Dinotefuran

NOMENCLATURE
Common name dinotéfurane ((m) F-ISO); dinotefuran (BSI, E-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] 
PHYSICAL CHEMISTRY
Mol. wt. 202.2 M.f. C₇H₁₄N₄O₃ Form White crystalline solid. M.p. 107.5 °C B.p. Decomp. 208 °C V.p. <1.7 × 10^-3 mPa (30 °C) K_ow logP = –0.549 (25 °C) Henry 8.7 × 10^-9 Pa m³ mol^-1 (calc.) S.g./density 1.40 Solubility In water 39.8 g/l (20 °C). In hexane 9.0 × 10^-6, heptane 11 × 10^-6, xylene 72 × 10^-3, toluene 150 × 10^-3, dichloromethane 61, acetone 58, methanol 57, ethanol 19, ethyl acetate 5.2 (all in g/l, 20 °C). Stability Stable at 150 °C (DSC). Hydrolysis DT₅₀ >1 y (pH 4, 7, 9). Photodegradation DT₅₀ 3.8 h (sterilised/natural water). pKa 12.6 (20 °C)
APPLICATIONS
Biochemistry Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the insect central nervous system. Mode of action Systemic insecticide with translaminar activity and with contact and stomach action. Readily taken up by the plant and further distributed acropetally. Uses Controls a range of sucking insects, such as whiteflies, plant bugs, leafhoppers and mealybugs; Coleoptera, such as Colorado Beetles and flea Beetles; Diptera, such as leaf miner flies; and certain Lepidoptera, such as fruit moths, in vegetables, fruit, paddy rice and turf. Can be applied on foliage, soil, nursery boxes and to paddy water by spray, drench, broadcast and pricking-in-hole treatments. Formulation types DL; DP; FL; GR; SG; SL; WP.
ENVIRONMENTAL FATE
Animals In rats, extensively absorbed and completely eliminated within 168 h, mainly via urine. Little metabolism occurred. Plants In lettuce, metabolites include 1-methyl-3-(tetrahydro-3-furylmethyl)guanidine and 1-methyl-3-(tetrahydro-3-furylmethyl)urea. Soil/Environment Aqueous photolysis DT₅₀ 1.8 d. Soil DT₅₀ 50–100 d. The major degradate is 1-methyl-2-nitroguanidine.
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. Slight eye and skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC₅₀ (4 h) for rats >4.09 mg/l. NOEL NOAEL (1 y) for male dogs 559, female dogs 22 mg/kg daily. ADI (EPA) aRfD 1.25, cRfD 0.02 mg/kg [2004]; (FSC) 0.22 mg/kg b.w. [2005] Other Not a mutagen, neurotoxin, carcinogen, teratogen or reproductive toxin.
ECOTOXICOLOGY
Birds Acute oral LD₅₀ for Japanese quail >2000 mg/kg. LC₅₀ (5 d) for mallard ducks >5000 ppm (997.9 mg/kg daily), Japanese quail >5000 ppm (1301 mg/kg daily). Fish LC₅₀ (96 h) for carp, rainbow trout and bluegill sunfish >100 ppm. Daphnia EC₅₀ (48 h) >1000 ppm. Algae E_bC₅₀ (72 h) for Pseudokirchneriella subcapitata >100 mg/l. Other aquatic spp. LC₅₀ (48 h) for crayfish 4.84 ppm. LC₅₀ (96 h) for eastern oysters 141, mysid shrimps 0.79 ppm. EC₅₀ for Lemna gibba >110 ppm. Bees Highly toxic to honeybees; LD₅₀ (oral) 0.023 μg/bee; (contact) 0.047 μg/bee (EPA Fact Sheet). Other beneficial spp. Highly toxic to silkworms.