60-51-5 Usage
Uses
Used in Agricultural Industry:
Dimethoate is used as a systemic and contact insecticide and acaricide for the control of a wide range of insect and mite pests in many crops, such as mites, aphids, thrips, plant hoppers, white-flies, and others that damage crops, fruits, vegetables, and ornamental plants.
Used in Animal Husbandry:
Dimethoate is used to control flies in animal houses and for the control of cattle grubs that infect livestock.
Used in Pest Control:
Dimethoate is used as a systemic and contact organophosphorus insecticide and acaricide to control thrips and red spider mites on many agricultural crops, sawflies on apples and plums, and wheat bulb and olive flies.
References
[1]Engenheiro, E. L., et al. "Influence of dimethoate on acetylcholinesterase activity and locomotor function in terrestrial isopods." Environmental Toxicology & Chemistry 24.3(2005):603.
[2]John, Susan, et al. "Protective effect of vitamin E in dimethoate and malathion induced oxidative stress in rat erythrocytes." The Journal of nutritional biochemistry 12.9 (2001): 500-504.
[3]Sharma, Yukti, et al. "Dimethoate-induced effects on antioxidant status of liver and brain of rats following subchronic exposure." Toxicology 215.3 (2005): 173-181.
Air & Water Reactions
Dimethoate is stable in aqueous solution but is hydrolyzed by aqueous alkali.
Reactivity Profile
Dimethoate is incompatible with alkaline preparations. Dimethoate is slightly corrosive to iron. Dimethoate is incompatible with sulfur based formulations. . Organophosphates 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.
Health Hazard
Very toxic; the probable oral lethal dose in humans is between 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. Dimethoate is a cholinesterase inhibitor, meaning it affects the central nervous system. Death is due to respiratory arrest arising from failure of respiratory center, paralysis of respiratory muscles, intense bronchoconstriction or all three.
Health Hazard
Dimethoate is toxic to animals and humans. Occupational exposures cause poisoning with
symptoms that include, but are not limited to, sweating, headache, weakness, giddiness,
nausea, vomiting, stomach pains, blurred vision, pupillary constriction, slurred speech, and
muscle twitching. Workers repeatedly exposed to dimethoate have shown symptoms of
numbness, tingling sensations, incoordination, headache, dizziness, tremor, nausea, abdominal
cramps, diffi culty breathing or respiratory depression, slow heart beat, and speech
diffi culties. Prolonged exposures cause severe poisoning with adverse effects on the CNS,
leading to incoordination, slurred speech, loss of refl exes, weakness, fatigue, involuntary
muscle contractions, twitching, tremors of the tongue or eyelids, and eventually paralysis
of the body extremities and the respiratory muscles, psychosis, irregular heart beats, unconsciousness,
convulsions, coma, and death caused by respiratory failure or cardiac arrest.
Health Hazard
Cholinesterase inhibitor; very toxic, exhibit-ing acute, delayed, and chronic toxicity;routes of entry—ingestion, skin contact,and inhalation; toxic symptoms include nausea, vomiting, diarrhea, excessive salivation,bronchoconstriction, and respiratory arrest;oral intake of 5–20 g may cause death toadult humans.LD50 oral (mammal): 15 mg/kgThe oral LD50 in rat, however, is higher(within the range 150 mg/kg) than someother common organophosphorus insecti-cides, such as Nemaphos, Mevinphos, orCoumaphos.
Fire Hazard
As with other organophosphorus pesticides, container may explode in heat of fire. The temperature of storage should not exceed 70-80F. Keep away from sources of heat, flames, or spark-generating equipment. Unstable in alkaline solution. Hydrolyzed by aqueous alkali. Stable in aqueous solutions. The compound is stable for 2 years under environmental conditions if stored in undamaged, original containers.
Trade name
REBELATE?; CEKUTHOATE?;
CHIMIGOR 40?; CYGON 400?[C]; DEFEND?;
DAPHENE?; DANADIM?; DANADIM? PROGRESS;
DE-FEND?; DEMOS NF?; DEVIGON?; DICAP?;
DIMATE 267?; DIMET?; DIMETHOATE 40;
DIMETHOPGAN?; FERKETHION?; FOSTION
MM?; KENLOGO?; NUGOR?; PERFEKTION?;
ROGODAN?; ROGODIAL?; ROGOR?; ROXION?;
SEVIGOR?
Contact allergens
This organophosphorus compound is used as a contact
and systemic insecticide and acaricide. It induced an
erythema-multiform-like contact dermatitis in a ware-
houseman in an agricultural consortium.
Safety Profile
A deadly human
poison. Poison by ingestion, skin contact,
intraperitoneal, and subcutaneous routes.
Moderately toxic by intravenous route.
Human systemic effects: coma, dyspnea,fasciculations. Questionable carcinogen with
experimental carcinogenic data.
Experimental teratogenic and reproductive
effects. Human mutation data reported.
When heated to decomposition it emits very
toxic fumes of NOx、, POx, and SOx. See also
ESTERS.
Carcinogenicity
Rats given diets with 0, 5, 25,
or 100 ppm dimethoate (0, 0.25, 1.25, or 5 mg/kg/day) for
2 years showed dose-related trends for spleen hemangiosarcoma;
combined spleen hemangioma and hemangiosarcoma;
and combined spleen hemangioma, hemangiosarcoma, and
skin hemangiosarcoma . There were also significant
differences in pair-wise comparisons between controls and
low-dose (0.25 mg/kg) or high-dose (5 mg/kg) groups for
spleen (hemangioma/hemangiosarcoma) and combined
tumors of spleen and skin hemangiosarcoma and lymph
angioma/angiosarcoma; and between low and high doses
for all tumors combined.
Environmental Fate
Soil. Duff and Menzer (1973) reported that in moist soils, dimethoate is converted to the oxygen analog, dimethoate carboxylic acid (dimethoxon) and two unidentified metabolites. The degradation rate of dimethoate in three different soils increased almost twofold with a 10°C increase in temperature (Kolbe et al., 1991). The reported half-lives of dimethoate in a humus-rich sandy soil, clay loam and heavy clay soil at 10 and 20°C are 15.3, 10.3, 15.5 days and 9.7, 4.8 and 8.5 days, respectively. Degradates included dimethoxon (O,O-dimethyl-S-(N-methylcarbamoylmethyl)phosphorothiolate) and unidentified polar compounds (Kolbe et al., 1991).In a silt loam and sandy loam, reported Rf values were 0.42 and 0.45, respectively (Sharma et al., 1986).Plant. In plants, oxidation/hydrolysis leads to the formation of the phosphorothioate. Other hydrolysis products in plants include O,O-dimethylphosphorodithioate and O,Odimethylphosphorophosphate which occurs via demethylation and hydrolytic cleaThe half-life in Bermuda grass was reported to be 3.1 days (Beck et al., 1966). The disappearance half-lives of dimethoate on bean, tomato, cucumber and cotton plants were 4.3, 6.0, 3.8 and 3.3 days, respectively (Belal and Gomaa, 1979).Surface Water. Though no products were identified, the half-life in raw river water was 8 weeks (Eichelberger and Lichtenberg, 1971). Photolytic. Dichlorvos should not undergo direct photolysis since it does not absorb UV light at wavele
Metabolic pathway
Dimethoate is a systemic insecticide which is rapidly translocated to all
parts of the plant. Metabolism to omethoate (dimethoate oxon), the active
cholinesterase inhibitor, is a major pathway in both animals and plants.
Degradative metabolism is either via dealkylation to yield both des-O-
methyldimethoate and des-O-methylomethoate, followed by hydrolysis
or dealkylation to give mono- and di-methyl phosphate, phosphorothioate
and phosphorodithioate esters which are ultimately degraded to phosphate.
An additional mechanism is through hydrolysis of the amide
group to give dimethoate and omethoate carboxylic acids. An important
additional metabolic pathway is oxidative N-demethylation of dimethoate
and omethoate to give des-N-methyldimethoate and des-N-methy
lomethoate via their respective N-hydroxymethyl derivatives. It is possible that the N-demethylation route could precede amidase action
leading to dimethoate and omethoate carboxylic acids which are excreted
in mammals. The 'thioglycolate' part of the molecule is metabolised to
α-hydroxy-N-methylacetamide in mammals.
Degradation
Dimethoate is stable in aqueous media in the pH range 2-7 but hydrolysed
under alkaline conditions (PM). Under acidic conditions the sole
product of hydrolysis is desmethyldimethoate (2), whereas in alkali both
desmethyldimethoate (2) and O,O-dimethylphosphorothioate (3) were
formed. These products are in accord with other studies on the effects of
pH on the hydrolysis of phospho-triesters, with dealkylation predominating
under acidic conditions and SN2 attack on phosphorus by OH- at
high pH (PSD, 1993).
Dimethoate is stable to photolysis. In an experiment to measure
the degradation of an aqueous solution of dimethoate, a sample of
[O-14C-methyl]dimethoate was irradiated with a xenon arc lamp for 15
days. The compound was extracted unchanged (93.4%) and no specific
degradation products were identified (PSD, 1993).
Toxicity evaluation
The acute oral
LD50 for rats is 387 mg/kg. Inhalation LC50 (4 h) for rats
is >1.6 mg/L air. NOEL (2 y) for rats is 5 mg/kg diet
(0.25 mg/kg/d). ADI is 2 μg/kg (sum of dimethoate and its
oxon, i.e., omethoate). Oxidative desulfuration to form
omethoate, the active AChE inhibitor, occurs both in
mammals and plants. The main degradation routes are
O-demethylation and amide hydrolysis that is important
particularly for the selective species toxicity in animals.
The cleavage of the P?S and S?C linkages also occurs to a
considerable degree. Aerobic DT50 in soil is 2–4 d,whereas
it was 22 d under anaerobic conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 60-51-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 60-51:
(4*6)+(3*0)+(2*5)+(1*1)=35
35 % 10 = 5
So 60-51-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7)
60-51-5Relevant articles and documents
Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives
-
, (2008/06/13)
The invention relates to novel cis-alkoxyspiro-substituted tetramic acid derivatives of the formula (I), in which A, G, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly cis-alkoxyspiro-substituted tetramic acid derivatives and secondly a crop plant compatibility-improving compound.
SUBSTITUTED SPIROCYCLIC KETOENOLS
-
, (2008/06/13)
The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms
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, (2008/06/13)
The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.
Optically active 2,5-bisaryl-delta1-pyrrolines and their use as pest control agents
-
, (2008/06/13)
Novel optically active Δ1-pyrrolines of the formula (I) in which R1, R2, R1, R4, and m are each as defined in the description, a plurality of the processes for preparing these substances and their use for controlling pests.
Phenyl-substituted 5,6-dihydrophyne derivatives for use as pesticides and herbicides
-
, (2008/06/13)
The present invention relates to novel phenyl-substituted 5,6-dihydro-pyrone derivatives of the formula (I) in which W, X, Y, Z, G, A, B, Q1 and Q2 are each as defined in the description, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
Delta1-pyrrolines used as pesticides
-
, (2008/06/13)
Novel Δ1-pyrrolines of the formula (I) in which Ar1, Ar2 and Q are each as defined in the description, a plurality of processes for preparing these substances and their use for controlling pests.
Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)
-
, (2008/06/13)
The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.
Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)
-
, (2008/06/13)
The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 2 to 10, n represents 0, 1 or 2, Y represents unsubstituted or substituted methylene and p represents 1, 2 or 3. and to processes for their preparation and to their use as pesticides.
Sulfonylpyrroles
-
, (2008/06/13)
Novel sulfonylpyrroles of the formula in which R1 and R2 independently of one another represent hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, R3 represents hydrogen, cyano, halogen or optionally substituted heterocyclyl, R4 represents halogen, cyano, nitro, trifluoromethyl or thiocarbamoyl and R5 represents optionally substituted heterocyclyl, a process for preparing the novel compounds and their use for controlling unwanted microorganisms.
Delta 1-pyrrolines used as pesticides
-
, (2008/06/13)
Novel Δ1-pyrrolines of the formula (I) in which R1, R2, R3, m and Q have the meanings given in the description, a plurality of processes for preparing these substances and their use for controlling pests.
