Chlorthal-dimethyl 敌草索

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CAS号:1861-32-1
英文名称:Chlorthal-dimethyl
化学名称:2,3,5,6-四氯-1,4-苯二甲酸甲酯;Dimethyl;2,3,5,6-tetra-chloro-1,4-benzenedicarboxylate;
其他名称:氯酞酸二甲酯; DCPA
分子式:C10H6Cl4O4
分子量:332.19

性质:白色针状结晶。熔点154-155℃。40℃时蒸气压低于66.7Pa。25℃水中溶解度小于0.5ppm,丙酮中为10%(W/W),苯中25%。二噁烷中12%,甲苯中17%,二甲苯中14%。
毒性:大鼠急性经口LD50>3000mg/kg,家兔急性经皮LD50>10000mg/kg。

作用特点及杀草谱:苯甲酸类芽前除草剂,对萌发至二叶期的稗草有显著的活性,对旱地马唐等芽前杂草也有良好的防除效果。用量为6~4kg/ha。

剂型:制剂有75%可湿性粉剂、2.5%颗粒剂、5%颗粒剂
制备方法:采用强甲基化剂(如重氮甲烷或硫酸二甲酯),使四氯对苯二甲酸烷基化;或由四氯对苯二甲酰氯与甲醇酯化而得。中间体四氯对苯二甲酰氯有两种主要合成方法。(1)由对二甲苯侧链氯化、水解、环上氯化而得。(2)由对苯二甲酸经酰氯化、氯化而得。

生产情况:温州康达化工科技有限公司(200吨/年);衢州市瑞尔丰化工有限公司
 

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chlorthal-dimethyl
Herbicide
HRAC K1 WSSA 3; benzenedicarboxylic acid

  Chlorthal-dimethyl

NOMENCLATURE
chlorthal-dimethyl
Common name chlorthal-dimethyl (BSI, E-ISO, (m) F-ISO (before 1990)); DCPA (WSSA); TCTP (JMAF)
Chemical Abstracts name dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate
Other names dimethyl tetrachloroterephthalate CAS RN [1861-32-1] Development codes DAC 893

chlorthal
Common name chlorthal (WSSA; BSI, E-ISO, (m) F-ISO (since 1990))
IUPAC name tetrachloroterephthalic acid
Chemical Abstracts name 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid
CAS RN [2136-79-0]

PHYSICAL CHEMISTRY
chlorthal-dimethyl
Mol. wt. 332.0 M.f. C10H6Cl4O4 Form Colourless crystals. M.p. 156 ºC V.p. 0.21 mPa (25 ºC, gas saturation method) KOW logP = 4.28 (25 ºC) Henry 1.39 ´ 10-1 Pa m3 mol-1 (calc.) Solubility In water c. 0.5 mg/l (25 ºC). In benzene 250, toluene 170, xylene 140, dioxane 120, acetone 100, carbon tetrachloride 70 (all in g/kg, 25 ºC). Stability Stable to heat and u.v. light. Decomposes at c. 360-370 ºC.

chlorthal
Mol. wt. 303.9 M.f. C8H2Cl4O4

COMMERCIALISATION
History Herbicide reported by P. H. Schuldt et al. (Proc. Northeast. Weed Control Conf., 1960, p. 42). Chlorthal-dimethyl introduced by Diamond Alkali Co. (later ISK Biosciences Corp.). Patents US 2923634 Manufacturers Amvac

APPLICATIONS
chlorthal-dimethyl
Biochemistry Microtubule assembly inhibition. Mode of action Selective non-systemic herbicide, absorbed by the coleoptiles (grasses) and hypocotyls. Kills germinating seeds. Uses Pre-emergence control of annual grasses and some annual broad-leaved weeds in onions, garlic, leeks, tomatoes, lettuce, cucurbits, capsicums, aubergines, brassicas, potatoes, sweet potatoes, horseradish, field beans, soya beans, cotton, strawberries, ornamentals, established turf, and other crops. Applied at 6.9-11.5 kg 75 WP formulation/ha for sandy-sandy soil, 11.5 -16.1 kg formulation/ha for heavy silt loam. Phytotoxicity Phytotoxic to beet, spinach, flax, and trefoil. Formulation types GR; SC; WP. Selected products: 'Dacthal' (Amvac); 'Erazor' (Amvac); mixtures: 'Decimate' (+ propachlor) (Amvac); 'Ringo' (+ propachlor) (Amvac)

OTHER PRODUCTS
chlorthal-dimethyl
Discontinued products: 'Dimethyl-T' * (Amvac)

ANALYSIS
Product analysis by i.r. spectrophotometry (AOAC Methods, 17th Ed., 970.06; CIPAC Handbook, 1985, 1C, 2034) or by glc with FID (AOAC Methods, 17th Ed., 970.05; CIPAC Handbook, 1985, 1C, 2032). Residues determined by glc (H. P. Burchfield & E. E. Storris, Anal. Methods Pestic. Plant Growth Regul. Food Addit., 1964, 4, 67; Anal. Methods Pestic., Plant Growth Regul., 1972, 6, 616). In drinking water, by glc with ECD (AOAC Methods, 17th Ed., 990.06); the acid metabolites by conversion to methyl ester with diazomethane, then glc with ECD (ibid., 992.32).

MAMMALIAN TOXICOLOGY
chlorthal-dimethyl
Oral Acute oral LD50 for rats and dogs >10.0 g/kg. Skin and eye Acute percutaneous LD50 for albino rabbits >2 g/kg. Mild dermal irritant; slight eye irritant (rabbits). Inhalation LC50 (4 h) for rats >4.5 mg/l. NOEL (2 y) for mice 142, rats 1 mg/kg daily. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
chlorthal-dimethyl
Birds LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 (5 d) for bobwhite quail and mallard ducks >5620 ppm. Fish Non-toxic to fish. LC50 (96 h) for rainbow trout >4.7, bluegill sunfish >5.4 mg/l. Daphnia LC50 (48 h) >4.6 mg/l. Bees Slightly toxic to bees.

ENVIRONMENTAL FATE
Animals In mammals, following oral administration, chlorthal-dimethyl is metabolised to monomethyl tetrachloroterephthalate and 2,3,5,6-tetrachloroterephthalic acid (chlorthal), which are eliminated in the urine. Plants Chlorthal-dimethyl is not metabolised by plants. Soil/Environment Soil DT50 100 d. In soil, microbial degradation leads to monomethyl tetrachloroterephthalate and 2,3,5,6-tetrachloroterephthalic acid (chlorthal). Duration of residual activity in soil is c. 3 months.