2

In addition to an incomplete exposure pathway based on the use pattern, piperalin has a low total 

usage amount nationally and a relatively limited geographic use. Therefore, EFED has 

determined that a full ecological risk assessment for piperalin is not necessary based on de 

minimis exposure. 

This document summarizes the available use, environmental fate, and toxicity data submitted for 

piperalin and highlights potential areas of concern or uncertainty for the single currently 

registered use.

Based on the indoor-only use pattern for piperalin and EPA's determination that when the 

fungicide is used according to the label there is an incomplete exposure pathway and, therefore, 

no environmental exposure, the Agency makes a No Effects (NE) determination for all listed 

species as well as a No Habitat Modification determination for all designated critical habitats for 

the currently registered use of piperalin.

The expectation of no exposure, and therefore no risk, to non-target organisms in this assessment 

is based on the presumption that piperalin use is limited to indoors, as is specified on the label. 

However, if contaminated potting soil is composted outdoors (although piperalin should be 

highly adsorbed to soil) or contaminated water is washed out of the greenhouse into surface 

waters, the assessment might not be protective. Therefore, it is recommended that the label 

state that any potential runoff from contaminated potting soil or water discharged from a

greenhouse be contained by a hydrologically isolated site that does not produce runoff 

capable of entering any irrigation or drainage ditch, canal, or other body of water.

If, in the future, piperalin is considered for additional uses that could result in environmental 

releases, further analysis will need to be undertaken to determine potential effects to non-target 

organisms, including listed species and their designated critical habitat.
3

REGISTRATION REVIEW

Preliminary Ecological Risk Assessment and Endangered Species Effects Determination for:

Piperalin

(CAS Reg. No. 3478-94-2; USEPA PC Code 097003)

3-[2-methylpiperidino]propyl 3,4-dichlorobenzoate

Prepared by:

Scott Glaberman, Ph.D., Biologist

Cheryl Sutton, Ph.D., Environmental Scientist

Reviewed by:

Thomas Steeger, Ph.D., Senior Science Advisor

Jim Carleton, Ph.D., Senior Fate Scientist 

Sarah Winfield, Acting Branch Chief

U. S. Environmental Protection Agency

Office of Pesticide Programs

Environmental Fate and Effects Division

Environmental Risk Branch IV

1200 Pennsylvania Ave., NW

Mail Code 7507P

Washington, DC 20460

March 10, 2014
4

TABLE OF CONTENTS

Problem Formulation .................................................................................................... 5

Nature of Regulatory Action....................................................................................................... 5

Previous Assessments................................................................................................................. 5

Ecological Risk Assessments...................................................................................... 5

Drinking Water Exposure Assessments...................................................................... 5

Stressor Source and Distribution ................................................................................................ 5

Pesticidal Mechanism of Action ................................................................................. 5

Overview of Pesticide Use and Usage ........................................................................ 6

Environmental Fate and Transport ............................................................................................. 6

Ecological Effects....................................................................................................................... 9

Degradate Toxicity Predictions................................................................................. 10

Ecological Incidents.................................................................................................. 10

Characteristics of Ecosystems Potentially at Risk .................................................... 11

Conceptual Model..................................................................................................... 11

Analysis .................................................................................................................................... 12

Endangered Species Assessment .............................................................................................. 12

Endocrine Disruptor Screening Program.................................................................................. 12

References................................................................................................................................. 13

Appendix. ECOSAR Predicted Toxicity Results for Piperalin and Transformation Products. 18
5

PROBLEM FORMULATION

Nature of Regulatory Action

As part of the implementation of the Registration Review program pursuant to Section 3(g) of 

FIFRA, the Agency is evaluating all current and active registrations for piperalin (3-[2-

methylpiperidino]propyl 3,4-dichlorobenzoate) to determine whether it continues to meet the 

FIFRA standard for registration. The structure of this risk assessment is based on guidance 

contained in U.S. EPA’s Guidance for Ecological Risk Assessment (USEPA, 1998a), taking into 

account criteria presented by the Office of Pesticide Program’s Science Policy Council/Risk 

Management Forum De Minimis Subgroup. 

Previous Assessments

Ecological Risk Assessments

Piperalin was first registered in the United States in 1964 to treat powdery mildew fungal 

infections of ornamental plants in greenhouses. The sole current registrant is SePRO 

Corporation (Carmel, IN). In support of the Reregistration Eligibility Decision (USEPA 1994a), 

an Ecological Risk Assessment (ERA) was conducted (USEPA, 1994b) which concluded that 

there is no significant risk to non-target terrestrial and aquatic organisms based on the exclusive 

indoor commercial greenhouse use pattern. 

Drinking Water Exposure Assessments

A drinking water exposure assessment (DWA) in support of a human health risk assessment has 

not been conducted in the past based on the indoor-only (greenhouse) use pattern and consequent 

low likelihood of human exposure through drinking water sources. Similarly, a DWA is not 

being conducted as part of Registration Review.

Stressor Source and Distribution

Piperalin is a fungicide used to control powdery mildew fungal infections of ornamental plants, 

ornamental woody shrubs and vines, and trees grown in commercial greenhouses. There is one 

end-use product, Pipron®(EPA Reg. # 67690-1; 84.4% a.i.), which is formulated as a soluble 

concentrate/liquid and applied as a foliar spray inside greenhouses. 

The current stamped label (dated 8/7/2007) was accepted by EPA with the condition that the 

label specifies: “For use only in commercial greenhouses and similar enclosed structures with 

nonporous coverings used for the production of ornamental crops for resale.” 

Pesticidal Mechanism of Action
6

Piperalin’s mechanism of action is inhibition of growth and ergosterol biosynthesis in fungal 

sporidia (Schyneegurt and Henry, 1992). 

Overview of Pesticide Use and Usage

Piperalin is supplied as a soluble concentrate/liquid in a single end-use product (Pipron®Liquid 

Concentrate), and is applied by high-volume, high-pressure foliar spray to ornamentals only in 

commercial greenhouses with an impermeable roof or similar structures. It may not be applied 

using an irrigation system. Application rates on a per acre basis are not available. The label 

allows up to 8 fluid ounces of the liquid concentrate product (0.5 lbs a.i.) to be mixed with 100 

gallons of water, but does not specify the volume to be applied nor does it limit the number of 

repeat applications. Thus, a maximum application rate cannot be determined from information 

on the label. However, based on information from the registrant (submitted to the Agency in 

November 2009 as comments upon the opening of the docket EPA-HQ-OPP-2009-0483 for 

Registration Review of piperalin), both the median and 90th percentile use rates are equivalent to

0.125 lb a.i./A. Piperalin may only be used on ornamentals. 

Comprehensive past usage data are not available, but sales data indicate that a relatively low 

quantity of piperalin is applied annually. Additionally, the piperalin use is somewhat 

geographically limited. Based on information presented in the EPA docket for the Registration 

Review of piperalin (http://www.regulations.gov/#!documentDetail;D=EPA-HQ-OPP-2009-

0483-0018), during the one-year period of 10/1/08 to 9/30/09, piperalin was only sold in five states, 

i.e., CA, FL, MA, TX and UT, with approximately 86% of sales in California. Based on information 

from the California Department of Pesticide Regulation (CDPR), total pounds of piperalin applied

annually in California during the years 2005-2007 ranged from 2,123 to 2,428 lbs.

Environmental Fate and Transport

A summary of the physical/chemical properties and the environmental fate properties of 

piperalin is provided in Table 1. Due to the greenhouse-only use of piperalin, several standard

environmental fate studies were not required, as this use pattern does not require submission of 

such data under Part 158 Subpart N of Title 40 of the Code of Federal Regulations (abbreviated 

40CFR1581). 

 

1 CFR 2014. Code of Federal Regulations Title 40 (Protection of the Environment), Part 158 (Data Requirements 

for Pesticides), Subpart N (Environmental Fate). http://www.ecfr.gov/cgi-bin/textidx?tpl=/ecfrbrowse/Title40/40cfr158_main_02.tpl
7

Table 1. Physical/chemical properties and environmental fate properties of piperalin.

Chemical/Fate parameter Value Source (MRID)

Chemical Structure 

Molecular Weight (g/mol) 330.25

Vapor Pressure (Torr; at 25 °C) < 1.0 x 10-7 USEPA 2009

Octanol-water Partition Coefficient (Log KOW) 4.3 USEPA 2009

Water Solubility (mg/L; at 25 °C) 20 USEPA 2009

Hydrolysis half-lives (25C)

pH 5 t1/2 = 714 d

pH 7 t1/2 = 16.4 d

pH 9 t1/2 = 0.20 d

40407501

43922803

Aqueous photolysis half-life Not reviewed (not an applicable data 

requirement for this use type) 41335801

Soil photolysis half-life Not reviewed (not an applicable data 

requirement for this use type) 41335802

Aerobic soil metabolism half-life (pH = 5.5, 

24°C)

t1/2 = 96, 100 d (two radiolabels) 41425201

43922803

Anaerobic soil metabolism half-life (pH = 5.5) t1/2 = 33.8, 38.1 d (two radiolabels) 41425202

43922803

Aerobic aquatic metabolism half-life No data NA

Anaerobic aquatic metabolism half-life No data NA

Freundlich adsorption coefficient (KF; in L/kg); 

Parent:

520 (1/n=0.78; clay loam; 2% o.m.)

305 (1/n=0.87; loam; 1.8% o.m.)

62.3 (1/n=0.73; sandy loam; 1.4% 

o.m.)

27.6 (1/n=0.93; sand;0.5% o.m.)

42493001

DCBA1:

0.2 (1/n=0.67)

2.04 (1/n=0.90)

1.10 (1/n=0.74)

1.19 (1/n=0.73)

43922801

MPPA2:

0.69 (1/n=0.93)

0.84 (1/n=1.1)

1.1 (1/n=0.96)

3.8 (1/n=1.4)

43922802
8

Table 1. Physical/chemical properties and environmental fate properties of piperalin.

Chemical/Fate parameter Value Source (MRID)

Organic carbon-normalized Freundlich adsorption 

coefficient (KFOC; in L/kgOC )

Parent:

44824 

29212

7672

9516

42493001

DCBA1:

67

120

157

70

43922801

MPPA2:

41

120

380

225

43922802

Fish bioconcentration and bioaccumulation 

factors (BCF/BAF)

BCF: ~1000x

BAF: ~1000x

USEPA 2009; Estimated 

with KABAM model

1 Major hydrolytic degradate 2,3-dichlorobenzoic acid

2 Major hydrolytic degradate 3-(2-methylpiperidino)propyl alcohol

Piperalin is soluble in water up to 20 mg/L at 25C and is not expected to volatilize significantly 

due to the compound’s low vapor pressure of <1 x 10-7Torr at 25C (USEPA 1994). Piperalin is 

slightly mobile in low organic carbon soils and hardly mobile in other soils, based on the FAO 

classification scheme, with organic carbon-normalized Freundlich adsorption coefficients (KFOC)

that range from 7672 to 44824 L/kgOC for four soils (MRID 42493001). 

The most significant decay mechanism under most environmental conditions is expected to be 

hydrolysis (abiotic and microbially mediated). Piperalin is susceptible to rapid hydrolysis under 

alkaline conditions and hydrolyzes more slowly under neutral conditions, but is relatively stable 

under acidic conditions (MRIDs 40407501, 43922803). In soil, piperalin degrades slowly under 

aerobic conditions (t1/2 = 98, 100 d for two radiolabels in one soil type; MRID 41425201) and 

somewhat more rapidly under anaerobic conditions (t1/2 = 34, 38 d for two radiolabels in one soil 

type; MRID 41425202). Because both test soils were acidic (pH 5.5), more rapid degradation 

would be expected in more alkaline soils due to more rapid hydrolysis at higher pH levels. 

Aquatic metabolism data are not available and are not required for the greenhouse use pattern. 

Photodegradation data were submitted in 1989 but were not reviewed; the data are not required 

for the greenhouse use pattern.

Even though there are no empirical data on the bioconcentration or bioaccumulation of piperalin 

in aquatic ecosystems, a log Kow > 4 indicates a potential for bioaccumulation if water 

contamination should occur. Based on a log Kow of 4.3, the Kow-based Aquatic Bioaccumulation 

Model (KABAM; http://www.epa.gov/oppefed1/models/water/models4.htm) was used to 

estimate that bioaccumulation could occur in aquatic ecosystems, with factors of approximately 

1000x for various size classes of fish with the major route of accumulation occurring through

respiration (USEPA, 2009). However, based on the lack of a complete exposure pathway from 
9

the use site to non-target aquatic organisms, ecological effects associated with bioaccumulation 

of piperalin are not expected.

Two major degradates of piperalin were identified in hydrolysis, aerobic and anaerobic soil 

studies: the de-esterification products 2,3-dichlorobenzoic acid (DCBA) and 3-(2-

methylpiperidino)propyl alcohol (MPPA). Maximum concentration information for these 

degradates is presented in Table 2. Both degradates are more mobile than the parent with KF

values ranging from 1.1 to 2.0 L/kgOC in three soils and 0.2 in one soil for DCBA (MRID 

43922801), and from 0.7 to 3.8 for MCPA (MRID 43922802). The adsorption of the degradates 

is not well correlated with the organic matter content of the soils studied, so the Koc model may 

not accurately describe soil mobility across multiple soils for the degradates.

Table 2. Maximum concentration of piperalin degradates in environmental fate studies.

Chemical Name MRID Study Type Maximum Concentration 

(Time)/Final Concentration (time)

2,3-dichlorobenzoic 

acid (DCBA)

40407501 Hydrolysis

pH 9: 5.2 μg/mL (12 hours; EOS)

pH 7; 4.7 μg/mL (34 days; EOS)

pH 5; 0.1 μg/mL (34 days; EOS)

41425201 Aerobic Soil Metabolism 21% (day 14)/48.5% (180)

41425202 Anaerobic Soil Metabolism 58% (day 60; EOS)

3-(2-methylpiperidino)

propyl alcohol (MPPA)

41425201 Aerobic Soil Metabolism 10.7% (day 3)/2.9% (180)

41425202 Anaerobic Soil Metabolism 14% (day 60; EOS)

carbon dioxide (CO2) 41425201 Aerobic Soil Metabolism 48.5% (day 180; EOS)

EOS = End of study.

Ecological Effects

Effects to Aquatic Organisms

Piperalin is classified as highly toxic to freshwater fish and moderately toxic to freshwater

invertebrates (Table 3) on an acute exposure basis. No chronic toxicity data are available for

freshwater aquatic animals. In addition, no data are available to describe the toxicity of piperalin

to estuarine/marine fish or invertebrates, or aquatic vascular or nonvascular plants.

Table 3. Summary of most sensitive endpoints from submitted aquatic toxicity studies for 

piperalin.

Species

(common name)

Taxa 

Represented

EndpointDuration

(hours)

Mean 

Concentration 

(μg a.i./L)

Citation

MRID

Study 

Classification

Lepomis macrochirus

(Bluegill Sunfish)

Freshwater fish 

and aquaticphase 

amphibians

LC50 96

770

(highly toxic) 43012201 Acceptable

Daphnia magna

(Water Flea)

Freshwater 

Invertebrates LC50 48

1890

(moderately 

toxic)

40407504 Acceptable
10

Effects to Terrestrial Organisms 

Piperalin is classified as practically non-toxic to birds on a sub-acute dietary exposure basis and 

slightly toxic to mammals on an acute oral exposure basis (Table 4). There are no data on the 

chronic effects of piperalin on birds or mammals. There are no data on the effects of piperalin to 

terrestrial plants. Piperalin is practically non-toxic to honey bees (Apis mellifera) on an acute 

contact exposure basis.

Table 4. Summary of most sensitive endpoints from submitted terrestrial toxicity studies 

for piperalin (NR=not reported). 

Species 

(common 

name)

Taxa 

Represented

Endpoint

Mean 

Concentration

Test 

Substance 

(% a.i.)

Citation 

MRID

Acute 

Toxicity 

Classification

Rattus 

norvegicus

(Fisher 344 

Rat)

Mammals LD50

800 mg/kg (female)

1419 mg/kg (male)

99 40503201 Slightly toxic

Colinus 

virginianus

(Northern 

Bobwhite 

Quail) 

Birds LC50 > 5,380 mg/kg-diet 99 40407502 Practically 

non-toxic

Apis 

mellifera

(Honey Bee)

Terrestrial 

insects LD50 >36.26 μg/bee1 NR 00018842 Practically non-toxic

1 Two percent mortality occurred at the highest concentration tested (36.26 μg/bee)

Degradate Toxicity Predictions

Ecological effects data are not available for the two major degradates of piperalin, DCBA and 

MPPA. In order to compare potential toxicity of transformation products to the parent, estimated 

toxicity data for piperalin and degradates were generated using quantitative structure-activity 

relationships (QSAR) derived in the program ECOSAR (version 1.11) (see Appendix A for 

program output). QSAR estimates for the parent compound for fish acute toxicity (LC50 range: 

625 to 810 μg a.i./L) are very similar to the empirical endpoint for piperalin (LC50 = 770 μg 

a.i./L), regardless of whether these estimates are based on a specific chemical class (i.e., aliphatic 

amines) or baseline toxicity (i.e., neutral organics). QSAR estimates of the toxicity of piperalin 

to daphnids overestimate the empirical endpoint for piperalin (LC50 = 1890 μg a.i./L) based on 

the class aliphatic amines (LC50 = 154 μg a.i./L), but were more accurate for the ester class (LC50

= 1070 μg a.i./L). Overall, QSAR toxicity predictions suggest that degradates are either of equal 

or lower toxicity than the parent compound across fish, aquatic invertebrates, and algae. 

Ecological Incidents
11

A review of the Ecological Incident Information System (EIIS) maintained by the Agency’s 

Office of Pesticide Programs (OPP) in January 2014 indicates that there are no reported 

ecological incidents associated with the use of piperalin. A review of OPP’s Incident Data 

System (IDS) in February 2014 indicates that there was one incident in which the product 

Pipron® was associated with minor damage to plants. A search of the American Bird 

Conservancy’s Avian Incident Monitoring System (AIMS) Database in January 2014 did not 

indicate any reported incidents in birds involving the use of piperalin. In general, an absence of 

reported incidents cannot be construed as the absence of incidents though. 

Characteristics of Ecosystems Potentially at Risk

As previously discussed, piperalin is registered for use only in enclosed commercial greenhouses 

with impermeable roofs and, as such, exposure to non-target aquatic and terrestrial organisms is 

not expected. As such, no ecosystem is likely to be at risk from the indoor use of this compound.

Conceptual Model

For a pesticide to pose an ecological risk, it must reach ecological receptors in biologically 

significant concentrations. An exposure pathway is the means by which a pesticide moves in the 

environment from a source to an ecological receptor. For an ecological pathway to be complete, 

it must have a source, a release mechanism, an environmental transport medium, a point of 

exposure for ecological receptors, and a feasible route of exposure.

The conceptual model for piperalin provides a written description and visual representation of 

the predicted relationships between piperalin, potential routes of exposure, and the predicted 

effects for the assessment endpoint. A conceptual model consists of two major components: risk 

hypothesis and a conceptual diagram (USEPA 1998).

Risk Hypothesis

A risk hypothesis describes the predicted relationship among the stressor, exposure, and 

assessment endpoint response along with the rationale for their selection. For piperalin, the 

following ecological risk hypothesis is being employed for this ecological risk assessment:

Piperalin, when used indoors in accordance with the label, is not expected to result in 

adverse effects on the survival, growth, and reproduction of non-target terrestrial and/or

aquatic organisms (plants and animals).

Conceptual Diagram

A conceptual diagram/model is established for chemicals with likely outdoor environmental 

exposure pathways. This is not the case for piperalin, which is used indoors and does not have 

outdoor uses. As such, this problem formulation does not depict a conceptual diagram for the 

indoor use of piperalin. 
12

For the sole currently registered use of piperalin, potential ecological exposure is expected to be 

de minimis based on the lack of a complete exposure pathway from the use site to non-target 

terrestrial and aquatic organisms. 

Analysis

The use, environmental fate, and ecological effects are characterized and integrated to assess the 

risks. This is accomplished using a risk quotient (RQ; ratio of exposure concentration to effects 

concentration) approach when possible. When a RQ approach is not possible, risks are assessed 

qualitatively. Because piperalin is used indoors only, and in a relatively low quantity on a 

national basis, environmental exposure is not expected. Therefore, risk to non-target listed and 

non-listed organisms will not be assessed. 

Endangered Species Assessment

Based on the indoor-only use pattern for piperalin, and EPA's determination that, when piperalin 

is used according to the label, environmental exposure is not expected, the Agency makes a No 

Effects (NE) determination for all listed species and a No Habitat Modification determination for 

all designated critical habitats for the currently registered use of piperalin within greenhouses.

If, in the future, piperalin is considered for additional uses that could result in environmental 

exposures, further analysis will need to be undertaken to determine potential effects to listed 

species and their designated critical habitat.

Endocrine Disruptor Screening Program

As required by FIFRA and FFDCA, EPA reviews numerous studies to assess potential adverse 

outcomes from exposure to chemicals. Collectively, these studies include acute, subchronic and 

chronic toxicity, including assessments of carcinogenicity, neurotoxicity, developmental, 

reproductive, and general or systemic toxicity. These studies include endpoints which may be 

susceptible to endocrine influence, including effects on endocrine target organ histopathology, 

organ weights, estrus cyclicity, sexual maturation, fertility, pregnancy rates, reproductive loss, 

and sex ratios in offspring. For ecological hazard assessments, EPA evaluates acute tests and 

chronic studies that assess growth, developmental and reproductive effects in different 

taxonomic groups. As part of the most recent registration decision for piperalin, EPA reviewed 

these data and selected the most sensitive endpoints for relevant risk assessment scenarios from 

the existing hazard database. However, as required by FFDCA section 408(p), piperalin is 

subject to the endocrine screening part of the Endocrine Disruptor Screening Program (EDSP). 

EPA has developed the EDSP to determine whether certain substances (including pesticide 

active and other ingredients) may have an effect in humans or wildlife similar to an effect 

produced by a “naturally occurring estrogen, or other such endocrine effects as the Administrator 

may designate.” The EDSP employs a two-tiered approach to making the statutorily required 

determinations. Tier 1 consists of a battery of 11 screening assays to identify the potential of a 

chemical substance to interact with the estrogen, androgen, or thyroid (E, A, or T) hormonal 

systems. Chemicals that go through Tier 1 screening and are found to have the potential to 

interact with E, A, or T hormonal systems will proceed to the next stage of the EDSP where EPA 
13

will determine which, if any, of the Tier 2 tests are necessary based on the available data. Tier 2 

testing is designed to identify any adverse endocrine-related effects caused by the substance, and 

establish a dose-response relationship between the dose and the E, A, or T effect. 

Under FFDCA section 408(p), the Agency must screen all pesticide chemicals. Between 

October 2009 and February 2010, EPA issued test orders/data call-ins for the first group of 67 

chemicals, which contains 58 pesticide active ingredients and 9 inert ingredients. A second list 

of chemicals identified for EDSP screening was published on June 14, 20132and includes some 

pesticides scheduled for registration review and chemicals found in water. Neither of these lists 

should be construed as a list of known or likely endocrine disruptors. 

For further information on the status of the EDSP, the policies and procedures, the lists of 

chemicals, future lists, the test guidelines and the Tier 1 screening battery, please visit our 

website.3

Uncertainties

The expectation of no exposure to non-target organisms in this assessment is based on the 

presumption that piperalin use is limited to indoors, as specified on the label. However, if 

contaminated potting soil is composted outdoors (although piperalin should be highly adsorbed

to soil) or contaminated water is washed out of the greenhouse into surface waters, the 

assessment might not be protective, and there would be uncertainty as to the potential adverse 

effect of piperalin on non-target organisms due to exposure.

References

FAO. 2000. Appendix 2. Parameters of pesticides that influence processes in the soil. In FAO 

Information Division Editorial Group (Ed.), Pesticide Disposal Series 8. Assessing Soil 

Contamination. A Reference Manual. Rome: Food & Agriculture Organization of the 

United Nations (FAO). 

Schyneegurt, M.A. and M.J. Henry. 1992. Effects of piperalin and fenpropidin on sterol 

biosynthesis in Ustilago maydis. Pesticide biochemistry and physiology 43: 45-52.

USEPA. 1994a. USEPA. 1994a. Reregistration Eligibility Decision (RED) Piperalin. Office of 

Pesticide Programs, United States Environmental Protection Agency. Washington, D.C. 

July 1994. (EPA 738-R-94-033)

USEPA. 1994b. USEPA. 1994b. Piperalin RED (Reregistration Eligibility Document). (sic) 

Environmental Fate and Effects Division, Office of Pesticide Programs, United States 

Environmental Protection Agency. Washington, D.C. September 1994. (DP Barcodes: 

183913, 200603).

 

2

See http://www.regulations.gov/#!documentDetail;D=EPA-HQ-OPPT-2009-0477-0074 for the final second list of 

chemicals.

3

http://www.epa.gov/endo/
14

USEPA. 1998a. Guidance for Ecological Risk Assessment. Risk Assessment Forum. 

EPA/630/R-95/002F, April 1998.

USEPA. 2004. Overview of the Ecological Risk Assessment Process in the Office of Pesticide 

Programs. Office of Prevention, Pesticides, and Toxic Substances. Office of Pesticide 

Programs. Washington, D.C. January 23, 2004.

USEPA. 2007b. Ecological Incident Information System. 

http://www.epa.gov/espp/consultation/ecorisk-overview.pdf.

USEPA. 2009. Registration Review: Preliminary Problem Formulation for Ecological Risk, 

Environmental Fate, Endangered Species, and Drinking Water Assessments for Piperalin. 

Office of Pesticide Programs, United States Environmental Protection Agency. 

Washington, D.C. May 28, 2009. (DP Barcode: 364402)

U.S. Fish and Wildlife Service (USFWS) and National Marine Fisheries Service (NMFS). 1998. 

Endangered Species Consultation Handbook: Procedures for Conducting Consultation 

and Conference Activities Under Section 7 of the Endangered Species Act. Final Draft. 

March 1998.
15

Environmental Fate Studies

161-1 Hydrolysis

MRID Citation Reference

93185018 Registrant 

summary

Environ Corp. (1990) Elanco Products Co. Phase 3 Summary of MRID 

40407501. Hydrolysis of Piperalin in Buffer Solution: Study No. AAC8718. 

Prepared by Lilly Research Laboratories. 10 p. 

40407501 2067281 Koenig, D.K. 1987 Hydrolysis of Piperlin in Buffer Solution

161-2 Photodegradation-water

MRID Citation Reference

41335801 DER not 

located

Dykes, J. (1989) Determination of the Photolysis Rate of [Carbon-14]-piperalin 

in Aqueous Solution: ABC Final Report 37686; 211/EWPHOT/US. Unpublished 

study prepared by Analytical Bio-Chemistry Laboratories, Inc. 34 p. 

161-3 Photodegradation-soil

MRID Citation Reference

41335802 DER not 

located

Jackson, S.; Kesterson, A.; Lawrence, L. (1989) Soil Surface Photolysis of 

[Carbon-14] Piperalin in Natural Sunlight: Lab Project No. 353; Report 1219; 

211/ESPHOT/AM. Unpublished study prepared by Pharmacology and 

Toxicology Research Laboratory. 68 p. 

162-1 Aerobic soil metabolism

MRID Citation Reference

41425201 2067282 Rainey, D. (1990) Aerobic Soil Metabolism of ?Carbon 14| Piperalin: Lab I.D. 

Number ABC0430. Unpublished study prepared by DowElanco, Plant Science 

Chemical Development. 33 p. 

162-2 Anaerobic soil metabolism

MRID Citation Reference

41425202 2067283 Rainey, D. (1990) Anaerobic Soil Metabolism of ?Carbon 14| Piperalin Lab I.D. 

Number: ABC0431. Unpublished study prepared by DowElanco, Plant Science 

Chemical Development. 32 p. 

163-1 Leach/adsorp/desorption

MRID Citation Reference

41425203 2067284 Saunders, D. (1990) Piperalin Aged Soil Leaching Study: Lab I.D. Number: 

DGS8902. Unpublished study prepared by DowElanco, Plant Science Chemical 
16

Development. 37 p. 

42493001 2067285 Saunders, D.; Powers, F. (1988) Adsorption and Desorption of Piperalin on Soil: 

Lab Project Number: EWD8729. Unpublished study prepared by Lilly Research 

Laboratories. 63 p. 

43922801 2067286 Kennard, L.; Saunders, D. (1996) Soil Adsorption and Desorption of 2,3-

Dichlorobenzoic Acid, a Degradate of Piperalin: Lab Project Number: 

ENV95138. Unpublished study prepared by DowElanco North American 

Environmental Chemistry Lab. 82 p. 

43922802 2067287 Sanders, L.; Saunders, D. (1996) Soil Adsorption and Desorption of 3-(2-

Methylpiperidino)proply Alcohol, a Degradate of Piperalin: Lab Project Number: 

ENV95139. Unpublished study prepared by DowElanco North American 

Environmental Chemistry Lab. 84 p. 

Non-Guideline

43922803

Reviewed with 

43922801 and 802

2067289 Saunders, D.; Powers, F. (1996) Confirmation of Degradates of Piperalin: Lab 

Project Number: ENV95140. Unpublished study prepared by DowElanco North 

American Environmental Chemistry Lab. 84 p. 

Ecological Effects Studies

71-2 Avian Dietary Toxicity

MRID Citation Reference

40407502 2067291 Negilski, D.; Meyerhoff, R. (1987) The Toxicity of Piperalin to Juvenile 

Bobwhite in a Five-day Dietary Study: Laboratory Pro- ject ID: A00487. 

Unpublished study prepared by Lilly Research Laboratories. 38 p. 

93185004 Summary of 

above

Environ Corp. (1990) Elanco Products Co. Phase 3 Summary of MRID 

40407502. The Toxicity of Piperalin to Juvenile Bobwhite in a Five-Day Dietary 

Study: Study No. AOO487. Prepared by Lilly Research Laboratory. 15 p. 

72-1 Acute Toxicity to Freshwater Fish

MRID Citation Reference

124479 What animals? Worth, H.; Gibson, W.; Anderson, R. (1965) Acute Toxicity Studies in Animals 

with Pipron E.C. (Unpublished study received Nov 29, 1965 under 1471-58; 

submitted by Elanco Products Co., Div. of Eli Lilly and Co., Indianapolis, IN; 

CDL:006295-A) 

40407503 2067292

invalidated

Negilski, D.; Grothe, D.; Seacat, J. (1987) Acute Toxicity of Pi- peralin to 

Bluegill (Lepomis macrochirus) in a Flow-through Test System: Laboratory 

Project ID: F01287. Unpublished study pre- pared by Lilly Research 

Laboratories. 36 p. 

43012201 2067294 Weinberg, J.; Kirk, H.; Miller, J.; et al. (1993) Evaluation of the Acute Toxicity 

of Piperalin to the Bluegill, Lepomis macrochirus Rafinesque: Lab Project 

Number: DECO-ES-2722. Unpublished study prepared by Dow Chemical 

Environmental Toxicity & Chemistry Research Lab. 27 p. 
17

40098001 2049421 Mayer and Ellersieck, USFWS - Goldfish LC50 

93185005 Summary of 

above

Environ Corp. (1990) Elanco Products Co. Phase 3 Summary of MRID 

40407503. Acute Toxicity of Piperalin to Bluegill (Lepomis macrochirus) in a 

Flow-Through Test System: Study NO.F01287. Prepared by Lilly Research 

Laboratories. 12 p. 

72-2 Acute Toxicity to Freshwater Invertebrates

MRID Citation Reference

40407504 2067293 Negilski, D.; Grothe, D.; Mohr, R. (1987) Acute Toxicity of Pipera- lin to 

Daphnia magna in a Static-renewal Test System: Laboratory Project ID: C00887. 

Unpublished study prepared by Lilly Re- search Laboratories. 36 p. 

93185006 Summary of 

above

Environ Corp. (1990) Elanco Products Co. Phase 3 Summary of MRID 

40407504. Acute Toxicity of Piperalin to Daphnia magna in a Static-Renewal 

Test System: Study No.C00887. Prepared by Lilly Research Laboratories. 12 p. 
18

Appendix. ECOSAR Predicted Toxicity Results for Piperalin and Transformation 

Products.

(Piperalin)

SMILES: CC1CCCCN1CCCOC(=O)c2cc(CL)c(CL)cc2

CHEM: Piperalin

MOL FOR: C16 H21 CL2 N1 O2

MOL WT : 330.26

Log Kow: 5.08 (KowWin estimate)

Wat Sol: 20 mg/L (experimental database)

ECOSAR v1.00 Class(es) Found

------------------------------

ECOSAR Class Organism Duration End Pt mg/L (ppm)

=========================== ================== ======== ====== ==========

Aliphatic Amines : Fish 96-hr LC50 0.810

Aliphatic Amines : Daphnid 48-hr LC50 0.154

Aliphatic Amines : Green Algae 96-hr EC50 0.180

Aliphatic Amines : Fish ChV 0.018

Aliphatic Amines : Daphnid ChV 0.020

Aliphatic Amines : Green Algae ChV 0.032

Aliphatic Amines : Fish (SW) 96-hr LC50 0.887

Aliphatic Amines : Mysid Shrimp (SW) 96-hr LC50 0.136

Aliphatic Amines : Green Algae (SW) 96-hr EC50 0.175

Aliphatic Amines : Fish (SW) ChV 0.018

Aliphatic Amines : Mysid Shrimp (SW) ChV 0.020

Aliphatic Amines : Green Algae (SW) ChV 0.033

Esters : Fish 96-hr LC50 0.775

Esters : Fish 14-day LC50 1.094

Esters : Daphnid 48-hr LC50 1.070

Esters : Green Algae 96-hr EC50 0.327

Esters : Fish 32/33-d ChV 0.033

Esters : Daphnid 21-day ChV 0.305

Esters : Green Algae ChV 0.225

Esters : Fish (SW) 96-hr LC50 0.850

Esters : Mysid Shrimp 96-hr LC50 0.220

Esters : Fish (SW) ChV 0.222 !

Esters : Mysid Shrimp (SW) ChV 0.026

Esters : Earthworm 14-day LC50 436.285 *

=========================== ================== ======== ====== ==========

Neutral Organic SAR : Fish 96-hr LC50 0.625

(Baseline Toxicity) : Daphnid 48-hr LC50 0.524

 : Green Algae 96-hr EC50 0.800

 : Fish ChV 0.055 

 : Daphnid ChV 0.083

: Green Algae ChV 0.509=

Note: * = asterisk designates: Chemical may not be soluble

enough to measure this predicted effect.

Note:! = exclamation designates: The toxicity value was determined from a predicted 

SAR using established acute-to-chronic ratios and ECOSAR regression techniques which 

are documented in the supporting Technical Reference Manual. When possible, this 

toxicity value should be considered in a weight of evidence approach.
19

(DCBA)

SMILES : OC(=O)c1cccc(CL)c1CL

CHEM : DCBA

MOL FOR: C7 H4 CL2 O2 

MOL WT : 191.01

Log Kow: 2.82 (KowWin estimate)

Wat Sol: 189.4 mg/L (WskowWin estimate)

ECOSAR v1.00 Class(es) Found

------------------------------

Neutral Organics-acid

 Predicted

ECOSAR Class Organism Duration End Pt mg/L (ppm)

=========================== ================== ======== ====== ==========

--> Acid moeity found: Predicted values multiplied by 10

Neutral Organics-acid : Fish 96-hr LC50 279.034*

Neutral Organics-acid : Fish 14-day LC50 285.893*

Neutral Organics-acid : Daphnid 48-hr LC50 177.647

Neutral Organics-acid : Green Algae 96-hr EC50 120.443

Neutral Organics-acid : Fish 30-day ChV 30.715

Neutral Organics-acid : Daphnid ChV 23.455

Neutral Organics-acid : Green Algae ChV 52.773

Neutral Organics-acid : Fish (SW) 96-hr LC50 364.474*

Neutral Organics-acid : Mysid Shrimp 96-hr LC50 154.932

Neutral Organics-acid : Fish (SW) ChV 65.141

Neutral Organics-acid : Mysid Shrimp (SW) ChV 10.500

Neutral Organics-acid : Earthworm 14-day LC50 2729.851*

Note: * = asterisk designates: Chemical may not be soluble

 enough to measure this predicted effect.

(MPPA)

SMILES : C1CCCCN(C(C1)C)CCCO

CHEM : MPPA

MOL FOR: C11 H23 N1 O1 

MOL WT : 185.31

Log Kow: 2.32 (KowWin estimate)

Wat Sol: 5551 mg/L (WskowWin estimate)

ECOSAR v1.00 Class(es) Found

------------------------------

Aliphatic Amines

 Predicted

ECOSAR Class Organism Duration End Pt mg/L (ppm)

=========================== ================== ======== ====== ==========

Aliphatic Amines : Fish 96-hr LC50 20.993

Aliphatic Amines : Daphnid 48-hr LC50 2.260

Aliphatic Amines : Green Algae 96-hr EC50 1.075

Aliphatic Amines : Fish ChV 0.372

Aliphatic Amines : Daphnid ChV 0.020

Aliphatic Amines : Green Algae ChV 0.392

Aliphatic Amines : Fish (SW) 96-hr LC50 22.458

Aliphatic Amines : Mysid Shrimp (SW) 96-hr LC50 2.133

Aliphatic Amines : Green Algae (SW) 96-hr EC50 1.052

Aliphatic Amines : Fish (SW) ChV 0.372
20

Aliphatic Amines : Mysid Shrimp (SW) ChV 0.020

Aliphatic Amines : Green Algae (SW) ChV 0.376

=========================== ================== ======== ====== ==========

Neutral Organic SAR : Fish 96-hr LC50 77.022

(Baseline Toxicity) : Daphnid 48-hr LC50 46.178

 : Green Algae 96-hr EC50 22.671

 : Fish ChV 7.261

 : Daphnid ChV 4.511

: Green Algae ChV 8.693

Note: * = asterisk designates: Chemical may not be soluble

 enough to measure this predicted effect.