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5-[2-(オクチルスルフィニル)プロピル]-1,3-ベンゾジオキソール

Sulfoxide

HCID 8442
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
120-62-7
標準SMILES
CCCCCCCCS(=O)C(C)Cc1ccc2c(c1)OCO2
InChIKey
ATTZFSUZZUNHBP-UHFFFAOYSA-N
分子式
C18H28O3S
平均分子量
324.5 g/mol
単同位体質量
324.17591592

概要

Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)

名称と識別子

優先名称
Sulfoxide
IUPAC
5-(2-octylsulfinylpropyl)-1,3-benzodioxole
現地名
5-[2-(オクチルスルフィニル)プロピル]-1,3-ベンゾジオキソール
英語名
Sulfoxide
分子式
C18H28O3S
分子量
324.48

名称と別名

SulfoxidePIPERONYL SULFOXIDESulfox-cide120-62-7Isosafrole n-octylsulfoxideSulfociden-Octylisosafrole sulfoxiden-Octylsulfoxide of isosafroleSulfoxide (synergist)Isofrol-n-octyl sulfoxideIsosafrole octyl sulfoxideIsosafrole, octyl sulfoxide
名称をさらに表示
イソサフロールn-オクチルスルホキシドスルホキス-シドスルホックスシド5-[2-(オクチルスルフィニル)プロピル]-1,3-ベンゾジオキソールスルホキシルスルホキシドオクチルスルホキシドスルホキシド標準品スルホキシド STANDARDスルホキシド Standard, 100 µg/mL in MeOHピペロニルスルホキシド5-[2-(オクタン-1-スルフィニル)プロピル]-2H-1,3-ベンゾジオキソールスルホキサイドsufoxideSulfoxylent16,634SULFOX-ADESulfoxy(R)Sulphoxide
Piperonyl sulfoxide (insecticide)NCI-C02824ENT 16,6345-(2-octylsulfinylpropyl)-1,3-benzodioxole5-[2-(Octylsulfinyl)propyl]-1,3-benzodioxoleDTXSID10211681-Methyl-2-(3,4-methylenedioxyphenyl)ethyl octyl sulfoxideWOR3CS513R

物性

構造計算による物性

XLogP
4.8
極性表面積
54.7 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
10
重原子数
22
形式電荷
0
複雑度
334

実験および物理化学的性質

PesticidesPesticides -> Other Insecticides
OdorSWEET-SMELLING
Density · 2 件

1.06 to 1.09 at 77 °F (NTP, 1992)

1.06-1.09 @ 25 °C

Color/Form · 2 件

PALE YELLOW, VISCOUS OIL

Brown liquid

Solubility · 3 件

less than 0.1 mg/mL at 72 °F (NTP, 1992)

PRACTICALLY INSOL IN WATER; SOL IN MOST ORGANIC SOLVENTS EXCEPT PETROLEUM ETHER

Insoluble in water.

Flash Pointgreater than 200 °F (NTP, 1992)
DecompositionWHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES OF /SULFUR OXIDES/.
Vapor Pressure0.00000007 [mmHg]
Physical Description · 2 件

Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)

Pale yellow or brown liquid with a sweet odor; [HSDB]

Stability/Shelf Life · 2 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

危険有害性情報

Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include tremors, central nervous system depression and prolonged coma 10 to 20 minutes after exposure.
Hazards Summary · 1 件

Not carcinogenic for rats, but was carcinogenic for male mice with an increased incidence of hepatocellular carcinomas; [NTP] Causes tremor and CNS depression in acute animal studies; Non-toxic in rats fed 0.2% in diet for 15 months; [HSDB] See Piperonyl butoxide.

Reactive GroupSulfonates, Phosphonates, and Thiophosphonates, Organic
Special ReportsBioassay of Piperonyl Sulfoxide for Possible Carcinogenicity (1979) Technical Rpt Series No. 124 DHEW Pub No. (NIH) 79-1379, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Reactivity ProfilePIPERONYL SULFOXIDE reacts violently with perchloric acid. (NTP, 1992). With strong reducing agents it will produce hydrogen sulfide.
Air and Water ReactionsInsoluble in water.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

化学と産業

薬理情報

Mechanism of Action · 1 件

Piperonyl butoxide, like other methylenedioxybenzene synergists (eg, sesamex, sulfoxide, n-propyl isome, piperonyl cyclonene, etc), inhibits hepatic microsomal oxidase enzymes in lab rodents & by inference in man; it also inhibits a related group of enzymes in insects apparently by serving as a competitive substrate. Because these enzymes act to detoxify many drugs & other exogenous chemicals, a heavy exposure to one of these insecticidal synergists might make a person temporarily vulnerable to a variety of toxic insults that would normally be tolerated with ease.

Metabolism/Metabolites · 1 件

MAJOR METABOLIC PATHWAY FOR A & B SULFOXIDE DIASTEREOMERS OF 1,2-METHYLENEDIOXY-4-(2-OCTYLSULFINYL PROPYL)BENZENE AFTER ORAL ADMINISTRATION TO MICE INVOLVED THE CLEAVAGE OF THE METHYLENEDIOXYPHENYL (MDP) MOIETY & EXPIRATION OF THE METHYLENE CARBON AS CARBON DIOXIDE. MIXED-FUNCTION OXIDASES OF LIVER MICROSOMES DEMETHYLATED SEVERAL COMPOUNDS CONTAINING THE MDP MOIETY.

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

用途と製造

Uses · 3 件

Used as insecticide synergist for pyrethrins and allethrin; [HSDB]

Farming (Pesticides) [Category: Industry]

INSECTICIDE SYNERGIST USED WITH PYRETHRINS AND ALLETHRIN

U.S. Production(1978) NOT PRODUCED COMMERCIALLY IN US
Methods of ManufacturingBY ADDITION OF N-OCTYL MERCAPTAN TO ISOSAFROLE; THIOETHER SO FORMED DISTILS AT 183-186 °C/1 MM. THE THIOETHER IS OXIDIZED BY THE ADDITION OF HYDROGEN PEROXIDE TO AN ACETONE SOLUTION; ACETONE & WATER BEING REMOVED BY DISTILLATION IN VACUO.

関連反応

0 件
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現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
120-62-7
PubChem CID
8442
DTXSID
DTXSID1021168
ChEMBL
CHEMBL3184866
ChEBI
CHEBI:82267
UNII
WOR3CS513R
EC Number
204-412-3
Nikkaji
J5.329E

STABLE UNDER NORMAL CONDITIONS

Very stable even to acids & bases (at room temp) /technical 88%/

Other Experimental Properties · 2 件

BROWN LIQUID; DECOMP ON HEATING; DENSITY: 1.06-1.09; INDEX OF REFRACTION: 1.528-1.532 @ 25 °C/D; MILD ODOR /COMMERCIAL MATERIAL/

Vapor pressure is very low at room temp; Practically insol in water; Readily sol or miscible with organic solvents, eg alcohol, acetone, xylene, methylene chloride; In mineral oils 2-2.5%; pale yellow liquid /technical 88%/

物理化学的性質

沸点
432.8 °C · 432.8°C (rough estimate)
比重(密度)
1.104 · 1.1040 (rough estimate)
屈折率
1.546 · 1.5460 (estimate)
貯蔵温度
0 · 0-6°C
安定性
安定。可燃性。強力な酸化剤とは相容れない。過塩素酸と激しく反応する。
EPAの化学物質情報
Piperonyl sulfoxide (120-62-7)

化学的性質

化学的特性light yellow viscous oil

Storage ConditionsMay be stored in iron containers /technical 88%/
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

毒性情報

Interactions · 5 件

...SYNERGIST TO INCR INSECTICIDAL POTENCY OF PYRETHRINS.

OF THE METHYLENEDIOXYPHENYL SYNERGISTS, AT LEAST THE FOLLOWING HAVE BEEN SHOWN TO INCR SLEEPING TIME FOLLOWING ADMIN OF CERTAIN BARBITURATES &/OR TO INHIBIT MAMMALIAN MICROSOMAL ENZYMES: PIPERONYL BUTOXIDE; PIPERONYL CYCLONENE; SULFOXIDE...

PRESUMABLY AS A RESULT OF INHIBITING LIVER ENZYMES, BOTH PIPERONYL BUTOXIDE & SULFOXIDE REDUCED THE RATE AT WHICH RADIOACTIVITY INTRODUCED IN THE FORM OF 7,10-(14)C-BENZPYRENE WAS CLEARED FROM THE BLOOD & EXCRETED IN THE BILE.

WHEN ADMINISTERED ORALLY, INTRAPERITONEALLY OR INTRAVENOUSLY PIPERONYL SULFOXIDE INTERFERRED WITH RAPID ELIMINATION OF INTRAVENOUSLY INJECTED 3,4-BENZPYRENE IN RATS.

For more Interactions (Complete) data for PIPERONYL SULFOXIDE (6 total), please visit the HSDB record page.

Ecotoxicity ValuesLD50 MALLARD DUCK ORAL GREATER THAN 2000 MG/KG, 4-MO OLD MALES
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=120-62-7]

Human Toxicity ExcerptsBECAUSE PIPERONYL BUTOXIDE & SULFOXIDE INHIBIT THE METABOLISM OF BENZPYRENE & BECAUSE OF THEIR CLOSE CHEMICAL SIMILARITY TO SESAMOL & SAFROLE, ALL METHYLENEDIOXYPHENYL SYNERGISTS ARE SUSPECT AS LIVER TUMORIGENS.
Carcinogen Classification · 6 件

Piperonyl sulfoxide

TR-124: Bioassay of Piperonyl Sulfoxide for Possible Carcinogenicity (CASRN 120-62-7) (1979 )

08/31/78

No Evidence

No Evidence

Clear Evidence

Non-Human Toxicity Excerpts · 5 件

SIGNS OF INTOXICATION /FOLLOWING ACUTE ORAL ADMIN TO MALLARD DUCKS/: WEAKNESS, GOOSE-STEPPING ATAXIA, ATAXIA, OCCASIONAL STUMBLING OR FALLING, WINGS HELD VERY HIGH ON BODY. SIGNS WERE SEEN AS SOON AS 25 MIN AFTER TREATMENT & PERSISTED FOR UP TO 14 DAYS. /SAMPLE PURITY 88%/

NON-TOXIC TO RATS FED FOR 15 MONTHS WITH DIET CONTAINING 0.2%.

THE SUBSTANCE HAS A LOW MAMMALIAN TOXICITY (RAT ORAL LD50 2 G/KG). TOXIC SYMPTOMS WHICH MAY APPEAR IN 10 TO 20 MIN INCLUDE TREMORS & CENTRAL NERVOUS DEPRESSION. EVEN SURVIVING ANIMALS MAY EXPERIENCE PROLONGED COMA.

INTRAPERITONEAL INJECTION OF PIPERONYL BUTOXIDE INTO MICE INITIALLY DECREASED & THEN INCREASED LEVELS OF LIVER MICROSOMAL CYTOCHROME P-450. THE BIPHASIC EFFECT IN VIVO WAS ACCOMPANIED BY SPECIFIC CHANGES IN THE SPECTRA OF P-450-DRUG INTERACTION IN VITRO. THE IN VIVO ADMINISTRATION ALSO PRODUCED A P-450 DIFFERENCE SPECTRUM WHEN DITHIONITE-REDUCED MICROSOMES FROM TREATED ANIMALS WERE COMPARED AT DIFFERENT PH VALUES. THIS SPECTRUM WAS ALSO PRODUCED IN VITRO BY PIPERONYL SULFOXIDE.

For more Non-Human Toxicity Excerpts (Complete) data for PIPERONYL SULFOXIDE (7 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 5 件

1. WASH CONTAMINATING PESTICIDE FROM THE EYE WITH COPIOUS AMOUNTS OF WATER. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FOR LIFE-THREATENING ALLERGIC REACTION TO PYRETHRUM (SEVERE ASTHMA OR ANAPHYLAXIS), GIVE 0.1 TO 0.5 ML OF 1:1000 ADRENALIN INTRAMUSCULARLY, OR SLOWLY INTRAVENOUSLY. REPEAT IF NECESSARY TO RELIEVE RESPIRATORY DISTRESS & MAINTAIN BLOOD PRESSURE. INTRAVENOUS AMINOPHYLLINE (10 ML, SLOWLY) MAY BE INDICATED. GIVE HYDROCORTISONE (50-100 MG), OR EQUIVALENT STEROID, INTRAVENOUSLY. LESS SEVERE REACTIONS (RHINITIS) CAN BE MANAGED WITH ANTIHISTAMINES & DECONGESTANTS, GIVEN ORALLY. HYPERSENSITIVITY PNEUMONITIS MAY REQUIRE OXYGEN, STEROIDS, ANTIBIOTICS & SEVERAL DAYS BEDREST, DEPENDING ON SEVERITY. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/

3. INGESTION OF SMALL AMOUNT OF PYRETHRIN OR PYRETHROID FORMULATION IS NOT LIKELY TO CAUSE POISONING. EXAMINE LABEL TO IDENTIFY ADDITIONAL INSECTICIDES, WHICH MAY BE MORE TOXIC. BASE TREATMENT ON THE MOST TOXIC INGREDIENTS. A. IF FORMULATION CONTAINS ONLY PYRETHRINS, OR PYRETHROIDS, & SYNERGISTS, INGESTION OF A SMALL AMOUNT (UP TO ABOUT 5 MG/KG) IS PROBABLY BEST TREATED BY LARGE DOSES OF ACTIVATED CHARCOAL.../PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/, FOLLOWED BY CATHARTIC DOSES OF SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG BODY WEIGHT IN 1-6 OZ WATER. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/

4. IF LARGE AMOUNTS OF PYRETHRIN OR PYRETHROIDS FORMULATION HAVE BEEN INGESTED, THE STOMACH & INTESTINE MUST BE EVACUATED: A. IF VICTIM IS ALERT & RESPIRATION IS NOT DEPRESSED, GIVE SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER, TO INDUCE VOMITING (ADULTS & CHILDREN 12 YEARS & OLDER: 30 ML; CHILDREN UNDER 12 YEARS: 15 ML). CAUTION: OBSERVE VICTIM CLOSELY AFTER ADMINISTERING IPECAC. IF CONSCIOUSNESS LEVEL DECLINES OR VOMITING HAS NOT OCCURRED IN 15 MINUTES, INTUBATE THE STOMACH IMMEDIATELY. FOLLOWING EMESIS, HAVE VICTIM DRINK SUSPENSION OF...ACTIVATED CHARCOAL /PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/ TO LIMIT ABSORPTION OF TOXICANT REMAINING IN THE GUT. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/

B. IF VICTIM...NOT FULLY ALERT, EMPTY STOMACH IMMEDIATELY BY INTUBATION, ASPIRATION, & LAVAGE /PRC: WATER IN CHILDREN & SALINE IN ADULTS/... BECAUSE MANY PESTICIDES ARE DISSOLVED IN PETROLEUM DISTILLATES, EMESIS & INTUBATION OF THE STOMACH INVOLVE RISK THAT SOLVENT WILL BE ASPIRATED, LEADING TO CHEMICAL PNEUMONITIS. FOR THIS REASON: (A) IF VICTIM IS UNCONSCIOUS OR OBTUNDED & FACILITIES ARE AT HAND, INSERT AN ENDOTRACHEAL TUBE (CUFFED, IF AVAILABLE) PRIOR TO GASTRIC INTUBATION. (B) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING INTUBATION & LAVAGE /PRC: WATER IN CHILDREN & SALINE IN ADULTS/ (TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD). KEEP VICTIM'S HEAD TURNED TO LEFT. (C) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. (D) AFTER ASPIRATION OF GASTRIC CONTENTS & WASHING OF STOMACH, INSTILL...ACTIVATED CHARCOAL.../PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/ THROUGH STOMACH TUBE TO LIMIT ABSORPTION... (E) IF BOWEL MOVEMENT HAS NOT OCCURRED IN 4 HR & PATIENT IS FULLY CONSCIOUS, GIVE SODIUM OR MAGNESIUM SULFATE AS CATHARTIC... /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/

National Toxicology Program Studies · 1 件

A bioassay of technical-grade piperonyl sulfoxide for possible carcinogenicity was conducted by administering the test chemical in feed to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats of each sex were administered piperonyl sulfoxide in the diet at one of several doses, either 1,500 or 3,000 ppm for the males and either 3,000 or 6,000 ppm for the females, for 105 weeks. Matched controls consisted of 20 untreated rats of each sex. All surviving rats were killed at the end of the period of administration of the test chemical. Groups of 50 male mice were administered one of two doses, either 350 or 700 ppm, for 104 or 105 weeks. Groups of 50 female mice were initially administered one of two doses, either 700 or 1,400 ppm. Due to excessive weight depression in the dosed female mice, the doses for this sex were reduced after week 20 to 200 and 600 ppm, respectively, and administration of the test chemical at the lower doses was continued for 84 or 85 weeks. The time-weighted average doses for the females were 295 and 754 ppm. Matched controls consisted of 20 untreated mice of each sex. All surviving mice were killed at the end of the period of administration of the test chemical. ... It is concluded that under the conditions of this bioassay, technical-grade piperonyl sulfoxide was not carcinogenic for male or female Fischer 344 rats or for female B6C3F1 mice, but was carcinogenic for male B6C3F1 mice, producing an increased incidence of hepatocellular carcinomas. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Positive; Female Mice: Negative.

Non-Human Toxicity ValuesLD50 Rat oral 2 g/kg

安全データ

毒性
LD50 in adult male, female rats (mg/kg): 3957, 3477 orally (Gaines, Linder)
有毒物質データの
120-62-7(Hazardous Substances Data)
Formulations/Preparations
USED IN CONJUCTION WITH PYRETHRINS FOR AEROSOL PREPARATIONS, GENERALLY AT 1% WITH 0.2% PYRETHRINS OR ALLETHRIN. PRO-NOXFISH--2.5% ROTENONE & 2.5% SULFOXIDE.
General Manufacturing Information · 3 件

/SYNERGISTIC PROPERTIES DISCOVERED BY/ SYNERHOLM ET AL, CONTRIBS BOYCE THOMPSON INST 15, 35 (1947); SYNERHOLM, US PATENT 2,486,579 (1949 TO BOYCE THOMPSON INST FOR PLANT RES).

SULFOXIDE: PRODUCT DISCONTINUED BY PENICK CORP.

OF SLIGHT INSECTICIDAL PROPERTIES BUT MAINLY USED AS SYNERGIST FOR PYRETHRINS, ALLETHRIN WITH ROTENONE AS FISH TOXICANT.

応用分野 · 3 件

解説一般式R-SO-R'(R,R'はアルキル基,フェニル基など)で表される有機化合物.

使用Insecticide synergist.

一般的な説明Clear pale yellow to amber viscous liquid with a sweetish smell.

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補足説明

定義An organic compound of general formula RSOR′, where R and R′ are organic radicals. An example is dimethyl sulfoxide, (CH3)2SO, commonly used as a solvent.

5. DO NOT ADMINSTER OR INSTILL MILK, CREAM, OR OTHER SUBSTANCES CONTAINING VEGETABLE OR ANIMAL FATS, WHICH ENHANCE ABSORPTION OF LIPOPHILIC SUBSTANCES, SUCH AS PYRETHRINS & PYRETHROIDS. 6. DIAZEPAM...5-10 MG IN ADULTS, 0.1 MG/KG IN CHILDREN, GIVEN ORALLY OR SLOWLY IV, SHOULD CONTROL NERVOUSNESS & TREMORS IN RARE CASES HAVING SYMPTOMS AFTER EXTRAORDINARY EXPOSURE TO PYRETHRINS & PYRETHROIDS. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/