Iprodione 异菌脲

异菌脲

英文通用名 iprodione
其他名称 Rovral，扑海因
中文别名：扑海因; 1-异丙胺基甲酰基-3-(3,5-二氯苯基)乙内酰脲; 3-(3,5-二氯苯基)-1-异丙基氨基甲酰基乙内酰脲; 3-(3,5-二氯苯基)-N-异丙基-2,4-二氧代咪唑啉-1-羧酰胺
CAS号 36734-19-7
EINECS号 253-178-9
分子式 C13H13Cl2N3O3
分子量 330.17
InChI InChI=1/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)
熔点 130-136℃
水融性 0.0013 g/100 mL
物化性质 熔点 130-136°C
水溶性 0.0013 g/100 mL
用途 属广谱保护性杀菌剂
安全术语 S36/37:;
S60:;
S61:;
风险术语 R40:;
R50/53:;

理化性质和制剂：原药白色结晶，无味，难溶于水，易溶于丙酮、二甲基甲酰胺等有机溶剂，遇碱分解，无吸湿性，无腐蚀性。常温下贮存稳定。常见制剂有50%扑海因悬浮剂等。
毒性：属低毒杀菌剂。大鼠急性经口LD50为3500毫克/千克，小鼠为4000毫克/千克；大鼠经皮LD50>1000毫克/千克。对北美鹌鹑急性经口LD50为930毫克/千克，对野鸭子为10400毫克/千克。对蜜蜂LD50>400微克/头(触杀)。
作用特点：异菌脲是二甲酰亚胺类高效广谱、触杀型杀菌剂。适用于防治多种果树、蔬菜、瓜果类等作物早期落叶病、灰霉病、早疫病等病害。其他名称：扑海因、桑迪恩。制剂：50%可湿性粉剂、50%悬浮剂、25%、5%扑油悬浮剂。毒性：按中国农药毒性分级标准，异菌脲属低毒杀菌剂。作用机制：异菌脲能抑制蛋白激酶，控制许多细胞功能的细胞内信号，包括碳水化合物结合进入真菌细胞组分的干扰作用。因此，它即可抑制真菌孢子的萌发及产生，也可抑制菌丝生长。即对病原菌生活史中的各发育阶段均有影响。

产品特点

1.适用于瓜类、番茄、辣椒、茄子、园林花卉、草坪等多种蔬菜及观赏植物等。主要防治对象为由葡萄孢菌、珍珠菌、交链孢菌、核盘菌等引起的病害。如灰霉病、早疫病、黑斑病、菌核病等。
2.异菌脲是一种广谱触杀型保护性杀菌剂，同时具有一定的治疗作用，也可通过根部吸收起内吸作用。可有效防治对苯并咪唑类内吸杀菌剂有抗性的真菌。

使用方法

1.防治草莓灰霉病：于草莓发病初期开始喷药，每隔8天施药1次，收获前2～3星期停止施药。每次每亩用50%异菌脲悬浮剂或可湿性粉剂100毫升(克)，兑水喷雾。
2.防治果花腐病、灰星病、灰霉病：花腐病于果树始花期和盛花期各喷1次药。灰星病于果实收获前3～4星期和1～2星期各喷1次。灰霉病则于收获前视病情施1～2次药。每次每亩用50%异菌脲悬浮剂或可湿性粉剂66～100毫升(克)，兑水喷雾。
3.防治番茄灰霉病、早疫病、菌核病和黄瓜灰霉病、菌核病：发病初期开始喷药，全生育期施药1～3次，施药间隔期7～10天。每次每亩用50%异菌脲悬浮剂或可湿性粉剂50～100毫升(克)，兑水喷雾。
4.防治大白菜、菜豆、甘蓝、西瓜、甜瓜、芦笋等蔬菜灰霉病、菌核病、黑斑病、斑点病、茎枯病等：发病初期开始施药，施药间隔期，叶部病害7～10天，根茎部病害10～15天，每次每亩用50%异菌脲悬浮剂或可湿性粉剂66～100毫升(克)，兑水喷雾。
5.防治观赏作物叶斑病、灰霉病、菌核病、根腐病：可于发病初期开始喷药，施药间隔7～14天，每次每亩用50%异菌脲悬浮剂或可湿性粉剂75.4～100毫升(克)，兑水喷雾，也可采用浸泡插条的方法，即在50%异菌脲悬浮剂或可湿性粉剂125～500倍液中浸泡15分钟。
6.苹果轮斑病、褐斑病及落叶病的防治，春梢生长期初发病时，喷50%异菌脲可湿性粉剂1000-1500倍液，以后每隔10-15天喷1次。
7.花生冠腐病 每100公斤种子用50%异菌脲可湿性粉剂100-300克拌种。
8.玉米小斑病的防治，在玉米小斑病初发时开始喷药，50%异菌脲可湿性粉剂200-400克兑水喷雾，隔2周再喷1次。
9.防治黄瓜灰霉病和黄瓜菌核病，在发病初期每亩用50%异菌脲可湿性粉剂75－100克，分别兑水50公斤和80~100公斤喷雾。间隔7－10天喷洒1次，共喷1一3次。
10.防治蚕豆赤斑病、韭菜灰霉病，亩用50%可湿性粉剂50克，兑水50-75公斤喷雾，7-10天喷1次，连喷2－3次。
11.防治莴苣灰霉病，用50%异菌脲可湿性粉剂25克，兑水50公斤，于发病初期每隔10－15天喷1次，连喷2－3次。
12.防治温室葫芦科蔬菜、胡椒、茄子等的灰霉病、早疫病、斑点病：发病初期开始施药，每隔7天施1次药，连续施2-3次，每次每亩用50%异菌脲悬浮剂或可湿性粉剂50-100毫升(克)，对水喷雾。[1]

注意事项

1.不能与腐霉利(速克灵)、乙烯菌核利(农利灵)等作用方式相同的杀菌剂混用或轮用。
2.不能与强碱性或强酸性的药剂混用。
3.为预防抗性菌株的产生，作物全生育期异菌脲的施用次数要控制在3次以内，在病害发生初期和高峰前使用，可获得最佳效果。

iprodione
Fungicide
FRAC 2, F1; dicarboximide

NOMENCLATURE
Common name iprodione (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide
Chemical Abstracts name 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide
Other names glycophene* (rejected common name proposal) CAS RN [36734-19-7] EEC no. 253-178-9 Development codes 26 019 RP (Rhône-Poulenc)

PHYSICAL CHEMISTRY
Composition Tech. is ³96% pure. Mol. wt. 330.2 M.f. C13H13Cl2N3O3 Form White, odourless, non-hygroscopic crystals or powder. M.p. 134 ºC; (tech., 128-128.5 ºC) V.p. 5 ´ 10-4 mPa (25 ºC) KOW logP = 3.0 (pH 3 and 5) S.g./density 1.00 (20 ºC); (tech., 1.434-1.435) Solubility In water 13 mg/l (20 ºC). In n-octanol 10, acetonitrile 168, toluene 150, ethyl acetate 225, acetone 342, dichloromethane 450, hexane 0.59 (all in g/l, 20 ºC). Stability Relatively stable in acid media, but decomposed in alkaline media. DT50 1-7 d (pH 7), <1 h (pH 9). Aqueous solutions are degraded by u.v. light, but are relatively stable in simulated sunlight.

COMMERCIALISATION
History Fungicide reported by L. Lacroix et al. (Phytiatr. Phytopharm., 1974, 23, 165). Introduced by Rhône-Poulenc Agrochimie (now Bayer CropScience). Some rights, primarily in Europe, acquired by BASF AG in 2003. Patents GB 1312536; US 3755350; FR 2120222 Manufacturers BASF; Sannong; Sharda; Sinon; Sundat

APPLICATIONS
Mode of action Contact fungicide with protective and curative action. Inhibits germination of spores and growth of fungal mycelium. Uses Control of Botrytis, Monilia, Sclerotinia, Alternaria, Corticium, Fusarium, Helminthosporium, Phoma, Rhizoctonia, Typhula spp., etc. Used mainly on sunflowers, cereals, fruit trees, berry fruit, oilseed rape, rice, cotton, vegetables, and vines as a foliar spray, at 0.5-1.0 kg/ha, and on turf, at 3-12 kg/ha. Can also be used as a post-harvest dip, as a seed treatment, or as a dip or spray at planting. Formulation types DP; EC; FS; SC; SU; WG; WP. Selected products: 'Amazzones' (Rocca); 'Botrix' (Agrimix); 'Kidan' (Bayer CropScience, BASF); 'Rover' (Vapco); 'Rovral' (Bayer CropScience, BASF); 'Verisan' (Bayer CropScience, BASF); 'Viroval' (Vipesco)

OTHER PRODUCTS
'Dirac' (Bayer CropScience, BASF) mixtures: 'Compass' (+ thiophanate-methyl) (BASF); 'Snooker' (+ thiophanate-methyl) (BASF); 'But' (+ bromuconazole) (Bayer CropScience, BASF); 'Calidan' (+ carbendazim) (Bayer CropScience, BASF); 'Diva' (+ chlorothalonil) (Bayer CropScience, BASF); 'Pacha' (+ carbendazim) (Philagro); 'Premis Or' (+ triticonazole+ anthraquinone) (Bayer CropScience, BASF); 'Vitesse' (+ carbendazim) (Bayer CropScience, BASF) Discontinued products mixtures: 'Chipco' * (+ fosetyl-aluminium) (Aventis)

ANALYSIS
Product analysis by rplc or glc (CIPAC Handbook, 1995, G, 98-104; L. Lacroix et al., Anal. Methods Pestic. Plant Growth Regul., 1980, 11, 247). Residues determined by glc with ECD (idem, ibid.; Man. Pestic. Residue Anal., 1987, I, 6, S8, S19; Anal. Methods Residues Pestic., 1988, Part I, M1, M12).

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 74, 76 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats and mice >2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >5.16 mg/l air. NOEL (2 y) for rats 150 mg/kg diet; (1 y) for dogs 18 mg/kg b.w. ADI (JMPR) 0.06 mg/kg b.w. [1995]. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification R40| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000, mallard ducks >10 400 mg/kg. Fish LC50 (96 h) for rainbow trout 4.1, bluegill sunfish 3.7 mg/l. Daphnia LC50 (48 h) 0.25 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 1.9 mg/l. Bees Contact LD50 >0.4 mg/bee. Worms LC50 for earthworms >1000 mg/kg soil. Other beneficial spp. Harmless.

ENVIRONMENTAL FATE
Animals In rats, ruminants and birds, iprodione is rapidly eliminated. It also undergoes extensive metabolism, by hydrolysis and rearrangement reactions. Plants Metabolism studies in cereals, fruit, leafy and oily crops showed that iprodione is the dominant component of the total residue resulting from foliar application. Soil/Environment Rapidly metabolised in soil, with formation of CO2. DT50 (lab.) 20-80 d; (field) 20-160 d. Koc 373 to 1551. Rate of degradation increases with successive treatments, hence accumulation does not occur.