Fenhexamid 环酰菌胺

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中文通用名称: 环酰菌胺
英文通用名称: fenhexamid
商品名称: Elevate、Password、Teldor
试验代号: K B R 2738
化学名称:
N-(2,3-dichloro-4- hydrophenyl)-1-methyl-cyclohexanecarboxamide
N-(2,3-二氯-4- 羟基苯基)-1-甲基-环己基甲酰胺
CA主题索引名及CAS登录号:
1-methyl-cyclohexanecarboxylic acid (2,3-dichloro-4-hydrophenyl)- amide
[126833-17-8]

化学结构类型:酰胺类

毒性:
大鼠急性经口L D50:雄>5000mg/kg;大鼠急性经皮LD50(24小时):>2000mg/kg;大鼠急性吸入LC50(4小时):>5057mg/kg空气;本品对兔眼睛和皮肤无刺激。无致畸、致癌性。

制剂:50% WG、 50% SC、 50%WP

作用机理:
具体作用机理尚不清楚。但大量的研究表明其具有独特的作用机理,与已有杀菌剂苯并咪唑类、二羧酰亚胺类、三唑类、苯胺嘧啶类、N -苯基氨基甲酸酯类等无交互抗性。

适宜作物及对作物的安全性: 葡萄、硬果、草莓、蔬菜、柑桔、观赏植物等。对作物、人类、环境安全,是理想的综合害物治理用药。

防治对象:各种灰霉病以及相关的菌核病、黑斑病等。
应用:本品主要作为叶面杀菌剂使用,其剂量为500~1000克有效成分/公顷,对灰霉病有特效。

合成方法:
以2,3-二氯硝基苯为起始原料,经还原、羟基化制得中间体取代的氨基苯酚,再经酰氨化即得目的物。反应式为:

主要原料与中间体: 2,3-二氯硝基苯、α-甲基环己基甲酰氯
分析方法: GC/HPLC

专利与登记: EP 569792, 该品种首先在英国获准登记,亦在美国、加拿大销售。
开发公司: 拜耳公司

 

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fenhexamid
Fungicide
FRAC 17, G3; hydroxyanilide

  Fenhexamid

NOMENCLATURE
Common name fenhexamid (BSI, pa ISO)
IUPAC name 2',3'-dichloro-4'-hydroxy-1-methylcyclohexanecarboxanilide
Chemical Abstracts name N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide
CAS RN [126833-17-8] Development codes KBR 2738 (Bayer)

PHYSICAL CHEMISTRY
Composition >95% pure. Mol. wt. 302.2 M.f. C14H17Cl2NO2 Form White powder. M.p. 153 °C B.p. 320 °C (extrapolated) V.p. 4 ´ 10-4 mPa (20 °C, extrapolated) KOW logP = 3.51 (pH 7, 20 °C) Henry 5 ´ 10-6 Pa m3 mol-1 (pH 7, 20 °C, calc.) S.g./density 1.34 (20 °C) Solubility In water 20 mg/l (pH 5-7, 20 °C). In dichloromethane 31, isopropanol 91, acetonitrile 15, toluene 5.7, n-hexane <0.1 (all in g/l, 20 °C). Stability Stable to hydrolysis for 30 d at pH 5, 7, 9 (25 °C).

COMMERCIALISATION
History Discovered by Bayer AG in 1989. Reported by H-J. Rosslenbroich et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 327). First marketed in 1998. Patents EP 339418 Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry Biochemical target is sterol biosynthesis (SBI class III), acting on 3-keto-reductase during C4-demethylation, displaying a low to moderate risk for resistance development. Inhibits germ tube elongation and mycelium growth. Mode of action Foliar fungicide with protectant action; not translocated. Uses For control of Botrytis cinerea, Monilia spp. and related pathogens in grapes, berries, stone fruit, citrus, vegetables and ornamentals, at 500-1000 g/ha. Formulation types SC; WG; WP. Selected products: 'Decree' (in co-operation with Bayer) (Arvesta); 'Elevate' (in co-operation with Bayer) (Arvesta); 'Password' (Nihon Bayer); 'Teldor' (Bayer CropScience); mixtures: 'Talat' (+ tolylfluanid) (Bayer CropScience)

OTHER PRODUCTS
Mixtures: 'Dyemazine' (+ iminoctadine tris(albesilate)) (Japan) (Bayer CropScience); 'Justeet' (+ fludioxonil) (Japan) (Bayer CropScience); 'Young-gune' (+ tebuconazole) (spray, Korea) (Kyung Nong)

ANALYSIS
Method for determination in plant material by lc described by F. Nuesslein, Pflanzenschutz-Nachr. Bayer, 1999, 52, 2.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5057 mg/m3 air (dust) NOEL (24 mo) for rats 500, mice 800 mg/kg diet; (12 mo) for dogs 500 mg/kg diet. ADI 0.183 mg/kg b.w. Other Non-teratogenic, non-carcinogenic, non-mutagenic. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail and mallard duck >5000 ppm of feed. Fish LC50 (96 h) for rainbow trout 1.34, bluegill sunfish 3.42 mg/l. Daphnia EC50 (48 h) >18.8 mg/l. Algae ErC50 (120 h) for Selenastrum capricornutum 8.81 mg/l. ErC50 (72 h) for Scenedesmus subspicatus >26.1 mg/l. Other aquatic spp. NOEC (28 d) for Chironomus riparius 100 mg/l; EC50 (14 d) for Lemna gibba 2.3 mg/l. Bees LC50 (oral and contact) >200 mg/bee. Worms LC50 (2 w) for Eisenia foetida >1000 mg/kg dry soil. Other beneficial spp. Not toxic to predatory mites (Typhlodromus pyri), rove beetles (Aleochara bilineata), ladybirds (Coccinella septempunctata) and parasitoids (Aphidius rhopalosiphi), at 2 kg/ha. No adverse effect on microbial mineralisation.

ENVIRONMENTAL FATE
All data indicate that there is no danger to the consumer from fenhexamid residues. Animals In rats, rapidly absorbed and eliminated without accumulation within 48 h. The major elimination followed the faecal route (61%), whereas renal excretion accounted for 15-36% of the total administered dose. Plants The metabolic pathway is similar in all crops; in all plant samples, the unchanged active ingredient was identified as the largest single constituent. Soil/Environment DT50 in soil £1 d (4 soils, 20 °C). Studies and calculation show that the compound can be classified as having no, or only low, leaching potential; no problems of groundwater contamination will be expected. In sterile aquatic systems, fenhexamid was stable to hydrolysis. In natural water/sediment systems, fenhexamid degrades rapidly and completely, ultimately forming CO2; overall DT50 (calc.) was a few days (C. Anderson, et al., Pflanzenschutz-Nachr. Bayer, 1999,52, 2).