UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

 OFFICE OF

                                                                        
                                    PREVENTION, PESTICIDES AND 

         TOXIC SUBSTANCES

June 27, 2007

MEMORANDUM

SUBJECT:	Product Chemistry Chapter for the Bromonitrostyrene
Reregistration Eligibility Decision (RED) Document

	DP Barcode:  336266		Reregistration Case No.:  2065

FROM:	Srinivas Gowda, Microbiologist/Chemist

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

TO:			Mark Hartman, Branch Chief

Diane Isbell, Team Leader

ShaRon Carlisle, Chemical Review Manager

Regulatory Management Branch II

Antimicrobials Division (7510P)

Jenny Tao, Risk Assessor

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

THRU:	Siroos Mostaghimi, Team Leader, Team one

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

Norman Cook, Branch Chief

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

Chemical Name	  PC Code	CAS#		Common Names

		      beta-Bromo-beta-	  101401	7166-19-0	Bromonitrostyrene

		         nitrostyrene

Attached is the Product Chemistry Chapter for the Bromonitrostyrene RED
Document.

Attachment:  Product Chemistry Chapter for the Bromonitrostyrene RED
Document.

BROMONITROSTYRENE

REREGISTRATION ELIGIBILITY DECISION

PRODUCT CHEMISTY CHAPTER

PC Code:  101401; Case No. 2065

REGULATORY HISTORY

The first product containing bromonitrostyrene was registered with EPA
on October 12, 1972.  Presently, there are 3 active products, no inert
products, and 11 cancelled products under a single PC Code 101401, which
are listed in Table 1 under Appendix.  Bromonitrostyrene is Fungicide,
Slimicide, Molluscide, Mildewcide, Algaecide, and
Microbicide/Microbiostat.

Bromonitrostyrene is used in the manufacture of a variety of materials
as a preservative such as cleaners, adhesives, paper and paperboard
(food contact), water based coatings, paints, inks and dyes.  Industrial
process and water system uses include evaporative condenser water and
systems, pulp and paper mill water systems, brewery pasteurizer water
and metal working machinery coolant systems.  Bromonitrostyrene
containing products are also approved for use in aquatic areas such as
ponds, waste water systems, sewage water and cooling tower water.

CHEMICAL IDENTIFICATION

 

				Figure 1.  Molecular Structure of Bromonitrostyrene

Common Name:		Bromonitrostyrene

Chemical Name:		beta-Bromo-beta-nitrostyrene

				2-Bromo-2-nitroethenylbenzene				

Other Name(s):		Giv-Gard, Canguard, Bioban BNS

					

CAS Registry Number:	7166-19-0

OPP Chemical Code:	101401

Case Number:		2065

Empirical Formula:		C8H6BrNO2

Molecular Weight:		228.04

Manufacturer:		The Dow Chemical Company

					

Highest Percent of 

Active Ingredient:		25%

Formulation Types

Registered:			Technical Grade Active Ingredients (TGAI):

	None.

Manufacturing Use Products (MP):

	Soluble Concentrate

End Use Products (EP):

	Soluble Concentrate

Chemical Properties:	Bromonitrostyrene (TGAI) is a yellow powder with a
weak musty odor and melting point of 65-66°C (58°C minimum). 
Bromonitrostyrene (TGAI) is solid and, therefore, has no boiling point. 
Bromonitrostyrene (TGAI) has an estimated log Kow of 2.34 and a vapor
pressure of 4.14 x 10ˉ4 mm Hg at 25˚C ± 0.5˚C.  Bromonitrostyrene
(TGAI) is soluble in water at 0.001g/100 ml (10 ppm) at 25˚C. 
Bromonitrostyrene (TGAI) is readily soluble in many organic solvents and
has a density of 2.2753 g/ml at 20˚C. It has a pH of 4 at 25˚C and
stable under normal storage conditions.

25% Bromonitrostyrene is an amber colored liquid with a mild aromatic
odor.  It has a density of 8.2 lb/gal and specific gravity of 0.98.  It
has a viscosity of 1.52 cps at 25˚C.

PRODUCT CHEMISTRY DATA REQUIREMENTS FOR REREGISTRATION OF
BROMONITROSTYRENE:

Product chemistry data requirements and results are summarized in Tables
2 and 3 under, “APPENDIX”.

FINDINGS/CONCLUSIONS:

All product chemistry data requirements have been fulfilled for the
active ingredient Bromonitrostyrene.  See Tables 2 and 3 under,
“APPENDIX”.  RASSB has no objections to the reregistration of
Bromonitrostyrene with respect to product chemistry data requirements.

APPENDIX:

              Table 1.  Registered Active Products of Bromonitrostyrene

EPA Reg. No.

	

Formulation Type

	

Percent Active Ingredient

	

Registrant





464-683 

	

MP	

25%	

The Dow Chemical Company



464-684 

	

MP	

25%	

The Dow Chemical Company



464-686 

	

EP	

25% 	

The Dow Chemical Company



Table 2: Manufacturing and Impurity Data for Bromonitrostyrene

Product Identity, Composition, and Analysis

Old Guideline No.	New Guideline No.	Requirement	Use Pattern2	MRID
Status1	Details or Deficiency

61-1	830.1550	Product identity and composition	3,7,8	93372

41611401	A	Refer to Chemical Identification on page 2

61-2a	830.1600	Description of materials used to produce the product
3,7,8	41611401	A	BNS 25%: CBI

61-2a	830.1620	Description of production process	3,7,8	41611401	A	BNS
25%: CBI

61-2a	830.1650	Description of formulation process	3,7,8	41611401	A	BNS
25%: CBI

61-2b	830.1670	Discussion of formation of impurities	3,7,8	41611402	A
BNS 25%: CBI

62-1	830.1700	Preliminary analysis	3,7,8	42399703

42499401	A	BNS 25%: CBI



62-2	830.1750	Certified limits	3,7,8	41611403

42399703

42940601	A	BNS 25%: CBI

62-3	830.1800	Enforcement analytical method	3,7,8	41611402

41611403

42399703

42499401	A	BNS 25%: Gas Chromatography/Mass Spectrometry 

64-1	830.1900	Submittal of samples	3,7,8

N/A	



1A = Acceptable; N/A = Not Applicable.

2Use Pattern:

(3) Commercial, institutional and industrial premises and equipment

(7) Materials preservatives

(8) Industrial processes and water systems

Table 3: Physical and Chemical Properties for Bromonitrostyrene

Old Guideline No.	New Guideline No.	Requirement	Use Pattern2	MRID
Status1	Results or Deficiency

63-2	830.6302	Color	3,7,8	93372

108467

41603502

92011020	A	BNS 25%: Amber

TGAI:  Yellow Powder

63-3	830.6303	Physical state	3,7,8	93372

108467

92011020	A	BNS 25%: Clear Liquid 

TGAI: Yellow Powder

63-4	830.6304	Odor	3,7,8	93372

108467

92011020	A	BNS 25%: Mild Aromatic

TGAI: Weak Musty

63-5	830.7200	Melting Point	3,7,8	108467

˚C

(58˚C Min.)

63-6	830.7220	Boiling Point	3,7,8

N/A

	63-7	830.7300	Density, Bulk Density, or Specific Gravity	3,7,8	93372

108467

44524501

41603502

92011020	A	BNS 25%: Density: 8.2 lb/gal

                     1.153 g/ml at 25˚C

BNS 25%: Sp gr.: 0.98

TGAI: Density: 2.2753 g/ml at 20˚C

63-8	830.7840	Water solubility 	3,7,8	108467

41603502

92011020	A

	TGAI: 0.001 g/100 ml at 25˚C

63-8	830-xxxx	Solubility in organic solvents at 25˚C (g/100 ml) 	3,7,8
108467

92011020

	A	TGAI:  g/100 ml

95% Ethanol  4 

Acetone  100

Benzene  100

Propylene glycol  3

Isopropyl myristate  14

Mineral oil  4

Dimethyl sulfoxide  90

Dimethyl formamide  125

Dioxane  150

63-9	830.7950	Vapor Pressure	3,7,8	42361405	A	TGAI: 4.14 x 10-4 mm Hg at
25˚C ± 0.5˚C

63-10	830.7370	Dissociation constants in water	3,7,8	92011999	A 	Does
not dissociate (Waived)

63-11	830.7550	Partition coefficient          (n-octanol / water)	3,7,8
92011999

40661011	A	Log Po/w = 2.34 (EPI Suite)

Log PBNS = 2.71 (Calculated value)

63-12	830.7000	pH	3,7,8	41603503

41603504	A

4 at 25˚C

BNS 25%: 3.58 at 25˚C

63-13	830.6313	Stability to normal and elevated temperatures. 

Stability to metals.

Stability to metal ions.	3,7,8	108467

41603502

92011020	A

	TGAI: Stable under normal storage conditions. It is stable in
non-alcoholic solvents in the dark or artificial light but decomposes in
these solvents or exposure to direct sunlight for prolonged periods of
time. BNS react with alcoholic solvents resulting in reduced activity. 
beta-Bromo-beta-nitrostyrene hydrolyzes in aqueous solutions with no
loss of antimicrobial properties.

Upon hydrolysis of beta-Bromo-beta-nitrostyrene traces of acid (i.e.,
HBr) are formed which cause corrosion of metal surfaces.

beta-bromo-beta-nitirostyrene decomposes at 170°C.

63-15	830.6315	Flammability	3,7,8	93372

44524501

BNS 25%: 102.0±1.3˚C

63-18	830.7100	Viscosity	3,7,8	406413-01	A	BNS 25%: 1.52 cP at 25˚C

63-20	830.6320	Corrosion Characteristic	3,7,8	40641302

44524501

BNS 25%: 

Steel : 127 mils per year.  very corrosive to steel

Aluminum: 4.4 to 4.7 mils per year.  Slightly corrosive to aluminum

1A = Acceptable; N/A = Not applicable.

2Use Pattern:

(3) Commercial, institutional and industrial premises and equipment

(7) Materials preservatives

(8) Industrial processes and water systems

BIBLIOGRAPHY

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༁䬃愀϶K瑹挞;؀Virgilio, J. (1990) Analysis and Certification of
Product Ingredients for Giv-Gard BNS 25% AF,... Containing the Active
Ingredient Beta-Bromo-Beta-Nitro-styrene: Lab Project Number: BNS-8/
90b. Unpublished study prepared by Givaudan Corp. 

42361405	Pesselman, R. (1992) Vapor Pressure Determinastion of GIV
2-0820: Final Report: Lab Project Number: 6412-100. Unpublished study
prepared by Hazleton Wisconsin, Inc. 

42399703	Sack, T. (1992) Chemical Analysis of Giv-Gard BNS 25% AF in
Support of FIFRA Registration: Series 62-1 Preliminary Analysis, Series
62-2 Certification of Limits Studies, and Series 62-3 Analytical
Methods: Lab Project Number: MRI 3006-F. Unpublished study prepared by
Midwest Research Institute. 

42499401	Clark, A. (1992) Preliminary Analysis for Giv-Gard BNS 25% AF:
Supplementary Report of Product Chemistry ?MRID# 42399703|: Lab Project
Number: 3006-F. Unpublished study prepared by Midwest Research
Institute.

42940601	Rives, D.; Lewis, B. (1993) Supplemental Data for MRID
#42399703 and 42499401: Certification of Ingredient Limits for Giv-Gard
BNS 25% AF, EPA Registration No. 824-10, Containing the Active
Ingredient beta-Bromo-beta-nitrostyrene: Lab Project Number: BNS-9/93.
Unpublished study prepared by Givaudan-Roure Corporation, Specialty
Division Quality Assurance Lab. 8 p. 

44524501	Bollmeier, A. (1998) Product Chemistry for Bioban BNS 25% BA.
Unpublished study prepared by Angus Chemical Co. 39 p. 

92011020	Lewis, B.; Manowitz, M. (1990) Givaudan Phase 3 Summary of MRID
00093372 and Related MRID No. 00108467. Physical and Chemical
Characteristics of beta-Bromo-beta- nitrosytrene (sic).

92011999	Givaudan (1990) Reregistration Phase 3 Response:
Bromo-b-nitrostyrene (Note: b = beta). Correspondence and Supporting
Material. 

None	Leo, Hansch and Elkins (1971) (An alternative to actual measurement
of the Kow, using the procedure of Leo, Hansch and Elkins. Chemical
Reviews, Vol. 71, No. 6, pp. 525-61 5, Dec. 1971)



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