40596-69-8 Usage
Description
Methoprene is a racemic mixture of two enantiomers (R and S in a ratio of 1:1), acting as a juvenile hormone (JH) mimic, with the S enantiomer being the active component. It was the first insect growth regulator approved by the US Environmental Protection Agency in the 1970s due to its low toxicity to vertebrates and rapid natural chemical degradation in the environment and through organism metabolism. Methoprene is now one of the most widely used and successful insect growth regulators, available in various forms such as emulsifiable concentrates, granules, pellets, briquettes, aerosols, or sustained-release formulations.
Uses
Used in Public Health:
Methoprene is used as an insect growth regulator for controlling many insect pests (Diptera, Pharaoh’s ants, Coleoptera, Homoptera, and Siphonaptera) in public health.
Used in Stored Commodities and Food Handling:
Methoprene is used as a larvicide for controlling insect pests in stored commodities, food handling, processing, and storage establishments.
Used in Mushroom Houses:
Methoprene is used as an insect growth regulator for controlling insect pests in mushroom houses.
Used in Animal Protection:
Methoprene is used as a biochemical pesticide for protecting animals, including pets such as cats and dogs, by being administered orally in capsules or used externally in flea collars. Production animals like cattle receive methoprene in their diet as a food additive.
Used in Plant Protection:
Methoprene is used as an insect growth regulator for controlling insect pests on plants, including glasshouse plants.
Used in Food Production:
Methoprene is used in the production of various foods, such as meat, milk, mushrooms, peanuts, rice, and cereals, to control some insect pests.
Used in Wastewater and Sludge Bed Management:
Methoprene is used for controlling insects in wastewater, sludge beds, and ponds.
Used in Agricultural Applications:
Methoprene is used as an insect growth regulator (IGR) 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.
Used in Silk Production:
Methoprene is used to increase silk production by inhibiting metamorphosis in silkworms, leading to an increase in food intake, individual size, and silking, resulting in a higher amount of cocoon silk.
Used in Control of Tobacco Storage Pests:
Methoprene is used as a pollution-free new pesticide for controlling tobacco storage pests and beetles.
Used in Control of Health Pests:
Methoprene is used to control health pests such as German cockroaches, fleas, mosquitoes, and flies.
Used in Control of Hemiptera Pests:
Methoprene is used in the control of greenhouse aphids and whitefly.
Used in Control of Lepidoptera Pests:
Methoprene is used for controlling Lepidoptera pests during the storage of cereals, flour, and tobacco.
Used in Control of Ants:
Methoprene is used to control ants by blocking the normal development of larvae, leading to infertility and prevention of infestations.
Used in Control of Termites:
Methoprene is used in the treatment of termites, acting as a juvenile hormone to control their population.
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 lookchem (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.
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.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 40596-69-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,5,9 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 40596-69:
(7*4)+(6*0)+(5*5)+(4*9)+(3*6)+(2*6)+(1*9)=128
128 % 10 = 8
So 40596-69-8 is a valid CAS Registry Number.
InChI:InChI=1/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-
40596-69-8Relevant articles and documents
On the stereochemistry of the Horner-Emmons reaction between 3-functionally substituted 2-methyl-2-propenylphosphonates and aliphatic aldehydes 7. Quaternary ammonium phase transfer catalysts in a stereoselective synthesis of esters of 3-methyl-2E,4E-alkadienoic acids
Kryshtal', G. V.,Zhdankina, G. M.,Serebryakov, E. P.
, p. 1048 - 1052 (1993)
The reaction of diethyl 3-ethoxycarbonyl-2-methyl-2-propenylphosphonate (1a) with 3-methylbutanal (2) in heterogeneous MOH (solid)-behzene systems in the presence of 5-10 mol.percent of benzyltriethylammonium chloride (BTEAC) gives the reaction product (3) with a higher, for M = K, or lower, for M = Li, ratio of 2E,4E- and 2Z,4E-stereoisomers than that observed in the absence of BTEAC.Tetrabutylammonium bromide (TBAB) as a catalyst of the reaction 1a + 2 -> 3 in the system KOH (solid) - wet benzene leads to a higher : ratio than BTEAC; this ratio grows from 44:56 without TBAB to 80:20 at 100 mol.percent of TBAB.In the latter case...
PROCESS AND MEANS FOR THE ERADICATION OF TICKS IN THE HABITATS OF SMALL MAMMALS
-
, (2008/06/13)
Disclosed is a process for using a compound according to formula (I) or formula (II) to prepare a mixture for the eradication of ticks in the living quarters of small mammals, especially cats and dogs. Said process consists in applying as needed to the animal or animals of the habitat concerned a topical formulation in sufficiently pesticidal quantities of a compound according to formula (I), or possibly formula (II), at monthly intervals.
Synthesis of S-(+)-methoprene
Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Serebryakov, E. P.,Tolstikov, G. A.
, p. 98 - 99 (2007/10/02)
An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. ca. 50percent) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol.This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5).Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one.The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14percent overall yield.
