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rotenone EPA Pesticide Fact Sheet 10/88

EPA Pesticide Fact Sheet

Name of Chemical:  ROTENONE
Reason for Issuance:  Registration Standard 
Date Issued:  October 7, 1988
Fact Sheet Number: 198


                     1.  DESCRIPTION OF CHEMICAL

- Common name:  Rotenone (and associated resins)
- Chemical Name:  (2R, 6aS, 12aS)-1,2,6,6a,12,12a-hexahydro-2-
  isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one.
- Other Chemical nomenclature:  (R)-1,2-dihydro-8,9-dimethoxy-2-
  (1-methylethenyl)[1]benzopyrano[3,4-b] furo[2,3-h][1]benzopyran-6,12-
  dione (9th Collective Index); 1,2,12,12a alpha- tetrahydro-2a-
  isopropenyl-8,9-dimethoxy[1] benzopyranol[3,4-b]furo[2,3-h]
  [1]benzopyran-6 (6aH)-one (8th Collective Index); 1,2,12,12a-
  tetrahydro-8,9-dimethoxy-2  methylethenyl)- [2R-(2a,6a,alpha, 12a
  alpha)]-(1)benzopyrano (3,4-b)furo(2,3-h)-(1)benzopyran-6 (6aH)-one.
- Other Names:  aker-root; Chem Fish; Derris; derris root; Nicouline;
  Rotacide; Protex; Tubatoxin; and tuba-root; ENT-133; Barbasco; Cube;
  Haiari; Nekos; and Timbo.
- Chemical Abstracts Service (CAS) Number:  83-79-4
- EPA Pesticide Chemical Code (Shaughnessy Number):  71003 - rotenone;
  71004 - cube resins other than rotenone; 71001 - derris resins.
- Year of Initial Registration:  1947
- Pesticide Type:  Botanical
- Producers:  Penick-Bio UCLXF Corporation and Prentiss Drug and
  Chemical Company

                    2. USE PATTERNS AND FORMULATION

Registered Uses:

- Terrestrial Food Crops:  Rotenone is registered for  foliar preharvest
  application to vegetables, berries, tree fruit, nuts, forage crops,
  and sugarcane.
- In addition to foliar applications, delayed dormant applications are
  made to deciduous tree fruit.
- Soil applications may be made to vegetable crops, berries and tree
  nuts.
- Terrestrial Nonfood Crop:  Ornamentals, turf, shade trees, and
  tobacco.
- Greenhouse Food Crop:  Vegetables.
- Greenhouse Nonfood:  Ornamentals.
- Aquatic Non-Food Crop:  Fish.
- Domesticated Pets and Their Man-made Premise:  Cats and Dogs.
- Livestock:  Cattle (Beef and Dairy), Goats, Horses, Sheep, and Swine.
- Household:  Flying and crawling insects.
- Commercial and Industrial Use:  Flying and crawling insects.
- Methods of Application:  Dust, sprays, dips, and pumping liquid
  formulations into bodies of water.
- Annual Usage:  50,000 to 120,000 lb
- Predominant Usage:  Aquatic (piscicide); agriculture (potatoes,
  tomatoes, pears, apples); livestock, pets, and household
- Formulations:  The following formulations are registered 0.4-5% dusts;
  up to 5% wettable powders (WP); up to 0.55 lb/gal emulsifiable
  concentrate (EC); up to 1.25% soluble concentrate/liquid (SC/L); up to
  5%; wettable powder/dust (WP/D) up to 2.5%;emulsifiable concentrate
  (EC); up to 1.5%; soluble concentrate/liquid (SC/L); ready-to-use
  (RTU) at 0.1% or less; and up to 0.1% pressurized liquid (PrL).


                      3. SCIENCE FINDINGS

Chemical/Physical Characteristics of Rotenone (purity 99.5% or
unspecified) and its associated resins:

- Empirical Formula:  C23H2206
- Molecular Weight:  394.4
- Color: colorless (rotenone, purity 99.5%)
- Physical State:  Crystalline solid
- Specific Gravity:  1.27 at 20 degrees C
- Melting Point:  165-166 degrees C
- Solubility:  Water 0.00002 g/100 ml at 20 degrees C; Ethyl alcohol
  0.2 g/100 ml at 20 degrees C; Carbon tetrachloride 0.6 g/100 ml
  at 20-C; Amyl acetate 1.6 g/100 ml at 20-C; Xylene 3.4 g/100 ml at 20
  degrees C; Ethylene dichloride 33.0 g/100 ml at 20 degrees C;
  Chloroform 47.2 g/100 ml at 20 degrees C; Acetone 6.6 g/100 ml at 20
  degrees C; Benzene 8.0 g/100 ml at 20 degrees C; Chlorobenzene 13.5
  g/100 ml at 20 degrees C.
- Stability: Decomposes rapidly in organic solvents exposed to light and
  air.


Toxicology Characteristics

- Acute oral LD (rat): LD50 = 39.5 +/- 2.21 mg/kg for female rat and 
  102 +/- 12.6 mg/kg for male rats.
- 6 Month Feeding (dog): NOEL = 0.4 mg/kg/day; LEL - 2 mg/kg/day; levels
  tested 0, 0.4, 2, and 10 mg/kg/day.
- 2 Year Feeding (rat): NOEL = 7.5 ppm; LEL = 37.5 ppm; levels tested 0,
  7.5, 37.5 and 75 ppm.
- 2 Year Oncogenicity (rat): Negative for oncogenic effect.
- 2 Year Oncogenicity (mouse): Negative for oncogenic effects at doses
  below the MTD.
- Teratology (rat and mouse): No fetal effects at rates below NOEL for
  adults.
- Reproduction Toxicity (rat): Reproductive NOEL = 37.5 ppm; Maternal
  Toxicity NOEL = 7.5 ppm; levels tested 0, 7.5, 37.5, and 75 ppm.  No
  reproductive effects were noted.
- Gene Mutation: Rotenone did not induce gene mutations in bacteria or
  yeast, but it increased the frequency of gene mutations in mouse
  lymphoma cell in vitro without met.bolic activation.  No mutations
  were induced in mice in vivo by rotenone.  No chromosomal effects were
  observed in rats or mice treated with rotenone, and yeast treated with
  rotenone did not show increased mitotic recombination or mitotic gene
  conversion.


Physiological and Biochemical Characteristics

- Mechanism of pesticidal action:  Rotenone is an inhibitor of oxidative
  phosphorylation.


Environmental Characteristics

- Rotenone is rapidly degraded in soil and water with a half-life of 1-3
  days for both aerobic aquatic and anaerobic aquatic soils.


Ecological Characteristics:

- Avian Acute Oral LC50
    Mallard       2200mg/kg
    Pheasant      1680mg/kg

- Fish Acute LC50
    Rainbow Trout     22.5 ppb
    Channel Catfish   2.6-2.8 ppb
    Bluegill          22.5 ppb


- Aquatic Invertebrate EC50
    Daphnia magna (Water fleas) 2.1 ug/l (21 Day EC50)


TOLERANCES

- Currently, use of rotenone or derris or cube roots on growing crops is
  exempt from the requirement of tolerances, and neither tolerances nor
  exemptions exist for rotenone residues in animal commodities.


              4.  SUMMARY OF REGULATORY POSITION

   Rotenone is not being referred to Special Review because none of 
criteria for special review were met.

  Cranberry and piscicide uses are classified for restricted use. Users 
must consult their State Fish and Game Agency before applying rotenone 
products. Because of significant data gaps on the effects of rotenone in 
upland game birds, waterfowl, estuarine and marine organisms, a 
statement is required on all end-use products giving directions for use 
for killing fish.  The statement requires mandatory consultation with 
state or federal fish and wildlife agencies and will minimize effects on 
non-target organisms.

   The Agency is concerned about residues and metabolites of rotenone 
and associated resins in/on plants and animals. Data on the metabolism 
and nature of rotenone residues are needed to reevaluate the tolerance 
exemption.

   Water treated with rotenone must not be used as potable water or for 
irrigation of crops.  A restriction against use of rotenone within one 
half mile of potable water or irrigation intakes must be included on 
labels of products intended for use in cranberry bogs and for control of 
fish.  This statement will be an interim precaution until data on 
residues in water are available.

                 5. SUMMARY OF MAJOR DATA GAPS

- Toxicology:  Acute dermal toxicity, primary eye and skin irritation
  studies, dermal sensitization study, histological examination of the
  low and mid dose groups in the rat chronic feeding study.
- Environmental Fate:  Hydrolysis, photodegradation in water and on
  soil, aerobic soil and aquatic metabolism, leaching, terrestrial and
  aquatic field dissipation, confined rotational crop study, and
  irrigated crop accumulation.
- Environmental Safety:  Effects on upland game birds, waterfowl, and
  estuarine and marine organisms.
- Residue Chemistry:  Plant, livestock, and fish metabolism; method
  validation, residue data for each registered commodity and their
  processed products; food handling establishment residue data, and all
  product chemistry data.

                 6. LABELING REQUIREMENTS

   Products containing rotenone intended or terrestrial (food and non-
food) and domestic outdoor uses must include the following statement on 
the label:
    "This pesticide is toxic to fish.  Do not apply directly to water
     or wetlands (swamps, bogs, marshes, potholes).  Runoff and drift
     from treated areas may be hazardous to aquatic organisms in
     adjacent sites.  Do not contaminate untreated water when disposing
     of equipment washwater."

   Products containing rotenone intended or use in cranberry bogs must 
include the following statement on the label:
     "This pesticide is toxic to fish.  Runoff and drift from treated
      areas may be hazardous to aquatic organisms in adjacent sites. Do
      not contaminate untreated water when disposing of equipment
      washwaters."

   Products containing rotenone intended for use to kill fish must 
include the following statement on the label:
     "This pesticide is toxic to fish.  Fishkills are expected at
      recommended rates.  Consult your State Fish and Game Agency before
      applying this product to public waters to determine if a permit
      is needed for such an application.  Do not contaminate untreated
      water when disposing of equipment washwaters."


                         7. CONTACT PERSON AT EPA

Phillip Hutton, PM 17
Insecticide-Rodenticide Branch
Registration Division (TS-767C)
Washington, DC 20460
(703) 557 2690


      or

Paul Schroeder
PM Team 17
Insecticide-Rodenticide Branch
Registration Division (TS-767C)
Washington, DC 20460
(703) 557-2602


DISCLAIMER:  The information presented in this Chemical Information Fact 
Sheet is a summary only and may not be used to fulfil data requirements 
for pesticide registration and reregistration.