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Insecticides

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Emamectin

IRAC 6 avermectin

NOMENCLATURE
emamectin benzoate
CAS RN [155569-91-8], formerly [137512-74-4] and [179607-18-2] Development codes MK 244 (Merck & Co.) Smiles code B1a, without stereochemistry:CCC(C)C1OC2(CC3CC(CC = C(C)C(OC4CC(OC)C(OC5CC(OC)C([NH2+]C)C(C)O5)C(C)O4)C(C)C = CC = C6COC7C(O)C( = CC(C( = O)O3)C76O)C)O2)C = CC1C.[O-]C( = O)c1ccccc1;B1b, without stereochemistry: C[NH2+]C1C(C)OC(CC1OC)OC2C(C)OC(CC2OC)OC3C(C)C = CC = C4COC5C(O)C( = CC(C( = O)OC6CC(CC = C3C)OC7(C6)OC(C(C)C)C(C)C = C7)C54O)C.[O-]C( = O)c1ccccc1
emamectin
Common name emamectin (BSI, E-ISO, ANSI); emamectine ((f) F-ISO) IUPAC name A mixture containing 90% of (10E,14E,16E)-(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)-6′-[(S)-sec-butyl]-21,24-dihydroxy-5′,11,13,22-tetramethyl-2-oxo-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2′-(5′,6′-dihydro-2′H-pyran)-12-yl 2,6-dideoxy-3-O-methyl-4-O-(2,4,6-trideoxy-3-O-methyl-4-methylamino-α-L-lyxo-hexopyranosyl)-α-L-arabino-hexopyranoside and 10% of (10E,14E,16E)-(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)-21,24-dihydroxy-6′-isopropyl-5′,11,13,22-tetramethyl-2-oxo-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2′-(5′,6′-dihydro-2′H-pyran)-12-yl 2,6-dideoxy-3-O-methyl-4-O-(2,4,6-trideoxy-3-O-methyl-4-methylamino-α-L-lyxo-hexopyranosyl)-α-L-arabino-hexopyranoside
Chemical Abstracts name (4′′R)-5-O-demethyl-4′′-deoxy-4′′-(methylamino)avermectin A1a + (4′′R)-5-O-demethyl-25-de(1-methylpropyl)-4′′-deoxy-4′′-(methylamino)-25-(1-methylethyl)avermectin A1a (9:1); 4′′-deoxy-4′′-(methylamino)avermectin B1 CAS RN [119791-41-2], formerly [123997-28-4] and [137335-79-6]
PHYSICAL CHEMISTRY
Composition A mixture of emamectin B1a (≥90%) and emamectin B1b (≤10%), as their benzoate salts. Mol. wt. 1008.3 (B1a); 994.2 (B1b) M.f. C56H81NO15 (B1a); C55H79NO15 (B1b) Form White to off-white powder. M.p. 141-146 °C V.p. 4 × 10-3 mPa (21 °C) Kow logP = 5.0 (pH 7) Henry 1.7 × 10-4 Pa m3 mol-1 (pH 7, calc.) S.g./density 1.20 (23 °C) Solubility In water 0.024 g/l (pH 7, 25°C). Stability Stable to hydrolysis at pH 5, 6, 7 and 8 (25 °C). Photodegrades rapidly. pKa 4.18 (acidic, attributed to benzoate counter ion), 8.71 (basic, calc., attributed to emamectin moiety)
emamectin
Mol. wt. 886.1 (B1a); 872.1 (B1b) M.f. C49H75NO13 (B1a); C48H73NO13 (B1b)
COMMERCIALISATION
Production Isolated from fermentation of Streptomyces avermitilis, a naturally occurring soil Actinomycete. History Discovery and initial development was by Merck & Co., Inc. (now Syngenta AG). First sales in Israel and Japan in 1997. Manufacturers Syngenta; CAC; Dalian Raiser; Golden Harvest; Hailir; Hebei Veyong; Honbor; Hui Kwang; Iprochem; Jiangsu Seven Continent; Jingbo; Sega; Zhejiang Hisun
APPLICATIONS
emamectin benzoate
Biochemistry Acts by stimulating the release of γ-aminobutyric acid, an inhibitory neurotransmitter, thus finally activating chloride channels. Mode of action Non-systemic insecticide which penetrates leaf tissues by translaminar movement. Paralyses Lepidoptera, which stop feeding within hours of ingestion, and die after 2-4 days. Uses For control of Lepidoptera on vegetables, brassicas, fruit, maize, tea, grapes and cotton, at up to 16 g/ha, and in pine trees, at 5-25 g/ha. Formulation types EC; SG.
PRODUCTS
emamectin benzoate
Selected products 'Affirm' (Syngenta) ; 'Denim' (Syngenta) ; 'Proclaim' (Syngenta) ; 'Missile' (Crystal Phosphates) Other products 'Banlep' (Syngenta) ; 'EM-1' (Dhanuka) ; 'Emma' (Hui Kwang) ; 'Prabhaav' (Rallis) ; 'Spolit' (United Phosphorus) mixtures 'Gardy AL' (+ thiamethoxam + difenoconazole) (Syngenta, Syngenta, Syngenta) ; 'Hana Hanayaka' (+ thiamethoxam + difenoconazole) (Syngenta, Syngenta, Syngenta)
ANALYSIS
Product and residues determined by hplc; see Resid. Anal. Methods. Details available from Syngenta.
ENVIRONMENTAL FATE
Animals Emamectin benzoate is partially metabolised but rapidly cleared (DT50 following oral dosing 34-51 h), indicating that it has no potential for bioaccumulation. Plants Metabolism has been investigated in lettuce, cabbage and sweetcorn. It is non-systemic, and rapidly degrades in sunlight to various complex residues in which undegraded parent is the only significant residue. The residues were very low. Soil/Environment Rapidly degraded.
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EU Rev. Rep. SANCO/1982/2007; EC DAR (Feb 2012). EU Status (1107/2009) Dossier complete, 07/669/EC.
MAMMALIAN TOXICOLOGY
emamectin benzoate
Oral Acute oral LD50 for rats 56-63 mg/kg. Skin and eye Acute dermal LD50 for rats >2000 mg/kg. Not irritant to skin; severe eye irritant. No sensitising potential. Inhalation LC50 (4 h) for rats >1.05-0.66 mg/l. NOEL (1 y) for dogs 0.25 mg/kg b.w. ADI 0.0025 mg/kg. Other Not tumorigenic. Toxicity class WHO (a.i.) II (company classification).
ECOTOXICOLOGY
emamectin benzoate
Birds Acute oral LD50 for mallard ducks 76, bobwhite quail 264 mg/kg. Dietary LC50 (8 d) for mallard ducks 570, bobwhite quail 1318 ppm. Fish LC50 (96 h) for rainbow trout 174, sheepshead minnows 1430 μg/l. Daphnia LC50 (48 h) 0.99 μg/l. Bees Toxic to bees. Worms LC50 >1000 mg/kg dry soil. Other beneficial spp. Safe to a wide range of beneficial insects, due to rapid breakdown of the a.i., limiting contact activity to <48 h.

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