7696-12-0 Usage
Air & Water Reactions
Hydrolysis occurs with strong acid or base.
Reactivity Profile
A pyrethroid. Tetramethrin is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Trade name
FMC 9260?; ENT-27339; EVERCIDE
INTERMEDIATE? 2265 (tetramethrin + fenvalerate);
MULTICIDE?; NEO-PYNAMIN?; NEOPYNAMINE?;
NEOPYNAMIN FORTE?; NIAGARA?-9260; NIA?-
9260; PHTHALTHRIN?; SP-1103; SUMITOMO?
SP-1103
Metabolic pathway
Tetramethrin was the second synthetic pyrethroid to be produced commercially
(1964). The compound has a rapid knock-down action and a
reasonable killing activity which is enhanced by use with synergists. It is
usually used with piperonyl butoxide and in the presence of other insecticides.
It has two chiral centres, both in the acid group, and therefore is a
1 RS-cis-trans mixture. A(1R)-rich product containing cis- and trans-isomers
in the ratio 20:80 is also used in public health; this is named dtetramethrin.
The two products will not be distinguished here because
metabolic studies have been performed with various combinations of
isomers. Most published information relates to its mode of action in
insects and its metabolism in rodents. This is a reflection of its limited
outdoor and field use.
Degradation
Tetramethrin is a stable chemical but it is base labile and it is also sensitive
to strong acids. It is hydrolysed to (1RS)-cis-trans-2,2-dimethyl-3-(2-
methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid, 2)
and tetrahydrophthalimide (4). It is oxidised by m-chloroperbenzoic acid
to form epoxy-tetramethrin (5) which is ring-opened to the diol (6) in
dilute aqueous acid (Smith and Casida, 1981). This reaction has been
postulated as initiating the opening of the cyclopropane ring with the
ultimate formation of CO 2 in biological systems (see below). Another
biomimetic reaction of tetramethrin and its ester cleavage product 4 is
Michael addition of thiols to the double bond. Glutathionyl-tetramethrin
(7) is formed by incubation of the constituents in buffered aqueous
methanol (Smith et al., 1982). Its formation on incubation with mouse liver
microsomes is probably non-enzymatic. At the time of this discovery
there appeared to be no equivalent reaction in vivo but the more recent
discovery of sulfonate metabolites (see below) demonstrates its role.
The chrysanthemic acid esters are very sensitive to photodegradation,
being subject to ring-opening initiated by the formation of epoxides such
as 5 (Ruzo et al., 1982) as described under bioallethrin and phenothrin.
Isomerisation was observed only in de-oxygenated benzene solution
because photo-oxidative degradation predominated under most conditions.
Many products were seen in oxygenated benzene solution and in a
thin film in sunlight.
These chemical and photochemical reactions are summarised in
Scheme 1.
Check Digit Verification of cas no
The CAS Registry Mumber 7696-12-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,6,9 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 7696-12:
(6*7)+(5*6)+(4*9)+(3*6)+(2*1)+(1*2)=130
130 % 10 = 0
So 7696-12-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3/t14?,15-/m0/s1
7696-12-0Relevant articles and documents
Para-hydroxyphenylacetic acid for reducing the repellency of insecticides
-
, (2008/06/13)
The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.
Methods and agents for combating cockroaches
-
, (2008/06/13)
The present invention relates to the use of compounds of the general formula I STR1 in which R1 represents C1 -C5 -alkyl or hydroxy-C1 -C5 -alkyl; R2 represents C1 -C5 -alkyl; and m represents an integer from 10 to 20, for combating cockroaches.