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Buprofezin

Buprofezin 50%SC
Buprofezin 40%WDG

Insecticide, acaricide

NOMENCLATURE
Common name buprofezin (BSI, draft E-ISO); buprofezine ((f) draft F-ISO)
IUPAC name 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one
Chemical Abstracts name 2-[(1,1-dimethylethyl)imino]tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1,3,5-thiadiazin-4-one
CAS RN [69327-76-0] Development codes NNI-750 (Nihon Nohyaku); PP618 (ICI)

Buprofezin APPLICATIONS
Biochemistry Probable chitin synthesis and prostaglandin inhibitor. Hormone disturbing effect, leading to suppression of ecdysis. Mode of action Persistent insecticide and acaricide with contact and stomach action; not translocated in the plant. Inhibits moulting of nymphs and larvae, leading to death. Also suppresses oviposition by adults; treated insects lay sterile eggs. Uses Insecticide with persistent larvicidal action against Homoptera, some Coleoptera and also Acarina. Effective against Cicadellidae, Deltocephalinae (leafhoppers) and Delphacidae (planthoppers) in rice, at 50-250 g/ha; Cicadellidae (lady beetle) in potatoes; Aleyrodidae (whitefly) in citrus, cotton and vegetables, at 0.025-0.075 g/ha; Coccidae, Diaspididae (scale insects) and Pseudococcidae (mealybugs) in citrus and top fruit, at 25-50 g/hl; Tarsonemidae in vegetables, at 250-500 g/ha. Suitable for IPM programmes. Phytotoxicity Slightly phytotoxic to Chinese cabbage. Formulation types DP; GR; SC; WP. Selected tradenames: 'Applaud' (Nihon Nohyaku)

Buprofezin OTHER TRADENAMES
'Accolade' (Aventis); 'Viappla' (Vipesco) mixtures: 'Dadeci' (+ deltamethrin) (Aventis); 'Karapp' (+ lambda-cyhalothrin) (Syngenta)

ANALYSIS
Product by gc. Residues in soil and rice plants and water, by gc with ECD (M. Uchida et al., J. Pestic. Sci., 7, 397 (1982)); in crops, by gc with NPD (H. Nishizawa et al., J. AOAC International, 77, 1631 (1994)). Details from Nihon Nohyaku.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 86 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 2198, female rats 2355, male and female mice >10 000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Mild skin irritant (guinea pigs); not irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >4.57 mg/l air. NOEL for male rats 0.90, female rats 1.12 mg/kg daily. ADI (JMPR) 0.01 mg/kg [1999]. Other Non-carcinogenic, non-mutagenic. Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) III

ECOTOXICOLOGY
Fish LC50 (48 h) for carp 2.7, rainbow trout >1.4 mg/l. Daphnia LC50 (3 h) for D. pulex 50.6 mg/l. Bees No direct effect at 2000 mg/l (WP formulation). Other beneficial spp. No effect on various predators (Euseius stipulatus 250 mg/l; Phytoseiulus persimilis 500 mg/l; Cyrtorhinus lividipennis, Microvelia atrolineata 250 mg/l; Lycosa pseudoannulata 2000 mg/l) or parasites (Aphytis linganensis 125 mg/l; Cales noacki, Encarsia formosa, Paracentrobia andoi 250 mg/l; Ephedrus japonicus 1000 mg/l).

ENVIRONMENTAL FATE
Animals Low residues were found in nearly all ruminant and poultry tissues. Extensive metabolism was observed, with a large number of minor metabolites being produced Plants Limited metabolism in most plant species; minor metabolites indicate a pathway involving hydroxylation or oxidative loss of the tert-butyl group, followed by opening of the heterocyclic ring. Soil/Environment DT50 (25 ) 104 d (flooded conditions, silty clay loam, o.c. 3.8%, pH >6.4), 80 d (upland conditions, sandy loam, o.c. 2.4%, pH 7.0) (J. Pestic. Sci., 11, 605-610 (1986)).