United States
                  Environmental Protection
                  Agency
                                 Office of Pesticides and Toxic Substances
                                 Office of Pesticide Programs (H7508C)
                                 Washington, DC 20460
ŁEPA     Pesticide
                   Fact   Sheet
                                                         540/FS-89-040
                   Name of Chemical:  ROTENONE
                   ReaSOn  for  Issuance:  Registration Standard

                   Date lssued:0ctober 1> 1988
                   Fact Sheet  Number:  198
        1.   DESCRIPTION OF CHEMICAL
            Common name:
              Rotenone  (and associated  resins)
           Chemical Name:
            Other Chemical
            nomenclature:
              (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.
                          (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-(1-methylethenyl)-
                          [2R-(2a,6a,alpha, 12a alpha)]-(1Jbenzopyrano
                          (3,4-b)furo(2,3-h)-(1)benzopyran-6 (6aH)-one.

                          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
Other Names:
            EPA Pesticide Chemical Code
               (Shaughnessy Number):
                          71003 - rotenone; 71004 - cube'
                          resins other than rotenone;
                          71001 - derris resins.
            Year of Initial Registration:  1947

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     Pesticide Type: Botanical

     Prodi.cers: Penick-Bio UCLAF 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 Premises:  Cats and Dogs.

 Livestock:  Cattle (Beef and Dairy), Goats, Horses, Sheep,
   and Swine.

 Household:  Flying and crawling insects.

 Commercial and Industrial Uses:  Flying and crawling insects.

 Methods of Application:  Dusts, sprays,  dips,  and pumping
   liquid formulations into bodies of water.

 Annual Usage:  50,000 to 120,000 Ib

 Predominant Usage:  Aquatic (piscicide); agriculture
   (potatoes, tomatoes,  pears, apples); livestock,  pets,  and
   household

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 Formulations:  The following formulations are registered
   0.4-5% dusts; up to 5% wettable powders (WP); up to 0.55
   Ib/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/lquid (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:

     Molecular Weight:  394.4

     Color: colorless (rotenone, purity 99.5%)

     Physical State:  Crystalline solid

     Specific Gravity:  1.27 at 20" *C

     Melting Point:  165-166 *C

     Solubility:  Water 0.00002 g/100 ml at 20 *C; Ethyl alcohol
     0.2 g/100 ml at 20 *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 *C; Ethylene dichloride 33.0 g/100 ml at 20
     *C; Chloroform 47.2 g/100 ml at 20 *C; Acetone 6.6 g/100
     ml at 20 *C; Benzene 8.0 g/100 ml at 20 *C; Chlorobenzene
     13.5 g/100 ml at 20*C.

     Stability: Decomposes rapidly in organic solvents exposed to
                light and air.

     Toxicology Characteristics
                              i

     Acute oral LD (rat): LDso =39.5 +/- 2.21 mg/kg
     for female rats 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.

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• 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
  effects.

* 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 cells  in vitro without met
  activation.  No mutations were induced in mice in_ v\/o by
  rotenone.  No chromosomal effects  were observed in"ra~Es
  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
   Mallard       2200mg/kg
   Pheasant       1680mg/kg

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       Fish Acute
      Rainbow Trout     22.5 ppb
      Channel Catfish    2.6-2.8 ppb
      Bluegill          22.5 ppb
      Aquatic Invertebrate
      Daphnia maona  (Water  fleas) 2.1 ug/1
      (21  Day EC50)
    TOLERANCES

      Currently,  use of  rotenone or derris or cube'  roots
      on growing  crops is exempt from the requirement of tolerences,
      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.

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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 for terrestrial (food
      and non-food) and domestic outdoor uses must include the follow-
      ing  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 for 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 hazarddous to aquatic organisns in adjacent sites. Do
      not contaminate untreated water when disposing of equipment washwaters.

            Products containing rotenone intended for use to kill fish
      fish must include the following statement on the label:
         "This pesticide is toxic to fish.  Fishkills are expected at
      recomended 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.


   CONTACT PERSON AT EPA

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

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      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 fulf
data requirements for pesticide registration and reregistration.

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&EPA
     United States'
     Environmental Protection Agency
     Office of Pesticide Program (H7502C)
     PMSD. Information Services Branch
     401 M Street. SW.
     Washington. DC 20460
     Official Business
     Penalty for Private Use S300
First-Class Bulk
Postage and Fees Paid
EPA
Permit No. G-35     t

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