JPS6344748B2 - - Google Patents
Info
- Publication number
- JPS6344748B2 JPS6344748B2 JP58118123A JP11812383A JPS6344748B2 JP S6344748 B2 JPS6344748 B2 JP S6344748B2 JP 58118123 A JP58118123 A JP 58118123A JP 11812383 A JP11812383 A JP 11812383A JP S6344748 B2 JPS6344748 B2 JP S6344748B2
- Authority
- JP
- Japan
- Prior art keywords
- methylaminopyridine
- methylamine
- reaction
- present
- chloro
- 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- VPGPNOQDNGMIKA-UHFFFAOYSA-N 6-chloro-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(Cl)=N1 VPGPNOQDNGMIKA-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 2
- LYEPZCPAEZKSKN-UHFFFAOYSA-N 6-bromo-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(Br)=N1 LYEPZCPAEZKSKN-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
- 241000196324 Embryophyta Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- INFPIPCTRVDPJG-UHFFFAOYSA-N o-naphthalen-2-yl chloromethanethioate Chemical compound C1=CC=CC2=CC(OC(=S)Cl)=CC=C21 INFPIPCTRVDPJG-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000878007 Miscanthus Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- -1 and after 30 minutes Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000005748 halopyridines Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- LMQJRYKENGECRN-UHFFFAOYSA-N o-naphthalen-2-yl n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3C=CC=CC3=CC=2)=N1 LMQJRYKENGECRN-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11812383A JPS6013762A (ja) | 1983-07-01 | 1983-07-01 | ２−ハロ−６−メチルアミノピリジンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11812383A JPS6013762A (ja) | 1983-07-01 | 1983-07-01 | ２−ハロ−６−メチルアミノピリジンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6013762A JPS6013762A (ja) | 1985-01-24 |
| JPS6344748B2 true JPS6344748B2 (zh) | 1988-09-06 |
Family
ID=14728602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11812383A Granted JPS6013762A (ja) | 1983-07-01 | 1983-07-01 | ２−ハロ−６−メチルアミノピリジンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6013762A (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6257811A (ja) * | 1985-09-09 | 1987-03-13 | Toyoda Gosei Co Ltd | バリ取り方法 |
| JPS6327213U (zh) * | 1986-07-31 | 1988-02-23 | ||
| JPS63189515U (zh) * | 1987-05-26 | 1988-12-06 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5062978A (zh) * | 1972-10-10 | 1975-05-29 | ||
| JPS53130675A (en) * | 1971-03-19 | 1978-11-14 | Ici Ltd | Method of producing pyridine derivative |
-
1983
- 1983-07-01 JP JP11812383A patent/JPS6013762A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53130675A (en) * | 1971-03-19 | 1978-11-14 | Ici Ltd | Method of producing pyridine derivative |
| JPS5062978A (zh) * | 1972-10-10 | 1975-05-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6013762A (ja) | 1985-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5967202A (ja) | トリフルオロメチルピリジルオキシ―フエノキシ−プロピオン化合物を有効成分とする除草剤 | |
| JPS6358818B2 (zh) | ||
| JPS6344748B2 (zh) | ||
| JPS63429B2 (zh) | ||
| JPS6158476B2 (zh) | ||
| JPS632550B2 (zh) | ||
| JPH0248550B2 (zh) | ||
| JPH03500780A (ja) | Ｎ‐シアノメチル‐２‐ピリジノン殺虫剤 | |
| JPS632553B2 (zh) | ||
| JPS6155909B2 (zh) | ||
| JPS6344746B2 (zh) | ||
| JPS632551B2 (zh) | ||
| JPS6155910B2 (zh) | ||
| JPS5877848A (ja) | シクロヘキサン誘導体の製造方法 | |
| JPS63430B2 (zh) | ||
| JPS625432B2 (zh) | ||
| JPS632552B2 (zh) | ||
| JPS632955B2 (zh) | ||
| JPH04217647A (ja) | フェニルアミン誘導体 | |
| JPS6155506B2 (zh) | ||
| JPS6155908B2 (zh) | ||
| JPS632554B2 (zh) | ||
| JPH04342505A (ja) | 除草剤組成物 | |
| JPS59130847A (ja) | α−メチル−α−エチルフェニル酢酸アニリド誘導体、その製造法及びそれを含有する除草剤 | |
| JPS632555B2 (zh) |