Tetradifon 三氯杀螨砜

三氯杀螨砜

中文通用名：三氯杀螨砜
其他中文名：涕滴恩,天地红,太地安,退得完
英文通用名：tetradifon Tedion,TON,Chlorodifon,V-18
分子式：C12H6Cl4O2S
农药类别：杀螨剂
化学类别：有机氯
作用方式：触杀
化学名称：1,2,4-三氯-5-[(4-氯苯基)磺酰]苯
分析方法：气谱法(原药ZBG25015-90)；气谱法(CIPAC手册,1983,1B,1901)
理化性质：无色晶体(原药微黄)，熔点148~149℃(纯品)，>=144℃(原药)，蒸气压 3.2×10－8Pa(20℃)，密度1.515(20℃)，KowlogP=4.61，溶解度水0.05(10℃)， 0.08(20℃)mg/L，丙酮82g/L，苯148g/L，氯仿255g/L，环己酮200g/L，甲苯 135，二甲苯115g/L(10℃)，二恶烷223，煤油，甲醇10g/L(10℃)，非常稳定， 甚至在强酸、碱环境中。对光、热稳定，抗强氧化剂。

相关其他
三氯杀螨砜的中毒症状：
症状与体征是其对神经系统的刺激作用所致，如头痛、眩晕、忧虑烦恼、情 绪激动，也有呕吐、四肢软弱、双手震颤、失去时间和空间的定向，随后出 现阵发痉挛。
采取急救治疗：[1]无特殊解毒剂，如经口摄入要催吐。[2]尽可能保持病人安静，控制病人激 动，清醒时，可给予常用剂量的巴比妥与其它镇静剂。[3]注意维持呼吸，如 有衰竭使用人工呼吸。[4]禁忌用肾上腺素或阿托品。
注意事项：[1]不能用三氯杀螨砜杀冬卵。[2]当红蜘蛛为害重，成螨数量多时，必须与其 它药剂混用，效果才好。 [3]该药对柑桔锈螨无效。

作用特点：非内吸具长效、渗透植物组织的作用，除对成螨无效外，对卵及其它生长阶 段均有抑制及触杀作用，也能直接使用雌螨不育或导致卵不孵化。

用途: 为接触性杀螨剂，具有良好的杀螨卵和幼螨的效果，残效期长达40～50d，可用于防治棉、柑橘、苹果等植物初孵化螨、卵盛期或成螨较少时期。使用浓度为0.05%时可抑制雌螨产卵和使之不育

使用方法：
1.防治山楂叶螨，在苹果开花前后喷20%可湿性粉剂800～1000倍液，与0.3～0.5波美度石硫合剂或50%硫悬浮剂300～400倍液混用效果好。
2.防治苹果全爪螨时，以落花后、第1代卵盛期喷800～1000倍20%三氯杀螨砜可湿性粉剂，与40%氧化乐果1000倍液混用，可兼杀成螨和卵。
3.以柑橘始叶螨为主而成螨数量又多时，可在谢花后用20%三氯杀螨砜800～1000倍液与40%乐果乳油3000倍液混合喷雾。
4.防治柑橘全爪螨、始叶螨和裂爪螨时，可在柑橘春梢芽长5～10cm时(3月中下旬)，树上喷20%三氯杀螨砜可湿性粉剂600～800倍液，有效期长达30天以上。
5.若以柑橘全爪螨为主的橘园，应与46%晶体石硫合剂250倍液混合喷雾，既杀卵、又杀成螨。
6.与马拉硫磷复配(13.5%＋10.5%)为烟雾剂，可熏杀室内花卉的红蜘蛛、蚜虫。
7.防治棉花上的害螨，可用20%可湿性粉剂750～500g/hm2对水喷雾。

三氯杀螨砜生产方法：
由三氯苯经氯磺化制得中间体三氯苯磺酰氯，再与氯苯在三氯化铝存在下缩合制得三氯杀螨砜。
具体过程如下：
1、氯磺化：将三氯苯滴加到氯磺酸中，氯磺酸过量，反应温度80~90℃,氯磺化时间3h。反应排出的气体用水吸收。生成的三氯苯磺酰氯经冷却析出、水洗(必要时加少量硝酸氧化，使低硫化合物转变为三氯苯磺酰氯)，最后经脱水、干燥后供缩合用。
2、缩合：三氯苯磺酰氯与氯苯缩合生成三氯杀螨砜。反应为亲电子二级反应，用AlCl3或FeCl3作催化剂，氯苯滴加，反应温度145~155℃，反应时间1.5~3h。缩合产物倾入90℃热水中，搅拌析出三氯杀螨砜，经水洗、烘干得原粉。

分析方法：
产品分析用具FID的GLC，残留物测定用GLC法。三氯杀螨砜含量的测定，按金属钠一异丙醇法测定有机氯含量。根据有机氯含量可按下式计算三氯杀螨砜含量。

tetradifon
Acaricide

NOMENCLATURE
Common name tetradifon (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF); tedion* (former name, Turkey and USSR); no name (Portugal)
IUPAC name 4-chlorophenyl 2,4,5-trichlorophenyl sulfone
Chemical Abstracts name 1,2,4-trichloro-5-[(4-chlorophenyl)sulfonyl]benzene
CAS RN [116-29-0] EEC no. 204-134-2 Development codes V-18 (Duphar) Official codes ENT 23 737

PHYSICAL CHEMISTRY
Composition Tech. grade tetradifon is ³95% pure. Mol. wt. 356.0 M.f. C12H6Cl4O2S Form Colourless crystals; (tech., off-white powder with a weak aromatic odour. M.p. 146 ºC (pure); (tech. ³144 ºC) V.p. 9.4 ´ 10-7 mPa (25 ºC) KOW logP = 4.61 Henry 1.46 ´ 10-4 Pa m3 mol-1 S.g./density 1.68 (20 °C) Solubility In water 0.078 mg/l (20 ºC). In acetone 67.3, methanol 3.46, ethyl acetate 67.3, hexane 1.52, dichloromethane 297, xylene 105 (all in g/l, 20 °C) Stability Extremely stable, even in strong acids and alkalis. Stable to heat and to sunlight. Resistant to strong oxidising agents.

COMMERCIALISATION
History Acaricide reported by H. O. Huisman et al. (Nature (London), 1955, 176, 515). Introduced by N. V. Philips-Roxane (now Crompton Corp.). Patents NL 81359; US 2812281 Manufacturers Crompton

APPLICATIONS
Mode of action Non-systemic acaricide. Long-acting, penetrating through the plant tissue. Exhibits contact action on eggs and all non-adult stages, and also acts indirectly by sterilisation of females, leading to the development of non-viable eggs. Uses Larvicidal and ovicidal activity on a large range of phytophagous mites. Used on many fruit crops (including citrus), vegetables, cotton, hops, tea and ornamentals. For most crops, the recommended concentration is 0.0125-0.015% a.i.; in cotton, a dosage of 150-300 g/ha is used. Phytotoxicity Except for some species of ornamentals (dahlia, ficus, cissus, primula, kalanchoe and some rose cultivars), non-phytotoxic when used as recommended. Formulation types EC. Selected products: 'Tedion V-18' (Crompton); mixtures: 'Cekudit-combi' (+ dicofol+ dimethoate) (Cequisa); 'Vapcothion' (+ dicofol) (Vapco); 'Verecar T' (+ parathion-methyl) (Griffin)

OTHER PRODUCTS
'Tedone' (Isagro); 'Tetrasit' (AgroSan) mixtures: 'Acarelte Forte' (+ dinobuton) (Probelte); 'Acrex Super' (+ dinobuton) (Efthymiadis); 'Cekudit' (+ dicofol) (Cequisa); 'Dictator-Plus' (+ propargite) (Vapco); 'Rizonil' (+ propanil) (Papaeconomou); 'Sepiclar T' (+ methomyl) (Griffin) Discontinued products: 'Mitifon' * (Hellenic); 'Tedion' * (DuPont) mixtures: 'Childion' * (+ dicofol) (Hortichem)

ANALYSIS
Product analysis by glc with FID (CIPAC Handbook, 1983, 1B, 1901; AOAC Methods, 17th Ed., 981.02). Residues determined by glc (ibid., 976.23; Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 488; A. van Rossum et al., ibid., 1978, 10, 119).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats >14 700 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >10 000 mg/kg. Non-irritating to skin; slight eye irritant (rabbits). Inhalation LC50 (4 h) for rats >3 mg/l air. NOEL In 2 y feeding study, NOAEL for rats 300 mg/kg diet. In 2-generation study, reproduction NOEL for rats 200 mg/kg diet. No teratogenic effects in rats and rabbits. Not mutagenic. Other Acute i.p. LD50 for rats >2500, mice >500 mg/kg. Toxicity class WHO (a.i.) U; EPA (formulation) III

ECOTOXICOLOGY
Birds Dietary LC50 (8 d) for bobwhite quail, Japanese quail, pheasants, mallard ducks >5000 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 880, channel catfish 2100, rainbow trout 1200 mg/l. Daphnia LC50 (48 h) >2 ppm. Algae EC50 (96 h) for Selenastrum capricornutum >100 mg/l. Bees Not hazardous to bees when used as recommended; LD50 (contact) >1250 mg/bee. Worms LD50 >5000 mg/kg substrate. Other beneficial spp. Harmless at normal rates to the natural enemies of spider mites.

ENVIRONMENTAL FATE
EHC 67 (WHO, 1986). EHC report concludes there is no evidence of risk to the environment when used as recommended. Animals In rats, following oral administration of a single dose, 70% was excreted via the bile in the faeces within 48 hours. Plants Non-systemic; tetradifon is not metabolised on plants. Soil/Environment Strongly and irreversibly bound to soil/humic acid complex; virtually immobile in soil.