JPS63431B2 - - Google Patents
Info
- Publication number
- JPS63431B2 JPS63431B2 JP2725384A JP2725384A JPS63431B2 JP S63431 B2 JPS63431 B2 JP S63431B2 JP 2725384 A JP2725384 A JP 2725384A JP 2725384 A JP2725384 A JP 2725384A JP S63431 B2 JPS63431 B2 JP S63431B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- formula
- chlorothioformate
- thiocarbamate
- reaction
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 14
- 150000003927 aminopyridines Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- -1 Alkylphenyl chlorothioformate Chemical compound 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 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
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003359 percent control normalization Methods 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VPGPNOQDNGMIKA-UHFFFAOYSA-N 6-chloro-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(Cl)=N1 VPGPNOQDNGMIKA-UHFFFAOYSA-N 0.000 description 2
- GXHQLRBOZRJHPZ-UHFFFAOYSA-N 6-methoxy-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(OC)=N1 GXHQLRBOZRJHPZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 2
- RVFDGINAGFKENO-UHFFFAOYSA-N o-(3-tert-butylphenyl) chloromethanethioate Chemical compound CC(C)(C)C1=CC=CC(OC(Cl)=S)=C1 RVFDGINAGFKENO-UHFFFAOYSA-N 0.000 description 2
- JBLFKXAALTYUTQ-UHFFFAOYSA-N o-(4-tert-butylphenyl) chloromethanethioate Chemical compound CC(C)(C)C1=CC=C(OC(Cl)=S)C=C1 JBLFKXAALTYUTQ-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- PEHWGPOHRGXPPT-UHFFFAOYSA-N (6-methylpyridin-2-yl)carbamothioic S-acid Chemical compound CC1=CC=CC(NC(S)=O)=N1 PEHWGPOHRGXPPT-UHFFFAOYSA-N 0.000 description 1
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ZBPBEXMAUBCCIR-UHFFFAOYSA-N S-(3-tert-butylphenyl) chloromethanethioate Chemical compound CC(C)(C)C1=CC=CC(SC(Cl)=O)=C1 ZBPBEXMAUBCCIR-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- BXCSECSRZVDFJC-UHFFFAOYSA-N o-(2-tert-butylphenyl) chloromethanethioate Chemical compound CC(C)(C)C1=CC=CC=C1OC(Cl)=S BXCSECSRZVDFJC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2725384A JPS60172965A (ja) | 1984-02-17 | 1984-02-17 | チオカ−バメ−ト誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2725384A JPS60172965A (ja) | 1984-02-17 | 1984-02-17 | チオカ−バメ−ト誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60172965A JPS60172965A (ja) | 1985-09-06 |
| JPS63431B2 true JPS63431B2 (pt) | 1988-01-07 |
Family
ID=12215912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2725384A Granted JPS60172965A (ja) | 1984-02-17 | 1984-02-17 | チオカ−バメ−ト誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60172965A (pt) |
-
1984
- 1984-02-17 JP JP2725384A patent/JPS60172965A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60172965A (ja) | 1985-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0292990B1 (en) | 4-Halopyridine-3-carboxamide compounds and herbicidal composition thereof | |
| JPS63429B2 (pt) | ||
| JPS63431B2 (pt) | ||
| JPS63430B2 (pt) | ||
| JPS63152367A (ja) | ３―パーフルオロアルキル―５―置換オキシイソオキサゾール誘導体およびそれを有効成分として含有する除草剤 | |
| US2416309A (en) | Alkylamine salts of dinitrophenols | |
| JPS63139149A (ja) | α−置換フエニル酢酸誘導体 | |
| US4560762A (en) | 2-Alkylaminopyridine derivatives | |
| KR830001714B1 (ko) | 디페닐 에테르 유도체의 제조방법 | |
| JPS632551B2 (pt) | ||
| US4401457A (en) | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as herbicides | |
| JPS625432B2 (pt) | ||
| JPS632550B2 (pt) | ||
| JPS632553B2 (pt) | ||
| JPS6232742B2 (pt) | ||
| 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 | |
| JPS627907B2 (pt) | ||
| JPH0386855A (ja) | シアノ酢酸アミド誘導体およびそれを有効成分とする植物病害防除剤． | |
| JPH0243744B2 (ja) | Piridajinonjudotaioyobisonoseiho | |
| JPH0635421B2 (ja) | α−フエノキシフエニル酢酸エステル | |
| JPS6155908B2 (pt) | ||
| JPS63132808A (ja) | 除草剤組成物 | |
| JPS6016974A (ja) | ピラゾ−ル誘導体，その製造方法および選択性除草剤 | |
| JPH04202157A (ja) | フェノキシ酢酸誘導体及びこれを有効成分として含有する植物生長調節剤 | |
| JPH0480025B2 (pt) |