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diflubenzuron
SPECIFICATIONS
Common name diflubenzuron
IUPAC name 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea
CAS RN [35367-38-5]
Mol. wt. 310.7
M.f. C14H9ClF2N2O2
Formulation types GR; HN; OF; SC; UL; WG; WP.
Diflubenzuron Usage And Synthesis
Description

Diflubenzuron is an insecticide of the benzoylurea class.It is used in forest management and on field crops to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths.It is a widely used larvicide in India for control of mosquito larvae by public health authorities. Diflubenzuron is approved by the WHO Pesticide Evaluation Scheme.

Uses

nsystemic insecticide used to control leaf-eating larvae and leaf miners in forestry, woody ornamentals and fruit trees.

Uses

Diflubenzuron is used for the control of a wide range of leaf-eating insects in forestry, woody ornamentals and fruit. It controls major pests on cotton, soyabean, citrus and tea and it also controls larvae of flies, mosquitoes and locusts. Diflubenzuron is also used as an ectoparasiticide.

Uses

Diflubenzuron is a benzoylurea-based pesticide belonging to the benzamide class. Diflubenzuron is a chitin synthesis inhibitor. Diflubenzuron is used in both agriculture and forest management to selec tively control insect pests, particularly moths and weevils.

Uses

An inhibitor of TCDD-induced CYP1a1 expression in HepG2 cells.

Uses

Insecticide.

Definition

A benzoylurea insecticide that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 4-chlorophenyl group, and a hydrogen attached to the other nitrogen is replaced bgy a 2,6-difluorobenzoyl group.

General Description

Colorless to yellow crystals. Used as a selective insecticide.

Air & Water Reactions

Hydrolyzed in alkaline solution above pH 9.0.

Agricultural Uses

Insecticide, Larvicide: Diflubenzuron is used primarily on citrus, cattle feed, cotton, forestry, mushrooms, ornamentals, pastures, soybeans, standing water, sewage systems, and wide-area general outdoor treatment sites. The insecticide behaves as a chitin inhibitor to inhibit the growth of many leaf-eating larvae, mosquito larvae, aquatic midges, rust mite, boll weevil, and house-black-, and stable-flies. Diflubenzuron was first registered in the United States in 1979 for use as an insecticide.

Safety Profile

Moderately toxic by skin contact. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, F-, and NOx.

Environmental Fate

Soil. The half-life in soil is <1 week (Hartley and Kidd, 1987). Di?ubenzuron degrades more rapidly in neutral or basic conditions but more slowly under acidic conditions (pH <6) (Ivie et al., 1980). Chemical/Physical. Hydrolyzes in water to 4-chlorophenylurea (Verschueren, 1983).

Metabolic pathway

Diflubenzuron was the first active substance commercialised as a benzoylurea insect growth regulator and there is extensive published information on its degradation and metabolism. Detailed studies of the degradation in soils have shown that cleavage of the urea linkage is the major process. This also occurs in plants, insects and mammals but the formation of products in which diflubenzuron is hydroxylated in both rings is also an important metabolic process.

Degradation

Diflubenzuron was shown to be stable to hydrolysis in aqueous solution at acidic pH (DT50> 56 days at pH 4) but was readily hydrolysed at pH 10 (DT50 <3 days). In distilled water the DTa was 7 days (Ivie et al., 1980). The major degradation products isolated were 4-chlorophenylurea (2) and 2,6-difluorobenzoic acid (3). An additional minor product was 2,6- difluorobenzamide (4). The hydrolysis products are shown in Scheme 1. Additional products were formed under extreme conditions (121 °C under pressure). Aqueous solutions of diflubenzuron are reported to be unstable to light but the solid is stable in sunlight (PM).

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