Fenamiphos
- CAS No.
- 22224-92-6
- Chemical Name:
- Fenamiphos
- Synonyms
- PHENAMIPHOS;NEMACUR;sra3886;B 68138;Nenacur;SRA 3886;ent27572;nemacurp;BAY 68138;ai3-27572
- CBNumber:
- CB7215702
- Molecular Formula:
- C13H22NO3PS
- Molecular Weight:
- 303.36
- MOL File:
- 22224-92-6.mol
- Modify Date:
- 2024/3/14 15:18:27
| Melting point | 49°C |
|---|---|
| Boiling point | 375.6±52.0 °C(Predicted) |
| Density | 1.14 |
| vapor pressure | 1.2 x 10-4 Pa (20 °C) |
| Flash point | 100 °C |
| storage temp. | 0-6°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | -0.09±0.70(Predicted) |
| form | Liquid |
| color | Brown |
| Water Solubility | 0.07 g/100 mL |
| Merck | 13,3984 |
| BRN | 4752893 |
| Exposure limits | OSHA PEL: TWA 0.1 mg/m3; ACGIH TLV: TWA 0.1 mg/m3. |
| LogP | 4.01 at 30℃ |
| CAS DataBase Reference | 22224-92-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Fenamiphos(22224-92-6) |
| EPA Substance Registry System | Fenamiphos (22224-92-6) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS06,GHS09 |
|---|---|
| Signal word | Danger |
| Hazard statements | H300+H310+H330-H319-H410 |
| Precautionary statements | P262-P273-P280-P302+P352+P310-P304+P340+P310-P305+P351+P338 |
| Hazard Codes | T+;N,N,T+ |
| Risk Statements | 24-28-50/53-36-26/28 |
| Safety Statements | 23-28-36/37-45-60-61-35-26 |
| RIDADR | UN 2811/3017 |
| OEB | D |
| OEL | TWA: 0.1 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | TB3675000 |
| HazardClass | 6.1(a) |
| PackingGroup | I |
| Toxicity | LD50 orally in rats (mg/kg): 10-25 (Waggoner, Khasawinah); LD50 orally in birds (mg/kg): 2.4 (Hill, Camardese) |
Fenamiphos Chemical Properties,Uses,Production
Description
Fenamiphos is a colorless crystalline substance. Solubility in water is 400 mg/L (20 ?C). It is soluble in polar organic solvents. Log Kow = 3.3(20 ?C). It is stable in aqueous media; DT50 (22 ?C) at pH 4, 7, and 9 are 1, 8, and 3 yr.
Chemical Properties
Fenamiphos is a colorless crystal or a tan, waxy solid. It is non-corrosive to metals and breaks down readily in strong acids and bases. Fenamiphos is used as a nematicide and an insecticide. It is sparingly soluble in water, but readily soluble in dichloromethane, isopropanol, and toluene. It is used primarily for the control of nematodes and thrips on citrus, grapes, peanuts, pineapples, tobacco, turf, and ornamentals. There are no residential uses for fenamiphos. The US EPA has grouped fenamiphos as an RUP owing to its high acute toxicity and toxicity to wildlife. Reports have indicated that the manufacture and sale of fenamiphos is to be phased out by 2007–2008.
Uses
Fenamiphos is primarily used to control nematodes in a wide range of crops and in turf. It will also control mites and sucking insects in crops.
General Description
Brown waxy solid or colorless solid. Used as a nematocide.
Air & Water Reactions
Fenamiphos is hydrolyzed by strong acids and strong alkalis.
Reactivity Profile
Organothiophosphates, such as Fenamiphos, 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.
Hazard
Toxic by inhalation and skin contact. Questionable carcinogen.
Health Hazard
Fenamiphos is highly toxic orally, by inhalation, and by absorption through the skin. (Non-Specific -- Parathion) Death may occur from respiratory failure.
Fire Hazard
(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Emits toxic fumes of nitrogen oxides, phosphorus oxides, and sulfur oxides when heated to decomposition.
Agricultural Uses
Nematicide, Insecticide: A U.S. EPA restricted Use Pesticide (RUP). Fenamiphos is an organophosphate nematicide used to control a wide variety of nematode (roundworm) pests. Nematodes can live as parasites on the outside or the inside of a plant. They may be free living or associated with cyst and root-knot formations in plants. Fenamiphos is used on a variety of plants including tobacco, turf, bananas, pineapples, citrus and other fruit vines, some vegetables, and grains. The compound is absorbed by roots and is then distributed throughout the plant. Fenamiphos, as is typical of other organophosphates, blocks the enzyme acetylcholinesterase in the target pest. The pesticide also has secondary activity against other invertebrates such as sucking insects and spider mites.
Trade name
BAY 68138®; Bayer 68138®; NEMACUR®; NEMACURP®
Safety Profile
Poison by ingestion, inhalation, and skin contact. When heated to decomposition it emits very toxic fumes of NOx, POx, and SOx.
Environmental Fate
Soil. Oxidizes in soil to the corresponding sulfone and sulfoxide (Lee et al., 1986). Fenamiphos rapidly degraded in Arredondo soil to fenamiphos sulfone and at the sametime to the corresponding phenol. The half-life in this soil is 38–67 days (Ou and Rao, 1986).
Surface Water. In estuarine water, the half-life of fenamiphos was 1.80 days (Lacorte et al., 1995).
Chemical/Physical. Emits toxic fumes of phosphorus, nitrogen and sulfur oxides when heated to decomposition (Sax and Lewis, 1987; Lewis, 1990).
Metabolic pathway
Fenamiphos is an effective nematicide with both protectant and curative action. Free-living, ecto- and endo-parasitic, cyst-forming and root knot nematodes are controlled. Foliarly applied compound is translocated in plants to the roots and there is evidence that both translocation and optimum anti-cholinesterase and nematicide activity require oxidation of the thiomethyl group to the sulfoxide or the sulfone. These thiooxidation products are much more easily hydrolysed than fenamiphos itself and hydrolytic degradation in the environment most probably occurs via the formation of these intermediates.
Metabolism
The oxidation of the thiomethyl group to the sulfoxide and sulfone is required for both translocation and nematicidal activity in plants. The oxidation products are more susceptible to hydrolysis than fenamiphos itself. In mammals, orally administered fenamiphos is rapidly metabolized to the sulfoxide and sulfone, followed by subsequent hydrolysis, conjugation, and excretion in the urine. N-Dealkylation also occurs. The DT50 in soils is several weeks; the major degradation products are fenamiphos sulfoxide and sulfone and their phenols.
Fenamiphos Preparation Products And Raw materials
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