Quintozene 五氯硝基苯

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五氯硝基苯

CAS号: 82-68-8
英文名称: Quintozine
化学名称:Benzene,pentachloronitro
其他名称:土粒散; 掘地生; 掘地坐
分子式: C6Cl5NO2
分子量:295.33

理化性质:纯品为白色针状结晶。m.p.146℃, b.p.328℃(有分解),蒸气压1.77Pa(25℃),相对密度1.718(25℃)。易溶于苯、氯仿、二硫化碳;稍溶于乙醇;难溶于水。化学性质稳定,贮存几年不失效;在阳光 、空气、温度及一般酸碱条件下均稳定;在土壤中稳定性较高;对金属无腐蚀性。工业品为黄色或灰白色粉末,m.p.约142~143℃。

毒性:大鼠急性经口 LD50>12000mg/kg,原药对大鼠急性经口 LD501700mg/kg,家兔急性经皮 LD50>4000mg/kg。动物试验未见致癌、致畸、致突变现象。鲤鱼 LC50为10~40mg/L (48h)。

作用特点及用途:保护性杀菌剂,优良的土壤杀菌剂,低毒,无内吸作用。用于种子清毒和土壤处理,其杀菌机制是影响菌丝细胞的有丝分裂。用作拌种剂和土壤处理剂,用于防治棉花立枯病、猝倒病,小麦腥黑穗病、散黑穗病,、高梁腥黑穗病,马铃薯疮痂病,甘兰根肿病,莴苣灰霉病等。喷洒可防治水稻纹枯病。用40%粉剂500g拌种100kg;防治棉花苗期病害用40%粉剂1000g拌种100kg;防治油菜菌核病,每百平方米用40%粉剂65.6g拌细土1.5~3kg,在发病初期撒于根部附近;防治马铃薯疮痂病,每百平方米用50%可湿性粉剂375~675g,条施于播种沟内。

剂型:40%、70%粉剂

生产方法 :以碘为催化剂、氯磺酸为溶剂,将2,4,5-三氯硝基苯与氯气在80-85℃反应。溶剂氯磺酸的用量为三氯硝基苯重量的1-3倍,碘用量为三氯硝基苯重量的0.2-0.3%,通氯至过量1%。然后冷至30℃,滤出五氯硝基苯,用80-90℃热水洗至中性,70℃下干燥,可得含量98-99%的产品,收率94%。而2,4,5-三氯硝基苯是由1,2,4三氯苯硝化得到的。上述方法耗用碘和氯磺酸,设备易腐蚀,另一种生产方法是采用由六六六无毒体得到的三氯苯埋接硝化、氯化,可得到氯硝基苯含量大于70%的原粉。原料消耗定额:三氯苯(98%)880kg/t、液氯930kg/t、硫酸(折100%)1020kg/t、硝酸(98%)350kg/t、氯磺酸(90%以上)1100kg/t。

生产情况:江苏托球农化有限公司(盐城市龙跃农药有限公司) ;德州大成农药有限公司;武汉思嘉农药技术发展有限公司

其他:由于可能存在二噁英杂质,澳大利亚于2010年4月暂停五氯硝基苯的农药登记至2011年4月。

 

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quintozene
Fungicide
FRAC 14, F3; aromatic hydrocarbon; chloro/nitrophenyl

  quintozene

NOMENCLATURE
Common name quintozene (BSI, E-ISO, (m) F-ISO); PKhNB (USSR); PCNB (JMAF)
IUPAC name pentachloronitrobenzene
Chemical Abstracts name pentachloronitrobenzene
CAS RN [82-68-8] EEC no. 201-435-0

PHYSICAL CHEMISTRY
Composition Tech. grade is 99% pure. Mol. wt. 295.3 M.f. C6Cl5NO2 Form Colourless needles; (tech., pale yellow crystals). M.p. 143-144 ºC; (tech., 142-145 ºC) B.p. 328 ºC (with slight decomposition) V.p. 12.7 mPa (25 ºC) KOW logP = 5.1 S.g./density 1907 kg/m3 (21 ºC) Solubility In water 0.1 mg/l (20 ºC). In toluene 1140, methanol 20, heptane 30 (all in g/l). Stability Stable to heat. Stable in acidic media, but hydrolysed by alkalis. Some surface colouring after 10 h exposure to sunlight.

COMMERCIALISATION
History Introduced as a fungicide by I. G. Farbenindustrie AG (now Bayer AG, who no longer manufacture or market it). Patents DE 682048 Manufacturers Amvac; Bayer CropScience; Crompton; Mitsui

APPLICATIONS
Biochemistry Proposed mode of action is lipid peroxidation. Mode of action Seed and soil, contact fungicide. Uses Control of damping-off diseases in brassicas, lettuce, cotton, flower crops, tomatoes, etc.; Rhizoctonia spp. in brassicas, lettuce, tomatoes, and flower crops; bulb rot and tulip fire in tulips; dollar spot, red thread, and snow mould in turf; Rhizoctonia solani and scab in potatoes; bunt and dwarf bunt of wheat; smut and white rot in onions; white rot in garlic; club root of brassicas; and soil-borne Sclerotium, Sclerotinia, and Botrytis spp. in many glasshouse crops. Also used on peanuts, bananas, beans, peas, rice, maize, safflowers, sorghum, soya beans, etc. Applied at 1-1.5 kg/ha. Formulation types DP; EC; GR; SC; WP; Seed treatment. Compatibility Incompatible with alkaline materials. Selected products: 'Blocker' (Amvac); 'Folosan' (Crompton); 'RTU' (Gustafson); 'Terraclor' (Crompton); mixtures: 'System 3' (+ Bacillus subtilis+ metalaxyl) (Crompton, Helena)

OTHER PRODUCTS
'Agromin' (AgroSan); 'Brassicol' (Bayer CropScience); 'Parflo' (Amvac); 'Terrazan' (Crompton); 'Trigran-S' (Gustafson); 'Tritisan' (Bayer CropScience); 'Turfcide' (Crompton); 'Win-Flo' (Amvac) mixtures: 'Dot-Son' (+ disulfoton) (Platte); 'Kodiak A-T' (+ metalaxyl) (Gustafson); 'Mefenoxam PC' (+ metalaxyl-M) (Syngenta); 'Ridomil Gold PC' (+ metalaxyl-M) (Syngenta); 'Ridomil PC' (+ metalaxyl) (Syngenta); 'Terraclor Super X' (+ etridiazole) (Crompton) Discontinued products: 'Avicol' * (Kemira FC); 'Kobu' * (Takeda); 'Kobutol' * (Hokko)

ANALYSIS
Product analysis by glc with FID (CIPAC Handbook, 1985, 1C, 2213; AOAC Methods, 17th Ed., 982.04). Residues determined by glc (Pestic. Anal. Man.,1979, I, 201A, 201G, 201I; Man. Pestic. Residue Anal., 1987, I, 4-6, S8, S9, S12, S19; Anal. Methods Residues Pestic., 1988, Part I, M1, M12).

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 74, 76 (see part 2 of the Bibliography). Monograph for the placement of quintozene onto annex 1 of European directive 91/414 (1997). IARC ref. 5 Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Not irritating to skin; slightly irritating to eyes (rabbits). Inhalation LC50 (4 h) for rats >1.7 mg/l. NOEL (2 y, oncogenic) for rats 1 mg/kg b.w. daily; (1 y, feeding) for dogs 3.75 mg/kg b.w. daily. ADI (JMPR) 0.01 mg/kg b.w. (for quintozene containing <0.1% hexachlorobenzene) [1995]. Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification Xi; R43

ECOTOXICOLOGY
Birds LD50 for mallard ducks 2000 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 ppm. Fish LC50 (96 h) for rainbow trout 0.55, bluegill sunfish 0.1 ppm. Daphnia LC50 (48 h) 0.77 mg/l. Other aquatic spp. LC50 (96 h) for shrimps 0.012, oyster 0.029 ppm. Bees LD50 (contact) >100 mg/bee.

ENVIRONMENTAL FATE
EHC 41 (WHO, 1984). Animals In mammals, the major routes of elimination are as unchanged material in the faeces or as metabolites in the urine. In rats, sheep and monkeys, the principal metabolite is pentachloroaniline (formed by reduction of the nitro group). Other metabolites include pentachlorophenol, pentachlorothioanisole, pentachlorobenzene, bis-methyl-tetrachlorobenzene, methyl pentachlorophenyl sulfide and N-acetyl-S-pentachlorophenylcysteine (E. J. Kuchar et al., J. Agric. Food Chem., 1969, 17, 1237-1240; W. Koegel et al., Chemosphere, 1979, 89-105; P. W. Aschbacher & V. J. Feil, J. Agric. Food Chem., 1983, 31, 1150). Plants In plants, quintozene undergoes conversion to pentachloroaniline, methylthiopentachlorobenzene and a variety of chlorophenyl methyl sulfoxides and sulfones. Soil/Environment Persists in soil, with a half-life of c. 4-10 months. Part is lost from the soil by volatilisation. Biodegradation occurs, mainly to pentachloroaniline and also methylthiopentachlorobenzene. For details of effects on soil organisms, see E. R. Ingham, Crop Prot., 1985, 4, 3-32. Koc for adsorption 6030 (silt loam), 2966 (sand); for desorption 9584 (silt loam), 3285 (sand).