| METHOPRENE Basic information |
| Insect juvenile hormone Toxicity Application Instructions Precautions References |
| Product Name: | METHOPRENE |
| Synonyms: | 11-METHOXY-3,7,11-TRIMETHYL-2E,4E-DODECADIENOIC ACID, ISOPROPYL ESTER;METHOPRENE (TM);METHOPRENE;ALTOSID(R);ISOPROPYL (2E,4E)-11-METHOXY-3,7,11-TRIMETHYL-2,4-DODECADIENOATE;PRECOR;ZR-515;2,4-dodecadienoicacid,11-methoxy-3,7,11-trimethyl-,1-methylethylester,(e,e |
| CAS: | 40596-69-8 |
| MF: | C19H34O3 |
| MW: | 310.47 |
| EINECS: | 254-993-2 |
| Product Categories: | Veterinary drugs;Growth regulatorsAlphabetic;Insecticides;M;META – METH;Pesticides;Alpha sort;Growth regulatorsPesticides&Metabolites;H-MAlphabetic;INSECT HORMONE |
| Mol File: | 40596-69-8.mol |
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| METHOPRENE Chemical Properties |
| Melting point | <25℃ |
| Boiling point | bp0.06 135-136° |
| density | 0.9261 g/cm3 (20℃) |
| vapor pressure | 3.15 x l0-3 Pa (25 °C) |
| refractive index | 1.4200 (estimate) |
| storage temp. | 0-6°C |
| solubility | Chloroform (Slightly), Methanol (Sparingly) |
| Water Solubility | 1.4 mg l-1 (room temperature) |
| form | neat |
| BRN | 1913191 |
| InChIKey | NFGXHKASABOEEW-LDRANXPESA-N |
| CAS DataBase Reference | 40596-69-8 |
| EPA Substance Registry System | Methoprene (40596-69-8) |
| Safety Information |
| Hazard Codes | Xi,N |
| Risk Statements | 36/37/38-51/53 |
| Safety Statements | 26-36-60-61 |
| RIDADR | UN3082 9/PG 3 |
| WGK Germany | 2 |
| RTECS | JR1685000 |
| Hazardous Substances Data | 40596-69-8(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: >34500 mg/kg (Siddall) |
| METHOPRENE Usage And Synthesis |
| Insect juvenile hormone | Methoprene is a kind of insect Juvenile hormone type biochemical insecticide developed by Novartis Co., Ltd. The juvenile hormone is capable of regulating the growth and development of insects and hormones themselves. The major role of juvenile hormone is to suppress the un-aged larvae metamorphosis, to maintain the larvae characteristics of juvenile insects, so that the larvae stage is still maintained after molting. The methoprene act as a kind of tobacco leaf protectors and interfere with the peeling process of insects. It can interfere with the growth and development process of tobacco beetle and tobacco moth so that the imago would lose reproductive capacity, further effectively controlling the growth of the population of the tobacco leaf pest. Information regarding the toxicity, application, and precautions of the insect-preserving hormone insecticides are edited by Tongtong from Chemicalbook (2017-03-04). |
| Toxicity | Acute oral LD50> 34 600mg/kg: body weight. The preparation has a stimulating effect on the eyes, belonging to a low-toxicity pesticide. |
| Application | Juvenile hormone can not kill insects directly insects, can only make insects died in the metamorphosis process, or through infertility or eggs do not hatch to reduce the number of offspring population, it is slow, can not quickly control the risk of fulminant pests, Agricultural applications. At present mainly used in the following areas: Control of health pests. Ethylenolate has a high activity of German cockroaches, which makes both female and male adults sterile. Continue to use this drug treatment, six months to a year later, it can be inferred because of infertility, large cockroaches are also effective. It is also effective to control the fleas, mosquitoes and flies.Control of Hemiptera pests. Enzyme is effective in the control of greenhouse aphids and whitefly. But in the field application stability is not good. The control of greenhouse whitefly and scale insects is effective.Control pests. Proposed juvenile hormones have high activity against Lepidoptera pests during storage of cereals, flour, tobacco and so on. The United States tries to use insecticides and dioxins to be effective for many pests.Control of ants. The insect insect bait can block the normal larvae of the larvae, so that the king of infertility, prevention and treatment of kitchen ants and other effective. It is also useful to report juvenile hormone treatment of termites.Pollution-free new pesticides for the control of tobacco storage pests and beetles and other beetles.Increased silk production. (5 to 4 μg/head) or 5-year-old silkworm (1 to 3 μg/head) can inhibit metamorphosis, so that the fifth instar larvae extended More than 1 day, food intake increases, individual increases, silking increases. Generally can make the amount of cocoon silk increased by about 15%.Insects are different from other insecticides, and they can control pests that are resistant to other insecticides. However, attention should also be paid to the emergence and development of drug resistance to juvenile hormones. |
| Instructions | Storage Tobacco Tobacco Beetle, with 41% soluble powder 40,000 times the liquid, directly sprayed on the tobacco. To ensure uniform spray, completely cover the tobacco leaves, you can use quantitative dilution or special multi-directional ultra-low spray equipment. The different growth and development stages of insects are not as sensitive to juvenile hormones. Larvae or nymphs are most sensitive at the end of age, poor sensitivity to other age. The larvae of Aedes aegypti were 100 times higher than those of 3rd instar larvae. Pupal phase is more sensitive. In the process of insect growth and development, select the appropriate time, with exogenous juvenile hormone treatment, destruction of insects in the normal hormone balance, so that abnormal abnormal metamorphosis, adult infertility or eggs can not hatch, so as to achieve the purpose of control and eradication of pests The The insects treated by the insects, the larvae of the fly larvae can normalize the pupae, but can not be normal feathers, or death, may also feather wings, can not fly. The IC50 fennel was 0.48 μg/L for the larvae of Culex pipiens mosquito, and the ID50 of the pupa was 2.2 μg per pupa. |
| Precautions | The agent has a strong flammability, is strictly prohibited without dilution Direct use of the goods, to stay away from the fire and high fever surface, keep the seal.This product has a stimulating effect on the eyes, should be careful spray. |
| References | 1. Wang Yubing, Lu Yin spectrum editor. Pollution-free pesticide practical manual. Zhengzhou: Henan Science and Technology Press .2004. 2. Editorial Board of Chinese Agricultural Encyclopedia Editorial Committee of Pesticide Editors, Editorial Department of China Agricultural Encyclopedia. |
| Description | Methoprene is the common name for a racemic mixture of two enantiomers (R and S in a ratio of 1:1). The activity of the compound as a juvenile hormone (JH) mimic is restricted to the S enantiomer. Methoprene was the first insect growth regulator approved in the 1970s by the US Environmental Protection Agency after extensive studies showing low toxicity to vertebrates and rapid natural chemical degradation in the environment and through organism metabolism. Nowadays, it is one of the most widely used and successful insect growth regulators. Different products containing methoprene (e.g., pesticides, veterinary drugs) are commercially available in different forms (emulsifiable concentrates, granules, pellets, briquettes, aerosols, or sustained-release formulations). Some of these are applied to water for mosquito control whereas others are sprayed in areas where foods are stored to prevent insect infestations. Methoprene may be used in combination with other active insecticides to optimize pest control. |
| Chemical Properties | Amber colored liquid. Faint fruity odor. |
| Uses | ectoparasiticide |
| Uses | Methoprene is a broad-spectrum synthetic JH mimic, which acts as an insect growth regulator (insecticide). It prevents larval insect stages from undergoing metamorphosis to viable adults and thus acts as a larvicide. Methoprene is considered a biochemical pesticide because rather than controlling target pests through direct toxicity, methoprene interferes with the insect life cycle, preventing the insect from reaching maturity or reproducing. It is useful for control of a variety of insect pests including ants, mosquitoes, flies, fleas, beetles, lice, and moths, but is only effective against larvae, not adults or pupae. In order to control some of these insects, methoprene is used in the production of a number of foods including meat, milk, mushrooms, peanuts, rice, and cereals. Many different products (e.g., pesticides, veterinary drugs) and formulations containing methoprene are commercially available. Methoprene products used for protecting pets such as cats and dogs include capsules administered orally and flea collars used externally. Production animals (e.g., cattle) typically receive methoprene in the diet as a food additive. Other formulations of methoprene include emulsifiable concentrates, pellets and tablets, granules, and aerosols. Some of these are applied to water for mosquito control whereas others are sprayed in areas where foods are stored to prevent insect infestations. A potential therapeutic use of methoprene was proposed in the context of African sleeping sickness, since it was observed that this compound killed Trypanosoma brucei in culture. However, methoprene acid, resulting from the insecticide metabolism, exhibited no efficiency as trypanocide. Consistently, methoprene administered to infected mice showed to be unable to eliminate trypanosomes from the blood. |
| Uses | Methoprene controls many insect pests (Diptera, Pharaoh’s ants, and also Coleoptera, Homoptera and Siphonaptera) in public health, stored commodities, food handling, processing and storage establishments, mushroom houses, on animals and on plants (including glasshouse plants). |
| Definition | An insecticidal preparation said to act in the manner of a juvenile hormone, which arrests development of insects in the larval stage. |
| Agricultural Uses | Insect growth hormone: Methoprene is an insect growth regulator (IGR) used against a variety of insects including horn flies, mosquitoes, beetles, tobacco moths, sciarid flies, fleas (eggs and larvae), fire ants, pharoah ants, midge flies and Indian meal moths. Controlling some of these insects, methoprene is used in the production of a number of foods including meat, milk, mushrooms, peanuts, rice and cereals. It also has several uses on domestic animals (pets) for controlling fleas and to control insects in wastewater, sludge beds and ponds. For oral use in dogs, 9 weeks of age and older and 4 pounds body weight or greater, for the prevention and control of flea populations [21 CFR 520.1390]. Not approved for use in EU countries . Registered for use in the U.S. |
| Trade name | ALTOSID®; APEX®; DIACON®; DIANEX®; ENT 70,460®; EXTINGUISH®; FLEATROL®; KABAT®; MANTA®; MOORMAN’S® IGR CATTLE CONCENTRATE; OVITROL®; PHARORID®; PRECOR®; ZR-515® |
| Potential Exposure | Methoprene is a natural insect growth regulator (IGR) that mimics juvenile hormone(s) and is used against a variety of insects including horn flies, mosquitoes, beetles, tobacco moths, sciarid flies, fleas (eggs and larvae), fire ants, pharoah ants, midge flies and Indian meal moths. Controlling some of these insects, methoprene is used in the production of a number of foods including meat, milk, mushrooms, peanuts, rice and cereals. It also has several uses on domestic animals (pets) for controlling fleas and to control insects in wastewater, sludge beds and ponds. For oral use in dogs, 9 weeks of age and older and 4 lb body weight or greater, for the prevention and control of flea populations |
| Environmental Fate | Methoprene may be degraded by demethylation, hydrolysis, oxidative cleavage, and photodegradation, resulting in the formation of a series of metabolites that include methoprene acid and citronellic acid. The primary modes of degradation are photodegradation and degradation by aquatic microorganisms. It is metabolized rapidly in soil under both aerobic and anaerobic conditions (half-life = 10–14 days). The major microbial degradation product is carbon dioxide. Degradation in both freshwater and saltwater is also quite rapid with a halflife of 10–35 days at 20 ℃. Methoprene is not very soluble in water (<2 ppm) and as a result is not highly mobile in soil. Because of this and its rapid biodegradation, methoprene does not persist for long periods in soil and is unlikely to contaminate groundwater. When released into water, methoprene is expected to adsorb to suspended solids and sediment. A high potential for bioconcentration in aquatic organisms has been suggested, with an estimated bioconcentration factor of 3400. However, studies with bluegill sunfish, showed no significant bioconcentration of methoprene in fish tissues as a result of aquatic exposure. Methoprene rapidly degrades in plants, with a half-life of 1–2 days in alfalfa when applied at a rate of 1 pound per acre. In rice, the half-life is less than 1 day. In wheat, its half-life was reported to be 3–7 weeks, depending on the level of moisture in the plant. |
| Metabolic pathway | Methoprene is readily degraded biologically by hydrolysis of the ester group, O-demethylation and oxidative cleavage of the bond at the 4-position. |
| Shipping | UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required |
| Degradation | Methoprene (1) is stable in water and in the presence of aqueous acids and alkalis. It is sensitive to UV light. Isomerisation of the double bond is facile. In sunlight (S)-methoprene decomposes to a number of products. These include trans,trans-( S)-methoprenic acid, 2-cis,4-trans-( S)-methoprenic acid, and 2-cis,4-trans-(S)-methoprene. When [5-14C]methoprene was irradiated in direct sunlight in Pyrex vessels in aqueous solutions (0.01 ppm and 0.50 ppm) the DT50 was less than one day. Initially decomposition was rapid, but after one week 12% and 5% 1 remained in the 0.5 and 0.01 ppm solutions, respectively. Carbon dioxide was collected and total 14C recovered was not less than 94% during a 21-day experiment. Five products were characterised as oxygenated products but could not be positively identified. For product identification, an aqueous emulsion of methoprene was irradiated in sunlight and four photoproducts (24% yield) were characterised as methoxycitronellal dimethyl acetal(3,3.9%), methoxycitronellic acid (4,4.7%), an epoxide of methoprene (5,4%) and a methyl ketone (6,4%). In addition to unreacted methoprene there were at least 46 other photoproducts of which none represented more than 2% yield. Rose Bengal and anthraquinone increased the rate of photocatalysed breakdown of methoprene and the profile of products was similar to that obtained by irradiation of a thin film. The extent of decomposition in the presence of anthraquinone was 86% after 6 hours and the predominant product was methoxycitronellal (2, l0-14%). Photosensitised oxidation was slow and 47% of the original was unreacted and a single major product (12%) was identified as the dihydrofuranol (7) (Quistad et al., 1975a) (see Scheme 1). |
| Toxicity evaluation | Acute oral LD50 for rats: >34,600 mg/kg |
| Waste Disposal | It is the responsibility of chemical waste generators to determine if a discarded chemical is classified as a hazardous waste. See 40 CFR Parts 261.3 for United States Environmental Protection Agency guidelines for the classification determination. In addition, in order to ensure complete and accurate classification, waste generators must consult state and local hazardous waste regulations. Incineration might be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers |
| METHOPRENE Preparation Products And Raw materials |