| Identification | More | [Name]
ISOFENPHOS | [CAS]
25311-71-1 | [Synonyms]
1-METHYLETHYL-2-[[ETHOXY[(1-METHYLETHYL)AMINO]PHOPHINOTHIOYL]-OXY]-BENZOATE
1-METHYLETHYL-2-[[ETHOXY[(1-METHYLETHYL)-AMINO]PHOSPHINOTHIOYL]-OXY]BENZOATE
AMAZE(R)
BAY 92114
BAY SRA 12869
ISOFENPHOS
Isofenphos powder granules
O-ETHYL O-2-ISOPROPOXYCARBONYLPHENYL ISOPROPYL PHOSPHORAMIDO THIOATE
OFTANOL
2-((ethoxy((1-methylethyl)amino)phosphinothioyl)oxy)-benzoicaci1-methyl
2-((ethoxy((1-methylethyl)amino)phosphinothioyl)oxy)benzoicacid1-methylethy
2-(o-aethyl-n-isopropylamidothiophosphoryloxy)-benzosaeure-isopropylester
40sd
Amaze
Amidocid
discus
Isophenphos
Isopropyl 2-([ethoxy(isopropylamino)phosphorothioyl]oxy)benzoate
isopropyl-phosphoramidothioicacio-ethylo-(2-isopropoxycarbonylphenyl)
isopropylsalicylateo-esterwitho-ethylisopropylphosphoramidothioate | [EINECS(EC#)]
246-814-1 | [Molecular Formula]
C15H24NO4PS | [MDL Number]
MFCD00041805 | [Molecular Weight]
345.39 | [MOL File]
25311-71-1.mol |
| Hazard Information | Back Directory | [Chemical Properties]
Isofenphos is a colorless oil at room temperature. It is sparingly soluble in water, but soluble in cyclohexone, toluene, acetone, and diethyl ether. The US EPA has grouped isofenphos under RUP, which indicates that qualifi ed, certifi ed, and trained workers are required in the safety management of isofenphos. It is used on turf and ornamental trees and shrubs to control white grubs, mole crickets, and other insects, such as soil-dwelling insects, cabbage root fl ies, corn roundworms, and wire worms. | [General Description]
Colorless oil. Non corrosive. Used as an insecticide. | [Reactivity Profile]
Organothiophosphates, such as ISOFENPHOS(25311-71-1), 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. | [Air & Water Reactions]
Hydrolyzed by alkali solution. | [Health Hazard]
Exposures to isofenphos are highly toxic to animals and humans. Acute and prolonged exposures to high concentrations of isofenphos has caused poisoning with symptoms such as increased secretions, diffi culty in breathing, diarrhea, urination, pupil contraction, slowness of the heart, convulsions, and coma. Isofenphos in combination with malathion cause severe poisoning in humans. | [Health Hazard]
Exposures to isofenphos are highly toxic to animals and humans. Acute and prolonged exposures to high concentrations of isofenphos has caused poisoning with symptoms such as increased secretions, diffi culty in breathing, diarrhea, urination, pupil contraction, slowness of the heart, convulsions, and coma. Isofenphos in combination with malathion cause severe poisoning in humans.In 1990, an outbreak in the north of England, involving a large number of pigs, consumption of contaminated feed, and development of ataxia, has suggested that isofenphos causes delayed neuropathy. In view of the hazards and based on the requests of the manufacturers, the US EPA indicated the proposals to phase out isofenphos. Studies have indicated that isofenphos is not mutagenic, teratogenic, or carcinogenic to animals and humans.
| [Uses]
Insecticide. | [Uses]
Isofenphos is an organophosphorus insecticide used in soil to control leaf-eating and
soil-dwelling pests in vegetables, fruits, turf and field crops. | [Uses]
Isofenphos is used as a systemic insecticide to control cabbage root
flies, carrot flies, onion flies and other soil insects in vegetables, rape,
maize, bananas, sugar cane and other crops. | [Definition]
ChEBI: Isofenphos is an organothiophosphate insecticide, an organic phosphonate, a phosphonic ester, a member of salicylates and an isopropyl ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical. It is functionally related to an isopropyl salicylate. | [Environmental Fate]
Soil. Rapidly degraded by microbes via oxidative desulfuration in soils forming isofenphos
oxon (Abou-Assaf et al., 1986; Abou-Assaf and Coats, 1987; Somasundarum et al.,
1989), isopropyl salicylate and carbon dioxide (Somasundaram et al., 1989). The formation
of isofenphos oxon is largely dependent upon the pH, moisture and temperature of the
soil. The degradation rate of isofenphos decreased with a decrease in temperature (35°C
>25°C >15°C), moisture content (22.5% >30% >15%) and in acidic and alkaline soils
(pH 6 and 8 >pH 7). After isofenphos was applied to soil at a rate of 1,12 kg/ai/ha, concentrations
of 8.3, 7.2, 5.1 and 1.0 ppm were found after 5, 21, 43 and 69 days, respectively.
Following a second application, 4.9, 1.55, 0.25 and 0.10 ppm of isofenphos were found
after 5, 21, 43 and 69 days, respectively (Abou-Assaf and Coats, 1987).
A pure culture of Arthrobacter sp. was capable of degrading isofenphos at different
soil concentrations (10, 50 and 100 ppm) in less than 6 hours. In previously treated soils,isofenphos could be mineralized to carbon dioxide by indigenous microorganisms (
Plant. Two weeks following application to thatch, 65% of the applied amount was
present (Sears et al., 1987).
Surface Water. In estuarine water, the half-life of isofenphos ranged from 9.8 to 11.9
days (Lacorte et al., 1995).
Photolytic. Irradiation of an isofenphos (500 mg) in hexane and methanol (100 mL)
using a high pressure mercury lamp (l = 254–360 nm) for 24 hours yielded the following
products: isofenphos oxon and O-ethyl hydrogen-N-isopropylphosphoroamidothioa | [Metabolic pathway]
14C-Isofenphos is bioactivated by mixed-function
oxidases that ultimately give N-desisopropylisofenphos
oxon, a product with 2300-fold greater inhibitory
potency than isofenphos oxon towards housefly head
acetylcholinesterase.271 By housefly and the cuperous
chafer, isofenphos is metabolized to give detoxified
metabolites without the bioactivated N-
desisopropylisofenphos oxon. No difference in kinds of
metabolite is found between the two insects. When
rats are administered 14C-isofenphos, most of the
radioactivity is recovered from the water fraction of the
urine and feces. Aminoisofenphos and isofenphos
oxon are detected in the benzene fraction, and the
other six metabolites are identified as water-soluble
metabolites which include O-ethylhydrogen
phosphoramidate and O-ethylhydrogen
isopropylphosphoramidothioate. Water-soluble
metabolites are predominantly formed through
cleavage of the P-O-aryl linkage. | [Metabolism]
Main degradation route
is cleavage of the P?O-aryl ester linkage through
oxidative desulfuration to isofenphos oxon followed by
hydrolysis and oxidative dearylation from isofenphos.
In plant, the major metabolites are salicylic acid and
dihydroxybenzoic acid. | [Degradation]
Isofenphos is stable to hydrolysis with a DT50 of >1 year at pH values from
4 to 9. Photodegradation on soil surfaces in the laboratory was extremely
rapid but under natural light conditions photolysis was slower (PM). | [Toxicity evaluation]
The acute oral LD50 for rats is about 20 mg/kg.
Inhalation LC50 (4 h) for rats is 0.3–0.5 mg/L air.
NOEL (2 yr) for rats 1 mg/kg diet (0.05 mg/kg/d). ADI is
1 μg/kg. In mammals, administered isofenphos is rapidly
metabolized and eliminated; almost 95% is excreted within
24 h in the urine and feces. The active metabolite is
des-N-isopropylisofenphos oxon. |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R24/25:Toxic in contact with skin and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
3018 | [WGK Germany ]
2 | [RTECS ]
VO4395500 | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29299090 | [Hazardous Substances Data]
25311-71-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats, mice (mg/kg): 30-40, 90-130 (Homeyer) |
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