Insecticidal 1,3-dithianes

1,3-Dithianes with selected 2- and 5-substituents, e.g., 5-tert-butyl-2-(substituted-aryl)-1,3-dithianes, are a new group of insecticides; the most active with a 4-bromo, 4-chloro, 3,4-dichloro, or 4-ethynyl substituent(s) on the aryl ring and a tert-butyl group in the 5-position have housefly topic...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1992-01, Vol.40 (1), p.147-151
Main Authors: Elliott, Michael, Pulman, David A, Larkin, John P, Casida, John E
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical control
COMPOSE HETEROCYCLIQUE
COMPOSE ORGANOSOUFRE
COMPUESTO ORGANICO DEL AZUFRE
COMPUESTOS HETEROCICLICOS
Control
Diptera
Fundamental and applied biological sciences. Psychology
INSECTICIDAS
INSECTICIDE
Invertebrates
Musca domestica
Muscidae
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrates
TOXICIDAD
TOXICITE
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Summary:1,3-Dithianes with selected 2- and 5-substituents, e.g., 5-tert-butyl-2-(substituted-aryl)-1,3-dithianes, are a new group of insecticides; the most active with a 4-bromo, 4-chloro, 3,4-dichloro, or 4-ethynyl substituent(s) on the aryl ring and a tert-butyl group in the 5-position have housefly topical LD50S ranging from 0.1 to 4 microgram/without or with piperonyl butoxide (PB). Insertion of a methyl group at C-2, C-4, or C-5 has relatively little influence on activity. The 2-aryl axial and 2-aryl equatorial isomers have similar potency in some series but differ in others. Housefly Ld50S for a spirodithiane, 3-tert-butyl-9-methyl-9-(trichloromethyl)-1,5-dithiaspiro[5.5] undeca-7,10-diene, are 0.5 and 0.2 microgram/g alone and with PB, respectively. The dithiane ring in effective 2,5-disubstituted- or 2,2,5-trisubstituted-1,3-dithianes may replace the bicyclic cage of the insecticidal 1,4-disubstituted-2,6,7-trioxabicyclo[2.2.2]octanes; both classes of heterocyclic compounds act at the same or closely coupled sites in the GABA-gated chloride channel
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00013a029