Benzoylphenyl Ureas—A New Group of Larvicides Interfering with Chitin Deposition

Verloop, A.; Ferrell, C. D.

doi:10.1021/bk-1977-0037.ch013

Cited by 115 publications

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“…The first possibility is that diflubenzuron directly inhibits chitin synthase, having a similar mode of action as polyoxin-D. This proposed action of diflubenzuron has been suggested by a number of workers (see Verloop and Ferrell 1977). Consistent with this explanation is the finding that the combined effect of the two inhibitors is little different from the effect of either acting alone.…”

Section: Discussionmentioning

confidence: 83%

“…These compounds are structural analogues of UDP-N-acetylglucosamine and have been shown to competitively inhibit fungal chitin synthases (Gooday 1977). The benzoylphenylurea insecticides also inhibit cuticular chitin deposition in a variety of insects (Sowa and Marks 1975;Hajjar and Casida 1978) and appear to act on the final polymerization step of the chitin biosynthetic pathway (Verloop and Ferrell 1977), but it is still unclear whether they directly inhibit chitin synthase. Thus diflubenzuron (one of the benzoylphenylurea insecticides) failed to inhibit chitin synthesis in either of the insect-derived cell-free chitin synthase systems described above (Cohen and Casida 1980b;Mayer et at.…”

Section: Introductionmentioning

confidence: 99%

“…Since the larvicidal action of diflubenzuron (and the other benzoylphenylureas) results from its inhibitory effects on chitin deposition in the integument (Verloop and Ferrell 1977;, the development of an in vitro assay system for an integumental chitin synthase could be an important advance in the investigation of the mode of action of these compounds. In this paper we describe the characteristics of an integumental chitin synthase activity in crude homogenates prepared from early third-instar larvae of the Australian sheep blowfly Lucilia cuprina.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Discussionmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…Polyoxin-D, which was established by Hori et al (1974) to be a competitive inhibitor of the fungal chitin synthase enzyme and is an analogue of UDPAG, virtually abolished incorporation when present at 0·13 mM. Similarly, diflubenzuron, which has potent larvicidal activity against L. cuprina and which inhibits chitin deposition in other insects (Verloop and Ferrell 1977), inhibited incorporation by more than 80% when present at only 10/lM. However, isoprothiolane, which is an inhibitor of fungal chitin synthesis via effects on sugar uptake (Misato et al 1979), when present at 62/lg/1 (a concentration effective in fungi), had little inhibitory effect.…”

Section: Inhibitor Studiesmentioning

confidence: 99%

“…It would seem that this final step is a complex one, perhaps involving a glycolipid intermediate (Quesada Allue et al 1976) to allow substrate access to the membrane-bound enzyme (Marks and Sowa 1976). The great potential of chitin synthesis inhibitors as specific fungicides (Misato et al 1979) and insecticides (Verloop and Ferrell 1977) has indicated the need for a better understanding of chitin biosynthesis.…”

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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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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The synthesis and larvicidal activity ofN-aroyl-N′-(5-aryl-2-furoyl)ureas

et al. 1998

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A novel type of diarolyurea compound containing a furan ring has been designed and prepared. Thus, a series of N-aroyl-N@-(5-aryl-2-furoyl)ureas were synthesized by a nucleophilic addition reaction between 5-substituted furamide and aroyl isocyanate in high yield ([80%). Their structures were con-Ðrmed by IR, [1H]NMR and elemental analyses. Bioassay showed that some of them exhibited activity against second-instar larvae of the yellow fever mosquito (Aedes aegypti L.). With the aid of artiÐcial neural network combined with multivariable regression, a preliminary study was made of structureÈactivity relationship. 1998 SCI. ( Pestic. Sci., 52, 282È286 (1998

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Benzoylphenyl Ureas—A New Group of Larvicides Interfering with Chitin Deposition

Cited by 115 publications

References 0 publications

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

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

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

The synthesis and larvicidal activity ofN-aroyl-N′-(5-aryl-2-furoyl)ureas

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