Synthesis, crystal structure and biological activity of aryl [(N,N′-diacyl-N′-tert-butylhydrazino)thio]methylcarbamates

Pest Management Science

Volumn 61, Issue 10, 2005, Pages 997-1002

  Shang, Jian ^a,b   Wang, Qing Min ^a   Run, Qiu Huang ^a   Chun, Hui Mao ^a   Chen, Li ^a   Fu, Chun Bi ^a   Hai, Bin Song ^a  

^a NANKAI UNIVERSITY   (China)

^b YANTAI UNIVERSITY   (China)

Author keywords

Aryl (N,N diacyl N tert butylhydrazino)thio methylcarbamates; Crystal structure; Larvicidal activity; Synthesis

Indexed keywords

CARBAMIC ACID DERIVATIVE; INSECTICIDE;

PESTICIDE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; LARVA; MOTH;

ANIMALS; CARBAMATES; INSECTICIDES; LARVA; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOTHS;

INSECTA;

EID: 25444508700     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ps.1073     Document Type: Article

References (16)

1. Wing KD, RH5849, A nonsteroidal ecdysone agonist: effects on a Drosophila cell line. Science (Washington) 241:467-469 (1988).
2. Wing KD, Slawecki RA and Carlson GR, RH5849, a nonsteroidal ecdysone agonist: effects on larval lepidoptera. Science (Washington) 241:470-472 (1988).
3. Wing KD, Anthelmintic N′-substituted-N,N′-disubstituted- hydrazines. US Patent 5 424 333 (1995).
4. Drabek J, N-sulfenyl and N-sulfinyl-N,N′-diacylhydrazides. EP Patent 395 581 (1990).
5. Dhadialla TS and Jansson RK, Non-steroidal ecdysone agonists: new tools for IPM and insect resistance management. Pestic Sci 55:357-359 (1999).
6. Carlson GR, Dhadialla TS and Hunter R, The chemical and biological properties of methoxyfenozide, a new insecticidal ecdysteroid agonist. Pest Manag Sci 57:115-119 (2001).
7. Hsu ACT, 1,2-Diacyl-1-alkylhydrazines, a new class of insect growth regulators, in Synthesis and chemistry of agrochemicals II, ed by Baker BR, Fenyes JG and Moberg W, ACS Symposium Series No 443, American Chemical Society, Washington, DC, pp 478-490 (1991).
8. Fahmy MAH, Mallipudi NM and Fukuto TR, Selective toxicity of N,N′-thiodicarbamates. J Agric Food Chem 26:550-557 (1978).
9. Fahmy MAH, Chiu YC and Fukuto TR, Selective toxicity of N-substituted biscarbamoyl sulfides. J Agric Food Chem 22:59-62 (1974).
10. Brown M and Kohn G, N-Chlorothiocarbamates. US Patent 3 843 689 (1974).
11. Drabek J, Bis-(O-1-alkylthio-ethylimino)-N-methyl-carbamic acid)-N,N′-sulphide insecticides. US Patent 4 004 031 (1977).
12. Wang QM, Huang RQ, Bi FC and Li ZG, Synthesis and biological activity of novel N-sulfenylated derivatives of diacylhydrazines. J Chem Res 342-343 (2001).
13. Wang QM, Cheng JR and Huang RQ, Synthesis and insecticidal evaluation of novel N-(S-amino)sulfenylated derivatives of diacylhydrazines. Pest Manag Sci 58:1250-1253 (2002).
14. Hsu AC, Aller HE, Murphy RA, Le DP, Hamp DW and Weinstein B, Insecticidal N′-substituted-N,N′-disubstituted-hydrazines. US Patent 5 117 057 (1993).
15. Mao CH, Wang QM, Huang RQ, Bi FC, Chen L, Liu YX and Shang J, Synthesis and insecticidal evaluation of novel N-oxalyl derivatives of tebufenozide. J Agric Food Chem 52:6737-6741 (2004).
16. Chan TH, Ali A and Britten JF, The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine, a nonsteroidal ecdysone agonist, and its effects on spruce budworm (Choristoneura fumiferana). Can J Chem 68:1178-1181 (1990).