Insecticides Diflubenzuron Research Articles

Properties and inhibition of insect integumental chitin synthetase

Chitin polymerization is catalyzed by cell-free enzyme complexes from the integument of Trichoplusia ni larvae and wing tissue of developing Hyalophora cecropia pupae obtained on extraction of homogenates for 16 hr at 5°C in 25 m M Tris-HCl buffer, pH 7.2, containing 10 m M MgCl 2, 1 m M dithiothreitol, 10 mg/ml bovine serum albumin, and 4 mg/ml digitonin. In contrast, integumental preparations from Boarmia selenaria, Earias insulana, Heliothis virescens, Oncopeltus fasciatus, Spodoptera exigua, and Tribolium castaneum exhibit little or no chitin synthetase (CS) activity. H. cecropia CS requires magnesium ions but not N-acetyl- d-glucosamine for normal activity and is almost insensitive to nikkomycin and polyoxin D. CS activity is not detected in diapausing H. cecropia pupae but synthesis of this enzyme is induced or its activity is stimulated by the molting hormone, ecdysterone, indicating possible hormonal control. T. ni CS requires magnesium ions and N-acetyl- d-glucosamine for optimal activity and is sensitive to inhibition by uridine di- and triphosphates, polyoxins B and D, and particularly nikkomycin. T. ni integumental CS activity decreases in starved larvae or those about to pupate. Both T. ni and H. cecropia CS enzymes as prepared and assayed are sensitive to captan but not to the potent insecticides diflubenzuron and BAY SIR 8514, two effective benzoylphenyl urea in vivo chitin synthesis inhibitors.

A field study on the possible impact of the insecticide diflubenzuron on insectivorous birds

This study examined the possibility that great tits ( Parus major), blue tits ( Parus caeruleus), and tree sparrows ( Passer montanus) might be poisoned by the application of diflubenzuron (Dimilin) used to control insects in woodland and roadside trees. Breeding results were compared in nestboxes in sprayed and unsprayed orchards, and in ash coppices. Diflubenzuron was found to have no significant effect on the breeding results or on the growth of nestlings. The composition of the nestlings' food and the quantity of diflubenzuron found in leaf-feeding insects in the food was measured. On this basis the maximum possible daily intake of diflubenzuron by the nestlings was estimated. These amounts were compared with the daily toxic intake by captive birds, on which dietary feeding tests were carried out.

Inhibition of Tribolium gut chitin synthetase

The chitin synthetase (CS) of Tribolium castaneum gut is inhibited 50% by 0.02 μ M nikkomycin and 4 μ M polyoxin D, two pyrimidine nucleoside fungicides, in in vitro assays with 10-min preincubation of enzyme and inhibitor prior to substrate addition. Tribolium CS is also sensitive to inhibition by the pyrimidine nucleotides uridine and cytidine di- and triphosphates. Captan, a known inhibitor of insect chitin synthesis, and the related fungicides captafol and dichlofluanid are highly potent inhibitors of Tribolium CS. Moderately active CS inhibitors are the acaricide oxythioquinox and the herbicide barban. One phenylcarbamate insect growth reatardant, H-24108, is weakly active in inhibiting Tribolium gut CS, as are three of its analogs but not 26 others. Many triazines are not inhibitory including several herbicides and an azido derivative, CGA 19255, which is active in blocking insect growth and chitin synthesis. Although the benzoylphenyl urea insecticides diflubenzuron and SIR 8514 are potent in vivo inhibitors of the polymerization step in insect chitin synthesis, they do not affect T. castaneum gut CS activity in vitro and greatly stimulate Tribolium brevicornis gut CS activity in vivo. These studies and preliminary findings on an integumental enzyme indicate that CS of these tissues is not sensitive to the direct action of benzoylphenyl ureas. This leads to speculation that the benzoylphenyl ureas act either as CS inhibitors via active metabolites formed in the integument or as blocking agents by direct binding to non-CS sites important in chitin polymerization and fibrillogenesis.

Diflubenzuron: intestinal absorption and metabolism in the rat.

1. The metabolic fate of the insecticide diflubenzuron was investigated in the rat with radioactively labelled forms of the compound. 2. Intestinal absorption, measured as the sum of urinary and biliary excretion, diminished greatly with increasing dose, from about 50% at 4 mg/kg to about 4% at 900 mg/kg. 3. Excretion was almost complete at 72 h after dosing. At that time up to 4% of a dose was recovered from the carcasses of the rats. No detectable excretion of radioactive CO2 occurred (less than 0.5% of dose). 4. The metabolic pattern in urine and bile was investigated with diflubenzuron labelled with both 3H and 14C. No unchanged compound was detected. About 80% of the metabolites appeared to have the basic diflubenzuron structure intact. Three of these, hydroxylated at either aromatic ring, were identified; they were largely excreted as conjugates in the bile. The remainder, also largely excreted in the bile, constituted very polar material. About 20% of the diflubenzuron underwent scission of the ureido bridge. One scission product, 2,6-difluorobenzoic acid, was largely excreted as such in the urine. Its counterpart, 4-chlorophenylurea, was not present in urine or bile in appreciable quantity; nor was 4-chloroaniline detected.

The effect of diflubenzuron [1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea] on soybean [ Glycine max (L.) Merr.] photosynthesis, respiration, and leaf ultrastructure

The effect of the insecticide diflubenzuron [1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea] on photosynthesis, respiration, and leaf ultrastructure of soybean [ Glycine max (L.) Merr., cv. Swift] was examined on plants treated at the second trifoliate leaf stage with 0, 0.067, and 0.269 kg of active ingredien/ha of diflubenzuron. Photosynthesis and respiration were measured with an infrared CO 2 analyzer in an open flow system prior to diflubenzuron application and at 4, 24, 48, and 96 hr after treatment with diflubenzuron. Diflubenzuron had no effect on soybean photosynthesis at any rate examined. Respiration was stimulated by the high rate (0.269 kg/ha) in a transitory manner. Tissue samples removed from both old and new leaves, 9 days after diflubenzuron application, were used for the ultrastructure study with the transmission electron microscope. The lower trifoliate leaves contained more starch grains than the upper ones being formed after treatment, but no aberrations or degradation of leaf ultrastructure due to diflubenzuron treatment were evident.

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

The 1-benzoyl-3-phenylurea insecticide diflubenzuron is a potent inhibitor for the conversion of (14)C-labeled glucose to (14)C-labeled chitin in isolated abdomens of newly emerged adult milkweed bugs (Oncopeltus fasciatus Dallas). The inhibitory activity of 24 diflubenzuron analogs in this in vitro chitin-synthesizing system is in good agreement with their toxicity to fifth instar nymphs of this species. These insecticides act quickly and directly within the integument to ultimately block the terminal polymerization step in chitin formation.