Ipconazole 种菌唑

中文通用名称： 种菌唑
英文通用名称： ipconazole （BSI，ISO）
商品名称： Techlead
试验代号： KNF-317
化学名称： (1RS,2SR,5RS;1RS,2SR,5SR)-2-(4-氯苄基)-5-异丙基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇
(1RS,2SR,5RS;1RS,2SR,5SR)-2-(4-chlorobenzyl)-5-isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

CA主题索引名及CAS登录号：
2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cy-clopentanol
[125225-28-7]

化学结构类型： 三唑类
理化性质：
纯品为无色结晶体；熔点88~90℃；密度1.326~1.369(20℃)；蒸气压(25℃)：3.58×10-6Pa(1RS,2SR,5RS)，6.99×10-6Pa（1RS,2SR,5SR)；分配系数(20℃)LogP=4.21；溶解度(20℃)水6.93mg/l。

毒性： 大鼠急性经口L D50：1338mg/kg； 大鼠急性经皮L D50：>2000mg/kg；本品对兔眼睛和皮肤无刺激。鲤鱼L C50(48小时)：2.5mg/l。
作用机理： 甾醇生物合成中C-14脱甲基化酶抑制剂。
应用： 种菌唑是一种内吸性杀菌剂。1RS,2SR,5RS和1RS,2SR,5SR均有活性，主要用于水稻种子处理。

合成方法： 合成方法与叶菌唑相似。
开发公司： 由日本吴羽化学公司开发

ipconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name ipconazole (BSI, pa E-ISO)
IUPAC name (1RS,2SR,5RS;1RS,2SR,5SR)-2-(4-chlorobenzyl)-5-isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
Chemical Abstracts name 2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
CAS RN [125225-28-7] unstated stereochemistry Development codes KNF-317 (Kureha)

PHYSICAL CHEMISTRY
Composition The common name ipconazole refers to a mixture of the (1RS,2SR,5RS) isomer pair (I) (hydroxy, benzyl and isopropyl groups on the same side of the cyclopentyl ring) and the (1RS,2SR,5SR) isomer pair (II). Mol. wt. 333.9 M.f. C18H24ClN3O Form Colourless crystals. M.p. 88-90 ºC V.p. 3.58 ´ 10-3 mPa (25 ºC) (isomer pair I); 6.99 ´ 10-3 mPa (25 ºC) (isomer pair II) KOW logP = 4.21 (25 ºC) Solubility In water 6.93 mg/l (20 ºC). Stability Good thermal and hydrolytic stability.

COMMERCIALISATION
Patents EP 0267778; US 4938792 Manufacturers Kureha

APPLICATIONS
Biochemistry Inhibitor of ergosterol biosynthesis. Uses Control of a wide range of seed diseases in rice and other crops. It is particularly effective against Gibberella fujikuroi ('Bakanae' disease), Cochliobolus miyabeanus (Helminthosporium leaf spot) and Pyricularia oryzae (blast) on rice. The component isomer pairs are of equal activity. Formulation types EC; SC. Selected products: 'Techlead' (Kureha); mixtures: 'Befran-Seed' (+ iminoctadine triacetate) (Kureha, Dainippon); 'Techlead-C' (+ copper hydroxide) (Kureha, Kumiai)

OTHER PRODUCTS
'Vortex' (Gustafson)

ANALYSIS
Product analysis by hplc or glc.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 1338 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not irritating to skin; slightly irritant to eyes (rabbits). Not a skin sensitiser.

ECOTOXICOLOGY
Fish LC50 (48 h) for carp 2.5 mg/l. Other aquatic spp. LC50 (3 h) for Moina macrocopa >40 mg/l.

ENVIRONMENTAL FATE
Animals Metabolites in the rat are 2-(4-chlorobenzyl)-5-(1-hydroxy-1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, 2-(4-chlorobenzyl)-5-(2-hydroxy-1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol and 1,2,4-triazole. Plants In rice, metabolites are 2-(4-chlorobenzyl)-5-(1-hydroxy-1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, 2-(4-chlorobenzyl)-5-(2-hydroxy-1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol and 2-[1-(4-chlorophenyl)hydroxymethyl]-5-isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol.