Metconazole 叶菌唑

叶菌唑

中文通用名称： 叶菌唑
英文通用名称： metconazole （BSI，ISO）
商品名称： Caramba
化学名称： (1RS,5RS;1RS,5SR)-5-(4-氯苄基)-2,2-二甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

CA主题索引名及CAS登录号：
5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopen-tanol
[125116-23-6]
化学结构类型： 三唑类

理化性质：
纯品(cis-和trans-混合物)为白色、无味结晶体；熔点110~113℃(原药：100.0~108.4℃)；沸点：大约285℃；密度1.307(20℃)；蒸气压1.23×10-5Pa(20℃)；分配系数(20℃)LogP＝3.85；溶解度(20℃，mg/l) 水15，甲醇 235；丙酮238.9；有很好的热稳定性和水解稳定性。

毒性：
大鼠急性经口LD50：>661mg/kg； 大鼠急性经皮LD50：>2000mg/kg；大鼠吸入LC50(4小时)：>1.4mg/l；本品对兔皮肤无刺激，对兔眼睛有轻微刺激。Ames试验呈阴性。鹌鹑147急性经口LD50：790mg/kg； 虹鳟LC50(96小时)：2.2~4.0mg/l，鲤鱼3.99mg/l；对蚯蚓无毒；水蚤 LC50(48小时)：3.6~4.4mg/l。

制剂
60SL、其它有EC、SC

作用机理： 作用机理与特点麦角甾醇生物合成中C-14脱甲基化酶抑制剂。虽然作用机理与其他三唑类杀菌剂一样，但活性谱则差别较大。两种异构体都有杀菌活性，但顺式活性高于反式。叶菌唑的杀真菌谱非常广泛，且活性极佳。叶菌唑田间施用对谷类作物壳针孢、镰孢霉和柄锈菌植病有卓越效果。叶菌唑同传统杀茵剂相比，剂量极低而防治谷类植病范围却很广。

适宜作物： 禾谷类作物等。
对作物安全性： 推荐剂量下对作物安全、无药害。
防治对象： 适宜作物与安全性小麦、大麦、燕麦、黑麦、小黑麦等作物。叶菌唑对非靶标生物低毒，用量低而杀菌活性高，环境前景佳。
防治对象叶菌唑是一种新的、广谱内吸性杀菌剂。主要用于防治小麦壳针孢、穗镰刀菌、叶锈病、条锈病、白粉病、颖枯病；大麦矮形锈病、白粉病、喙孢属；黑麦喙孢属、叶锈病；燕麦冠锈病，一小黑麦（小麦与黑麦杂交）叶锈病、壳针孢。对壳针孢属和锈病活性优异。兼具优良的保护及治疗作用。对小麦的颖枯病特别有效，预防、治疗效果俱佳。

应用： 叶菌唑是一种新的、广谱内吸性杀菌剂。兼具优良的保护及治疗作用。既可茎叶处理又可作种子处理。茎叶处理：30~90克有效成分/公顷，持效期5~6周。 种子处理：2.5~7.5克有效成分/100公斤种子。

合成方法：
以二甲基环戊酮为起始原料，与碳酸二甲酯反应，经烷基化、脱羧；再与碘代三甲基亚砜 （由碘甲烷与二甲基亚砜制得） 生成取代的环氧丙烷；最后与三唑反应，处理即得叶菌唑。反应式如下：

主要原料与中间体： 取代的环戊酮、碳酸二甲酯、对氯苄氯、三唑
分析方法：GC或HPLC
开发公司： 由日本吴羽化学公司发现，现有美国氰胺公司开发。

metconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name metconazole (BSI, pa ISO (for cis:trans mixture))
IUPAC name (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
Chemical Abstracts name 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
CAS RN [125116-23-6] unstated stereochemistry Development codes KNF-S-474 (Kureha); WL 148271 (Shell); AC 900,768 (Cyanamid); BAS 555 F (BASF)

PHYSICAL CHEMISTRY
Composition The common name metconazole applies to the (1RS,5RS;1RS,5SR)- isomers. Tech. material is a mixture of cis- and trans- isomers, predominantly cis-, (1RS,5SR) (hydroxy and benzyl groups on the same side of the cyclopentyl ring); both isomers are fungicidally active. Mol. wt. 319.8 M.f. C17H22ClN3O Form Off-white, odourless powder. M.p. 100.0-108.4 °C V.p. 2.1 ´ 10-5 mPa (20 ºC) KOW logP = 3.85 (20 ºC) Henry 2.21 ´ 10-7 Pa m3 mol-1 S.g./density 1.14 Solubility In water 30.4 mg/l (20 ºC). In methanol 403, acetone 363 (both mg/ml, 20 ºC). Stability Good thermal and hydrolytic stability.

COMMERCIALISATION
History Discovered by Kureha Chemical Industry Co., Ltd in 1986. Reported by A. J. Sampson et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 419). Developed jointly with Shell Group (later American Cyanamid Co., then BASF AG); introduced by Cyanamid Agro in France in 1994. Patents EP 267778 Manufacturers Kureha

APPLICATIONS
Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor. Both isomers are active. Mode of action Applied post-emergence, exhibits penetrant, local and acropetal systemicity. Uses Control of a wide range of foliar diseases on cereals, at 90 g/ha, and on other crops. It is particularly effective against Fusarium, Septoria and rust diseases on cereals. Phytotoxicity Exhibits some plant growth regulant activity such as thickening of leaves, stunting and darkening of leaf colour. Formulation types SL. Selected products: 'Caramba' (BASF)

OTHER PRODUCTS
'Cinch Pro' (BASF); 'Cinch' (BASF); 'Juventus 90' (BASF); 'Sirocco' (BASF); 'Sunorg Pro' (BASF); 'Sunorg' (BASF)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 660 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not irritant to skin; slight irritant to eyes (rabbits). Not a skin sensitiser. Inhalation LC50 (4 h) for rats >5.6 mg/l. NOEL (104 w) for rats 4.8 mg/kg b.w. daily; (52 w) for dogs 11.1 mg/kg b.w. daily; (90 d) for mice 5.5, rats 6.8, dogs 2.5 mg/kg b.w. daily. ADI 0.048 mg/kg b.w. Other Negative in the Ames test. Toxicity class WHO (a.i.) III

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 787 mg/kg. Acute dietary LC50 for mallard ducks >5200 mg/kg. Fish LC50 (96 h) for rainbow trout 2.2, fathead minnow 3.9, common carp 3.99 mg/l. Daphnia LC50 (48 h) 4.2 mg/l. Algae EC50 (72 h) for Selenastrum capricornutum 1.7 mg/l. Bees Practically non-toxic to bees; oral LD50 (24 h) 90 mg/bee. Worms Practically non-toxic to earthworms.

ENVIRONMENTAL FATE
Soil/Environment Koc 726-1718 (five soil types). No pH dependence.