Fenoxanil 氰菌胺 稻瘟酰胺

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其他名称:稻瘟酰胺;ICI A001,Achi-Bu
毒性:大鼠急性经口LD50:雄 >5000㎎/㎏,雌 4211㎎/㎏;小鼠急性经口LD50>5000㎎/㎏;大鼠急性经皮LD50>2000㎎/㎏;对兔眼睛和皮肤无刺激作用。对鱼等安全,鲤鱼LC50(96h):10.1mg/l,鹌鹑LD50 >2000mg/kg.

氰菌胺是一个新颖的用于防治水稻稻瘟病的内吸性杀菌剂.,具有新颖作用机制,属于黑色素生物合成抑制剂(MBI),在叶面和水下施用时防治稻瘟病效果极佳,且持效显著。主要用于防治水稻稻瘟病, 包括叶瘟和穂瘟,最佳施药时间应在发病前7-10天,或在抽穗前5-30天。灌施剂量通常为2100-2800ga.i./hm,茎叶处理,使用剂量为200-400 ga.i./hm。瘟。与保护性杀菌剂混用,可防治葡萄霜霉病、马铃薯和番茄晚疫病。


氰菌胺系由日本农药公司与巴斯夫公司(原美国氰胺公司)在1995年共同开发成功的内吸传导型稻瘟病防治药剂。最早由原氰胺公司所发明。该产品在2000年12月获准登记。国内生产企业:山东京博农化有限公司(200t/a); 南京仁信化工有限公司; 江苏丰登农药有限公司(500t/a); 江苏长青农化股份有限公司 ; 杭州易隆化工有限公司


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FRAC 16.2, I2; MBI: dehydratase


Common name fenoxanil (BSI, pa ISO)
IUPAC name a mixture of 85% (R)-N-[(RS)-1-cyano-1,2-dimethylpropyl]-2-(2,4-dichlorophenoxy)propionamide and 15% (S)-N-[(RS)-1-cyano-1,2-dimethylpropyl]-2-(2,4-dichlorophenoxy)propionamide
Chemical Abstracts name N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propanamide
CAS RN [115852-48-7] Development codes AC 382042; CL 382042; AC 901216 (all Cyanamid); WL 378309 (Shell); NNF-9425 (Nihon Nohyaku); BAS 546 F (BASF)

Composition A mixture of (R,R) and (R,S) diastereoisomers as major components, and (S,R and S,S) diastereoisomers as minor components. Mol. wt. 329.2 M.f. C15H18Cl2N2O2 Form Off-white, odourless solid. M.p. 69.0-72.5 °C V.p. 0.21?.021 ´ 10-4 mPa (25 °C) KOW logP = 3.53?.02 (25 °C) S.g./density 1.22 (20 °C) Solubility In water 30.7?.3 ´ 10-3 g/l (20 °C). Soluble in most organic solvents. Stability Essentially stable within the relevant pH range. F.p. 420 °C (OPPTS 830.6315)

History Discovered by Shell GmbH and acquired by American Cyanamid Co. (now BASF AG). Reported by E. Sieverding et al., (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 359). Developed jointly by BASF and Nihon Nohyaku Co., Ltd. Manufacturers BASF

Biochemistry Melanin biosynthesis inhibitor. Inhibits dehydratase enzymes which dehydrate scytalone to trihydroxynaphthalene and vermelone to dihydroxynaphthalene. Mode of action Systemic, protective fungicide with residual effects. Uses Controls rice blast by foliar or into-water application, at 120-150 g/ha and 2.4-2.7 kg/ha respectively. Formulation types DL; GR; SC. Selected products: 'Achi-Bu' (Nihon Nohyaku); 'Achieve DL' (Nihon Nohyaku); 'Byochonguk' (BASF); 'Helmet' (BASF); 'Stopper' (BASF)

Mixtures: 'Achieve Moncut F' (+ flutolanil) (Nihon Nohyaku); 'Achieve Moncut Trebon' (+ flutolanil+ etofenprox) (Nihon Nohyaku)

Product analysis by chiral hplc (Cyanamid method No. M-3446). Residues in rice grain and straw, by glc with NPD detection (Nihon Nohyaku unpublished report DE-49-97-0021); in soil, by hplc (Nihon Nohyaku unpublished report LSRC-R97-148A).

Oral Acute oral LD50 for male rats >5000, female rats 4211, male and female mice >5000 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 for rats >5.18 mg/l. NOEL NOAEL (1 y) for dogs 1 mg/kg; (2 y) for male rats 0.698 mg/kg, female rats 0.857 mg/kg, non-carcinogenic; (18 month) for male mice 6.98 mg/kg, female mice 6.648 mg/kg, (hepatocellular carcinoma at 500 ppm dose group); (2 generation) for male rats 1.124 mg/kg, female rats 1.74 mg/kg, (no effect on reproduction); teratology for rats 50 mg/kg (parent), 250 mg/kg (foetus), for rabbits 10 mg/kg (parent), 200 mg/kg (foetus). ADI 0.0069 mg/kg b.w. Other Non-mutagenic in Ames, DNA repair, chromosome aberration and mouse micronucleus tests. Non-teratogenic.

Birds NOEL for quail >2000 mg/kg. Fish LC50 (96 h) for Japanese medaka (Oryzias latipes) 5.90, asian pond loach (Misgurnus anguillicaudatus) 12.3 mg/l. Daphnia EC50 (48 h) 6.0 mg/l. Algae EC50 (72 h) for Selenastrum capricornutum >7.0 mg/l. Other aquatic spp. LC50 (96 h) for Minaminuma shrimp (Neocaridina denticulate) 7.9, crayfish (Procambarus clarkii) >100, Numa frog tadpoles (Rana limnocharis) 8.54 mg/l; LC50 (120 h) for Shijimi clam (Corbicula learna) 8.16, Japanese littleneck (Tapes philippinarum) 1.78 mg/l. Worms LC50 (14 d) 71 mg/kg of soil.

Animals In rats, orally administered fenoxanil is readily adsorbed, distributed, and extensively metabolised through hydroxylation, hydrolysis and, following conjugation, excreted into faeces and urine. Plants In rice, the primary residue recovered from grain, hull and straw is parent compound. Fenoxanil that is metabolised is transformed by hydration of the amide moiety, hydroxylation of the isopropyl moiety and phenyl ring, and amide hydrolysis. The metabolite produced through hydroxylation of the phenyl ring is partially further metabolised through glucose conjugation. Soil/Environment In the laboratory, DT50 in clay loam and sandy clay loam soils 117 and 84 d respy. In field studies, soil DT50 4 d to <1 d. Koc 454-697; Kd 370. Hydrolytically stable at all pH values, and <50 °C. Aqueous photolysis DT50 41 d in natural water.