JPS6334867B2 - - Google Patents
Info
- Publication number
- JPS6334867B2 JPS6334867B2 JP2656479A JP2656479A JPS6334867B2 JP S6334867 B2 JPS6334867 B2 JP S6334867B2 JP 2656479 A JP2656479 A JP 2656479A JP 2656479 A JP2656479 A JP 2656479A JP S6334867 B2 JPS6334867 B2 JP S6334867B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- present
- compound
- parts
- herbicide
- 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
- 239000004009 herbicide Substances 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- IBCLSAWERCEPGP-UHFFFAOYSA-N 1-[4-(2,4-dichlorobenzoyl)-2,5-dimethylpyrazol-3-yl]oxy-3,3-dimethylbutan-2-one Chemical compound CC1=NN(C)C(OCC(=O)C(C)(C)C)=C1C(=O)C1=CC=C(Cl)C=C1Cl IBCLSAWERCEPGP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- -1 methyl ethyl ketone Chemical compound 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- VKBACYXNBGIKBK-UHFFFAOYSA-N 5-(2,4-dichlorobenzoyl)-1,2-dihydropyrazol-3-one Chemical compound ClC1=C(C(=O)C2=NNC(=C2)O)C=CC(=C1)Cl VKBACYXNBGIKBK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000237503 Pectinidae Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 238000003786 synthesis reaction Methods 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
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2656479A JPS55118465A (en) | 1979-03-07 | 1979-03-07 | Pyrazole derivative |
| GB8006221A GB2045751B (en) | 1979-03-07 | 1980-02-25 | Pyrazole derivative a process for preparing the derivative and a herbicidal composition containing the same |
| PH23682A PH16235A (en) | 1979-03-07 | 1980-02-25 | Pyrazole derivatives |
| IT48078/80A IT1143916B (it) | 1979-03-07 | 1980-03-05 | Derivati di pirazolo composizioni erbicide che li contengono e relativo procedimento di produzione |
| BR8001298A BR8001298A (pt) | 1979-03-07 | 1980-03-05 | Derivado de pirazol, composicao herbicida e processo para a preparacao de um derivado de pirazol |
| ES489227A ES489227A0 (es) | 1979-03-07 | 1980-03-05 | Un procedimiento para la preparacion de un derivado de pira-zol |
| FR8005039A FR2450821A1 (fr) | 1979-03-07 | 1980-03-06 | Derives du pyrazole, leur preparation et compositions herbicides en contenant |
| US06/128,060 US4266963A (en) | 1979-03-07 | 1980-03-07 | Pyrazole derivatives, herbicidal compositions containing the same, and a process for the preparation of the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2656479A JPS55118465A (en) | 1979-03-07 | 1979-03-07 | Pyrazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55118465A JPS55118465A (en) | 1980-09-11 |
| JPS6334867B2 true JPS6334867B2 (enrdf_load_stackoverflow) | 1988-07-12 |
Family
ID=12197025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2656479A Granted JPS55118465A (en) | 1979-03-07 | 1979-03-07 | Pyrazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55118465A (enrdf_load_stackoverflow) |
-
1979
- 1979-03-07 JP JP2656479A patent/JPS55118465A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55118465A (en) | 1980-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1110245A (en) | Phenoxy valeric acids and derivatives thereof, useful as a herbicide | |
| JPH0248550B2 (enrdf_load_stackoverflow) | ||
| JPS6334867B2 (enrdf_load_stackoverflow) | ||
| JPS6029388B2 (ja) | ピラゾール誘導体及びそれらを含有する除草剤 | |
| JPS585900B2 (ja) | 新規ジフェニルエ−テル系化合物と殺草剤 | |
| US4266963A (en) | Pyrazole derivatives, herbicidal compositions containing the same, and a process for the preparation of the same | |
| JPS6155505B2 (enrdf_load_stackoverflow) | ||
| JPS6155506B2 (enrdf_load_stackoverflow) | ||
| JPS6334870B2 (enrdf_load_stackoverflow) | ||
| JP2696252B2 (ja) | シクロヘキサンカルボン酸誘導体並びにそれを含有する除草剤及び植物生長調節剤 | |
| JPH01275565A (ja) | 置換キノリン系化合物、それらの製造方法及びそれらを有効成分として含有する除草剤 | |
| JPS5934705B2 (ja) | フエノキシフエノキシアルカンニトリル誘導体及びそれらを含有する除草剤 | |
| JPS5814402B2 (ja) | ジヨソウザイ | |
| KR840000194B1 (ko) | 피라졸 유도체의 제조방법 | |
| JPS6136485B2 (enrdf_load_stackoverflow) | ||
| JPH0764812B2 (ja) | テトラヒドロフタルイミド誘導体およびそれを有効成分とする除草剤 | |
| JPH04112876A (ja) | ピリミジンまたはトリアジン誘導体及び除草剤 | |
| JPH02115157A (ja) | スルホニルグリシン誘導体および除草剤 | |
| KR830001714B1 (ko) | 디페닐 에테르 유도체의 제조방법 | |
| JPS605589B2 (ja) | ピラゾ−ル誘導体の製造方法 | |
| KR800000902B1 (ko) | α-[4-(4-트리플루오로메틸 페녹시) 페녹시] 프로피온산계 화합물의 제조방법 | |
| JPS58167589A (ja) | ピラゾ−ル誘導体、その製法および該誘導体を含有する除草剤 | |
| JPS5843954A (ja) | ピラゾ−ル誘導体 | |
| JPH01199978A (ja) | チアジアザビシクロノナン誘導体及び除草剤 | |
| JPS6025401B2 (ja) | 除草剤 |