CN104026137B - N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is as the application of insecticide - Google Patents

N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is as the application of insecticide Download PDF

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CN104026137B
CN104026137B CN201410275568.4A CN201410275568A CN104026137B CN 104026137 B CN104026137 B CN 104026137B CN 201410275568 A CN201410275568 A CN 201410275568A CN 104026137 B CN104026137 B CN 104026137B
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thiazol
dihydrobenzofuranes
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黄明智
李全
付二霞
刘晚苟
王小舟
胡艾希
叶姣
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HUNAN HAILI ZHUZHOU FINE CHEMICALS Co Ltd
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Abstract

The invention discloses chemical constitution such as formula the application of N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide shown in I as insecticide.Formula I chemical constitution is as follows:

Description

N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is as the application of insecticide
Technical field
The present invention relates to the application of N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide as insecticide.
Background technology
Benzofuranol (chemical name 2,2-dimethyl-2,3-Dihydrobenzofuranes phenol) is the important intermediate of producing carbofuran, pacifying well the large-tonnage such as prestige and Benfuracard micro carbamate chemicals for agriculture.Carbamate chemicals for agriculture activity is high, is widely used, but toxicity is comparatively large, therefore needs lower, the active substitute products preferably of exploitation toxicity, to meet the demand in market.Part energy is transferred to the existing pesticide intermediate compound of exploitation and is being prevented and treated the purposes in entomogenous fungi grass as pesticide new variety by New pesticides discovery company of the world.Chinese patent describes the non-amino formate ester agricultural chemicals based on benzofuranol research and development: 4-(benzofuran-5-base)-2-virtue aminothiazole and preparation method thereof and application, and ZL201010553848.9,2012.7.4 authorize; 5-[2-(benzyl imino group) thiazole-4-yl] furans phenolic ether is as the application preparing bactericide, and ZL201110102467.3,2013.3.27 authorize; 5-[2-(benzyl imino group) thiazole-4-yl] furans phenolic ether and as the application preparing insecticide, ZL201110102455.0,2013.6.12 authorize; Have 5-(2-virtue aminothiazole-4-base) benzofuranol ether compound and the preparation method of activity of weeding, CN102603726A, 2012.7.25 are open; 4-(benzofuran-5-base)-2-phenylamino thiazole is as the application of bactericide, and CN103141486B, 2014.5.28 authorize.
4-(benzofuran-5-base)-2-virtue aminothiazole [CN102010406B, 2012.7.4 authorize] cytotoxicity: when active ingredient concentration is 1000mg/L, after dispenser 96h, 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base)-2-(2-pridylamino) thiazole is 93.75% to the lethality of mythimna separata, when active ingredient concentration is 500mg/L, after process 72h, 4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base)-2-phenylamino) thiazole, 4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base)-2-(2-methylphenylamino) thiazole, 4-(7-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base)-2-(2-fluoroanilino) thiazole and 4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base)-2-(the chloro-4-fluoroanilino of 3-) thiazole is respectively 95.12% to black bean aphid lethality, 62.60%, 57.53% and 59.06%.4-(benzofuran-5-base)-2-virtue aminothiazole is to two-spotted spider mite non-activity.5-[2-(benzyl imino group) thiazole-4-yl] benzofuranol or phenolic ether [ZL201110102455.0,2013.6.12 authorize] cytotoxicity: when active ingredient concentration is 500mg/L, after dispenser 72h, 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base)-2-(2-hydroxyl-3,5-cyclite imino group) thiazole and 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base)-2-(the 4-fluorine benzyl imino group) cytotoxicity of thiazole to two-spotted spider mite be respectively 53.1% and 67.7%; 5-[2-(benzyl imino group) thiazole-4-yl] benzofuranol or phenolic ether are to black bean aphid and mythimna separata non-activity.
4-(benzofuran-5-base)-2-benzyl imino thiazole is stable not; 4-(benzofuran-5-base)-2-benzyl imino thiazole is easy to be decomposed into 4-(benzofuran-5-base)-thiazolamine and aromatic aldehyde.
Tan Xiaosong describes 7 introducing active groups on benzofuranol ring and has synthesized benzofuranol phosphorylation derivates, and this compound has certain insecticidal activity [Tan Xiaosong, Master's thesis, Central China Normal University, Wuhan, 2000]; He Qixi describes and introduce oximes group on benzofuranol 7, has synthesized benzofuranol oxime ether derivatives; Under finite concentration, the certain bacteriostatic activity of this compounds exhibit [He Qixi, Master's thesis, Hunan University, Changsha, 2009].
Chinese invention patent describes N-[4-(benzofuran-5-base) thiazol-2-yl] preparation of acid amides and the application [CN103342703A, 2013.10.9 are open] as bactericide thereof.But have no the application of N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide as insecticide.
Summary of the invention
N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is the object of the present invention is to provide to eliminate aphis and the application of two spotted spider mite anti-as insecticide.
The chemical constitution of N-of the present invention [4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is such as formula shown in I:
Wherein, Y is selected from: hydrogen, deuterium, C 1~ C 2alkoxyl, C 3~ C 4unbranched alkoxy or branched alkoxy; R is selected from: hydrogen, deuterium, C 1~ C 2alkyl, C 3~ C 6straight chained alkyl or branched alkyl; R 1be selected from: hydrogen, deuterium, C 1~ C 2alkyl; R 2be selected from: C 1~ C 2alkyl, C 1~ C 2chloro alkyl or dichloro-alkyl, C 3~ C 5chloro straight chained alkyl or chloro branched alkyl; C 3~ C 17straight chained alkyl or branched alkyl; C 2~ C 6thiazolinyl; Salt is selected from: hydrochloride, hydrobromate, sulphate, phosphate, mesylate, benzene sulfonate, tosilate.
N-of the present invention [4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide presses Chinese invention patent method preparation [CN103342703A, 2013.10.9 are open].
N-of the present invention [4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide preferred compound has N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide or N-[4-(2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide or N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide.
The object of the present invention is to provide N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide preferred compound N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide or N-[4-(2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide as insecticide in the anti-application eliminated aphis.
The object of the present invention is to provide N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide preferred compound N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide or N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide as insecticide control two spotted spider mite application.
N-provided by the invention [4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide as the application of insecticide, have very high anti-ly to eliminate aphis, the insecticidal activity such as two spotted spider mite.
Embodiment
Following examples are intended to the present invention instead of limitation of the invention further are described.
Embodiment 1
The preparation of N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide (I)
Wherein, Y is selected from: hydrogen, deuterium, C 1~ C 2alkoxyl, C 3~ C 4unbranched alkoxy or branched alkoxy; R is selected from: hydrogen, deuterium, C 1~ C 2alkyl, C 3~ C 6straight chained alkyl or branched alkyl; R 1be selected from: hydrogen, deuterium, C 1~ C 2alkyl; R 2be selected from: C 1~ C 2alkyl, C 1~ C 2chloro alkyl or dichloro-alkyl, C 3~ C 5chloro straight chained alkyl or chloro branched alkyl; C 3~ C 17straight chained alkyl or branched alkyl; C 2~ C 6thiazolinyl.
N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide (I) is prepared by Chinese invention patent [CN103342703A, 2013.10.9 are open] method.The physical data of the preferred compound of above-mentioned formula (I) is as follows:
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 76.6%, m.p.252 ~ 254 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.53 (s, 6H, 2 × CH 3), 2.00 (s, 3H, CH 3), 3.06 (s, 2H, CH 2), 3.90 (s, 3H, OCH 3), 6.96 (s, 1H, thiazole-H), 7.21 (s, 1H, C 6h 2), 7.24 (s, 1H, C 6h 2), 10.51 (br, 1H, NH); D 2after O exchanges, NH peak disappears.
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 73.5%, m.p.245 ~ 248 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.15 (t, J=7.6Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 2.29 (q, J=7.6Hz, 2H, CH 2), 3.07 (s, 2H, CH 2), 3.92 (s, 3H, OCH 3), 6.97 (s, 1H, thiazole-H), 7.22 (s, 1H, C 6h 2), 7.24 (s, 1H, C 6h 2), 10.07 (br, H, NH).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide.Yield 80.3%, m.p.215 ~ 217 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 3.07 (s, 2H, CH 2), 3.95 (s, 3H, OCH 3), 4.27 (s, 2H, CH 2cl), 7.02 (s, 1H, thiazole-H), 7.25 (s, 1H, C 6h 2), 7.26 (s, 1H, C 6h 2), 9.85 (br, 1H, NH).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 82.9%, m.p.206 ~ 208 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 1.86 (d, J=7.2Hz, 3H, CH 3), 3.07 (s, 2H, CH 2), 3.95 (s, 3H, OCH 3), 4.64 (q, J=7.2Hz, 1H, CH), 7.01 (s, 1H, thiazole-H), 7.25 (s, 1H, C 6h 2), 7.26 (s, 1H, C 6h 2), 9.99 (br, 1H, NH).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 86.5%, m.p.166 ~ 168 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 1.83 (s, 3H, COCH 3), 2.49 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 3.87 (s, 3H, OCH 3), 6.98 (s, 1H, C 6h 2), 6.99 (s, 1H, C 6h 2), 10.63 (br, H, NH). 1HNMR(CDCl 3+D 2O，400MHz)δ：1.54(s，6H，2×CH 3)，1.83(s，3H，COCH 3)，2.49(s，3H，CH 3)，3.06(s，2H，CH 2)，3.87(s，3H，OCH 3)，6.97(s，1H，C 6H 2)，6.99(s，1H，C 6H 2)。
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 94.4%, m.p.173 ~ 175 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.07 ~ 1.14 (m, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 2.08 ~ 2.19 (m, 2H, CH 2), 2.49 (s, 3H, thiazole-CH 3), 3.07 (s, 2H, CH 2), 3.88 (s, 3H, OCH 3), 6.98 (s, 1H, C 6h 2), 6.99 (s, 1H, C 6h 2), 10.25 (br, H, NH). 1hNMR (CDCl 3+ D 2o, 400MHz) δ: 1.06 (t, J=7.6Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 2.08 (q, J=7.6Hz, 2H, CH 2), 2.48 (s, 3H, thiazole-CH 3), 3.07 (s, 2H, CH 2), 3.88 (s, 3H, OCH 3), 6.97 (s, 1H, C 6h 2), 6.98 (s, 1H, C 6h 2).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, yield 67.5%, m.p.151 ~ 153 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 2.51 (s, 3H, thiazole-CH 3), 3.08 (s, 2H, CH 2), 3.91 (s, 3H, OCH 3), 4.15 ~ 4.21 (s, 2H, CH 2cl), 6.99 (s, 2H, C 6h 2). 1hNMR (CDCl 3+ D 2o, 400MHz) δ: 1.54 (s, 6H, 2 × CH 3), 2.51 (s, 3H, thiazole-CH 3), 3.08 (s, 2H, CH 2), 3.91 (s, 3H, OCH 3), 4.17 (s, 2H, CH 2cl), 6.99 (s, 2H, C 6h 2).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 55.3%, m.p.204 ~ 205 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.55 (s, 6H, 2 × CH 3), 1.85 (d, J=6.8Hz, 3H, CH 3), 2.52 (s, 3H, thiazole-CH 3), 3.09 (s, 2H, CH 2), 3.93 (s, 3H, OCH 3), 4.63 (q, J=6.8Hz, 1H, CHCl), 6.99 (s, 2H, C 6h 2).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 91.2%, m.p.188 ~ 190 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.43 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.96 (s, 3H, CH 3), 3.04 (s, 2H, CH 2), 4.15 (q, J=7.2Hz, 2H, OCH 2), 6.95 (s, 1H, thiazole-H), 7.21 (s, 1H, C 6h 2), 7.23 (s, 1H, C 6h 2).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 86.1%, m.p.170 ~ 172 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.05 ~ 1.20 (m, 3H, CH 3), 1.44 (t, J=6.8Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 2.14 ~ 2.30 (m, 2H, COCH 2), 3.04 (s, 2H, CH 2), 4.16 (q, J=6.8Hz, 2H, OCH 2), 6.94 (s, 1H, thiazole-H), 7.21 (s, 1H, C 6h 2), 7.22 (s, 1H, C 6h 2). 1HNMR(CDCl 3+D 2O，400MHz)δ：1.13(t，J＝7.6Hz，3H，CH 3)，1.44(t，J＝6.8Hz，3H，OCH 3)，1.53(s，6H，2×CH 3)，2.26(q，2H，J＝7.6Hz，COCH 2)，3.05(s，2H，CH 2)，4.16(q，J＝6.8Hz，2H，OCH 2)，6.94(s，1H，C 6H 2)，7.21(s，1H，C 6H 2)，7.22(s，1H，C 6H 2)。
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, yield 71.9%, m.p.178 ~ 180 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.47 (t, J=7.2Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 3.06 (s, 2H, CH 2), 4.21 (q, J=7.2Hz, 2H, OCH 2), 4.29 (s, 1H, CH 2cl), 7.00 (s, 1H, thiazole-H), 7.24 (s, 1H, C 6h 2), 7.25 (s, 1H, C 6h 2), 9.96 (br, H, NH).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 90.5%, m.p.165 ~ 166 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.47 (t, J=6.8Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 1.85 (d, J=7.2Hz, 3H, CH 3), 3.06 (s, 2H, CH 2), 4.21 (q, J=6.8Hz, 2H, OCH 2), 4.63 (q, J=7.2Hz, 1H, CHCl), 7.00 (s, 1H, thiazole-H), 7.24 (s, 1H, C 6h 2), 7.26 (s, 1H, C 6h 2), 9.77 (br, 1H, NH).
N-[5-methyl-4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] thiazol-2-yl] acetamide, yield 87.5%, m.p.193 ~ 194 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.42 (t, J=6.8Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.79 (s, 3H, COCH 3), 2.48 (s, 3H, thiazole-CH 3), 3.05 (s, 2H, CH 2), 4.13 (q, J=6.8Hz, 2H, OCH 2), 6.96 (s, 1H, C 6h 2), 6.98 (s, 1H, C 6h 2), 11.04 (br, 1H, NH).
N-[5-methyl-4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] thiazol-2-yl] propionamide, yield 81.1%, m.p.196 ~ 198 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.10 (t, J=7.6Hz, 3H, CH 3), 1.43 (t, J=7.2Hz, 3H, OCH 2), 1.53 (s, 6H, 2 × CH 3), 2.02 (q, 2H, J=7.6Hz, COCH 2), 2.48 (s, 3H, thiazole-CH 3), 3.05 (s, 2H, CH 2), 4.13 (q, J=7.2Hz, 2H, OCH 2), 6.96 (s, 1H, C 6h 2), 6.98 (s, 1H, C 6h 2), 10.62 (br, 1H, NH).
N-[5-methyl-4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] thiazol-2-yl] chloroacetamide, yield 85.7%, m.p.187 ~ 189 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.45 (t, J=6.8Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 2.50 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 4.12 (s, 2H, CH 2cl), 4.17 (q, J=6.8Hz, 2H, OCH 2), 6.98 (s, 1H, C 6h 2), 6.99 (s, 1H, C 6h 2).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 93.1%, m.p.195 ~ 197 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.45 (t, J=7.2Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 1.83 (d, J=7.2Hz, 3H, CH 3), 2.50 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 4.17 (q, J=7.2Hz, 2H, OCH 2), 4.53 ~ 4.60 (m, 1H, CHCl), 6.98 (s, 1H, C 6h 2), 6.99 (s, 1H, C 6h 2), 9.95 (br, 1H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 86.6%, m.p.195 ~ 198 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.00 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.80 ~ 1.88 (m, 2H, CH 2), 2.00 (s, 3H, COCH 3), 3.04 (s, 2H, CH 2), 4.04 (t, J=7.2Hz, 2H, OCH 2), 6.96 (s, 1H, thiazole-H), 7.21 (s, 1H, C 6h 2), 7.22 (s, 1H, C 6h 2), 10.64 (br, 1H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 72.2%, m.p.172 ~ 174 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.00 (t, J=7.2Hz, 3H, CH 3), 1.14 (t, J=7.6Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.81 ~ 1.87 (m, 2H, CH 2), 2.27 (q, J=7.6Hz, 2H, COCH 2), 3.04 (s, 2H, CH 2), 4.05 (t, J=7.2Hz, 2H, OCH 2), 6.95 (s, 1H, thiazole-H), 7.21 (s, 1H, C 6h 2), 7.22 (s, 1H, C 6h 2), 10.11 (br, 1H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, yield 93.8%, m.p.174 ~ 176 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.03 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.83 ~ 1.90 (m, 2H, CH 2), 3.06 (s, 2H, CH 2), 4.08 (t, J=7.2Hz, 2H, OCH 2), 4.28 (s, 2H, CH 2cl), 7.01 (s, 1H, thiazole-H), 7.23 (s, 1H, C 6h 2), 7.25 (s, 1H, C 6h 2), 9.85 (br, 1H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 88.9%, m.p.157 ~ 159 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.03 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.84 (d, J=7.2Hz, 3H, CH 3), 1.81 ~ 1.91 (m, 2H, CH 2), 3.06 (s, 2H, CH 2), 4.08 (t, J=7.2Hz, 2H, OCH 2), 4.61 (q, J=7.2Hz, 2H, OCH 2), 7.01 (s, 1H, thiazole-H), 7.24 (s, 1H, C 6h 2), 7.25 (s, 1H, C 6h 2), 9.87 (br, 1H, NH).
N-[5-methyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 75.0%, m.p.133 ~ 136 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.00 (t, J=7.2Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 1.82 ~ 1.88 (m, 2H, CH 2), 2.04 (s, 3H, COCH 3), 2.45 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 4.03 (t, J=7.2Hz, 2H, OCH 2), 4.06 (s, 2H, CH 2cl), 6.90 (s, 2H, C 6h 2-H, C 6h 2), 11.58 (br, 1H, NH).
N-[5-methyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 71.1%, m.p.177 ~ 179 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 0.93 (t, J=7.2Hz, 3H, CH 3), 0.98 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.79 ~ 1.85 (m, 2H, CH 2), 1.86 ~ 1.88 (m, 2H, CH 2), 2.48 (s, 3H, thiazole-CH 3), 3.05 (s, 2H, CH 2), 4.01 (t, J=7.2Hz, 2H, OCH 2), 6.96 (s, 1H, C 6h 2), 6.98 (s, 1H, C 6h 2), 11.40 (br, 1H, NH).
N-[5-methyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, yield 81.4%, m.p.179 ~ 181 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.01 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.81 ~ 1.88 (m, 2H, CH 2), 2.50 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 4.04 (t, J=7.2Hz, 2H, OCH 2), 4.06 (s, 2H, CH 2cl), 6.97 (s, 1H, C 6h 2), 6.98 (s, 1H, C 6h 2), 10.28 (br, 1H, NH).
N-[5-methyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 77.3%, m.p.170 ~ 172 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.02 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.79 (d, J=7.2Hz, 3H, CH 3), 1.87 (m, 2H, CH 2), 2.50 (s, 3H, thiazole-CH 3), 3.06 (s, 2H, CH 2), 4.05 (t, J=7.2Hz, 2H, OCH 2), 4.49 (q, J=7.2Hz, 1H, CHCl), 6.98 (s, 1H, C 6h 2), 6.99 (s, 1H, C 6h 2), 9.95 (br, 1H, NH).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 89.3%, m.p.213 ~ 215 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 3.08 (s, 2H, CH 2), 3.95 (s, 3H, CH 3), 6.15 (s, H, CH), 7.06 (s, H, C 6h 2), 7.24 (s, H, C 6h 2), 7.26 (s, H, thiazole-H).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, yield 80.3%, m.p.210 ~ 212 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 2.13 (s, 3H, CH 3), 3.08 (s, 2H, CH 2), 3.94 (s, 3H, OCH 3), 5.69 (s, 1H, CH 2), 6.14 (s, 1H, CH 2), 6.94 (s, 1H, C 6h 2), 7.18 (s, 2H, C 6h 2), 7.19 (s, H, thiazole-H).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, yield 72.6%, m.p.181 ~ 182 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3); 1.85 (m, 2H, CH 2); 2.72 (t, J=8.0Hz, 2H, CH 2; 3.07 (s, 2H, CH 2); 3.59 (t, J=6.0Hz); 3.93 (s, 3H, OCH 3); 6.96 (s, H, C 6h 2); 7.22 (s, H, C 6h 2); 7.26 (s, H, thiazole-H); 10.13 (s, H, NH).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, yield 79.7%, m.p.178 ~ 180 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.30 (d, J=6.8Hz, 6H, 2 × CH 3); 1.54 (s, 6H, 2 × CH 3); 2.68 (m, H, CH); 2.61 (m, H, CH); 3.07 (s, 2H, CH 2); 3.95 (s, 3H, OCH 3); 6.92 (s, H, C 6h 2); 7.18 (s, H, C 6h 2); 7.19 (s, H, thiazole-H); 10.50 (s, H, NH).
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 83.8%, m.p.225 ~ 226 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.02 (t, J=7.6Hz, 3H, CH 3); 1.54 (s, 6H, 2 × CH 3); 1.80 (m, 2H, CH 2); 2.49 (t, J=7.6Hz, 2H, CH 2); 3.08 (s, 2H, CH 2); 3.94 (s, 3H, OCH 3); 6.89 (s, H, C 6h 2); 7.14 (s, H, C 6h 2); 7.14 (s, H, thiazole-H); 11.47 (s, H, NH).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 89.6%, m.p.194 ~ 195 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.55(s，6H，2×CH 3)，2.51(s，3H，CH 3)，3.08(s，2H，CH 2)，3.91(s，3H，OCH 3)，5.92(s，H，CH)，6.98(s，2H，C 6H 2)。
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, yield 81.0%, m.p.160 ~ 161 DEG C; 1hNMR (CDCl 3, 400MHz) and δ: 1.54 (s, 6H, 2 × CH 3), 2.08 (s, 3H, CH 3), 2.49 (s, 3H, CH 3), 3.08 (s, 2H, CH 2), 3.90 (s, 3H, OCH 3), 5.61 (s, 1H, CH 2), 6.02 (s, 1H, CH 2), 6.97 (s, 2H, C 6h 2), 9.96 (s, H, NH).
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, yield 84.6%, m.p.148 ~ 150 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.24(d，J＝6.8Hz，6H，2×CH 3)；1.54(s，6H，2×CH 3)；2.49(s，3H，CH 3)；2.50(m，H，CH)；3.07(s，2H，CH 2)；3.91(s，3H，OCH 3)；6.97(s，2H，C 6H 2)；9.80(s，H，NH)。
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 84.5%, m.p.140 ~ 141 DEG C. 1HNMR(CDCl 3，400MHz)δ：0.83(t，J＝7.2Hz，3H，CH 3)；1.54(s，6H，2×CH 3)；1.58(m，2H，CH 2)；2.02(t，J＝7.2Hz，2H，CH 2)；2.49(s，3H，CH 3)；3.07(s，2H，CH 2)；3.87(s，3H，OCH 3)；6.98(s，H，C 6H 2)；6.99(s，H，C 6H 2)；10.77(s，H，NH)。
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 85.7%, m.p.165 ~ 168 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.45 (t, J=7.2Hz, 3H, CH 3), 1.54 (s, 6H, 2 × CH 3), 3.06 (s, 2H, CH 2), 4.20 (q, J=6.8Hz, 2H, CH 2), 6.18 (s, H, CH), 7.04 (s, H, C 6h 2), 7.24 (s, H, C 6h 2), 7.26 (s, H, thiazole-H).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, yield 85.2%, m.p.165 ~ 166 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.29 (dd, J=7.2Hz, 6H, 2 × CH 3); 1.42 (t, J=6.8Hz, 3H, CH 3); 1.53 (s, 6H, 2 × CH 3); 3.05 (s, 2H, CH 2); 3.10 ~ 3.12 (m, H, CH); 4.20 (q, J=6.8Hz, 2H, CH 2); 6.92 (s, H, C 6h 2); 7.19 (s, H, C 6h 2); 7.21 (s, H, thiazole-H); 10.05 (s, H, NH).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 80.6%, m.p.134 ~ 135 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.02 (t, J=7.2Hz, 3H, CH 3); 1.34 (t, J=6.8Hz, 3H, CH 3); 1.53 (s, 6H, 2 × CH 3); 1.68 (m, 2H, CH 2); 2.34 (t, 2H, CH 2); 3.05 (s, 2H, CH 2); 4.05 (q, J=6.8Hz, 2H, OCH 2); 6.93 (s, H, C 6h 2); 7.22 (s, H, C 6h 2); 7.26 (s, H, thiazole-H); 9.43 (s, H, NH).
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, yield 73.4%, m.p.150 ~ 151 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.46 (t, J=6.8Hz, 3H, CH 3); 1.53 (s, 6H, 2 × CH 3); 1.85 (s, 2H, CH 2); 2.25 (s, 2H, CH 2); 3.05 (s, 2H, CH 2); 3.56 (s, 2H, CH 2); 4.17 (t, J=6.8Hz, 2H, OCH 2); 6.95 (s, H, C 6h 2); 7.22 (s, H, C 6h 2); 7.22 (s, H, thiazole-H); 10.15 (s, H, NH).
N-[5-methyl-4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 87.0%, m.p.185 ~ 186 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.45(t，J＝7.2Hz，3H，CH 3)，1.54(s，6H，2×CH 3)，2.51(s，3H，CH 3)，3.07(s，2H，CH 2)，4.17(q，J＝7.2Hz，2H，OCH 2)，6.08(s，H，CH)，6.97(s，H，C 6H 2)，6.98(s，H，C 6H 2)。
N-[5-methyl-4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 82.0%, m.p.125 ~ 126 DEG C. 1HNMR(CDCl 3，400MHz)δ：0.87(t，J＝7.6Hz，3H，CH 3)；1.43(t，J＝7.6Hz，3H，CH 3)；1.53(s，6H，2×CH 3)；1.59～1.64(m，2H，CH 2)；2.11(t，J＝7.6Hz，2H，CH 2)；2.48(s，3H，CH 3)；3.05(s，2H，CH 2)；4.11～4.17(q，J＝7.6Hz，2H，CH 2)；6.96(s，H，C 6H 2)；6.97(s，H，C 6H 2)；11.71(s，H，NH)。
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 87.0%, m.p.142 ~ 144 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.04 (t, J=7.2Hz, 3H, CH 3), 1.53 (s, 6H, 2 × CH 3), 1.86 ~ 1.88 (m, 2H, CH 2), 3.06 (s, 2H, CH 2), 4.09 (t, J=6.4Hz, 2H, OCH 2), 4.20 (q, J=6.4Hz, 2H, CH 2), 6.18 (s, H, CH), 7.04 (s, H, C 6h 2), 7.24 (s, H, C 6h 2), 7.26 (s, H, thiazole-H).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 81.3%, m.p.104 ~ 105 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 0.90 (t, J=7.6Hz, 3H, CH 3); 1.00 (t, J=6.8Hz, 3H, CH 3); 1.52 (s, 6H, 2 × CH 3); 1.68 (m, 2H, CH 2); 1.85 (m, 2H, CH 2); 2.25 (t, J=6.8Hz, 2H, CH 2); 3.04 (s, 2H, CH 2); 4.05 (t, J=6.8Hz, 2H, OCH 2); 6.94 (s, H, C 6h 2); 7.21 (s, H, C 6h 2); 7.21 (s, H, thiazole-H); 10.19 (s, H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, yield 85.2%, m.p.111 ~ 112 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.04 (t, J=5.2Hz, 3H, CH 3); 1.30 (d, J=6.8Hz, 6H, 2 × CH 3); 1.53 (s, 6H, 2 × CH 3); 1.86 (m, 2H, CH 2); 2.70 (q, J=6.8Hz, H, CH); 3.05 (s, 2H, CH 2); 4.09 (t, J=6.8Hz, 2H, OCH 2); 6.89 (s, H, C 6h 2); 7.14 (s, H, C 6h 2); 7.16 (s, H, thiazole-H); 10.88 (s, H, NH).
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, yield 78.0%, m.p.102 ~ 103 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.02 (t, J=8.0Hz, 3H, CH 3); 1.53 (s, 6H, 2 × CH 3); 1.84 ~ 1.86 (m, 2H, CH 2); 2.25 (m, 2H, CH 2); 2.54 (t, 2H, CH 2); 3.05 (s, 2H, CH 2); 3.58 (t, 2H, CH 2); 4.06 (t, J=7.2Hz, 2H, OCH 2); 6.94 (s, H, C 6h 2); 7.22 (s, H, C 6h 2); 7.42 (s, H, thiazole-H); 10.14 (s, H, NH).
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 80%, m.p.150 ~ 152 DEG C. 1HNMR(CDCl 3，400MHz)δ：0.96(t，J＝8.0Hz，3H，CH 3)，1.33(t，J＝8.0Hz，3H，CH 3)，1.52(s，6H，2×CH 3)，1.60(s，3H，COCH 3)，1.77～1.83(m，2H，CH 2)，2.90(q，J＝8.0Hz，2H，CH 2)，3.03(s，2H，CH 2)，3.99(t，J＝8.0Hz，2H，CH 2)，6.92～6.94(m，2H，C 6H 2)，11.76(s，1H，NH)。
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 85.5%, m.p.118 ~ 119 DEG C. 1HNMR(CDCl 3，400MHz)δ：0.92～1.08(m，6H，2×CH 3)，1.32(t，J＝8.0Hz，3H，CH 3)，1.52(s，6H，2×CH 3)，1.78～1.88(m，4H，2×CH 2)，2.90(q，J＝8.0Hz，2H，CH 2)，3.04(s，2H，CH 2)，4.01(t，J＝8.0Hz，2H，CH 2)，6.92～6.94(m，2H，C 6H 2)，11.33(s，1H，NH)。
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, yield 89.9%, m.p.120 ~ 121 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.01(t，J＝7.6Hz，3H，CH 3)，1.34(t，J＝7.6Hz，3H，CH 3)，1.53(s，6H，2×CH 3)，1.82～1.87(m，2H，CH 2)，2.92(q，J＝7.2Hz，2H，CH 2)，3.06(s，2H，CH 2)，4.05(t，J＝7.2Hz，2H，OCH 2)，6.00(s，H，CH)，6.92(s，H，C 6H 2)，6.94(s，H，C 6H 2)。
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, yield 81.3%, m.p.131 ~ 132 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.01(t，J＝7.2Hz，3H，CH 3)；1.33(t，J＝7.2Hz，3H，CH 3)；1.53(s，6H，2×CH 3)；1.83(m，2H，CH 2)；2.91(q，J＝7.6Hz，2H，CH 2)；3.05(s，2H，CH 2)；4.04(t，J＝6.8Hz，2H，OCH 2)；4.10(s，2H，CH 2)；6.92(s，H，CH)；6.93(s，H，C 6H 2)；6.98(s，H，C 6H 2)。
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, yield 83.0%, m.p.144 ~ 145 DEG C. 1HNMR(CDCl 3，400MHz)δ：1.02(t，J＝7.6Hz，3H，CH 3)；1.34(t，J＝7.6Hz，3H，CH 3)；1.53(s，6H，2×CH 3)；1.84(m，2H，CH 2)；2.08(s，3H，CH 3)；2.93(q，J＝7.6Hz，2H，CH 2)；3.05(s，2H，CH 2)；4.05(t，J＝7.2Hz，2H，OCH 2)；5.63(s，1H，CH)；6.04(s，1H，CH)；6.92(s，H，C 6H 2)；6.94(s，H，C 6H 2)；9.68(s，H，NH)。
N-[5-ethyl-4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, yield 80.7%, m.p.70 ~ 72 DEG C. 1HNMR(CDCl 3，400MHz)δ：0.82(t，J＝6.4Hz，3H，CH 3)；0.98(t，J＝7.6Hz，3H，CH 3)；1.33(t，J＝7.6Hz，3H，CH 3)；1.53(s，6H，2×CH 3)；1.55(m，2H，CH 2)；1.82(m，2H，CH 2)；1.98(t，2H，CH 2)；2.88～2.94(q，J＝7.2Hz，2H，CH 2)；3.04(s，2H，CH 2)；4.01(t，J＝6.8Hz，2H，CH 2)；6.93～6.94(s，2H，C 6H 2)；10.88(s，1H，NH)。
N-[4-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, yield 85.5%, m.p.187 ~ 188 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.49 (s, 6H, 2 × CH 3), 2.01 (s, 3H, CH 3), 3.04 (s, 2H, CH 2), 6.76 (d, J=8.0Hz, 1H, C 6h 2), 6.94 (s, H, thiazole-H), 7.56 (s, H, C 6h 2), 7.58 (s, H, C 6h 2).
N-[4-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, yield 76.7%, m.p.100 ~ 101 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.50 (s, 6H, 2 × CH 3); 1.84 (d, J=7.2Hz, 3H, CH 3); 3.05 (s, 2H, CH 2); 4.62 (q, J=7.2Hz, H, CH); 6.76 (d, J=8.2Hz, H, C 6h 3); 7.00 (s, H, C 6h 3); 7.58 (d, J=8.2Hz, H, C 6h 3); 7.62 (s, H, thiazole-H); 9.93 (s, H, NH).
N-[4-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, yield 81.5%, m.p.109 ~ 111 DEG C. 1hNMR (CDCl 3, 400MHz) and δ: 1.21 (t, J=6.8Hz, 3H, CH 3); 1.50 (s, 6H, 2 × CH 3); 2.43 (q, J=6.8Hz, 2H, CH 2); 3.05 (s, 2H, CH 2); 6.76 (d, J=6.8Hz, H, C 6h 3); 6.96 (d, J=6.8Hz, H, C 6h 3); 7.50 (s, H, C 6h 3); 7.52 (s, H, thiazole-H); 10.80 (s, H, NH).
N-[4-(chloro-2,2-dimethyl-2, the 3-Dihydrobenzofuranes-5-bases of 7-) thiazol-2-yl] acetamide, yield 82.6%, m.p.230 ~ 231 DEG C; 1hNMR (CDCl 3, 400MHz) and δ: 1.55 (s, 6H, 2 × CH 3), 2.14 (s, 3H, CH 3), 3.11 (s, 2H, CH 2), 6.97 (s, H, thiazole-H), 7.47 (s, H, C 6h 2), 7.60 (s, H, C 6h 2).
Embodiment 2 application test:
The insecticidal activity assay of N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide
1 for examination target
Black bean aphid (Aphisfabae) is indoor with broad bean seedling raising sensitive strain for many years, if test is 3 age in days aphids with worm; Two-spotted spider mite (Tetranychusurticae) is indoor with broad bean seedling raising sensitive strain for many years.Testing with worm is healthy one-tenth mite.
2 condition of culture
Condition of culture for examination target and the rear target of test is temperature 25 ± 5 DEG C, relative moisture 65 ± 5%, periodicity of illumination 12/12h (L/D).
The 3 former medicine of tests (N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide preferred compound):
N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide.
4 former medicine preparation medicaments: take a certain amount of former medicine with ten thousand/electronic balance; Solvent: DMF (DMF), 0.2%; Emulsifier: Tween80,0.2%; Add clear water and be diluted to 500ppm ~ 1000ppm concentration.
5 test methods are with reference to " pesticide bioactivity evaluates SOP ".
The general sieve of black bean aphid adopts infusion process.If the broad bean seedling with 3 age in days broad bean aphids is cut, flood in the liquid prepared after 10 seconds and take out, be inserted into and suction on the sponge of water, cover the lampshade that starts, often process 2 times and repeat.Be disposed, be put in observation ward and cultivate, timing is observed, and checks and record death condition after 72h, calculates lethality.
Two-spotted spider mite adopts infusion process.Broad bean seedling with two spotted spider mite is cut, soaks in the liquid prepared and take out for 10 seconds, suck liquid unnecessary around plant and mite body with filter paper, be inserted on the beaker that sealed of dress water, often process and repeat for 2 times.Be disposed, be put in observation ward and cultivate, timing is observed, and checks and record death condition after 72h, calculates lethality.
6 cytotoxicities
When active ingredient concentration is 500mg/L, after process 72h, the cytotoxicity of preferred compound is listed in table 1 and table 2:
The killing aphids of table 1N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide is active
That shows 2N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide kills two spotted spider mite activity
N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide Lethality/%
N-[4-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide 57.2
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide 51.0
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide 78.4
N-[4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide 89.0
N-[4-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide 51.7
N-[5-methyl-4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide 58.0
The desinsection result display of table 1 and table 2: N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide has insecticidal activity, can be used as and applies preparing in insecticide.

Claims (2)

1. N-[4-(benzofuran-5-base) thiazol-2-yl] application of fatty acid amide in the insecticide preparing killing aphids or two spotted spider mite shown in chemical structural formula I:
Wherein, Y is selected from: hydrogen, deuterium, C 1~ C 2alkoxyl, C 3~ C 4unbranched alkoxy or branched alkoxy; R is selected from: hydrogen, deuterium, C 1~ C 2alkyl, C 3~ C 6straight chained alkyl or branched alkyl; R 1be selected from: hydrogen, deuterium, C 1~ C 2alkyl; R 2be selected from: C 1~ C 2alkyl, C 1~ C 2chloro alkyl, C 3~ C 5chloro straight chained alkyl or chloro branched alkyl; C 3~ C 17straight chained alkyl or branched alkyl; C 2~ C 6thiazolinyl.
2. application according to claim 1, N-[4-(benzofuran-5-base) thiazol-2-yl] fatty acid amide shown in its Chinese style I is selected from: N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] propionamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] dichloro acetamide, N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-Methacrylamide, N-[5-ethyl-4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] chloroacetamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-propoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-2-chlorine propionamide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl]-4-chlorobutamide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide, N-[4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] butyramide, N-[4-(7-ethyoxyl-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] isobutyramide or N-[5-methyl-4-(7-methoxyl group-2, 2-dimethyl-2, 3-Dihydrobenzofuranes-5-base) thiazol-2-yl] acetamide.
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