フィプロニル

５－アミノ－１－［２，６－ジクロロ－４－（トリフルオロメチル）フェニル］－３－シアノ－４－［（トリフルオロメチル）スルフィニル］ピラゾール · フィプロニル標準品 · フィプロニル標準液 · フィプロニル · ５アミノ１（２，６ジクロロ４トリフルオロメチルフェニル）４トリフルオロメチルスルフィニルピラゾル３カルボニトリル · 5-アミノ-1-[2,6-ジクロロ-4-(トリフルオロメチル)フェニル]-3-シアノ-4-[(トリフルオロメチル)スルフィニル]ピラゾール (別名フィプロニル) · 5-アミノ-1-[2,6-ジクロロ-4-(トリフルオロメチル)フェニル]-3-シアノ-4-(トリフルオロメチル)スルフィニルピラゾール · 5-アミノ-1-[2,6-ジクロロ-4-(トリフルオロメチル)フェニル]-4-(トリフルオロメチル)スルフィニルピラゾール-3-カルボニトリル

https://huagongshe.com/ja/chemical/3352

識別子と物理属性

CAS No.	120068-37-3
分子式	C12H4Cl2F6N4OS
平均分子量	437.1 g/mol
単同位体質量	435.9387063 g/mol
SMILES	N#Cc1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1S(=O)C(F)(F)F
InChIKey	ZOCSXAVNDGMNBV-UHFFFAOYSA-N
PubChem CID	3352
ChEMBL	CHEMBL101326
ChEBI	CHEBI:83394
EC No.	424-610-5
DTXSID	DTXSID4034609
現地名	フィプロニル

化学・物理的性質

XLogP	4.5
極性表面積	104
水素結合供与体数	1
水素結合受容体数	11
回転可能結合数	2
重原子数	26
形式電荷	0
複雑度	599
LogP（分配係数）	log Kow = 4.0
密度	1.477-1.626 at 20 °C
Color/Form	White solid
溶解度	In water, 1.9 mg/L (pH 5), 2.4 mg/L (pH 9), 1.9 mg/L (distilled), all at 20 °CIn water, 2 mg/LIn organic solvents (g/L at 20 °C): acetone 545.9, dichloromethane 22.3, hexane 0.028, toluene 3.0In acetone, >50%corn oil >10,000 mg/LSolubility in water: very poorDMSO: 250 mg/mL (571.89 mM)1.9-2.4 mg 1l-1 (20 °C）
融点	200-201 °C200-201°C
蒸気圧	2.78X10-9 mm Hg at 25 °CVapor pressure at 20 °C: negligible3.7×10-7 Pa (25 °C)
Physical Description	SolidWHITE POWDER.
Stability/Shelf Life	Stable under recommended storage conditions.
Kovats Retention Index	2069205220592049
Collision Cross Section	178.1 Å² [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID4034609]178.83 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]190.65 Å² [M+Na]+ [CCS Type: TW180.77 Å² [M+H]+ [CCS Type: TW]181.45 Å² [M+H]+177.61 Å² [M-H]-194.16 Å² [M+Na]+180.21 Å² [M+H]+ [CCS Type: TWIonization: GC-APCI+]
沸点	510.1±50.0 °C(Predicted)
貯蔵条件	Keep in dark place,Sealed in dry,2-8°C
pKa（酸解離定数）	-5.86±0.20(Predicted)
外観・状態	Solid
色	White to Light yellow
Merck	14,4085
BRN	8090115
ヘンリー定数	1.2×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
主な用途	農業環境
InChI	1S/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
InChIKey	ZOCSXAVNDGMNBV-UHFFFAOYSA-N
SMILES	Nc1c(c(nn1-c2c(Cl)cc(cc2Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F
LogP（分配係数）	4.000
CAS データベース	120068-37-3(CAS DataBase Reference)
EPAの化学物質情報	Fipronil (120068-37-3)

化学的特性

White SOlid

安全性と法規制

GHS 分類	DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]H311: Toxic in contact with skin [Danger Acute toxicity, dermal]H331: Toxic if inhaled [Danger Acute toxicity, inhalation]H372 *: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
規制情報	Regulation (EC) No 1107/2009 (amended)Fipronil is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)07/52/EC, 2010/21/EU, Reg (EU) 2015/408, Reg. (EU) 2016/2035, Reg. (EU) 2022/801, Reg. (EU) No 540/2011, Reg. (EU) No 781/2013Status: No longer Valid Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/4397Fipronil: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
火災危険	Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
有害性の概要	Sold as Magforce roach killer bait containing 0.1% fipronilThis product may be irritating to the skin and eyes following prolonged contact but is not acutely toxic after ingestion or dermal exposureAlso sold as Chipco Choice Insecticide, containing 0.1% fipronilThis product may cause seizures after skin absorption, ingestion, or inhalation. A termiticide product contains 9.1% fipronil. Seizures are listed as possible effects from overexposure to this product. [MSDSonline] Causes seizures in high-dose animal studiesTechnical (96.5%) fipronil is classified as moderate toxicity, and formulated products are classified as low toxicity. Formulated products may cause some skin irritation to pets, but are not absorbed through the skin[NPIC]

用途

GABA依存性Cl−チャンネル遮断剤チョウ目・カメムシ目・コウチュウ目・バッタ目など広範囲の害虫に有効

説明

Fipronil is a white powder with a mouldy odour. It has a low solubility in water and is a slow-acting poison. It does not bind strongly with soil, and the half-life of fipronil– sulphone is 34 days. Fipronil is a broadspectrum insecticide of the phenylpyrazole group. Fipronil was first used extensively for the control of ants, beetles, cockroaches, fleas; ticks, termites, mole crickets, thrips, rootworms, weevils, flea of pets, field pest of corn, golf courses, and commercial turf, and other insects. Fipronil was first used in the United States in 1996. Fipronil is a topical insecticide. It kills adult fleas and larvae, ticks, and chewing lice. As a liquid, fipronil is applied on the back side skin of dogs and cats. Reports indicate that some animals do become hypersensitive (allergic) to fipronil.

使用

Fipronil is used for the control of a wide range of insect species in rice, cereals, corn, cotton, top fruit, sugar beet, sugar cane, oilseed rape, many vegetables and other high-value crops. It also has a veterinary use as an ectoparasiticide.