Insecticidal Benzoylphenyl Ureas: Structure-Activity Relationships as Chitin Synthesis Inhibitors

Hajjar, Nicolas P.; Casida, John E.

doi:10.1126/science.200.4349.1499

Cited by 117 publications

(49 citation statements)

References 19 publications

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“…The apparent Iso for diflubenzuron (7 x 1O-7 M) is similar to the value of 5·5 x 1O-7 M obtained by Hajjar and Casida (1978) using abdomens of the milkweed bug (Oncopeltus fasciatus) but is somewhat higher than the level of 6·9 x 1O-8 M calculated by Sowa and Marks (1975) to be the effective concentration of diflubenzuron within the cells of regenerating cockroach leg. Polyoxin-D (apparent Iso, 6 x 1O-7 M) was considerably more potent in our system than in that used by Hajjar and Casida (1978) (Iso,1·2 x IO-S M) but an Iso value of '7·5 X 10-7 M, similar to ours, was obtained by Sowa and Marks (1975).…”

Section: Discussionsupporting

confidence: 77%

“…Vardanis (1976,1979) has examined aspects of chitin biosynthesis using cultured adult integument tissue from the grasshopper (Melanoplus sanguinipes). Hajjar and Casida (1978), using cultured abdomens from adult milkweed bugs (Oncopeltus !asciatus), have measured the relative potencies of a range of benzoylphenylurea insecticides on the rate of N-[1-14C]acetylglucosamine incorporation into chitin. In both these systems chitin biosynthesis occurs without pretreatment of the tissues with exogenous p-ecdysone.…”

Section: Introductionmentioning

confidence: 99%

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Effects of Several Larvicidal Compounds on Chitin Biosynthesis by Isolated Larval Integuments of the Sheep Blowfly Lucilia cuprina

Turnbull¹,

Howells²

1982

Aust. Jnl. Of Bio. Sci.

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Isolated whole integuments from L. cuprina larvae rapidly incorporate radioactivity from both N-acetyl[I-'4C]glucosamine and [1-'4C]glucosamine into alkali-insoluble material, a reaction which does not require preincubation of the tissue with /i-ecdysone. The labelled product was degraded to N-acetylglucosamine during digestion with chitinase, establishing that it consists mainly of chitin. Incorporation was inhibited by polyoxin-D (Iso, 6 x 10-7 M) and diflubenzuron (Iso, 7 x 10-7M) but was not inhibited to any marked extent by isoprothiolane, Vetrazin or a-methyl-DOPA. The effectiveness of diflubenzuron as an inhibitor of chitin synthesis in this system (Iso, 7 x 10-7 M) correlates well with its potency as a larvicide (LDso, 2·1 x 10-6 M), providing additional support for the proposal that this compound kills larvae by interfering with chitin deposition in the cuticle. Polyoxin-D was much more effective as an inhibitor of chitin synthesis (Iso, 6 x 10-7 M) than as a larvicide (LDso, 2·0x 10-5 M). It was established that the final intermediate of chitin biosynthesis (UDP-N-acetylglucosamine) was formed in the isolated integuments in the presence of diflubenzuron and polyoxin-D. It seems likely therefore that both compounds interfere with the final polymerization step of the chitin biosynthesis pathway.

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Section: Discussionsupporting

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Effects of Several Larvicidal Compounds on Chitin Biosynthesis by Isolated Larval Integuments of the Sheep Blowfly Lucilia cuprina

Turnbull¹,

Howells²

1982

Aust. Jnl. Of Bio. Sci.

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“…The mode of inhibition of chitin synthesis by the benzoylphenylureas is still under study. Most workersll, 21,25) feel that these compounds act like Polyoxin D26) and inhibit chitin synthetase. In both Oncopeltus21) and Muscall) body walls in vitro the decrease in glucosamine incorporation into chitin in the presence of diflubenzuron is balanced by an accumulation of labelled UDP-N-acetylglucosamine.…”

Section: Discussionmentioning

confidence: 99%

Inhibition of Chitin Synthesis by Diflubenzuron in <i>Manduca</i> Larvae

et al. 1980

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“…As Hajjar and Casida discussed, the chitin synthesis inhibitors are considered to inhibit the terminal polymerization step in chitin formation. 5,21) The present bioassay method has a number of advantages.…”

Section: Discussionmentioning

confidence: 99%

Effect of Chitin Synthesis Inhibitors on Cuticle Formation of the Cultured Integument of <i>Chilo suppressalis</i>

1979

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Integumentary cuticle formation under culture conditions was examined using tissue fragments prepared from the diapausing larvae of the rice stem borer, Chilo suppressalis Walker. Exposure of the tissue to Grace's medium containing 1 hg/ml l-ecdysone for 24 hr was the optimum hormonal treatment for new cuticle formation. The new cuticle was 5.4+1.2um three days after the onset of cultivation. The median effective concentration of /l-ecdysone in Grace's medium was 0. 13+ 0.02ug/ml for new cuticle formation. The thickness of the cuticle formed in the medium containing the chitin synthesis inhibitors polyoxin D and PH 60-38 decreased as the concentration of the inhibitors increased. The median effective concentration for inhibition of cuticle formation was 9. 77 X 106 M for polyoxin D and 5. 62 x 107 M for PH 60-38. The response of the cultured integument to polyoxin D and PH 60-38 was rapid and irreversible. The cultured integument of C. suppressalis has various advantages as a bioassay system; simplicity of manipulation, reproducibility, and quantification of the biological response.

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Insecticidal Benzoylphenyl Ureas: Structure-Activity Relationships as Chitin Synthesis Inhibitors

Cited by 117 publications

References 19 publications

Effects of Several Larvicidal Compounds on Chitin Biosynthesis by Isolated Larval Integuments of the Sheep Blowfly Lucilia cuprina

Effects of Several Larvicidal Compounds on Chitin Biosynthesis by Isolated Larval Integuments of the Sheep Blowfly Lucilia cuprina

Inhibition of Chitin Synthesis by Diflubenzuron in <i>Manduca</i> Larvae

Effect of Chitin Synthesis Inhibitors on Cuticle Formation of the Cultured Integument of <i>Chilo suppressalis</i>

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