Chlorothalonil 百菌清

百菌清

百菌清是广谱、保护性杀菌剂。作用机理是能与真菌细胞中的三磷酸甘油醛脱氢酶发生作用，与该酶中含有半胱氨酸的蛋白质相结全，从而破坏该酶活性，使真菌细胞的新陈代谢受破坏而失去生命力。百菌清没有内吸传导作用，但喷到植物体上之后，能在体表上有良好的黏着性，不易被雨水冲刷掉，因此药效期较长。

简介
英文通用名 chlorothalonil 百菌清的结构式

化学名称：2，4，5，6-四氯-1，3-二氰基苯
其他名称 打克尼尔，Daconil-2787，大克灵，桑瓦特，克劳优，Dacotech 百菌清

分子式：C8N2Cl4
CAS No. ：1897-45-6
相对分子质量：265.91（按1997年国际相对原子质量计）
熔点：250℃～251℃
沸点：350℃
溶解度（g/L,25℃）：水中6×10^-4，二甲苯中80，丙酮2，环已酮、二甲基甲酰胺中30，煤油中≤10 稳定性：在常温贮存条件下稳定，对弱碱或弱酸性介质及对光照稳定，在强碱介质中分解

类型
百菌清为取代苯类广谱性杀真菌剂。商品名称有Daconil 2787,Ter mil,Bravo,Forturf,Funconil,Exotherm等。化学名称是2，4，5，6-四氯-1，3-苯二甲 腈(2,4,5,6-tetra chloro-1,3,-benzene dicarbonifrile)。

特点
属于低毒杀菌剂。纯品为白色无味粉末，沸点350℃，熔点250-251℃，微溶于水，溶于二甲苯和丙酮等有机溶剂。原粉含有效成份96%，外观为浅黄色粉末，稍有刺激臭味，对酸、碱、紫外线稳定。低毒，对兔眼睛和角膜有明显刺激作用，可产生角膜混浊，且不可逆转，但对人眼睛没有此种作用。对少数人皮肤有刺激作用。对鱼毒性大。原粉大鼠急性经口和兔急性经皮LD50均大于10000毫克/公斤，大鼠急性吸入LD50>4.7毫克/升(1h)。对兔眼有强烈刺激作用，以某些人眼有明显的刺激作用。在试验条件下无致畸、致突变作用，对鱼毒性大。

剂型
40%悬浮剂，50%、75%可湿性粉剂，10%油剂，5%、25%颗粒剂，2.5%、10%、30%
、45%烟剂，5%粉剂。

作用与功能
高效、广谱杀菌剂，具有保护作用。对弱酸、弱碱及光热稳定，无腐蚀作用。在植物表面易粘着，耐雨水冲刷，残效期一般7-10天。
适用范围 主要用于果树、蔬菜上锈病、炭疽病、白粉病、霜霉病的防治。
注意事项 该药对皮肤和眼睛有刺激作用，喷药时要注间保护。对梨、柿易发生药害，不宜使用。苹果落花后20天内也不能使用。 高浓度对梨树、柿、桃、梅易产生药害

使用方法
1、防治枣、苹果等果树病害。从初发病时开始，至8月中旬，每10-15天喷洒1次56%嘧菌·百菌清水乳剂800-1000倍液+1000倍“果宝”（果树专用型），可防治多种果树腐烂病、霜霉病、炭疽病、褐斑病和白粉病等。注意与其他杀菌剂交替使用。 百菌清
2、防治黄瓜霜霉病、白粉病等其他果树病害，可于发病初期喷洒700-800倍56%嘧菌·百菌清水乳剂800-1000倍液+1000倍“果宝”（果树专用型），每7-10天1次，连续喷洒2-3次。
3、防治多种蔬菜的疫病、霜霉病、白粉病等病害，于发病初期开始喷洒700-800倍56%嘧菌·百菌清水乳剂800-1000倍液+1000倍“菜宝”（瓜茄果专用型），每7-10天1次，连续喷洒2-3次。
4、蔬菜病害的防治 番茄早疫病、晚疫病及霜霉病，在病害发生初期，每亩用56%嘧菌·百菌清水乳剂800-1000倍液喷雾，每隔7-10天喷1次。
可防治瓜类霜霉病、白粉病、炭疽病、疫病；番茄早疫病、晚疫病、黄瓜灰霉病、叶霉病等。
使用时注意不能与石硫等碱性农药混用。FU和DP最好在叶面有结露的条件下使用，有利发挥药效。
使用浓度：56%嘧菌·百菌清水乳剂800-1000倍液，70%可湿性粉剂600倍液，50%可湿性粉剂400倍液；45%烟剂200—250g/亩；5%粉剂1kg/亩。

注意事项
1.渔业养殖过程中应谨慎使用

chlorothalonil
Fungicide
FRAC M5; multi-site: chloronitrile

NOMENCLATURE
Common name chlorothalonil (BSI, E-ISO, (m) F-ISO, ANSI); TPN (JMAF)
IUPAC name tetrachloroisophthalonitrile
Chemical Abstracts name 2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile
CAS RN [1897-45-6] EEC no. 217-588-1 Development codes DS-2787 (Diamond Shamrock)

PHYSICAL CHEMISTRY
Composition Tech. is c. 97%. Mol. wt. 265.9 M.f. C8Cl4N2 Form Colourless, odourless crystals; (tech. has a slightly pungent odour). M.p. 252.1 °C B.p. 350 ºC/760 mmHg V.p. 0.076 mPa (25 ºC) KOW logP = 2.92 (25 °C) Henry 2.50 ´ 10-2 Pa m3 mol-1 (25 °C) S.g./density 2.0 (20 °C) Solubility In water 0.81 mg/l (25 ºC). In xylene 80, cyclohexanone, dimethylformamide 30, acetone, dimethyl sulfoxide 20, kerosene <10 (all in g/kg, 25 ºC). Stability Thermally stable at ambient temperatures. Stable to u.v. light in aqueous media and in crystalline state. Stable in acidic and moderately alkaline aqueous solutions; slow hydrolysis at pH >9.

COMMERCIALISATION
History Fungicide reported by N. J. Turner et al. (Contrib. Boyce Thompson Inst., 1964, 22, 303). Introduced by the Diamond Alkali Co. (later ISK Biosciences Corp.) and sold to Zeneca Agrochemicals (now Syngenta AG) in 1997. Patents US 3290353; US 3331735 Manufacturers Agrochem; GB Biosciences; Gharda; Gilmore; Isagro; SDS Biotech KK; Sundat

APPLICATIONS
Biochemistry Conjugation with, and depletion of, thiols (particularly glutathione) from germinating fungal cells, leading to disruption of glycolysis and energy production, fungistasis and fungicidal action. Mode of action Non-systemic foliar fungicide with protective action. Uses Control of many fungal diseases in a wide range of crops, including pome fruit, stone fruit, citrus fruit, bush and cane fruit, cranberries, strawberries, pawpaws, bananas, mangoes, coconut palms, oil palms, rubber, pepper, vines, hops, vegetables, cucurbits, tobacco, coffee, tea, rice, soya beans, peanuts, potatoes, sugar beet, cotton, maize, ornamentals, mushrooms, and turf. Application rates for food crops are 1-2.5 kg/ha. Phytotoxicity Russetting is possible with flowering ornamentals, apples, and grapes. Some varieties of flowering ornamentals may be injured. Pittosporum foliage is sensitive. Phytotoxicity may be increased with oils or oil-containing substances. Formulation types SC; WG; WP; Fogging concentrate. Compatibility Not compatible with oils. Selected products: 'Bravo' (Syngenta); 'Daconil' (Syngenta, SDS Biotech KK); 'Banko' (Calliope); 'Bombardier' (Unicrop); 'Chloronil' (Vapco); 'Clortosip' (Sipcam); 'Corrib' (Barclay); 'Equus' (Nations Ag); 'Fungiless' (Sanonda); 'Gilonil' (Gilmore); 'Mycoguard' (Chiltern, Gharda); 'Oranil' (Cequisa); 'Talonil' (Ingeniería Industrial); 'Teren' (Efthymiadis); 'Visclor' (Vischim)

OTHER PRODUCTS
'Countdown L&G' (Syngenta); 'ISK 375' (Syngenta); 'Jupital' (Syngenta); 'Kvach' (Syngenta); 'Nuocide' (Syngenta); 'Ole' (Syngenta); 'Tuffcide' (Syngenta); 'Atlas Cropgard' (Nufarm UK); 'Clortocaffaro' (Isagro); 'Dragonil' (Agricultura Nacional); 'Echo' (Sipcam); 'Estampe' (France) (Bayer CropScience); 'Faber' (Tripart); 'Flute' (Sipcam UK); 'Mainstay' (Quadrangle); 'Orchid' (GreenCrop); 'Passport' (SDS Biotech KK); 'Pilarich' (Pilarquim); 'Pugil' (Sipcam); 'Repulse' (Hortichem); 'Rover' (Sipcam); 'Rumble' (Probelte); 'Talone' (Chemiplant); 'Terranil 90DF' (Agriliance); 'Thayonil' (Agrochem); 'Ultrafaber' (Tripart) mixtures: 'Alto Elite' (+ cyproconazole) (Syngenta); 'Bravo C/M' (+ copper oxychloride) (Syngenta); 'Bravocarb' (+ carbendazim) (Syngenta); 'Folio Gold' (+ metalaxyl-M) (Syngenta); 'Folio' (+ metalaxyl) (Syngenta); 'Lynx' (+ hexaconazole) (Syngenta); 'Reach' (+ triadimefon) (Syngenta); 'Sambarin' (+ propiconazole) (Syngenta); 'Sirius' (+ hexaconazole) (Syngenta); 'Abitre' (+ tetraconazole) (Bayer CropScience); 'Adagio' (+ mancozeb) (Interfarm); 'Allure' (+ prochloraz) (Bayer CropScience, BASF); 'Arbitre' (+ tetraconazole) (Bayer CropScience); 'Blizzard' (+ cymoxanil) (Nihon Nohyaku); 'Bravo S' (+ sulfur) (Helena); 'Diva' (+ iprodione) (Bayer CropScience, BASF); 'Eminent Star' (+ tetraconazole) (Isagro); 'Flouronil' (+ metalaxyl-M) (Nufarm Americas); 'Guru' (+ mancozeb) (Interfarm); 'Halo' (+ flutriafol) (Cheminova); 'Impact Excel' (+ flutriafol) (Cheminova); 'Moncut CL' (+ flutolanil) (Nihon Nohyaku); 'Music' (+ tetraconazole) (Sipcam Phyteurop); 'Prospa' (+ flutriafol) (Cheminova); 'Soleyou' (+ carbendazim) (Calliope); 'Spectro' (+ thiophanate-methyl) (Cleary); 'Tattoo C' (+ propamocarb hydrochloride) (Bayer CropScience); 'Terranil CU' (+ copper oxychloride) (Agriliance); 'Terranil S' (+ sulfur) (Agriliance); 'Vista CT' (+ fluquinconazole) (Bayer CropScience, BASF); 'Voodoo' (+ tetraconazole) (UK) (Sipcam); 'Walabi' (+ pyrimethanil) (Bayer CropScience, BASF) Discontinued products: 'Exotherm Termil' * (Zeneca); 'Baton' * (Bayer); 'Miros' * (Sipcam); 'Strada' * (Sipcam UK); 'UK Rover 500' * (Sipcam) mixtures: 'PP 375' * (+ flutriafol) (Zeneca); 'Adagio' * (+ mancozeb) (PBI); 'Ashlade Mancarb Plus' * (+ maneb+ carbendazim) (Ashlade); 'Merlin' * (+ propamocarb hydrochloride) (Aventis); 'Octolan' * (+ cyproconazole) (Novartis); 'Triumph' * (+ flusilazole) (DuPont); 'Victor' * (+ maneb+ carbendazim) (Tripart); 'Voodoo' * (+ tetraconazole) (Monsanto)

ANALYSIS
Product analysis by glc (AOAC Methods, 17th Ed., 999.04; D. L. Ballee et al., Anal. Methods Pestic. Plant Growth Regul., 1976, 8, 263). Residues determined by gc-ms, details available from Syngenta. In drinking water by glc with ECD (AOAC Methods, 17th Ed., 990.06). Details available from Syngenta.

MAMMALIAN TOXICOLOGY
Reviews CAG (see part 2 of Bibliography). IARC ref. 30; 73 class 2B Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for albino rabbits >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Evidence in humans of contact dermatitis with repeated exposure. Inhalation LC50 (1 h) for rats 0.52 mg/l air; (4 h) for rats 0.10 mg/l air. NOEL Chronic administration of chlorothalonil has been associated with renal hyperplasia and hyperkeratosis of the forestomach in the kidney and forestomach of rats and male mice. These pre-neoplastic lesions precede subsequent tumour development in the rodent kidney and forestomach. The mode of action has been demonstrated to be epigenetic with a NOEL of 1.8 in rats and 1.6 in mice. In dogs, the pattern of toxicity is different from that in rodents with no evidence of toxicity in the kidney or forestomach, and a NOEL of at least 3 mg/kg b.w. (JMPR 1994). ADI (JMPR) 0.03 mg/kg [1994]; (EPA) 0.02 mg/kg (RED 1998). Toxicity class WHO (a.i.) U; EPA (formulation) II ('Bravo' SC) EC classification R40| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >4640 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >10 000 mg/kg diet. Fish LC50 (96 h) for rainbow trout 47, bluegill sunfish 59, channel catfish 43 mg/l. Daphnia LC50 (48 h) 70 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 210 mg/l; EC50 (72 h) for Navicula pelliculosa 5.1 mg/l. Other aquatic spp. LC50 (48 h) for Crangonyx pseudogracilis 64 mg/l, Chironomus riparius 110 mg/l, Cloeon dipterum 600 mg/l; LC50 (24 h) for Brachionus calyciflorus 24 mg/l. Bees LD50 for honeybees (oral) >63 mg/bee; (contact) >101 mg/bee. Worms LC50 (14 d) >404 mg/kg. Other beneficial spp. LR50 (7 d) for Typhlodromus pyri >18.75 kg/ha; LR50 (48 h) for Aphidius rhopalosiphi >18.75 kg/ha.

ENVIRONMENTAL FATE
EHC 183 (WHO, 1996) Animals Chlorothalonil is not well absorbed following oral dosing. It reacts with glutathione in the gut rumen, or immediately on absorption into the body, to give mono-, di- or tri- glutathione conjugates. These may be excreted through urine or faeces, or subject to further metabolism resulting in thiol or mercapturic acid derivatives. Excretion of these in urine is believed to be significantly greater in rats than in dogs or primates. In ruminants, the major identified metabolite is the the 4-hydroxy derivative; no parent material is found. Plants In plants the majority of residues remain as parent compound; 4-hydroxy-2,5,6-trichloroisophthalonitrile is found as a metabolite to a limited extent. Soil/Environment Koc 1600 (sand) to 14 000 (silt), indicating low mobility to immobile. In aerobic and anaerobic soil studies, DT50 is 0.3-28 d (20 ºC). Stable to hydrolysis at pH 5-7, at pH 9 (22 °C), DT50 is 38 d. Degradation is faster in biotic aquatic systems, typical DT50 (aerobic) <8 h, (anaerobic) <10 d. A wide variety of metabolites are formed which are in turn degraded further..