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虫螨腈
除尽 · 虫螨腈 · 溴虫腈 · 吡咯胺 · 溴虫睛 · 虫螨腈原药 · 4-溴吡咯 · 虫螨腈溶液
标识与物理属性
| CAS No. | 122453-73-0 |
|---|---|
| 分子式 | C15H11BrClF3N2O |
| 平均分子量 | 407.61 g/mol |
| 单同位素质量 | 405.96953741 g/mol |
| SMILES | CCOCn1c(-c2ccc(Cl)cc2)c(C#N)c(Br)c1C(F)(F)F |
| InChIKey | CWFOCCVIPCEQCK-UHFFFAOYSA-N |
| PubChem CID | 91778 |
| ChEMBL | CHEMBL1869551 |
| ChEBI | CHEBI:39347 |
| EC No. | 602-782-4 |
| DTXSID | DTXSID9032533 |
| 中文名 | 虫螨腈 |
化学与物理性质
| XLogP | 4.5 |
|---|---|
| 极性表面积 | 38 |
| 氢键供体 | 0 |
| 氢键受体 | 5 |
| 可旋转键 | 4 |
| 重原子 | 23 |
| 形式电荷 | 0 |
| 复杂度 | 448 |
| pH | pH = 7.161% aqueous slurry at 24 °C |
| 农药 | Acaricides, InsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Other InsecticidesPesticide (Chlorfenapyr) -> USDA PDB |
| LogP（油水分配系数） | log Kow = 4.83 |
| 气味 | Characteristic of halides and ketones |
| 密度 | 0.543 g/ml tapped bulk density1.53±0.1 g/cm3(Predicted) |
| Color/Form | Light tan or light yellow powdered solidWhite solid |
| 溶解性 | Soluble in acetone, diethyl ether, DMSO, THF, acetonitrile, alcohols. Insoluble in waterSolubities at 25 °C. [Table#7120]Solubities in water at 25 °C. [Table#7121]Insoluble in waterDMSO: 250 mg/mL (613.33 mM) |
| Decomposition | When heated to decomposition it emits toxic vapors of /hydrogen chlorid, hydrogen fluoride, and nitrogen oxides/. |
| 熔点 | 100-101 °CMP: 91-92 °C91-92° |
| 蒸气压 | 0.00000007 [mmHg] |
| Physical Description | White solid[Merck Index] Light tan or light yellow solid[HSDB] White solid[MSDSonline] |
| Collision Cross Section | 177.74 Ų [M+H]+ [CCS Type: TWBuffer gas: N2Ionization: GC-APCI+]190.4 Ų [M+HCOO]- |
| 沸点 | 443.5±45.0 °C(Predicted) |
| 储存条件 | Sealed in dry,2-8°C |
| pKa（酸度系数） | -18.00±0.70(Predicted) |
| 形态 | Solid |
| 颜色 | White to Almost white |
| BRN | 6940152 |
| 亨利常数 | 1.7×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 主要应用 | agricultureenvironmental |
| InChI | InChI=1S/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3 |
| InChIKey | CWFOCCVIPCEQCK-UHFFFAOYSA-N |
| SMILES | N1(COCC)C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 |
| CAS 数据库 | 122453-73-0(CAS DataBase Reference) |
| NIST化学物质信息 | Chlorfenapyr(122453-73-0) |
| EPA化学物质信息 | Chlorfenapyr (122453-73-0) |
化学性质
纯品为白色固体。m.p.91～92℃(100～101℃)，能溶于丙酮、乙醚、二甲亚砜、四氢呋喃、乙腈、醇类等有机溶剂，不溶于水。
安全与法规
| GHS 分类 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P273, P301+P317, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 法规信息 | Chlorfenapyr is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2001/697/ECChlorfenapyr: HSNO Approval: HSR006718 Approved with controls |
| 危害概述 | A moderate eye irritant[HSDB] The active metabolite uncouples oxidative phosphorylation in the mitochondria causing cellular death[Reference #1] In high-dose animal studies, causes liver changes, depressed activity and ataxia[RTECS] A mild skin and eye irritant based on animal studies[MSDSonline] |
| FIFRA 要求 | Tolerances are established for residues of the insecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile] in or on the following raw agricultural commodities: vegetables, fruiting, group 8.A tolerance is established for residues of chlorfenapyr in or on all food commodities (other than those covered by a higher tolerance as a result of use on growing crops) in food/feed handling areas where food/feed products are prepared, held, processed, or served and in accordance with the following prescribed conditions: (i) Application shall be no greater than a 0.5% active ingredient solution for spot crack and crevice use in food/feed handling establishments, where food and food products are held, processed, prepared and/or served. (ii) Application may only be undertaken when the facility is not in operation, and provided exposed food has been covered, or removed from the area being treated prior to application. (iii) Food contact surfaces and equipment should be throughly washed with an effective cleaning compound, and rinsed with potable water after each use of the product. (iv) Contamination of food or food contact surfaces shall be avoided. Application excludes any direct application to any food, food packaging, or any food contact surfaces. (v) To assure safe use, the label and labeling shall conform to that registered by the U.S. Environmental Protection Agency, and it shall be used in accordance with such label and labeling.Under the authority of Section 3(c)(5), the Agency has determined that the database supports granting an unconditional registration for Chlorfenapyr Technical, and for Pylon Miticide-Insecticide (21.4% chlorfenapyr), for use on ornamentals grown in commercial greenhouses. |
| DOT Emergency Guidelines | /GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Health: TOXICinhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Poisonous solid, organic, NOSToxic solid, organic, NOS (Chlorfenapyr)//GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. /Poisonous solid, organic, NOS/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Poisonous solid, organic, NOS/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible. /Poisonous solid, organic, NOSFor more DOT Emergency Guidelines (Complete) data for CHLORFENAPYR (8 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity - category 3Acute toxicity (Oral) - Category 4Acute Tox. 3 * |
| Explosive Limits and Potential | Not explosive |
| Skin, Eye, and Respiratory Irritations | Chlorfenapyr is a moderate but reversible eye irritant, but not a skin irritant. |
| 灭火程序 | Use water, alcohol foam, dry chemical, or carbon dioxide to extinguish fires. |
| 储存条件 | Do not store below 32 °F. ... Store in a secure, dry, ventilated area away from children, livestock, and food. Do not store in direct sunlight or heat.Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. |
| 清理方法 | If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. |
| 处置方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Do not contaminate water, food, or feed by disposal.Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. |
| Preventive Measures | Do not get in eyes, on skin, or clothing. Avoid breathing vapor or mist. Harmful if inhaled. Wash thoroughly after handling with soap and water.Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracksdon't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Allowable Tolerances | Tolerances are established for residues of the insecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile] in or on the following raw agricultural commodities: vegetables, fruiting, group 8, 1.0 ppm.A tolerance of 0.01 parts per million is established for residues of chlorfenapyr in or on all food commodities (other than those covered by a higher tolerance as a result of use on growing crops) in food/feed handling areas where food/feed products are prepared, held, processed, or served and in accordance with the following prescribed conditions: (i) Application shall be no greater than a 0.5% active ingredient solution for spot crack and crevice use in food/feed handling establishments, where food and food products are held, processed, prepared and/or served. (ii) Application may only be undertaken when the facility is not in operation, and provided exposed food has been covered, or removed from the area being treated prior to application. (iii) Food contact surfaces and equipment should be throughly washed with an effective cleaning compound, and rinsed with potable water after each use of the product. (iv) Contamination of food or food contact surfaces shall be avoided. Application excludes any direct application to any food, food packaging, or any food contact surfaces. (v) To assure safe use, the label and labeling shall conform to that registered by the U.S. Environmental Protection Agency, and it shall be used in accordance with such label and labeling. |
| Personal Protective Equipment (PPE) | Chemical-resistant apron when cleaning equipment, mixing, or loading. Chemical resistant gloves. |
| Treatment | Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97) |
| 相互作用 | Inhibition of /microsomal/ oxidative activation /of chlorfenapyr/ ... in insects in vivo with piperonyl butoxide antagonizes the toxicity of chlorfenapyr. |
| 健康影响 | Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97) |
| 生态毒性数值 | LC50Species: Daphnia sppConcentration: 6.1 ppb/24 to 96 hrConditions: not specified /From table/LD50 /Colinus virginianus/ (Northern bobwhite) oral 34 mg/kg (95% confidence interval 24-49 mg/kg) /from table/LD50 /Anas platyrhynchos/ (Mallard duck) oral 10.3 mg/kg (95% confidence interval 7.0-15.1 mg/kg) /from table/LD50 /Agelaius phoeniceus/ (Red-winged blackbird) oral 2.2 mg/kg (95% confidence interval 1.5-4.0 mg/kg) /from table/For more Ecotoxicity Values (Complete) data for CHLORFENAPYR (7 total), please visit the HSDB record page. |
| 环境归趋 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10,000(SRC), determined from a log Kow of 4.83(2) and a regression-derived equation(3), indicates that chlorfenapyr is expected to be immobile in soil(SRC). Volatilization of chlorfenapyr from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Chlorfenapyr is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-8 mm Hg(SRC), determined from a fragment constant method(5). A biodegradation half-life range of 230-250 days in soil(6) suggest that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10,000(SRC), determined from a log Kow of 4.83(2) and a regression-derived equation(3), indicates that chlorfenapyr is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). BCFs of 83-114 given for bluegill sunfish(5), suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Photolysis is expected to be the principal fate of chlorfenapyr in water(5). A biodegradation half-life of 250 days in sediment(5) suggest that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorfenapyr, which has an estimated vapor pressure of 7.4X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorfenapyr is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 1.2 days(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase chlorfenapyr may be removed from the air by wet or dry deposition(SRC). Chlorfenapyr photodegrades in sterile fresh water with a half-life of 5-7 days(4), suggesting that photolysis in air may be important(SRC). |
| 食品调查数值 | Chlorfenapyr was detected in 10 of 129 sweet peppers tested, at concentrations of <0.5 ug/g, sampled from Hyogo Prefecture, Japan(1). |
| 不良影响 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 暴露途径 | Oral (L96)inhalation (L96)dermal (L96) |
| 毒性概述 | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) |
| 生态毒性摘录 | /BIRDS and MAMMALS/ The acute toxicity of chlorfenapyr to birds is high to very high. The subchronic toxicity to birds is also very high (eg, in mallard ducks, chlorfenapyr at 2.5 ppm in the diet reduced adult body weights and decr egg-laying and hatch rates by about 40 to 60%) ... Although /lab/ results suggest that there is a considerable potential for the use of chlorfenapyr to cause acute and reproductive toxicity in wild birds, there appear to be no reports of detectable impacts on birds or other wildlife when these have been closely monitored in areas where chlorfenapyr has been used./AQUATIC SPECIES/ Chlorfenapyr is also very highly toxic to fish and aquatic invertebrates /with LC50 for fish ranged 7.4 to 500 ppb/24 to 96 hr/ .../BIRDS and MAMMALS/ Clinical signs of intoxication /in acute studies/ common to all three species included whole body and wing beat convulsions, lethargy and loose green or chalky excreta. In addition, dyspnea (labored breathing) and opisthotonos (head stretched over back) were reported for the mallard. Lethargy was reported in the highest red-winged blackbird dose group. Post-mortem exam showed no treatment related abnormalities other than firm pectoral muscles. A reduction in body weight, as compared to the control animals, occurred in the northern bobwhite at dose levels above 32 mg/kg during the first 3 days of the study. No body weight reduction was noted in the mallards or red-winged blackbirds. A reduction in food consumption, as compared to the control animals, occurred in the northern bobwhite at dose levels above 16 mg/kg during the first 3 days of the study. A similar response was observed in the mallard at treatments higher than 4 mg/kg. These results indicate that chlorfenapyr is very highly toxic to waterfowl and passerine species and highly toxic to upland gamebirds on an acute oral basis./BIRDS and MAMMALS/ AC 303,268, a soil photolytic degradate, was shown to kill nearly as quickly as the parent compound and was more toxic to northern bobwhite. Deaths prior to day 4 accounted for 88% of the total mortality observed in mallards and northern bobwhite. Weight loss coincided with decreased food consumption at day 3 at treatment groups 40 mg/kg and higher in the mallard and at 25 mg/kg and higher in the northern bobwhite. Signs of intoxication common to both species included shallow rapid breathing, reduced reaction time, and loss of coordination. Necropsy showed small pale yellow spleens and stained vents. /AC 303,268soil degradate/For more Ecotoxicity Excerpts (Complete) data for CHLORFENAPYR (9 total), please visit the HSDB record page. |
| Signs and Symptoms | Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97) |
| Soil Adsorption/Mobility | The Koc of chlorfenapyr is estimated as 10,000(SRC), using a log Kow of 4.83(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chlorfenapyr is expected to be immobile in soil. |
| 水危害等级（WGK） | 3 |
| 毒性 | LD50 (single dose) in male, female rats (mg/kg): 223, 459 orallyin rabbits: >2000 dermally (Lovell)LC50 in Japanese carp: 0.5 ppm (Lovell) |
| 储存类别 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 安全说明（S） | 13-36/37-45-60-61 |
| 海关编码 | 2933.99.1701 |
| 危险品标志 | TN,N,T |
| 危险类别 | Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
| 危险类别码（R） | 22-23-50/53 |
| 毒害物质数据 | 122453-73-0(Hazardous Substances Data) |
| 运输编号（UN） | UN 2811 |
用途与应用
简介
虫螨腈又叫溴虫腈，属芳基吡咯类化合物，对害虫具有胃毒和一定的触杀作用及内吸活性；是由美国氰胺公司于1985年从链霉菌属真菌的代谢产物中分离出的二恶吡咯霉素的基础上开发成功的一种杀虫、杀螨、杀线虫剂。对钻蛀、刺吸式口器害虫和害螨的防效优异，持效期中等，其杀虫机理是阻断线粒体的氧化磷酰化作用。
用途
结构新型的吡咯类杀虫、杀螨剂。对钻蛀、刺吸和咀嚼式害虫及螨类有优良的防效。比氯氰菊酯和氟氰菊酯更有效，其杀螨活性比三氯杀螨醇和三环锡强。该药剂具有以下特征：广谱性杀虫、杀螨剂；兼有胃毒和触杀作用；与其他杀虫剂无交互抗性；在作物上有中等残留活性；在营养液中经根系吸收有选择性内吸活性；对哺乳动物经口毒性中等，经皮毒性较低；有效施药量低（100g有效成分/hm2)。其显著的杀虫、杀螨活性和独特的化学结构受到人们广泛的重视和关注。
制备与合成方法
生产方法
2-（对氯苯基）肌氨酸的制备 将88g甲胺盐酸盐水溶液、53gNaCN水溶液，加入到153g对氯苯甲醛的四氢呋喃溶液中。室温搅拌16h。用甲苯抽提，往甲苯层中加入10mL吡啶，接着加入50mL醋酐。室温搅拌，真空浓缩得油状物加到1：1的水和盐酸的混合物中。加热回流2h，冷却，用水稀释，用50%的氢氧化钠溶液中和至pH值2，有固体沉淀。过滤，空气干燥，得白色固体180g。m.p.208～213℃。2-(对氯苯基）-N-（三氟乙酰基）肌氨酸的制备 将27g的2-（对氯苯基）肌氨酸溶于无水甲苯中，用20mL三氟醋酸酐处理，搅拌反应1h，真空浓缩得固体残留物。用甲苯重复汽化残留物几次，得红色固体38.7g。m.p.117～118℃。2-（对氯苯基）-1-甲基-5-（三氟甲基）-2-吡咯啉-3-腈的制备 于7.4g 2-（对氯苯基）-N-（三氟甲基）肌氨酸的乙腈溶液中，加入醋酸酐5.1g、丙烯腈1.6g和10滴三乙胺，在回流下加热反应5.5h，冷却，真空浓缩得红色油状残留物。用硅胶柱过滤，先用正己烷/乙酸乙酯混合液洗涤，接着用二氯甲烷和乙酸乙酯混合液洗涤。合并滤液，真空浓缩，用二氯甲烷重结晶得浅黄色针状固体。m.p.158～160℃。2-（对氯苯基）-1-甲基-5-（三氟甲基）吡咯-3-腈的制备 于2.87g 2-(对氯苯基）-1-甲基-5-（三氟甲基）-2-吡咯啉-3-腈的氯苯溶液中，加入1.76g溴的氯苯溶液，加热至100℃，反应4～5h。冷却至室温，用水稀释，乙酸乙酯抽提。合并提取液，逐次用水、偏亚硫酸钠和水洗涤，无水硫酸镁干燥，真空浓缩得浅黄色固体残留物。用正戊烷/乙酸乙酯重结晶得浅黄色结晶2.4g,m.p.129.5～130℃。4-溴-2-（对氯苯基）-1-甲基-5-（三氟甲基）吡咯-3-腈的制备 于2-（对氯苯基）-1-甲基-5-（三氟甲基）吡咯-3-腈（5.70g）的氯苯溶液中，加入3.52g的溴，加热至80℃，保持20h。冷却后，加3.52g的溴，再加热至100℃。反应混合物冷却，乙酸乙酯抽提。合并提取液，逐次用水和偏亚硫酸钠溶液洗涤，无水硫酸镁干燥，真空浓缩得固体残留物。残留物用乙酸乙酯/正己烷混合溶剂结晶，得白色固体6.50g。m.p.126～129℃。4-溴-2-（对氯苯基）-1-（溴甲基）-5-（三氟甲基）吡咯-3-腈的制备 在搅拌下，将7.27g 4-溴-2-（对氯苯基）-1-甲基-5-（三氟甲基）吡咯-3-腈溶于四氯化碳中，加入3.52g的溴，加热至一定温度，光照2～4d，随后冷到室温，用偏亚硫酸钠水溶液洗涤，有机相真空浓缩，残渣从正庚烷中重结晶得白色固体产品。m.p.131～131.5℃。虫螨腈的制备 将4-溴-2-（对氯苯基）-1-（溴甲基）-5-（三氟甲基）吡咯-3-腈4.42g与无水乙醇混合，用21%乙醇钠0.715g的乙醇溶液处理，加热至80℃，保持15～25min。冷却，用水和乙醚稀释，分离有机层，无水硫酸镁干燥。真空浓缩，正庚烷重结晶，得白色固体虫螨腈3.45g。m.p.91～92℃。制备方法二由三氟乙酰氨基-4-氯苯甲酸与醛酸酐作用，制得2-（4-氯苯基）-5-三氟甲基噁唑酮-3，再将它与α-氯代丙烯腈反应，制得2-（4-氯苯基）-5-三氟甲基吡咯-3-腈，随后再先后与溴素和氯甲基乙醚反应制得虫螨腈。虫螨腈合成路线详见《农药》，2003，42（2）。