4-Alkynylphenylsilatranes: Insecticidal activity, mammalian toxicity, and mode of action

Journal Article · Wed Aug 01 00:00:00 EDT 1990 · Journal of Agricultural and Food Chemistry; (USA)

DOI:https://doi.org/10.1021/jf00098a023· OSTI ID:5957251

Horsham, M A; Palmer, C J; Cole, L M; Casida, J E ^[1]

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1. Univ. of California, Berkeley (USA)

4-Ethynyl- and 4-(prop-1-ynyl)phenylsilatranes (N(CH{sub 2}CH{sub 2}O){sub 3}SiR, R = C{sub 6}H{sub 4}-4-C{triple bond}CH or C{sub 6}H{sub 4}-4-C{triple bond}CCH{sub 3}) are highly toxic to houseflies (pretreated with piperonyl butoxide) and milkweed bugs (topical LD{sub 50}s 3-14 {mu}g/g) and to mice (intraperitoneal LD{sub 50}s 0.4-0.9 mg/kg), and they are moderately potent inhibitors of the ({sup 35}S)-tert-butylbicyclophosphorothionate or TBPS binding site (GABA-gated chloride channel) of mouse brain membranes. Scatchard analysis indicates noncompetitive interaction of 4-ethynylphenylsilatrane with the TBPS binding site. Phenylsilatrane analogues with 4-substituents of H, CH{sub 3}, Cl, Br, and C{triple bond}CSi(CH{sub 3}){sub 3} are highly toxic to mice but have little or no activity in the insect and receptor assays. Radioligand binding studies with (4-{sup 3}H)phenylsilatrane failed to reveal a specific binding site in mouse brain. Silatranes with R = H, CH{sub 3}, CH{sub 2}Cl, CH{double bond}CH{sub 2}, OCH{sub 2}CH{sub 3}, and C{sub 6}H{sub 4}-4-CH{sub 2}CH{sub 3} are of little or no activity in the insect and mouse toxicity and TBPS binding site assays as are the trithia and monocyclic analogues of phenylsilatrane. 4-Alkynylphenylsilatranes are new probes to examine the GABA receptor-ionophore complex of insects and mammals.

• OSTI ID: 5957251
• Journal Information: Journal of Agricultural and Food Chemistry; (USA), Vol. 38:8; ISSN 0021-8561
• Country of Publication: United States
• Language: English

Related Subjects

60 APPLIED LIFE SCIENCES
INSECTICIDES
STRUCTURE-ACTIVITY RELATIONSHIPS
MICE
SULFUR 35
SULFUR COMPOUNDS
TOXICITY
TRACER TECHNIQUES
TRITIUM COMPOUNDS
ANIMALS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
DAYS LIVING RADIOISOTOPES
EVEN-ODD NUCLEI
HYDROGEN COMPOUNDS
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAMMALS
NUCLEI
PESTICIDES
RADIOISOTOPES
RODENTS
SULFUR ISOTOPES
VERTEBRATES
553003* - Agriculture & Food Technology- Pest & Disease Control- (1987-)