SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 9: 1736 - 1740

DOI: https://doi.org/10.6023/cjoc1203051

Articles

Synthesis and Insecticidal Activity of Sulfinic Esters Containing Dichloropropene

  • Li Qin ,
  • Yu Haibo ,
  • Guan Aiying ,
  • Liang Songjun ,
  • Song Yuquan ,
  • Li Bin
Expand
  • State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd., Shenyang 110021

Received date: 2012-03-05

  Revised date: 2012-05-22

  Online published: 2012-04-18

Supported by

Project supported by the National Key Project of Scientific and Technology of China (No.2011BAE06B01-05) and the National Key Basic Research Program

Fold

Abstract

In search for new insecticides with high activity, broad-spectrum, low toxicity, favorable safety profile and no cross resistance to commercialized insecticides, eleven novel sulfinic esters containing dichloropropene were designed and synthesized from p-dihydroxybenzene in multiple steps. The structures of title compounds were identified by 1H NMR,13C NMR spectra and elemental analysis. The preliminary bioassays indicated that some of the target compounds showed good insecticidal activity against Plutella xylostella L. 3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)phenoxyl]propyl n-hexyl sulfurous ester (7h) showed 80% mortality against Plutella xylostella L. at 10 mg/L, better than pyridaly.

Key words： dichloropropene; sulfinic esters; synthesis; insecticidal activity; Plutella xylostella L

Cite this article

Li Qin , Yu Haibo , Guan Aiying , Liang Songjun , Song Yuquan , Li Bin . Synthesis and Insecticidal Activity of Sulfinic Esters Containing Dichloropropene[J]. Chinese Journal of Organic Chemistry, 2012 , 32(9) : 1736 -1740 . DOI: 10.6023/cjoc1203051

References

[1] Elberta, A.; Nauen, R. Pest Manage. Sci. 2000, 56, 60.   

[2] Wang, B.-Z.; Xu, X.-Y.; Tao, Y.-C. Chin. J. Pestic. Sci. 2010, 12, 429 (in Chinese). (王宝珠, 徐晓勇, 陶玉成, 农药学学报, 2010, 12, 429.)

[3] Nauen, R.; Denhol, M. I. Arch. Insect Biochem. Physiol. 2005, 58, 200.

[4] Tang, Z.-L.; Liu, H.-W.; Wang, X.-G.; Ou, X.-M.; Tang, R.-H.; Chen, Y.-B. Chin. J. Org. Chem. 2007, 27, 999 (in Chinese). (唐子龙, 刘汉文, 王晓光, 欧晓明, 唐仁和, 陈奕彬, 有机化学, 2007, 27, 999.)

[5] Satto, S.; Isayama, S.; Sakamoto, N. J. Pestic. Sci. 2004, 29, 372.

[6] Satto, S.; Ysoshioka, T.; Umeda, K. J. Pestic. Sci. 2006, 31, 335.

[7] Covey, R. A.; Smith, A. E.; Hubbard, W. L. US 3179682, 1965 [Chem. Abstr. 1965, 63, 62731].   

[8] Covey, R. A.; Smith, A. E.; Hubbard, W. L. US 3272854, 1965 [Chem. Abstr. 1965, 62, 90575].

[9] Covey, R. A.; Smith, A. E.; Hubbard, W. L. US 4003940, 1977 [Chem. Abstr. 1977, 86, 171076].   

[10] George, T.; Broon, E. L.; Suarez, D. P. WO 2004098283, 2004 [Chem. Abstr. 2004, 141, 410815].

[11] Takarazuka, H. I.; Toyonaka, K. I.; Sakamota, N. US 6140274, 1997 [Chem. Abstr. 1997, 127, 205343].   

[12] Toyonaka, H. S.; Misawa, M. S. US 6590104B, 2003 [Chem. Abstr. 2003, 139, 85249].   

[13] You, J.-F.; Xiao, X.-H. Fine Chem. Interm. 2005, 32, 37 (in Chinese). (游剑飞, 肖旭辉, 精细化工中间体, 2005, 32, 37.)

Options
Outlines

/

〈 〉