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IRAC 15 benzoylurea

Common name diflubenzuron (BSI, E-ISO, (m) F-ISO, ANSI, ESA) IUPAC name 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea
Chemical Abstracts name N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide Other names DFB; difluron CAS RN [35367–38–5] EC no. 252–529–3 Development codes DU 112307; PH 60–40; PDD 60–40-I (all Duphar); TH 6040 (T. H. Agriculture & Nutrition Co.) Official codes OMS 1804; ENT 29 054 Smiles code Fc1cccc(F)c1C(=O)NC(=O)Nc2ccc(Cl)cc2
Composition Tech. grade diflubenzuron is ≥95% pure. Mol. wt. 310.7 M.f. C14H9ClF2N2O2 Form Colourless crystals; (tech., off-white to yellow crystals). M.p. 223.5–224.5 °C B.p. 257 °C/40.0 kPa (tech.) V.p. 1.2 × 10-4 mPa (25 °C) (gas saturation method) Kow logP = 3.8 (pH 4), 4.0 (pH 8), 3.4 (pH 10) Henry ≤4.7 × 10-4 Pa m3 mol-1 (calc.) S.g./density 1.57 (20 °C) Solubility In water 0.08 mg/l (pH 7, 25 °C). In n-hexane 0.063, toluene 0.29, dichloromethane 1.8, acetone 6.98, ethyl acetate 4.26, methanol 1.1 (all in g/l, 20 °C). Stability Light-sensitive when in solution, but stable to sunlight as a solid. <0.5% decomposition after 1 d storage at 100 °C; <0.5% after 7 d at 50 °C. In aqueous solution (20 °C), stable at pH 5 and 7 (DT50 >180 d); at pH 9, DT50 32.5 d.
History Insecticide reported by J. J. van Daalen et al. (Naturwissenschaften, 1972, 59, 312) and reviewed by A. C. Grosscurt (Pestic. Sci., 1978, 9, 373) and W. Maas et al. (Chem. Pflanzenschutz-Schädlingsbekämpfungsmittel, 1980, 6, 423). Introduced in 1975 by Philips-Duphar B.V. (now Chemtura Corp.). Patents GB 1324293; US 3748356; US 3989842 Manufacturers Chemtura; Agria; Dongbu Fine; E-tong; Golden Harvest; Hebei Veyong; Jiangyin Suli; JIE; Laboratorios Agrochem; Shanghai Shengnong; Sharda; Sinon; Sundat
Biochemistry Chitin synthesis inhibitor, type 0 (Lepidopteran); and so interferes with the formation of the insect cuticle. This action is quite specific; related biochemical processes, such as chitin synthesis in fungi, and biosynthesis of hyaluronic acid and other mucopolysaccharides in chickens, mice and rats, are not affected. Mode of action Non-systemic insect growth regulator with contact and stomach action. Acts at time of insect moulting, or at hatching of eggs. Uses For control of a wide range of leaf-eating insects in forestry, woody ornamentals and fruit. Controls certain major pests in cotton, soya beans, citrus, tea, vegetables, rice, peanuts, treenuts and mushrooms. Also controls larvae of flies, mosquitoes, grasshoppers, Mormon crickets and migratory locusts. Used as an ectoparasiticide on sheep for control of lice, fleas and blowfly larvae. Due to its selectivity and rapid degradation in soil and water, diflubenzuron has no or only a slight effect on the natural enemies of various harmful insect species. These properties make it suitable for inclusion in integrated control programmes. Diflubenzuron is effective at 25–75 g/ha against most leaf-feeding insects in forestry; in concentrations of 0.01–0.015% a.i. against codling moth, leaf miners and other leaf-eating insects in top fruit; in concentrations of 0.0075–0.0125% a.i. against citrus rust mite in citrus; and at a dosage of 50–150 g/ha against a number of pests in cotton (cotton boll weevils, armyworms, leafworms), soya beans (soya bean looper complex) and maize (armyworms). Also for control of larvae of mushroom flies in mushroom casing (1 g/m2); mosquito larvae (25–100 g/ha); fly larvae in animal housing (0.5–1 g/m2 surface); and locusts and grasshoppers (60–67.5 g/ha). Formulation types DT; GR; OF; SC; UL; WG; WP. Compatibility Incompatible with strongly alkaline products.
Selected products ‘Bi-Larv’ (Chemtura) ; ‘Device’ (Chemtura) ; ‘Diflorate’ (Mobedco) ; ‘Dimilin’ (Chemtura) ; ‘Dimisun’ (Sundat) ; ‘Du-Dim’ (Chemtura, Siapa) ; ‘Forester’ (Agria) ; ‘Patron’ (Vapco) Other products ‘Adept’ (Chemtura) ; ‘Difuse’ (Protex, Sintagro) ; ‘Dimax’ (Nufarm Industria Quimica) ; ‘Full’ (Chemia) ; ‘Indipendent’ (Certis Europe) ; ‘Kitinaz’ (Doğal) ; ‘Kitinex’ (Cequisa) ; ‘Micromite’ (Chemtura) ; ‘Vigilante’ (Chemtura) Discontinued products ‘Astonex *’ (Shell) ; ‘Hilmilin *’ (Hindustan)
Product analysis by rplc with uv detection (CIPAC Handbook, 1998, H, 141; AOAC Methods, 18th Ed., 983.07; A. van Rossum et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 165). Residues determined by hplc-ms/ms. In soil or water by hplc/ms-ms.
Fate in soil, plants and animals has been reviewed (A. Verloop & C. D. Ferrell, ACS Symp. Series, 1977, No. 37, 237). Animals In rats, diflubenzuron is extensively metabolised by dechlorination, glucuronidation, sulphation and hydrolysis. Diflubenzuron is poorly absorbed from the gastro-intestinal tract and is found in the faeces. Absorbed radioactivity is removed almost completely in 24–48 hours. Diflubenzuron and/or its metabolites do not accumulate in any other parts of the rat body. Plants Non-systemic. Not metabolised on plants. Soil/Environment Diflubenzuron is strongly absorbed by the soil/humic acid complex and is immobile to slightly mobile in soil. (Kfoc1983–6918 ml/g). Rapidly degraded in soil under aerobic conditions, DT50 (20 °C, pF2) 2–6.7 days. The principal degradation products are 4-chlorophenylurea (CPU) and 2,6-difluorobenzoic acid (DFBA). Diflubenzuron hydrolyses to CPU and DFBA (pH 9, 25 °C) DT50 32.5 d. Diflubenzuron is fairly persistent in the water/sediment system under aerobic conditions, DT50 (whole system) 3.7–5.4 d (20 °C) with the formation of two major metabolites, CPU and DFBA. Diflubenzuron is classified as not readily biodegradable.
EHC 184 (1996). JMPR Mtg. 95 (2002); JMPR Evaln. I 54 (1988), 96 (2002); JMPR Evaln. II 94 (2001). WHO/FAO specifications, March 2006. CAG. HSG 99 (1995). PDS 77 (1996); EU Rev. Rep. SANCO/831/08 (2010), EFSA Sci. Rep. (2009) 332, 1-111. EU Status (1107/2009) Approved, 2008/69/EC.
Oral Acute oral LD50 for rats and mice >4640 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000, rats >10 000 mg/kg. Not classified as a skin or eye irritant. Not a skin sensitiser. Inhalation LC50 for rats >2.88 mg/l. NOEL (1 y) for rats, mice and dogs 2 mg/kg b.w. daily, for methaemoglobin formation. No teratogenic, mutagenic, or oncogenic effect was observed. ADI (JMPR) 0.02 mg/kg b.w. [2001]; (JECFA evaluation) 0.02 mg/kg b.w. [1994]; (EC) 0.012 mg/kg b.w. [2008]; (EPA) cRfD 0.02 mg/kg b.w. [1990, 1997]. Water GV 0.25 mg/l (company value); no GV set by WHO. Toxicity class WHO (a.i.) U EPA (formulation) III EC classification N; R50
Birds Acute oral LD50 (14 d) for bobwhite quail and mallard ducks >5000 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >1206 mg/kg diet. Fish LC50 (96 h) for zebra fish (Brachydanio rerio) >64.8, rainbow trout >106.4 mg/l (both based on ‘Dimilin’ WG-80). Daphnia LC50 (48 h) 0.0026 mg/l (based on ‘Dimilin’ WG-80). Algae NOEC for Selenastrum capricornutum 100 mg/l (based on ‘Dimilin’ WG-80). Bees Not hazardous to bees and predatory insects; LD50 (oral and contact) >100 μg/bee. Worms NOEC for Eisenia foetida ≥780 mg/kg substrate.

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