Zoxamide 苯酰菌胺

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农药杀真菌剂——苯酰菌胺——

中文通用名称 苯酰菌胺

英文通用名称 zoxamide

商 品 名 称 Zoxium(单剂);Gay-el、Electis(苯酰菌胺与代森锰锌的混剂)

化 学 名 称 (RS)-3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)对甲基苯甲酰胺。

(RS)-3,5-dichloro-N-(3-ehloro-1-ethy-1-methyl-2-oxopropyl)-p-toluamide。

CAS登录号 156052-68-5

理化性质 纯品熔点159.5~160.5℃。蒸气压<1×10-2mPa(45℃)。分配系数KOWlogP=3.76(20℃),在水中的溶解度0.681mg/L(20℃),水中的水解半衰期为15d(pH4和7)、8d(pH9)、水中光解半衰期为7.8d,土壤中半衰期为2~lOd。

毒性 大鼠急性经口LD50>5000mg/kg,大鼠急性经皮LD50>2OOOmg/kg,大鼠急性吸入LC50(4h)>5.3mg/L。对兔皮肤和眼睛均无刺激作用,对豚鼠皮肤有刺激性。诱变试验(4种试验):阴性。致畸试验(兔,大鼠):无致畸性。繁殖试验(兔,大鼠):无副作用。慢性毒性/致癌试验:无致癌性。野鸭和山齿鹑急性经口LC50>5250mg/kg。鳟鱼急性LC50(96h)160ug/L。蜜蜂LD50>100ug/只(经口和接触);蚯蚓LC50(14d)>1070mg/kg土壤。

制剂
24%悬浮剂、80%WP。

作用机理与特点
苯酰菌胺的作用机制在卵菌纲杀菌剂中是很独特的。它通过微管蛋白β-亚基的结合和微管细胞骨架的破裂来抑制菌核分裂。苯酰菌胺不影响游动孢子的游动、孢囊形成或萌发。伴随着菌核分裂的第一个循环,芽管的伸长受到抑制,从而阻止病菌穿透寄主植物。实验室中用冬瓜疫霉病和马铃薯晚疫病试图产生抗性突变体没有成功,可见田间快速产生抗性的危险性不大。实验室分离出抗苯甲酰胺类和抗二甲基吗啉类的菌种。试验结果表明苯酰菌胺与之无交互抗性。

适宜作物与安全性
马铃薯、葡萄、黄瓜、辣椒、菠菜等。在推荐剂量下对多种作物都很安全,对哺乳动物低毒,对环境安全。

防治对象
主要用于防治卵菌纲病害如马铃薯和番茄晚疫病,黄瓜霜霉病和葡萄霜霉病等;对葡萄霜霉病有特效。离体试验表明苯酰菌胺对其他真菌病原体也有一定活性,推测对甘薯灰霉病,莴苣盘梗霉,花生褐斑病。白粉病等有一定的活性。

应用技术
苯酰菌胺是一种具有高效的保护性杀菌剂,具有长的持效期和很好的耐雨水冲刷性能;因此应在发病前使用,且掌握好用药间隔时间,通常为7~10d。

使用方法
主要用于茎叶处理,使用剂量为100~250g(a.i.)/hm2。实际应用时常和代森锰锌以及其他杀菌剂混配使用,不仅扩大杀菌谱,而且可提高药效。

其 他
苯酰菌胺(试验代号RH-7281)是由罗门哈斯公司(现为陶氏农业科学公司)开发的酰胺类杀菌剂


 

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zoxamide
Fungicide
FRAC 22, B3; benzamide (F)

  zoxamide

NOMENCLATURE
Common name zoxamide (BSI, pa ISO)
IUPAC name (RS)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-p-toluamide
Chemical Abstracts name 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide
CAS RN [156052-68-5] Development codes RH-7281; RH-117281 (both Rohm & Haas)

PHYSICAL CHEMISTRY
Mol. wt. 336.6 M.f. C14H16Cl3NO2 Form Fine, white powder, with a liquorice-like odour. M.p. 159.5-161 °C V.p. <1 ´ 10-2 mPa (up to 45 °C) KOW logP = 3.76 (20 °C) S.g./density 1.38 (20 °C) Solubility In water 0.681 mg/l (20 °C). In acetone 55.7 g/l (25 °C). Stability Aqueous hydrolysis DT50 c. 15 d (pH 4 and 7), c. 8 d (pH 9). Aqueous photolysis DT50 7.8 d.

COMMERCIALISATION
History Reported by A. R. Egan et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 335). Developed by Rohm & Haas Co. (now Dow AgroSciences), first registered in USA and launched in Europe in 2001. Patents US 5304572 Manufacturers Dow AgroSciences

APPLICATIONS
Biochemistry Prevents nuclear division by binding to the b-subunit of tubulin and disruption of the microtubule cytoskeleton. Mode of action Preventative fungicide with rainfast and residual properties. Uses Applied at 120-200 g/ha, provides control of Oomycete fungi, including Phytophthora infestans, on potatoes (foliar, stem, tuber blight) and tomatoes, Plasmopara viticola on vines and Pseudoperonospora cubensis on cucurbits. Zoxamide is not cross-resistant to current Oomycete fungicides, such as phenylamides, QoI fungicides or cymoxanil. Sold in preformulated mixtures with either mancozeb or cymoxanil. Formulation types WG; WP. Selected products: 'Zoxium' (Dow AgroSciences); mixtures: 'Electis' (+ mancozeb) (Dow AgroSciences); 'Gavel' (+ mancozeb) (Dow AgroSciences); 'Roxam' (+ mancozeb) (Interfarm)

OTHER PRODUCTS
Mixtures: 'Aderio' (+ mancozeb) (Dow AgroSciences); 'Harpon' (+ cymoxanil) (Dow AgroSciences); 'Stimo' (+ mancozeb) (Dow AgroSciences); 'Unikat' (+ mancozeb) (Dow AgroSciences)

ANALYSIS
Product analysis by reverse phase hplc with uv detection. Residues of zoxamide in crops and various environmental matrices are analysed by gc with ECD detection. Details available from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 >2000 mg/kg. Non-irritating to skin; moderate eye irritant (rabbits) in USA, no classification in EU. Is a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5.3 mg/l. NOEL Dietary NOEL (1 y) for dogs 50 mg/kg b.w. daily. ADI 2.6 mg/kg b.w. (proposed) Other Negative in 4 mutagenicity tests, non-teratogenic, no adverse reproductive effects; no oncogenic potential.

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for mallard ducks and bobwhite quail >5250 mg/kg diet. Reproduction NOEL for mallard ducks and bobwhite quail 1000 mg/kg diet. Fish LC50 (96 h) for rainbow trout 160 mg/l; LC50 (96 h) for bluegill sunfish >790, sheepshead minnow >855, zebra fish >730 mg/l (all greater than solubility limit). Life cycle NOEC for fathead minnow 60 mg/l. Daphnia EC50 (48 h) >780 mg/l (solubility limit). Reproduction NOEC (21 d) 39 mg/l. Algae EC50 (120 h, cell density) for Selenastrum capricornutum 19, Scenedesmus subspicatus 11 mg/l; EC50 (120 h, cell density) for Anabaena flos-aquae >860, Navicula pelliculosa >930, Skeletonema costatum >910 mg/l (all greater than solubility limit). Other aquatic spp. EC50 (48 h) for Eastern oyster 703 mg/l; LC50 (96 h) for mysid shrimp 76 mg/l. EC50 (14 d) for Lemna gibba 17 mg/l. Bees LD50 (contact) for honeybees >100 mg/bee. Worms LC50 (14 d) >1070 mg/kg soil; sublethal growth and reproduction NOEC 7 mg/kg natural soil. Other beneficial spp. IOBC classification: Harmless at 0.15 kg/ha (1´ typical rate) to Typhlodromus pyri, Aphidius rhopalosiphi, Amblyseius andersoni, Pardosa sp., Poecilus cupreus, Chrysoperla carnea, Orius insidiosus; slightly harmful at 0.3 kg/ha (2´ typical rate) to Aphidius and Chrysoperla.

ENVIRONMENTAL FATE
Zoxamide is a relatively transient molecule in the environment with low potential for persistence or movement. Animals In metabolism studies faecal excretion was the primary route of elimination. A total of 36 metabolites, including the parent compound, were detected in the urine and faeces; the parent compound was the principal component excreted. Bioconcentration factor in bluegill sunfish 95-136; 50% clearance time 0.4 days. Plants Zoxamide penetrates surface layers of the plant but has limited translocation. Soil/Environment Soil DT50 2-10 d; CO2 is the major metabolite. Koc 1166-1224; low mobility, no leaching potential.