Piperophos 哌草磷

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哌草磷

CAS号: 24151-93-7
英文名称:piperophos
化学名称:S-2-甲基哌啶羰基甲基-0,0一二丙基二硫代磷酸酯;S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate
其他名称:Avirosan; C19490[汽巴-嘉基]; Rilof[汽巴-嘉基]
分子式:C14H28NO3PS2
分子量:353.48

理化性质: 纯品为微粘稠透明液体,淡黄色,略带甜气味,沸点>250℃,约190℃在蒸馏时分解,蒸气压32mPa(20℃),密度1.130g/立方厘米(20℃)。溶解度(20℃):水中25mg/L,可与丙酮、苯、二氯甲烷、己烷、甲醇、正辛醇混溶。在20℃时,在5≤pH≤7超过200天损失50%(计算),在pH9时为178天。

毒性:大鼠急性经口LD50324mg/kg。急性经皮LD50>2150mg/kg,对兔眼睛稍有刺激,对皮肤无刺激性。大鼠急性吸入LC50 (1h) >1.96mg/L空气。蜜蜂经口LD50 >22 μg/只,接触LD50 30 μg/只,虹鳟LC50 (96 h)6 mg/l,欧洲鲫鱼5vmg/L,蚯蚓LC50 (14天)为180vmg/kg土。

作用特点及杀草谱: 是一种选择性除草剂。通过幼小杂草的根、胚芽鞘和子叶从土壤中吸收药剂,抑制其生长而死亡。可以防治一年生禾本科杂草和莎草科杂草,如稗草、牛毛毡、眼子菜、日照飘拂草、萤蔺、莎草、鸭舌草、节节草、矮慈姑、小苋菜、水马齿等。对双子叶杂草防效差。

适用作物: 水稻、玉米、棉花、大豆等,对水稻安全。

使用技术: 水稻田,插秧后6-12天,杂草发芽以后,用50%浓乳剂133-200mL/亩,拌混细土或潮砂土15-20kg,均匀撒施,或者加水40-50kg,用一般扇形喷头的喷雾器均匀喷雾,施药时田间保持水层3cm左右,药后5-7天只灌不排,以后按照正常水管理,稻田内水深度变化对除草效果影响不大,但用药后的几天内排水则会影响除草效果。

剂型:制剂有50%浓乳剂,也可与二甲丙乙净(戊草净)或2,4-滴制成混剂。哌草磷和戊草净混合制剂,为稻田用选择性广谱除草剂。其他名有威罗生、排草净、哌净合剂等。

生产方法:由N-(2-甲基哌啶基)氯乙酰胺与O,O-二丙基二硫代磷酸钠反应生成。

生产情况:1969年由汽巴-嘉基公司作为试验性除草剂推广。国内未见有哌草磷生产报道。

其他:汽巴-嘉基公司(Cviba-Gvelgy Lvtd.)获有专利BP1255946,已过期。

 

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piperophos
Herbicide
HRAC K3 WSSA 15

  Piperophos

NOMENCLATURE
Common name piperophos (BSI, E-ISO, (m) F-ISO)
IUPAC name S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate
Chemical Abstracts name S-[2-(2-methyl-1-piperidinyl)-2-oxoethyl] O,O-dipropyl phosphorodithioate
CAS RN [24151-93-7] Development codes C 19 490 (Ciba)

PHYSICAL CHEMISTRY
Mol. wt. 353.5 M.f. C14H28NO3PS2 Form Pale yellow, slightly viscous clear liquid, with a somewhat sweet odour. B.p. >250 ºC; thermal decomposition begins before c. 190 ºC V.p. 0.032 mPa (20 ºC) KOW logP = 4.3 Henry 4.5 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.13 (20 ºC) Solubility In water 25 mg/l (20 ºC). Miscible with benzene, hexane, acetone, dichloromethane and octanol. Stability Stable under normal storage conditions. Slowly hydrolysed at pH 9; DT50 (20 ºC) (calc.) >200 d (5 £pH £7), 178 d (pH 9).

COMMERCIALISATION
History Herbicide reported by D. H. Green & L. Ebner (Proc. Br. Weed Control Conf., 11th, 1972, 2, 822). Introduced by Ciba-Geigy AG (now Syngenta AG). Patents BE 725992; GB 1255946 Manufacturers Syngenta

APPLICATIONS
Biochemistry Inhibits cell division. Mode of action Selective, systemic herbicide, absorbed by the roots, coleoptiles, and leaves of young plants. Uses A selective herbicide active against annual grasses and sedges in direct seeded or transplanted rice, at 330-660 g/ha. Used, in combination with dimethametryn, for the control of both grass and broad-leaved weeds. In tropical regions, piperophos is applied in combination with 2,4-D or cinosulfuron to widen the spectrum against broad-leaved weeds. Formulation types EC; WP. Selected products: 'Rilof' (Syngenta); mixtures: 'Avirosan' (+ dimethametryn) (Syngenta)

OTHER PRODUCTS
Mixtures: 'PIPSET' (+ cinosulfuron) (Syngenta); 'Stamphos' (+ propanil) (Dow AgroSciences)

ANALYSIS
Product analysis by glc. Residues determined by glc with TID. Details of methods available from Syngenta.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 324 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2150 mg/kg. Non-irritant to skin; slight irritant to eyes (rabbits). Inhalation LC50 (1 h) for rats >1.96 mg/l air. NOEL (90 d) for rats 10 mg/kg diet (0.8 mg/kg daily); for dogs 5 mg/kg diet (0.15 mg/kg daily). Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification Xn; R22

ECOTOXICOLOGY
Birds Dietary LC50 (8 d) for Japanese quail 11 629 ppm. Fish LC50 (96 h) for rainbow trout 6, crucian carp 5 mg/l. Daphnia LC50 (48 h) 0.0033 mg/l. Algae EC50 (5 d) for Scenedesmus subspicatus 0.059 mg/l. Bees LD50 (oral) >22 mg/bee; (contact) 30 mg/bee. Worms LC50 (14 d) for earthworms 180 mg/kg soil.

ENVIRONMENTAL FATE
Animals In urine, no unchanged piperophos was present, indicating extensive degradation of the compound. Degradation proceeds via hydrolysis of the thiolo phosphate followed by methylation of the sulfur or hydroxylation of the piperidine moiety. Hydroxylation at the g-carbon leads via ring opening to carboxylic acids. The derivatives are conjugated with glucuronic acid. Plants Degradation of piperophos takes place rapidly in the plant, forming 2-(2'-methyl-1'-piperidinyl)-2-oxoethane sulfonic acid, 2-(2'-methyl-1'-piperidinyl)-2-oxoethanoic acid and a fraction of unknown polar substances. The proposed pathway involves hydrolysis to the corresponding sulfhydryl and hydroxyl derivatives, followed by further oxidation to the sulfonic acid and oxalic acid derivatives. Injection experiments in plants confirmed the capacity of the rice plant to oxidise piperophos derivatives rapidly. Soil/Environment DT50 (field) <30 d; rapid dissipation by biodegradation from soil and paddy systems. Relatively stable to hydrolysis and photolysis.