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Methomyl

Methomyl is a broad-spectrum , chemically known as S-methyl N-(methylcarbamoyloxy)thioacetimidate, with the molecular formula C₅H₁₀N₂O₂S and a molecular weight of 162.21 g/mol. It appears as a white crystalline solid with a slight sulfurous and is highly soluble in water (approximately 58 g/L at 20°C). Introduced in by E.I. du Pont de Nemours and Company, it functions as a systemic anticholinesterase agent that inhibits in , leading to their and . Methomyl is primarily used in to control foliage- and soil-borne insect pests, including , , and Coleoptera, on a variety of food and feed crops such as , , , peppers, corn, and (with restrictions on the latter). It is also applied to turf on farms and as a non-agricultural fly bait, but residential uses are prohibited. Due to its rapid breakdown in soil and low environmental persistence ( typically 1–7 days under aerobic conditions), it has limited long-term accumulation in ecosystems, though it can pose acute risks to aquatic organisms like and at low concentrations. The compound is extremely toxic to humans via (oral LD₅₀ approximately 17–24 mg/kg in rats) and moderately toxic via , acting as a that can cause symptoms such as , , , respiratory distress, and potentially in severe exposures. It is classified as a restricted-use in the United States, requiring certified applicators for handling, and has been subject to regulatory actions by the U.S. Environmental Protection Agency (EPA) to mitigate risks. In 2015, the EPA approved voluntary cancellations of methomyl uses on , oats, and , limited applications on and certain , and modified fly bait formulations to prevent illegal use on ; ongoing registration reviews address potential impacts on .

Overview

Chemical Identity

Methomyl is classified as a insecticide and nematocide, belonging to the family of monomethyl carbamates that act primarily through systemic and contact modes on target pests. Its IUPAC name is (E,Z)-methyl N-{[(methylamino)carbonyl]oxy}ethanimidothioate, also known by the synonymous systematic name S-methyl N-(methylcarbamoyloxy)thioacetimidate. Common synonyms include Lannate (a ) and metomil. The is 16752-77-5. The molecular formula of methomyl is C₅H₁₀N₂O₂S, with a molecular weight of 162.21 g/mol. The features a central ether linkage connecting a thioacetimidate moiety to a group, which is characteristic of its class. Key functional groups include the (-O-C(=O)-NH-CH₃), responsible for its insecticidal activity; the (-C= N-O-), providing and reactivity; and the thioether (-S-CH₃), contributing to the molecule's . The carbon-nitrogen in the exhibits E/Z isomerism.

History

Methomyl was developed by and introduced in 1966 as an experimental broad-spectrum insecticide under the code designation Du Pont 1179 and the trademark Lannate. It was first registered for use in the United States in 1968, targeting a wide range of insect pests including , , and Coleoptera on various crops. also contributed to early regulatory submissions, providing data supporting methomyl's registration as part of the review process in the late and . By the , methomyl saw rapid early adoption for crop protection, particularly in field crops like , soybeans, and , where it was applied foliarly to control chewing and sucking . Its versatility led to the expansion of formulations, including emulsifiable concentrates (e.g., Lannate L) and wettable powders (e.g., Lannate WP), enabling broader agricultural use and integration into programs during that decade. This period marked methomyl's establishment as a key , with supervised field trials and residue studies conducted internationally to support its global registration. In 1998, the U.S. Environmental Protection Agency (EPA) completed the reregistration eligibility decision (RED) for methomyl, determining it eligible for continued use subject to additional mitigation measures to address ecological risks and human exposure concerns. Due to its high acute oral toxicity (classified as Toxicity Class I), all methomyl products except low-concentration bait formulations were designated as restricted-use pesticides (RUPs), limiting application to certified applicators and prohibiting residential uses. Post-2015, evolving use patterns have included further restrictions amid growing resistance issues; for instance, pests like the cotton bollworm () and (Bemisia tabaci) have shown reduced susceptibility due to overuse, prompting shifts toward integrated resistance management strategies. As part of the ongoing registration review initiated in 2019, the EPA received final biological opinions from the U.S. Fish and Wildlife Service in January 2025 and the in February 2024 assessing risks to , leading to protective actions announced in August 2025. These developments reflect ongoing adaptations to balance efficacy with environmental and health safety.

Properties

Physical Properties

Methomyl appears as a white crystalline solid with a slight sulfur-like odor. Its density is 1.2946 g/cm³ at 24 °C. The melting point of methomyl is 78 °C. Methomyl exhibits high solubility in water, approximately 58 g/L at 25 °C, and is also soluble in polar organic solvents such as methanol (1000 g/L), acetone (720 g/L), ethanol (420 g/L), and isopropanol (220 g/L). The of methomyl is low, measuring 6.65 mPa at 25 °C. Methomyl decomposes before reaching its . The (log K<sub>ow</sub>) is approximately 0.09, indicating moderate hydrophilicity and limited potential.

Chemical Properties

Methomyl exhibits stability in and mildly acidic aqueous solutions, with no significant observed over 30 days at 5 or 7 and 25°C. In alkaline conditions, however, it undergoes , with a of approximately 36 days at 9 and 25°C. This pH-dependent stability arises from its ester , which is susceptible to nucleophilic attack by ions in media but resistant under or acidic conditions. The compound's reactivity includes sensitivity to strong oxidizing agents, which can oxidize its thioether group to or derivatives, potentially leading to decomposition. It also undergoes hydrolysis, particularly accelerated in alkaline environments, producing methomyl (S-methyl N-hydroxythioacetimidate) as the primary degradation product. Methomyl has a pKa of approximately 13.27 for its carbamate NH group, indicating weak acidity and minimal ionization at typical environmental or formulation values (below 10), where it exists predominantly in its neutral form. In pesticide formulations, methomyl shows good compatibility with common solvents such as , , and acetone, as well as inert ingredients in soluble liquid (), wettable powder (), and suspension concentrate () products. It is incompatible, however, with strong acids, strong bases, and strong oxidizers, which can promote rapid degradation or hazardous reactions during mixing or storage.

Production

Synthesis

Methomyl is typically synthesized in the via a multi-step beginning with the preparation of the key , methomyl (S-methyl N-hydroxythio, MHTA), followed by its conversion to the final product. The is produced by reacting S-methyl thioacetimidate —derived from S-methyl ester—with a salt, such as , in the presence of a base like or bicarbonate. This reaction occurs in an aprotic solvent such as or at temperatures between 35°C and 45°C, with the maintained between 0 and 2 to minimize decomposition of the . The typically requires about 2.5 hours after base addition, yielding methomyl in 80-85% with purity up to 95%. In the subsequent step, methomyl is reacted with to form the N-methylcarbamate linkage. One common laboratory procedure involves dissolving the in water with a catalytic amount of triethylamine (molar ratio of to isocyanate to catalyst approximately 1:1.3-1.6:0.009-0.015), heating to 50-80°C, and adding the isocyanate dropwise while maintaining the temperature. The mixture is then held at 60-80°C for 50-70 minutes, cooled to below 10°C (ideally -5°C to 0°C), and the resulting methomyl crystals are filtered, washed, and dried, achieving yields exceeding 90%. An alternative variant uses methylene chloride as the solvent at 30-50°C, with controlled gaseous addition of to manage the exothermic reaction, followed by solvent evaporation, recovery of unreacted , and recrystallization from for purification. Alternative synthetic routes to methomyl avoid direct use of , which is highly reactive and toxic. One such method employs to first form an O-(methoxycarbonyl) derivative of methomyl , followed by nucleophilic displacement with to introduce the N-methylcarbamoyl group; this two-step process uses basic conditions (e.g., triethylamine in an organic solvent) at low temperatures (around 0-20°C) to control reactivity and yields comparable to the route, though specific yields are reported around 85-95% overall. Another variant utilizes carbamyl intermediates for the carbamoylation step under similar controlled conditions. These alternatives incorporate phase-transfer catalysts or aqueous media to enhance selectivity and reduce byproducts. Safety considerations are paramount due to the toxicity of intermediates like , a volatile gas that can cause severe respiratory irritation and systemic poisoning even at low concentrations (LC50 ~21 in rats). Laboratory syntheses require fume hoods, precise temperature control to prevent runaway exotherms, and ; the and carbamyl chloride routes offer reduced risks by eliminating handling, though phosgene-derived demand similar precautions against and toxicity. All processes emphasize monitoring and inert atmospheres to avoid side reactions leading to hazardous byproducts.

Commercial Production

Methomyl was originally developed and patented by in the , with key U.S. patents such as No. 3,576,834 covering its and use as an , granting exclusive rights until their expiration around 1988. This expiration facilitated the entry of generic manufacturers, expanding production beyond . Worldwide production was estimated at less than 7,000 tonnes as of 1988. In 2015, exported 8,592 tonnes, and in December 2019, Chinese exports reached 990 tonnes. Recent expansions include a 2,000 metric tons per year facility by DGW Group in , operational from 2023. Ongoing EPA registration reviews, including 2025 actions to protect , may impact future production volumes. Major production facilities are concentrated in the United States, , and , with serving as a key supplier. Industrial manufacturing adapts laboratory synthesis—typically a batch reaction of methylthioacetaldoxime with —into a continuous, plug-flow adiabatic process operating under pressure in an inert organic at elevated temperatures (30-50°C), followed by stripping, of unreacted materials, solvent exchange to , , , and for higher efficiency and lower costs. This scaling enhances yield and minimizes waste compared to small-scale methods, enabling technical-grade methomyl production at 90-98% purity suitable for into insecticides. The supply chain for methomyl relies on key raw materials such as methylthioacetaldoxime (derived from acetaldoxime and methyl mercaptan) and (), which is often produced on-site due to its high toxicity and volatility, as highlighted by safety concerns following the 1984 Bhopal incident involving in pesticide production. Sourcing disruptions for , a critical intermediate, can impact costs and availability, with global demand for carbamate pesticides like methomyl exceeding 10,000 tonnes annually in the 1970s and continuing to influence integrated manufacturing strategies today. Post-patent generics have diversified sourcing, reducing reliance on single suppliers but increasing scrutiny on raw material quality and environmental compliance in the chain.

Applications

Agricultural Uses

Methomyl is a broad-spectrum primarily employed in to control a variety of foliage and soil-borne pests through contact and stomach action, providing rapid knockdown effects. It targets key pests such as aphids (, ), beetles, cutworms, armyworms, leafhoppers, , and moths including the tobacco budworm (Heliothis virescens). In crop protection, methomyl is applied to a range of vegetables like tomatoes, potatoes, , celery, and onions; field crops including , soybeans, , peanuts, and ; forage crops such as ; and fruits like apples. On these crops, it effectively suppresses pests like alfalfa weevils in . Typical application rates range from 0.5 to 2 kg per , often as foliar sprays timed to coincide with early stages for optimal . Against Heliothis virescens, methomyl demonstrates high initial efficacy in and , reducing larval populations by over 90% in susceptible strains when applied at labeled rates. However, has developed in some populations due to prolonged use, necessitating integrated strategies such as rotating with insecticides from different chemical classes (e.g., pyrethroids or organophosphates) to maintain long-term control. Beyond crops, methomyl is used on non-agricultural sites including farms for turf , ornamental plants to manage and beetles, and premises to target flies and ticks in animal confinement areas. These applications follow similar low-volume foliar or directed spray methods to minimize off-target exposure while achieving suppression.

Formulations and Application Methods

Methomyl is commonly formulated as wettable powders, such as 90% soluble powder (SP), for easy mixing with water prior to application. Soluble liquid concentrates, typically at 225 g/L, provide a ready-to-dilute option for spray applications, while granular formulations, including 1% baits and 5% granules, are used for targeted soil or baiting purposes. These formulations enhance handling, dispersion, and efficacy depending on the pest and crop requirements. Application methods for methomyl include foliar sprays delivered via ground boom sprayers, airblast equipment, or to cover surfaces effectively. drenches involve mixing the product with water and applying it to the root zone for systemic uptake, while bait stations utilize granular or formulations placed in areas of high pest activity, such as for fly control. Equipment must be calibrated to ensure uniform coverage, with low-pressure nozzles recommended for foliar sprays to optimize droplet size and reduce waste. As of August 2025, all methomyl products except bait formulations are classified as restricted-use pesticides by the U.S. EPA, requiring certified applicators, and include mandatory mitigation measures to protect endangered species, such as enhanced vegetative buffer zones (e.g., 100 feet near water bodies) and spray drift reduction technologies. Methomyl formulations are generally compatible with many other insecticides, fungicides, and adjuvants, allowing tank mixes to broaden pest control spectra, though a jar compatibility test is advised to check for precipitation or separation before field use. Formulated methomyl products should be stored in their original, tightly sealed containers in a cool, dry, well-ventilated area away from direct , heat sources, and foodstuffs, with a typical of up to 2 years under these conditions. To minimize spray drift, applications should occur during low wind speeds (under 10 mph), using drift-reducing nozzles and maintaining zones near sensitive areas; for runoff reduction, avoid application before anticipated rainfall and incorporate vegetative s or farming to retain the product on-site.

Health Effects

Mechanism of Action

Methomyl acts as a by inhibiting the enzyme (AChE), which normally hydrolyzes the at cholinergic synapses in the of . This inhibition prevents the breakdown of , leading to its accumulation and subsequent overstimulation of the , resulting in hyperexcitation, , and death of target pests. Unlike organophosphates, which form a covalent, irreversible bond with the serine residue in the AChE through , methomyl's structure allows for reversible carbamylation of the . The carbamylated AChE complex undergoes spontaneous over time, enabling reactivation without the need for external oximes, typically within hours to days depending on the species and dose. This reversibility contributes to methomyl's lower persistence in biological systems compared to organophosphates. According to the Insecticide Resistance Action Committee (), methomyl is classified in Group 1A, encompassing N-methyl carbamates that target AChE. Compared to other carbamates like or , methomyl demonstrates higher potency in terms of rapid onset, achieving peak AChE inhibition in models within 15 minutes versus 45 minutes for most others, while enzyme recovery occurs within 24 hours for the majority of exposed organisms. These kinetic differences influence its use in , balancing efficacy with reduced risk of prolonged residue effects.

Human Toxicity and Exposure

Methomyl is classified by the U.S. Environmental Protection Agency (EPA) as Toxicity Category I, indicating high , with an oral LD50 of 17–24 mg/kg in rats. Acute human poisoning primarily manifests through inhibition, leading to symptoms such as (pupil constriction), excessive salivation, , , abdominal cramps, , , sweating, muscle tremors, weakness, chest discomfort, and dyspnea (difficulty breathing). In severe cases, respiratory distress and convulsions may occur, potentially progressing to if untreated. Human exposure to methomyl occurs mainly via dermal contact, , and , with occupational risks elevated for applicators during mixing, loading, and application processes. Dermal is significant, as methomyl penetrates rapidly, and exposure is common in spray applications, while often results from accidental contamination or suicidal intent. Farm workers face reentry risks post-application, necessitating protective to mitigate through and lungs. Chronic exposure to low levels of methomyl may cause prolonged inhibition, leading to symptoms like and neurological effects, though the compound is rapidly metabolized in the liver with no . The EPA has classified methomyl as Group E, showing evidence of non-carcinogenicity for s based on . Recent studies (as of 2025) in animal models have identified additional risks, including developmental and cardiovascular toxicity in exposed to methomyl, such as improper heart formation and vascular disruptions, as well as in livers and in developing rat brains. These findings suggest potential broader health concerns from chronic or developmental exposures, though direct remain limited. Documented cases of methomyl include accidental , such as a fatal incident where unlabeled methomyl was mistaken for a beverage, resulting in rapid onset of severe symptoms and death. Occupational exposures have also led to acute poisonings among industrial workers through dermal contact during handling, with symptoms resolving after prompt intervention but highlighting the need for preventive measures. A foodborne outbreak from contaminated bean sprouts affected multiple individuals, presenting with , , and symptoms due to inadvertent . First aid for methomyl poisoning emphasizes immediate decontamination, including removal from exposure, skin washing with soap and water, and or administration for to prevent further . is the primary , administered in titrated doses to counteract muscarinic effects like salivation and , with supportive care for respiratory and cardiovascular symptoms; is generally not recommended for poisonings like methomyl due to potential interference with spontaneous reactivation of .

Environmental Impact

Fate and Persistence

Methomyl degrades in primarily through microbial activity, with an aerobic half-life of approximately 14 days under typical field conditions, though values can range from 3 to 11 days depending on , , and . degradation in typically has half-lives of 10-14 days, but under specific conditions in some subsoils (e.g., presence of ions), half-lives can be as short as less than 5 hours to 7 hours. In aqueous environments, methomyl exhibits a of about 6 days in due to and microbial processes, while it persists much longer in , with a exceeding 25 weeks under sterile or low-oxygen conditions. under sunlight is rapid, with half-lives ranging from 1 to 5 days on surfaces or in aqueous solutions exposed to UV or , producing degradates such as . During processes, methomyl degrades to oxygenated metabolites that retain to aquatic organisms even after the parent compound is fully broken down. Methomyl's high water solubility, approximately 57 g/L at 25°C, contributes to its potential for into , particularly in sandy soils where up to 52% may appear in . However, its soil carbon partition coefficient (Koc) of around 72 indicates moderate adsorption to , limiting mobility in clay-rich or soils to depths typically below 30 cm. Bioaccumulation of methomyl is low, with a estimated at less than 10 in organisms, reflecting its rapid metabolism and excretion in and . No significant accumulation has been observed in tissues after depuration periods.

Ecotoxicity

Methomyl poses substantial risks to non-target organisms due to its as a , which disrupts function across various taxa. In avian species, methomyl is highly toxic, with acute oral LD50 values of 24 mg/kg in bobwhite quail and 28 mg/kg in hens. Sublethal exposures to carbamates like methomyl can impair bird behavior, including reduced feeding efficiency and increased susceptibility to predation through inhibition. Aquatic organisms face acute threats from methomyl, which is moderately to highly toxic to , exhibiting 96-hour LC50 values of approximately 0.79 mg/L in . It demonstrates very high toxicity to aquatic invertebrates, with 48-hour values around 0.0076 mg/L in species such as daphnids. Recent studies (as of 2025) have shown that methomyl induces developmental and cardiovascular toxicity in embryos at low concentrations, highlighting risks to early-life stages of aquatic vertebrates. Pollinators and beneficial insects are particularly vulnerable to methomyl's acute and oral . For honey bees, the oral LD50 is 0.28 µg/bee, and the LD50 is 0.16 µg/bee, classifying it as highly toxic and capable of causing rapid mortality during on treated crops. Such exposures contribute to declines by eliminating foraging adults and disrupting dynamics. Terrestrial wildlife experiences impacts from methomyl primarily through direct or secondary via contaminated prey. Mammals show high , with acute oral LD50 values of approximately 17 mg/kg in rats, leading to symptoms like tremors and respiratory distress. Reptiles lack extensive data, but ecological assessments indicate potential hazards similar to those for birds and amphibians due to comparable and exposure pathways. Field studies and incident reports highlight methomyl's real-world ecotoxic effects, including multiple documented kills from deliberate or accidental exposure. For instance, in 2010, several hundred pigeons died in a Colombian city park after consuming methomyl-treated corn kernels, confirmed by inhibition in tissues. Similar incidents occurred in , where high methomyl concentrations were detected in deceased corellas and cockatoos in 2021 and 2024, respectively. Aquatic contamination from agricultural runoff has led to localized impacts, with potential for and mortality in affected water bodies, though specific methomyl-attributed fish kills are less frequently reported compared to avian events.

Regulations

Regulatory Status

Methomyl was first registered as a by the (EPA) in 1968 for use as a on various crops. Due to its high to humans and non-target organisms, all methomyl products except 1% bait formulations have been classified as restricted-use pesticides (RUPs), limiting application to certified applicators only. The EPA reregistered methomyl in 1998, imposing label amendments to mitigate risks, including enhanced worker protection standards and use restrictions on certain crops. In the , EU-wide approval under Regulation (EC) No 1107/2009 expired following withdrawal from the market in 2007, with limited national authorizations remaining in select member states such as , , , , , , , , and as of November 2025. Prior to full phase-out, strict conditions applied, including limitations on application rates and timing to protect pollinators like bees, contributing to restrictions in parts of the for bee protection purposes. Globally, methomyl's regulatory status varies, with bans in multiple countries due to its high profile; for instance, it was prohibited in in 2022, in June 2025, while remaining permitted in others like despite international concerns. The (WHO) classifies methomyl as Class Ib, indicating it is highly hazardous based on acute oral toxicity (LD50 of 17-24 mg/kg in rats). As part of its ongoing registration review initiated in 2019, the EPA issued proposed interim decisions in 2020 addressing ecological risks and, in August 2025, approved label amendments to protect , including measures to reduce runoff, spray drift, and habitat impacts under the Endangered Species Act, such as buffer zones near aquatic habitats and no-spray zones along streams. No major post-2020 regulatory changes related to pest resistance were implemented, though tolerance assessments continued without altering overall approval status. Labeling requirements for methomyl products emphasize its restricted-use classification, mandating warnings such as "DANGER - " and specifying (PPE) including chemical-resistant gloves, protective clothing, eyewear, and respirators during mixing, loading, and application to prevent acute .

Residue Limits and Safety Guidelines

Methomyl residues in are regulated through maximum residue limits (MRLs) established by international and national authorities to ensure consumer safety. In the , a default MRL of 0.01 mg/kg applies to fruits and where methomyl is not specifically listed, reflecting the general limit for unapproved substances under Regulation (EC) No 396/2005. In the United States, the Environmental Protection Agency (EPA) sets tolerances under 40 CFR 180.253, which vary by commodity; for example, the tolerance is 0.1 for undelinted , 0.2 for potatoes, 1 for apples, and 1 for tomatoes. These limits are derived from toxicological data and exposure assessments to protect vulnerable populations like children. Pre- intervals () specify the minimum time between the last methomyl application and to allow residue below MRLs. For most , PHIs range from 7 to 14 days, though this varies by and ; for instance, a 7-day PHI applies to many applications, while longer intervals like 30 days may be required for certain field uses. Safety guidelines emphasize (PPE) during handling and application, including chemical-resistant gloves, long-sleeved shirts, pants, and socks plus shoes; respirators are recommended for mixing, loading, or aerial applications to prevent exposure. Restricted entry intervals () typically last 48 hours post-application, during which workers must not enter treated areas without appropriate PPE to avoid dermal or risks. Residue monitoring and enforcement involve standardized testing methods to detect methomyl in and . The U.S. (FDA) employs multiresidue methods, such as liquid chromatography-tandem mass spectrometry (LC-MS/MS), for routine screening of domestic and imported commodities, enabling detection at parts-per-billion levels. Similar LC-MS/MS techniques are used by the EPA for environmental samples to assess with benchmarks. Risk mitigation measures focus on preventing environmental contamination, particularly in water bodies. Applicators must maintain buffer zones near aquatic habitats, such as 60 feet for ground applications and up to 450 feet for ultra-low volume sprays, to minimize runoff and drift. These guidelines, aligned with EPA protections, also include no-spray zones along streams to protect sensitive ecosystems.

Commercial Aspects

Trade Names

Methomyl is commercially available under numerous trade names globally, reflecting its use as an insecticide in various formulations such as sprays, dusts, and baits. One of the most prominent brands is Lannate, originally developed and introduced by DuPont in 1966 as a broad-spectrum carbamate insecticide, with early development codes including Dupont 1179 and Insecticide 1179. Following corporate mergers, including DuPont's integration into Corteva Agriscience, Lannate remains a key brand, often formulated as Lannate LV (liquid) or Lannate SP (soluble powder) for agricultural applications. Other major trade names include Nudrin, historically associated with and used for foliar insect control, and Methomex from Makhteshim-Agan (now ), commonly applied in crop protection. For fly control baits, Golden Malrin—containing 1% methomyl and muscalure as an attractant—has been widely used since its introduction, particularly in and facilities, though some variants like Golden Malrin Fly Bait have been discontinued in certain markets. Additional brands such as Mesomile and Lanox 90/216 have appeared in various products. Generic equivalents are prevalent, especially in regions with regulatory approvals, such as Methomyl 225 (225 g/L methomyl soluble ), which in replaced the branded Lannate-L under while maintaining the same formulation. Similar generics include Electra 225 and Nudrin 225, often in 225 g/L concentrations for spray applications. Regional variations highlight market-specific branding. In the United States, Lannate and Nudrin dominate agricultural uses, alongside Golden Malrin for baits. In , methomyl's approval expired in 2019 without renewal, following non-inclusion considerations in 2007; as of 2025, it is not approved for use. Prior to expiry, it was marketed under names like Lannate, Lanox, and Metofan by companies including CropScience. In , particularly , brands such as Mieduowei (from Shenzhen Jiangshan) and Kuik (Rotam) are common, with additional names like Agrinate (Vapco) and (Rocca) used in select markets. Historically, earlier brands included Halvard from , which has been discontinued, reflecting shifts in production following mergers and regulatory changes in the industry. Some products, like Methofan ( + ), have also been phased out due to restrictions on companion active ingredients.

Manufacturers

Agriscience, the successor to Crop Protection, is a primary manufacturer of methomyl-based products such as Lannate , with production historically at facilities in the United States, including the site. The unit there was permanently closed in 2016 following a 2014 methyl mercaptan release incident that killed four workers. Limited also serves as a key producer, offering methomyl formulations like Methomyl 225 for agricultural use, with manufacturing operations supported in and distributed globally. In the global market, generic manufacturers dominated production volumes until the 2024 ban, exemplified by companies such as Yangnong Chemical Co., Ltd., which contributed to the supply of technical-grade methomyl alongside numerous other firms in provinces like and . Production facilities for these generics are primarily located in , with additional sites in , such as those operated by Star Bio Science in and other regional plants. In the U.S., branded products like Lannate hold significant , while generics have proliferated globally since the early following expirations and increased from Asian producers. Supply disruptions for methomyl have arisen from regulatory changes and challenges, including the explosion at a CropScience facility in , which involved ()—a key intermediate in methomyl synthesis—and led to the permanent closure of the methomyl unit, prompting reliance on external sourcing. Further issues include MIC supply constraints due to safety regulations post-incident and the ban in prohibiting methomyl production starting June 1, 2024, which has impacted global availability by constraining generic supply; as of November 2025, production has shifted more toward and other non-Chinese manufacturers, maintaining market stability amid ongoing regulatory pressures. Major methomyl manufacturers adhere to international quality and safety standards, including ISO 9001 for quality management and (GMP) guidelines tailored for to ensure product consistency and environmental compliance.

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