Imibenconazole 亚胺唑

亚胺唑

CAS号: 86598-92-7
英文名称: imibenconazole
化学名称：4-氯苄基-N-2,4-二氯苯基-2-(1H-1,2,4-三唑-1-基)硫代乙酰胺酯；2,4-triazole-1-ethanamidothioicacid,n-(2,4-dichlorophenyl)-1h-(4-chloroph;
其他名称：霉能灵;酰胺唑;HF 8505 (制剂)
分子式：C17H13Cl3N4S
分子量：411.74

理化性质：纯品为白色晶体。m.p.89.5～90℃，蒸气压0.85×10-4Pa(25℃)。溶解度：丙酮 1063g/L，苯580g/L，二甲苯250g/L，甲醇120g/L，水1.79g/L。在弱碱性条件下稳定，对光稳定，在强酸、强碱时不稳定。

毒性：雄性大鼠急性经口LD502800mg/kg，雌性为3000mg/kg；小鼠（雄、雌）急性经口LD50>5000mg/kg。大鼠（雄、雌）急性经皮LD50>2000mg/kg。对家兔眼睛有轻度刺激作用。对豚鼠皮肤有轻度刺激作用，对家兔皮肤无致敏作用。鲤鱼LC501.02mg/L (48h)，水蚤LC50102mg/L (6h)。蜜蜂经口LD50>25μg/只。

作用特点及用途：新颖的三唑类杀菌剂。杀菌谱广，主要作用机理是破坏和阻止病菌的纫胞膜重要组成成分麦角甾醇的生物合成，从而破坏细胞膜的形成，导致病菌死亡。具有内吸性并耐雨，兼有治疗和预防活性。用于防治苹果黑星病、锈病、白粉病、煤点病、煤斑病，梨黑星病、锈病，桃疮痂病，以及葡萄、桔橘、西瓜、花生、茶、烟草病害。尤其对柑橘疮痂病、葡萄黑痘病、梨黑星病具有显著的防治效果。对藻菌真菌无效。以2.5～7.5g（a.i.）／hL能有效防治苹果黑星病；7.5g（a.i.）／hL能有效防治葡萄白粉病；以15g（a.i.）／l00kg处理小麦种子，能防治小麦网腥黑穗菌；在120g／l00kg种子剂量下对作物仍无药害。每亩喷药液量一般为100～300L，可视作物大小而定，以喷至作物叶片湿透为止。使用方法亚胺唑推荐使用剂量为60～150g（a.i.）／hm2。

剂型：5％可湿性粉剂，15％可湿性粉剂等。

生产方法 ：1-（1，2，4-三唑-1-基乙酰氧基-2'，4'-二氯苯基亚氨基）-1，2，4-三唑与对氯苄硫醇在甲基异丁酮中回流反应5h，反应毕冷却后加水和苯，分离有机层，加1mol/L NaOH，水洗，无水硫酸钠干燥，减压脱溶，即得亚胺唑。

生产情况：先正达公司、日本北兴化学工业株式会社生产。国内未见生产报道。

imibenconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name imibenconazole (BSI, draft E-ISO)
IUPAC name S-(4-chlorobenzyl) N-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)acetimidothioate
Chemical Abstracts name (4-chlorophenyl)methyl N-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanimidothioate
CAS RN [86598-92-7] unstated stereochemistry Development codes HF-6305 (tech.); HF-8505 (formulation)

PHYSICAL CHEMISTRY
Mol. wt. 411.7 M.f. C17H13Cl3N4S Form Pale yellowish crystals. M.p. 89.5-90 ºC V.p. 8.5 ´ 10-5 mPa (25 ºC) KOW logP = 4.94 Solubility In water 1.7 mg/l (20 ºC). In acetone 1063, benzene 580, xylene 250, methanol 120 (all in g/l, 25 ºC). Stability Stable in weak alkali; unstable in acid and in strong alkali; DT50 <1 d (pH 1), 6 d (pH 5), 88 d (pH 7), 92 d (pH 9), <1 d (pH 13) (25 °C).

COMMERCIALISATION
History Fungicide reported by H. Ohyama et al. (Abstr. 9th Annu. Meeting Pestic. Sci. Soc. Jpn., 1984, p. 120; Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 2, 519). Introduced by Hokko Chemical Industry Co., Ltd. and first marketed in 1994. Patents JP 85026391; US 4512989; GB 2109371 Manufacturers Hokko

APPLICATIONS
Biochemistry Ergosterol biosynthesis inhibition (steroid demethylation inhibitor); at higher doses (³10 ppm), it is physically incorporated into the cell membrane and causes direct physical destruction of the cell (Y. Ogawa, Agchem. Japan,67, 20 (1995)). Mode of action Curative and preventative systemic foliar fungicide. Inhibits growth of both the germ tube and mycelium. Uses Effective against a broad range of diseases affecting fruit, turf, vegetables and ornamentals. Controls Venturia inaequalis, Podosphaera leucotricha, Alternaria mali, Gymnosporangium yamadae (rust), Gloeodes pomigena (sooty blotch) and Zygophiala spp. (fly speck) in apples, at 100-150 g/ha; Venturia nashicola and Gymnosporangium asiaticum in pears, at 75-100 g/ha; Cladosporium carpophilum and Monilinia fructicola in peaches; M. fructicola in apricots; C. carpophilum in Japanese apricots; Elsino?ampelina (anthracnose), Pestalotia spp. and Uncinula necator in grapes (100-150 g/ha); Elsino?fawcettii in citrus. Other uses are in turf, at 67-100 g/ha, against Sclerotinia homoeocarpa, Cochliobolus spp., Curvularia geniculata and Puccinia zoisiae; in tea, at 150 g/ha, against Colletotrichum theae-sinensis, Exobasidium vexans and Pseudocercospora theae; in melon and water melon, against Sphaerotheca fuliginea; in peanut, against Mycosphaerella arachidis; in roses, at 100-200 g/ha, against Diplocarpon rosae, Sphaerotheca pannosa; in chrysanthemums against Puccinia horiana. Formulation types EC; WG; WP. Compatibility Incompatible with pesticides which are strongly acidic. Selected products: 'Manage' (Hokko)

OTHER PRODUCTS
'Hwaksiran' (Dong Bang)

ANALYSIS
Product analysis is by hplc. Residue analysis is by glc with NPD.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 2800, female rats 3000, male and female mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Slight irritant to eyes; non-irritant to skin (rabbits). Slight skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats >1020 mg/m3. NOEL (2 y) for rats 100 mg/kg diet. ADI 0.0085 mg/kg. Other Non-mutagenic. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. Fish LC50 (96 h) for bluegill sunfish 1.0, rainbow trout 0.67, carp 0.84 mg/l. Daphnia LC50 (6 h) >100 mg/l. Algae EC50 for algae >1000 mg/l. Bees LD50 (oral) >125 mg/bee; (contact) >200 mg/bee. Worms LC50 for earthworms >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals Imibenconazole orally administered to rats is rapidly metabolised and eliminated. The major metabolite is 2',4'-dichloro-(1H-1,2,4-triazol-1-yl)acetanilide. Plants Imibenconazole applied to grapes and apples is degraded or metabolised rapidly. The main metabolite is 2',4'-dichloro-(1H-1,2,4-triazol-1-yl)acetanilide. Soil/Environment Rapidly degrades in soil: DT50 (lab.) 4-20 d, (field) 1-28 d. Koc 2813-23 391.