(R)-butyl 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propanoate
cyhalofop butyl ester
CAS: 122008-85-9
Molecular Formula: C20H20FNO4
(R)-butyl 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propanoate - Names and Identifiers
(R)-butyl 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propanoate - Physico-chemical Properties
| Molecular Formula | C20H20FNO4 |
| Molar Mass | 357.38 |
| Density | 1.21±0.1 g/cm3(Predicted) |
| Melting Point | 47.0 to 51.0 °C |
| Boling Point | 449.1±45.0 °C(Predicted) |
| Flash Point | 122℃ |
| Solubility | soluble in Methanol |
| Vapor Presure | 2.94E-08mmHg at 25°C |
| Appearance | neat |
| Color | White to Almost white |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.55 |
| Physical and Chemical Properties | White solid crystal, melting point 50 ℃, vapor pressure: 1.2x 10-3MPa (20 ℃), lipophilic hydrophilic equilibrium constant KowlogP = 3.31, water solubility of 0.7 pp m(pH 7,20 degrees C). Stability: stable at pH 4, slow decomposition at pH 7, and rapid decomposition at pH 1.2 or pH 9. The physical and chemical properties, mechanism of action, and application of cyanfluoroxylate were edited by Ding Hong. (2015-12-21) |
(R)-butyl 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propanoate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50 - Very Toxic to aquatic organisms |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| HS Code | 29269090 |
| Hazard Class | 9 |
| Packing Group | III |
(R)-butyl 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)propanoate - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Cyanflurane (cyhalofop-butyl) is an oxyphenoxypropionic acid type newly developed by DowElanw Co.Ltd. The herbicide, the trade name is Qianjin (Clincher), the code name is XED-537, the chemical name is (R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] butyl propionate, which is mainly used in rice seedling fields, direct seeding fields, and transplanting fields to prevent and remove barnyard grass Most of the malignant gramineous weeds such as gold, beef tendon grass, etc., and can effectively control weeds that are resistant to quinclorac, sulfonylurea and amide herbicides. It has the characteristics of high efficiency, low toxicity and low residue. |
| mechanism of action | through rapid conduction in the plant body, and rapid degradation into a series of metabolites: cyanofluoroxalic acid (ACID), cyanofluoroxalide (AMIDE), cyanofluoroxalic acid (DIACID) and cyanofluoroxalol (DP), where ACID is a compound with herbicidal activity. ACID can effectively inhibit the enzyme acetyl-CoA carboxylase, which is necessary for the biosynthesis of fatty acids in the body, by accumulating in the intermediary meristem of weeds. |
| preparation method | 1. intermediate (A)4-oxo-(2 '-fluoro -4'-cyanophenoxy) phenol is generated by the reaction of 3,4-difluorobenzonitrile and excess hydroquinone. fig. 1 is a roadmap for the synthesis of intermediate (a), of which 3,4-difluorobenzonitrile is available on the market, but the price is relatively high, it can be prepared by the following reaction: Figure 2 is the road map for the synthesis of 3,4-difluorobenzonitrile. After the reaction of (S) butyl lactate and excess 4-methylbenzenesulfonyl chloride, the configuration is reversed to generate intermediate (B)(R) -2-oxo-(4 '-methylbenzenesulfonyl)-butyl propionate: fig. 3 is a road map for the synthesis of intermediate (B) 4-oxygen-one (2-fluoro-4-cyanophenoxy) hydroquinone (a) and (r) -2-oxygen-one (4'-methyl benzenesulfonyl)-butyl propionate (B) reaction, the configuration does not reverse, and the product is cyanofluoroxazole. Fig. 4 is a route for the synthesis of cyanflurate |
| stability | cyfluoxalate is relatively stable under acidic conditions, and the hydrolysis speed is accelerated under slightly acidic and neutral conditions. Under strong alkaline conditions, cyfluoxalate hydrolyzes rapidly; in the range of 25 ℃ ~ 65 ℃, with the increase of temperature, the hydrolysis speed of cyfluoxalate accelerates, the degradation rate at 25 ℃(pH 5.0) is only 14% of that at 65 ℃. ACID is relatively stable under acidic and neutral conditions. It hydrolyzes slowly under weak alkali conditions. Only under strong alkali conditions can hydrolyze faster. Increasing the temperature can accelerate its hydrolysis. When it rises from 25 ℃ to 35 ℃, The hydrolysis rate constant k increases about 1~2 times. |
| Degradation | Microorganisms in water can effectively promote the degradation of cyanflurinate, which has a certain stimulating effect on the growth of some bacteria in the pool water, but has no obvious effect on the growth of actinomycetes and fungi. Through the culture and identification of different species of bacteria, it is found that the degrading microorganisms of cyflufon in pond water are mainly Pseudomonas and Staphylococcus, and the metabolic mechanism may be mainly growth and metabolism. In summary, the results of studies on the degradation of cyfluoxalate indoors and outdoors show that cyfluoxalate degrades rapidly in the natural environment, has a short residue period, and does not pose a threat to the safety of rice and its environment when applied at conventional concentrations; the fate of cyfluoxalate in rice field ecosystems can be multiple pathways, but mainly biodegradation and photolysis, followed by hydrolysis; the environmental and ecological toxicities of the biological safety of cyflufon and a series of its degradation products need further research. |
| application | is mainly used in rice seedling fields, direct seeding fields and transplanting fields to control most malignant gramineous weeds such as barnyard grass, thousand gold and beef tendon grass, and can effectively control weeds resistant to quinclorac, sulfonylurea and amide herbicides. |
| References | [1] Zhugenlin. Chemical-Enzymatic Chiral Synthesis of Cyanfluroxate [D]. Hefei University of Technology, 2012. [2] Zhang Jixu, Zheng Babbler, Wang Jianfeng, Luo Shuping, Xu Danqian. Synthesis of Herbicide Cyanflurinate [J]. Pesticide, 2010,49(05):329-331 337. [3] Zhao Li, Fan Xiaoqing, Zhu Guonian. Study on Hydrolysis Kinetics of Cyanflurinate [J]. Journal of Pesticide Science, 2009,11(02):274-278. [4] Zhao Li. Study on Degradation of Cyanfluorosin in Rice Field Ecosystem [D]. Zhejiang University, 2001. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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