Sulfentrazone 磺酰唑草酮, 甲磺草胺

中文通用名称： 磺酰唑草酮
英文通用名称： sulfentrazone （ISO建议名）
商品名称： Authority(美国)、 Boral(巴西)、Capaz(拉丁美洲)
试验代号： F6285、F M C 97285
化学名称： 2',4'-二氯-5'-(4-二氟甲基-4,5-二氢-3-甲基-5-氧-1H--1,2,4-三唑-1-基)甲基
磺酰基苯胺： 2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tri-azol-1-yl)methanesulfonanilide
CA主题索引名及CAS登录号： N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tri-azol-1-yl)phenyl]methanesulfonamide
[122836-35-5]

化学结构类型： 三唑啉酮类
理化性质： 纯品为棕黄色固体；熔点121~123℃；密度1.34(20℃)；蒸气压为1.3×10-4Pa (25℃)。水中溶解度为(25℃，mg/l)：0.11(pH6)，0.78(pH7)，16(pH7.5)。可溶于丙酮和大多数极性有机溶剂。离解常数pKa=6.56。

毒性： 大鼠急性经口LD50：2855mg/kg；兔急性经皮LD50：>2000mg/kg； 本品对兔眼睛无刺激，对兔皮肤有轻微刺激但无致敏性。大鼠急性吸入LC50：4.14mg/l。野鸭急性经口LD50：>2250mg/kg；鱼毒LC50(96小时)：虹鳟>130mg/l；对水蚤 LC50(48小时)：60.4mg/l。Ames试验呈阴性。小鼠淋巴瘤和活体小鼠微核试验呈阴性。

制剂： 38.6％和48％胶悬剂，其它还有可湿性粉剂和水分散粒剂。
作用机理： 原卟啉原氧化酶抑制剂，即通过抑制叶绿素生物合成过程中原卟啉原氧化酶而引起细胞膜破坏，使叶片迅速干枯、死亡。
适宜作物： 大豆、玉米等
安全性： 对大豆、玉米、高粱、花生、向日葵等安全；对下茬禾谷类作物安全，但对棉花和甜菜有一定的药害。
防除对象： 一年生阔叶杂草、禾本科杂草和莎草如牵牛、反枝苋、铁苋菜、藜、曼陀螺、宾洲蓼、马唐、狗尾草、苍耳、牛筋草、油莎草、香附子、苍耳等，对目前较难防除的牵牛、藜、苍耳、香附子等杂草有卓效。
使用方法：
对大豆具有选择性的播后苗前土壤处理或苗后用除草剂。土壤中残效期较长，半衰期为110~280天。使用剂量为350~400克有效成分/公顷，如在大豆播种后苗前，每亩用38.6％的F6285胶悬剂70~100克加水50千克均匀喷于土然表面，或拌细潮土40~50千克施于土壤表面。

合成方法：
以2,4-二氯苯胺为起始原料，经重氮化还原制得中间体取代苯肼，再与丙酮酸缩合、与二苯基磷酰叠氮化物反应制得中间体取代的三唑啉酮；中间体取代的三唑啉酮与氯氟甲烷反应后再硝化、还原、磺酰氨化即得目的物。反应式为：

主要原料与中间体： 2,4-二氯苯胺、丙酮酸、二苯基磷酰叠氮化物、氯氟甲烷、甲基磺酰氯
分析方法： GC或HPLC
开发公司： 美国FMC公司。
专利与登记： US 5141941、E P 0370704、CN85 106905、CN86 108573、C N 1038570、CN1041513，中国专利已授权。已在我国进行了药效试验，用于大豆田防除阔叶杂草及部分禾本科杂草。

sulfentrazone
Herbicide
HRAC E WSSA 14; triazolinone

NOMENCLATURE
Common name sulfentrazone (BSI, pa E-ISO, ANSI)
IUPAC name 2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide
Chemical Abstracts name N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide
CAS RN [122836-35-5] Development codes F6285; FMC 97285

PHYSICAL CHEMISTRY
Mol. wt. 387.2 M.f. C11H10Cl2F2N4O3S Form Tan solid. M.p. 121-123 ºC V.p. 1.3 ´ 10-4 mPa (25 ºC) KOW logP = 1.48 S.g./density 1.21 g/ml (20 ºC) Solubility In water 0.11 (pH 6), 0.78 (pH 7), 16 (pH 7.5) (all in mg/g, 25 ºC). Soluble, to some extent, in acetone and other polar organic solvents. Stability Stable to hydrolysis. Readily photolysed in water.

COMMERCIALISATION
History Reported by W. A. van Saun et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1991, 1, 77). Introduced by FMC Corp.

APPLICATIONS
Biochemistry Protoporphyrinogen oxidase inhibitor (chlorophyll biosynthesis pathway). Mode of action Herbicide absorbed by the roots and foliage, with translocation primarily in the apoplasm, and limited movement in the phloem. Uses Control of annual broad-leaved weeds, some grasses and Cyperus spp. in soya beans, sugar cane and tobacco. Applied pre-emergence or pre-plant incorporated. Formulation types SC; WG. Selected products: 'Authority' (USA) (FMC); 'Boral' (Brazil) (FMC); 'Capaz' (Latin America) (FMC)

OTHER PRODUCTS
'Cover' (DuPont) mixtures: 'Authority BL' (+ metribuzin) (FMC); 'Authority Broadleaf' (+ chlorimuron-ethyl) (FMC); 'Authority One-Pass' (+ clomazone) (FMC); 'Command Xtra' (+ clomazone) (FMC); 'Gauntlet' (+ cloransulam-methyl) (FMC); 'Canopy XL' (+ chlorimuron-ethyl) (DuPont) Discontinued products: 'Spartan' * (FMC)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 2855 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritating to skin; mild eye irritant (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >4.14 mg/l. NOEL 10 mg/kg daily (rat teratology study). Other Non-mutagenic in the Ames test, mouse lymphoma and in vivo mouse micronucleus assay. Toxicity class EPA (formulation) III

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >2250 mg/kg. Dietary LC50 (8 d) for ducks and quail >5620 mg/kg. Fish LC50 (96 h) for bluegill sunfish 93.8, rainbow trout >130 mg/l. Daphnia LC50 (48 h) 60.4 mg/l.

ENVIRONMENTAL FATE
Animals In rats, nearly all of administered sulfentrazone is excreted in the urine within 72 h. Plants In soya beans, over 95% of the parent sulfentrazone is metabolised to the non-polar, ring-hydroxymethyl analogue within 12 hours. This analogue is also rapidly converted, over the same time period, to three polar metabolites, two of which are glycosidic derivatives and one a non-glycoside metabolite. Soil/Environment Stable in soil (DT50 18 mo). In water, stable to hydrolysis (pH 5-9), but readily undergoes photolysis (DT50 <0.5 d). Low affinity for organic matter (Koc 43), but is mobile only in soils with high sand content. Low potential to bioaccumulate.