Phenmedipham 甜菜宁

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甜菜宁

中文通用名:甜菜宁
英文通用名: Phenmedipham
商品名:苯敌草(Betanal)、凯米丰(Kemifan)、Betamix
化学名称: 3-[(甲氧羟基)氨基]苯基-N-(3-甲基苯基-)氨基甲酸酯

理化性质
纯化合物为无色结晶,0.25-0.3,熔点140-144°C,147°C时分解,蒸气压25°C 1.32MPa.室温下在水中溶解度为4.7mg/L,丙酮中200g/kg,甲醇中50g/kg,苯中2.5g/kg,异拂尔酮中231g/kg.原药有效成分>97%,熔点140-144°C。在碱性介质中易分解。

性能
选择性芽后氨基甲酸酯类除草剂。商品名:苯敌草。毒性较低。对皮肤和眼睛有轻度刺激性。对鸟类的毒性较低,对蜜蜂的毒性较低。
作用机制:药效受土壤类型和湿度影响小。温度对甜菜宁的药效和甜菜安全性影响很大,喷药时气温在20℃以上时,有利于药剂在叶面上的吸收发挥药效,温度过高和过低作物生长受抑制易产生药害,喷药时宜选择晴天进行。在土壤中不易被雨水淋溶,半衰期约25天。

应用
甜菜宁为选择性苗后茎叶处理剂,适用于甜菜、草莓等作物田防除多种双子叶杂草。如藜属、荠菜、野芝麻、扁蓄、卷茎蓼、繁缕、野萝卜等,但蓼、龙葵、苦苣菜、猪殃殃等杂草耐药性强,对禾本科杂草、莎草科杂草和末萌发的杂草无效。制剂为16%凯米丰乳油一次用药的适宜时间在杂草2~4叶期进行。在气候条件不好、干旱、杂草出苗不齐的情况下宜采用低量分别几次用药。一次施药的剂量为一亩用330~400毫升(有效成分53.3~64克),低量分别几次喷药推荐亩用200毫升,每隔7~10天重复喷药一次,共2~3次即可。每亩对水20升均匀喷雾,高温高湿有助于杂草叶片吸收。一般每公顷用有效成分720~960克,加工300~450升,不加润湿剂,作茎叶喷雾处理。为扩大杀草谱可用甜菜宁与甜菜安混合剂,也可以与其他防除禾本科杂草除草剂如烯禾定、喹禾灵等混用,施药后要求6小时内无降雨。本品可与其他防除单子叶杂草的除草剂(如拿捕净等)混用。

 

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phenmedipham
Herbicide
HRAC C1 WSSA 5; phenyl carbamate herbicide

  phenmedipham

NOMENCLATURE
Common name phenmedipham (BSI, E-ISO, ANSI, WSSA, JMAF); phenmédiphame ((m) F-ISO)
IUPAC name methyl 3-(3-methylcarbaniloyloxy)carbanilate; 3-methoxycarbonylaminophenyl 3'-methylcarbanilate
Chemical Abstracts name 3-[(methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate
Other names PMP CAS RN [13684-63-4] Development codes SN 38 584 (Schering); ZK 15320; EP-452

PHYSICAL CHEMISTRY
Composition Tech. grade is >97% pure. Mol. wt. 300.3 M.f. C16H16N2O4 Form Colourless crystals. M.p. 143-144 ºC; (tech., 140-144 ºC) V.p. 1.33 ´ 10-6 mPa (25 ºC) KOW logP = 3.59 (pH 3.9) Henry 5 ´ 10-8 Pa m3 mol-1 (calc.) S.g./density 0.34-0.54 (20 ºC) Solubility In water 4.7 mg/l (room temperature). Soluble in polar organic solvents. In acetone, cyclohexanone c. 200, methanol c. 50, chloroform 20, benzene 2.5, hexane c. 0.5, dichloromethane 16.7, ethyl acetate 56.3, toluene c. 0.97, 2,2,4-trimethylpentane 1.16 (all in g/l, 20 ºC). Stability Stable up to 200 ºC. Very stable in acidic media, but hydrolysed in neutral and alkaline media; DT50 (22 ºC) 50 d (pH 5), 14.5 h (pH 7), 10 min (pH 9). In solution (pH 3.8) irradiated at 280 nm, DT50 9.7 d. pKa <0.1

COMMERCIALISATION
History Herbicide reported by F. Arndt & C. Kötter (Abstr. Int. Congr. Plant Prot., 6th, Vienna, 1967, p. 433). Introduced by Schering AG (now Bayer CropScience). Patents GB 1127050 Manufacturers Bayer CropScience; Griffin; Sharda; Synthesia; United Phosphorus Ltd

APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Mode of action Selective systemic herbicide, absorbed through the leaves, with translocation primarily in the apoplast. Uses Used post-emergence, at 1 kg/ha, in beet crops, especially sugar beet, after the emergence of most broad-leaved weeds and before they develop more than 2-4 true leaves; also used on strawberries, spinach, peas, mangold and red beet. Phytotoxicity Non-phytotoxic to beet crops. Formulation types EC; SC; oil-SC; SL; WG. Compatibility Incompatible with alkaline substances. Selected products: 'Alegro' (Bayer CropScience); 'Beetup' (United Phosphorus Ltd); 'Beta' (Stefes, Tripart); 'Betanal' (Bayer CropScience); 'Betapost' (Agriphar); 'Betasana' (United Phosphorus Ltd); 'Herbasan' (Nufarm UK); 'Kemifam' (Bayer CropScience); 'Kontakt' (Feinchemie Schwebda); 'Mandolin' (Griffin); 'Punter' (Barclay); 'Spin-aid' (Bayer CropScience); 'Vangard' (FCC); mixtures: 'Betanal Tandem' (+ ethofumesate) (Bayer CropScience)

OTHER PRODUCTS
'Betanal Flo' (Bayer CropScience); 'Betosip' (Sipcam); 'Crotale' (Stefes); 'Dancer' (Sipcam); 'MSS Protrum G' (Nufarm UK) mixtures: 'Agricola Lens' (+ lenacil) (Agricola); 'Beetup Pro' (+ desmedipham+ ethofumesate) (United Phosphorus Ltd); 'Beetup Trio' (+ desmedipham+ ethofumesate) (United Phosphorus Ltd); 'Betamix Progress' (+ desmedipham+ ethofumesate) (Bayer CropScience); 'Betamix' (+ desmedipham) (Bayer CropScience); 'Betanal Compact' (+ desmedipham) (Bayer CropScience); 'Betanal Progress OF' (+ desmedipham+ ethofumesate) (Bayer CropScience); 'Betanal Quattro' (+ desmedipham+ ethofumesate+ metamitron) (Bayer CropScience); 'Betanal Trio' (+ ethofumesate+ metamitron) (Bayer CropScience); 'Betasana Trio' (+ desmedipham+ ethofumesate) (United Phosphorus Ltd); 'Betosip Combi' (+ ethofumesate) (Sipcam); 'Bettix Triple' (+ desmedipham+ ethofumesate+ metamitron) (United Phosphorus Ltd); 'Contatto' (+ desmedipham+ ethofumesate) (Feinchemie Schwebda); 'Goalpost' (+ ethofumesate) (Barclay); 'Goldpost' (+ ethofumesate) (Barclay); 'Kontakt Twin' (+ ethofumesate) (Feinchemie Schwebda); 'MagicTandem' (+ ethofumesate) (Stefes); 'Powertwin' (+ ethofumesate) (Feinchemie Schwebda); 'Progress' (+ desmedipham+ ethofumesate) (Bayer CropScience); 'Safen' (+ desmedipham) (Azot); 'Saherb' (+ trifluralin+ desmedipham+ ethofumesate) (Azot); 'Synbetan Duo' (+ desmedipham) (Synthesia); 'Synbetan Mix' (+ desmedipham) (Synthesia); 'Synbetan P Forte' (+ ethofumesate) (Synthesia); 'Twin' (+ ethofumesate) (Feinchemie Schwebda, Headland) Discontinued products: 'Betaflow' * (AgrEvo); 'Betanal E' * (Aventis); 'Atlas Protrum K' * (Atlas); 'Beetomax' * (Fine); 'Betalion' * (Portman); 'Betaren' * (PBI); 'Cirrus' * (Quadrangle); 'Dephend' * (Headland); 'Fender' * (ISK Biosciences); 'Forte' * (Stefes); 'Goliath' * (ABM); 'Medipham' * (Stefes); 'MSS Betaren' * (Mirfield); 'Pistol' * (ABM); 'Protrum K' * (Nufarm Whyte); 'Suplex' * (UCP) mixtures: 'DUK 880' * (+ lenacil) (DuPont); 'Medimat 2' * (+ ethofumesate) (Stefes); 'Stefes 880' * (+ lenacil) (Stefes); 'Tandem' * (+ ethofumesate) (Stefes)

ANALYSIS
Product analysis by titration (CIPAC Handbook, 1985, 1C, 2181) or by hplc (ibid., 2184); method available from Bayer CropScience. Residues by glc (K. Kossmann & N. A. Jenny, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 611); in soil by hplc or by hydrolysis to m-toluidine, derivatives of which are determined by glc with ECD or by colorimetry (K. Kossmann, Weed Res., 1970, 10, 340). Details available from Bayer CropScience.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >8000, guinea pigs and dogs >4000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 1000, rats 2500 mg/kg. Not a skin sensitiser. Inhalation LC50 (4 h) for rats >7.0 mg/l. NOEL (2 y) for rats 100, dogs 1000 mg/kg; (90 d) for rats and dogs 200 mg/kg diet. ADI 0.03 mg/kg. Other Acute i.p. LD50 for rats >5000 mg/kg. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
Birds Acute oral LD50 for chickens >2500, mallard ducks >2100 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >6000 mg/kg diet. Fish LC50 (96 h) for rainbow trout 1.4-3.0, bluegill sunfish 3.98 mg/l. LC50 (96 h) for harlequin fish 16.5 mg/l (15.9% EC formulation). Daphnia LC50 (72 h) 3.8 mg/l. Algae IC50 (96 h) 0.13 mg/l. Bees Not toxic to bees; LD50 (oral) >23 mg/bee; (contact) 50 mg/bee. Worms EC50 (14 d) >156 mg/kg soil.

ENVIRONMENTAL FATE
Animals In mammals, following oral administration, 99% is excreted within 72 hours, mainly in the urine. Hydrolysis to methyl N-(3-hydroxyphenyl)carbamate and conjugation to glucuronides and ethereal sulfates are the major steps in metabolism. Plants Methyl N-(3-hydroxyphenyl)carbamate is the major metabolite in plants. Soil/Environment DT50 in soil c. 25 d, DT90 c. 108 d. Metabolites include methyl N-(3-hydroxyphenyl)carbamate and m-aminophenol, and subsequently complexes with soil components (R. Senawana et al., Bull. Environ. Contam. Toxicol., 1971, 6, 322-327). Phenmedipham does not accumulate in soil, nor is there any relevant uptake by following crops. Due to its favourable physico-chemical parameters, no risk of groundwater contamination is to be expected. Koc 2400.