Synthesis, X-ray Structure and Bioactivity of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N `-3,5dichloro-4-(1,1,2,2-tetrafluoroethoxyl)phenyl Urea / Guo Dan-Dan ,Wang Dun ,Fan Zhi-Jin ,Li Juan-Juan ,Song Hai-Bin ,Fan Qian ,Kalinina Tatiana A.,Yur'evich Morzherin Yury,Pavlovna Belskaya N.,Alekseevich Bakulev V. // CHINESE JOURNAL OF STRUCTURAL CHEMISTRY. - 2012. - V. 31, l. 12. - P. 1721-1728.

ISSN/EISSN:

0254-5861 / нет данных

Type:

Article

Abstract:

The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-3,5-dichloro-4-(1,1,2,2-tetra fluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, M-r = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance (H-1 NMR), Infra Red Spectroscopy (IR), high-resolution mass spectroscopy (HRMS), and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group P-1(-) with a = 6.0780(8), b = 11.3760(14), c = 12.1440(18) angstrom, alpha = 96.887(7), beta = 91.027(12), gamma = -104.252(13)degrees, Z = 2, V = 806.98(19) angstrom(3), D-c = 1.840 g/cm(3), mu = 0.601 mm(-1), F(000) = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.570 degrees. Two intermolecular hydrogen bonds N(2) H center dot center dot center dot O(1), S(1)center dot center dot center dot H-C(11), and three weak intermolecular interactions, C(11)center dot center dot center dot O(1), N(1)center dot center dot center dot 0(2) and S center dot center dot center dot 0(1), are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL.

Author keywords:

crystal structure; 1,2,3-thiadiazole; synthesis; biological activity SYSTEMIC ACQUIRED-RESISTANCE; CRYSTAL-STRUCTURE; HALOGEN BOND

DOI:

нет данных

Web of Science ID:

ISI:000313530200005

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	CHINESE JOURNAL STRUCTURAL CHEMISTRY
Address	FUIJAN INST RES STRUCT MATTER, CHINESE ACAD SCIENCES, FUZHOU, FUJIAN 350002, PEOPLES R CHINA
Language	English
Keywords-Plus	SYSTEMIC ACQUIRED-RESISTANCE; CRYSTAL-STRUCTURE; HALOGEN BOND
Research-Areas	Chemistry; Crystallography
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Crystallography
Author-Email	fanzj@nankai.edu.cn
ResearcherID-Numbers	Morzherin, Yury/M-7420-2013
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676
Funding-Acknowledgement	National Natural Science Foundation of China {[}20872071]; Natural Science Foundation of Tianjin {[}10JCZDJC17500]; National Key Project for Basic Research {[}2010CB126105]; National Key Technology Research and Development Program {[}2011BAE06B02]; Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology {[}201002250]; Tianjin Key Technology Research and Development Program {[}11ZCGYNC00100]
Funding-Text	This study was funded in part by grants from the National Natural Science Foundation of China (20872071), the Natural Science Foundation of Tianjin (10JCZDJC17500), the National Key Project for Basic Research (2010CB126105), the National Key Technology Research and Development Program (2011BAE06B02) and the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology (201002250), Tianjin Key Technology Research and Development Program (11ZCGYNC00100)
Number-of-Cited-References	18
Usage-Count-Since-2013	14
Journal-ISO	Chin. J. Struct. Chem.
Doc-Delivery-Number	070SC