DE3051251C2 - Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer Ether - Google Patents
Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer EtherInfo
- Publication number
- DE3051251C2 DE3051251C2 DE3051251A DE3051251A DE3051251C2 DE 3051251 C2 DE3051251 C2 DE 3051251C2 DE 3051251 A DE3051251 A DE 3051251A DE 3051251 A DE3051251 A DE 3051251A DE 3051251 C2 DE3051251 C2 DE 3051251C2
- Authority
- DE
- Germany
- Prior art keywords
- phenoxy
- active ingredient
- quinoxalyloxy
- propionate
- herbicidal
- 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 - Lifetime
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 8
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 title description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title description 4
- 239000004480 active ingredient Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004563 wettable powder Substances 0.000 claims description 11
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- -1 phenoxy fatty acid Chemical class 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims 1
- YWDFLVXKSADHHE-UHFFFAOYSA-N methyl 2-[4-(6-fluoroquinoxalin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CN=C(C=C(F)C=C2)C2=N1 YWDFLVXKSADHHE-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 24
- 239000004009 herbicide Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 231100000674 Phytotoxicity Toxicity 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JOSJOTMTUIFNMM-UHFFFAOYSA-N 3-propan-2-yl-1,4-dihydro-2,1,3-benzothiadiazine Chemical compound C1=CC=C2NSN(C(C)C)CC2=C1 JOSJOTMTUIFNMM-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 240000003176 Digitaria ciliaris Species 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001077837 Galinsoga quadriradiata Species 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 244000088415 Raphanus sativus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 240000006586 Rorippa indica var. indica Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 244000061458 Solanum melongena Species 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241001148683 Zostera marina Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 244000035395 Chenopodium ficifolium Species 0.000 description 2
- 235000009731 Chenopodium ficifolium Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VYGDWUHRJQGEQD-UHFFFAOYSA-N 1-methoxy-1-methyl-3-[2-[2-(4-methylphenyl)ethoxy]phenyl]urea Chemical compound CON(C)C(=O)NC1=CC=CC=C1OCCC1=CC=C(C)C=C1 VYGDWUHRJQGEQD-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- XJFDVTDVNVXOBM-UHFFFAOYSA-N CC(C)N.C1=NC=NC=N1 Chemical compound CC(C)N.C1=NC=NC=N1 XJFDVTDVNVXOBM-UHFFFAOYSA-N 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- PPNUOIBDZBOUST-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl]-phenylcarbamic acid Chemical compound CCOC(=O)NC1=CC=CC(N(C(O)=O)C=2C=CC=CC=2)=C1 PPNUOIBDZBOUST-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 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
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000002917 insecticide 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP54020164A JPS6033389B2 (ja) | 1979-02-22 | 1979-02-22 | 複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3051251C2 true DE3051251C2 (de) | 1993-12-16 |
Family
ID=12019508
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19803004770 Granted DE3004770A1 (de) | 1979-02-22 | 1980-02-08 | Phenoxyfettsaeurederivate vom typ heterocyclischer aether und herbizide mittel mit einem gehalt derselben |
DE3051251A Expired - Lifetime DE3051251C2 (de) | 1979-02-22 | 1980-02-08 | Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer Ether |
DE3051172A Expired - Lifetime DE3051172C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-22 | 1980-02-08 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19803004770 Granted DE3004770A1 (de) | 1979-02-22 | 1980-02-08 | Phenoxyfettsaeurederivate vom typ heterocyclischer aether und herbizide mittel mit einem gehalt derselben |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3051172A Expired - Lifetime DE3051172C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-22 | 1980-02-08 |
Country Status (23)
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ194196A (en) * | 1979-07-17 | 1983-07-15 | Ici Australia Ltd | -(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors |
US4738710A (en) * | 1979-11-19 | 1988-04-19 | Ici Australia Limited | Herbicidal alkane carboxylic acid derivatives |
AU541697B2 (en) * | 1979-11-19 | 1985-01-17 | Ici Australia Limited | Quinoline derivatives |
CA1317299C (en) * | 1980-06-23 | 1993-05-04 | Maged Mohamed Fawzi | Quinoxalinyloxy ethers as selective weed control agents |
US4609396A (en) * | 1980-06-23 | 1986-09-02 | E. I. Du Pont De Nemours And Company | Quinoxalinyloxy ethers as selective weed control agents |
NZ197421A (en) * | 1980-07-01 | 1984-08-24 | Ici Australia Ltd | Isoquinoline derivatives and herbicidal compositions |
NZ197420A (en) * | 1980-07-01 | 1984-04-27 | Ici Australia Ltd | -(quinazolin-(2-or 4-)(oxy,ylthio or amino)phen(oxy or ylthio)alkanoic acid derivatives |
NZ197419A (en) * | 1980-07-01 | 1984-08-24 | Ici Australia Ltd | Omega-(cinnolin-(2 or 3-)yl(oxy,thio or amino)phen-(oxy or ylthio))alkanoic acid derivatives |
US5364831A (en) * | 1980-08-06 | 1994-11-15 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
US6197728B1 (en) | 1980-08-06 | 2001-03-06 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
EP0046468A1 (en) * | 1980-08-21 | 1982-03-03 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
EP0052798B1 (de) * | 1980-11-26 | 1985-05-08 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Oximester, Verfahren zu deren Herstellung, ihre Verwendung, sowie diese Oximester enthaltende Mittel |
NZ199342A (en) * | 1981-01-12 | 1985-08-16 | Ici Australia Ltd | Quinoxaline derivatives and herbicides |
US4391628A (en) * | 1981-02-16 | 1983-07-05 | Ciba-Geigy Corporation | 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters |
NZ200031A (en) * | 1981-04-02 | 1984-11-09 | Ici Australia Ltd | Quinoline derivatives and herbicidal compositions containing such |
AU590676B2 (en) * | 1981-04-02 | 1989-11-09 | Ici Australia Limited | Herbicidal quinoline derivatives |
IL67463A (en) * | 1981-12-17 | 1985-12-31 | Du Pont | 2-alkoxyethoxyethyl 2-(4-(6-halo-2-quinoxy alinyloxy)phenoxy)propanoates and herbicidal compositions containing them |
JPS5929604A (ja) * | 1982-08-13 | 1984-02-16 | Nissan Chem Ind Ltd | 水性懸濁除草組成物 |
DE3478024D1 (de) * | 1983-12-06 | 1989-06-08 | Ciba Geigy Ag | Amides of 2-phenoxypropionic acid |
EP0159290A1 (de) * | 1984-03-28 | 1985-10-23 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
JPS62190172A (ja) * | 1986-02-14 | 1987-08-20 | Teijin Ltd | フエノキシ脂肪族カルボン酸誘導体および除草剤 |
US4900354A (en) * | 1986-08-29 | 1990-02-13 | The Dow Chemical Company | (Quinolinyl and quinoxalinyloxy)phenoxy alkenols and their use as post emergent herbicides |
US4976772A (en) * | 1986-08-29 | 1990-12-11 | The Dow Chemical Company | 4-((aryloxy)phenoxy)alkenol as intermediates and herbicides |
EP0270378A3 (en) * | 1986-12-05 | 1988-09-07 | E.I. Du Pont De Nemours And Company | Herbicidal aryloxybenzeneacetic acid derivatives |
DE122008000064I2 (de) * | 1988-01-06 | 2011-06-16 | Chemtura Corp N D Ges D Staates Delaware | Herbizide Heterozyklisch-alkylen-Chinoxalinyloxyphenoxy Propansäureester. |
US5120348A (en) * | 1988-01-06 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
US5319102A (en) * | 1988-01-06 | 1994-06-07 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
DE3806294A1 (de) * | 1988-02-27 | 1989-09-07 | Hoechst Ag | Herbizide mittel in form von waessrigen mikroemulsionen |
US4897481A (en) * | 1988-05-31 | 1990-01-30 | The Dow Chemical Company | Process for the minimization of racemization in the preparation of optically active ((aryloxy)phenoxy)propionate herbicides |
DE3902439A1 (de) * | 1989-01-27 | 1990-08-02 | Basf Ag | Pflanzenschuetzende mittel auf basis von 1-aryl- bzw. 1-hetarylimidazolcarbonsaeureestern |
DE3907938A1 (de) * | 1989-03-11 | 1990-09-13 | Basf Ag | 2,3-substituierte 1,8-naphthyridine, verfahren zu ihrer herstellung und ihre verwendung als antidots |
DE4042098C2 (de) * | 1990-12-28 | 1993-10-07 | Hoechst Ag | Verfahren zur Herstellung optisch aktiver Chinoxalinyloxy-phenoxypropionsäureester |
AU5686794A (en) * | 1992-12-15 | 1994-07-04 | Du Pont Merck Pharmaceutical Company, The | (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents |
DE4318092C1 (de) * | 1993-06-01 | 1995-01-12 | Basf Ag | Verfahren zur Herstellung von (R)- oder (S)-2-(4-Alkanoylphenoxy)- und (R)- oder (S)-2-(4-Aroylphenoxy)-propionsäureestern |
US5637553A (en) * | 1994-08-19 | 1997-06-10 | Platte Chemical Company | Herbicide and fertilizer composition and method of using same |
US5541152A (en) * | 1994-08-19 | 1996-07-30 | Platte Chemical Company | Herbicide and fertilizer composition and method of using same |
EP1000545B1 (en) * | 1997-07-11 | 2003-03-12 | Nissan Chemical Industries, Ltd. | Aqueous suspension-type pesticide composition |
WO2001064642A2 (en) * | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
AU2002355747B2 (en) | 2001-07-31 | 2007-12-20 | Wayne State University | Quinoline derivatives and use thereof as antitumor agents |
JP2003128501A (ja) * | 2001-10-18 | 2003-05-08 | Nissan Chem Ind Ltd | 農薬乳剤組成物 |
UA79293C2 (en) * | 2002-07-03 | 2007-06-11 | Univ Wayne State | 4-(7'-halo-2-quino (xa-) linyloxy)phenoxy propionic acid derivatives as antineoplastic agents |
US7470788B2 (en) * | 2005-09-07 | 2008-12-30 | Wayne State University | Antitumor agents |
US8183379B2 (en) * | 2005-09-07 | 2012-05-22 | Wayne State University | Antitumor agents |
JO2685B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
EP2052607A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037622A1 (de) | 2008-08-14 | 2010-02-25 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
CN106699648B (zh) * | 2016-12-15 | 2019-10-08 | 三峡大学 | 2-(4-芳氧基苯氧基)烷酸萘酯化合物及其应用 |
CN106632293B (zh) * | 2016-12-15 | 2019-02-26 | 三峡大学 | 具有生物活性的芳氧苯氧烷酸衍生物及其制备方法 |
CN106632007B (zh) * | 2016-12-15 | 2019-12-31 | 三峡大学 | 吡啶-3-基芳氧基苯氧基烷酸酯化合物及其应用 |
CN115322159B (zh) * | 2022-06-17 | 2024-01-30 | 聊城大学 | (r)-2-[4-((喹唑啉-4-酮)-2-氧基)苯氧基]丙酸酯衍生物及其应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954442A (en) * | 1972-05-17 | 1976-05-04 | Hoechst Aktiengesellschaft | Herbicidal compositions |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL283905A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-01-14 | |||
NL297470A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-09-05 | |||
US3415878A (en) * | 1962-09-10 | 1968-12-10 | Geigy Chem Corp | Process for the production of alkali metal salts of nitrilo triacetic acid |
US3472848A (en) * | 1966-11-17 | 1969-10-14 | Merck & Co Inc | 3-hydroxy and 3-mercapto-pyrazinoyl-guanidines,corresponding ethers and thioethers and processes for their preparation |
US3582315A (en) * | 1968-03-22 | 1971-06-01 | Lilly Co Eli | Methods and compositions for inhibiting plant growth |
US3752812A (en) * | 1970-02-05 | 1973-08-14 | Pfizer | 2-trifluoromethylquinoxalinedi n oxides |
US3928608A (en) * | 1972-03-14 | 1975-12-23 | Ici Ltd | Certain quinoxaline N-oxides used to combat fungi |
DK154074C (da) * | 1974-10-17 | 1989-02-27 | Ishihara Sangyo Kaisha | Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt |
US4115102A (en) * | 1974-10-17 | 1978-09-19 | Ishihara Sangyo Kaisha, Ltd. | Pyridyl compound, herbicidal composition containing the same and method of use thereof |
DE2609461C2 (de) * | 1976-03-08 | 1984-11-22 | Hoechst Ag, 6230 Frankfurt | α-4-(Trifluormethylphenoxy)-phenoxy-propionsäuren und ihre Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel |
CA1091914A (en) * | 1976-07-05 | 1980-12-23 | Hideo Kogure | Metal surface treatment liquid and rust preventive paint |
DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
EP0000176B1 (de) * | 1977-06-29 | 1981-09-16 | Ciba-Geigy Ag | Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel |
GB2026865A (en) * | 1978-03-01 | 1980-02-13 | Ici Ltd | Herbicides |
US4391628A (en) * | 1981-02-16 | 1983-07-05 | Ciba-Geigy Corporation | 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters |
-
1979
- 1979-02-22 JP JP54020164A patent/JPS6033389B2/ja not_active Expired
-
1980
- 1980-01-29 US US06/116,381 patent/US4629493A/en not_active Expired - Lifetime
- 1980-01-31 IL IL59281A patent/IL59281A/xx unknown
- 1980-01-31 ZA ZA00800574A patent/ZA80574B/xx unknown
- 1980-02-07 GB GB8004144A patent/GB2042539B/en not_active Expired
- 1980-02-08 DE DE19803004770 patent/DE3004770A1/de active Granted
- 1980-02-08 DE DE3051251A patent/DE3051251C2/de not_active Expired - Lifetime
- 1980-02-08 DE DE3051172A patent/DE3051172C2/de not_active Expired - Lifetime
- 1980-02-13 NL NLAANVRAGE8000888,A patent/NL185280C/xx not_active IP Right Cessation
- 1980-02-14 CH CH1207/80A patent/CH647510A5/de not_active IP Right Cessation
- 1980-02-18 CA CA000345903A patent/CA1306259C/en not_active Expired - Lifetime
- 1980-02-18 FR FR8003505A patent/FR2449683A1/fr active Granted
- 1980-02-19 CS CS801157A patent/CS226009B2/cs unknown
- 1980-02-20 DD DD80219165A patent/DD151038A5/de not_active IP Right Cessation
- 1980-02-20 ES ES488795A patent/ES488795A0/es active Granted
- 1980-02-20 PL PL1980222116A patent/PL128652B1/pl unknown
- 1980-02-20 EG EG101/80A patent/EG14184A/xx active
- 1980-02-20 BE BE0/199466A patent/BE881815A/fr not_active IP Right Cessation
- 1980-02-20 AU AU55729/80A patent/AU533042B2/en not_active Expired
- 1980-02-20 AT AT0093280A patent/AT365407B/de not_active IP Right Cessation
- 1980-02-21 AR AR280042A patent/AR226300A1/es active
- 1980-02-21 SE SE8001368A patent/SE447108B/sv not_active IP Right Cessation
- 1980-02-21 SU SU802883702A patent/SU1452455A3/ru active
- 1980-02-22 IT IT20112/80A patent/IT1195260B/it active
- 1980-02-22 BR BR8001061A patent/BR8001061A/pt not_active IP Right Cessation
-
1983
- 1983-04-13 CA CA000425818A patent/CA1304377C/en not_active Expired - Lifetime
- 1983-07-26 GB GB08320051A patent/GB2126580B/en not_active Expired
-
1989
- 1989-06-02 NL NL8901398A patent/NL8901398A/nl active Search and Examination
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954442A (en) * | 1972-05-17 | 1976-05-04 | Hoechst Aktiengesellschaft | Herbicidal compositions |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3051251C2 (de) | Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer Ether | |
DE69625587T2 (de) | Synergistiche herbizide zusammensetzungen mit metolachlor | |
DD234604A5 (de) | Verfahren zur selektiven unkrautbekaempfung in nutzpflanzenkulturen | |
CH668530A5 (de) | Synergistisches mittel und verfahren zur selektiven unkrautbekaempfung in reis. | |
DE69702968T2 (de) | Herbizide zusammensetzung und deren verwendung zur unkrautbekämpfung | |
DE3688982T2 (de) | Synergistische, herbizide Kombinationen und Verfahren zur Anwendung. | |
EP1290944B1 (de) | Herbizides Mittel | |
DD142643A5 (de) | Herbizide mittel | |
EP0768034A1 (de) | Herbizides synergistisches Mittel und Verfahren zur Unkrautbekämpfung | |
DE4236475A1 (de) | Herbizide Mittel zur Unkrautbekämpfung in Reiskulturen | |
DD301896A9 (de) | Zusammensetzung und Methode zur Verringerung der Phytotoxitaet fuer Kulturpflanzen aufgrund von herbiziden Benzoesaeurederivaten | |
EP0296319B1 (de) | Herbizide Mittel auf der Basis von Heteroaryloxyphenoxycarbonsäure-Derivaten | |
DE69106252T2 (de) | Herbizide Zusammensetzung. | |
DE19937815A1 (de) | Herbizide Mittel | |
DE2914300C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
DE69906611T2 (de) | Herbizide Mischungen | |
EP0288432A1 (de) | Schädlingsbekämpfungsmittel | |
DE3110473C2 (de) | N-Alkyl-2'-n-butoxy-6'-ethyl-2-chloracetanilide und Herbizide, welche diese Verbindungen enthalten | |
DE2832046A1 (de) | Herbizide mittel auf der basis von acetaniliden | |
EP0182740A2 (de) | Synergistisches Mittel und Verfahren zur selektiven Unkrautbekämpfung, insbesondere in Getreide | |
DD262992A5 (de) | Nematizide und insektizide zusammensetzung | |
DE69109399T2 (de) | Herbizide Zusammensetzungen. | |
EP0069705B1 (de) | Synergistisches Mittel und Verfahren zur selektiven Unkrautbekämpfung, insbesondere in Getreide | |
DE2729672A1 (de) | Germicide herbicide fuer landwirtschaft und gartenbau | |
EP0208245B1 (de) | Herbizide und wachstumsregulierende Mittel auf Basis von Chinolinderivaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 3004770 |
|
8110 | Request for examination paragraph 44 | ||
8181 | Inventor (new situation) |
Free format text: URA, YASUKAZU SAKATA, GOZYO MAKINO, KENZI KAWAMURA, YASUO, FUNABASHI, CHIBA, JP KAWAMURA, YUZI IKAI, TAKASI OGUTI, TOSIHIKO, MINAMI, SAITAMA, JP |
|
AC | Divided out of |
Ref country code: DE Ref document number: 3004770 Format of ref document f/p: P |
|
AC | Divided out of |
Ref country code: DE Ref document number: 3004770 Format of ref document f/p: P |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition |