DICROTOPHOS CAS 141-66-2
Introduction：Basic information about DICROTOPHOS CAS 141-66-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DICROTOPHOS Basic information
| Product Name: | DICROTOPHOS |
| Synonyms: | DICRON;DICROTOPHOS;EKTAFOS(R);(E)-2-DIMETHYL-CARBAMOYL-1-METHYLVINYLDIMETHYL PHOSPHATE;CARBICRON;C-709;BIDRIN;Bidrin，C709 |
| CAS: | 141-66-2 |
| MF: | C8H16NO5P |
| MW: | 237.19 |
| EINECS: | 205-494-3 |
| Product Categories: | Alpha sort;DAlphabetic;Pesticides&Metabolites;Alphabetic;D;DIA - DICPesticides;Insecticides;Organophorous |
| Mol File: | 141-66-2.mol |
DICROTOPHOS Chemical Properties
| Melting point | <25℃ |
| Boiling point | bp760 400° |
| density | 1.216 g/cm3 (15 ºC) |
| vapor pressure | 9.3 x 10-3 Pa (20 °C) |
| refractive index | 1.468 (589.3 nm 23℃) |
| Fp | 100 °C |
| storage temp. | 0-6°C |
| solubility | Acetone (Slightly), Chloroform (Slightly) |
| pka | -1.27±0.70(Predicted) |
| Water Solubility | Totally miscible |
| Merck | 13,3114 |
| BRN | 1880084 |
| Exposure limits | OSHA PEL: TWA 0.25 mg/m3; ACGIH TLV: TWA 0.25 mg/m3. |
| Major Application | agriculture environmental |
| InChI | 1S/C8H16NO5P/c1-7(6-8(10)9(2)3)14-15(11,12-4)13-5/h6H,1-5H3/b7-6+ |
| InChIKey | VEENJGZXVHKXNB-VOTSOKGWSA-N |
| SMILES | COP(=O)(OC)O\C(C)=C\C(=O)N(C)C |
| CAS DataBase Reference | 141-66-2(CAS DataBase Reference) |
| EPA Substance Registry System | Dicrotophos (141-66-2) |
Safety Information
| Hazard Codes | T+,N |
| Risk Statements | 24-28-50/53-26 |
| Safety Statements | 28-36/37-45-60-61 |
| RIDADR | 3018 |
| OEB | C |
| OEL | TWA: 0.25 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | TC3850000 |
| HazardClass | 6.1(a) |
| PackingGroup | II |
| HS Code | 29241990 |
| Storage Class | 6.1A - Combustible, acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 1 Inhalation Acute Tox. 2 Dermal Acute Tox. 2 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 141-66-2(Hazardous Substances Data) |
| Toxicity | LD50 in female, male rats (mg/kg): 16, 21 orally; 42, 43 dermally (Gaines) |
| Description | It is a yellowish liquid, bp 130 ?C/0.1 mmHg, vp 9.3 mPa(20 ?C). It ismiscible with water and most organic solventsexcept kerosene. Log Kow = ?0.5. Dicrotophos is ratherstable to heat and slowly hydrolyzed in acidic media andmore rapidly in alkaline media; DT50 (20 ?C) at pH 5, 7,and 9 are 88, 72, and 28 d, respectively. |
| Chemical Properties | Dicrotophos is an amber liquid with a mildester odor. |
| Uses | Contact and systemic insecticide and acaricide used to control pests on rice, cotton, maize, soybeans, coffee, citrus and potatoes. |
| Uses | Dicrotophos is used to control sucking, chewing and boringinsects and mites in a wide range of crops. It is also used as an animalectoparasiticide. |
| Preparation | Dicrotophos is synthesized by the Perkow reactionfrom trimethyl phosphite and N,N-dimethyl-α-chloroacetoacetamide, consisting mainly of the (E)-form. |
| Definition | ChEBI: Dicrotophos is a dialkyl phosphate and an organophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an avicide and an agrochemical. |
| General Description | A yellow to brown liquid with a mild ester odor. Used to control sucking, boring, and chewing pests on rice, cotton, coffee, apples, and other crops. Effective on ornamentals, trees, and shrubs for aphids, leaf hoppers, and scale insects. |
| Air & Water Reactions | Water soluble. |
| Reactivity Profile | Organophosphates, such as DICROTOPHOS, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. DICROTOPHOS is incompatible with the following: Metals [Note: Corrosive to cast iron, mild steel, brass & stainless steel.] . |
| Health Hazard | DICROTOPHOS is extremely toxic. Probable human oral lethal dose is 5 to 50 mg/kg, 7 drops to one teaspoonful for a 70 kg (150 lb.) person. Closely related in toxicity to azodrin. |
| Health Hazard | An extremely toxic organophosphorus pes-ticide; cholinesterase inhibitor. Toxic effectsare similar to those of monocrotophos. Toxicsymptoms include headache, dizziness, muscle spasms, blurred vision, dilation of pupil,nausea, vomiting, diarrhea, abdominal pain,and seizures. Like most other organophosphorus compounds, exposure to this pesticidecan dangerously affect the respiratory system, producing shortness of breath and respiratory depression, which can progress torespiratory paralysis. Dermal exposure mayincrease the heart rate, while oral intake maydecrease the heart rate. This compound canbe hypotensive and psychotic. Ingestion of asmall quantity of the liquid (0.5–2 g) can befatal to adult humans. LD50 oral (rat): 15 mg/kg LD50 skin (rat): 42 mg/kg LC50 inhalation (rat): 0.09 mg/L/4 h (RTEC1985). |
| Fire Hazard | (Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) DICROTOPHOS may burn but does not ignite readily. Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Rapidly hydrolyzes in acid or alkali. Keep away from heat and open flame. |
| Agricultural Uses | Insecticide, Acaricide: EPA restricted Use Pesticide (RUP). Not approvedfor use in EU countries. Dicrotophos was introduced in1956 as a contact systemic pesticide with a wide range ofapplications. Today, dicrotophos is currently used mainlyas an insecticide for apples and other fruit crops, and forcotton pests, mostly in the Mississippi Valley. It is acutelytoxic to birds, especially those that follow their migratorycorridors and feed in the farmlands that have been treatedwith this pesticide. Internationally, dicrotophos is used onrice, coffee and citrus. One of the major degradates of dicrotophosis monocrotophos. All uses of monocrotophoshave been voluntarily cancelled in the United States due toits extreme toxicity to humans and wildlife |
| Trade name | BIDIRL®; BIDRIN®; BIDRIN-R®[C];BIDRIN®[C]; C-709®; C-709®; CARBICRIN®;CARBICRON®; CARBOMICRON®; CIBA 709®;DIAPADRIN®; DICRON®; DIDRIN®; EKTAFOS®;EKTOFOS®; |
| Safety Profile | Poison by ingestion, inhalation, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mutation data reported. Used to control the coffee borer and certain economically important pests of cotton. When heated to decomposition it emits very toxic fumes of NOx and POx. See also ESTERS. |
| Potential Exposure | A potential danger to those involvedin the manufacture, formulation and application of thisorganophosphate. Used to control the coffee borer and certain economically important pests of cotton |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Speed in removing material from skinis of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If thischemical has been inhaled, remove from exposure, beginrescue breathing (using universal precautions, includingresuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. Medical observation is recommended; effect maybe delayed.Note to physician: 1,10-Trimethylenebis(4-formylpyridinium bromide) dioxime (a.k.a TMB-4 dibromide and TMV-4) has been used as an antidote for organophosphatepoisoning. |
| Carcinogenicity | When rats were fed dicrotophosin their diets at concentrations of 0, 1, 10, or 100 ppm for2 years, there were no detectable effects at the 1 ppmconcentration . Plasma cholinesterase was inhibitedat 1 ppm . At 10 and 100 ppm, decreased body weightsand reduced cholinesterase (erythrocyte, plasma, and brainnot specified) activities occurred. Dogs given dicrotophos intheir diets at 0, 0.16, 1.6, or 16 ppm for 2 years showed some instances of slightly excessive salivation . At 16 ppm,both plasma and RBC cholinesterase activity was decreased. |
| Environmental Fate | Soil. The dimethylamino group is converted to an N-oxide then to -CH2OH and aldehyde groups which further degrade via demethylation and hydrolysis (Hartley and Kidd, 1987). Dicrotophos is rapidly degraded under aerobic and anaerobic conditions forming N,N-dimethylacetoacetamide and 3-hydroxy-N,N-dimethylbutyramide as the major metabolites. Other metabolites included carbon dioxide and unextractable residues. The half-life of dicrotophos in a Hanford sandy loam soil was 3 days (Lee et al., 1989).Biological. Identified metabolites of dieldrin from solution cultures containing Pseudomonas sp. in soils include aldrin and dihydroxydihydroaldrin. Other unidentified byproducts included a ketone, an aldehyde and an acid (Matsumura et al., 1968; Kearney and Kaufman, 1976). A pure culture of the marine alga, namely Dunaliella sp., degraded dieldrin to photodieldrin and an unknown metabolite at yields of 8.5 and 3.2%, respectively. Chemical/Physical. Dicrotophos emits toxic fumes of phosphorus and nitrogen oxides when heated to decomposition (Sax and Lewis, 1987; Lewis, 1990). Dicrotophos is hydrolyzed in sodium hydroxide solutions forming dimethylamine. The hydrolysis half-lives at 38°C and pH values of 1.1 and 9.1 are 100 and 50 days, respectively (Sittig, 1985). Lee et al. (1989) reported that the hydrolysis half-lives of di |
| Metabolic pathway | The metabolic fate of dicrotophos mirrors very closely that of itsclose congener, monocrotophos. Technical dicrotophos contains 82%of the E-isomer and 6% of the Z-isomer, the balance being variousimpurities. Most studies on the metabolic fate of this compound haveused a purified material containing >99% E-isomer. Dicrotophos is asystemic vinyl phosphate insecticide with a high water solubility andlow log Kow. The main routes of metabolic degradation are demethylation to des-O-methyldicrotophos and hydrolysis to dimethyl phosphate and N,N-dimethylacetoacetamide.In animals and plants, hydroxylation of theN-methyl group followed by N-demethylation are also important from atoxicological point of view, since these metabolic steps yield highlyactive idubitors of acetylcholinesterase. In the case of dicrotophos,N-demethylation affords monocrotophos as one of the products ofmetabolism. |
| Metabolism | The main degradation routes are O-demethylation todes-O-methyldicrotophos and hydrolysis to dimethyl phosphateand N,N-dimethylacetoacetamide. Oxidative Ndemethylationalso occurs. |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area away from strong oxidizers, metals, strongbases, and heat. Where possible, automatically pump liquidfrom drums or other storage containers to processcontainers. |
| Shipping | UN3018 Organophosphorus pesticides, liquid,toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. |
| Degradation | Dicrotophos is relatively stable at acidic and neutral pH values but itis hydrolysed in alkaline solutions (PM). The DT50s at pH 5, 7 and 9(25 °C) were 117, 72 and 28 days, respectively. The products ofhydrolysis, which were identified by GC of their methyl esters, wereN,N-dimethylacetoacetamide (2), the main product at alkaline pHvalues, and des-O-methyldicrotophos (3), which predominated in acidand neutral solutions (Lee ef al., 1989). Further decomposition of N,N-dimethylacetoacetamide(2) under alkaline conditions then gave acetone(4), CO2 and dimethylamine (5), whereas under acidic conditions thedes-O-methyldicrotophos (3) was shown to decompose to inorganicphosphate (6), monomethyl phosphate (7), methanol (8), acetone (4) andN,N-dimethylacetoacetamide (2) (Brown et al., 1966). Dicrotophos is notsubject to photodecomposition. Photolysis experiments in which aqueoussolutions of monocrotophos were exposed to simulated sunlight (xenonarc lamp) in quartz tubes showed no products other than the hydrolysisproducts 2 and 3, neither was their rate of formation accelerated. Asoil surface photolysis experiment indicated some small loss of dicrotophos,probably as CO2 due to microbial action. No particular photolyticdegradation products were detected apart from minor amounts of thehydrolysis products 2 and 3. After 30 days 80% of the dicrotophos wasrecovered unchanged. Residual metabolites which were unextractablefrom the soil were not generated by photodegradation, since a dark controlexperiment produced the same proportion of unextractable material(Lee et al., 1989) (see Scheme 1). |
| Toxicity evaluation | The acute oral LD50 forrats is 17–22 mg/kg. Inhalation LC50 (4 h) for rats isabout 0.09 mg/L air. NOEL in a three-generation reproductionstudy with rats is 2 mg/kg daily. In mammals,orally administered dicrotophos is rapidly metabolized,and 63–71% was excreted in the urine within 48 h. |
| Incompatibilities | Attacks some metals: Corrosive to castiron, mild steel; brass, and stainless steel l304. Decomposesafter prolonged storage, but is stable when stored in glassor polyethylene containers with temperatures to 40C.Contact with oxidizers may cause the release of phosphorous oxides. Contact with strong reducing agents, such ashydrides, may cause the formation of flammable and toxicphosphine gas |
| Waste Disposal | Dicrotophos decomposes after7 days @ 90C and 31 days @ 75°C. Hydrolysis is 50%complete in aqueous solutions @ 38C after 50 days at pH9.1 (100 days are required at pH 1.1). Alkaline hydrolysis(NaOH) yields (CH3)2NH. Incineration is also recommended as a disposal method. In accordance with40CFR165, follow recommendations for the disposal ofpesticides and pesticide containers. Must be disposed properly by following package label directions or by contactingyour local or federal environmental control agency, or bycontacting your regional EPA office |
DICROTOPHOS Preparation Products And Raw materials
| Raw materials | Trimethyl phosphite |
