JPH0575744B2 - - Google Patents
Info
- Publication number
- JPH0575744B2 JPH0575744B2 JP10795590A JP10795590A JPH0575744B2 JP H0575744 B2 JPH0575744 B2 JP H0575744B2 JP 10795590 A JP10795590 A JP 10795590A JP 10795590 A JP10795590 A JP 10795590A JP H0575744 B2 JPH0575744 B2 JP H0575744B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- bis
- amino
- compound
- 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 - Lifetime
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- JLFVZLNEALJLLS-UHFFFAOYSA-N 4,6-bis(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=N1 JLFVZLNEALJLLS-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- -1 aminotrifluoromethylpyridine compound Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 3
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical class FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 3
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-UHFFFAOYSA-N 0.000 description 3
- NJFRBMFEAGFNDC-UHFFFAOYSA-N 5-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CN=CC(C(F)(F)F)=C1 NJFRBMFEAGFNDC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RRNXYHYDSDAOFW-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1C(F)(F)F RRNXYHYDSDAOFW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DPQYRXNRGNLPFC-UHFFFAOYSA-N 2,4-dichloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1Cl DPQYRXNRGNLPFC-UHFFFAOYSA-N 0.000 description 1
- LROCMWGCEQNQKS-UHFFFAOYSA-N 2,6-difluoro-n-[[5-(trifluoromethyl)pyridin-3-yl]carbamoyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CN=CC(C(F)(F)F)=C1 LROCMWGCEQNQKS-UHFFFAOYSA-N 0.000 description 1
- XZKZVCLLDKWOKM-UHFFFAOYSA-N 2-(trifluoromethyl)pyridin-3-amine Chemical class NC1=CC=CN=C1C(F)(F)F XZKZVCLLDKWOKM-UHFFFAOYSA-N 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000299906 Cucumis sativus var. sativus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZJEVYKHEGWJGLW-UHFFFAOYSA-N [4-(trifluoromethyl)pyridin-2-yl]urea Chemical compound NC(=O)NC1=CC(C(F)(F)F)=CC=N1 ZJEVYKHEGWJGLW-UHFFFAOYSA-N 0.000 description 1
- VWUFOQNDKHREFL-UHFFFAOYSA-N [5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound NC(=O)NC1=CN=CC(C(F)(F)F)=C1 VWUFOQNDKHREFL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IYRAJWJZMJULHR-UHFFFAOYSA-N n-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-4,6-bis(trifluoromethyl)pyridin-2-amine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=N1 IYRAJWJZMJULHR-UHFFFAOYSA-N 0.000 description 1
- GOOSRMAJKJDGHX-UHFFFAOYSA-N n-[[4,6-bis(trifluoromethyl)pyridin-2-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=N1 GOOSRMAJKJDGHX-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10795590A JPH0386863A (ja) | 1990-04-24 | 1990-04-24 | アミノトリフルオロメチルピリジン系化合物及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10795590A JPH0386863A (ja) | 1990-04-24 | 1990-04-24 | アミノトリフルオロメチルピリジン系化合物及びその製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60295171A Division JPS62155259A (ja) | 1985-12-27 | 1985-12-27 | アミノトリフルオロメチルピリジン系化合物及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0386863A JPH0386863A (ja) | 1991-04-11 |
| JPH0575744B2 true JPH0575744B2 (enrdf_load_stackoverflow) | 1993-10-21 |
Family
ID=14472297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10795590A Granted JPH0386863A (ja) | 1990-04-24 | 1990-04-24 | アミノトリフルオロメチルピリジン系化合物及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0386863A (enrdf_load_stackoverflow) |
-
1990
- 1990-04-24 JP JP10795590A patent/JPH0386863A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0386863A (ja) | 1991-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |