METHOPRENE CAS 40596-69-8
Introduction：Basic information about METHOPRENE CAS 40596-69-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
METHOPRENE Basic informationInsect 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;INSECT HORMONE;Alpha sort;Growth regulatorsPesticides&Metabolites;H-MAlphabetic;API |
| Mol File: | 40596-69-8.mol |
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 | Liquid |
| color | Colorless to light yellow |
| BRN | 1913191 |
| Major Application | agriculture environmental |
| InChI | InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+ |
| InChIKey | NFGXHKASABOEEW-LDRANXPESA-N |
| SMILES | C(OC(C)C)(=O)/C=C(\C)/C=C/CC(C)CCCC(OC)(C)C |
| 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 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Aquatic Chronic 2 Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 40596-69-8(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: >34500 mg/kg (Siddall) |
| 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:
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| 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 |
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| 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 twoenantiomers (R and S in a ratio of 1:1). The activity of thecompound as a juvenile hormone (JH) mimic is restricted tothe S enantiomer. Methoprene was the first insect growthregulator approved in the 1970s by the US EnvironmentalProtection Agency after extensive studies showing low toxicityto vertebrates and rapid natural chemical degradation in theenvironment and through organism metabolism. Nowadays, itis one of the most widely used and successful insect growthregulators. Different products containing methoprene (e.g.,pesticides, veterinary drugs) are commercially available indifferent forms (emulsifiable concentrates, granules, pellets,briquettes, aerosols, or sustained-release formulations). Someof these are applied to water for mosquito control whereasothers are sprayed in areas where foods are stored to preventinsect infestations. Methoprene may be used in combinationwith other active insecticides to optimize pest control. |
| Chemical Properties | Amber colored liquid. Faint fruity odor. |
| 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 glasshouseplants). |
| Uses | ectoparasiticide |
| Uses | Methoprene is a broad-spectrum synthetic JH mimic, whichacts as an insect growth regulator (insecticide). It preventslarval insect stages from undergoing metamorphosis to viableadults and thus acts as a larvicide. Methoprene is considereda biochemical pesticide because rather than controlling targetpests through direct toxicity, methoprene interferes with theinsect life cycle, preventing the insect from reaching maturityor reproducing. It is useful for control of a variety of insect pests includingants, mosquitoes, flies, fleas, beetles, lice, and moths, but isonly effective against larvae, not adults or pupae. In order tocontrol some of these insects, methoprene is used in theproduction of a number of foods including meat, milk,mushrooms, peanuts, rice, and cereals. Many different products(e.g., pesticides, veterinary drugs) and formulations containingmethoprene are commercially available. Methoprene productsused for protecting pets such as cats and dogs include capsulesadministered orally and flea collars used externally. Productionanimals (e.g., cattle) typically receive methoprene in the diet asa food additive. Other formulations of methoprene includeemulsifiable concentrates, pellets and tablets, granules, andaerosols. Some of these are applied to water for mosquitocontrol whereas others are sprayed in areas where foods arestored to prevent insect infestations. A potential therapeutic useof methoprene was proposed in the context of African sleepingsickness, since it was observed that this compound killedTrypanosoma brucei in culture. However, methoprene acid,resulting from the insecticide metabolism, exhibited no efficiencyas trypanocide. Consistently, methoprene administeredto infected mice showed to be unable to eliminate trypanosomesfrom the blood. |
| Definition | An insecticidalpreparation said to act in the manner of a juvenile hormone, which arrests development of insectsin 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 growthregulator (IGR) that mimics juvenile hormone(s) and isused against a variety of insects including horn flies, mosquitoes, beetles, tobacco moths, sciarid flies, fleas (eggsand larvae), fire ants, pharoah ants, midge flies and Indianmeal moths. Controlling some of these insects, methopreneis used in the production of a number of foods includingmeat, milk, mushrooms, peanuts, rice and cereals. It alsohas several uses on domestic animals (pets) for controllingfleas and to control insects in wastewater, sludge beds andponds. For oral use in dogs, 9 weeks of age and older and4 lb body weight or greater, for the prevention and controlof flea populations |
| Environmental Fate | Methoprene may be degraded by demethylation, hydrolysis,oxidative cleavage, and photodegradation, resulting in theformation of a series of metabolites that include methopreneacid and citronellic acid. The primary modes of degradation arephotodegradation and degradation by aquatic microorganisms. It is metabolized rapidly in soil under both aerobic andanaerobic conditions (half-life = 10–14 days). The majormicrobial degradation product is carbon dioxide. Degradationin both freshwater and saltwater is also quite rapid with a halflifeof 10–35 days at 20 ℃. Methoprene is not very soluble inwater (<2 ppm) and as a result is not highly mobile in soil.Because of this and its rapid biodegradation, methoprene doesnot persist for long periods in soil and is unlikely to contaminategroundwater. When released into water, methoprene isexpected to adsorb to suspended solids and sediment. A highpotential for bioconcentration in aquatic organisms has beensuggested, with an estimated bioconcentration factor of 3400.However, studies with bluegill sunfish, showed no significantbioconcentration of methoprene in fish tissues as a result ofaquatic exposure. Methoprene rapidly degrades in plants, with a half-life of1–2 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 wasreported to be 3–7 weeks, depending on the level of moisturein the plant. |
| Metabolic pathway | Methoprene is readily degraded biologically by hydrolysis of the estergroup, O-demethylation and oxidative cleavage of the bond at the4-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 andalkalis. It is sensitive to UV light. Isomerisation of the double bond isfacile. In sunlight (S)-methoprene decomposes to a number of products.These include trans,trans-( S)-methoprenic acid, 2-cis,4-trans-( S)-methoprenicacid, and 2-cis,4-trans-(S)-methoprene. When [5-14C]methoprene was irradiated in direct sunlight in Pyrexvessels in aqueous solutions (0.01 ppm and 0.50 ppm) the DT50 was lessthan 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 than94% during a 21-day experiment. Five products were characterised asoxygenated products but could not be positively identified. For productidentification, an aqueous emulsion of methoprene was irradiated insunlight and four photoproducts (24% yield) were characterised as methoxycitronellaldimethyl acetal(3,3.9%), methoxycitronellic acid (4,4.7%),an epoxide of methoprene (5,4%) and a methyl ketone (6,4%). In additionto unreacted methoprene there were at least 46 other photoproductsof which none represented more than 2% yield. Rose Bengal andanthraquinone increased the rate of photocatalysed breakdown ofmethoprene and the profile of products was similar to that obtained byirradiation of a thin film. The extent of decomposition in the presenceof anthraquinone was 86% after 6 hours and the predominant productwas methoxycitronellal (2, l0-14%). Photosensitised oxidation was slowand 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 todetermine if a discarded chemical is classified as a hazardous waste. See 40 CFR Parts 261.3 for United StatesEnvironmental Protection Agency guidelines for the classification determination. In addition, in order to ensure complete and accurate classification, waste generators mustconsult state and local hazardous waste regulations.Incineration might be an effective disposal procedurewhere permitted. If an efficient incinerator is not available, the product should be mixed with large amounts ofcombustible material and contact with the smoke shouldbe avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticidecontainers |
METHOPRENE Preparation Products And Raw materials
| Raw materials | 2-Heptene, 6-bromo-2-methyl--->2-Heptene, 7-bromo-2,6-dimethyl--->NSC46306-->7-METHOXY-3,7-DIMETHYLOCTANAL-->2H-Pyran-2-one, 3,6-dihydro-6-(6-methoxy-2,6-dimethylheptyl)-4-methyl--->3-Methylthiophene-->2,6-Dimethyl-5-heptenal |
