Chlozolinate 乙菌利

乙菌利

CAS号：84332-86-5
英文名称：chlozolinate
化学名称：（±）3-（3，5-二氯苯基）-5-甲基-2，4-二氧代-1，3-恶唑烷-5-羧酸乙酯；ethyl 3-(3,5-dichlorophenyl)-5- methyl-2,4-dioxo-5-oxazolidinecarboxyate
其他名称：克氯得
分子式： C13H11Cl2NO5
分子量：332.1

理化性质：无色固体。熔点113～114℃。相对密度1.42。蒸气压0.013mPa(25℃)。溶解性(25℃)：水32mg/L，丙酮、氯仿、二氯甲烷>300g/kg，己烷3g/kg，甲醇10g/kg。在氮气保护下，低于250℃稳定；对光稳定。其水溶液在pH值5～9时水解。

毒性LD50(mg/kg)：大鼠急性经口LD50大于4500，小鼠大于10000，大鼠急性经皮LD50(24h)大于5000。本品对兔眼睛和皮肤无刺激．无致畸、致突变、致癌作用。大鼠急性吸入LC50大于10mg/L空气。饲喂试验的无作用剂量：大鼠(90天)200mg/kg饲料，狗(0.5年)27.5mg/L。急性经口LD50鹌鹑和野鸭＞4.5g/gk。鱼毒：鳟鱼LC50(96小时)27.5mg/L。蜜蜂LD50(经口)＞100μg/蜜蜂。水蚤LC50(48小时)1.18mg/L。

作用特点及用途：乙菌利属3，5-二氯苯胺类杀菌剂，作用于细胞膜，抑制菌体内甘油三酯的合成，用于防治灰葡萄孢和核盘菌属菌以及观赏植物的某些病害。推荐用于葡萄、草莓防治灰葡萄孢，核果和仁果类桃褐腐核盘菌和果产核盘菌，蔬莱上的灰葡萄孢和核盘菌属，用量0.75～1.0kg（a.i.）/ha。可防治禾谷类叶部病害和种传病害，如小麦腥黑穗病、大麦和燕麦的散黑穗病，也可防治苹果黑垦病和玫瑰白粉病等。

剂型：制剂有20％、50％可湿性粉剂，30％悬浮剂。

生产方法：由溴化乙基镁与丙酮二酸二乙酯在四氢呋喃中、-70℃下反应制得甲基丙醇二酸二乙酯；再同3，5-二氯苯基异氰酸酯于苯中，在三乙胺存在下反应，处理即得乙菌利。

chlozolinate
Fungicide
FRAC 2, F1; dicarboximide

NOMENCLATURE
Common name chlozolinate (BSI, draft E-ISO, (m) draft F-ISO)
IUPAC name ethyl (?-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-oxazolidine-5-carboxylate
Chemical Abstracts name (?-ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-5-oxazolidinecarboxylate
CAS RN [84332-86-5] racemate; [72391-46-9] unstated stereochemistry EEC no. 282-714-4 Development codes M 8164 (Agrimont)

PHYSICAL CHEMISTRY
Mol. wt. 332.1 M.f. C13H11Cl2NO5 Form Colourless, almost odourless solid. M.p. 112.6 °C V.p. 0.013 mPa (25 ºC, gas saturation method) KOW logP = 3.15 (22 °C) Henry 2.29 ´ 10-3 Pa m3 mol-1 (25 °C, calc.) S.g./density 1.441 (20 °C) Solubility In water c. 2 ppm (25 °C). In acetone, ethyl acetate and 1,2-dichloroethane >250, ethanol c. 13, n-heptane c. 2, xylene c. 60 (all in g/kg, 22 °C). Stability Stable to 250 ºC (under nitrogen). Stable to light. In solution, hydrolysis occurs at pH 5-9.

COMMERCIALISATION
History Fungicide reported by Di Toro et al. (Atti Giornate Fitopatol., Siusi, 1980). Introduced by Agrimont (now Isagro S.p.A.). Patents BE 874406; DE 2906574; IT 20579/78 Manufacturers Isagro

APPLICATIONS
Biochemistry Lipid peroxidation in mitochondrial membranes. Mode of action Contact fungicide with protective and curative action. Uses Control of Botrytis spp., Sclerotinia spp., and Monilia spp. in ornamentals, vegetables, vines, pome fruit, stone fruit, sunflowers and strawberries. Can be applied, at 750-1000 g/ha, as a foliar spray or as a soil drench. Formulation types SC; WP. Selected products: 'Manderol' (Isagro); 'Serinal' (Isagro)

ANALYSIS
Product and residues can be determined by glc. Details are available from Isagro.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >4500, mice >10 000 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 >10 mg/l air. NOEL (90 d) for rats 200 mg/kg diet; (1 y) for dogs 200 mg/kg diet. Other Not mutagenic, not teratogenic. Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification R40| N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for quail and mallard ducks >4500 mg/kg. Fish LC50 (96 h) for trout 27.5 mg/l. Daphnia LC50 (48 h) 1.18 mg/l. Algae EC50 (96 h) for Selenastrum capricornutum 30 mg/l. Bees LD50 (oral) >100 mg/bee. Other beneficial spp. Harmless to Phytoseiulus persimilis at up to 2 ´ recommended application rate.

ENVIRONMENTAL FATE
Animals Chlozolinate is readily absorbed, metabolised and excreted. Metabolites identified in urine of rats are: 3-(3,5-dichlorophenyl)-5-methyloxazolidin-2,4-dione, N-(3,5-dichlorophenyl)-2-hydroxypropionamide, O-1-carboxyethyl-N-3,5-dichlorophenyl carbamate, and N-(3,5-dichloro-2(or 4)-hydroxyphenyl)-2-hydroxypropionamide and its sulfate and glucuronide conjugates. Plants In plants, chlozolinate undergoes hydrolysis and decarboxylation processes, giving the same metabolites as those identified in animals. Soil/Environment In silt-loam, sandy loam and clay loam soils, hydrolysis and decarboxylation occur; aerobic DT50 <7 h.