Photochemistry of bioactive compounds. Major photolytic product of endrin

Abstract

4,10,10-hexachloro-6,7-epoxy-1,4,4a,-tacyclo[6.2.1.1 3,6.0237.04s 10]dodecan-5-one, in yields 5,6,7,8,8a-octahydro-1,4-endo,endo-5,8-dimethano-up to 8 0 z . This photoproduct (XI) was found to naphthalene) was found to be cleanly converted by be highly resistant to the usual oxidation and reducirradiation at 253.7 nm, 300 nm, and in sunlight in tion procedures. Compound XI has been detected cyclohexane and hexane solution to a half-cage in fields where Endrin has been applied. ketone compound, 1,8-exo-9,11,11 -pentachloropenhe fate and persistence of organic pesticides have been given considerable attention recently. The T widespread application of pesticides has preceded their in-depth studies of the potential long-range health hazards to man and effects on his environment. The chemical fate, especially under field conditions, of many of these pesticides is still unknown. The need and importance of such photochemical research are dramatic when one considers the unexplored risks of the present applications of organic pesticides to our environment.

Metabolic transformation of DDT, dieldrin, aldrin, and endrin by marine microorganisms

“…Dieldrin and trans-aldrindiol are the metabolic products of aldrin and ketoendrin from endrin. It must be mentioned here that both photodieldrin and ketoendrin are known to form as a result of either photochemical reactions (Rosen et al, 1966;Robinson et al, 1966;Zabik et al, 1971), or by microbial actions (Matsumura et al, 1970. Although no photolytic reaction could be observed in any of the control tubes which were illuminated in the absence of microorganisms, there is a Endrin Ketoendrin (24.4%) °Same samples as the ones tested for dot.…”

Reactions and Processes

“…Non-aqueous solutions act as hydrogen donors, as in the case of hexane, or methoxy donors in the case of methanol solutions; and dechlorination, decomposition, polymerization, mineralization, dealkylation, isomerization, oxidation and reduction have been observed in a variety of solvents (Benson et al [28]; Chen and Casida [59]; Fischler and Korte [104]; Kerner et al [156]; Lombardo et al [182]; McBee and Burton [194]; McGuire et al [196,197]; Miller and Narang [215]; Mosier et al [224]; Nagl and Korte [234]; Pariar and Korte [247,248]; Plimmer et al [262]; Plimmer and Klingebiel [260,261]; Rosen and Siewierski [270]; Vollner et al [312,313]; Zabik et al [336,337]). The examples cited are basically aquatic solutions and are used to demonstrate some of the possibilities.…”

Interactions between insecticides and soil microbes

“…' and PATHAK 1972, Tu et al 1968, ZABIK et al 1971 fb = photo-and chemical decomposition (ARMSTRONG and KONRAD 1974, CROSBY 1969 fe = amount of insecticide removed through absorption by crops and subsequent removal of these crops (HARRIS and SA:' >. ' S 1967, LICHTEN-STEIN 1970 td = amount lost by volatilization and "co-distillation"; this may be accelerated by climatic conditions (moisture, temperature) and by cultural practices (tillage, etc.)…”