Carpropamid 环丙酰菌胺 环丙酰亚胺

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中文通用名称: 环丙酰菌胺
英文通用名称: carpropamid (ISO建议名)
商品名称: Win、Win Admire(与吡虫啉混用)、 Arcado、 Seed One、Zabara
试验代号: K T U 3616
化学名称: 2,2-二氯-N-[1-(4-氯苯基)乙基]-1-乙基-3-甲基环丙羧酰胺
2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxam-ide
CA主题索引名及CAS登录号: trans-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecar-boxamide
消旋体[104030-54-8];A R对映体[127641-62-7];B R对映体[127640-90-8];

化学结构类型: 酰胺类
理化性质: 纯品为无色粉状固体,原药白色至淡黄色固体;熔点145~149℃(原药);密度1.17(20℃);蒸气压AR 2×10-6Pa (20℃),B R 3×10-6Pa(20℃);分配系数(22℃) AR LogP=4.23, BR LogP=4.28;水中溶解度(mg/l,pH7,20℃):A R 1.7,B R 1.9。
毒性
大鼠(小鼠)急性经口LD50:雄或雌>5000mg/kg; 大鼠(小鼠)急性经皮LD50:雄或雌>2000mg/kg;大鼠急性吸入LC50:雄或雌>5000mg/l。本品对兔眼睛和皮肤无刺激。野鸭急性经口LD50:1979mg/kg; 鱼毒(96小时,mg/l)LC50:鳟 10,鲤鱼 6.9 ;水蚤 LC50(3小时):410mg/l。 Ames试验呈阴性,微核及细胞体外试验呈阴性。

制剂: D P、G R、SC、W S、FS
作用机理: 与现有杀菌剂不同,K T U 3616无杀菌活性,不抑制病原菌菌丝的生长。其具有两种作用方式:抑制黑色素生物合成和在感染病菌后可加速植物抗菌素如momilactone A和sakuranetin的产生,这种抗性机理预示K T U 3616可能对其它病害亦有活性。
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
预防对象: 稻瘟病
应用: KTU 3616主要用于稻田防治稻瘟病。以预防为主,治疗活性较弱,具有内吸活性。在接种后6小时内用K T U 3616处理,则可完全控制稻瘟病的侵害,但超过6小时如8小时后处理,几乎无活性。在育苗箱中应用剂量为400克有效成分/公顷;茎叶处理剂量为75~150克有效成分/公顷;种子处理剂量相当于160克有效成分/公顷。

合成方法:
以丁酸乙酯为起始原料制得中间体取代的环丙酰氯与以对氯苯乙酮为起始原料制备的取代苄胺反应,即得目的物。反应式为:

主要原料与中间体: 对氯苯乙酮 、 丁酸乙酯、乙醛、盐酸羟胺
分析方法: GC或HPLC
开发公司: 日本拜耳公司共同开发。

 

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carpropamid
fungicide
FRAC 16.2, I2; MBI: dehydratase

  Carpropamid

NOMENCLATURE
Common name carpropamid (BSI, pa ISO)
IUPAC name A mixture of (1R,3S)-2,2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide (referred to as AR enantiomer), (1S,3R)-2,2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide (referred to as BR enantiomer), (1S,3R)-2,2-dichloro-N-[(S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, and (1R,3S)-2,2-dichloro-N-[(S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, where the first two cited comprise at least 95% of the total
Chemical Abstracts name A mixture of [1R-[1a(R*),3b]]-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, [1S-[1a(S*),3b]]-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, [1S-[1a(R*),3b]]-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, and [1R-[1a(S*),3b]]-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide
CAS RN [104030-54-8]; AR enantiomer [127641-62-7]; BR enantiomer [127640-90-8] Development codes KTU 3616 (Bayer; Nihon Bayer)

PHYSICAL CHEMISTRY
Composition Diastereoisomeric mixture (A:B c. 1:1; RS c. 95:5); the (1R,3S,1R)- enantiomer is designated AR, the (1S,3R,1R)- enantiomer BR. Mol. wt. 334.7 M.f. C15H18Cl3NO Form Colourless crystals; (tech. is a white to yellowish powder). M.p. AR: 161.7 °C; BR: 157.6 °C V.p. AR: 2 ´ 10-3 mPa; BR: 3 ´ 10-3 mPa (both 20 °C, gas saturation method OECD 104) KOW AR: logP = 4.23, BR: logP = 4.28 (both 22 ºC) Henry AR: 4 ´ 10-4 Pa m3 mol-1, BR: 5 ´ 10-4 Pa m3 mol-1 (both 20 °C, calc.) S.g./density 1.17 (20 °C) Solubility In water 1.7 (AR), 1.9 (BR) (both in mg/l, pH 7, 20 ºC).

COMMERCIALISATION
History Discovered and developed jointly by Nihon Bayer Agrochem. K.K. and Bayer AG. Reported by T. Hattori et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1994, 2,517). Introduced in Korea in 1996 as a seed treatment and in 1998 as a spray. Introduced in Colombia and Japan in 1997, as a spray application and a seedling-box treatment, respectively. Patents EP 00341475 Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry In Pyricularia oryzae, carpropamid inhibits melanin biosynthesis, by inhibiting the dehydration reactions from scytalone to 1,3,8-trihydroxynaphthalene and from vermelone to 1,8-dihydroxynaphthalene. Also enhances crop resistance by increasing phytoalexin production following rice blast infection. Mode of action Systemic, protective fungicide. Uses Systemic fungicide with specific action against Pyricularia oryzae; it does not provide curative properties, so protective treatment is essential. Can be used for seed treatment (300-400 g/dt), seedling box treatment (400 g/ha), seedling box drench (200-400 g/ha), and spray (75-150 g/ha). Formulation types FS; GR; SC; WS. Selected products: 'Arcado' (Bayer CropScience); 'Cleaness' (Bayer CropScience); 'Protega' (Bayer CropScience); 'Win' (Bayer CropScience); mixtures: 'Carrena' (+ imidacloprid) (Bayer CropScience); 'Win Admire' (+ imidacloprid) (Bayer CropScience)

OTHER PRODUCTS
'Solazas' (Bayer CropScience); 'Zubard' (Bayer CropScience) mixtures: 'Windantotsu' (+ clothianidin) (Sumitomo Chemical Takeda)

ANALYSIS
Details of methods for product and residue analysis are available from Bayer CropScience.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >5000 mg/kg. No eye or skin irritation (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 for male and female rats >5000 mg/m3 (dust). NOEL (2 y) for rats and mice 400 mg/kg diet; (1 y) for dogs 200 mg/kg diet. ADI 0.03 mg/kg b.w. (Bayer proposed; Colombia, Korea); 0.014 mg/kg b.w. (Japan). Other No mutagenic effects in in vitro or in vivo tests. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds LD50 for Japanese quail >2000 mg/kg. Fish LC50 (48/72 h) for carp 5.6 mg/l; LC50 (96 h) for rainbow trout 10 mg/l. Daphnia LC50 (3 h) 410 mg/l. Algae ErC50 (72 h) for Scenedesmus subspicatus >2 mg/l. Other aquatic spp. LC50 (3 h) for water flea (Moina macrocopa) >20 mg/l. Worms LC50 for Eisenia foetida >1000 mg/kg dry substrate.

ENVIRONMENTAL FATE
Animals After oral administration of radiolabelled carpropamid to rats, the radioactivity was readily excreted via faeces and urine. Carpropamid was metabolised oxidatively, mainly in the liver. Plants After treatment of rice plants via soil (nursery box application) or nutrient medium, carpropamid was absorbed by the roots and translocated to the shoots. The major residue in rice was carpropamid. Soil/Environment Carpropamid was metabolised oxidatively under paddy soil conditions; CO2 was the major metabolite. In field and laboratory trials, under paddy conditions, the calculated half-lives ranged from several weeks to several months, respy. Adsorption/desorption studies with the parent compound indicated that carpropamid can be classified as being of low mobility. Hydrolytically stable in sterile aqueous buffer solutions, photodegraded in natural water; degradation was significantly faster in natural water than in sterile water.