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Insecticides

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Acetamiprid

IRAC 4A neonicotinoid

NOMENCLATURE
Common name acétamipride ((m) F-ISO); acetamiprid (BSI, E-ISO) IUPAC name (E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine
Chemical Abstracts name (E)-N-[(6-chloro-3-pyridinyl)methyl]-N′-cyano-N-methylethanimidamide CAS RN [135410–20–7]; [160430–64–8] unspecified stereochemistry Development codes NI-25 (Nippon Soda); EXP60707B Smiles code CN(Cc1ccc(Cl)nc1)C(=NC#N)C
PHYSICAL CHEMISTRY
Mol. wt. 222.7 M.f. C10H11ClN4 Form White crystals. M.p. 98.9 °C V.p. <1 × 10-3 mPa (25 °C) Kow logP = 0.80 (25 °C) Henry <5.3 × 10-8 Pa m3 mol-1 (calc.) S.g./density 1.330 (20 °C) Solubility In water 4250 mg/l (25 °C). Soluble in acetone, methanol, ethanol, dichloromethane, chloroform, acetonitrile and tetrahydrofuran. Stability Stable in buffered solutions at pH 4, 5, 7. Degraded slowly at pH 9 and 45 °C. Stable under sunlight. pKa 0.7, v. weak base
COMMERCIALISATION
History Reported by H. Takahashi et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 89). Registered in Japan in 1995 and introduced by Nippon Soda Co., Ltd. Patents US 5304566 Manufacturers AgroDragon; Aimco; Anhui Huaxing; Astec; Fengshan; Fertiagro; Hailir; Hebei Kaidi; Hebei Veyong; Honbor; Hubei Sanonda; Jiangsu Changqing; Jiangsu Kuaida; Jiangsu Yangnong; Meghmani; Qingdao Kyx; Red Sun; Sanonda Zhengzhou; Sega; Shanghai Shengnong; Sharda; Sinochem Ningbo; Sudarshan; Tenglong; Xinyi Zhongkai; Yancheng Limin; Ningbo Finechem; Nippon Soda; Zhejiang Hisun
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. Uses Control of Hemiptera, especially aphids, Thysanoptera and Lepidoptera, by soil and foliar application, on a wide range of crops, especially vegetables, fruit and tea. Applied at 75–300 g/ha on vegetables, 100–700 g/ha in orchards. Formulation types EC; FU; GR; SP; WP; FS; SL; SG.
PRODUCTS
Selected products ‘Dyken’ (Heranba) ; ‘Fertilan’ (Fertiagro) ; ‘Masuta’ (Crop Health) ; ‘Mospilan’ (Nippon Soda) ; ‘Mospildate’ (Mobedco) ; ‘Suntamiprid’ (Sundat) ; ‘Vapcomere’ (Vapco) ; ‘Pride’ (Nippon Soda) Other products ‘Aceta’ (United Phosphorus) ; ‘Active’ (Devidayal) ; ‘Albis’ (Atul) ; ‘Alphachem’ (Chemvet) ; ‘Assail’ (Nippon Soda, United Phosphorus Inc.) ; ‘Convence’ (Iharabras) ; ‘Ekka’ (Krishi Rasayan) ; ‘Epik’ (Sipcam Inagra, Sipcam S.p.A.) ; ‘Gazel’ (Nippon Soda) ; ‘Gazelle’ (Nippon Soda) ; ‘Hekplan’ (Hektaş) ; ‘Intruder’ (DuPont, Nippon Soda) ; ‘Lift’ (Indofil) ; ‘Manik’ (Rallis) ; ‘Mortal’ (Vapco) ; ‘Pilarmos’ (Pilarquim) ; ‘Pirâmide’ (Iharabras) ; ‘Platinum’ (Aimco) ; ‘Profil’ (Nippon Soda) ; ‘Rescate’ (Nippon Soda) ; ‘Saurus’ (Nippon Soda) ; ‘Scuba’ (Coromandel) ; ‘Suprême’ (Nippon Soda) ; ‘Tackil’ (Biostadt) ; ‘Theme’ (Ramcides) ; ‘Tristar’ (Nippon Soda) ; ‘Zhuangxi’ (Fengshan) mixtures ‘Transport’ (+ bifenthrin) (Nippon Soda, Nippon Soda) ; ‘Justice’ (+ bifenthrin) (Nippon Soda, Nippon Soda) Discontinued products ‘Adjust *’ (Bayer CropScience) ; ‘Nison *’ (AGROFINA) ; ‘Pristine *’ (Aventis)
ANALYSIS
Product by hplc with uv detection (CIPAC Handbook, 2006, L, 4). Residues by glc. Residues in soil by lc/ms/ms (Environ. Chem. Methods); in water by hplc with uv detection (ibid.).
ENVIRONMENTAL FATE
Animals Rapidly and almost completely absorbed (>96% after 24 h) and rapidly and almost completely excreted (90% after 96 h), mainly via urine. Extensively (>90%) metabolised, mainly by oxidation and demethylation. Plants Slowly degraded on or in plants, forming five identified metabolites (H. Saito et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 2, 5A-010). Soil/Environment Acetamiprid is moderately to highly mobile in most soils but is not expected to be persistent in the environment. The primary degradation pathway is aerobic soil metabolism. DT50 0.8–5.64 d, DT90 2.8–67.3 d (20 °C, EU 9 soils). Koc 71.1–313 (US and EU soils).
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EU Rev. Rep. SANCO/1392/2001, June 2004. EPA Fact Sheet, Mar. 2002. EU Status (1107/2009) Approved, 2004/99/EC.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 217, female rats 146, male mice 198, female mice 184 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male and female rats >1.15 mg/l. NOEL (2 y) for rats 7.1 mg/kg b.w.; (18 mo) for mice 20.3 mg/kg b.w.; (1 y) for dogs 20 mg/kg b.w. ADI (EC) 0.07 mg/kg [2004]; (EPA) aRfD 0.10, cRfD 0.07 mg/kg b.w. [2005]. Other Negative in the Ames test. EC classification Xn; R22| R52, R53. (Xn; R20, R22| R52, R53)
ECOTOXICOLOGY
Birds LD50 for mallard ducks 98, bobwhite quail 180 mg/kg. LC50 for bobwhite quail >5000 ppm. Fish LC50 (0–96 h) for carp >100 mg/l. Daphnia LC50 (24 h) >200 mg/l; EC50 (48 h) 49.8 mg/l. Algae ErC50 (72 h) for Scenedesmus subspicatus >98.3 mg/l; NOEC (72 h) 98.3 mg/l. Other aquatic spp. EC50 (14 d) for Lemna gibba 1.0 mg/l (EU Rev. Rep.). Bees LD50 (oral) 14.5 μg/bee; (contact) 8.1 μg/bee (EU Rev. Rep.). Other beneficial spp. Harmful to some beneficial arthropod species (see EU Rev. Rep.).

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