DICROTOPHOS
- CAS No.
- 141-66-2
- Chemical Name:
- DICROTOPHOS
- Synonyms
- C-709;BIDRIN;DICRON;oms253;sd3562;Bidirl;ciba709;OMS 253;SD 3562;Ektafos
- CBNumber:
- CB9180864
- Molecular Formula:
- C8H16NO5P
- Molecular Weight:
- 237.19
- MOL File:
- 141-66-2.mol
- Modify Date:
- 2024/3/14 15:18:30
| 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℃) |
| Flash point | 100 °C |
| storage temp. | 0-6°C |
| solubility | Acetone (Slightly), Chloroform (Slightly) |
| Water Solubility | Totally miscible |
| pka | -1.27±0.70(Predicted) |
| Merck | 13,3114 |
| BRN | 1880084 |
| Exposure limits | OSHA PEL: TWA 0.25 mg/m3; ACGIH TLV: TWA 0.25 mg/m3. |
| CAS DataBase Reference | 141-66-2(CAS DataBase Reference) |
| EPA Substance Registry System | Dicrotophos (141-66-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS06,GHS09 |
|---|---|
| Signal word | Danger |
| Hazard statements | H300+H310+H330-H410 |
| Precautionary statements | P260-P262-P273-P280-P302+P352+P310-P304+P340+P310 |
| 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 |
| Toxicity | LD50 in female, male rats (mg/kg): 16, 21 orally; 42, 43 dermally (Gaines) |
DICROTOPHOS Chemical Properties,Uses,Production
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 solvents except kerosene. Log Kow = ?0.5. Dicrotophos is rather stable to heat and slowly hydrolyzed in acidic media and more 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 mild ester odor.
Uses
Dicrotophos is used to control sucking, chewing and boring insects and mites in a wide range of crops. It is also used as an animal ectoparasiticide.
Preparation
Dicrotophos is synthesized by the Perkow reaction from trimethyl phosphite and N,N-dimethyl-α- chloroacetoacetamide, consisting mainly of the (E)-form.
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.
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 approved for use in EU countries. Dicrotophos was introduced in 1956 as a contact systemic pesticide with a wide range of applications. Today, dicrotophos is currently used mainly as an insecticide for apples and other fruit crops, and for cotton pests, mostly in the Mississippi Valley. It is acutely toxic to birds, especially those that follow their migratory corridors and feed in the farmlands that have been treated with this pesticide. Internationally, dicrotophos is used on rice, coffee and citrus. One of the major degradates of dicrotophos is monocrotophos. All uses of monocrotophos have been voluntarily cancelled in the United States due to its 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 involved in the manufacture, formulation and application of this organophosphate. Used to control the coffee borer and certain economically important pests of cotton
Carcinogenicity
When rats were fed dicrotophos in their diets at concentrations of 0, 1, 10, or 100 ppm for 2 years, there were no detectable effects at the 1 ppm concentration . Plasma cholinesterase was inhibited at 1 ppm . At 10 and 100 ppm, decreased body weights and reduced cholinesterase (erythrocyte, plasma, and brain not specified) activities occurred. Dogs given dicrotophos in their 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 its
close congener, monocrotophos. Technical dicrotophos contains 82%
of the E-isomer and 6% of the Z-isomer, the balance being various
impurities. Most studies on the metabolic fate of this compound have
used a purified material containing >99% E-isomer. Dicrotophos is a
systemic vinyl phosphate insecticide with a high water solubility and
low 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 the
N-methyl group followed by N-demethylation are also important from a
toxicological point of view, since these metabolic steps yield highly
active idubitors of acetylcholinesterase. In the case of dicrotophos,
N-demethylation affords monocrotophos as one of the products of
metabolism.
Metabolism
The main degradation routes are O-demethylation to des-O-methyldicrotophos and hydrolysis to dimethyl phosphate and N,N-dimethylacetoacetamide. Oxidative Ndemethylation also occurs.
Shipping
UN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
Attacks some metals: Corrosive to cast iron, mild steel; brass, and stainless steel l304. Decomposes after prolonged storage, but is stable when stored in glass or polyethylene containers with temperatures to 40C. Contact with oxidizers may cause the release of phosphorous oxides. Contact with strong reducing agents, such as hydrides, may cause the formation of flammable and toxic phosphine gas
Waste Disposal
Dicrotophos decomposes after 7 days @ 90C and 31 days @ 75°C. Hydrolysis is 50% complete in aqueous solutions @ 38C after 50 days at pH 9.1 (100 days are required at pH 1.1). Alkaline hydrolysis (NaOH) yields (CH3)2NH. Incineration is also recommended as a disposal method. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office
DICROTOPHOS Preparation Products And Raw materials
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