Fluometuron 伏草隆

伏草隆

英文通用名 fluometuron
其他名称 棉花伏(Cotoran)、高度蓝，Lanex，C2059。
分子式： C10H11F3N2O
毒性 对人畜低毒。大白鼠急性口服LD50>8000毫克/公斤，对兔眼睛和皮肤有轻微刺激作用。慢性毒性试验未发现异常。
剂型 50%、80%可湿性粉剂、20%粉剂。
特点 为内吸选择性土壤处理使用除草剂。主要通过杂草根吸收，叶部活性底。对1年生禾本科和阔叶杂草均有效。持效期长、棉田使用1次即能防除整个生育期内的杂草。

适用范围
适用于棉花、玉米、甘蔗、马铃薯等作物田以及果园防除稗草、马唐、狗尾草、千金子、蟋蟀草、看麦娘、早熟禾、繁缕、龙葵、小旋花、马齿苋、铁苋菜、藜、碎米荠等1年生禾本科杂草和阔叶杂草。

生产方法：
由间氨基三氟甲苯与光气反应制备间三氟甲苯异氰酸酯，再与二甲胺反应得到伏草隆。1.间三氟甲苯异氰酸酯的制备将光气通入甲苯中，吸收一部分光气后，一面继续通光气，一面滴加间氨基三氟甲苯的甲苯溶液。滴完后将温度缓缓升到75℃左右，继续通光气至反应液变清时为止。继续搅拌30min，迅速升温至100℃左右，通干燥空气赶除过剩的光气和反应产生的氯化氢气体，得间三氟甲苯异氰酸酯[392-01-1]的甲苯溶液。2.伏草隆的制备将上述间三氟甲苯异氰酸酯甲苯溶液加入合成锅中，搅拌，控制温度在50℃左右，滴加二甲胺。滴完后保持反应1h，终点时反应液的pH值稳定在7.5-8。静置后甩滤，在80-90℃干燥，得伏草隆原粉，含量在95%以上，收率约92%。

使用方法

1.棉田使用 播种后4-5天出苗前，每亩用80%可湿性粉剂100-125克，对水50公斤，均匀喷布土表。棉花苗床使用，于播种覆土后，每亩用80%可湿性粉剂75-100克，对水35公斤均匀喷布土表，喷雾后盖薄膜。
2.玉米田使用 玉米播种后出苗前，每亩用50%可湿性粉剂100克，对水50公斤均匀喷布土表。亦可在玉米喇叭口期，中耕除草后，每亩用80%可湿性粉剂100克，对水35公斤定向喷布行间土表，切勿喷到叶片上。
3.果园使用 每亩用80%可湿性粉剂100克，加50%莠去津150克，对水50公斤，均匀喷布土表。然后进行线层混土或灌水，使药剂渗入土壤，提高药效。

注意事项

1.棉花出苗后禁用。玉米出苗后，果园用药，切勿将药液喷到幼芽及叶片上，以免产生药害。
2.在沙质土壤中使用应适当减少用药量。
3.喷雾器具使用后要清洗干净。

fluometuron
Herbicide
HRAC C2, also F3 WSSA 7, also 13; urea

NOMENCLATURE
Common name fluometuron (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 1,1-dimethyl-3-(a,a,a-trifluoro-m-tolyl)urea
Chemical Abstracts name N,N-dimethyl-N'-[3-(trifluoromethyl)phenyl]urea
CAS RN [2164-17-2] EEC no. 218-500-4 Development codes C 2059 (Ciba)

PHYSICAL CHEMISTRY
Mol. wt. 232.2 M.f. C10H11F3N2O Form White crystals. M.p. 163-164.5 ºC V.p. 0.125 mPa (25 ºC); 0.33 mPa (30 ºC) (OECD 104) KOW logP = 2.38 S.g./density 1.39 at 20 ºC Solubility In water 110 mg/l (20 ºC). In methanol 110, acetone 105, dichloromethane 23, n-octanol 22, hexane 0.17 (all in g/l, 20 ºC). Stability Stable in acidic, neutral, and alkaline media at 20 ºC. Decomposed by u.v. irradiation.

COMMERCIALISATION
History Herbicide reported by C. J. Counselman et al. (Proc. South Weed Conf., 17th, 1964, 189). Introduced by Ciba AG (now Syngenta AG) and first marketed in the early 1970s. Divested to Makhteshim-Agan in 2001. Patents BE 594227; GB 914779 Manufacturers ÉMV; Griffin; Makhteshim-Agan; Nufarm GmbH; Sannong

APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Also inhibits carotenoid biosynthesis; target enzyme not known. Mode of action Selective systemic herbicide, absorbed more readily by the roots than by the foliage, with translocation acropetally. Uses Control of annual broad-leaved weeds and grasses in cotton and sugar cane, at 1.0-1.5 kg/ha. Phytotoxicity Phytotoxic to sugar beet, beetroot, soya beans, french beans, brassicas, tomatoes, legumes, cucurbits, aubergines, and several other crops. Formulation types SC; WP. Selected products: 'Cotoran' (Makhteshim-Agan); 'Flomet' (Micro Flo); 'Meturon' (Griffin); mixtures: 'Cotolina' (+ trifluralin) (Aragro); 'Cottonex Pro' (+ prometryn) (Aragro)

OTHER PRODUCTS
'Cotolint' (Nufarm GmbH); 'Cottonex' (Makhteshim-Agan) mixtures: 'Bandit' (+ prometryn) (Crop Care); 'Command Cotton' (+ clomazone) (FMC); 'Cotogard' (+ prometryn) (Makhteshim-Agan); 'Cottonex Com' (+ trifluralin) (Makhteshim-Agan); 'Cottonex D' (+ diuron) (Makhteshim-Agan); 'Cottonex P' (+ prometryn) (Makhteshim-Agan); 'Cottonex PG' (+ glyphosate-isopropylammonium+ prometryn) (Makhteshim-Agan); 'Croak' (+ MSMA) (Drexel); 'Double Team' (+ prometryn) (Makhteshim-Agan)

ANALYSIS
Product analysis by glc (AOAC Methods, 17th Ed., 977.07; CIPAC Handbook, 1983, 1B, 1842) or by hplc (G. W. Sheehan & A. Sobolewski, Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 241). Residues determined by hydrolysis to a,a,a-trifluoro-m-toluidine, a derivative of which is measured by glc with ECD (G. Voss et al., ibid., 1973, 7, 569). In water, by lc with u.v. detection (AOAC Methods, 17th Ed., 992.14).

MAMMALIAN TOXICOLOGY
IARC ref. 30 class 3 Oral Acute oral LD50 for rats >6000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000, rabbits >10 000 mg/kg. Mild skin and eye irritant (rabbits). Not a skin sensitiser. NOEL (2 y) for rats 19, mice 1.3 mg/kg b.w. daily; (1 y) for dogs 10 mg/kg b.w. daily. ADI 0.013 mg/kg b.w. Toxicity class WHO (a.i.) U; EPA (formulation) II

ECOTOXICOLOGY
Birds LD50 for mallard ducks 2974 mg/kg. Dietary LC50 (8 d) for Japanese quail 4620, mallard ducks 4500, ring-necked pheasants 3150 mg/kg diet. Fish LC50 (96 h) for rainbow trout 30, bluegill sunfish 48, catfish 55, crucian carp 170 mg/l. Daphnia LC50 (48 h) 10 mg/l. Algae EC50 (3 d) 0.16 mg/l. Bees LD50 (oral) >155 mg/bee; (topical) >190 mg/bee. Worms LC50 (14 d) for earthworms >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals In rats, mainly formation of demethylated metabolites and some conjugation with gluconuronic acid. Elimination, mainly in the urine, was 96% within one week. Plants In plants, degraded by a three-step process, first demethylation to a monomethyl, then to a demethylated intermediate, and finally deamination-decarboxylation to an aniline derivative. Soil/Environment In soil, microbial degradation is significant and rapid, with continual liberation of CO2. Photodecomposition and volatilisation are insignificant. It is moderately leachable in all but very sandy soils: Koc 31-117 (8 soil types); Kd 0.15-1.13. Median DT50 in soil c. 30 d; depending on environmental factors, range was 10 to almost 100 d; dry conditions reduce breakdown.