Methomyl oxime

C <4.7x10 Pa at 20 °C Water 20 mg at 20 °C Readily soluble in polar organic solvents Stable in neutral and weakly basic conditions Unstable in strongly acidic or basic conditions Stable in most of organic solvents such as acetone, acetonitrile and carbon tetrachloride Undergoes hydrolysis to yield methomyl oxime in alkaline solutions... 

The residue definition includes alanycarb and its metabolite, methomyl (determined as methomyl oxime)... 

Quantitation is performed by the calibration technique. Construct a new calibration curve with methomyl oxime standard solutions (0.2, 0.4, 0.6, 0.8 and 1.0 xgmL in acetone) for each set of analyses. Plot the peak area against the injected amount of methomyl oxime on logarithmic paper. As the amount of alanycarb is measured in terms of its oxime derivative, a conversion factor of 3.8 (the molecular weight ratio of alanycarb to methomyl oxime) should be applied to obtain the net amount. The injection volume should be kept constant as the peak area varies with the injection volume in flame photometric detection. Before each set of measurements, check the GC system by injecting more than one standard solution containing ca 2-10 ng of methomyl oxime. 

C = concentration of methomyl oxime in the final solution ( ag mL ) V = final sample volume (mL)... 

In the case of crop residues, GC determination is carried out on the hydrolyzed product, i.e., methomyl oxime, instead of alanycarb to make effective use of its substantially higher response to the flame photometric detector. In order to prevent vaporization loss of methomyl oxime, ethylene glycol must be added prior to concentration in Section 6.3. In all other concentration operations, full account must also be taken of the high volatility of both alanycarb and methomyl oxime, especially in the process of removal of the last traces of solvents. Alanycarb residue in the sample is stable under storage condition at -20 °C for at least 100 days. 

CASRN 59669-26-0 molecular formula C10H18N4O4S3 FW 354.47 Soil In aerobic and anaerobic soil, thiodicarb degrades to methomyl and methomyl oxime (Hartley and Kidd, 1987). The reported half-life in various soils is 3-8 d (Hartley and Kidd, 1987). 

Oxime carbamates are not directly amenable to gas chromatography (GC) because of their high thermal instability, which often leads to their breakdown at the injection port or in the column during analysis. Analysis of oxime carbamates by GC with sulfur detection or flame photometric detection involves oxidation of the intact insecticides or alkaline hydrolysis to form the more volatile but stable oxime compound. Enzymatic techniques have been reported for the analysis of these compounds. Enzyme-linked immunosorbent assay (ELISA) has been used to determine aldicarb and its sulfone and sulfoxide metabolites and methomyl in water, soil, and sediment samples. 

Oxime carbamates are generally applied either directly to the tilled soil or sprayed on crops. One of the advantages of oxime carbamates is their short persistence on plants. They are readily degraded into their metabolites shortly after application. However, some of these metabolites have insecticidal properties even more potent than those of the parent compound. For example, the oxidative product of aldicarb is aldicarb sulfoxide, which is observed to be 10-20 times more active as a cholinesterase inhibitor than aldicarb. Other oxime carbamates (e.g., methomyl) have degradates which show no insecticidal activity, have low to negligible ecotoxicity and mammalian toxicity relative to the parent, and are normally nondetectable in crops. Therefore, the residue definition may include the parent oxime carbamate (e.g., methomyl) or parent and metabolites (e.g., aldicarb and its sulfoxide and sulfone metabolites). The tolerance or maximum residue limit (MRL) of pesticides on any food commodity is based on the highest residue concentration detected on mature crops at harvest or the LOQ of the method submitted for enforcement purposes if no detectable residues are found. For example, the tolerances of methomyl in US food commodities range from 0.1 to 6 mg kg for food items and up to 40 mg kg for feed items. ... 

The first recommended soil method for oxime carbamates is the method of Honing et al. by HPLC/MS. The LOQ of the method, specifically for aldicarb, methomyl, and oxamyl, is 0.05mgkg. Soil (lOg) is Soxhlet extracted for 16h with acetone-dichloromethane (1 1) using double-thickness cellulose extraction thimbles (80 X 22-mm i.d.). Prior to extraction, the Soxhlet system and the thimbles are cleaned for 14 h by refluxing with methanol. The extracts are removed and concentrated nearly to dryness in a rotary evaporator operating at 35 °C evaporation to dryness... 

Methomyl (S-methyl(-N methyl carbamoxy thioacetimidate or (methylthio)acetald oxime) has been determined in chloroform extracts of soil in amounts down to lpg kg-1 by gas chromatography-mass spectrometry [88]. 

Base hydrolysis kinetic data are reported for ppb solutions of carbofuran,3-OH carbofuran, methomyl and oxamyl. The results are compared with those reported previously for aldicarb, aldlcarb sulfoxide, and aldicarb sulfone. Second order reaction rate constants, k, have been calculated and range from 169 liter mln mole for oxamyl to 1.15 liter mln mole for aldicarb. The order for rate of base hydrolysis is as follows oxamyl >3-hydroxycarbofuran >aldicarb sulfone v- carbofuran >aldicarb sulfoxide > methomyl -v aldicarb. The activation energy for the base hydrolysis of carbofuran was measured to be 15.1 +0.1 kcal mole , and is similar to the value previously reported for aldicarb sulfone. Rapid detoxification of aldicarb, a representative oxime carbamate pesticide, by in situ hydrolysis on reactive ion exchange beds is reported. 

Similarly, on-column methylation has been applied to carbamate pesticides containing an active N-H group. Wien and Tanaka (41) showed that N-aryl carbamates are methylated on-column with tri-methylanilinium hydroxide-methanol to give the intact N-methyl and N-aryl derivatives. On the other hand N-methyl, 0-aryl carbamates such as carbaryl or carbofuran yielded only the methyl ethers of their respective phenols. This work has now been extended to sulfur-containing carbamates such as methomyl, methio-carb, aldicarb, etc. (42-43). Here the oxime hydrolysis products of these carbamates are chromatographed as the 0-methyl oximes. 

Caibamate pesticides are used as insecticide, acaricide, and herbicide. Various subclasses can be distinguished. Aryl V-methyl carbamates (1), such as caibaiyl, carbofuran, propoxur, and oxime V-methyl carbamates(2), such as aldicaib, methomyl, oxamyl, have most widely been studied. LC-MS is the method-of-choice for carbamates, since their thermal lability prohibits GC analysis. 

A few years after the synthesis of aldicarb, several research groups prepared, independent of each other, analogues of aldicarb which have only one carbon atom instead of two between the sulfur atom and the oxime-nitrogen (Anonym, 1966a 1966b Anders, 1967). Finally, 1-methylmercaptoacetaldehyde-O-methyl-carbamoyl oxime (methomyl, 46) was put onto the market as the result of work by the research group of the Du Pont Co. 

Nudrin Lannate Lannate(R) Lanox Methomyl 5G Lannabait Lannate LB Insecticide 1179 Lanox 216 LANOX 90 Mesomile Nu-bait II Thiobutan-2-one, 0-(methylcarbamoyl)oxime Flytek Kipsin Dupont 1179 Memilene Methavin Methomex Nudrin N-((methyl-carbamoyl)oxy]thioacetamidic acid, methyl ester SD 14999 WL... 

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