Fluoroglycofen-ethyl 乙羧氟草醚

乙羧氟草醚

CAS号: 77501-90-7

英文名称：Fluoroglycofen

化学名称：0-[5-(2-氯-a,a,a-三氟-对-甲苯氧基)-2-硝基苯甲酰基]羟基乙酸乙酯；5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitro-benzoicaci2-ethoxy-2-ox

其他名称：阔锄，克草特，Compete、RH-0264

分子式：C18H13ClF3NO7

分子量：447.75

结构式：

理化性质：琥珀色固体。密度：1.01，熔点65℃。蒸气压：小于133（25℃），25℃在水中的溶解度<1mg/L，易溶于大多数有机溶剂中。在大多数有机溶剂中溶解度大于100g/kg。其水悬浮液因紫外光而迅速分解。土壤中因微生物而迅速降解，DT50约11h。

毒性：对人畜低毒。大鼠急性口服LD501500毫克/公斤，兔急性经皮LD50＞5000毫克/公斤。对皮肤和眼睛有轻度刺激作用。对鸟类低毒。对鱼类低毒。对某些鱼的LC50约为0.001～0.002mg/L。无慢性毒性问题。蜜蜂急性接触LD50(96h)大于0.1mg(a.i.)/蜜蜂。

作用特点及用途：本品属二苯醚类除草剂，是原卟啉氧化霉抑制剂，本品一旦被植物吸收，只有在光照条件下才发挥效力。该化合物同分子氯反应，生成对植物细胞具有毒性的化合物四吡咯，积聚而发生作用。积聚过程中，使植物细胞膜完全消失，然后引起细胞内含物渗漏。

本品芽后使用防除阔叶杂草，所需剂量相对较低。虽然该药剂芽前施用对敏感的双子叶杂草也有一定活性，但剂量必须高于芽后剂量的2-10倍。该药剂防除窄叶或多年生杂草无效。

适用于小麦、大麦、花生、大豆和稻田除草。可防除阔叶杂草和禾本科杂草，尤其是独殃殃、婆婆纳、堇菜、苍耳属和甘薯杂草。每公顷使用有效成分30-40克，对水喷雾作芽前或芽后使用。

剂型：10%乳油，20%苯磺隆·乙羧氟草醚可湿性粉剂

生产方法：3,4-二氯三氟甲基苯与间羟基苯甲酸反应，得到3-（2-氯-4-（三氟甲基）苯氧基）苯甲酸，该化合物经硝化得到5-（2－氯－4－（三氟甲基）苯氧基）-2-硝基苯甲酸，最后与α-氯代乙酸乙酯在碳酸钾存在下于二甲基亚矾中反应，即制得产品。

生产情况：四川省化学工业研究设计院；山东神星药业有限公司；淄博新农基农药化工有限公司；石家庄济泰三沐农药化工有限
公司；青岛瀚生生物科技股份有限公司

fluoroglycofen-ethyl
Herbicide
HRAC E WSSA 14; diphenyl ether

NOMENCLATURE
fluoroglycofen-ethyl
Common name fluoroglycofen-ethyl
CAS RN [77501-90-7] Development codes RH-0265 (Rohm & Haas)

fluoroglycofen
Common name fluoroglycofen (BSI, ANSI, draft E-ISO); fluoroglycofène ((m) draft F-ISO)
IUPAC name O-[5-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-nitrobenzoyl]glycolic acid
Chemical Abstracts name carboxymethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate
CAS RN [77501-60-1]

PHYSICAL CHEMISTRY
fluoroglycofen-ethyl
Mol. wt. 447.8 M.f. C18H13ClF3NO7 Form Dark amber solid. M.p. 65 ºC KOW logP = 3.65 S.g./density 1.01 (25 ºC) Solubility In water 0.6 mg/l (25 ºC). Readily soluble in most organic solvents (except hexane). Stability In aqueous solution, 0.25 mg/l, at 22 ºC, DT50 c. 231 d (pH 5), 15 d (pH 7), 0.15 d (pH 9); aqueous suspensions are rapidly decomposed by u.v. light.

fluoroglycofen
Mol. wt. 419.7 M.f. C16H9ClF3NO7

COMMERCIALISATION
History Herbicide developed by Rohm & Haas Co. (now Dow AgroSciences) as the ethyl ester. Manufacturers Dow AgroSciences

APPLICATIONS
fluoroglycofen-ethyl
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Fluoroglycofen-ethyl is a selective leaf- and root- herbicide. Uses Post-emergence control of broad-leaved weeds and grasses (particularly Galium, Viola, and Veronica spp.) in wheat, barley, oats, peanuts, rice, and soya beans. Formulation types EC; WP. Compatibility Incompatible with suspension concentrate formulations. Selected products: mixtures: 'Satis' (+ triasulfuron) (Syngenta)

OTHER PRODUCTS
fluoroglycofen-ethyl
'Compete' (Dow AgroSciences) mixtures: 'Presto' (+ metosulam) (Dow AgroSciences, Bayer CropScience); 'Estrad' (+ dichlorprop-P) (magnesium/sodium salt) (BASF); 'Kuorum' (+ isoproturon) (Bayer CropScience) Discontinued products mixtures: 'Competitor' * (+ isoproturon) (AgrEvo, Stefes)

ANALYSIS
Product by glc. Residues by glc with halogen-specific MCD. Details from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
fluoroglycofen-ethyl
Reviews UK MAFF Scientific Sub-committee on Pesticides, Disclosure Document for Fluoroglycofen-ethyl, Feb. 1992. Oral Acute oral LD50 for rats 1500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg; slight irritant to their skin and eyes. Inhalation LC50 (4 h) for rats >7.5 mg EC formulation/l. NOEL (1 y) for dogs 320 mg/kg diet. ADI 0.009 mg/kg. Other Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) III

ECOTOXICOLOGY
fluoroglycofen-ethyl
Birds Acute oral LD50 for bobwhite quail >3160 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 mg a.i./kg. Fish LC50 (96 h) for bluegill sunfish 1.6, trout 23 mg/l. Daphnia LC50 (48 h) 30 mg/l. Bees LD50 (contact) >100 mg/bee.

ENVIRONMENTAL FATE
Animals Hydrolysis of the ester and reduction of the nitro group. Plants As for animals. Soil/Environment In soil and water, fluoroglycofen-ethyl is very rapidly hydrolysed to the corresponding acid. In soil, microbial degradation follows; DT50 (to acifluorfen) c. 11 h. Koc 1364, DT50 7-21 d (F. E. Dayan & S. O. Duke, Proc. Br. Crop Prot. Conf. - Weeds, 1997, 1, 83).