Metominostrobin 苯氧菌胺

中文通用名称：苯氧菌胺
英文通用名称：metominostrobin （BSI建议名）fenominostrobin （BSI建议名）
商品名称：Oribright
化学名称：
(E)-2-甲氧亚氨基- N -甲基-2-(2-苯氧苯基)乙酰胺
(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide

CA主题索引名及CAS登录号：
(E)-α-methoxyimino-N-methyl-2-phenoxybenzeneacetamide
[133408-50-1]

化学结构类型：甲氧基丙烯酸酯类
理化性质：纯品为白色结晶体；熔点87~89℃；密度1.27~1.30(20℃)；蒸气压1.8×10-5Pa(25℃)；分配系数(20℃) LogP＝2.32；溶解度(20℃, g/l) 水0.128，二氯甲烷1380，氯仿1280，二甲亚砜940；对热、酸、碱稳定，遇光稍有分解。
毒性：
大鼠急性经口L D50：雄性776mg/kg，雌性708mg/kg； 大鼠急性经皮L D50：>2000mg/kg；大鼠吸入L C50(4小时)：>1880mg/l；本品对皮肤无刺激。鱼L C50(96小时)：鲤鱼17.5mg/l；水蚤L C50(48小时)：1.4mg/l。
制剂：GR、WP
作用机理：线粒体呼吸抑制剂即通过在细胞色素b和C1间电子转移抑制线粒体的呼吸。对14-脱甲基化酶抑制剂、苯甲酰胺类、二羧酰胺类和苯并咪唑类产生抗性的菌株有效。具有保护、治疗、铲除、渗透、内吸活性。
适宜作物：水稻
对作物安全性：推荐剂量下对作物安全、无药害。
防治对象：稻瘟病。
应用：SSF-126 是一种新型的广谱、保护和治疗活性兼有的内吸性杀菌剂。主要用于防治水稻稻瘟病等，在未感染或发病初期施用，使用剂量为500~2000克有效成分/公顷。
合成方法：
方法1：以邻甲苯酚为起始原料，经醚化、卤化、氰基取代、亚硝化、烷基化、酸解酯化、氨化即得SSF-126。

方法2：以水杨酸酯为起始原料，经醚化、水解、酰氯化、氰基取代、缩合、酸解酯化、氨化即得SSF-126。

主要原料与中间体：邻甲酚、溴代苯、氰化钠、甲胺、或水杨酸酯、溴代苯、甲氧基胺。
分析方法：GC或HPLC
开发公司：日本盐野义公司。

metominostrobin
Fungicide
FRAC 11, C3; strobilurin type: oximinoacetamide

NOMENCLATURE
Common name metominostrobin (BSI, pa ISO)
IUPAC name (E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide
Chemical Abstracts name (E)-a-methoxyimino-N-methyl-2-phenoxybenzeneacetamide
CAS RN [133408-50-1] Development codes SSF-126 (Shionogi)

PHYSICAL CHEMISTRY
Composition >97% pure. Mol. wt. 284.3 M.f. C16H16N2O3 Form White crystals. M.p. 87-89 °C V.p. 0.018 mPa (25 °C, gas saturation method) KOW logP = 2.32 (20 °C) S.g./density 1.27-1.30 (20 °C) Solubility In water 0.128 g/l (20 °C). In dichloromethane 1380, chloroform 1280, dimethyl sulfoxide 940 (all in g/l, 25 °C). Stability Stable to heat, and to acidic and alkaline media. Slightly unstable to light. F.p. 226 °C (Seta flash tester)

COMMERCIALISATION
History Discovered in 1989 by Shionogi Co., Ltd (whose agrochemical interests became Aventis CropScience Shionogi K.K in 2001, now part of Bayer CropScience). Registered in Japan in 1998.

APPLICATIONS
Biochemistry Respiratory electron transport inhibitor. Acts by inhibiting cytochrome pathway (Complex III) between cytochrome b and cytochrome c1, at the ubiquinol oxidising site. Mode of action Systemic fungicide with protective and curative action. Uses For control of Pyricularia oryzae on rice, at 1.5-1.8 kg/ha; applied before or at outbreak of infection symptoms. Formulation types GR; WP.

OTHER PRODUCTS
'Oribright' (Shionogi, Bayer CropScience)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 776, female rats 708 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Not a skin irritant; slight eye irritant (rabbits, 15% GR formulation). Not a skin sensitiser (15% GR formulation). Inhalation LC50 (4 h) for male and female rats >1880 mg/m3.

ECOTOXICOLOGY
Birds Acute oral LC50 for mallard ducks >5200 ppm. Fish LC50 (96 h) for carp 18.1 mg/l. Daphnia EC50 (48 h) for D. pulex 14.0 mg/l; (24 h) 22.3 mg/l. Algae EC50 (72 h) for Chlorella vulgaris 51.0 mg/l; NOEC (72 h) 10 mg/l. Bees LC50 (48 h) >100 mg/bee. Worms LC50 (14 d) for Eisenia foetida 114 mg/kg; NOEC (14 d) 56.2 mg/kg. Other beneficial spp. LC50 (5 d) for silkworms 250 ppm.

ENVIRONMENTAL FATE
Soil/Environment Soil DT50 98 d (aerobic).