75552 Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices

ENVIRONMENTAL PROTECTION

AGENCY

[OPPTS–41054; FRL–6594–7]

Forty-Sixth Report of the TSCA

Interagency Testing Committee to the

Administrator; Receipt of Report and

Request for Comments

AGENCY: Environmental Protection

Agency (EPA).

ACTION: Notice.

SUMMARY: The Toxic Substances Control

Act (TSCA) Interagency Testing

Committee (ITC) transmitted its FortySixth Report to the Administrator of the

EPA on May 25, 2000. In the 46th

Report, which is included with this

notice, the ITC: Solicits information on

uses, exposures, ecological effects,

environmental fate, and health effects

on 3 classes of structurally related

chemicals (4 polychlorophenols and

polychlorobenzenethiols, 8

chlorotrifluoromethylphenoxy

benzenes, and 50 perfluorinated

chemicals) that have potential to persist

and bioconcentrate; requests more

detailed exposure and use information

be included in the TSCA Electronic

Hazard and Safety Data Reporting Form;

adds 8 nonylphenol polyethoxylate

degradation products to the Priority

Testing List; and removes 4

alkylphenols and 15 alkylphenol

ethoxylates from the Priority Testing

List.

EPA invites interested persons to

submit written comments on the Report.

DATES: Comments, identified by docket

control number OPPTS–41054, must be

received on or before January 2, 2001.

ADDRESSES: Comments may be

submitted by mail, electronically, or in

person. Please follow the detailed

instructions for each method as

provided in Unit I. of the

SUPPLEMENTARY INFORMATION. To ensure

proper receipt by EPA, it is imperative

that you identify docket control number

OPPTS–41054 in the subject line on the

first page of your response.

FOR FURTHER INFORMATION CONTACT: For

general information contact: Barbara

Cunningham, Acting Director,

Environmental Assistance Division

(7408), Office of Pollution Prevention

and Toxics, Environmental Protection

Agency, 1200 Pennsylvania Ave., NW.,

Washington, DC 20460; telephone

number: (202) 554–1404; e-mail address:

TSCA-Hotline@epa.gov.

For technical information contact:

John D. Walker, ITC Executive Director

(7401), Environmental Protection

Agency, 1200 Pennsylvania Ave., NW.,

Washington, DC 20460; telephone

number:(202) 260–1825; fax: (202) 260–

7895; e-mail address:

walker.johnd@epa.gov.

SUPPLEMENTARY INFORMATION:

I. General Information

A. Does this Action Apply to Me?

This notice is directed to the public

in general. It may, however, be of

particular interest to you if you

manufacture (defined by statute to

include import) and/or process TSCAcovered chemicals and you may be

identified by the North American

Industrial Classification System

(NAICS) codes 325 and 32411. Because

this notice is directed to the general

public and other entities may also be

interested , the Agency has not

attempted to describe all the specific

entities that may be interested in this

action. If you have any questions

regarding the applicability of this action

to a particular entity, consult the

technical person listed under FOR

FURTHER INFORMATION CONTACT.

B. How Can I Get Additional

Information, Including Copies of this

Document or Other Related Documents?

1. Electronically. You may obtain

electronic copies of this document, and

certain other related documents that

might be available electronically, from

the EPA Internet Home Page at http://

www.epa.gov/. To access this

document, on the Home Page select

‘‘Laws and Regulations,’’ ‘‘Regulations

and Proposed Rules,’’ and then look up

the entry for this document under the

‘‘Federal Register—Environmental

Documents.’’ You can also go directly to

the Federal Register listings at http://

www.epa.gov/fedrgstr/.

You may also access additional

information about the ITC and the TSCA

testing program through the web site for

the Office of Pollution Prevention and

Toxics (OPPT) at http://www.epa.gov/

opptintr/, or go directly to the ITC Home

Page at http://www.epa.gov/opptintr/

itc/.

2. In person. The Agency has

established an official record for this

action under docket control number

OPPTS–41054. The official record

consists of the documents specifically

referenced in this action, any public

comments received during an applicable

comment period, and other information

related to this action, including any

information claimed as Confidential

Business Information (CBI). This official

record includes the documents that are

physically located in the docket, as well

as the documents that are referenced in

those documents. The public version of

the official record does not include any

information claimed as CBI. The public

version of the official record, which

includes printed, paper versions of any

electronic comments submitted during

an applicable comment period, is

available for inspection in the TSCA

Nonconfidential Information Center,

North East Mall Rm. B–607, Waterside

Mall, 401 M St., SW., Washington, DC.

The Center is open from noon to 4 p.m.,

Monday through Friday, excluding legal

holidays. The telephone number for the

Center is (202) 260–7099.

C. How and to Whom Do I Submit

Comments?

You may submit comments through

the mail, in person, or electronically. To

ensure proper receipt by EPA, it is

imperative that you identify docket

control number OPPTS–41054 in the

subject line on the first page of your

response.

1. By mail. Submit your comments to:

Document Control Office (7407), Office

of Pollution Prevention and Toxics

(OPPT), Environmental Protection

Agency, 1200 Pennsylvania Ave., NW.,

Washington, DC 20460.

2. In person or by courier. Deliver

your comments to: OPPT Document

Control Office (DCO) in East Tower Rm.

G–099, Waterside Mall, 401 M St., SW.,

Washington, DC. The DCO is open from

8 a.m. to 4 p.m., Monday through

Friday, excluding legal holidays. The

telephone number for the DCO is (202)

260–7093.

3. Electronically. You may submit

your comments electronically by e-mail

to: oppt.ncic@epa.gov, or mail your

computer disk to the address identified

above. Do not submit any information

electronically that you consider to be

CBI. Electronic comments must be

submitted as an ASCII file avoiding the

use of special characters and any form

of encryption. Comments and data will

also be accepted on standard disks in

WordPerfect 6.1/8.0 or ASCII file

format. All comments in electronic form

must be identified by docket control

number OPPTS–41054. Electronic

comments may also be filed online at

many Federal Depository Libraries.

D. How Should I Handle CBI

Information That I Want to Submit to

the Agency?

Do not submit any information

electronically that you consider to be

CBI. You may claim information that

you submit to EPA in response to this

document as CBI by marking any part or

all of that information as CBI.

Information so marked will not be

disclosed except in accordance with

procedures set forth in 40 CFR part 2.

In addition to one complete version of

Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices 75553

the comment that includes any

information claimed as CBI, a copy of

the comment that does not contain the

information claimed as CBI must be

submitted for inclusion in the public

version of the official record.

Information not marked confidential

will be included in the public version

of the official record without prior

notice. If you have any questions about

CBI or the procedures for claiming CBI,

please consult the technical person

listed under FOR FURTHER INFORMATION

CONTACT.

E. What Should I Consider as I Prepare

My Comments for EPA?

We invite you to provide your views

and comments on the ITC 46th Report.

You may find the following suggestions

helpful for preparing your comments:

1. Explain your views as clearly as

possible.

2. Describe any assumptions that you

used.

3. Provide copies of any technical

information and/or data you used that

support your views.

4. Provide specific examples to

illustrate your concerns.

5. Make sure to submit your

comments by the deadline in this

notice.

6. To ensure proper receipt by EPA,

be sure to identify the docket control

number assigned to this action in the

subject line on the first page of your

response. You may also provide the

name, date, and Federal Register

citation.

II. Background

The Toxic Substances Control Act

(TSCA) (15 U.S.C. 2601 et seq.)

authorizes the Administrator of the EPA

to promulgate regulations under TSCA

section 4(a) requiring testing of

chemicals and chemical groups in order

to develop data relevant to determining

the risks that such chemicals and

chemical groups may present to health

or the environment. Section 4(e) of

TSCA established the ITC to

recommend chemicals and chemical

groups to the Administrator of the EPA

for priority testing consideration.

Section 4(e) of TSCA directs the ITC to

revise the TSCA section 4(e) Priority

Testing List at least every 6 months.

1. The ITC’s 46th Report. The 46th

Report was received by the EPA

Administrator on May 25, 2000, and is

included in this notice. In the 46th

Report, the ITC:

i. Solicits information on uses,

exposures, ecological effects,

environmental fate, and health effects

on 3 classes of structurally related

chemicals (4 polychlorophenols and

polychlorobenzenethiols, 8

chlorotrifluoromethylphenoxy

benzenes, and 50 perfluorinated

chemicals) that have potential to persist

and bioconcentrate.

ii. Requests more detailed exposure

and use information be included in the

TSCA Electronic Hazard and Safety Data

Reporting Form.

2. Status of the Priority Testing List.

The current TSCA section 4(e) Priority

Testing List as of May 2000 can be found

in Table 1 of the 46th ITC Report which

is included in this notice. In the 46th

ITC Report, the ITC added 8

nonylphenol polyethoxylate

degradation products and removed 4

alkylphenols and 15 alkylphenol

ethoxylates from the Priority Testing

List.

List of Subjects

Environmental protection, Chemicals,

Hazardous substances.

Dated: November 20, 2000.

Charles M. Auer,

Director, Chemical Control Division, Office

of Pollution Prevention and Toxics.

Forty-Sixth Report of the TSCA

Interagency Testing Committee to the

Administrator, U.S. Environmental

Protection Agency

Table of Contents

Summary

I. Background

II. TSCA Section 8 Reporting

A. TSCA Section 8 Rules

B. ITC’s Use of TSCA Section 8 and ‘‘Other

Information’’

C. Promoting More Efficient Use of

Information Submission Resources

D. Request to Promulgate a TSCA Section

8(d) Rule

III. ITC’s Activities During This Reporting

Period (November 1999 to April 2000):

Information Solicitations

A. Polychlorophenols and

Polychlorobenzenethiols

B. Chlorotrifluoromethylphenoxy Benzenes

C. Perfluorinated Chemicals

IV. Revisions to the TSCA Section 4(e)

Priority Testing List

A. Chemicals Added to the Priority Testing

List: Nonylphenol Polyethoxylate

Degradation Products

B. Chemicals Removed from the Priority

Testing List: Alkylphenols and

Alkylphenol Ethoxylates

V. References

VI. The TSCA Interagency Testing Committee

Summary

This is the 46th Report of the TSCA

Interagency Testing Committee (ITC) to the

Administrator of the U.S. Environmental

Protection Agency (USEPA). The ITC

described Degradation Effects

Bioconcentration Information Testing

Strategies (DEBITS) in its 45th Report as

strategies to test for the availability of

degradation, ecological or human health

effects, and bioconcentration information for

chemicals with potential to persist,

bioconcentrate, and cause ecological or

health effects. The ITC implemented DEBITS

to identify three classes of structurally

related chemicals that have potential to

persist and bioconcentrate. These three

classes (and number of chemicals associated

with each class in parentheses) include

polychlorophenols and

polychlorobenzenethiols (4),

chlorotrifluoromethylphenoxy benzenes (8),

and perfluorinated chemicals (50). In this

Report the ITC is:

1. Soliciting uses, exposures, ecological

effects, environmental fate, and health effects

information on these three classes.

2. Requesting more detailed exposure and

use information be included in the TSCA

Electronic Hazard and Safety Data Reporting

Form.

3. Adding 8 nonylphenol polyethoxylate

degradation products to the Priority Testing

List.

4. Removing 4 alkylphenols and 15

alkylphenol ethoxylates from the Priority

Testing List.

The revised TSCA section 4(e) Priority

Testing List follows as Table 1.

TABLE 1.—THE TSCA SECTION 4(E) PRIORITY TESTING LIST (MAY 2000)

Report Date Chemical/group Action

28 May 1991 Chemicals with low confidence reference dose (RfD) Designated

Acetone

Thiophenol

30 May 1992 5 Siloxanes Recommended

31 January 1993 13 Chemicals with insufficient dermal absorption rate data Designated

32 May 1993 16 Chemicals with insufficient dermal absorption rate data Designated

35 November 1994 4 Chemicals with insufficient dermal absorption rate data Designated

37 November 1995 10 Alkylphenols and 2 alkylphenol polyethoxylates Recommended

39 November 1996 8 Nonylphenol ethoxylates Recommended

75554 Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices

TABLE 1.—THE TSCA SECTION 4(E) PRIORITY TESTING LIST (MAY 2000)—Continued

Report Date Chemical/group Action

41 November 1997 18 Alkylphenols, 5 polyalkylphenols and 6 alkylphenol polyethoxylates* Recommended

42 May 1998 3-Amino-5-mercapto-1,2,4- triazole* Recommended

42 May 1998 Glycoluril* Recommended

42 May 1998 Methylal* Recommended

42 May 1998 Ethyl silicate* Recommended

46 May 2000 8 Nonylphenol polyethoxylate degradation products* Recommended

* Data requested through the ITC’s Voluntary Information Submissions Innovative Online Network (VISION—see http://www.epa.gov/opptintr/

itc/vision.htm ).

I. Background

The ITC was established by section 4(e) of

the Toxic Substances Control Act (TSCA) ‘‘to

make recommendations to the Administrator

respecting the chemical substances and

mixtures to which the Administrator should

give priority consideration for the

promulgation of a rule for testing under

section 4(a)....At least every six months..., the

Committee shall make such revisions to the

Priority Testing List as it determines to be

necessary and transmit them to the

Administrator together with the Committee’s

reasons for the revisions’’ (Public Law 94–

469, 90 Stat. 2003 et seq., 15 U.S.C. 2601 et

seq.). Since its creation in 1976, the ITC has

submitted 45 semi-annual (May and

November) Reports to the EPA Administrator

transmitting the Priority Testing List and its

revisions. ITC Reports are available from the

ITC’s web site (http://www.epa.gov/opptintr/

itc) within a few days of submission to the

Administrator and from http://www.epa.gov/

fedrgstr after publication in the Federal

Register. The ITC meets monthly and

produces its revisions to the Priority Testing

List with administrative and technical

support from the ITC staff, ITC members, and

their U.S. Government organizations and

contract support provided by EPA. ITC

members and staff are listed at the end of this

Report.

II. TSCA Section 8 Reporting

A. TSCA Section 8 Rules

Following receipt of the ITC’s Report by

the EPA Administrator and addition of

chemicals to the Priority Testing List, the

EPA’s Office of Pollution Prevention and

Toxics (OPPT) promulgates TSCA section

8(a) Preliminary Assessment Information

Reporting (PAIR) and TSCA section 8(d)

Health and Safety Data (HaSD) rules for

chemicals added to the Priority Testing List.

These rules require producers and importers

of chemicals recommended by the ITC to

submit production and exposure reports

under TSCA section 8(a) and producers,

importers, and processors of chemicals

recommended by the ITC to submit

unpublished health and safety studies under

TSCA section 8(d). These rules are

automatically promulgated by OPPT unless

requested not to do so by the ITC.

B. ITC’s Use of TSCA Section 8 and ‘‘Other

Information’’

The ITC reviews the TSCA section 8(a)

PAIR reports, TSCA section 8(d) HaSD

studies and ‘‘other information’’ that

becomes available after the ITC adds

chemicals to the Priority Testing List. ‘‘Other

information’’ includes TSCA section 4(a) and

4(d) studies, TSCA section 8(c) submissions,

TSCA section 8(e) ‘‘substantial risk’’ notices,

‘‘For Your Information’’ (FYI) submissions,

ITC voluntary submissions, unpublished data

submitted to and from U.S. Government

organizations represented on the ITC,

published papers, as well as use, exposure,

effects, and persistence data that are

voluntarily submitted to the ITC by

manufacturers, importers, processors, and

users of chemicals recommended by the ITC.

The ITC reviews this information and

determines if data needs should be revised,

if chemicals should be removed from the

Priority Testing List or if recommendations

should be changed to designations.

C. Promoting More Efficient Use of

Information Submission Resources

The Voluntary Information Submissions

Innovative Online Network (VISION) is

accessible through the world wide web

(http://www.epa.gov/opptintr/itc/

vision.htm). VISION includes the Voluntary

Information Submissions Policy (VISP) and

links to the TSCA Electronic HaSD Reporting

Form (http://www.epa.gov/opptintr/.er/

hasd.htm). The VISP provides examples of

data needed by ITC member U.S.

Government organizations, examples of

studies that should not be submitted, the

milestones for submitting information,

guidelines for using the TSCA Electronic

HaSD Reporting Form and instructions for

electronically submitting full studies. The

TSCA Electronic HaSD Reporting Form is

used to provide electronic information on

ITC voluntary submissions, TSCA section

8(d) studies (to meet data needs of the ITC

member U.S. Government organizations), FYI

submissions, and TSCA section 8(e) studies.

In its 45th Report, the ITC stated that use

and exposure information should be

submitted through VISION using section 3.2

of the TSCA Electronic HaSD Reporting Form

(Confidential Business Information (CBI)

should NOT be submitted on the TSCA

Electronic HaSD Reporting Form). Since then

the ITC Director has received numerous

requests to provide more details on the type

of use and exposure information needed by

the ITC. In response to these requests, the

ITC asked EPA to include the following use

and exposure information in section 3.2 of

the TSCA Electronic HaSD Reporting Form:

• Manufacturing or processing procedures

(batch, continuous, closed, open, etc.).

• Product (raw-material, site-limited

intermediate, end-use, etc.).

• Type of end use (consumer product,

industrial product, consumer and industrial

product).

• Percent of chemical in end-use product.

• Average concentrations in air, water and

soil within the borders of manufacturing and

processing facilities.

• Number of people likely to be exposed

during chemical manufacturing and average

exposure concentrations.

• Number of people likely to be exposed

during chemical processing and average

exposure concentrations.

• Number of people likely to be exposed

during chemical use and average exposure

concentrations.

D. Request to Promulgate a TSCA Section

8(d) Rule

The ITC encourages producers, importers,

processors, and users of its recommended

chemicals to use VISION to voluntarily

provide electronic information and establish

a dialogue with the ITC to discuss needed

data. If the ITC does not receive voluntary

electronic information submissions to meet

its data needs, then it will ask the EPA to

promulgate a TSCA section 8(d) HaSD rule to

determine if there are unpublished data to

meet those needs. The ITC strongly

encourages those companies that must

respond to a TSCA section 8(d) rule to

provide data by using the TSCA Electronic

HaSD Reporting Form.

III. ITC’s Activities During This Reporting

Period (November 1999 to April 2000):

Information Solicitations

In its 45th Report, the ITC discussed its

strategies to screen chemicals for persistence

and bioconcentration potential (http://

www.epa.gov/opptintr/itc). These strategies

are referred to as Degradation Effects

Bioconcentration Information Testing

Strategies (DEBITS). DEBITS provides a

means to prioritize chemicals based on

degradation, ecological or human health

effects, and bioconcentration information.

Briefly the ITC screened 12,557 chemicals

and used criteria to identify 435 chemicals

with potential to persist and bioconcentrate

(see Figure 1 in 45th Report).

Since the 45th Report was delivered to the

EPA Administrator on November 30, 1999,

the ITC used DEBITS to further prioritize

these 435 chemicals. The ITC used DEBITS

to identify a subset of 112 chemicals with

bioconcentration factors (BCFs) >250. These

and structurally related chemicals with BCF

<250 were placed in chemical classes and

screened for the existence of ecological

effects, health effects, and environmental fate

Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices 75555

data. A BCF of 250 has been used by the EPA

as a lower ‘‘threshold’’ to identify substances

with potential to bioconcentrate. From these

112 chemicals, the ITC reviewed 42

chemicals which had BCF >250 and

production/importation volumes between

100,000 and 1,000,000 pounds reported in

response to the 1986, 1990, 1994, or 1998

EPA Inventory Update Rules. The ITC is

interested in identifying structurally related

classes of chemicals for testing which have

a suspicion of toxicity but lack adequate

screening data. The ITC is also interested in

utilizing Structure Activity Relationships

(SARs) to predict the toxicity of untested

chemicals in these structural classes.

Although High Production Volume (HPV)

chemicals with production/importation

volumes >1,000,000 pounds are expected to

have screening data developed as part of the

EPA’s HPV Chemical Challenge (http://

www.epa.gov/opptintr/chemrtk/

volchall.htm) and OECD SIDS (http://

www.oecd.org/) programs, they were

included in groups of structurally related

chemicals in order to provide additional

opportunities to develop SARs. In a few

instances, stucturally related chemicals not

previously identified by DEBITS were also

included in a chemical class, if there were

data useful for establishing SARs.

In this reporting period, three classes of

chemicals:

1. Polychlorophenols and

polychlorobenzenethiols.

2. Chlorotrifluoromethylphenoxy

benzenes.

3. Perfluorinated chemicals have emerged

from DEBITS as classes of specific interest.

The ITC is seeking information on uses,

exposures, health effects, and ecological

effects from the manufacturers, importers,

and processors of those chemicals in order to

determine whether any of them should be

added to the Priority Testing List. It is

requested that solicited information be

electronically submitted before August 29,

2000, consistent with the 90-day milestone of

the VISP (http://www.epa.gov/opptintr/itc/

visp.htm) for submitting data through the

TSCA Electronic HaSD Reporting Form.

DEBITS will continue to be implemented in

the future to prioritize chemicals with

potential to persist and bioconcentrate.

A. Polychlorophenols and

Polychlorobenzenethiols

1. Background. Polychlorophenols and

polychlorobenzenethiols includes

pentachlorothiophenol (Chemical Abstract

Service (CAS) number (No.) 133–49–3) and

tetrachloropyrocatechol (CAS No. 1198–55–

6). Pentachlorothiophenol is one of the 42

chemicals with BCF >250 and production/

importation volume between 100,000 and

1,000,000 pounds. Tetrachloropyrocatechol

is one of the 435 chemicals that satisfy the

DEBITS production/importation, persistence,

and bioconcentration potential criteria

described by the ITC in its 45th Report. The

ITC used available data for 2 structurally

related chemicals, pentachlorophenol (CAS

No. 87–86–5) and hexachlorobenzene (CAS

No. 118–74–1), to evaluate suspicion of

potential ecological and health effects of

pentachlorothiophenol and

tetrachloropyrocatechol.

Pentachlorothiophenol meets the DEBITS

criteria; it has an ultimate predicted aerobic

biodegradation rate of >2–3 months and an

estimated log octanol-water partition

coefficient of 5.91, and an estimated BCF of

7,066.There are limited health effects data on

pentachlorothiophenol except mild eye

irritation in the standard Draize test and an

intraperitoneal LD50 of 100 milligram/

kilogram (mg/kg) in mice. The ITC has no

ecological effects data on

pentachlorothiophenol. However,

pentachlorothiophenol is a metabolite of

hexachlorobenzene and pentachlorophenol.

It is formed as a result of glutathione

conjugation (Hahn et al, 1988, 1989; Linko et

al, 1986; Mehendale et al, 1975; Rozman et

al, 1977). It has been detected in the urine

of human populations exposed to

hexachlorobenzene (To-Figueras et al., 1992,

1997). The carcinogenicity, reproductive

effects, and development toxicities of

pentachlorophenol and hexachlorobenzene

are well known (ATSDR, 1996; Chhabra et

al., 1999). The ITC believes

pentachlorothiophenol may present a

suspicion of toxicity given the metabolic

relationship and structural similarity to

hexachlorobenzene and pentachlorophenol.

Tetrachloropyrocatechol also meets the

DEBITS criteria; it has an ultimate predicted

aerobic biodegradation rate of >2–3 months

and an estimated log octanol-water partition

coefficient of 4.29, and a measured BCF of

316–5,011.There is very little known about

the health effects of tetrachloropyrocatechol,

except for severe eye irritation in the Draize

tests and an oral LD50 in mice of 318 mg/kg.

However, tetrachloropyrocatechol is a

metabolite of pentachlorophenol. A fathead

minnow LC50 value of 1 mg/Liter (L) (highly

toxic) from 96-hour flow-through tests has

been reported (Russom et al., 1997) and six

TSCA section 8(d) studies were submitted

where tetrachloropyrocatechol was a

component of the test substance, biologically

treated bleached kraft mill effluent. It is

predicted to inhibit cellular respiration as an

uncoupler of oxidative phosphorylation. The

ITC believes tetrachloropyrocatechol may

present a suspicion of toxicity given the

metabolic relationship and structural

similarity to pentachlorophenol.

Information Profiles for

pentachlorothiophenol and

tetrachloropyrocatechol are posted on the

ITC’s web site (http://www.epa.gov/opptintr/

itc).

2. Information needs. The ITC needs more

information on uses and data on exposures,

environmental releases, pharmacokinetics,

subchronic toxicity, reproductive and

developmental effects, carcinogenicity, and

ecological effects for pentachlorothiophenol

and tetrachloropyrocatechol. The ITC also

needs mutagenicity data for

pentachlorothiophenol. If the information is

not voluntarily obtained, the ITC will

consider adding these chemicals to the

Priority Testing List in its next Report to the

EPA Administrator so that final TSCA

section 8(a) and 8(d) rules are promulgated

by EPA.

B. Chlorotrifluoromethylphenoxy Benzenes

1. Background. The

chlorotrifluoromethylphenoxy benzenes is a

structural class of eight chemicals that satisfy

the DEBITS persistence and bioconcentration

potential and production/importation criteria

described by the ITC in its 45th Report (Table

2). Four of the chlorotrifluoromethylphenoxy

benzenes are among the 42 chemicals with

BCF >250 and production/importation

volume between 100,000 and 1,000,000

pounds; p-toluidine, 5-chloro-

.alpha.,.alpha.,.alpha.-trifluoro-2-nitro-Nphenyl (CAS No. 1806–24–2) has a

production/importation volume <100,000

pounds.

TABLE 2.—CHLOROTRIFLUOROMETHYLPHENOXY BENZENES

CAS No. Chemical name HPV2

Estimated

BCF

Fish3 LC50

mg/L

NO2 on benzene ring

1806–24–2 p-Toluidine, 5-chloro-.alpha.,.alpha.,.alpha.-trifluoro-2-nitro-N-phenyl No 2380 2.22 Yes

42874–63–5 Phenol, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro- No 879 Yes

42874–96–4 Benzene, 2-chloro-1-(3-methylphenoxy)-4-(trifluoromethyl)- No 2696 1.96 No

77501–63–4 5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitro-2-ethoxy-1-methyl-2-

oxoethyl ester (lactofen)1

No 1009 Yes

88185–22–2 Benzoic acid, 3-[2-chloro-4-(trifluoromethyl)phenoxy]-, 2-ethoxy-1-methyl-2-oxoNo 1692 0.668 No

50594–44–0 Phenol, 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitro-, acetate1 Yes 362 0.39 Yes

50594–77–9 Phenol, 3-(2-chloro-4-(trifluoromethyl)phenoxy-), acetate1 Yes 500 0.17 No

63734–62–3 Benzoic acid,3-(2-chloro-4-(trifluoromethyl)phenoxy)-1 Yes 3 2.20 No

1 The ITC is not soliciting information on lactofen (077501–63–4) or HPV chemicals; ITC is relying on information from EPA’s HPV chemical

challenge program to provide data on HPV category chemicals.

75556 Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices

2 HPV = High Production Volume; chemicals with U.S. production/importation volumes >1 million pounds, e.g., those chemicals in EPA’s HPV

chemical challenge program (http://www.epa.gov/opptintr/chemrtk/volchall.htm).

3 Fish LC50 data are all from 96-hour flow though tests with fathead minnows using measured chemical concentrations.

One member of the class, lactofen (CAS

No. 77501–63–4) is a well-studied herbicide,

considered to be a probable human

carcinogen by the USEPA. Lactofen or 5-(2-

chloro-4-(trifluoromethyl)phenoxy)-2-nitro-2-

ethoxy-1-methyl-2-oxo ethyl ester was found

to increase the incidence of liver tumors in

CD-1 mice and hepatic neoplastic nodules

and preneoplastic focii in Sprague-Dawley

rats (PPG Industries, 1985a,b). On the basis

of these findings, the USEPA concluded that

lactofen met the critieria of a category B2

probable human carcinogen (http://

ace.orst.edu/cgi-bin/mfs/01/pips/

lactofen.htm). A number of other hepatic,

renal, and hematologic effects have been

reported in CD-1 mice, Sprague-Dawley rats,

and beagle dogs after repeated dosing.

Lactofen caused developmental effects in a 2-

generation reproductive study using CD rats

(PPG Industries, 1983) and when fed to

pregnant Sprague-Dawley rats (PPG

Industries, 1982). Lactofen was administered

in the diet for all these studies. Mixed results

have been obtained in genotoxicity testing.

As a result of the oncogenicity and other

adverse health effects associated with

lactofen, there is a heightened concern for

potential toxicity of the other seven

chlorotrifluoromethylphenoxy benzenes

which have not been as extensively

investigated.

Six chlorotrifluoromethylphenoxy

benzenes had fish LC50 values; all were less

than or equivalent to about 1 mg/L;

chemicals with LC50 values <1 mg/L are

considered ‘‘highly toxic’’ to aquatic

organisms. Four

chlorotrifluoromethylphenoxy benzenes had

a nitro group on the benzene ring (Table 2).

Estimates from the EPA’s Cancer Expert

System (Lai et al.,1996; Woo et al., 1995,

1998) suggested that

chlorotrifluoromethylphenoxy benzenes with

a nitro group on the benzene ring might have

higher carcinogenicity potential than

chlorotrifluoromethylphenoxy benzenes with

no nitro group on the benzene ring. Data are

needed to validate these suggestions. In

addition, the ITC has determined that health

effects data are indexed in TOXLINE or the

Registry of Toxic Effects of Chemical

Substances (RTECS) for three

chlorotrifluoromethylphenoxy benzenes:

Phenol, 5-(2-chloro-4-

(trifluoromethyl)phenoxy)-2-nitro- (CAS No.

42874–63–5); phenol, 3-(2-chloro-4-

(trifluoromethyl)phenoxy)-, acetate (CAS No.

50594–77–9); and benzoic acid, 3-(2-chloro4-(trifluoromethyl)phenoxy)- (CAS No.

63734–62–3). For the latter 2

chlorotrifluoromethylphenoxy benzenes

acute and genetoxicity studies were

submitted to the EPA as a result of a TSCA

section 8(d) rule that was promulgated for the

chlorotrifluoromethylphenoxy benzenes

(CAS No. 42874–96–4, 50594–77–9, and

63734–62–3) that were previously added to

the Priority Testing List in the ITC’s 29th

Report published in the Federal Register of

December 30, 1991 (56 FR 67424) (FRL–

4007–6) as trifluoromethyl diaryl ethers and

then removed from the Priority Testing List

in the 41st Report published in the Federal

Register of April 9, 1998 (63 FR 17658) (FRL–

5773–5). TOXLINE, RTECS, and TSCA

section 8(d) studies for phenol, 5-(2-chloro4-(trifluoromethyl)phenoxy)-2-nitro- (CAS

No. 42874–63–5); phenol, 3-(2-chloro-4-

(trifluoromethyl)phenoxy)-, acetate (CAS No.

50594–77–9); and benzoic acid, 3-(2-chloro4-(trifluoromethyl)phenoxy)- (CAS No.

63734–62–3) have been considered by the

ITC. An Information Profile for 5-(2-chloro-4-

(trifluoromethyl)phenoxy)-2-nitro- is posted

on the ITC’s web site (http://www.epa.gov/

opptintr/itc).

2. Information needs. The ITC needs

information on uses, exposures,

environmental releases, ecological effects,

pharmacokinetics, subchronic toxicity,

reproductive and developmental effects,

mutagenicity, and carcinogenicity for four

chlorotrifluoromethylphenoxy benzenes,

except lactofen and the three HPV chemicals

(Table 2). If the information is not voluntarily

obtained, the ITC will consider adding these

chemicals to the Priority Testing List in its

next Report to the EPA Administrator, so that

final TSCA section 8(a) and 8(d) rules are

promulgated by EPA.

C. Perfluorinated Chemicals

1. Background. The ITC is interested in 50

perfluorinated chemicals, because:

i. The carbon-fluorine bond is highly stable

and likely to persist.

ii. There is potential for long-range

atmospheric transport, persistence,

bioconcentration, and bioaccumulation.

iii. There are few publicly available data on

ecological effects, health effects, wildlife

exposures, or human exposures.

Forty-eight perfluorinated chemicals were

assigned to 10 structural classes while two

did not fit any structural class. Thirty-eight

perfluorinated chemicals satisfy the DEBITS

persistence (ultimate biodegradation >2–3

months) and bioconcentration potential (log

octanol-water partition coefficient 3–6) and

production/importation criteria described by

the ITC in its 45th Report. An additional 12

(identified by an asterisk in Tables 3, 4, 7, 10,

and 11) were selected from TSCA section 8(e)

submissions because they were structurally

related to the 38 perfluorinated chemicals

and may be useful in developing SARs. The

12 structurally related perfluorinated

chemicals from TSCA section 8(e)

submissions include chemicals that:

i. Are present in human and animal blood.

ii. Are pesticide active ingredients.

iii. Cause tumors and developmental

toxicity in animal studies.

iv. Are metabolites of the 38 perfluorinated

chemicals that satisfy the DEBITS criteria.

Estimated BCFs and Henry’s Law

Constants (HLCs) for perfluorinated

chemicals were based on associated or nonhydrolyzed chemical structures. Estimated

BCFs for the 50 perfluorinated chemicals

range from 3 to 26,000. HLCs ranged from 103

to 10-10 atm m3/mole. Approximately half of

the perfluorinated chemicals had estimated

HLCs >10-2 atm m3/mole, suggesting they

could evaporate and be susceptible to longrange transport. The perfluoroalkyl iodides

are likely to undergo rapid photolysis in the

atmosphere, leading to possibly long-lived

degradation products. Estimated BCFs and

HLCs for perfluorinated chemicals are listed

in Tables 3–13. Information Profiles for nonHPV perfluorinated chemicals for which

there were publicly available toxicity data are

posted on the ITC’s web site (http://

www.epa.gov/opptintr/itc). The ITC is

continuing to evaluate information on uses,

exposures, environmental fate, ecological

effects, and health effects of perfluorinated

chemicals.

TABLE 3.—PERFLUOROALKYL ACIDS AND SALTS1

CAS No. Chemical name BCF HLC

000335–77–3 1-Decanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heneicosafluoro- 10 3.03E-01

001763–23–1 1-Octanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-* 56 1.10E-02

002795–39–3 1-Octanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-, potassium salt* 56 1.10E-02

003825–26–1 Ammonium perfluorooctanoate* 56 9.10E-02

003871–99–6 1-Hexanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-, potassium salt* 3 3.97E-04

021615–47–4 Hexanoic acid, undecafluoro-, ammonium salt* 3 3.29E-03

029457–72–5 1-Octanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-, lithium salt 56 1.10E-02

* TSCA 8(e) submission

1 It should be noted that methods used to estimate BCF and HLC were based on associated chemical structures. The salts of carboxylic and

sulfonic acids are expected to exist as dissociated structures in the environment; the dissociated structure will be more water-soluble and likely to

have a lower BCF and HLC than the associated structure.

Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices 75557

TABLE 4.—PERFLUOROALKYL SULFONAMIDES

CAS No. Chemical name BCF HLC

000754–91–6 1-Octanesulfonamide, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro- 10000 1.84E-03

001691–99–2 1-Octanesulfonamide, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-N-(2-hydroxyethyl)-N-ethyl- 5543 5.72E-07

004151–50–2 1-Octanesulfonamide, ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-* 500 5.37E+00

024448–09–7 1-Octanesulfonamide, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-N-(2-hydroxyethyl)-N-methyl-*26000 4.30E-04

034449–89–3 1-Butanesulfanamide, ethyl-1,1,2,2,3,3,4,4,4-nonafluoro-N-(2-hydroxyethyl)- 206 7.50E-07

034454–97–2 1-Butanesulfonamide, 1,1,2,2,3,3,4,4,4-nonafluoro-N-(2-hydroxyethyl)-N-methyl- 86 5.65E-07

034455–03–3 1-Hexanesulfonamide, ethyl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-N-(2-hydroxyethyl)- 6331 2.07E-05

067584–55–8 2-Propanoic acid, 2-[methyl[(nonalfuorobutyl)sulfonyl]amino]ethyl ester 961 1.94E-05

067584–56–9 2-Propenoic acid, 2-methyl (undecafluoropentyl)sulfonyl amino ethyl ester 5330 1.02E-04

068555–72–6 1-Pentanesulfonamide, ethyl-1,1,2,2,3,3,4,4,5,5,5-undecafluoro-N-(2-hydroxyethyl)- 1142 3.94E-06

068555–74–8 1,1,2,2,3,3,4,4,5,5,5-Undecafluoro-N-(2-hydroxyethyl)-N-methylpentane-1-sulphonamide 478 2.97E-06

068555–75–9 1-Hexanesulfonamide, 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-N-(2-hydroxyethyl)-N-methyl- 2651 1.56E-05

068555–77–1 1-Butanesulfonamide, 3-(dimethylamino)propyl-1,1,2,2,3,3,4,4,4-nonafluoro- 465 4.63E-06

* TSCA 8(e) submission.

TABLE 5.—PERFLUORINATED QUATERNARY AMMONIUM CHEMICALS

CAS No. Chemical name BCF HLC

001652–63–7 1-Propanaminium,3-(((heptadecafluorooctyl)sulfonyl)amino)-N,N,N-trimethyl-, iodide 6 4.04E-10

038006–74–5 1-Propanaminium,3-[[(heptadecafluorooctyl)sulfonyl]amino]-N,N,N-trimethyl-, chloride 6 4.04E-10

TABLE 6.—PERFLUOROALKANES

CAS No. Chemical name BCF HLC

000076–19–7 Octafluoropropane 50 3.30E+01

000678–26–2 Dodecafluoropentane 488 3.50E+03

002994–71–0 Hexafluoro-1,2-bis(trifluoromethyl)cyclobutane 145 2.05E+03

TABLE 7.—FLUOROALKYL ETHERS

CAS No. Chemical name BCF HLC

000755–73–7 2,2,3,3-Tetrafluoro-3-methoxy-propionic acid methyl ester* 3 4.30E-05

001623–05–8 Propane, 1,1,1,2,2,3,3-heptafluoro-3-[(trifluoroethyenyl)oxy]- 76 8.74E+00

003330–14–1 Propane, 1-(1-(difluoro(1,2,2,2-tetrafluoroethoxy)methyl)-1,2,2,2-tetrafluoroethoxy)-1,1,2,2,3,3,3-

heptafluoro7355 4.99E+00

003330–15–2 Heptafluoropropyl 1,2,2,2-tetrafluoroethyl ether 151 3.90E+00

063863–43–4 Propanoic acid, 3-1-difluoro(trifluoroethenyl)oxy methyl-1,2,2,2-tetrafluoroethoxy-2,2,3,3-tetrafluoro-,

methyl ester

327 2.55E-03

104147–32–2 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline 160 1.29E-06

* TSCA 8(e) submission.

TABLE 8.—FLUOROALKYL IODIDES

CAS No. Chemical name BCF HLC

000423–39–2 1-Iodoperfluorobutane 1193 4.99E+01

002043–55–2 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane 6809 1.11E+01

068188–12–5 Perfluoroalkyl(C2–C18)ethyl iodide 1228 2.11E+00

TABLE 9.—GAMMA, OMEGA-PERFLUOROALKYL ALCOHOLS

CAS No. Chemical name BCF HLC

000647–42–7 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octanol 4064 1.50E-01

002043–47–2 3,3,4,4,5,5,6,6,6-Nonafluoro1-hexanol 132 5.42E-03

068391–08–2 2-Perfluoroalkyl (C6–C12) ethanol 3092 9.99E-02

TABLE 10.—PERFLUOROALKYL SULFONYL FLUORIDES

CAS No. Chemical name BCF HLC

000375–72–4 Nonafluorobutanesulfonyl fluoride 5364 8.91E-02

75558 Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices

TABLE 10.—PERFLUOROALKYL SULFONYL FLUORIDES—Continued

CAS No. Chemical name BCF HLC

000421–20–5 Methyl fluorosulfonate* 2 5.00E-05

068156–06–9 Cyclohexanesulfonyl fluoride, decafluoro(pentafluoroethyl)- 7741 7.57E+00

068318–34–3 Cyclohexanesulfonyl fluoride, decafluoro(trifluoromethyl)- 1396 1.44E+00

* TSCA 8(e) submission.

TABLE 11.—PERFLUOROGLYCOL ACID FLUORIDES

CAS No. Chemical name BCF HLC

004089–58–1 Propanoyl fluoride, 2,3,3,3-tetrafluoro-2-(1,1,2,3,3,3-hexafluoro-2-(1,1,2,2-tetrafluoro-2-

(fluorosulfonyl)ethoxy)propoxy)-

4709 7.55E-05

001422–71–5 3-Pentanone, 1,1,2,2,4,4,5,5-octafluoro-1,5-dimethoxy-* 3 4.27E-05

069116–71–8 Methyl 2,2-difluromalonyl fluoride* 3 1.50E-05

069116–72–9 Propanoic acid, 2,2,3,3-tetrafluoro-3-1,2,2,2-tetrafluoro-1-(fluorocarbonyl)ethoxy-, methyl ester* 2 1.30E-04

069116–73–0 Propanoic acid, 3-(2-(1,2-difluoro-2-oxo-1-(trifluoromethyl)ethoxy)-1,2,2-trifluoro-1-

(trifluoromethyl)ethoxy)-2,2,3,3-tetrafluoro-, methyl ester

121 1.70E-04

* TSCA 8(e) submission

1 It should be noted that methods used to estimate BCF and HLC were based on non-hydrolyzed chemical structures. Certain perfluoroglycol

acid fluorides are expected to rapidly hydrolyze (within an hour, depending upon chemical concentration) in the environment; the hydrolysis products will be more water-soluble and likely to have a lower BCF and HLC than the non-hydrolyzed structure.

TABLE 12.—PERFLUOROALKYL CARBOXYLIC ACID FLUORIDES

CAS No. Chemical name BC F HLC

000335–66–0 Pentadecylfluorooctanoyl fluoride 3011 2.58E+02

000375–84–8 Tridecafluoroheptanoyl fluoride 543 4.91E+01

TABLE 13.—PERFLUORINATED CHEMICALS NOT ASSIGNED TO A STRUCTURAL CLASS

CAS No. Chemical name BCF HLC

019430–93–4 1-Hexene, 3,3,4,4,5,5,6,6,6-nonafluoro- 1393 1.11E+02

068140–20–5 Perfluoroalkyl (C4–C10) ethyl mercaptan 1606 5.26E+00

2. Information needs. The ITC needs

measured BCFs, HLCs, and bioaccumulation

data for most of the perfluorinated chemicals.

Information on uses, exposures, health

effects, and ecological effects is needed for

perfluoroalkyl acids and salts, perfluoroalkyl

sulfonamides, perfluorinated quaternary

ammonium chemicals, perfluoroalkanes,

fluoroalkyl ethers, fluoroalkyl iodides,

gamma, omega-perfluoroalkyl alcohols,

perfluoroalkyl sulfonyl fluorides,

perfluoroglycol acid fluorides, perfluoroalkyl

carboxylic acid fluorides, 1-hexene,

3,3,4,4,5,5,6,6,6-nonafluoro- (CAS No.

19430–93–4), and perfluoroalkyl (C4–C10)

ethyl mercaptan (CAS No. 68140–20–5). For

the perfluoroalkyl iodides, the ITC needs

information on possible long-lived

atmospheric degradation products. ITC is not

soliciting information on two perfluoroalkyl

sulfonamides that are in the EPA’s HPV

Challenge Program, 1-octanesulfonamide,

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-

heptadecafluoro-N-(2-hydroxyethyl)-N-ethyl-

(CAS No. 1691–99–2) and 1-

octanesulfonamide,

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-

heptadecafluoro-N-(2-hydroxyethyl)-Nmethyl- (CAS No. 24448–09–7) and the

pesticides, lithium perfluorooctane sulfonate

(LPOS) or 1-octanesulfonic acid,

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-

heptadecafluoro-, lithium salt (CAS No.

29457–72–5) (see http://www.epa.gov/

opprd001/factsheets/factsht2.htm) and

Sulfuramid or 1-octanesulfonamide, -ethyl1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-

heptadecafluoro- (CAS No. 4151–50–2) (see

http://www.epa.gov/opp).

IV. Revisions to the TSCA Section 4(e)

Priority Testing List

A. Chemicals Added to the Priority Testing

List: Nonylphenol Polyethoxylate

Degradation Products

1. Recommendation. Add 8 nonylphenol

polyethoxylate degradation products to the

Priority Testing List to obtain information to

meet U.S. Government data needs.

2. Rationale for recommendation.

Alkylphenols, polyalkylphenols, alkylphenol

ethoxylates, and alkylphenol polyethoxylates

were recommended in the ITC’s 37th (61 FR

4188, February 2, 1996) (FRL–4991–6), 39th

(62 FR 8578, February 25, 1997) (FRL–5580–

9), and 41st Reports. Nonylphenol

polyethoxylates were recommended in the

ITC’s 39th Report. Recent studies have

measured nonylphenol polyethoxylate

degradation products in wastewater effluents

and surrounding aquatic systems (Bennett

and Metcalfe, 2000; Hale et al., 2000). Some

of these products can cause neuroendocrinemediated effects in fish at low parts per

billion (ppb) concentrations. One

nonlylphenol polyethoxylate degradation

product, branched 4-nonylphenol (mixed

isomers) (CAS No. 84852–15–3) was

previously recommended in the ITC’s 37th

Report. As a result of these findings and to

meet U.S. Government data needs for these

chemicals, the ITC is adding 8 nonlylphenol

polyethoxylate degradation products to the

Priority Testing List (Table 14).

TABLE 14.—NONYLPHENOL POLYETHOXYLATE DEGRADATION PRODUCTS BEING ADDED TO THE PRIORITY TESTING LIST

CAS No. Nonylphenol polyethoxylate degradation product

104–35–8 4-nonylphenol ethoxylate (NP1EO)

20427–84–3 4-nonylphenol diethoxylate (NP2EO)

Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices 75559

TABLE 14.—NONYLPHENOL POLYETHOXYLATE DEGRADATION PRODUCTS BEING ADDED TO THE PRIORITY TESTING LIST—

Continued

CAS No. Nonylphenol polyethoxylate degradation product

4-nonylphenol triethoxylate (NP3EO)

4-nonylphenol tetraethoxylate (NP4EO)

3115–49–9 4-nonylphenoxy acetic acid (NP1EC)

106807–78–7 4-nonylphenoxy ethoxy acetic acid (NP2EC)

108241–00–5 4-nonylphenoxy diethoxy acetic acid (NP3EC)

4-nonylphenoxy triethoxy acetic acid (NP4EC)

3. Supporting information. Recent studies

have documented that nonylphenol

polyethoxylate degradation products can act

as in vitro and in vivo estrogen agonists in

fish and amphibians (Jobling and Sumpter,

1993; Jobling et al., 1996; Kloas et al., 1999).

While most of these studies were conducted

with nonylphenol and octylphenol, there is

evidence to suggest that nonylphenol

polyethoxylate degradation products (shortchain ethoxylates and carboxylates) can also

act to disrupt neuroendocrine function.

i. Effects. Exposure of male fathead

minnows to nonylphenol at 1.1 ppb caused

an increase in the number and size of sertoli

cells and germ cell syncytia (MilesRichardson et al., 1999). In the same study,

exposure of fathead minnows to 5.5 ppb

nonylphenol polyethoxylate consisting of

primarily 7–11 carbon ethoxylate chains, no

changes in number and size of sertoli cells

and germ cell syncytia were detected, but

shorter carbon ethoxylate chains (1–4

carbons) were not tested. In the same

laboratory, exposure of fathead minnows to

0.05 ppb nonylphenol caused significant

increases in plasma vitellogenin and

estradiol (Giesy et al., 2000).

Exposure of male rainbow trout to 30 ppb

octylphenol, nonylphenol, 4-nonylphenoxy

acetic acid (NP1EC), and 4-nonylphenol

diethoxylate (NP2EO) caused increases in

serum vitellogenin and inhibition in

testicular growth (Jobling et al., 1996).

Octylphenol was the most potent followed by

nonylphenol, NP2EO, and NP1EC. A lowestobserved-effect-concentration (LOEC) was

not determined for NP2EO or NP1EC, but the

30 ppb exposure concentrations for NP1EC

and NP2EO are well below total

concentrations of carboxylates and

ethoxylates reported for many of the effluents

in the midwestern United States that are

discussed below. Exposure of female rainbow

trout to 1 ppb nonylphenol and NP2EO and

10 ppb NP1EC reduced growth (Ashfield et

al., 1998).

ii. Environmental concentrations. Despite

data suggesting that

nonylphenolpolyethoxylate metabolites may

biodegrade (Staples et al., 1999), recent

studies demonstrated that nonylphenol

polyethoxylate effluent and effluent

dominated stream concentrations may exceed

LOEC concentrations reported in the

literature. Barber et al. (1999) estimated

nonylphenol polyethoxylate degradation

products in seven midwest sewage treatment

plant effluents and in one effluent-dominated

stream (Des Plaines River, IL) approximately

100 killometers (km) downstream of the

major nonylphenol polyethoxylate sources.

Generally effluents had nonylphenol

polyethoxylate degradation product

concentrations greater than 50 ppb with

NPE2C the predominant form in most

effluents and in the effluent dominated

stream. Nonylphenol concentrations in the

Des Plaines River slightly exceeded 1 ppb.

Naylor et al. (1996) and Field and Reed

(1996) estimated nonylphenol, total

nonylphenol ethoxylate, and NP1EC-NP4EC

(4-nonylphenoxy triethoxy acetic acid)

concentrations in 15 pulp and paper mill and

6 sewage treatment plant effluents to the Fox

River, WI. Total nonylphenol ethoxylate

typically exceeded 50 ppb in all effluents,

while nonylphenol concentrations were

generally greater than 1 ppb. The

nonylphenol carboxylates concentrations

were always greater than 15 and 140 ppb in

the pulp and paper mill and sewage

treatment effluents, respectively.

Nonylphenol and total nonylphenol

ethoxylate Fox River concentrations near

Green Bay were 0.582 and 2.78 ppb,

respectively, while the total nonylphenol

carboxylate concentration was 13.5 ppb.

Nonylphenol carboxylates were shown to

persist for considerable distances

downstream. In addition to these existing

data, EPA is sponsoring ongoing programs to

sample sediment and fish in the midwestern

United States.

4. Information needs. Data are needed to

determine the LOECs (in comparison to

estradiol) of branched 4-nonylphenol (mixed

isomers), 4-nonylphenol ethoxylate (NP1EO),

4-nonylphenol diethoxylate (NP2EO), 4-

nonylphenol triethoxylate (NP3EO), 4-

nonylphenol tetraethoxylate (NP4EO), 4-

nonylphenoxy acetic acid (NP1EC), 4-

nonylphenoxy diethoxy acetic acid (NP2EC),

4-nonylphenoxy triethoxy acetic acid

(NP3EC), and 4-nonylphenoxy tetraethoxy

acetic acid (NP4EC) causing neuroendocrine

effects in aquatic organisms. Data are also

needed to determine whether nonylphenol

polyethoxylate degradation products have

the potential to interfere with growth and

metamorphosis of amphibians (e.g.,

tadpoles).

B. Chemicals Removed From the Priority

Testing List: Alkylphenols and Alkylphenol

Ethoxylates

1. Background. In this Report, the ITC is

removing 4 alkylphenols (APs) and 15

alkylphenol ethoxylates (APEs) from the

Priority Testing List. The 4 APs were added

to the Priority Testing List in the ITC’s 37th

Report; the 15 APEs were added to the

Priority Testing List in the ITC’s 39th Report.

Submission of TSCA section 8(d) studies for

APs added to the Priority Testing List in the

ITC’s 37th Report were required by a TSCA

section 8(d) HaSD rule (61 FR 7421, February

28, 1996) (FRL–4991–6). TSCA section 8(d)

and FYI studies for APEs added to the

Priority Testing List in the ITC’s 39th Report

were voluntarily submitted in response to

information solicitations discussed in the

ITC’s 39th Report.

2. Removal rationale. The APs and APEs

being removed from the Priority Testing List

are listed in Table 15. Three APs and 13

APEs are being removed because no domestic

production or importation volumes were

reported to the USEPA in response to any of

the 1986, 1990, 1994, and 1998 Information

Update Rules (IURs) or the 2000 PAIR rule.

Production/importation volumes were

reported for one AP and two APEs in the

1990 IUR but not in the subsequent 1994 and

1998 IURs or the 2000 PAIR rule. These three

chemicals are also being removed because of

insufficient production.

TABLE 15.—APS AND APES BEING REMOVED FROM THE PRIORITY TESTING LIST

CAS No. Chemical name Category Removal rationale

104–43–8 4-Dodecylphenol AP b

3884–95–5 2-(1,1,3,3-Tetramethylbutyl)phenol AP a, b

31195–95–6 Isobutylphenol (mixed isomers) AP a, b

54932–78–4 4-(2,2,3,3-Tetramethylbutyl)phenol AP a, b

7311–27–5 2-[2-[2-[2-(4-Nonylphenoxy)ethoxy]ethoxy]ethoxy]ethanol APE a, b

20636–48–0 14-(4-Nonylphenoxyl)-3,6,9,12-tetraoxatetradecan-1-ol APE a, b

26264–02–8 14-(Nonylphenoxyl)-3,6,9,12-tetraoxatetradecan-1-ol APE a, b

75560 Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices

TABLE 15.—APS AND APES BEING REMOVED FROM THE PRIORITY TESTING LIST—Continued

CAS No. Chemical name Category Removal rationale

26571–11–9 26-(4-Nonylphenoxyl)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol APE b

27176–93–8 2-[2-(4-Nonylphenoxyl)ethoxyl]ethanol APE a, b

27177–01–1 17-(Nonylphenoxyl)-3,6,9,12,15-pentaoxaheptadecan-1-ol APE a, b

27177–05–5 23-(Nonylphenoxy)-3,6,9,12,15,18,21-heptaoxatricosan-1-ol APE a, b

27177–08–8 29-(Nonylphenoxy)-3,6,9,12,15,18,21,24,27-nonaoxanonacosan-1-ol APE b

51938–25–1 Poly(oxy-1,2-ethanediyl), .alpha.-(2-nonylphenyl)-.omega.-hydroxy- APE a, b

65455–72–3 29-(Isononylphenoxy)-3,6,9,12,15,18,21,24,27-nonaoxanonacosan-1-ol APE a, b

152143–22–

1

Poly(oxy-1,2-ethanediyl), .alpha.-(4-nonylphenyl)-.omega.-hydroxy-, branched, phosphates APE a, b

Nonoxynol-2 APE a, b

Nonoxynol-3 APE a, b

Nonoxynol-7 APE a, b

.alpha.-(4-Nonylphenol)-.omega.-hydroxypoly(oxyethylene) APE a, b

a No domestic production or importation volumes were reported to the USEPA in response to 1986, 1990, 1994, and 1998 IURs (indicating

that volumes were less than 10,000 pounds per site in 1985, 1989, 1993, and 1997).

b No domestic production or importation volumes were reported to the USEPA in response to the January 11, 2000, PAIR rule published in the

FEDERAL REGISTER (65 FR 1548) (FRL–5777–2) (indicating that volumes were less than 1,000 pounds per site in 1999).

V. References

1. Ashfield, L.A., Pottinger, T.G., and

Sumpter, J.P. 1998. Exposure of female

juvenile rainbow trout to alkylphenolic

compounds results in modification to growth

and ovosomatic index. Environmental

Toxicology and Chemistry 17:679–686.

2. Agency for Toxic Substances and

Disease Registry (ATSDR). 1996.

Toxicological Profile for Hexachlorobenzene.

ATSDR. Atlanta, Georgia.

3. Barber, L.B., Brown, G.K., and Zaugg,

S.D. 1999. Potential endocrine disrupting

chemicals in treated municipal wastewater

and river water, Upper Midwest, USA. In:

Keith, L., Jones-Lepp, T., and Needham, L.

(Eds) Analysis of Environmental Endocrine

Disruptors, American Chemical Society

Symposium Series No. 747. American

Chemical Society. Washington, DC.

4. Bennet, E.R. and Metcalfe, C.D. 2000.

Distribution of degradation products of

alkylphenol ethoxylates near sewage

treatment plants in the Lower Great Lakes,

North America. Environmental Toxicology

and Chemistry 19:784–792.

5. Chhabra, R.S., Maronpot, R.M., Bucher,

J.R., Haseman, J.K., Toft, J.D., and

Hejtmancik, M.R. 1999. Toxicology and

carcinogenesis studies of pentachlorophenol

in rats. Toxicological Science 48:14–20.

6. Field, J. F. and Reed, R. L. 1996.

Nonylphenol polyethoxy carboxylate

metabolites of nonionic surfactants in paper

mill effluents, municipal sewage treatment

plant effluents and river waters.

Environmental Science and Technology

30:3544–3550.

7. Giesy, J.P., Pierens S.L., MilesRichardson S., Kramer, V.J., Snyder, S.S.,

Nichols, K.M., Snyder, E., Villenueve, D.A.,

and Giesy, J.P. 2000. Effects of 4-

Nonylphenol on Fecundity and Biomarkers

of Estrogenicity in Fathead Minnows

(Pimephales promelas). Environmental

Toxicology and Chemistry 19:1368–1377.

8. Hahn, M.E, Gasiewicz, T.A, Linko, P.,

and Goldstein, J.A. 1988. The role of the Ah

locus in hexachlorobenzene-induced

porphyria: Studies in congenic C57BL/6J

mice. Biochemical Journal 254:245–254.

9. Hahn, M.E, Goldstein, J.A, Linko, P., and

Gasiewicz, T.A. 1989. Interaction of

hexachlorobenzene with the receptor for

2,3,7,8-tetrachlorodibenzo-p-dioxin in vitro

and in vivo. Archives of Biochemistry and

Biophysics 270:344–355.

10. Hale, R.C., Smith, C.L., De Fur, P.O.,

Harvey, E., Bush, E.O., La Guardia, M.J., and

Vadas, G.G. 2000. Nonylphenols in

sediments and effluents associated with

diverse wastewater outfalls. Environmental

Toxicology and Chemistry 19:946–952.

11. Jobling, S. and Sumpter, J. P. 1993.

Detergent compounds in sewage treatment

plant effluents are weakly oestrogenic to fish:

an in vitro study using rainbow trout

hepatocytes. Aquatic Toxicology 27:361–372.

12. Jobling, S., Sheahan, D., Osborne, J.A.,

Matthiessen, P., and Sumpter, J.P. 1996.

Inhibition of testicular growth in rainbow

trout (Oncorhynchus mykiss) exposed to

estrogenic alkylphenolic compounds.

Environmental Toxicology and Chemistry

15:194–202.

13. Kloas, W., Lutz, I., and Einspanier, R.

1999. Amphibians as a model to study

endocrine disruptors: II. Estrogenic activity

of environmental chemicals in vitro and in

vivo. Science of the Total Environment

225:59–68.

14. Lai, D.Y., Woo, Y.T., Argus, M.F., and

Arcos, J.C.1996. Cancer risk reduction

through mechanism-based molecular design

of chemicals. pp. 62–73. In: S.C. DeVito and

R.L. Garrett, (Eds) Designing Safer Chemicals,

ACS Symposium Series No. 640, American

Chemical Society, Washington, DC.

15. Linko, P., Yeowell, H.N., Gasiewicz,

T.A., and Goldstein, J.A.1986. Induction of

cytochrome P-450 isozymes by

hexachlorobenzene in rats and aromatic

hydrocarbon (Ah)-responsive mice. Journal

of Biochemical Toxicology 1:95–107.

16. Mehendale, H.M., Fields, M., and

Matthews, H.B. 1975. Metabolism and effects

of hexachlorobenzene on hepatic microsomal

enzymes in the rat. Journal of Agriculture

and Food Chemistry 23:261–265.

17. Miles-Richardson, S.R., Pierens, S.L.,

Nichols, K.M., Kramer, V.J., Snyder, E.M.,

Snyder, S.A., Render, J.A., Fitzgerald, S.D.,

and Giesy, J.P. 1999. Effects of waterborne

exposure to 4-nonylphenol and nonylphenol

ethoxylate on secondary sex characteristics

and gonads of fathead minnows (Pimephales

promelas). Environmental Research

A80:S122–S137.

18. Naylor, C.G., Williams, J. B., Varineau,

P. T., Webb, D. A., and Sanders, D. F. 1996.

Nonylphenol ethoxylates in an industrial

river. 4th CEISO World Surfactants Congress,

Volume 4.

19. PPG Industries. 1982. MRID No.

00117566. Available from EPA. Write to FOI,

EPA, Washington, DC 20460.

20. PPG Industries. 1983. MRID No.

00132885. Available from EPA. Write to FOI,

EPA, Washington, DC 20460.

21. PPG Industries. 1985a. MRID No.

00150343, 00150366. Available from EPA.

Write to FOI, EPA, Washington, DC 20460.

22. PPG Industries. 1985b. MRID No.

00132883, 00150329. Available from EPA.

Write to FOI, EPA, Washington, DC 20460.

23. Rozman, K., Mueller W., Coulston, F.,

and Korte, F. 1977. Long-term feeding study

of hexachlorobenzene in rhesus monkeys.

Chemosphere 6:81–84.

24. Russom, C.L., Bradbury, S.P., Braiders,

S.J., Hammermeister, D.E., and Drummond,

R.A. 1997. Predicting modes of toxic action

from chemical structure: Acute toxicity in the

fathead minnow (Pimephales Promelas).

Environmental Toxicology and Chemistry

16:948–967.

25. Staples, C.A., Williams, J.B., Blessing,

R.L., and Varineau, P.T. 1999. Measuring the

biodegradability of nonylphenol ether

carboxylates, octylphenol ether carboxylates

and nonylphenol. Chemosphere 38:2029–

2039.

26. Woo, Y.T., Lai, D.Y., Argus, M.F., and

Arcos, J.C. 1995. Development of structureactivity relationship rules for predicting

carcinogenic potential of chemicals.

Toxicology Letters 79:219–228.

27. Woo, Y.T., Lai, D.Y., Argus, M.F., and

Arcos, J.C. 1998. An integrative approach of

combining mechanistically complementary

short-term predictive tests as a basis for

assessing the carcinogenic potential of

chemicals. Journal of Environmental Science

and Health C16:101–122.

VI. TSCA Interagency Testing Committee

Statutory Organizations and Their

Representatives

Council on Environmental Quality

Federal Register / Vol. 65, No. 232 / Friday December 1, 2000 / Notices 75561

Department of Commerce

National Institute of Standards and

Technology

Robert Huie, Member

Barbara C. Levin, Alternate

National Oceanographic and

Atmospheric Administration

Nancy Foster, Member

Teri Rowles, Alternate

Environmental Protection Agency

Paul Campanella, Member

David R. Williams, Alternate

National Cancer Institute

Victor Fung, Alternate

National Institute of Environmental Health

Sciences

Scott Masten, Member

William Eastin, Alternate

National Institute for Occupational Safety

and Health

Albert E. Munson, Member

Mark Toraason, Alternate

National Science Foundation

A. Frederick Thompson, Member

Marge Cavanaugh, Alternate

Occupational Safety and Health

Administration

Val H. Schaeffer, Member, Chair

Lyn Penniman, Alternate

Liaison Organizations and Their

Representatives

Agency for Toxic Substances and Disease

Registry

William Cibulas, Member

Consumer Product Safety Commission

Jacqueline Ferrante, Member

Treye Thomas, Alternate

Department of Agriculture

Clifford P. Rice, Member

Department of Defense

Barbara Larcom, Member

Kenneth Still, Alternate

Jose Centeno, Alternate

Department of the Interior

Barnett A. Rattner, Member, Vice Chair

Food and Drug Administration

Ronald Lorentzen, Member

Raju Kammula, Alternate

David Hatten, Alternate

National Library of Medicine

Vera W. Hudson, Member

National Toxicology Program

NIEHS, FDA, and NIOSH Members

Counsel

Scott Sherlock, Office of Pollution

Prevention and Toxics, EPA

Technical Support Contractor

Syracuse Research Corporation

ITC Staff

John D. Walker, Executive Director

Norma S. L. Williams, Executive

Assistant

TSCA Interagency Testing Committee,

Office of Pollution Prevention and Toxics

(7401), Environmental Protection Agency,

1200 Pennsylvania Ave., NW., Washington,

DC 20460; telephone number: (202) 260–

1825; fax number: (202) 260–7895; e-mail

address: williams.norma@epa.gov; url: http:/

/www.epa.gov/opptintr/itc.

[FR Doc. 00–30546 Filed 11–30–00; 8:45 am]

BILLING CODE 6560–50–S