JPH0714916B2 - α‐不飽和アミン類及びそれを含む組成物 - Google Patents

α‐不飽和アミン類及びそれを含む組成物

Info

Publication number: JPH0714916B2
Authority: JP; Japan
Prior art keywords: group; alkyl; alkoxy; atom; halogen
Prior art date: 1987-08-01
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

Application number

JP63192383A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02171A (ja

Inventor

勲南田

幸一岩永

哲夫岡内

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1987-08-01

Filing date

1988-08-01

Publication date

1995-02-22

1988-08-01 Application filed by Takeda Pharmaceutical Co Ltd filed Critical Takeda Pharmaceutical Co Ltd

1988-08-01 Priority to JP63192383A priority Critical patent/JPH0714916B2/ja

1990-01-05 Publication of JPH02171A publication Critical patent/JPH02171A/ja

1995-02-22 Publication of JPH0714916B2 publication Critical patent/JPH0714916B2/ja

2010-02-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 128
150000001412 amines Chemical class 0.000 title claims description 56
-1 hydroxy, amino Chemical group 0.000 claims description 666
150000001875 compounds Chemical class 0.000 claims description 401
125000000217 alkyl group Chemical group 0.000 claims description 129
150000003839 salts Chemical class 0.000 claims description 97
229910052736 halogen Inorganic materials 0.000 claims description 82
150000002367 halogens Chemical class 0.000 claims description 81
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
125000003545 alkoxy group Chemical group 0.000 claims description 74
125000003282 alkyl amino group Chemical group 0.000 claims description 71
229910052757 nitrogen Inorganic materials 0.000 claims description 65
125000000623 heterocyclic group Chemical group 0.000 claims description 54
125000002252 acyl group Chemical group 0.000 claims description 53
125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 44
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 43
125000003342 alkenyl group Chemical group 0.000 claims description 43
125000003710 aryl alkyl group Chemical group 0.000 claims description 43
125000004769 (C1-C4) alkylsulfonyl group Chemical class 0.000 claims description 42
125000003118 aryl group Chemical group 0.000 claims description 38
125000004076 pyridyl group Chemical group 0.000 claims description 38
125000004430 oxygen atom Chemical group O* 0.000 claims description 36
125000004414 alkyl thio group Chemical group 0.000 claims description 34
229910052799 carbon Inorganic materials 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 33
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 32
238000004519 manufacturing process Methods 0.000 claims description 32
125000006575 electron-withdrawing group Chemical group 0.000 claims description 28
125000000304 alkynyl group Chemical group 0.000 claims description 26
125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 26
125000004434 sulfur atom Chemical group 0.000 claims description 25
125000004442 acylamino group Chemical group 0.000 claims description 24
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 23
125000000000 cycloalkoxy group Chemical group 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 22
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 22
125000004104 aryloxy group Chemical group 0.000 claims description 22
150000001721 carbon Chemical group 0.000 claims description 22
125000000335 thiazolyl group Chemical group 0.000 claims description 22
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
230000000895 acaricidal effect Effects 0.000 claims description 16
125000005103 alkyl silyl group Chemical group 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
125000004122 cyclic group Chemical group 0.000 claims description 13
230000000749 insecticidal effect Effects 0.000 claims description 13
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
125000003302 alkenyloxy group Chemical group 0.000 claims description 12
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 11
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 11
125000004423 acyloxy group Chemical group 0.000 claims description 11
125000005236 alkanoylamino group Chemical group 0.000 claims description 11
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 11
125000000676 alkoxyimino group Chemical group 0.000 claims description 11
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
125000005133 alkynyloxy group Chemical group 0.000 claims description 11
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 11
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 11
125000001769 aryl amino group Chemical group 0.000 claims description 11
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 11
125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 11
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 11
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 11
125000005110 aryl thio group Chemical group 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 11
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 11
125000005366 cycloalkylthio group Chemical group 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 11
125000004995 haloalkylthio group Chemical group 0.000 claims description 11
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 11
125000000542 sulfonic acid group Chemical group 0.000 claims description 11
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000004397 aminosulfonyl group Chemical class NS(=O)(=O)* 0.000 claims description 9
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 9
239000007795 chemical reaction product Substances 0.000 claims description 8
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 7
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 6
238000005917 acylation reaction Methods 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
238000007083 alkoxycarbonylation reaction Methods 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
230000014509 gene expression Effects 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
238000006366 phosphorylation reaction Methods 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
230000006103 sulfonylation Effects 0.000 claims description 2
238000005694 sulfonylation reaction Methods 0.000 claims description 2
230000001404 mediated effect Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 177
239000013078 crystal Substances 0.000 description 169
239000003921 oil Substances 0.000 description 157
235000019198 oils Nutrition 0.000 description 157
238000002844 melting Methods 0.000 description 145
230000008018 melting Effects 0.000 description 145
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 123
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
IXAGRXJIXIPQDR-UHFFFAOYSA-N 2-nitroethenamine Chemical group NC=C[N+]([O-])=O IXAGRXJIXIPQDR-UHFFFAOYSA-N 0.000 description 65
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
239000002904 solvent Substances 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
238000003756 stirring Methods 0.000 description 42
NESLOYMMIUOLMU-UHFFFAOYSA-N 1-n'-methyl-2-nitroethene-1,1-diamine Chemical group CNC(N)=C[N+]([O-])=O NESLOYMMIUOLMU-UHFFFAOYSA-N 0.000 description 40
239000000460 chlorine Substances 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
238000001914 filtration Methods 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 36
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 36
238000010992 reflux Methods 0.000 description 36
239000000741 silica gel Substances 0.000 description 33
229910002027 silica gel Inorganic materials 0.000 description 33
239000000047 product Substances 0.000 description 30
238000001816 cooling Methods 0.000 description 29
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 29
SGROJTFSHJVVSF-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)ethanamine Chemical compound CCNCC1=CC=CN=C1 SGROJTFSHJVVSF-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000126 substance Substances 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 24
239000002585 base Substances 0.000 description 23
238000004440 column chromatography Methods 0.000 description 23
238000010898 silica gel chromatography Methods 0.000 description 23
239000003795 chemical substances by application Substances 0.000 description 22
DQCSAZILCMXZRP-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-n-methylmethanamine Chemical compound CNCC1=CC(C)=NC(C)=C1 DQCSAZILCMXZRP-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000000843 powder Substances 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
238000001035 drying Methods 0.000 description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
239000005457 ice water Substances 0.000 description 18
239000000706 filtrate Substances 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 15
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
239000012312 sodium hydride Substances 0.000 description 15
229910000104 sodium hydride Inorganic materials 0.000 description 15
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 11
AJEQAGLDUXLZQG-UHFFFAOYSA-N 1-n',1-n'-dimethyl-2-nitroethene-1,1-diamine Chemical group CN(C)C(N)=C[N+]([O-])=O AJEQAGLDUXLZQG-UHFFFAOYSA-N 0.000 description 11
241000607479 Yersinia pestis Species 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
239000010410 layer Substances 0.000 description 11
MCSAQVGDZLPTBS-UHFFFAOYSA-N n-methyl-1-pyridin-3-ylmethanamine Chemical compound CNCC1=CC=CN=C1 MCSAQVGDZLPTBS-UHFFFAOYSA-N 0.000 description 11
DZDKFYMSTBDSGF-UHFFFAOYSA-N 1-methylsulfanyl-2-nitroethenamine Chemical group CSC(N)=C[N+]([O-])=O DZDKFYMSTBDSGF-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
238000010828 elution Methods 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
239000002917 insecticide Substances 0.000 description 10
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
230000035484 reaction time Effects 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
CMPPTKONDXHDBF-UHFFFAOYSA-N 2,6-dichloro-3-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1Cl CMPPTKONDXHDBF-UHFFFAOYSA-N 0.000 description 8
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
239000012267 brine Substances 0.000 description 8
150000002170 ethers Chemical class 0.000 description 8
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000011734 sodium Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000006227 byproduct Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
HUDRYGJMGVJMCD-UHFFFAOYSA-N n,n-dimethyl-1-methylsulfanyl-2-nitroethenamine Chemical group CSC(N(C)C)=C[N+]([O-])=O HUDRYGJMGVJMCD-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
239000000758 substrate Substances 0.000 description 7
XPARFBOWIYMLMY-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanamine Chemical compound NCC1=CC=C(Cl)N=C1 XPARFBOWIYMLMY-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000000642 acaricide Substances 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000002198 insoluble material Substances 0.000 description 6
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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KBXNOAQLDBAVEW-UHFFFAOYSA-N methyl n-(6-chloropyridin-3-yl)-n'-methyl-n-propylcarbamimidothioate Chemical compound CCCN(C(SC)=NC)C1=CC=C(Cl)N=C1 KBXNOAQLDBAVEW-UHFFFAOYSA-N 0.000 description 1
ISWYLQPJHOENML-UHFFFAOYSA-N methyl n-(6-chloropyridin-3-yl)-n-methyl-n'-propylcarbamimidothioate Chemical compound CCCN=C(SC)N(C)C1=CC=C(Cl)N=C1 ISWYLQPJHOENML-UHFFFAOYSA-N 0.000 description 1
LLFSQZMQXDRSIF-UHFFFAOYSA-N methyl n-(6-methoxypyridin-3-yl)-n,n'-dimethylcarbamimidothioate Chemical compound COC1=CC=C(N(C)C(SC)=NC)C=N1 LLFSQZMQXDRSIF-UHFFFAOYSA-N 0.000 description 1
XKDNDALTJFUQHM-UHFFFAOYSA-N methyl n-[(2,6-dimethylpyridin-4-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC(C)=NC(C)=C1 XKDNDALTJFUQHM-UHFFFAOYSA-N 0.000 description 1
GIKAIJYYKFIRIS-UHFFFAOYSA-N methyl n-[(2-chloro-1,3-thiazol-5-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CN=C(Cl)S1 GIKAIJYYKFIRIS-UHFFFAOYSA-N 0.000 description 1
CICBELOLHPKTST-UHFFFAOYSA-N methyl n-[(2-chloro-1,3-thiazol-5-yl)methyl]-n-ethyl-n'-methylcarbamimidothioate Chemical compound CSC(=NC)N(CC)CC1=CN=C(Cl)S1 CICBELOLHPKTST-UHFFFAOYSA-N 0.000 description 1
DRZYNGXDFRIGEB-UHFFFAOYSA-N methyl n-[(2-chloropyridin-3-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC=CN=C1Cl DRZYNGXDFRIGEB-UHFFFAOYSA-N 0.000 description 1
OEWFGSYNUXQSAM-UHFFFAOYSA-N methyl n-[(4-chlorophenyl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC=C(Cl)C=C1 OEWFGSYNUXQSAM-UHFFFAOYSA-N 0.000 description 1
IKUTWFJSAOPJQT-UHFFFAOYSA-N methyl n-[(5-bromopyridin-3-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CN=CC(Br)=C1 IKUTWFJSAOPJQT-UHFFFAOYSA-N 0.000 description 1
ISNVBUSHZBDYMG-UHFFFAOYSA-N methyl n-[(6-bromopyridin-3-yl)methyl]-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NCC1=CC=C(Br)N=C1 ISNVBUSHZBDYMG-UHFFFAOYSA-N 0.000 description 1
AINJLUUAWHFLCB-UHFFFAOYSA-N methyl n-[(6-bromopyridin-3-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC=C(Br)N=C1 AINJLUUAWHFLCB-UHFFFAOYSA-N 0.000 description 1
HWVHJNNXTHKITQ-UHFFFAOYSA-N methyl n-[(6-bromopyridin-3-yl)methyl]-n-ethyl-n'-methylcarbamimidothioate Chemical compound CSC(=NC)N(CC)CC1=CC=C(Br)N=C1 HWVHJNNXTHKITQ-UHFFFAOYSA-N 0.000 description 1
AIYUZRWYQVBRJM-UHFFFAOYSA-N methyl n-[(6-chloropyridin-3-yl)methyl]-n'-ethyl-n-methylcarbamimidothioate Chemical compound CCN=C(SC)N(C)CC1=CC=C(Cl)N=C1 AIYUZRWYQVBRJM-UHFFFAOYSA-N 0.000 description 1
KLJQLRUXXCTOOR-UHFFFAOYSA-N methyl n-[(6-chloropyridin-3-yl)methyl]-n'-methyl-n-(2,2,2-trifluoroethyl)carbamimidothioate Chemical compound CSC(=NC)N(CC(F)(F)F)CC1=CC=C(Cl)N=C1 KLJQLRUXXCTOOR-UHFFFAOYSA-N 0.000 description 1
NYNMJPBNLBLEDZ-UHFFFAOYSA-N methyl n-[(6-chloropyridin-3-yl)methyl]-n'-methyl-n-propylcarbamimidothioate Chemical compound CCCN(C(SC)=NC)CC1=CC=C(Cl)N=C1 NYNMJPBNLBLEDZ-UHFFFAOYSA-N 0.000 description 1
LYZCUEOHQMXCKL-UHFFFAOYSA-N methyl n-[(6-chloropyridin-3-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC=C(Cl)N=C1 LYZCUEOHQMXCKL-UHFFFAOYSA-N 0.000 description 1
ACCWCZRJVRRLQM-UHFFFAOYSA-N methyl n-[(6-chloropyridin-3-yl)methyl]-n-ethyl-n'-methylcarbamimidothioate Chemical compound CSC(=NC)N(CC)CC1=CC=C(Cl)N=C1 ACCWCZRJVRRLQM-UHFFFAOYSA-N 0.000 description 1
GHOPSGFVEQQDQQ-UHFFFAOYSA-N methyl n-[(6-fluoropyridin-3-yl)methyl]-n,n'-dimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)CC1=CC=C(F)N=C1 GHOPSGFVEQQDQQ-UHFFFAOYSA-N 0.000 description 1
XGCJHCCMFJMBKO-UHFFFAOYSA-N methyl n-butyl-n-(6-chloropyridin-3-yl)-n'-methylcarbamimidothioate Chemical compound CCCCN(C(SC)=NC)C1=CC=C(Cl)N=C1 XGCJHCCMFJMBKO-UHFFFAOYSA-N 0.000 description 1
WTGYXCPJSLBPSQ-UHFFFAOYSA-N methyl n-ethyl-n-[(6-fluoropyridin-3-yl)methyl]-n'-methylcarbamimidothioate Chemical compound CSC(=NC)N(CC)CC1=CC=C(F)N=C1 WTGYXCPJSLBPSQ-UHFFFAOYSA-N 0.000 description 1
QGLSAVBDMGIAMT-UHFFFAOYSA-N methyl n-methoxy-n'-methyl-n-(pyridin-3-ylmethyl)carbamimidothioate Chemical compound CSC(=NC)N(OC)CC1=CC=CN=C1 QGLSAVBDMGIAMT-UHFFFAOYSA-N 0.000 description 1
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ADWCWILGFJNJRU-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]propan-1-amine Chemical compound CCCNCC1=CC=C(Cl)N=C1 ADWCWILGFJNJRU-UHFFFAOYSA-N 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

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Quinoline Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP63192383A 1987-08-01 1988-08-01 α‐不飽和アミン類及びそれを含む組成物 Expired - Lifetime JPH0714916B2 (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP63192383A JPH0714916B2 (ja)	1987-08-01	1988-08-01	α‐不飽和アミン類及びそれを含む組成物

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP62-192793		1987-08-01
JP19279387		1987-08-01
JP62-258856		1987-10-13
JP63-16259		1988-01-26
JP63-64885		1988-03-17
JP63192383A JPH0714916B2 (ja)	1987-08-01	1988-08-01	α‐不飽和アミン類及びそれを含む組成物

Related Child Applications (5)

Application Number	Title	Priority Date	Filing Date
JP5008114A Division JPH05345760A (ja)	1987-08-01	1993-01-21	ピリジルメチルアミン類
JP5008115A Division JPH05345761A (ja)	1987-08-01	1993-01-21	α−不飽和アミン化合物
JP5008116A Division JPH0749424B2 (ja)	1987-08-01	1993-01-21	チアゾリルメチルアミン類
JP6254222A Division JP2551393B2 (ja)	1987-08-01	1994-09-26	α−不飽和アミン化合物
JP6254221A Division JP2551392B2 (ja)	1987-08-01	1994-09-26	ピリジルメチルアミン類

Publications (2)

Publication Number	Publication Date
JPH02171A JPH02171A (ja)	1990-01-05
JPH0714916B2 true JPH0714916B2 (ja)	1995-02-22

Family

ID=16297088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63192383A Expired - Lifetime JPH0714916B2 (ja)	1987-08-01	1988-08-01	α‐不飽和アミン類及びそれを含む組成物

Country Status (2)

Country	Link
JP (1)	JPH0714916B2 (hu)
IN (1)	IN167709B (hu)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2345326A2 (en)	2009-12-28	2011-07-20	Sumitomo Chemical Company, Limited	Fly attractant composition containing a ligninsulfonate as active agent

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2531996B2 (ja) *	1989-03-10	1996-09-04	日本バイエルアグロケム株式会社	殺虫組成物
IE70666B1 (en)	1990-12-28	1996-12-11	Takeda Chemical Industries Ltd	Stable agrochemical compositions
RU2106088C1 (ru) *	1992-05-23	1998-03-10	Циба-Гейги АГ	Способ борьбы с блохами у домашних животных и средство для предотвращения поражения домашних животных блохами
US5424437A (en) *	1993-02-01	1995-06-13	Koei Chemical Co., Ltd.	Process for preparing a 2-chloro-5-aminomethyl-pyridine
JP3509901B2 (ja) *	1993-07-20	2004-03-22	バイエルクロップサイエンス株式会社	殺虫方法
JP2766848B2 (ja) *	1993-10-26	1998-06-18	三井化学株式会社	フラニル系殺虫剤
DE4412833A1 (de) *	1994-04-14	1995-10-19	Bayer Ag	Insektizide Düngemischungen
JPH08245314A (ja) *	1995-03-09	1996-09-24	Sumitomo Chem Co Ltd	水田における半翅目害虫の防除方法
TW328084B (en) *	1995-06-23	1998-03-11	Takeda Pharm Industry Co Ltd	Process for producing guanidine derivatives, intermediates therefor and their production
IL136585A0 (en) *	1997-12-24	2001-06-14	Takeda Chemical Industries Ltd	Method for producing isoureas
DE10347440A1 (de) *	2003-10-13	2005-05-04	Bayer Cropscience Ag	Synergistische insektizide Mischungen
AU2005213943B2 (en)	2004-02-24	2010-06-24	Sumitomo Chemical Company, Limited	Insecticide compositions
CA2574335C (en) *	2004-07-28	2013-10-01	Intervet International B.V.	Veterinary composition comprising an arylpyrazole and a nitroenamine with antiparasitic activity
JP5266944B2 (ja) *	2007-08-08	2013-08-21	住友化学株式会社	α−不飽和アミン化合物の分離精製方法

1988
- 1988-07-12 IN IN493/MAS/88A patent/IN167709B/en unknown
- 1988-08-01 JP JP63192383A patent/JPH0714916B2/ja not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2345326A2 (en)	2009-12-28	2011-07-20	Sumitomo Chemical Company, Limited	Fly attractant composition containing a ligninsulfonate as active agent

Also Published As

Publication number	Publication date
IN167709B (hu)	1990-12-08
JPH02171A (ja)	1990-01-05

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Publication	Publication Date	Title
US6124297A (en)	2000-09-26	α-unsaturated amines, their production and use
EP0665222B1 (en)	2001-06-20	Guanidine derivatives, their production and insecticides
JP2546003B2 (ja)	1996-10-23	グアニジン誘導体、その製造法及び殺虫剤
JPH0714916B2 (ja)	1995-02-22	α‐不飽和アミン類及びそれを含む組成物
KR0135974B1 (ko)	1998-04-25	테트라히드로피리미딘 화합물, 이의 제조 방법 및 이를 함유하는 해충 방제 조성물
US5696256A (en)	1997-12-09	Process for preparing and using guanidine derivatives
JP2819142B2 (ja)	1998-10-30	アクリル酸モルホリド類，その製造法及び製剤
JP3032846B2 (ja)	2000-04-17	グアニジン誘導体の製造方法、その中間体及びその製造方法
JP2859301B2 (ja)	1999-02-17	農園芸用殺虫組成物
JP2605651B2 (ja)	1997-04-30	グアニジン誘導体、その製造法及び殺虫剤
JP2859302B2 (ja)	1999-02-17	農園芸用殺虫殺菌組成物
JP2845499B2 (ja)	1999-01-13	農園芸用殺虫組成物
JP3038555B2 (ja)	2000-05-08	テトラヒドロピリミジン化合物，その製造法及び製剤
JPH1129418A (ja)	1999-02-02	農園芸用殺虫殺菌組成物
JPH05112521A (ja)	1993-05-07	ニトログアニジン誘導体の製造方法、その中間体及びその製造方法

JPH0714916B2 - α‐不飽和アミン類及びそれを含む組成物 - Google Patents

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Priority Applications (1)

Applications Claiming Priority (6)

Related Child Applications (5)

Publications (2)

Family

ID=16297088

Family Applications (1)

Country Status (2)

Cited By (1)

Families Citing this family (14)

Cited By (1)

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