DE2525399C2 - Höhere Halogenphenoxybenzoesäureester und diese enthaltende herbizid wirksame Masse - Google Patents
Höhere Halogenphenoxybenzoesäureester und diese enthaltende herbizid wirksame MasseInfo
- Publication number
- DE2525399C2 DE2525399C2 DE2525399A DE2525399A DE2525399C2 DE 2525399 C2 DE2525399 C2 DE 2525399C2 DE 2525399 A DE2525399 A DE 2525399A DE 2525399 A DE2525399 A DE 2525399A DE 2525399 C2 DE2525399 C2 DE 2525399C2
- Authority
- DE
- Germany
- Prior art keywords
- oil
- ester
- nitrobenzoic acid
- dichlorophenoxy
- halophenoxybenzoic
- 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
- 239000002253 acid Substances 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 9
- 239000000203 mixture Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 8
- 231100000674 Phytotoxicity Toxicity 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 244000299507 Gossypium hirsutum Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- -1 2-octyl ester Chemical class 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000219144 Abutilon Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000005474 African couch grass Nutrition 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 241001520106 Eustachys Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000013146 percutaneous coronary intervention Methods 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 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 description 1
- CNCNJLDAXNGLQX-UHFFFAOYSA-N 2-nitro-5-(2,4,6-trichlorophenoxy)benzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 CNCNJLDAXNGLQX-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 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
- 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 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- 241000220243 Brassica sp. Species 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KZPZKNHAIWLBJQ-UHFFFAOYSA-N MC-3761 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 KZPZKNHAIWLBJQ-UHFFFAOYSA-N 0.000 description 1
- VDTUHFXWUUZATR-UHFFFAOYSA-N MC-7181 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2F)Cl)=C1 VDTUHFXWUUZATR-UHFFFAOYSA-N 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 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
- 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 description 1
- FOIQNJLSJIFRSM-UHFFFAOYSA-N butan-2-yl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)CC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 FOIQNJLSJIFRSM-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
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 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
- 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 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
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent 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
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material 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
- 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
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000006396 nitration reaction Methods 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
- AYKFOQGMPBQZCY-UHFFFAOYSA-N octan-2-yl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)CCCCCC)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 AYKFOQGMPBQZCY-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
- QLXSYVFLLVEKMS-UHFFFAOYSA-N pentyl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCCCCC)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 QLXSYVFLLVEKMS-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- KWGSIDJQVNEVQI-UHFFFAOYSA-N propan-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 KWGSIDJQVNEVQI-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
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000021217 seedling development Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 239000000725 suspension Substances 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
- 244000045561 useful plants Species 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US477233A US3907866A (en) | 1974-06-07 | 1974-06-07 | Higher halophenoxy benzoic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2525399A1 DE2525399A1 (de) | 1975-12-18 |
| DE2525399C2 true DE2525399C2 (de) | 1983-12-22 |
Family
ID=23895075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2525399A Expired DE2525399C2 (de) | 1974-06-07 | 1975-06-06 | Höhere Halogenphenoxybenzoesäureester und diese enthaltende herbizid wirksame Masse |
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
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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 |
| 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 |
| CA1103270A (en) | 1981-06-16 |
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| 8127 | New person/name/address of the applicant |
Owner name: RHONE-POULENC INC., NEW YORK, N.Y:, US |
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Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT. GERNHARDT, C., |
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| 8126 | Change of the secondary classification |
Ipc: A01N 37/48 |
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