CN102010408A - 3- [4- (benzofuran-5-yl) thiazole-2-yl ] -2-methylbenzimidazole-5-formic ether and preparation method and application thereof - Google Patents
3- [4- (benzofuran-5-yl) thiazole-2-yl ] -2-methylbenzimidazole-5-formic ether and preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 title 1
- -1 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate Chemical compound 0.000 claims abstract description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000575 pesticide Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 abstract description 6
- 230000000749 insecticidal effect Effects 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HUOIDCCHUGUZQS-UHFFFAOYSA-N ethyl 3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CNC2=C1 HUOIDCCHUGUZQS-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- KRXJQVYCIGDILC-UHFFFAOYSA-N 1-(1-benzofuran-5-yl)-2-bromoethanone Chemical compound BrCC(=O)C1=CC=C2OC=CC2=C1 KRXJQVYCIGDILC-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 0 CC(C)(C1)Oc(c(O*)c2)c1cc2-c1c[s]c(-[n]2c(cc(cc3)C(O*)=O)c3nc2C)n1 Chemical compound CC(C)(C1)Oc(c(O*)c2)c1cc2-c1c[s]c(-[n]2c(cc(cc3)C(O*)=O)c3nc2C)n1 0.000 description 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
- ZWRLWJAFBLTMSQ-UHFFFAOYSA-N Docosa-7,10,14-triensaeure Natural products C1C(C)=C2CC(C)(C)CC2C(O)C2=COC=C21 ZWRLWJAFBLTMSQ-UHFFFAOYSA-N 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- YKASHPSKFYVZRC-UHFFFAOYSA-M furan-2-ylmethyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CC1=CC=CO1 YKASHPSKFYVZRC-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了化学结构式I所示的3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯：
Description
技术领域technical field
本发明涉及一类新化合物及其制备方法和应用，具体是3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯及其制备方法和应用。The present invention relates to a class of novel compounds and their preparation methods and applications, specifically 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate And its preparation method and application.
背景技术Background technique
邵玲等描述了4-芳基-5-三唑基噻唑-2-亚胺类化合物，生物活性测定结果表明部分化合物对苹果轮纹菌具有杀菌活性(高等学校化学学报，2007，28，270)。Michael等描述了2-氨基噻唑类乳腺癌药物(Bioorg & Med.Chem.2004，12，1029)；姜凤超等描述了对细胞凋亡有抑制活性的4-芳基噻唑-2-亚胺衍生物(药学学报，2006，41：727)。Lin等描述了西佛碱类化合物对COX-2具有选择性抑制作用(Bioorg & Med Chem，2008，16(5)：2697)。何道航等描述了4-芳基-2-(2-羟苄亚氨基)噻唑的合成与杀菌活性[华南理工大学学报自然科学版，2008，(3)：60]；中国专利(CN 101602761，CN 200910226728.5)描述了4-叔丁基-5-(1，2，4-三唑-1-基)-2-苄亚氨基噻唑的杀菌活性和抗肿瘤活性；胡艾希等描述了5-苄基-4-叔丁基-2-苄亚氨基噻唑的合成与环氧合酶-2活性[湖南大学学报自然科学版，2009，36(2)，70-74；中国专利，CN 101492426]和抗肿瘤活性[CN 200910226774.5，CN 101781269]。胡艾希等描述了2-甲基-1-(4-芳基噻唑-2-基)-苯并咪唑-6-甲酸乙酯合成与杀菌活性(高等学校化学学报，2008，29，739)。3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯及制备方法与和生物活性没有研究和开发报道。Shao Ling et al. described 4-aryl-5-triazolylthiazole-2-imine compounds, and the results of biological activity assays showed that some compounds had bactericidal activity against P. ). Michael et al. described 2-aminothiazole breast cancer drugs (Bioorg & Med.Chem.2004, 12, 1029); Jiang Fengchao et al. described 4-arylthiazole-2-imine derivatives with inhibitory activity on apoptosis (Acta Pharmacologica Sinica, 2006, 41:727). Lin et al. described the selective inhibitory effect of Schiff bases on COX-2 (Bioorg & Med Chem, 2008, 16(5): 2697). He Daohang et al. described the synthesis and bactericidal activity of 4-aryl-2-(2-hydroxybenzimino)thiazole [Journal of South China University of Technology, Natural Science Edition, 2008, (3): 60]; Chinese patent (CN 101602761, CN 200910226728.5) described the bactericidal activity and antitumor activity of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benziminothiazole; Hu Aixi et al. described 5-benzyl- Synthesis of 4-tert-butyl-2-benziminothiazole and cyclooxygenase-2 activity [Journal of Hunan University, Natural Science Edition, 2009, 36(2), 70-74; Chinese patent, CN 101492426] and antitumor Activity [CN 200910226774.5, CN 101781269]. Hu Aixi et al. described the synthesis and fungicidal activity of ethyl 2-methyl-1-(4-arylthiazol-2-yl)-benzimidazole-6-carboxylate (Chemical Journal of Chinese Universities, 2008, 29, 739). There is no research and development report on 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate, its preparation method and biological activity.
本发明将农药药效基呋喃酚、苯并咪唑与噻唑拼合在同一分子中，设计制备了3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯新型化合物。The present invention integrates the pesticide pharmacophore furanol, benzimidazole and thiazole into the same molecule, and designs and prepares 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzo Novel compound of imidazole-5-carboxylate.
发明内容Contents of the invention
本发明的目的在于提供化学结构式I所示的3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯。3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯化学名为3-[4-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)噻唑-2-基]-2-甲基-3H-苯并咪唑-5-甲酸酯。The object of the present invention is to provide 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate represented by chemical structural formula I. The chemical name of 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate is 3-[4-(7-methoxy-2 ,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]-2-methyl-3H-benzimidazole-5-carboxylate.
其中，R和R1选自：H，C1～C2烷基，C3～C4直链烷基或支链烷基。Wherein, R and R 1 are selected from: H, C 1 -C 2 alkyl, C 3 -C 4 straight-chain or branched-chain alkyl.
本发明的目的在于还提供了3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯的制备方法，其制备包括如下步骤：The object of the present invention is to also provide the preparation method of 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-formic acid ester, its preparation comprises the following step:
(1)1-(7-羟基/烷氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮、乙醇搅拌，回流，分批加入溴化铜，反应2～4h，制得2-溴-1-(苯并呋喃-5-基)乙酮；制备按如下反应式进行：(1) Stir 1-(7-hydroxy/alkoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone and ethanol, reflux, add copper bromide in batches , and reacted for 2 to 4 hours to obtain 2-bromo-1-(benzofuran-5-yl)ethanone; the preparation is carried out according to the following reaction formula:
R选自：H，C1～C2烷基，C3～C4直链烷基或支链烷基。R is selected from: H, C 1 -C 2 alkyl, C 3 -C 4 straight-chain or branched-chain alkyl.
(2)2-溴-1-(7-羟基/烷氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮、N-(2-乙酰氨基-5-烷氧羰基苯基)硫脲、丙酮，加热，搅拌反应2h，过滤，滤饼用浓氨水中和至碱性，制得3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯；制备按如下反应式进行：(2) 2-bromo-1-(7-hydroxyl/alkoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, N-(2-acetylamino -5-alkoxycarbonylphenyl)thiourea, acetone, heating, stirring for 2h, filtering, and neutralizing the filter cake with concentrated ammonia water to alkalinity to obtain 3-[4-(benzofuran-5-yl)thiazole -2-yl]-2-methylbenzimidazole-5-formic acid ester; Preparation is carried out according to the following reaction formula:
R和R1选自：H，C1～C2烷基，C3～C4直链烷基或支链烷基。R and R 1 are selected from: H, C 1 -C 2 alkyl, C 3 -C 4 straight-chain or branched-chain alkyl.
本发明的目的在于提供的3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯具有杀虫活性。The object of the present invention is to provide 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate with insecticidal activity.
本发明与现有技术相比具有如下优点：Compared with the prior art, the present invention has the following advantages:
1.本发明首次设计并制备了3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯。1. The present invention designs and prepares 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate for the first time.
2.3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯可用于制备杀虫剂。2.3-[4-(Benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate can be used to prepare insecticides.
具体实施方式Detailed ways
[0000]以下实施例旨在说明本发明而不是对本发明的进一步限定。[0000] The following examples are intended to illustrate the present invention rather than further limiting the invention.
实施例1 3-[4-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)噻唑-2-基]-2-甲基-3H-苯并咪唑-5-甲酸乙酯的制备Example 1 3-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]-2-methyl-3H -The preparation of ethyl benzimidazole-5-formate
(1)2-溴-1-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮的制备(1) Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone
0.02mol 1-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮、80mL乙醇，搅拌回流，分批加入0.04mol溴化铜，反应2h，反应液趁热过滤，蒸馏回收溶剂，乙酸乙酯溶解，稀酸洗涤，过滤，滤液经水洗，分液，干燥，乙醇重结晶得2-溴-1-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮，产率50.0％，熔点90～91℃。0.02mol 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 80mL ethanol, stirring and reflux, add 0.04mol copper bromide in batches , reacted for 2h, filtered the reaction solution while it was hot, recovered the solvent by distillation, dissolved ethyl acetate, washed with dilute acid, filtered, washed the filtrate with water, separated, dried, and recrystallized from ethanol to obtain 2-bromo-1-(7-methoxy -2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, yield 50.0%, melting point 90-91°C.
(2)N-(2-乙酰氨基-5-乙氧羰基苯基)硫脲的制备(2) Preparation of N-(2-acetylamino-5-ethoxycarbonylphenyl)thiourea
1.92g硫氰酸铵，20mL丙酮，搅拌，滴加2.96g苯甲酰氯，滴毕，回流30min。加入4.44g 3，80mL丙酮，继续回流5h。加60mL氨水，搅拌，回流0.5h.室温搅拌20min。过滤，甲醇洗，干燥得4.93g白色片状固体N-(2-乙酰氨基-5-乙氧羰基苯基)硫脲，收率82.8％，m.p.199～200℃。1H NMR(DMSO-d6)，δ：1.33(t，J＝7.2Hz，3H，CH3)，2.13(s，3H，COCH3)，4.30(q，J＝7.2Hz，2H，CH2)，7.75(dd，J＝8.4Hz，J＝1.6Hz，1H，C6H36-H)，7.81(d，J＝8.4Hz，1H，C6H35-H)，8.02(s，1H，NH)，8.27(d，J＝4.0Hz，1H，C6H32-H)，8.98(s，1H，NH)，9.67(s，1H，NH)。MS(m/z)：281(M+)，247，222，206，178，160，135，105，78，60。1.92g of ammonium thiocyanate and 20mL of acetone were stirred, and 2.96g of benzoyl chloride was added dropwise, and the solution was refluxed for 30min. Add 4.44g of 3, 80mL of acetone, continue to reflux for 5h. Add 60mL ammonia water, stir, and reflux for 0.5h. Stir at room temperature for 20min. Filter, wash with methanol, and dry to obtain 4.93 g of white flaky solid N-(2-acetylamino-5-ethoxycarbonylphenyl)thiourea, yield 82.8%, mp 199-200°C. 1 H NMR (DMSO-d 6 ), δ: 1.33 (t, J=7.2Hz, 3H, CH 3 ), 2.13 (s, 3H, COCH 3 ), 4.30 (q, J=7.2Hz, 2H, CH 2 ), 7.75(dd, J=8.4Hz, J=1.6Hz, 1H, C 6 H 3 6-H), 7.81(d, J=8.4Hz, 1H, C 6 H 3 5-H), 8.02(s , 1H, NH), 8.27 (d, J = 4.0 Hz, 1H, C 6 H 3 2-H), 8.98 (s, 1H, NH), 9.67 (s, 1H, NH). MS (m/z): 281 (M + ), 247, 222, 206, 178, 160, 135, 105, 78, 60.
(3)3-[4-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)噻唑-2-基]-2-甲基-3H-苯并咪唑-5-甲酸乙酯的制备(3) 3-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]-2-methyl-3H -The preparation of ethyl benzimidazole-5-formate
2.0mmol 2-溴-1-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)乙酮和2.0mmolN-(2-乙酰氨基-5-乙氧羰基苯基)硫脲，20mL丙酮，加热搅拌，反应2h，反应液冷却析出固体，过滤，滤饼氨水中和，制得3-[4-(7-甲氧基-2，2-二甲基-2，3-二氢苯并呋喃-5-基)噻唑-2-基]-2-甲基-3H-苯并咪唑-5-甲酸乙酯，收率79.7％，熔点153.0～154.1℃。1H NMR(CDCl3，300MHz)，δ：1.42(t，J＝7.2Hz，3H，CH3)，1.56(s，6H，2×CH3)，2.93(s，3H，苯并咪唑环2-CH3)，3.11(s，2H，CH2)，3.95(s，3H，OCH3)，4.31(q，J＝7.2Hz，2H，CH2)，7.23～7.45(m，3H，噻唑环5-H，C6H2)，7.82(d，J＝7.2Hz，1H，苯并咪唑环7-H)，8.12(d，J＝7.2Hz，1H，苯并咪唑环6-H)，8.47(s，1H，苯并咪唑环4-H)；EI-MS(m/z)：464.2(M+)。2.0mmol 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone and 2.0mmolN-(2-acetylamino-5 -Ethoxycarbonylphenyl)thiourea, 20mL acetone, heated and stirred, reacted for 2h, the reaction solution was cooled to precipitate a solid, filtered, and the filter cake was neutralized with ammonia water to obtain 3-[4-(7-methoxy-2,2 -Dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]-2-methyl-3H-benzimidazole-5-ethyl carboxylate, yield 79.7%, melting point 153.0 ~154.1°C. 1 H NMR (CDCl 3 , 300MHz), δ: 1.42(t, J=7.2Hz, 3H, CH 3 ), 1.56(s, 6H, 2×CH 3 ), 2.93(s, 3H, benzimidazole ring 2 -CH 3 ), 3.11 (s, 2H, CH 2 ), 3.95 (s, 3H, OCH 3 ), 4.31 (q, J=7.2Hz, 2H, CH 2 ), 7.23～7.45 (m, 3H, thiazole ring 5-H, C 6 H 2 ), 7.82 (d, J=7.2Hz, 1H, benzimidazole ring 7-H), 8.12 (d, J=7.2Hz, 1H, benzimidazole ring 6-H), 8.47 (s, 1H, benzimidazole ring 4-H); EI-MS (m/z): 464.2 (M + ).
实施例2 3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯对蚜虫的毒杀测定Example 2 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-formic acid ester is toxic to aphids
通过高通量体内活性筛选(UHTVS)，测试了3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯在浓度为30mg/L和6mg/L对桃蚜(MYZUPE)虫卵毒杀均有效。3-[4-(苯并呋喃-5-基)噻唑-2-基]-2-甲基苯并咪唑-5-甲酸酯具有良好的杀虫活性，可作为制备杀虫剂在农业上应用。Through high-throughput in vivo activity screening (UHTVS), tested 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate at a concentration of Both 30mg/L and 6mg/L are effective in poisoning the eggs of green peach aphid (MYZUPE). 3-[4-(benzofuran-5-yl)thiazol-2-yl]-2-methylbenzimidazole-5-carboxylate has good insecticidal activity and can be used as a preparation of insecticides in agriculture application.
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| CN109180667B (en) * | 2018-09-10 | 2021-08-06 | 湖南大学 | 8-(benzofuran-5-yl)benzoxazinone derivatives and their applications |
| CN111978306A (en) * | 2019-05-24 | 2020-11-24 | 湖南大学 | Furanol pyrazole formamide derivative and preparation method and application thereof |
| CN111978306B (en) * | 2019-05-24 | 2023-01-03 | 湖南大学 | Furanol pyrazole formamide derivative and preparation method and application thereof |
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