5-硝基亚氨基[1,4-2H]-1,2,4-三唑啉烯式吡虫啉类似物的合成及生物活性研究

doi:10.6023/cjoc202302012

有机化学 ›› 2023, Vol. 43 ›› Issue (8): 2790-2799.DOI: 10.6023/cjoc202302012 上一篇下一篇

研究论文

5-硝基亚氨基[1,4-2H]-1,2,4-三唑啉烯式吡虫啉类似物的合成及生物活性研究

刘敏^a,†, 杨冬燕^b,†, 肖玉梅^a^,^*(), 苏旺苍^c, 赵峰海^a, 覃兆海^a^,^*()

a 中国农业大学理学院北京 100193
b 仲恺农业工程学院化学化工学院广州 510225
c 河南省农业科学院植物保护研究所郑州 450002

收稿日期:2023-02-12 修回日期:2023-04-04 发布日期:2023-06-26
作者简介:
†共同第一作者
基金资助:
国家重点研发计划(2016YFD0300709); 广州市科技计划(202102020214)

Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics

Min Liu^a,†, Dongyan Yang^b,†, Yumei Xiao^a(), Wangcang Su^c, Fenghai Zhao^a, Qin Zhaohai .^a()

a College of Science, China Agricultural University, Beijing, 100193
b College of Chemistry and Chemical Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou 510225
c Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou 450002

Received:2023-02-12 Revised:2023-04-04 Published:2023-06-26
Contact: *E-mail: qinzhaohai@263.net; xiaoyumei@cau.edu.cn
About author:
†These authors contributed equally to this work
Supported by:
The National Key Research and Development Plan of China(2016YFD0300709); The Guangzhou Science and Technology Plan(202102020214)

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摘要/Abstract

烯式吡虫啉是吡虫啉的高活性代谢产物. 为解决烯式吡虫啉的高蜂毒问题, 根据生物电子等排原理, 合成了一系列烯式吡虫啉的类似物1,3-二取代-5-硝基亚氨基三唑啉化合物, 研究了该系列化合物对蚜虫、褐飞虱和西花蓟马的杀虫活性和离体杀菌活性. 结果表明, 这些化合物在400 μg/mL浓度下表现出一定的杀虫活性, 其中化合物Ⅱ-7在100 μg/mL浓度对西花蓟马的致死率达100%. 用admetSAR预测了部分化合物对蜜蜂的毒性, 结果均表现为低毒. 目标化合物在50 μg/mL浓度下对9种植物病原真菌均表现出不同程度的抑菌活性, 其中化合物I-15对5种病原菌的抑菌率高于或等同于对照药恶霉灵. 构效关系分析发现, 3-位脂肪烃基取代的化合物的杀虫活性高于芳香烃取代, 提高3号位取代基的亲脂性也可明显提高化合物的抑菌活性, 1-位吡啶环和噻唑环的取代对化合物抑菌活性没有影响. 与乙酰胆碱结合蛋白(AchBP)的分子对接结果表明, 化合物Ⅱ-7与吡虫啉(IMI)的结合模式相似, 说明该类化合物也具有与AChBP结合的潜力, 为进一步分子优化提供了新的借鉴.

关键词: 生物电子等排, 5-硝基亚氨基-1,2,4-三唑, 杀虫活性, 抑菌活性, 分子对接

Olefin-imidacloprid is a highly active metabolite of imidacloprid. To solve the problem of high bee toxicity of olefin-imidacloprid, according to the bioisosterism, a series of novel olefin-imidacloprid mimics containing 1,3-disubstituted- 1,2,4-triazoline were designed and synthesized. The insecticidal activity of these compounds against A. craccivora, Nilaparvata lugens and F. occidentalis and in vitro antifungal activity were determined. The results showed that these compounds showed certain insecticidal activity at 400 μg/mL and 100% lethal rate was obtained from compound Ⅱ-7 at 100 μg/mL against F. occidentalis. The toxicity of some compounds to bees was predicted by admetSAR, and they showed low level of toxicity. On the other hand, the target compounds showed different degrees of antifungal activity against 9 plant pathogenic fungi at the concentration of 50 μg/mL. Compound I-15 exhibited the highest activity with the inhibition rate higher or equal to hymexazol against five pathogens. The structure-activity relationship analysis showed that the compounds bearing alkyl substituent at site 3 in triazoline unit displayed higher insecticidal activity than that of an aryl substitution, meanwhile, the more lipophilic groups, the higher fungicidal activity. The substitution of pyridine ring or thiazole ring at site 1 in triazoline unit had little effect on their antifungal activity. The molecular docking results showed that the binding pattern of compound Ⅱ-7 to acetylcholine binding protein (AChBP) was similar to that of imidacloprid (IMI), indicating that these compounds also had the potential to bind to AChBP, which provided a new reference for further molecular optimization.

Key words: bioisosterism, 5-nitroimine-1,2,4 triazoline, insecticidal activity, fungicidal activity, molecular docking

引用此文

刘敏, 杨冬燕, 肖玉梅, 苏旺苍, 赵峰海, 覃兆海. 5-硝基亚氨基[1,4-2H]-1,2,4-三唑啉烯式吡虫啉类似物的合成及生物活性研究[J]. 有机化学, 2023, 43(8): 2790-2799.

Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.

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参考文献 49

[1]	Elbert, A.; Becker, B.; Hartwig, J.; Erdelen, C. Pflanzenschutz- Nachr. Bayer 1991, 44, 113.
[2]	Casida, J. E.; Quistad, G. B. Annu. Rev. Entomol. 1998, 43, 1. pmid: 9444749
[3]	Jeschke, P.; Nauen, R. Pest Manage. Sci. 2008, 64, 1084. doi: 10.1002/ps.v64:11
[4]	Tomizawa, M.; Casida, J. E. Acc. Chem. Res. 2009, 42, 260. doi: 10.1021/ar800131p
[5]	Casida, J. E. J. Agric. Food Chem. 2011, 59, 2923. doi: 10.1021/jf102438c
[6]	Kagabu, S. J. Agric. Food Chem. 2011, 59, 2887. doi: 10.1021/jf101824y
[7]	Tomizawa, M.; Casida, J. E. J. Agric. Food Chem. 2011, 59, 2883. doi: 10.1021/jf103856c
[8]	Jeschke, P.; Nauen, R.; Beck, M. E. Angew. Chem., Int. Ed. 2013, 52, 9464. doi: 10.1002/anie.v52.36
[9]	Leite, S. A.; Guedes, R. N. C.; da Costa, D. R.; Colmenarez, Y. C.; Matsumoto, S. N.; dos Santos, M. P.; Coelho, B. S.; Moreira, A. A.; Castellani, M. A. Pest Manage. Sci. 2022, 78, 2581. doi: 10.1002/ps.v78.6
[10]	Alsafran, M.; Rizwan, M.; Usman, K.; Saleem, M. H.; Jabri, H. A. J. Environ. Chem. Eng. 2022, 10, 108485. doi: 10.1016/j.jece.2022.108485
[11]	Britt, E. E. Chem. Eng. News 2023, 101, 14.
[12]	Lourencetti, A. P. S.; Azevedo, P.; Miotelo, L.; Malaspina, O.; Nocelli, R. C. F. Environ. Pollut. 2023, 318, 120842. doi: 10.1016/j.envpol.2022.120842
[13]	European Food Safety, A. EFSA J. 2018, 16, e05178.
[14]	Demortain, D. Curr. Opin. Insect. Sci. 2021, 46, 78-82. doi: 10.1016/j.cois.2021.02.017 pmid: 33737144
[15]	Onozaki, Y.; Horikoshi, R.; Ohno, I.; Kitsuda, S.; Durkin, K. A.; Suzuki, T.; Asahara, C.; Hiroki, N.; Komabashiri, R.; Shimizu, R.; Furutani, S.; Ihara, M.; Matsuda, K.; Mitomi, M.; Kagabu, S.; Uomoto, K.; Tomizawa, M. J. Agric. Food Chem. 2017, 65, 7865. doi: 10.1021/acs.jafc.7b02924
[16]	Xu, Y.; Yang, D. Y.; Zou, X. G.; Rui, C. H.; Zhou, Z. Y.; Ma, Y. Q.; Qin, Z. H. Pest Manage. Sci. 2017, 73, 1927. doi: 10.1002/ps.2017.73.issue-9
[17]	Yang, S.; Lai, Q.; Lai, F.; Jiang, X.; Zhao, C.; Xu, H. Pest Manage. Sci. 2021, 77, 1013. doi: 10.1002/ps.v77.2
[18]	Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus- Kintscher, U.; Thielert, W.; Wolfel, K.; Haas, M.; Kunz, K.; Raupach, G. Pest Manage. Sci. 2015, 71, 850. doi: 10.1002/ps.2015.71.issue-6
[19]	Wernecke, A.; Eckert, J. H.; Forster, R.; Kurlemann, N.; Odemer, R. J. Plant Dis. Protect. 2021, 129, 93.
[20]	Tamburini, G.; Wintermantel, D.; Allan, M. J.; Dean, R. R.; Knauer, A.; Albrecht, M.; Klein, A. M. Sci. Total Environ. 2021, 778, 146084. doi: 10.1016/j.scitotenv.2021.146084
[21]	Jeschke, P.; Nauen, R.; Gutbrod, O.; Beck, M. E.; Matthiesen, S.; Haas, M.; Velten, R. Pest. Biochem. Physiol. 2015, 121, 31. doi: 10.1016/j.pestbp.2014.10.011
[22]	Zhu, C.; Li, G.; Xiao, K.; Shao, X.; Cheng, J.; Li, Z. Chin. Chem. Lett. 2019, 30, 255. doi: 10.1016/j.cclet.2018.05.013
[23]	Markussen, M. D. K.; Kristensen, M. Pest. Biochem. Physiol. 2010, 98, 50. doi: 10.1016/j.pestbp.2010.04.012
[24]	Kim, J.; Chon, K.; Kim, B.-S.; Oh, J.-A.; Yoon, C.-Y.; Park, H.-H. Pest Manage. Sci. 2022, 78, 5402. doi: 10.1002/ps.v78.12
[25]	Zhang, D.; Zhang, J.; Liu, T.; Wu, S.; Wu, Z.; Wu, S.; Song, R.; Song, B. J. Agric. Food Chem. 2022, 70, 8598. doi: 10.1021/acs.jafc.2c01899
[26]	Sur, R. B. Insectol. 2003, 56, 35.
[27]	Nauen, R.; Tietjen, K.; Wagner, K.; Elbert, A. Pestic. Sci. 1998, 52, 53. doi: 10.1002/(SICI)1096-9063(199801)52:1【-逻辑与-】amp;lt;【-逻辑与-】amp;gt;1.0.CO;2-J
[28]	Nauen, R.; Reckmann, U.; Armborst, S.; Stupp, H.-P.; Elbert, A. Pestic. Sci. 1999, 55, 265. doi: 10.1002/(SICI)1096-9063(199903)55:3【-逻辑与-】amp;lt;【-逻辑与-】amp;gt;1.0.CO;2-5
[29]	Liu, J.; Zhang, Y.; Dong, F.; Wu, X.; Pan, X.; Xu, J.; Zheng, Y. J. Sep. Sci. 2022, 45, 3567. doi: 10.1002/jssc.v45.18
[30]	Suchail, S.; Guez, D.; Belzunces, L. P. Environ. Toxicol. Chem. 2001, 20, 2482. doi: 10.1897/1551-5028(2001)020【-逻辑与-】lt;2482:dbaact【-逻辑与-】gt;2.0.co;2 pmid: 11699773
[31]	Jayashree, B. S.; Nikhil, P. S.; Paul, S. Med. Chem. 2022, 18, 915-925. doi: 10.2174/1573406418666220127124228
[32]	Kang, O.-Y.; Kim, E.; Lee, W. H.; Ryu, D. H.; Lim, H. J.; Park, S. J. RSC Adv. 2023, 13, 2004. doi: 10.1039/D2RA06988A
[33]	Wu, H.; Maimaitijiang, A.; Tang, D.; Xie, B.; Niu, C.; Aisa, H. A. Heterocycles 2023, 106, 94. doi: 10.3987/COM-22-14764
[34]	Guzel, E.; Acar Cevik, U.; Evren, A. E.; Bostanc, H. E.; Gul, U. D.; Kays, U.; Ozkay, Y.; Kaplanckl, Z. A. ACS Omega 2023, 8, 4369. doi: 10.1021/acsomega.2c07755
[35]	Li, J.; Zhang, J. Curr. Top. Med. Chem. 2022, 22, 41. doi: 10.2174/1568026621666211111160332
[36]	Gupta, O.; Pradhan, T.; Chawla, G. J. Mol. Struct. 2023, 1274, 134487. doi: 10.1016/j.molstruc.2022.134487
[37]	Xie, R.; Mei, X.; Ning, J. Chem. Pharm. Bull. 2019, 67, 345. doi: 10.1248/cpb.c18-00704
[38]	Li, B.; Yu, Y.; Duan, W.; Lin, G.; Wen, R.; Zhang, Z. Chem. Biodivers. 2022, 19, e202200726. doi: 10.1002/cbdv.v19.11
[39]	Zhao, F.; Singh, T.; Xiao, Y.; Su, W.; Yang, D.; Jia, C.; Li, J.-Q.; Qin, Z. Synthesis 2021, 53, 1901. doi: 10.1055/a-1477-4630
[40]	Ouyang, Y.; Huang, J.-j.; Wang, Y.-L.; Zhong, H.; Song, B.-A.; Hao, G.-f. J. Agric. Food Chem. 2021, 69, 10761. doi: 10.1021/acs.jafc.1c01460
[41]	Chen, D.; Hao, G.; Song, B. J. Agric. Food Chem. 2022, 70, 10090. doi: 10.1021/acs.jafc.2c02757
[42]	Banerjee, P.; Eckert, A. O.; Schrey, A. K.; Preissner, R. Nucleic Acids Res. 2018, 46, W257. doi: 10.1093/nar/gky318
[43]	Cheng, F.; Li, W.; Zhou, Y.; Shen, J.; Wu, Z.; Liu, G.; Lee, P. W.; Tang, Y. J. Chem. Inf. Model. 2012, 52, 3099. doi: 10.1021/ci300367a
[44]	Williams, A. J.; Grulke, C. M.; Edwards, J.; McEachran, A. D.; Mansouri, K.; Baker, N. C.; Patlewicz, G.; Shah, I.; Wambaugh, J. F.; Judson, R. S.; Richard, A. M. J. Cheminf. 2017, 9, 61/61-61/27.
[45]	Perez Santin, E.; Rodriguez Solana, R.; Gonzalez Garcia, M.; Garcia Suarez, M. D. M.; Blanco Diaz, G. D.; Cima Cabal, M. D.; Moreno Rojas, J. M.; Lopez Sanchez, J. I. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2021, 11, e1516.
[46]	Han, Q.; Wu, N.; Liu, Y.-Y.; Zhang, J.-Y.; Zhang, R.-L.; Li, H.-L.; Jiang, Z.-Y.; Huang, J.-X.; Duan, H.-X.; Yang, Q. J. Agric. Food Chem. 2022, 70, 7387. doi: 10.1021/acs.jafc.2c02091
[47]	Zhao, P.-L.; Wang, F.; Zhang, M.-Z.; Liu, Z.-M.; Huang, W.; Yang, G.-F. J. Agric. Food Chem. 2008, 56, 10767. doi: 10.1021/jf802343p
[48]	Su, W.; Zhou, Y.; Ma, Y.; Wang, L.; Zhang, Z.; Rui, C.; Duan, H.; Qin, Z. J. Agric. Food Chem. 2012, 60, 5028. doi: 10.1021/jf300616x
[49]	Wang, J.; Liu, X.; Zhang, X.; Du, S.; Han, X.; Li, J. Q.; Xiao, Y.; Xu, Z.; Wu, Q.; Xu, L.; Qin, Z. J. Agric. Food Chem. 2022, 70, 111. doi: 10.1021/acs.jafc.1c05784

Compd.	Honey bee toxicity	Compound	Honey bee toxicity	Compd.	Honey bee toxicity
Ⅰ-3	Low	Ⅱ-2	Low	7Ⅰ-19	Low
Ⅰ-7	Low	Ⅱ-5	Low	7Ⅰ-20	Low
Ⅰ-9	Low	Ⅱ-7	Low	3	High^[29-30]
Ⅰ-13	Low	Ⅱ-10	Low
Ⅰ-18	Low	Ⅱ-12	Low

Compd.	Honey bee toxicity	Compound	Honey bee toxicity	Compd.	Honey bee toxicity
Ⅰ-3	Low	Ⅱ-2	Low	7Ⅰ-19	Low
Ⅰ-7	Low	Ⅱ-5	Low	7Ⅰ-20	Low
Ⅰ-9	Low	Ⅱ-7	Low	3	High^[29-30]
Ⅰ-13	Low	Ⅱ-10	Low
Ⅰ-18	Low	Ⅱ-12	Low

Compd.	R²			R¹		A.craccivora/(μg•mL^－1)				N. lugens/(μg•mL^－1)			F. occidentalis/(μg•mL^－1)
Compd.	R²			R¹		400		100		400	100		400		100		50
Ⅰ-1				H		0		—		0	—		6.67		—		—
Ⅰ-2				CH₃		44		—		4.44	—		0		—		—
Ⅰ-3				C₂H₅		52.87		—		2.13	—		39.33		—		—
Ⅰ-4				n-Pr		41.77		—		4.35	—		8.33		—		—
Ⅰ-5				i-Pr		42.35		—		0	—		3.96		—		—
Ⅰ-6				n-Bu		26.25		—		0	—		91.09		0		—
Ⅰ-7				sec-Bu		22.62		—		0	—		2.27		—		—
Ⅰ-8				t-Bu		44.71		—		0	—		43.37		—		—
Ⅰ-9				n-Hexyl		62.9		—		6.25	—		3.88		—		—
Ⅰ-10				n-Octyl		0		—		2.13	—		9.09		—		—
Ⅰ-11						2.47		—		4.55	—		22.33		—		—
Ⅰ-12				4-ClC₆H₄		3.8		—		0	—		4.3		—		—
Ⅰ-13				4-CH₃C₆H₄		5.43		—		13.64	—		54.26		—		—
Ⅰ-14				4-CH₃OC₆H₄		0		—		0	—		64		—		—
Ⅰ-15				4-(CH₃)₃CC₆H₄		0		—		0	—		4.3		—		—
Ⅰ-16				C₆H₅		2.86		—		0	—		94.51		0		—
Ⅰ-17				3-NO₂C₆H₄		9.86		—		8.89	—		2.13		—		—
Ⅰ-18				4-CNC₆H₄		3.03		—		0	—		4.4		—		—
Ⅱ-1				H		0		—		0	—		0		—		—
Ⅱ-2				CH₃		86.25		0		0	—		10.42		—		—
Ⅱ-3				C₂H₅		58.02		—		2.17	—		45.26		—		—
Ⅱ-4				n-Pr		52.78		—		0	—		3.49		—		—
Ⅱ-5			i-Pr		4.11		—		0		—	25.53		—		—
Ⅱ-6			n-Bu		24.29		—		0		—	3.26		—		—
Ⅱ-7			sec-Bu		100		0		6.38		—	100		100		0
Ⅱ-8			t-Bu		28.79		—		0		—	80.23		0		—
Ⅱ-9			n-Hexyl		3.49		—		0		—	28.05		—		—
Ⅱ-10			n-Octyl		42.68		—		2.22		—	2.97		—		—
Ⅱ-11					4.84		—		13.64		—	4.3		—		—
Ⅱ-12			4-ClC₆H₄		2.44		—		2.17		—	0		—		—
7I-19		—	—		48.48		—		0		—	4.44		—		—
7I-20		—	—		2.41		—		46.51		—	0		—		—
3		—	—		100		100		97.78		41.3	100		100		100
Nitenpyram		—	—		100		—		—		—	—		—		—
Dinotefuran		—	—		—		100		100		100	—		—		97.56
Spinosad		—	—		—		—		—		—	100		100		—
DMF		—	—		4.76		1.06		0		0	0		4.9		2.35

Compd.	R²			R¹		A.craccivora/(μg•mL^－1)				N. lugens/(μg•mL^－1)			F. occidentalis/(μg•mL^－1)
Compd.	R²			R¹		400		100		400	100		400		100		50
Ⅰ-1				H		0		—		0	—		6.67		—		—
Ⅰ-2				CH₃		44		—		4.44	—		0		—		—
Ⅰ-3				C₂H₅		52.87		—		2.13	—		39.33		—		—
Ⅰ-4				n-Pr		41.77		—		4.35	—		8.33		—		—
Ⅰ-5				i-Pr		42.35		—		0	—		3.96		—		—
Ⅰ-6				n-Bu		26.25		—		0	—		91.09		0		—
Ⅰ-7				sec-Bu		22.62		—		0	—		2.27		—		—
Ⅰ-8				t-Bu		44.71		—		0	—		43.37		—		—
Ⅰ-9				n-Hexyl		62.9		—		6.25	—		3.88		—		—
Ⅰ-10				n-Octyl		0		—		2.13	—		9.09		—		—
Ⅰ-11						2.47		—		4.55	—		22.33		—		—
Ⅰ-12				4-ClC₆H₄		3.8		—		0	—		4.3		—		—
Ⅰ-13				4-CH₃C₆H₄		5.43		—		13.64	—		54.26		—		—
Ⅰ-14				4-CH₃OC₆H₄		0		—		0	—		64		—		—
Ⅰ-15				4-(CH₃)₃CC₆H₄		0		—		0	—		4.3		—		—
Ⅰ-16				C₆H₅		2.86		—		0	—		94.51		0		—
Ⅰ-17				3-NO₂C₆H₄		9.86		—		8.89	—		2.13		—		—
Ⅰ-18				4-CNC₆H₄		3.03		—		0	—		4.4		—		—
Ⅱ-1				H		0		—		0	—		0		—		—
Ⅱ-2				CH₃		86.25		0		0	—		10.42		—		—
Ⅱ-3				C₂H₅		58.02		—		2.17	—		45.26		—		—
Ⅱ-4				n-Pr		52.78		—		0	—		3.49		—		—
Ⅱ-5			i-Pr		4.11		—		0		—	25.53		—		—
Ⅱ-6			n-Bu		24.29		—		0		—	3.26		—		—
Ⅱ-7			sec-Bu		100		0		6.38		—	100		100		0
Ⅱ-8			t-Bu		28.79		—		0		—	80.23		0		—
Ⅱ-9			n-Hexyl		3.49		—		0		—	28.05		—		—
Ⅱ-10			n-Octyl		42.68		—		2.22		—	2.97		—		—
Ⅱ-11					4.84		—		13.64		—	4.3		—		—
Ⅱ-12			4-ClC₆H₄		2.44		—		2.17		—	0		—		—
7I-19		—	—		48.48		—		0		—	4.44		—		—
7I-20		—	—		2.41		—		46.51		—	0		—		—
3		—	—		100		100		97.78		41.3	100		100		100
Nitenpyram		—	—		100		—		—		—	—		—		—
Dinotefuran		—	—		—		100		100		100	—		—		97.56
Spinosad		—	—		—		—		—		—	100		100		—
DMF		—	—		4.76		1.06		0		0	0		4.9		2.35

Compd.	Inhibition rate/% (50 μg/mL)
Compd.	PA	BC	RS	PC	CG	FG	MG	FO	FM
Ⅰ-1	0.0±0.8	14.5±3.7	30.0±2.7	6.6±0.8	8.0±4.6	1.0±2.0	11.1±1.0	0.1±2.4	5.1±0.2
Ⅰ-2	0.0±1.8	11.2±1.6	20.5±2.0	0.6±0.8	5.9±3.1	12.1±4.1	6.8±1.4	1.0±0.5	2.4±1.4
Ⅰ-3	3.6±0.4	11.3±3.2	16.9±1.6	3.4±1.1	0.0±0.4	14.9±0.7	1.6±0.7	0.3±0.9	0.2±3.9
Ⅰ-4	0.0±0.9	13.3±1.1	11.6±3.7	0.0±1.4	11.8±0.8	13.6±8.8	4.1±0.3	2.3±4.2	1.3±3.3
Ⅰ-5	3.2±1.8	6.5±1.3	7.6±4.3	8.3±0.2	5.8±1.1	0.7±3.6	5.6±0.4	3.7±3.5	4.2±1.4
Ⅰ-6	4.8±0.8	10.7±2.8	14.0±1.6	15.5±1.1	13.3±0.6	0.0±1.2	5.4±1.2	0.1±0.3	2.4±1.6
Ⅰ-7	5.4±0.4	13.8±1.4	13.3±2.4	20.8±0.7	10.9±0.3	0.9±0.4	4.1±0.7	0.2±0.7	4.2±1.7
Ⅰ-8	12.3±2.7	14.8±1.0	10.4±4.6	11.5±1.6	6.1±3.1	0.0±0.2	6.2±1.2	5.4±1.4	6.8±4.9
Ⅰ-9	68.2±1.0	35.5±0.9	34.1±4.7	50.8±2.1	26.4±0.9	12.1±1.2	7.0±2.2	21.0±1.4	13.5±1.5
Ⅰ-10	89.4±0.1	25.2±3.0	33.1±2.2	48.7±2.4	18.2±3.8	9.2±1.3	20.2±0.5	4.9±2.7	54.9±1.9
Ⅰ-11	0.0±3.5	8.4±4.7	15.9±4.2	1.7±1.4	7.1±2.3	0.0±2.5	5.4±0.7	4.6±1.4	7.437±23
Ⅰ-12	69.7±0.9	20.4±1.3	31.8±3.5	10.5±3.4	0.0±1.4	9.2±3.9	6.1±3.4	13.3±1.9	42.1±1.0
Ⅰ-13	75.8±1.1	26.5±1.5	23.0±1.6	25.3±0.9	11.5±2.2	19.0±2.5	7.5±2.8	15.3±1.8	47.9±3.3
Ⅰ-14	45.7±3.9	16.7±2.9	19.3±1.7	14.8±2.2	0.0±1.4	17.7±1.5	5.8±0.7	8.7±2.7	32.2±2.5
Ⅰ-15	87.7±0.5	61.2±3.4	59.3±2.3	44.0±1.2	21.2±4.2	17.2±0.5	10.7±3.1	22.7±2.3	59.0±0.7
Ⅰ-16	0.0±0.8	15.5±3.5	21.0±1.9	6.3±0.7	3.7±0.9	8.8±2.1	10.4±1.2	5.4±0.4	37.6±1.6
Ⅰ-17	0.0±2.7	11.6±0.9	21.2±1.1	5.3±0.6	10.1±2.5	1.5±1.2	2.5±1.0	10.3±2.6	6.3±0.3
Ⅰ-18	0.0±2.2	10.8±2.6	23.9±3.7	0.0±0.7	4.7±4.6	9.5±2.1	4.9±1.8	1.5±1.7	36.1±4.5
Ⅱ-1	0.0±1.5	10.4±1.7	5.1±1.9	2.4±3.2	15.5±0.8	0.4±0.7	5.8±0.4	10.6±1.4	3.8±1.8
Ⅱ-2	2.0±2.0	6.1±4.7	12.4±3.4	0.9±0.7	16.8±0.4	4.1±2.4	3.3±0.7	4.5±3.8	1.5±2.2
Ⅱ-3	0.0±2.0	8.6±2.9	21.2±4.8	0.0±1.6	0.0±2.2	5.6±4.4	3.0±1.8	0.0±1.2	0.0±2.6
Ⅱ-4	3.6±0.6	13.2±4.0	14.9±3.4	10.9±2.6	7.2±1.4	9.1±1.5	6.5±0.9	0.0±0.4	4.2±0.7
Ⅱ-5	13.8±1.2	9.7±3.9	6.1±4.0	13.0±4.1	9.4±3.2	21.9±2.7	4.9±0.4	3.6±1.7	13.7±0.7
Ⅱ-6	23.1±1.5	20.1±3.8	6.4±1.6	27.9±1.7	9.5±2.5	6.4±0.8	36.3±4.3	8.4±1.2	44.9±3.5
Ⅱ-7	12.4±1.7	13.6±0.2	18.9±4.3	11.7±4.6	10.9±3.2	0.0±2.0	3.1±0.5	1.1±1.4	7.0±0.3
Ⅱ-8	9.4±0.8	13.7±3.7	10.4±1.6	20.1±2.0	0.0±0.3	0.0±3.7	6.4±0.5	3.2±1.4	8.9±2.2
Ⅱ-9	64.8±0.2	48.9±1.6	45.5±2.0	34.4±3.2	12.8±2.4	6.6±1.4	11.8±0.7	22.8±1.8	12.1±4.0
Ⅱ-10	90.0±0.7	41.7±4.1	52.4±2.8	54.1±1.4	17.5±2.0	13.4±2.4	24.0±1.1	6.8±4.7	46.5±8.7
Ⅱ-11	2.3±2.8	5.6±0.6	19.2±3.7	2.3±1.7	5.8±0.3	0.0±0.3	9.6±4.9	3.3±1.1	1.1±1.6
Ⅱ-12	86.9±1.3	34.7±1.8	46.6±1.6	16.2±1.1	0.0±0.6	4.8±2.1	10.3±1.0	0.0±2.6	45.6±5.0
7Ⅰ-19	10.2±1..0	17.3±3.8	25.3±3.7	27.5±1.1	10.9±3.8	2.8±1.0	10.9±0.5	9.7±2.8	9.7±1.1
7Ⅰ-20	8.7±1.5	0.4±1.8	52.4±2.8	6.1±2.6	11.4±4.7	0.8±1.6	4.7±0.0	5.5±0.9	2.0±2.1
3	0.0±3.8	9.4±4.6	2.3±3.9	0.0±1.2	15.7±1.1	0.0±0.5	5.5±1.1	0.6±1.6	4.1±0.3
Hymexazol	100.0±0.0	50.4±1.9	25.8±2.0	1.5±1.2	37.5±0.4	41.4±0.7	43.0±1.3	51.6±0.3	36.4±2.0

5-硝基亚氨基[1,4-2H]-1,2,4-三唑啉烯式吡虫啉类似物的合成及生物活性研究

Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics

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Compd.	Log P	Comd.	Log P	Compd.	Log P
Ⅰ-1	2.56	Ⅰ-9	5.64	Ⅰ-13	5.06
Ⅰ-3	3.81	Ⅰ-10	6.55	Ⅰ-14	4.78
Ⅰ-6	4.72	Ⅰ-12	5.26	Ⅰ-15	6.52

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