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Insecticide Teflubenzuron
NOMENCLATURE Teflubenzuron
Common name teflubenzuron (BSI, draft E-ISO, (m) draft F-ISO); no name (the Netherlands)
IUPAC name 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea
Chemical Abstracts name N-[[(3,5-dichloro-2,4-difluorophenyl)amino]carbonyl]-2,6-difluorobenzamide
CAS RN [83121-18-0] Development codes CME 134 (Celamerck)
PHYSICAL CHEMISTRY Teflubenzuron
Mol. wt. 381.1 M.f. C14H6Cl2F4N2O2 Form White to yellowish crystals. M.p. 222.5 ºC V.p. 8 ´ 10-7 mPa (20 ºC) KOW logP = 4.3 (20 ºC) Solubility In water 0.019 mg/l (23 ºC). In acetone 10, ethanol 1.4, dimethyl sulfoxide 66, dichloromethane 1.8, cyclohexanone 20, hexane 0.05, toluene 0.85 (all in g/l, 20 ºC). Stability Stable for more than 2 years at room temperature. On hydrolysis, DT50 (50 ºC) 5 d (pH 7), 4 h (pH 9).
APPLICATIONS Teflubenzuron
Biochemistry Chitin synthesis inhibitor, affecting moulting. Mode of action Non-systemic insect growth regulator with stomach action. May affect fertility of female insects after contact or ingestion. Uses Control of Lepidoptera, Coleoptera, Diptera, Aleyrodidae, Hymenoptera, Psyllidae, and Hemiptera larvae on vines, pome fruit, stone fruit, citrus fruit, cabbages, potatoes, vegetables, soya beans, trees, sorghum, tobacco, and cotton. Also controls fly and mosquito larvae, and immature stages of major locust species. Also under development to protect salmonids against sea lice. Formulation types SC; UL. Selected tradenames: 'Nemolt' (BASF); 'Nomolt' (BASF)
MAMMALIAN TOXICOLOGY Teflubenzuron
Reviews FAO/WHO 71, 73 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not irritant to skin or eyes of rabbits. Non-sensitising to skin. Inhalation LC50 (4 h) for rats >5058 mg dust/m3. NOEL (90 d) for rats 8 mg/kg b.w. daily, for dogs 4.1 mg/kg b.w. daily. ADI (JMPR) 0.01 mg/kg b.w. [1994]. Other Non-teratogenic. Non-mutagenic in Ames, mammalian cell, and micronucleus assays. Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) IV
ECOTOXICOLOGY Teflubenzuron
Birds Acute oral LD50 for quail >2250 mg/kg. Dietary LC50 for quail and ducks >5000 mg/kg. Fish LC50 (96 h) for trout and carp >500 mg/l. Bees Non-toxic to bees when used at recommended rates; LD50 (topical) >1000 mg/bee. Other beneficial spp. Low toxicity to predatory arthropods.
ENVIRONMENTAL FATE Teflubenzuron
Animals In rats, following oral administration, teflubenzuron and its metabolites are rapidly excreted in the faeces and urine. Three metabolites have been identified in the urine (D. Eichler et al., 6th Int. Congr. Pestic. Chem. IUPAC, 1986, Abstr. 7A-10). Plants Almost no uptake and no metabolism in plants. Soil/Environment DT50 in soil 2-12 w. Microbial degradation occurs in soil, with rapid metabolism to 3,5-dichloro-2,4-difluorophenylurea as the major metabolite. |