Daimuron 香草隆，杀草隆

香草隆，杀草隆

CAS号: 42609-52-9
英文名称: Dymron
化学名称：N'-(Α,Α-二甲基苄基)-N-(对甲苯基)脲; n-(4-methylphenyl)-n’-(1-methyl-1-phenylethyl)-ure
其他名称：莎扑隆;莎草隆;香草隆; k223;
分子式: C17H20N2O
分子量: 268.35

理化性质：纯品为白色针状结晶。m.p.203℃。20℃时溶解度为：甲醇、乙醇1%，丙酮、乙醚10%，二甲基甲酰胺18.2%，二甲基亚砜20%，不溶于水。pH值2～10范围内及在加热和紫外光照射下稳定，在1mol/L盐酸中煮沸6h可水解。在土壤中半衰期为49d，120d消失90%。
毒性：大鼠急性经口LD50>4640mg/kg;，急性经皮LD50>2000mg/kg，鹌鹑LD50 >2000 mg/kg ，鲤鱼LC50 (48 h) >40 ppm.，蜜蜂: LC50 (3 h) >40 ppm

作用特点及杀草谱：新型取代脲类除草剂。内吸传导型选择性取代脲类除草剂。但它与一般脲类在化学结构及作用方式上均不相同，具有以下特点：① 对莎草科杂草有特效，在发芽前1个月到发芽时用药剂进行土壤处理最好；② 无论在光照下或暗中，对敏感植物的发芽均有较强的抑制作用，它不是光合作用抑制剂；③ 它由植物根部吸收，能显著地抑制根部及地下茎的伸长，从而达到控制地上部分的生长，因此其作用迟效；④ 土壤表层处理或杂草茎叶处理无效，只有在土壤混合处理时才收到高效。适用于防除水稻、棉花、小麦、玉米、大豆、西瓜、番茄、莴苣、胡萝卜、萝卜等作物田中的许多杂草，如牛毛毡草、异型莎草、萤蔺、三棱草、香附子、扁秆藨草、两歧飘拂草等。标准用量为7 ～10kg有效成分/hm2。如防除水田三棱草与扁秆藨草，用5.0%可湿性粉剂45～150g/100m2；防除水田牛毛草，用药7.5～15g/100m2。防除旱地杂草用药量要远高于水田，并在芽前使用。

剂型：40%可湿性粉剂

生产方法 ：
一、对甲苯脲法
对甲苯脲制备 氰酸钠与对甲苯胺盐酸盐水溶液反应，控制反应温度30℃，氰酸钠稍过量，制得对甲苯脲。氰酸钠可用尿素与碳酸钠煅烧而成。
氯代异丙苯制备 2-苯基丙烯在乙腈溶剂中与氯化氢加成，侧链引入氯原子，生成氯代异丙苯。
杀草隆的合成 对甲苯脲与氯代异丙苯作用，合成杀草隆。加入对甲苯脲0.15mol，氯化异丙苯0.1mol, α-甲基苯乙烯48g及乙腈160g，于40℃搅拌反应6h，室温静置，分出结晶32g，收率80%。
二、α,α-二甲基苄基异氰酸酯法
本法是将α，α-二甲基氯苄在非水有机溶剂和金属氯化物催化剂存在下，与氰酸钠反应得α，α-二甲基苄基异氰酸酯，过滤除去副产物氯化钠，再与对甲苯胺加成制得收率良好的杀草隆。如：在反应器中加入乙酸乙酯50mL，90%氰酸钠6.5g (90mmol)，氯化锌（0.5mol)，吡啶（1mmol)，搅拌加热到50℃，然后再加入α，α-二甲基氯苄7.73g (50mmol)于50℃反应1h。制得α，α-二甲基苄基异氰酸酯。α，α-二甲基苄基异氰酸酯和对甲苯胺于甲苯或氯苯中加成，几乎得到定量收率的杀草隆。
此法反应条件缓和、收率高、原料易得、三废少，被人们推荐。

生产情况：杀草隆于1969年在日本昭和电工公司中央研究所合成,1970年由宇都宫大学竹松等人完善。国内生产企业：江苏永联集团公司江阴农药厂； 江苏省百灵农化有限责任公司；江阴凯江农化有限公司； 杭州沿山化工有限公司； 深圳市奥亨特贸易有限公司；上虞市卧龙化工有限公司；杭州安隆达化工有限公司(荆州安隆达化工有限公司)

daimuron
Herbicide
HRAC Z

NOMENCLATURE
Common name daimuron (BSI, draft E-ISO, draft (m) F-ISO); dymron (JMAF)
IUPAC name 1-(1-methyl-1-phenylethyl)-3-p-tolylurea; 1-(a,a-dimethylbenzyl)-3-p-tolylurea
Chemical Abstracts name N-(4-methylphenyl)-N'-(1-methyl-1-phenylethyl)urea
CAS RN [42609-52-9] Development codes K-223; SK-23 (SDS Biotech KK)

PHYSICAL CHEMISTRY
Mol. wt. 268.4 M.f. C17H20N2O Form Colourless, odourless needles. M.p. 203 ºC V.p. 4.53 ´ 10-4 mPa (25 ºC) KOW logP = 2.7 S.g./density 1.108 (20 ºC) Solubility In water 1.2 mg/l (20 ºC). In acetone 16, methanol 10, benzene 0.5, hexane 0.03 (all in g/l, 20 ºC). Stability Stable to heat and light. Stable between pH 4 and pH 9.

COMMERCIALISATION
History Herbicide reported by M. Tashiro (Jpn. Pestic. Inf., 1979, No. 36, 40). Introduced in Japan (1975) by Showa Denko KK (now SDS Biotech KK). Patents JP 7335454 Manufacturers SDS Biotech KK

APPLICATIONS
Biochemistry Cell division inhibitor. Mode of action Selective herbicide, absorbed mainly by the roots, with rapid translocation to the meristem. Uses Pre-emergence and early post-emergence control of cyperaceous weeds and annual grass weeds in paddy rice, at 0.3-2 kg/ha. Phytotoxicity Non-phytotoxic to rice. Formulation types GR; SC; WP. Selected products: 'Showrone' (SDS Biotech KK)

OTHER PRODUCTS
Mixtures: 'Agalia' (+ fentrazamide+ cyclosulfamuron) (Bayer CropScience, BASF); 'Award' (+ imazosulfuron+ pyributicarb) (Sumitomo Chemical Takeda); 'Batl' (+ imazosulfuron+ mefenacet) (Nihon Bayer, Sumitomo Chemical Takeda); 'Bigsure' (+ fentrazamide+ cyclosulfamuron) (Bayer CropScience, BASF); 'Crush' (+ imazosulfuron+ cafenstrole) (Sumitomo Chemical Takeda); 'Donichi' (+ fentrazamide+ imazosulfuron) (Bayer CropScience, Sumitomo Chemical Takeda, SDS Biotech KK); 'Gosign' (+ esprocarb+ imazosulfuron) (Sumitomo Chemical Takeda); 'Hayate' (+ dimethametryn+ imazosulfuron+ pretilachlor) (Sumitomo Chemical Takeda); 'Inegreen D' (+ mefenacet+ bensulfuron-methyl+ cyhalofop-butyl) (Nihon Bayer, Hokko); 'Innova GR 51' (+ fentrazamide+ bensulfuron-methyl) (Nihon Bayer); 'Innova L SC' (+ fentrazamide+ bensulfuron-methyl) (Nihon Bayer); 'Joystar' (+ bensulfuron-methyl+ cafenstrole+ cyhalofop-butyl) (Kumiai); 'Joyster' (+ bensulfuron-methyl+ cafenstrole+ cyhalofop-butyl) (Kumiai); 'Kikkubai' (+ etobenzanid+ imazosulfuron) (Hodogaya, Sumitomo Chemical Takeda, SDS Biotech KK); 'Kusa Punch' (+ pentoxazone) (Kaken); 'Kusatory Ace Jumbo' (+ bensulfuron-methyl+ cafenstrole) (Sankyo Agro); 'Nebiros' (+ cafenstrole+ cyclosulfamuron) (BASF); 'Pulgman' (+ ethoxysulfuron+ pretilachlor) (Bayer CropScience); 'Rakudar' (+ bensulfuron-methyl+ cafenstrole) (Sankyo Agro); 'Redstar' (+ halosulfuron-methyl+ cafenstrole+ cyhalofop-butyl) (Nissan); 'Tema Cut' (+ pentoxazone) (Kaken); 'The-One' (+ imazosulfuron+ pentoxazone) (Kaken, Sumitomo Chemical Takeda); 'Weedless A36' (+ azimsulfuron+ bensulfuron-methyl+ cafenstrole) (Sankyo Agro, DuPont, Eiko Kasei, SDS Biotech KK); 'Weedless' (+ bensulfuron-methyl+ cafenstrole) (Sankyo Agro); 'Zark D' (+ mefenacet+ bensulfuron-methyl) (Sankyo Agro) Discontinued products mixtures: 'Bingo' * (+ ethoxysulfuron+ anilofos+ benfuresate) (Aventis); 'Goku-Jumbo' * (+ ethoxysulfuron+ anilofos) (Aventis); 'Kimanmae' * (+ ethoxysulfuron+ anilofos) (Aventis); 'Kusatory Jumbo' * (+ pyributicarb+ bensulfuron-methyl) (Sankyo)

ANALYSIS
Product and residue analysis by hplc and glc. Details are available from SDS Biotech.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not a skin irritant. Inhalation LC50 (4 h) for rats 3250 mg/m3. NOEL (1 y) for male dogs 30.6 mg/kg diet; (90 d) for male rats 3118, female rats 3430, male mice 1513, female mice 1336 mg/kg daily. No reproductive ill-effects observed in a 2-generation study on rats. Non-teratogenic at 1000 mg/kg in rats and rabbits. ADI 0.3 mg/kg. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. LC50 (5 d) for bobwhite quail >5000 ppm. Fish LC50 (48 h) for carp >40 ppm. Daphnia LC50 (3 h) for D. pulex >40 ppm.

ENVIRONMENTAL FATE
Soil/Environment DT50 in paddy soil c. 50 d.