Synthesis and insecticidal activity of new pyrethroids

Pest Management Science

Volumn 65, Issue 8, 2009, Pages 900-905

  Silvério, Flaviano O ^a   de Alvarenga, Elson S ^a   Moreno, Shaiene C ^a   Picanço, Marcelo C ^a  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

Author keywords

Ascia monuste orseis; Insecticide activity; Periplaneta americana; Pyrethrins; Pyrethroids; Tuta absoluta

Indexed keywords

INSECTICIDE; PYRETHROID;

BIOACTIVITY; BUTTERFLY; HYDROLYSIS; INSECTICIDE; PEST CONTROL; PYRETHROID;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; INSECT; SYNTHESIS;

ANIMALS; INSECTICIDES; INSECTS; PYRETHRINS;

ASCIA MONUSTE; MUSCA DOMESTICA; ORSEIS; PERIPLANETA; PERIPLANETA AMERICANA; SITOPHILUS ZEAMAIS; TUTA ABSOLUTA;

EID: 69249220249     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1771     Document Type: Article

References (22)

1. Elliott M and Janes NF, Synthetic pyrethroids - a new class of insecticide. Chem Soc Rev 7:473-505 (1978).
2. Shafer TJ, Meyer DA and Crofton KM, Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs. Environ Health Persp 113:123-136 (2005).
3. Elliott M and Casida JE, Optically pure pyrethroids labeled with deuterium and tritium in methylcyclopentenyl ring. J Agr Food Chem 20:295-299 (1972).
4. Ray DE and Fry JR, A reassessment of the neurotoxicity of pyrethroid insecticides. Pharmacol Therapeut 111:174-193 (2006).
5. Shafer TJ and Meyer DA, Effects of pyrethroids on voltage-sensitive calcium channels: a critical evaluation of strengths, weaknesses, data needs, and relationship to assessment of cumulative neurotoxicity. Toxicol Appl Pharm 196:303-318 (2004).
6. Soderlund DM, Clark JM, Sheets LP, Mullin LS, Piccirillo VJ, Sargent D, et al., Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment. Toxicol 171:3-59 (2002).
7. Vatandoost H, Structure-activity relationship of pyrethroids against different geographical strains of larvae of malaria vector, Anopheles stephensi, and role of mixed function oxidase in resistance phenomenon. Acta Med Iranica 42:89-96 (2004).
8. Chyan M and Norton SJ, Synthesis and biological evaluation of new pyrethroids having halogen, keto, or nitro group-containing substituents. J Agr Food Chem 43:2286-2290 (1995).
9. Minato A, A new, versatile method for the modification of synthetic pyrethroids - regioselectiveandstereoselectivemonoarylationand heteroarylation of (2,2-dihaloethenyl)cyclopropanecarboxylates catalyzed by palladium-phosphine complexes. J Org Chem 56:4052-4056 (1991).
10. Brown DG, Cyanovinyl pyrethroids and pesticidal use thereof. US Patent 4423062 (1983).
11. Liu TX, Biology andlife history of Asciamonustemonuste (Lepidoptera: Pieridae), a potential pest of cruciferous vegetables. Ann Entomol Soc Am 98:726-731 (2005).
12. Haji FNP, Parra JRP, Silva JP and Batista JGS, Biologia da traça-do- tomateiro sob condic ̧ões de laboratório. Pesquisa Agropecuária Brasileira 23:107-110 (1988).
13. Botton M, Lorini I and Afonso APS, Sitophilus zeamais Mots. (Coleoptera: Curculionidae) damaging vineyards in Rio Grande do Sul, Brazil. Neotrop Entomol 34:355-356 (2005).
14. Trematerra P, Valente A, Athanassiou CG and Kavallieratos G, Kernel-kernel interactions and behavioral responses of Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae). Appl Entomol Zool 42:129-135 (2007).
15. West LS, The Housefly, its Natural History, Medical Importance, and Control. Comstock Publ Co., Ithaca, NY, 584 pp. (1951).
16. rd edition. Pergamon Press, Oxford, UK, 391 pp. (1988).
17. Alvarenga ES, Carneiro VMT, Silvério FO and Saliba WA, A high yield synthesisof1,2: 56-di-O-isopropylidene-D-mannitol.JChileanChem Soc 51:986-988 (2006).
18. Mann J, Partlett NK and Thomas A, A practical synthesis of (S)-5-hydroxymethylfuran-2(5H)-one from 1,2-5,6-di-O-isopropylidene-D-mannose. J Chem Res 137:369-369 (1987).
19. Krief A, Dumont W and Pasau P, From tartaric acid to the most biologically-active insecticides - straightforward enantioselective synthesis of pyrethrins. Tetrahedron Lett 29:1079-1082 (1988).
20. Krief A, Provins L and Froidbise A, Enantioselective synthesis of 1(R)- trans-chrysanthemic acid. Tetrahedron Lett 43:7881-7882 (2002).
21. Krief A, Ollevier T and Dumont W, Novel synthesis of vinylcyclopropyl ketones and vinylcyclopropanecarboxylic acids: application to the stereoselective synthesis of trans-chrysanthemic acid. J Org Chem 62:1886-1890 (1997).
22. Krief A and Lecomte P, Stereoselective syntheses of cyclopropane derivatives from gamma-alkoxy-alpha,beta-unsaturated carbonyl- compounds and isopropylidene transfer reagents. Tetrahedron Lett 34:2695-2698 (1993).