1-(2,6-disubstituted benzoyl)-3-phenylurea insecticides: Inhibitors of chitin synthesis

Post, L. C.; Jong, B.J. de; Vincent, William R.

doi:10.1016/0048-3575(74)90072-8

Cited by 186 publications

(65 citation statements)

References 5 publications

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“…The data presented in this paper support the evidence gained in previous in vivo studies by Post et al (1974) and Deul et al (1978) that benzoylphenylurea insecticides act by inhibiting some aspect of the final polymerization step of the chitin biosynthetic pathway (see Fig. 1).…”

Section: Discussionsupporting

confidence: 81%

“…There are three distinct peaks of radioactivity which co-chromatograph with the markers UDPAG (peak 1), NAG-I-P and/or NAG-6-P (peak 2), and NAG (the large peak of residual substrate). In some experiments a shoulder on peak 2 was seen, indicating partial separation of NAG-I-P and NAG-6-P. Chromatography in a second solvent system consisting of pyridine-propan-l-01-acetic acid-water (8: 8 : 3 : 4 v /v) described by Post et al (1974), also gave peaks of radioactivity coincident with UDPAG, NAG-6-P, NAG-I-P and NAG. In addition there was a peak of medium size which co-chromatographed with Gm, suggesting that some deacetylation of NAG occurs in the epidermal cells.…”

Section: Effects Of Inhibitors On Levels Of Chitin Intermediatesmentioning

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: 81%

Section: Effects Of Inhibitors On Levels Of Chitin Intermediatesmentioning

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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“…Although it is well established that acyl ureas such as diflubenzuron and teflubenzuron affect chitin synthesis (Post et al, 1974;van Eck, 1979), their mode of action is still puzzling. However, several lines of experiment argue against a direct interaction of these inhibitors with the chitin synthase.…”

Section: Inhibition Of Chitin Metabolismmentioning

confidence: 99%

Chitin metabolism in insects: structure, function and regulation of chitin synthases and chitinases

Merzendorfer

Zimoch

2003

Journal of Experimental Biology

1,048

845

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SUMMARY Chitin is one of the most important biopolymers in nature. It is mainly produced by fungi, arthropods and nematodes. In insects, it functions as scaffold material, supporting the cuticles of the epidermis and trachea as well as the peritrophic matrices lining the gut epithelium. Insect growth and morphogenesis are strictly dependent on the capability to remodel chitin-containing structures. For this purpose, insects repeatedly produce chitin synthases and chitinolytic enzymes in different tissues. Coordination of chitin synthesis and its degradation requires strict control of the participating enzymes during development. In this review, we will summarize recent advances in understanding chitin synthesis and its degradation in insects.

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“…These were run in the descending mode for 16 h (or ascending for 4 h) at room temperature in solvent system 1 (Wood 1968) consisting of butan-l-01-propan-l-01-acetone-80% (v/v) formic acid-30% (v/v) trichloroacetic acid (8:4: 5: 5: 3 v/v). Some chromatograms were also run in the ascending mode for 3·5 h at room temperature using solvent system 2 (Post et al 1974) consisting of ethyl acetate-methanol-acetic acid-water (65: 20: 7·5: 10 v/v). Chromatograms were first cut into 3-cm strips and then each strip was cut into l-cm pieces.…”

Section: Paper Chromatographymentioning

confidence: 99%

Integumental Chitin Synthase Activity in Cell-free Extracts of Larvae of the Australian Sheep Blowfly, Lucilia cuprina, and Two Other Species of Diptera

Turnbull¹,

Howells²

1983

Aust. Jnl. Of Bio. Sci.

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Chitin synthase activity has been demonstrated in crude homogenates of larval integuments from L. cuprina and in similar preparations from Musca domestica and Calliphora erythrocephala. This is the first report of an insect integumental chitin synthase. This activity brings about the incorporation of radioactivity from UDP-N-acetyl-[14C]glucosamine into an ethanol-and alkali-insoluble form. A major part of this labelled product has been characterized as chitin by its insolubility in alkali, resistance to degradation by proteases and its susceptibility to digestion by chitinase and RCI. Most of the radioactivity solubilized during digestion by chitinase co-migrates with N-acetylglucosamine, glucosamine and chitobiose during paper chromatography. Some radioactivity also becomes incorporated into non-chitin products in this system. There is substantial evidence that incorporation is not brought about by whole epidermal cells or by microbial contamination in the homogenates. The extent of incorporation obtained with the homogenates is limited by the presence of degradative enzymes which rapidly break down the substrate (UDP-N-acetylglucosamine). The incorporation was partially inhibited (50-70%) by both polyoxin-D (apparent Ki 0'04I1M) and diftubenzuron (apparent . This is the first report of a cell-free chitin-synthesizing system derived from insect tissue which is sensitive to inhibition by diftubenzuron.

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1-(2,6-disubstituted benzoyl)-3-phenylurea insecticides: Inhibitors of chitin synthesis

Cited by 186 publications

References 5 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

Chitin metabolism in insects: structure, function and regulation of chitin synthases and chitinases

Integumental Chitin Synthase Activity in Cell-free Extracts of Larvae of the Australian Sheep Blowfly, Lucilia cuprina, and Two Other Species of Diptera

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