JPH0517910B2 - - Google Patents
Info
- Publication number
- JPH0517910B2 JPH0517910B2 JP59186101A JP18610184A JPH0517910B2 JP H0517910 B2 JPH0517910 B2 JP H0517910B2 JP 59186101 A JP59186101 A JP 59186101A JP 18610184 A JP18610184 A JP 18610184A JP H0517910 B2 JPH0517910 B2 JP H0517910B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compound
- reaction
- ethyl
- parts
- 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 claims description 18
- 239000004009 herbicide Substances 0.000 claims description 16
- -1 5-{1-[4-(4-cyanophenoxy)phenoxy]-ethyl}-1,2,4-oxadiazole Chemical compound 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 241000209094 Oryza Species 0.000 description 14
- 235000007164 Oryza sativa Nutrition 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005574 MCPA Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical class N1NC=CO1 VEUMBMHMMCOFAG-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
- NJUXWBYUDDEXAQ-UHFFFAOYSA-N 2-[4-(2,4-dichloro-3-methylbenzoyl)-2,5-dimethylpyrazol-3-yl]oxy-1-phenylethanone Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 NJUXWBYUDDEXAQ-UHFFFAOYSA-N 0.000 description 1
- HBAKZIQTSJVVNU-UHFFFAOYSA-N 2-[4-(4-cyanophenoxy)phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=CC=C(C#N)C=C1 HBAKZIQTSJVVNU-UHFFFAOYSA-N 0.000 description 1
- ZNOVDQNFEJCRQZ-UHFFFAOYSA-N 3-propan-2-yl-2$l^{4},1,3-benzothiadiazine 2-oxide Chemical compound C1=CC=CC2=NS(=O)N(C(C)C)C=C21 ZNOVDQNFEJCRQZ-UHFFFAOYSA-N 0.000 description 1
- UVDBFPSMMXTFOU-UHFFFAOYSA-N 5-[1-[4-(2,4-dichlorophenoxy)phenoxy]ethyl]-1,2,4-oxadiazole Chemical compound N=1C=NOC=1C(C)OC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1Cl UVDBFPSMMXTFOU-UHFFFAOYSA-N 0.000 description 1
- DIUKGQCXFKKMFJ-UHFFFAOYSA-N 5-ethyl-1,2,4-oxadiazole Chemical class CCC1=NC=NO1 DIUKGQCXFKKMFJ-UHFFFAOYSA-N 0.000 description 1
- WCVZCRBJVJVEJK-UHFFFAOYSA-N C1=CC(Cl)=CC=C1CON1C(=O)C(C(CCC2)C=3C=CC=CC=3)=C2C1=O Chemical compound C1=CC(Cl)=CC=C1CON1C(=O)C(C(CCC2)C=3C=CC=CC=3)=C2C1=O WCVZCRBJVJVEJK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QRZNIJZSHWVOJN-UHFFFAOYSA-N ClOC1=CC(=C(C=C1)C)OC(C(=O)O)C Chemical compound ClOC1=CC(=C(C=C1)C)OC(C(=O)O)C QRZNIJZSHWVOJN-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- IONSZLINWCGRRI-UHFFFAOYSA-N n'-hydroxymethanimidamide Chemical compound NC=NO IONSZLINWCGRRI-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- RFJIIFDPIKJDOI-UHFFFAOYSA-N s-benzyl n,n-dimethylcarbamothioate Chemical compound CN(C)C(=O)SCC1=CC=CC=C1 RFJIIFDPIKJDOI-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59186101A JPS6163668A (ja) | 1984-09-05 | 1984-09-05 | 選択性除草剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59186101A JPS6163668A (ja) | 1984-09-05 | 1984-09-05 | 選択性除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6163668A JPS6163668A (ja) | 1986-04-01 |
| JPH0517910B2 true JPH0517910B2 (ko) | 1993-03-10 |
Family
ID=16182377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59186101A Granted JPS6163668A (ja) | 1984-09-05 | 1984-09-05 | 選択性除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6163668A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3880544D1 (de) * | 1987-04-21 | 1993-06-03 | Basf Ag | P-phenoxy-phenoxymethyl-fuenfring-heteroaromaten. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5657774A (en) * | 1979-10-16 | 1981-05-20 | Mitsui Toatsu Chem Inc | Oxadiazole compound |
| JPS57175179A (en) * | 1981-04-22 | 1982-10-28 | Mitsui Toatsu Chem Inc | 5-ethyloxadiazole derivative, herbicide, and preparation thereof |
| JPS58210073A (ja) * | 1982-06-01 | 1983-12-07 | Sumitomo Chem Co Ltd | １，２，４−オキサジアゾ−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
-
1984
- 1984-09-05 JP JP59186101A patent/JPS6163668A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5657774A (en) * | 1979-10-16 | 1981-05-20 | Mitsui Toatsu Chem Inc | Oxadiazole compound |
| JPS57175179A (en) * | 1981-04-22 | 1982-10-28 | Mitsui Toatsu Chem Inc | 5-ethyloxadiazole derivative, herbicide, and preparation thereof |
| JPS58210073A (ja) * | 1982-06-01 | 1983-12-07 | Sumitomo Chem Co Ltd | １，２，４−オキサジアゾ−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6163668A (ja) | 1986-04-01 |
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