Diflumetorim 氟嘧菌胺

中文通用名称: 氟嘧菌胺
英文通用名称: difulmetorim （ISO建议名）
商品名称: Pyricut

化学名称:
(RS)-5-氯-N-[1-[4-(二氟甲氧基)苯基]丙基]-6-甲基-4-嘧啶胺
(RS)-5-chloro-N-[1-[4-(difluoromethoxy)phenyl]propyl]-6-methyl-4-pyrimidi-namine

CA主题索引名及CAS登录号:
(±)-5-chloro-N-[1-[4-(difluoromethoxy)phenyl]propyl]-6-methyl-4-pyrimidinamine
[130339-07-0]

化学结构类型: 嘧啶胺类
理化性质: 纯品为淡黄色结晶体，熔点46.9~48.7℃；密度0.49(20℃)；蒸气压3.21×10-4Pa(25℃)；分配系数(25℃) LogP＝0.62；水中溶解度为0.033g/l(25℃)；离解常数pKa=4.5。

毒性:
大鼠急性经口L D50：雄448mg/kg, 雌534mg/kg； 小鼠急性经口L D50：雄468mg/kg, 雌387mg/kg；大鼠急性经皮L D50：雄>2000mg/kg, 雌>2000mg/kg；大鼠急性吸入L C50：雄0.61mg/l, 雌0.61mg/l。本品对兔眼睛和皮肤有轻微刺激。野鸭急性经口L D50：1979mg/kg； 鱼毒L C50：虹鳟0.025mg/l，鲤鱼0.098mg/l；水蚤 LC50：0.2mg/l。 Ames试验呈阴性，微核及细胞体外试验呈阴性。

制剂: 10％乳油。

作用机理:Difulmetorim对无性孢子的萌发至分生孢子柄的形成的任意阶段均有快速抑制作用，具体的作用机理在研究中。其化学结构有别于现有的杀菌剂，同三唑类、二硫代氨基甲酸酯类、苯并咪唑类及其它类包括抗生素等无交互抗性，因此其对敏感或抗性病原菌均有优异的活性。

适宜作物:禾谷类作物、观赏植物如玫瑰、菊花等对作物安全性对51种玫瑰、17种菊花安全、无药害

防治对象:白粉病和锈病等
使用方法: Difulmetorim经多年验证对小麦白粉病、小麦锈病、玫瑰白粉病、菊花锈病等具有优异的保护活性，使用浓度为50~100ppm，防治玫瑰白粉病推荐浓度50ppm，防治菊花锈病推荐浓度100ppm。发病前或发病初期喷雾处理

合成方法:
以乙酰乙酸乙酯为起始原料制得中间体取代的4-氯嘧啶 （1） 与以苯酚为起始原料制备的取代苄胺反应，即得目的物difulmetorim。反应式为：
主要原料与中间体乙酰乙酸乙酯、二氟甲氧基苯、丙酰氯

分析方法:G C或 HPLC
开发公司: 日本宇部兴产公司发现，由宇部兴产公司和日产化学公司共同开发。

diflumetorim
Fungicide
FRAC U3, C1; pyrimidinamine

NOMENCLATURE
Common name diflumetorim (BSI, pa ISO)
IUPAC name (RS)-5-chloro-N-[1-(4-difluoromethoxyphenyl)propyl]-6-methylpyrimidin-4-ylamine
Chemical Abstracts name (?-5-chloro-N-[1-[4-(difluoromethoxy)phenyl]propyl]-6-methyl-4-pyrimidinamine
CAS RN [130339-07-0] Development codes UBF-002 (Ube)

PHYSICAL CHEMISTRY
Mol. wt. 327.8 M.f. C15H16ClF2N3O Form Pale yellow crystals. M.p. 46.9-48.7 °C V.p. 3.21 ´ 10-1 mPa (25 °C) KOW logP = 4.17 (pH 6.86) Henry 3.19 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 0.490 (25 °C) Solubility In water 33 mg/l (25 °C). Readily soluble in most organic solvents. Stability Stable to hydrolysis at pH 4-9. pKa 4.5, weak base F.p. 201.3 °C

COMMERCIALISATION
History Invented by Ube Industries, Ltd., and developed in co-operation with Nissan Chemical Industries, Ltd. Registered for ornamental use in Japan in 1997. Acquired by SDS Biotech KK in 2003. Patents US 5141941; EP 0370704 Manufacturers SDS Biotech KK

APPLICATIONS
Biochemistry May inhibit complex 1 of respiration. Mode of action Protectant fungicide. Uses For control of powdery mildew and rust on ornamentals. Formulation types EC. Selected products: 'Pyricut' (SDS Biotech KK, Nissan)

MAMMALIAN TOXICOLOGY
Oral LD50 for male rats 448, female rats 534, male mice 468, female mice 387 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Slight skin and eye irritant (rabbits). Slight skin sensitisation (guinea pigs). Inhalation LC50 for male and female rats 0.61 mg/l. Other Negative in Ames, chromosome aberration and mouse micronucleus tests.

ECOTOXICOLOGY
Birds LD50 for Japanese quail 881, mallard ducks 1979 mg/kg. Fish LC50 (48 h) for rainbow trout 0.025, carp 0.098 mg/l. Daphnia LC50 (3 h) 0.96 mg/l. Bees LD50 (oral) >10 mg/bee; (contact) 29 mg/bee.

ENVIRONMENTAL FATE
Soil/Environment Soil dissipation DT50 (field, Japan) 60-100 d. Aerobic metabolism DT50 4.5 mo; the major metabolite, which barely exceeded 10% at any time, was diflumetorim hydroxylated at the pyrimidine-2 position. Koc 572-1710. Photolytic DT50 (river water) 168 h. See K. Fujii & S. Takamura, Agchem. Japan, 72, 14 (1998).