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

Info

Publication number

JPH0714916B2

JPH0714916B2 JP63192383A JP19238388A JPH0714916B2 JP H0714916 B2 JPH0714916 B2 JP H0714916B2 JP 63192383 A JP63192383 A JP 63192383A JP 19238388 A JP19238388 A JP 19238388A JP H0714916 B2 JPH0714916 B2 JP H0714916B2

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

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• 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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• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
• 125000005394 methallyl group Chemical group 0.000 description 1
• CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
• OPUAWDUYWRUIIL-UHFFFAOYSA-L methanedisulfonate Chemical compound [O-]S(=O)(=O)CS([O-])(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-L 0.000 description 1
• 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
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• HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
• 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
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