981-04-21 | Ppg Industries, Inc. | 5-(2-Chloro-4-trifluoromethyl)-, or (4-trifluoromethyl or 2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-substituted carbonyl oxime-O-alkyl ethers |
| US4375981A (en) * | 1979-05-14 | 1983-03-08 | Ppg Industries, Inc. | Method for controlling weed growth using herbicidally 5-(2-chloro-4-trifluoromethyl)-, or (4-trifluoromethyl or 2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-substituted carbonyl oxime-O-alkyl ethers |
| DK155935C (da) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | Substituerede diphenylethere, herbicide praeparater indeholdende disse forbindelser samt fremgangsmaade til bekaempelse af ukrudt |
| DE2967368D1 (en) * | 1979-11-02 | 1985-03-07 | Rohm & Haas | Substituted diphenyl ethers, herbicidal compositions containing them and method of combating weeds |
| US4551171A (en) * | 1980-02-01 | 1985-11-05 | Rhone-Poulenc, Inc. | 2-Nitro-5-(substituted-phenoxy) phenylalkanone oxime and imine derivatives as herbicides |
| US4382814A (en) * | 1981-07-27 | 1983-05-10 | Rhone-Poulenc Agrochimie | Herbicidal derivatives of 5-phenoxy-2-nitrofuran-3-carboxylic acid |
| US4377408A (en) * | 1981-07-27 | 1983-03-22 | Rhone-Poulenc Agrochimie | Herbicidal derivatives of 5-phenoxy-4(3H)-quinazolinone-1-oxide |
| CN103694123B (zh) * | 2014-01-07 | 2016-03-23 | 上虞颖泰精细化工有限公司 | 一种乳氟禾草灵的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
| JPS5436208A (en) * | 1977-08-25 | 1979-03-16 | Texaco Development Corp | Process for preparing simultaneously morpholine compound and 22*22aminoalkoxy*alkanole compound |
-
1974
- 1974-06-07 US US477233A patent/US3907866A/en not_active Expired - Lifetime
-
1975
- 1975-05-20 ZA ZA3255A patent/ZA753255B/xx unknown
- 1975-05-22 CA CA227,557A patent/CA1103270A/en not_active Expired
- 1975-05-30 GB GB2366175A patent/GB1446839A/en not_active Expired
- 1975-05-30 BE BE156944A patent/BE829769A/xx not_active IP Right Cessation
- 1975-05-31 ES ES438101A patent/ES438101A1/es not_active Expired
- 1975-06-05 AR AR259091A patent/AR222287A1/es active
- 1975-06-05 NL NL7506706A patent/NL7506706A/xx not_active Application Discontinuation
- 1975-06-06 IT IT24091/75A patent/IT1038748B/it active
- 1975-06-06 FR FR7517809A patent/FR2273795A1/fr active Granted
- 1975-06-06 JP JP50068460A patent/JPS6021964B2/ja not_active Expired
- 1975-06-06 DE DE2525399A patent/DE2525399C2/de not_active Expired
- 1975-06-09 CH CH742675A patent/CH611262A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE829769A (fr) | 1975-12-01 |
| IT1038748B (it) | 1979-11-30 |
| ZA753255B (en) | 1977-01-26 |
| CH611262A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-31 |
| AR222287A1 (es) | 1981-05-15 |
| GB1446839A (en) | 1976-08-18 |
| FR2273795A1 (fr) | 1976-01-02 |
| FR2273795B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-30 |
| ES438101A1 (es) | 1977-02-01 |
| DE2525399C2 (de) | 1983-12-22 |
| US3907866A (en) | 1975-09-23 |
| JPS517124A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-01-21 |
| DE2525399A1 (de) | 1975-12-18 |
| JPS6021964B2 (ja) | 1985-05-30 |
| AU8191775A (en) | 1976-12-09 |
| NL7506706A (nl) | 1975-12-09 |
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| MKEX | Expiry |