Dinotefuran 21% + buprofezin 19% WDG

dinotefuran (265)
Insecticide
nitromethylene; neonicotinoid

NOMENCLATURE
Common name dinotefuran (BSI; pa ISO)
IUPAC name (RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine
Chemical Abstracts name N-methyl-N'-nitro-N''-[(tetrahydro-3-furanyl)methyl]guanidine
CAS RN [165252-70-0] Development codes MTI-446 (Mitsui)

PHYSICAL CHEMISTRY
Mol. wt. 202.2 M.f. C7H14N4O3 M.p. 94.5-101.5 癈 KOW logP = -0.644 (pH 7) S.g./density 1.33 Solubility In purified water 54.3?.3 g/l (20 癈). pKa No dissociation in range pH 1.4 to 12.3

COMMERCIALISATION
History Reported by K. Kodaka et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 1, 21). Under development by Mitsui Chemicals Inc. Patents EP 0649845 Manufacturers Mitsui

APPLICATIONS
Biochemistry Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the insect central nervous system. Mode of action Active by ingestion and by contact; also exhibits root-systemic activity. Uses Controls a range of hemipterous and other pests, at 100-200 g/ha.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 2804, female rats 2000, male mice 2450, female mice 2275 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Not a skin sensitiser (guinea pigs).

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks 1000, Japanese quail >2000 mg/kg. Fish LC50 (96 h) for carp >1000 ppm; (48 h) for rainbow trout >40 ppm. Daphnia (48 h) 1000 ppm Other aquatic spp. LC50 (48 h) for crayfish 5-10 ppm.

buprofezin (97)
Insecticide, acaricide



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NOMENCLATURE
Common name buprofezin (BSI, draft E-ISO); buprof閦ine ((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)

PHYSICAL CHEMISTRY
Composition Tech. is 99.1%. Mol. wt. 305.4 M.f. C16H23N3OS Form White crystals; (tech., white or pale yellow crystalline powder). M.p. 104.5-105.5 篊 V.p. 1.25 mPa (25 篊) KOW logP = 4.3 Henry 4.24 ?10-1 Pa m3 mol-1 (calc.) S.g./density 1.18 (20 癈) Solubility In water 0.9 mg/l (25 篊). In chloroform 520, benzene 370, toluene 320, acetone 240, ethanol 80, hexane 20 (all in g/l, 25 篊). Stability Stable in acidic and alkaline media. Stable to heat and light.

COMMERCIALISATION
History Insecticide reported by H. Kanno et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1981, 1, 59). Introduced by Nihon Nohyaku Co., Ltd. Manufacturers Nihon Nohyaku

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)

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 癈) 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)).