120068-37-3 Usage
Description
Fipronil is a white crystalline solid with a moldy odor, characterized by its low solubility in water and slow-acting poison properties. It is a broad-spectrum insecticide belonging to the phenylpyrazole group, known for its effectiveness in disrupting the central nervous system of insects by blocking the passage of chloride ions through GABA receptors. Fipronil was first used extensively in the United States in 1996 for various applications.
Uses
Used in Agricultural Industry:
Fipronil is used as an insecticide for the control of a wide range of insect species in rice, cereals, corn, cotton, top fruit, sugar beet, sugar cane, oilseed rape, and many vegetables and other high-value crops. It is effective against ants, beetles, cockroaches, fleas, ticks, termites, mole crickets, thrips, rootworms, and weevils.
Used in Veterinary Medicine:
Fipronil is used as an ectoparasiticide in the control of fleas, ticks, and chewing lice on domestic animals. It is also used as a topical insecticide, applied on the back side skin of dogs and cats. However,
Trade name
BES? 602; CEASEFIRE?; CHIPCO?;
COMBAT?; FRONTLINE; MB-46030?; H&G?;
ICON?; MAXFORCE? ANT STATION; MAXFORCE?
ROACH STATION; REGENCY SOFION?; REGENT?;
REGENT? 500-FS; TERMIDOR? L VI-NIL
Pharmacology
Fipronil is a phenylpyrazole, the mode of action of which
is to inhibit nerve transmission in arthropods by blocking
γ -aminobutyric acid-gated chloride channels. Fipronil is
available as spray and spot-on formulations to control
fleas and ticks on cats and dogs. The adulticidal activity of
fipronil accounts for the majority of its activity, although
additional activity against flea eggs and larvae results
from the presence of fipronil on hairs and debris shed into
the environment from treated pets.Autohistoradiography studies (11) into the cutaneous
distribution of 14C-fipronil in the cat and dog following
spot-on administration demonstrated that radioactivity
was restricted principally to the stratum corneum, the
viable epidermis, and the pilosebaceous units. Following
its slow release from sebaceous glands, fipronil migrates in
the sebum covering the skin and hairs by passive diffusion
and was shown to persist on hair for up to 2 months after
treatment.
Potential Exposure
Pyrazole/phenylpyrazole/organofluor ine insecticide; veterinary medicine. Fipronil was intro duced into the United States in 1996 for use in animal
health and indoor pest control. It is the constituent of many
products for controlling a wide spectrum of domestic ani mal and residential pests. Banned for use in EU.
Metabolic pathway
Through the abiotic degradation of fipronil in aqueous
solution and on the soil surface, 5-amino-3-
carbamoyl-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-
[(trifluoromethyl)sulfinyl]pyrazole is the only hydrolysis
product detected. Fipronil in acidic aqueous solution
exposed under a xenon lamp degrades with the
concomitant appearance of 5-amino-3-cyano-1-[2,6-
dichloro-4-(trifluoromethyl)-phenyl]-4-
(trifluoromethyl)pyrazole and 5-amino-3-cyano-1-[2,6-
dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-sulfonic
acid. Under field conditions, when fipronil is applied in
formulation, four metabolites which include one
product resulting from reduction on the sulfur atom of
fipronil are detected.
Shipping
UN2588 Pesticides, solid, toxic, Hazard Class:
6.1; Labels: 6.1-Poisonous materials, Technical Name
Required. UN2902 Pesticide, liquid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
Degradation
Fipronil is stable in water at pH 5 and 7 but is slowly hydrolysed at pH 9
(DT50 28 days) to the amide (2). It undergoes rapid aqueous photolysis
with a DT50 of ﹤0.5 day. The major photodecomposition product in water
and on soil surfaces is desulfinyl-fipronil(3) which is formed by extrusion
of the SO group. A minor photoproduct in water, on soil and on plant
surfaces is the sulfonic acid (4). The mechanisms of these reactions are
discussed in a recent paper by Bobe et al. (1998).
Toxicity evaluation
Acute oral LD50 for rats: 100 mg/kg
Waste Disposal
It is the responsibility of
chemical waste generators to determine the toxicity and
physical properties and of a discarded chemical and to
properly identify its classification and certification as a haz ardous waste and to determine the disposal method. United
States Environmental Protection Agency guidelines for the
classification determination are listed in 40 CFR Parts
261.3. Additionally, waste generators must consult and fol low all regional, national, state and local hazardous waste
laws to ensure complete and accurate classification and dis posal methods.
Check Digit Verification of cas no
The CAS Registry Mumber 120068-37-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,0,6 and 8 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 120068-37:
(8*1)+(7*2)+(6*0)+(5*0)+(4*6)+(3*8)+(2*3)+(1*7)=83
83 % 10 = 3
So 120068-37-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2
120068-37-3Relevant articles and documents
Preparation method of trifluoromethyl sulfinyl chloride
-
Paragraph 0019; 0021-0022, (2021/07/24)
The invention relates to a preparation method of trifluoromethyl sulfinyl chloride. The preparation method does not need to use a toxic reagent, namely thiophosgene, does not need to be further oxidized, and has the advantages of simple production process and low cost. The trifluoromethyl sulfinyl chloride is prepared from bis(trifluoromethyl) disulfide, a chlorination reagent and an oxidizing agent in a solvent by a one-pot method, the weight ratio of the solvent to the bis(trifluoromethyl) disulfide is (1: 1)-(500: 1), the temperature of the chlorination reaction is -30 DEG C to 80 DEG C, and the temperature of the oxidation reaction is -30 DEG C to 30 DEG C. The preparation method has the advantages that the preparation of the trifluoromethyl sulfinyl chloride does not need to use a toxic reagent, namely thiophosgene, further oxidation is not needed, meanwhile, the production process is simple, the conversion rate is high, and the production cost is low.
Preparation method of trifluoromethylsulfinyl halide (by machine translation)
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Paragraph 0047-0049, (2020/04/22)
The invention relates to a trifluoromethylsulfinyl halide (chemical formula of F. 3 Process CSOX) of, This compound is used as a pesticide, for the preparation of pesticides and fine chemicals, in particular for preparing insecticide fipronil, and its preparation process :1) trichloromethyl thionyl chloride, i.e. Cl3 Reaction of CSCl with oxidant gives trichloromethyl sulfinyl chloride, (Cl)3 CSOCl;2) Trichloromethyl sulfinyl chloride Cl3 Reaction of CSOCl) with fluoride to give trifluoromethanesulphonyl halide, i.e. F3 CSOX. Has the advantage: that the preparation of trifluoromethylsulfinyl halide avoids the low boiling, highly toxic starting materials and intermediates, namely trifluoromethyl sulfachloride and di (trifluoromethyl) bisulfide, has the advantages, of simple, efficient, safe; convenience and the like, and uses cheap and readily available raw material trichloromethyl sulfur chloride or a mixture, thereof to reduce manufacturing cost. (by machine translation)
Synthetic method of fipronil and analogues thereof
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Paragraph 0040-0066, (2019/10/04)
The invention discloses a method for synthesizing fipronil and analogues thereof. The fipronil and analogues thereof are shown as a formula (I). The synthesis method comprises the following steps: (a) mixing a thioether compound shown as a formula (II) with trichloroacetic acid and an aprotic organic solvent; (b) adding hydrogen peroxide into the mixture obtained in the step (a), and carrying out oxidation reaction, so as to obtain fipronil as shown in a formula (I) and analogues thereof; the substituents in the formula (I) and the formula (II) are defined in the specification. The novel synthetic method is simple in condition and easy for industrial production.