8003-34-7 Usage
Uses
Used in Household Insecticides:
Pyrethrins are used as household insecticides for controlling a wide range of flying and crawling insects, such as flies, mosquitoes, and garden insects.
Used in Public Health and Animal Houses:
Pyrethrins are used to control insects and mites in public health, stored products, animal houses, and on domestic and farm animals.
Used in Glasshouse Crops:
Pyrethrins are used on glasshouse crops, although they have relatively limited use on field crops, vegetables, and fruit.
Used in Agricultural, Commercial, Residential, and Public Health Areas:
Pyrethrins are used to kill a number of different flying and crawling insects and arthropods in various locations, including residential, public, and commercial buildings, animal houses, warehouses, fields, and greenhouses.
Used in Veterinary Medicine:
Pyrethrins are extensively used in the field of veterinary medicine for controlling pests on pets and livestock.
Used with Synergists:
Pyrethrins are often used with synergists such as piperonyl butoxide, which inhibits metabolic detoxification and enhances the insecticidal activity of pyrethrins.
Used in Non-Persistent Insect Control:
Due to their rapid degradation in the environment, pyrethrins are an excellent choice for controlling agricultural pests, insects on pets, and livestock, with little known cases of insect resistance.
Used in Indoor and Outdoor Applications:
Pyrethrins have been approved for a wide range of indoor and outdoor uses, including homes, restaurants, broad-scale spraying operations, and organic farms.
Indications
Pyrethrins, rapid-acting compounds, derived from chrysanthemum plants, are
the leading over-the-counter louse remedy. These compounds interfere with
neural transmission, leading to paralysis and death. Piperonyl butoxide (PBO)
potentiates the pyrethrins by inhibiting the hydrolytic enzymes responsible for
pyrethrin metabolism in arthropods.
Air & Water Reactions
Oxidize relatively rapidly in air. Water emulsifiable.
Reactivity Profile
PYRETHRINS decompose rapidly in base; may generate heat with caustic solutions. May also react with acids to liberate heat. Generate flammable hydrogen with alkali metals and hydrides.
Hazard
Toxic by ingestion and inhalation.
Health Hazard
Pyrethrum dust causes dermatitis
and occasionally sensitization.The primary effect in humans from exposure
to pyrethrum is dermatitis. The usual
lesion is a mild erythematous dermatitis with
vesicles, papules in moist areas, and intense
pruritis; a bullous dermatitis may develop.
Some persons exhibit sensitivity similar to
pollinosis, with sneezing, nasal discharge, and
nasal stuffiness.2 A few cases of asthma due to
pyrethrum mixtures have been reported; some
of the people involved had a previous history
of asthma with allergy to a wide spectrum of
substances.
Fire Hazard
Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.
Pharmacology
The chrysanthemates
(pyrethrin I, cinerin I, and jasmolin I) are generally
more potent for insecticidal kill, whereas the
pyrethrates (pyrethin II, cinerin II, and jasmolin II) cause
more rapid knockdown. When combined with synergists,
the pyrethrins are effective at low doses in causing knockdown
and kill of a wide variety of pests. Pyrethrins exert
their effects primarily by acting on sodium channels in
nerves to disturb nerve conductance . Two distinct
effects, referred to as type I and type II, have been defined
for pyrethrins.
Clinical Use
Because of the high cost and rapid degradation of the pyrethrins, they usually are combined with piperonyI butoxide, a synergist. PiperonyI butoxide has no insecticidal activity in it own right but is thought to inhibit the cytochrome P450 enzyme of the insect, thus preventing an oxidative inactivation of the pyrethrins by the parasite. The combination is used in a 10:1 ratio of . piperonyl butoxide to pyrethrins. The mixture is used for treatment of Pedicul us humanus capitis, Pediculus humanus corporis, and Phthir'us pubis. Various dosage forms are available, including a gel, shampoo, and topical solution.
Potential Exposure
Pyrethrins are used as an ingredient of
various contact insecticides. Those engaged in the isolation,
formulation, or application of these materials.
Environmental Fate
If released to air, the relatively low vapor pressure indicates that the pyrethrins and pyrethroids will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase compounds are rapidly degraded by direct photolysis and by reaction with photochemically produced hydroxyl radicals and ozone; the half-lives for these reactions in air are estimated to be 1.3 h and 17 min, respectively. Particulates may travel long distances and are removed from the atmosphere by wet or dry deposition (HSDB, 2013; ATSDR, 2003). Pyrethrins and pyrethroids are strongly adsorbed to the soil surfaces so they are not expected to be mobile. The compounds also strongly adsorb to suspended solids and sediment in the water column. Thus, partitioning to solids attenuates volatilization from soil and water surfaces. Pyrethrins and pyrethroids are often used indoors in sprays or aerosol bombs, and the volatilization rates from glass or floor surfaces may be significantly faster than from soils since these compounds are not likely to adsorb as strongly to these surfaces (ATSDR, 2003). These insecticides are readily biodegraded by microorganisms.
Pyrethrins and pyrethroids bioconcentrate in aquatic organisms, including fish, oysters, and insects. The bioconcentration factor for several commercial products in three species of fish ranged from 180 to 1200 depending on the amount of dissolved organic matter in the water column (ATSDR, 2003).
Metabolic pathway
Each year about 200,000 kg of pyrethrins are used as a crop insecticide,
much of it in enclosed conditions, and in public and animal health. Its
effectiveness outdoors is limited by the high photo-instability of its components.
This factor, and the great complexity of the mixture, has limited
studies on its metabolic fate. The environmental fate of pyrethrum has
been the subject of an excellent review by Crosby (1995). He points out
that, in spite of its still quite wide use, the environmental fate of its components
is largely unknown. The review deals with transport processes
(partitioning, volatilisation, adsorption, etc.), photochemical and chemical
degradation and environmental biotransformation (soil and water) as
predicted from the limited amount of data on the pure components and
that obtained for the closely related synthetic analogues, e.g. the
allethrins, phenothrin and the resmethrins. This is a valuable paper by
one of the foremost scientists in the field. The fates of the chrysanthemic
acid moiety and of the synthetic alcohol moieties of similar structure to
those in the natural pyrethrins (e.g. allethrolone) are considered to be
useful models for the fate of pyrethrin. The pyrethrin I series (chrysanthemate
esters) appears to have higher partition coefficients, bioconcentration
factors, volatility and soil adsorption, but lower aqueous solubility
than does the pyrethrin II series (pyrethrate esters). This suggests that
pyrethrin I (PI), cinerin I (CI) and jasmolin I (JI) may be more readily
transported in the environment.
Photodegradation and biotransformation should be very rapid for both
series. The limited experimental evidence given below supports these
predictions.
The best mformation is available for animals and most of the infomation
given below is derived from in vitro studies using rodent liver microsomes.
The constituents of pyrethrum appear to differ from the synthetic
pyrethroids in being relatively resistant to metabolic hydrolysis. Metabolism
is mainly via hydroxylation and elimination after conjugation.
Degradation
Pyrethrum is stable for years in the dark at ambient temperature. In light,
rapid photo-oxidation occurs with a DT50 in sunlight of ﹤15 minutes.
Hydrolysis to the component acids and alcohols occurs under basic
conditions.
Exposure to sunlight (Ruzo, 1982) affords a complex mixture of
products which is insecticidally inactive. Reactions include isomerisation,
hydrolysis and oxidation. Products derived from the photomodification
of the chrysanthemic acid moiety of pyrethrin I (PI) (Chen
and Casida, 1969) include the analogues of those described under phenothrin. Simultaneous reactions at the alcohol moieties lead to very
complex mixtures of products.
Toxicity evaluation
The pyrethrins have low toxicity to
mammals, and death after exposure to pyrethrins is rare.
Their lability in light and air leads to a lack of residual
activity and the need for repeated applications. This has
restricted the use of the natural pyrethrins in the animal
health sector.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Compounds of the car-
boxyl group react with all bases, both inorganic and
organic (i.e., amines) releasing substantial heat, water and a
salt that may be harmful. Incompatible with arsenic com-
pounds (releases hydrogen cyanide gas), diazo compounds,
dithiocarbamates, isocyanates, mercaptans, nitrides, and
sulfides (releasing heat, toxic and possibly flammable
gases), thiosulfates and dithionites (releasing hydrogen sul-
fate and oxides of sulfur).
Check Digit Verification of cas no
The CAS Registry Mumber 8003-34-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 8,0,0 and 3 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 8003-34:
(6*8)+(5*0)+(4*0)+(3*3)+(2*3)+(1*4)=67
67 % 10 = 7
So 8003-34-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H28O3/c1-7-8-9-10-15-12-17(14(4)19(15)22)24-20(23)18-16(11-13(2)3)21(18,5)6/h7-9,11-12,14,16-18H,1,10H2,2-6H3
8003-34-7Relevant articles and documents
Process for producing cyclopropanecarboxylates
-
, (2008/06/13)
There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1which process comprises reacting cyclopropanecarboxylic acid of formula (2): 2with a monohydroxy compound of formula (3): R6OH??(3),in the presence of a catalyst compound comprising an element of to Group 4 of the Periodic Table of Elements.
