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Terbutryn

PubChem CID
13450
Structure
Terbutryn_small.png
Terbutryn_3D_Structure.png
Molecular Formula
Synonyms
  • Terbutryn
  • 886-50-0
  • TERBUTRYNE
  • Clarosan
  • Shortstop
Molecular Weight
241.36 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Terbutryn is a methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by a tert-butylamino and an ethylamino group at positions 2 and 4 respectively. It has a role as a herbicide, a xenobiotic and an environmental contaminant. It is a methylthio-1,3,5-triazine and a diamino-1,3,5-triazine.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Terbutryn.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-N-tert-butyl-4-N-ethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H19N5S/c1-6-11-7-12-8(15-10(2,3)4)14-9(13-7)16-5/h6H2,1-5H3,(H2,11,12,13,14,15)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IROINLKCQGIITA-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCNC1=NC(=NC(=N1)SC)NC(C)(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H19N5S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

886-50-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-(tert-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine
  • 2-ethylamino-6-methylthio-4-tert-butylamino-1,3, 5-triazine
  • Clarosan
  • terbutrin
  • terbutryn
  • terbutryne

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
241.36 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
241.13611680 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
241.13611680 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
88 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
206
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

White solid; [HSDB]

3.2.2 Color / Form

WHITE, CRYSTALLINE
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 458
White powder
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D 403

3.2.3 Boiling Point

154-160 °C at 0.06 mm Hg
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-466

3.2.4 Melting Point

104 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-466

3.2.5 Solubility

35.9 [ug/mL] (The mean of the results at pH 7.4)
Readily soluble in organic solvents
Meister, R.T., Sine, C. (eds) Crop Protection Handbook Volume 92, Willoughby, OH, 2006., p. D 402
Solubilities in organic solvents at 20 °C
Solvent
Acetone
g/L
220
Solvent
Hexane
g/L
9
Solvent
n-Octanol
g/L
130
Solvent
Methanol
g/L
220
Solvent
Toluene
g/L
45
Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
READILY SOL IN ETHYLGLYCOL MONOETHYL ETHER, ISOPROPANOL AND XYLENE AT 20-25 °C
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 458
Also readily soluble in dioxane, diethyl ether, xylene, chloroform, carbon tetrachloride, dimethylformamide. Slightly soluble in petroleum ether.
In water, 25 mg/L at 20 °C
Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 710

3.2.6 Density

1.115 at 20 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-466

3.2.7 Vapor Pressure

0.00000169 [mmHg]
1.69X10-6 mm Hg at 25 °C
Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.

3.2.8 LogP

log Kow = 3.74
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 80

3.2.9 Stability / Shelf Life

Stable under normal conditions. The methylthio group is hydrolized in the presence of strong acids or alkalis.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A384/Aug 87
Estimated shelf life of 80w formulation at least 5 yr, with only slight sensitivity to natural light & extreme temp which would occur normally.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459

3.2.10 Decomposition

When heated to decomposition it emits very toxic fumes of /nitrogen and sulfur oxides/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 606

3.2.11 Corrosivity

Noncorrosive
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A384/Aug 87

3.2.12 Dissociation Constants

pKa = 4.30 (weak base)
Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.

3.2.13 Collision Cross Section

161.23 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
160.2 Ų [M+H]+
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162
160.48 Ų [M+H]+
S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.2.14 Kovats Retention Index

Standard non-polar
1902 , 1910 , 1906 , 1912 , 1935.4 , 1916.9 , 1906.2 , 1910.5 , 1940 , 1911.5 , 1940 , 1921.1 , 1910
Semi-standard non-polar
1939 , 1944 , 1944 , 1945 , 1925.6 , 1926.7 , 1923 , 1924.4 , 1922.5 , 1933.3 , 1925.4 , 1938.3 , 1928.3 , 1923.4 , 1929.7 , 1926.5 , 1933.8 , 1897.3
Standard polar
2793 , 2812 , 2793

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.4.1.1 Human Drugs
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

3.4.2 Pesticides

Herbicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Triazine
Herbicides, Transformation products
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Biocide
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254
Pesticides -> Herbicides -> Triazine herbicides -> Methylthiotriazine herbicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Pesticide (Terbutryn) -> USDA PDB
Pesticide

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 7
View All
NIST Number
245216
Library
Main library
Total Peaks
152
m/z Top Peak
226
m/z 2nd Highest
185
m/z 3rd Highest
170
Thumbnail
Thumbnail
2 of 7
View All
NIST Number
287356
Library
Replicate library
Total Peaks
185
m/z Top Peak
185
m/z 2nd Highest
226
m/z 3rd Highest
170
Thumbnail
Thumbnail

4.1.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

186.081 100

242.144 19.27

158.0495 1.58

91.0324 1.57

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

68.0243 100

85.0509 32.78

158.0495 26.79

74.0058 26.72

116.0277 24.39

Thumbnail
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4.1.3 LC-MS

1 of 52
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
10.255 min
Precursor m/z
242.1434
Precursor Adduct
[M+H]+
Top 5 Peaks

242.1435 999

186.0802 223

187.0822 15

188.0757 7

Thumbnail
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License
CC BY
2 of 52
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
10.253 min
Precursor m/z
242.1434
Precursor Adduct
[M+H]+
Top 5 Peaks

186.0815 999

242.1435 665

187.0825 158

243.1459 51

158.0485 21

Thumbnail
Thumbnail
License
CC BY

4.1.4 Other MS

MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
242.14339
Instrument
JMS-S3000
Instrument Type
MALDI-TOFTOF
Ionization Mode
positive
Top 5 Peaks

186.11901 100

198.04149 46.49

167.14993 33.92

68.13357 28.81

29.13347 28.65

Thumbnail
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License
CC BY-NC-SA

4.2 IR Spectra

4.2.1 FTIR Spectra

1 of 2
Technique
FILM (CAST FROM CHLOROFORM)
Source of Sample
U.S. Epa Repository, Research Triangle Park, North Carolina
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
KBr WAFER
Source of Sample
Riedel-De Haen AG
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Agrochemical Information

8.1 Agrochemical Category

Herbicide
Pesticide active substances -> Herbicides
Herbicides, Transformation products
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticides -> Herbicides -> Triazine herbicides -> Methylthiotriazine herbicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

8.2 Agrochemical Transformations

Terbutryn has known environmental transformation products that include Terbutylazine-2-hydroxy and Irgarol-descyclopropyl.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

8.3 EU Pesticides Data

Active Substance
terbutryn
Status
Not approved [Reg. (EC) No 1107/2009]
Legislation
2002/2076

8.4 USDA Pesticide Data Program

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Herbicides
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

9.2 Absorption, Distribution and Excretion

They are efficiently absorbed from intestine, and presumably there is some absorption across the skin and lung. /Urea-, uracil- and triazine-based herbicides/
Morgan, D. P. Recognition and Management of Pesticide Poisonings. 2nd ed. EPA 540/9-76-011, Washington, DC: U.S. Government Printing Office, Aug. 1976., p. 28
Absorbed through both foliage and roots. It appears to penetrate foliage rapidly, minimizing removal from foliage by rain. /It is/ translocated acropetally through xylem from roots and foliage, accumulating in apical meristems.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459
In mammals, following oral admin, 73-85% is eliminated in metabolized form in feces within 24 hr.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A384/Aug 87

9.3 Metabolism / Metabolites

Terbutryn ... was metabolized by both rats and goats after a single oral dose by one or more of the following pathways: S-demethylation, conversion of thiomethyl into hydroxyl, N-de-ethylation, oxidation of the terminal carbon of the ethyl group to a carboxylic acid, oxidation of a terminal carbon of the t-butyl group to an alcohol or a carboxylic acid, or conjugation with glucuronic acid.
The Royal Society of Chemistry. Foreign Compound Metabolism in Mammals. Volume 6: A Review of the Literature Published during 1978 and 1979. London: The Royal Society of Chemistry, 1981., p. 323
Carbon-labeled terbutryn was admin as single oral doses to rats and goats. Urine was collected at intervals up to 72 hr and then analyzed ... after isolation of glucuronides by chromatographic procedures. Five conjugates isolated and identified were: 2-amino-4-(t-butylamino)-6-(S-glucuronyl)-s-triazine; 2-(t-butylamino)-4-ethylamino-6-(S-glucuronyl)-s-triazine; 2-ethyl-amino-(2-methyl)glucuronylpropyl)amino-6-(S-methylthio)-s-triazine; 2-amino-4-(2-(1-glucuronyl-2-methylpropyl)amino)-6-methylthio-s-triazine; 2-ethylamino-4-(2-(2-methyl propan-1-olyl)amino)-6-(S-glucuronyl)-s-triazine.
Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 540
After administration of terbutryne to rats, urinary metabolites observed ... included: 2-hydroxy terbutryne; 2-amino-4-hydroxy-6-t-butylamino-s-triazine; 2-amino-4-t-butylamino-6-mercapto-s-triazine; two S-glucuronides and two t-butyl-O-glucuronides. Other metabolites were formed by one or a combination of the following reactions: N-alkyl oxidation to alcohols or acids: S-demethylation; N-deethylation; and disulfide formation.
Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 540
Microsomes prepared from livers from 30 to 70 year old patients undergoing liver resection were incubated with 6.3 to 1,000 uM atrazine, terbuthylazine, terbutryne, or ametryne , and the incubation mixtures were analyzed for metabolites. The compounds produced a variety of metabolites indicative of S-oxidation, N-dealkylation, and side chain C-oxidation. The metabolites were formed by processes showing biphasic kinetics, Michaelis constants for the first and second phases varying from 1.4 to 20 uM and from 54 to 530 uM, respectively. Atrazine, terbuthylazine, ametryne, or terbutryne at 25 uM was incubated with human liver microsomes containing substrates for cytochrome-P4501A2 (CYP1A2), cytochrome-P4502A6, cytochrome-P4502D6, cytochrome-P4502C9, cytochrome-P4502C19, cytochrome-P4502E1, or cytochrome-P4503A4 (CYP3A4) isozymes. Other microsomal preparations were incubated with 25 or 600 uM of the S-triazines in the presence or absence of alpha-naphthoflavone (aNF), furafylline, quinidine, sulfaphenazole, diethyl-dithiocarbamate, gestodene, or ketoconazole, inhibitors of various specific cytochrome-P450 (P450) isozymes, at concentrations 5 to 10 times greater than their inhibition constants. Microsomal preparations containing substrates for CYP1A2 and CYP3A4 showed the best correlation with the rates of metabolism of the S-triazines. Only aNF and furafylline, inhibitors of CYP1A2, inhibited metabolism of the S-triazines. A human liver microsomal preparation with demonstrated high levels of flavin containing monooxygenase (FMO) activity and purified recombinant human FMO-3 were incubated with ametryne and terbutryne. The extent of sulfoxidation of the two compounds was determined. No significant formation of sulfoxide metabolites was detected, indicating that the FMO system was not involved in the metabolism of S- triazines by human liver microsomes. The authors conclude that these results clearly identify CYP1A2 as the major phase-I P450 isozyme that is involved in the metabolism of S-triazines by human liver microsomes.
Lang DH et al; Chem Res Toxicol 10 (9): 1037-1044 (1997)
For more Metabolism/Metabolites (Complete) data for TERBUTRYNE (7 total), please visit the HSDB record page.
Terbutryn has known human metabolites that include 2-Hydroxyethylterbutryn, Terbutrynsulfoxide, and t-Butylhydroxy-terbutryn.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

9.4 Mechanism of Action

... Their chief mode of action appears to involve carbohydrate metabolism. The chlorinated s-triazines inhibit starch accumulation by blocking the prodn of sugars. Similar behavior has been shown for the methoxy & methylthio-s-triazines. It has been reported that the s-triazines affect the tricarboxylic acid cycle with activation of phospho-phenyl pyruvate-carboxylase causing the disappearance of sucrose & glyceric acid with the formation of aspartic & malic acids. /S-triazines/
American Conference of Governmental Industrial Hygienists. Documentation of the Threshold Limit Values and Biological Exposure Indices. 5th ed. Cincinnati, OH: American Conference of Governmental Industrial Hygienists, 1986., p. 44
Inhibition of photosynthesis by disruption of light reactions and blockade of electron transport is the mechanism of action of the 1,3,5-triazine herbicides. /1,3,5-Triazines, from table/
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 791
The influence of some s-triazine herbicides on acid phosphatase and phosphodiesterase from corn (Zea mays) roots were investigated. Terbutryn stimulated both phosphatases, whereas prometryn stimulated only the phosphodiesterase. Atrazine desmetryn, prometon, and simazine inhibited acid phosphatase. No effect was exerted by ametryn. The enzyme assays and the kinetic parameters demonstrated that the interferences observed were due to an action on the synthesis of one or both enzymes rather than on the enzyme reactions. The types of the N-alkyl and the chlorine-subsitutuent groups in the structures of the s-triazines tested appear important in determing the degree of the interference.
Scarponi L; Weed Sci 34 (6): 807-10 (1986)

9.5 Transformations

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as selective herbicide for control of annual broadleaf and grass weeds in cereals, sugar cane, maize, other crops, and fallow land; Also used to control algae and submerged plants in waterways, reservoirs, and fish ponds; [HSDB]
Restricted Notes
Cancelled--no longer registered as a pesticide for use in the US; [HSDB]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special Review. (1998) EPA 738-R-98-002, p. 153
For terbutryn (USEPA/OPP Pesticide Code: (080813) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Terbutryn (886-50-0). Available from, as of February 12, 2007: https://npirspublic.ceris.purdue.edu/ppis/
Selective herbicide for control of annual broadleaf & grass weeds in winter wheat, winter barley, sorghum ... (use for wheat is restricted to Washington, Oregon, Idaho, & Utah and use for barley is restricted to Washington, Oregon and Idaho). /Former use/
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459
Preemergence weed control in sugarcane & sunflowers & in mixture with terbuthylazine on peas & potatoes; post-emergence weed control in maize; also used as clarosan for control of algae and submerged vascular plants in waterways, reservoirs & fish ponds. /Former use/
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 780
For more Uses (Complete) data for TERBUTRYNE (7 total), please visit the HSDB record page.

10.1.1 Use Classification

Herbicides, Transformation products
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticides -> Herbicides -> Triazine herbicides -> Methylthiotriazine herbicides
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
HERBICIDES

10.2 Methods of Manufacturing

React 2-chloro-4-ethylamino-6-t-butylamino-1,3,5-triazine with methyl mercaptan in presence of equivalent of sodium hydroxide. Reacting 2-mercapto-4-ethylamino-6-t-butylamino-1,3,5-triazine with methylating agent in presence of sodium hydroxide.
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 545
Terbutryne may be made by reacting terbuthylazine ... with methyl mercaptan in the presence of an equivalent amount of caustic.
Sittig, M. (ed.) Pesticide Manufacturing and Toxic Materials Control Encyclopedia. Park Ridge, NJ: Noyes Data Corporation. 1980., p. 716
Terbutryn is produced by reaction of 2-chloro-4-ethylamino-4,6-butylamino-1,3,5-triazine with methyl mercaptan in the presence of sodium hydroxide.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V39 247 (2003)

10.3 Formulations / Preparations

'Igran' 50wp & 80wp, wettable powder (500 or 800 g active ingredient /kg); 'igram' 500fw, 'clarosan 500fw, prebane 500 fw, soluble concentrate (500 g/L) ...
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 780
Mixed formulations: (terbutryn +) linuron; ... metobromuron; ... neburon; MCPA + simazine: mecoprop + simazine.
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A384/Aug 87
MIXTURES INCLUDE: DICURAN EXTRA, TERBUTRYNE + CHLORTOLURON (1:6); GESAPRIM COMBI (REG NUMBER 8063-10-2), (TERBUTRYNE + ATRAZINE (1:1)); IGRATER (REG NUMBER 52080-96-3), (TERBUTRYNE + METOBROMURON (1:1)); LEXTRA (PAN BRITANNICA IND), (TERBUTRYN + TRIFLURALIN); OPOGARD, SORGOPRIM (1:1), TOPOGARD (7:3) (REG NO 8066-11-3), (TERBUTRYN + TERBUTHYLAZINE); PEAWEED (PAN BRITANNICA IND), (TERBUTRYN + PROMETRYN); PIOTAL, (TERBUTRYN + CHLOROTOLURON + TERBUTHYLAZINE (1:5:4); TEMPO (FARM PROTECTION), SC (150 G TERBUTRYN + 150 G LINURON/L).
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 780

10.4 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies Terbutryne (technical grade) as unlikely to present an acute hazard in normal use; Main Use: herbicide.
WHO (2005) The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2004, International Programme on Chemical Safety, p.35
Applications may be made preemergence or post-emergence in fall or early spring in winter wheat & postemergence in fall or early spring in winter barley. It may be applied preemergence, alone or with aatrex or milogard in grain sorghum. Applications can be made with ground & aerial equipment. ... /It is/ compatible with most other pesticides & fertilizers when used at normal rates.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459
Registration notes: Discontinued in USA.
Farm Chemicals Handbook 1989. Willoughby, OH: Meister Publishing Co., 1989., p. C-282
/In 1995/ Terbutryn /was/ a General Use Pesticide (GUP). The U.S. Environmental Protection Agency had proposed the revocation of all tolerances for residues of terbutryn in or on barley, sorghum, and wheat. They /did/ not plan to recommend action levels to replace the tolerances (Federal Register 59(138):37019). Many terbutryn product registrations had been cancelled. The EPA has classified it as Toxicity Class III-slightly toxic. Products containing terbutryn bear the Signal Word "Caution".
EXTOXNET Extension Toxicology Network: Pesticide Information Profiles. Terbutryn. (Septemberr 1995). Available from, as of March 7, 2007: https://extoxnet.orst.edu/pips/terbutry.htm
For more General Manufacturing Information (Complete) data for TERBUTRYNE (6 total), please visit the HSDB record page.

11 Identification

11.1 Analytic Laboratory Methods

Five classes of triazine herbicides were analyzed by high-performance liq chromatography-mass spectrometry. Separations were performed on a reversed-C8 column, using acetonitrile-water as mobile phase, followed by in-line UV & mass spectral analysis. Positive & negative ion spectra were recorded. Most of herbicides were more sensitive in the positive ion mode. Terbutryne was one the herbicides included in this study.
Parker CE et al; J Chromatogr 242 (1): 77-96 (1982)
RESULTS OF THIN LAYER CHROMATOGRAPHIC SEPARATION (NON-REVERSED PHASE) FOR 2 CHROMATOGRAPHIC SYSTEMS FOR S-TRIAZINE HERBICIDES, ONE OF WHICH WAS TERBUTRYNE, ARE PRESENTED. IN 1 CHROMATOGRAPHIC SYSTEM, THE TLC GLASS PLATES WERE PRECOATED & COVERED WITH SILANIZED SILICA GEL 60-F-254 & IMPREGNATED WITH 20% DIETHYLENE GLYCOL SOLN IN ACETONE. IN THE 2ND SYSTEM, THE SAME PRECOATED GLASS PLATES WERE IMPREGNATED WITH 20% FORMAMIDE SOLN IN ACETONE. MOBILE PHASES ARE GIVEN FOR BOTH.
OGIERMAN L, SILOWIECKI A; J HIGH RESOLUT CHROMATOGR CHROMATOGR COMMUN 4 (7): 357-8 (1981)
A GAS-LIQUID CHROMATOGRAPHIC METHOD FOR THE DETERMINATION OF TERBUTRYN IN WETTABLE POWDER FORMULATIONS IS DESCRIBED. THE SAMPLES WERE EXTRACTED OR DISSOLVED IN CHLOROFORM & CHROMATOGRAPHED ON CARBOWAX 20M. DIELDRIN WAS USED AS INTERNAL STANDARD.
HOFBERG AH, MURPHY RT; J ASS OFF ANAL CHEM 56 (3): 586-90 (1973)
BASIC PROPERTIES OF S-TRIAZINES, EG, TERBUTRYNE, PROPAZINE, SIMAZINE, & PROMETONE, WERE STUDIED BY GAS CHROMATOGRAPHIC, SPECTROPHOTOMETRIC, AND ELECTROCHEMICAL METHODS. INDIVIDUALS S-TRIAZINES CAN BE DIFFERENTIATED BY THEIR RETENTION INDICES.
PACKOVA V, NEMEC I; J CHROMATOGR 148 (1): 273-81 (1978)
For more Analytic Laboratory Methods (Complete) data for TERBUTRYNE (11 total), please visit the HSDB record page.

11.2 Clinical Laboratory Methods

Analytical methodology for the separation and characterization of s-triazine residues in urine was developed. In the sample preparation procedure developed, a urine sample at pH 12 was extracted with hexane 3 times, using sodium chloride as an emulsion inhibitor. The combined hexane extract was dried by passing it through a sodium sulfate column and concentrated by rotary evaporation. The sample was transferred to a graduated centrifuge tube and further concentrated to 0.5 ml under a stream of dry nitrogen. The sample was analyzed by gas chromatography using the Hall electrolytic conductivity detector in the nitrogen-specific mode. Terbutryne was one the triazines.
Erickson M et al; J Agric Food Chem 27 (4): 740-3 (1979)
Procedure for determining s-triazine herbicides /including/ terbutryne in urine & biological tissues by gas chromatography/flame ionization detection is described. Urine samples are extracted with ether & biological tissues with chloroform. Residues obtained after evaporation of solvent are dissolved in dimethylformamide. Most of the lipids can be removed by n-pentane partitioning.
Van den Heede M, Heyndrickx A; Meded Fac Landbouwet, Rijksuniv Gent 41 (2): Pt 2, 1529-42 (1976)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

Note
Pictograms displayed are for 98.5% (320 of 325) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.5% (5 of 325) of reports.
Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302 (49.8%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (57.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (12%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (11.4%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H400 (95.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (85.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 325 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 5 of 325 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 20 notifications provided by 320 of 325 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Acute Tox. 4 (49.8%)

Skin Sens. 1 (57.5%)

Eye Irrit. 2 (12%)

Acute Tox. 4 (11.4%)

Aquatic Acute 1 (95.7%)

Aquatic Chronic 1 (85.8%)

12.1.3 Hazards Summary

For the triazine herbicides, systemic toxicity unlikely unless large amounts are ingested; May cause irritation; [EPA Pesticides, p. 121] Causes ataxia, dyspnea, and convulsions in lethal-dose animal experiments; [HSDB] An eye irritant; [MSDSonline]
The major hazards encountered in the use and handling of terbutryne stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, dermal contact), exposure to this colorless to white, crystalline substance may occur from its manufacture, formulation, and use as an herbicide. Effects from exposure may include skin and eye irritation, nausea, diarrhea, shortness of breath, muscle spasms, ataxia, and anorexia. In activities and situations where over exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. While terbutryne does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving terbutryne, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Terbutryne may be shipped domestically via air, rail, road, and water, in containers bearing the label "Poison". Small dry spills of terbutryne may be placed into a clean, dry, covered container for later disposal (liquid solutions are first absorbed in sand or other noncombustible absorbent). Large liquid spills should be diked far ahead to prevent terbutryne from entering water sources and sewers. Before implementing land disposal of terbutryne, consult with regulatory agencies for guidance.

12.1.4 Fire Potential

Nonflammable.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459

12.1.5 Skin, Eye, and Respiratory Irritations

Some triazines are mildly irritating to skin, eyes, & upper respiratory tract. /Miscellaneous pesticides of low or moderate toxicity/
Morgan, D.P. Recognition and Management of Pesticide Poisonings. EPA 540/9-80-005. Washington, DC: U.S. Government Printing Office, Jan. 1982., p. 85

12.2 Fire Fighting

12.2.1 Fire Fighting Procedures

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Triazine pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 899

12.3 Accidental Release Measures

12.3.1 Cleanup Methods

Environmental considerations- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. /Triazine pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 899
Environmental considerations- water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses /Triazine pesticides, solid, NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 899

12.3.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Noncombustible containers should be crushed & buried under more than 40 cm of soil. /Herbicides/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1039
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
40 CFR 165.9 (a) (7/1/88)
Group II Containers: Noncombustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
40 CFR 165.9 (b) (7/1/88)

12.3.3 Preventive Measures

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Avoid contact with eyes, contact with skin, inhalation of dust, & contamination of food & feed.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 459
Only clean clothing ... should be worn & clothing should be changed daily ... Adequate sanitary facilites & washing water should be provided for workers to wash before meals. Smoking & consumption of alcoholic drinks before & during the handling of herbicides should be forbidden. Contaminated clothing should be removed immediately & a hot bath taken if possible. Personal hygiene should be encouraged. /Herbicides/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1039
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
For more Preventive Measures (Complete) data for TERBUTRYNE (6 total), please visit the HSDB record page.

12.4 Exposure Control and Personal Protection

12.4.1 Personal Protective Equipment (PPE)

The use of personal protective equipment such as glasses, synthetic gloves & /NIOSH/ approved breathing apparatus/ ... is important. /Herbicides/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1039
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticides, solid NOS/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 898

12.5 Transport Information

12.5.1 Shipping Name / Number DOT/UN/NA/IMO

UN 2763; Triazine pesticide, solid, not otherwise specified

12.5.2 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2 (7/1/96)
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
IATA. Dangerous Goods Regulations. 38th ed. Montreal, Canada and Geneva, Switzerland: International Air Transport Association, Dangerous Goods Board, January, 1997., p. 224
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.3097-1, 6193, 6194, 6195 (1988)

12.6 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,3,5-Triazine-2,4-diamine, N-(1,1-dimethylethyl)-N'-ethyl-6-(methylthio)-
Status Regulation (EC)
2002/2076
New Zealand EPA Inventory of Chemical Status
Terbutryn: Does not have an individual approval but may be used under an appropriate group standard

12.6.1 State Drinking Water Guidelines

(FL) FLORIDA 330 ug/l
USEPA/Office of Water; Federal-State Toxicology and Risk Analysis Committee (FSTRAC). Summary of State and Federal Drinking Water Standards and Guidelines (11/93) To Present

12.6.2 FIFRA Requirements

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Terbutryn is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0085; Pesticide type: herbicide; Registration Standard Date: 09/17/86; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Terbutryn; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special Review. (1998) EPA 738-R-98-002, p. 153

13 Toxicity

13.1 Toxicological Information

13.1.1 EPA IRIS Information

Substance
Toxicity Summary
EPA IRIS Summary PDF (Update: Sep-26-1988 )
Critical Effect Systems
Hematologic
Reference Dose (RfD), chronic
1 x 10 ^-3 mg/kg-day

13.1.2 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.001
Oral Chronic Reference Dose Reference
IRIS Current

13.1.3 USGS Health-Based Screening Levels for Evaluating Water-Quality

Chemical
Terbutryn
USGS Parameter Code
38888
Chemical Classes
Pesticide
Noncancer HBSL (Health-Based Screening Level)[μg/L]
6
Reference
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

13.1.4 Evidence for Carcinogenicity

Cancer Classification: Group C Possible Human Carcinogen
USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)

13.1.5 Target Organs

Hematologic

13.1.7 Adverse Effects

Neurotoxin - Other CNS neurotoxin

13.1.8 Acute Effects

13.1.9 Toxicity Data

LC50 (rat) > 8,000 mg/m3/4h

13.1.10 Antidote and Emergency Treatment

/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 157
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 157

13.1.11 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Adverse effects have occurred only rarely as result of ... contact with these herbicides. Most injuries reported have been skin irritation after prolonged contact. In varying degrees these herbicides are likely to produce irritation of gut if ingested in substantial quantity. ... Some compounds of these classes cause irritation of eyes and mucous membranes, particularly if direct contact is protracted. Nausea, vomiting, and diarrhea can be expected to result from ingestion of large quantities. /Urea-, uracil- and triazine-based herbicides/
Morgan, D. P. Recognition and Management of Pesticide Poisonings. 2nd ed. EPA 540/9-76-011, Washington, DC: U.S. Government Printing Office, Aug. 1976., p. 27
/GENOTOXICITY/ ... In this study, the DNA-damaging ability of the herbicide was evaluated in the alkaline single-cell microgel-electrophoresis ("comet") assay by testing terbutryn in the presence of S9 mix (rat liver homogenate containing microsomal enzymes plus cofactors) prepared with liver homogenate from both uninduced (basal) and Aroclor 1254-induced rats. DNA damage was recorded in freshly isolated human peripheral blood leukocytes. A statistically significant increase in the extent of primary DNA damage, more pronounced in the absence of S9 mix, took place only when terbutryn concentrations were high (100 and 150 ug/mL), in the presence of a concomitant mild cytotoxic effect.
Villarini M et al; Cell Biol Toxicol 16 (5): 285-92 (2000)

13.1.12 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Ataxia, dyspnea, and convulsions ... exhibited in lab animals.
Weed Science Society of America. Herbicide Handbook. 4th ed. Champaign, IL: Weed Science Society of America, 1979. of America, 1979., p. 439
/LABORATORY ANIMALS: Acute Exposure/ Rabbit eye irritation with Igran 80W is classified moderately irritating and primary skin irritation with rabbits is only slightly irritating.
Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 461
/LABORATORY ANIMALS: Acute Exposure/ Acute Toxicity: Terbutryn is slightly toxic. It affects the central nervous system in animals leading to incoordination, convulsions, or labored breathing. At extremely high dosages, the animals showed swelling and fluid in the lungs and central nervous system. The dose which kills half of the test animals, the LD50, is 2450-2500 mg/kg for rats and 3884 mg/kg for mice. The LD50 for dermal exposure is greater than 2,000 mg/kg for rabbits.The concentration in air which kills half of the test animals by inhalation, the LC50 (4 hours), is greater than 8 mg of an 80% formulation per liter of air for rats. Terbutryn is not a skin sensitizer.
EXTOXNET Extension Toxicology Network: Pesticide Information Profiles. Terbutryn. (Septemberr 1995). Available from, as of March 7, 2007: https://extoxnet.orst.edu/pips/terbutry.htm
/LABORATORY ANIMALS: Acute Exposure/ Terbutryne is a nonsensitizer. /Technical grade/ /From table/
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1513
For more Non-Human Toxicity Excerpts (Complete) data for TERBUTRYNE (14 total), please visit the HSDB record page.

13.1.13 Non-Human Toxicity Values

LD50 Rabbit dermal >2,000 mg/kg
EXTOXNET Extension Toxicology Network: Pesticide Information Profiles. Terbutryn. (Septemberr 1995). Available from, as of March 7, 2007: https://extoxnet.orst.edu/pips/terbutry.htm
LD50 Rat oral 2450-2500 mg/kg
EXTOXNET Extension Toxicology Network: Pesticide Information Profiles. Terbutryn. (Septemberr 1995). Available from, as of March 7, 2007: https://extoxnet.orst.edu/pips/terbutry.htm
LD50 Rat oral 2045 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 606
LC50 Rat inhalation >8 mg/L/4 hr /80% formulation/
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A384/Aug 87
For more Non-Human Toxicity Values (Complete) data for TERBUTRYNE (8 total), please visit the HSDB record page.

13.1.14 Populations at Special Risk

... For patients who suffer from Na+ desequilibrium, the triazine - human serum albumin binding would change ... /as well as/ the toxicological effect of these herbicides. /Triazine herbicides/
Ismaili L et al; J Chromatog B 780 (2): 467-74 (2002)

13.2 Ecological Information

13.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

13.2.2 Ecotoxicity Values

LD50 Anas platyrhynchos (mallard ducks) oral greater than 2000 mg/kg, 3-4 mo old female /Sample purity 97.8%/
U.S. Department of the Interior, Fish and Wildlife Service. Handbook of Toxicity of Pesticides to Wildlife. Resource Publication 153. Washington, DC: U.S. Government Printing Office, 1984., p. 79
LD50 Pheasant oral greater than 2000 mg/kg, 3 mo old female /Sample purity 97.8%/
U.S. Department of the Interior, Fish and Wildlife Service. Handbook of Toxicity of Pesticides to Wildlife. Resource Publication 153. Washington, DC: U.S. Government Printing Office, 1984., p. 79
LC50; Species: Oncorhynchus mykiss (Rainbow trout, length 2-10 cm, weight 0.5-14 g); Conditions: freshwater; static, 14 °C, pH 6.8-7.6, hardness 5.0-6.0 mg/L CaCO3, dissolved oxygen 12 mg/L; Concentration: 3.0 mg/L for 48 hr
Bathe R et al; Schriftenr Ver Wasser-Boden-Lufthyg Berlin-Dahlem 37: 241-56 (1973) Available from, as of February 1, 2007
LC50 Oncorhynchus mykiss (Rainbow trout, weight 0.8 g) 0.82 mg/L/96 hr at 13 °C (95% confidence limit: 0.56-1.20 mg/L) /static bioassay/
U.S. Department of Interior, Fish and Wildlife Service. Handbook of Acute Toxicity of Chemicals to Fish and Aquatic Invertebrates. Resource Publication No. 137. Washington, DC: U.S. Government Printing Office, 1980., p. 85
For more Ecotoxicity Values (Complete) data for TERBUTRYNE (16 total), please visit the HSDB record page.

13.2.3 Ecotoxicity Excerpts

/BIRDS and MAMMALS/ Practically nontoxic. Bird: Practically nontoxic to upland game birds.
Meister, R.T., Sine, C; Crop Protection Handbook Volume 93. Meister Media Worldwide, Willoughby, OH 2007, p. D-357
/BIRDS and MAMMALS/ The effect of terbutryne on the vitamin A content in the liver of pheasants (Phasianus colchicus colchicus L.) was studied. One hundred forty 10-18 week old pheasants were fed grains treated with terbutryne ad libitum for 4 to 20 days. A significant decrease in the vitamin A content of the liver was observed starting from the 20th day, and reaching 56% of the initial level by 2 weeks after treatment. The reduction of the liver vitamin A level is indicative of the harmful effect of terbutryne.
Schulze H and Treichler J; Dtsch Tieraerztl Wschr 82 (2): 75-80 (1975)
/AQUATIC SPECIES/ Igran in aquatic environment had adverse effect on its population, especially fish. The median lethal effect on carp of exposure for 1-4 days was 8-9 mg/cu m. the toxicity to Leucaspius delineatus was twice that to Carp.
Marcoci S, Ionescu M; Stud: Prot Calitatii Apelor 19: 58-74 (1979)
/AQUATIC SPECIES/ The effects of the herbicide terbutryn on a simple lotic food web were investigated during a 72-day exposure period in five artificial indoor streams in a greenhouse. The model compound terbutryn, an s-triazine and an inhibitor of photosynthesis, was applied once in each stream at nominal concentrations of 0.6, 6, 60, or 600 ug/L. Terbutryn concentrations in the water were analyzed by gas chromatography/mass spectrometry, and an overall time to 50% dissipation (DT50) of 28 days was calculated. The development of aufwuchs and the population growth and development of the oligochaete Lumbriculus variegatus were investigated. ... Terbutryn was toxic to L. variegatus at 23.7 mg/L (96-hr median lethal concentration (LC50)) and 16.5 mg/L (96-hr median effective concentration (EC50)) in static acute toxicity tests. Terbutryn decreased aufwuchs production at 0.6 ug/L in the experimental streams. Population growth of L. variegatus was decreased by 50% at 6 ug/L. The effect of terbutryn on the aufwuchs was a direct effect of decreases in the periphyton. However, the effects on L. variegatus were an indirect effect of terbutryn as a consequence of decrease in the aufwuchs food source and occurred at three-orders-of-magnitude-lower concentrations of terbutryn than the acute toxicity effects. Our study demonstrates the utility of indoor lotic microcosm studies for evaluating both direct and indirect effects of contaminants on aquatic ecosystems.
Brust K et al; Environ Toxicol Chem 20 (9): 2000-7 (2001)
For more Ecotoxicity Excerpts (Complete) data for TERBUTRYNE (10 total), please visit the HSDB record page.

13.2.4 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
6.30e+01
Industrial Soil (mg/kg)
8.20e+02
Tapwater (ug/L)
1.30e+01
MCL (ug/L)
1.00e+02
Risk-based SSL (mg/kg)
1.90e-02
Chronic Oral Reference Dose (mg/kg-day)
1.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

13.2.5 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
1.90e+02
Industrial Soil (mg/kg)
2.50e+03
Tapwater (ug/L)
4.00e+01
MCL (ug/L)
1.00e+02
Chronic Oral Reference Dose (mg/kg-day)
1.00e-03
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

13.2.6 Environmental Fate / Exposure Summary

Terbutryne's production may result in its release to the environment through various waste streams; its former use in the US as a selective herbicide for control of annual broadleaf and grassy weeds may have resulted in its direct release to the environment. If released to air, a vapor pressure of 1.69X10-6 mm Hg at 25 °C indicates terbutryne will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase terbutryne will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 36 hours. Particulate-phase terbutryne will be removed from the atmosphere by wet or dry deposition. If released to soil, terbutryne is expected to have moderate mobility to no mobility based upon Koc values of 366 to 41,757. Terbutryne volatilized <1% to 6% in 2 different soils at 15 and 25 °C. Terbutryne may be susceptible to biodegradation based upon half-lives of 2 and 11 weeks in unfumigated and fumigated soil, respectively. If released into water, terbutryne is expected to adsorb to suspended solids and sediment based upon the Koc values. Terbutryne had degradation half-lives of 6.9 to 30 days under different conditions in pond and river waters. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant of 2.1X10-8 atm-cu m/mol. A BCF of 25 for catfish suggests that bioconcentration in aquatic organisms is low. Occupational exposure to terbutryne may occur through inhalation of dust particles or spray mists and dermal contact with this herbicide during or after its application or at workplaces where ametryne is produced. Although specific monitoring data were not located, the general population may be exposed to terbutryne via contact with contaminated water. (SRC)

13.2.7 Artificial Pollution Sources

Terbutryne's production may result in its release to the environment through various waste streams; its use as a selective herbicide for control of annual broadleaf and grassy weeds(1) will result in its direct release to the environment(SRC).
(1) Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
Residues of terbutryne can enter the environment (soil & water) from runoffs from irrigated fields.
Kadoum AM, Mock DE: J Agric Foof Chem 26 (1): 45-50 (1978)

13.2.8 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 366 - 41,757(2) indicate that terbutryne is expected to have moderate mobility to immobility in soil(SRC). Terbutryne volatilized 6% and <1% in 50 days from a sandy soil (pH 7.9, 97% sand, 0.3% clay, 1.0% organic matter) at 25 and 15 °C, respectively(3). Terbutryne volatilized 3% and <1% in 50 days from another soil (pH 8.9, 49% sand, 29% clay, 1.3% organic matter) at 25 and 15 °C, respectively(3). Terbutryne is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure, 1.69X10-6 mm Hg(4). Terbutryne may be susceptible to biodegradation based upon half-lives of 2 and 11 weeks in unfumigated and fumigated soil, respectively(5).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Gawlik BM et al; Chemosphere 36: 2903-19 (1998)
(3) Alvarez-Benedi J et al; Chemosphere 38: 1583-93 (1999)
(4) Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
(5) Avidov E et al; Weed Sci 33: 457-61 (1985)
AQUATIC FATE: Based on a classification scheme(1), Koc values of 366 - 41,757(2) indicate that terbutryne is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.69X10-6 mm Hg(4), and water solubility, 25 mg/L(5). Sensitized photolysis and photooxidation of terbutryne with photochemically produced hydroxyl radicals may be important removal mechanisms(6-7). According to a classification scheme(8), an estimated BCF of 72(SRC) from its log Kow, 3.74(9) and a regression-derived equation(10) and a reported BCF of 25 in catfish(11) suggest the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Terbutryne had a degradation half-lives of 6.9 - 30 days in river and pond waters under different conditions(12,1).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Gawlik BM et al; Chemosphere 36: 2903-19 (1998)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
(5) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC, Boca Raton, FL. p. 710 (2003)
(6) Khan SU, Gamble DS; J Agric Food Chem 31: 1099-104 (1983)
(7) Rejto M et al; J Agric Food Chem 31: 138-42 (1983)
(8) Franke C et al; Chemosphere 29: 1501-14 (1994)
(9) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 80 (1995)
(10) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(11) Kenaga EE; Ecotox Environ Safety 4: 26-38 (1980)
(12) El-Dib MA, Abou-Waly HF; Water Res 32: 1881-7 (1998)
(13) Muir DCG et al; Weed Res 21: 59-70 (1981)
AQUATIC FATE: HALF-LIFE OF TERBUTRYN IN POND WATER WAS 20-30 DAYS. IN BOTTOM SEDIMENT, CORRESPONDING VALUE WAS 400 DAYS.
MUIR DCG ET AL; PROC ANNU WORKSHOP PESTIC RESIDUE ANAL (WEST CAN) 16TH: 171-3 (1981)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terbutryne, which has a vapor pressure of 1.69X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase terbutryne is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 36 hours(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Terbutryne may be susceptible to sensitized photolysis(4) and photooxidation by photochemically produced hydroxyl radicals(5) based upon data for other methylthio-s-triazine herbicides such as prometryne(5) and ametryne(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Rejto M et al; J Agric Food Chem 31: 138-42 (1983)
(5) Khan SU, Gamble DS; J Agric. Food Chem 31: 1099-104 (1983)

13.2.9 Environmental Biodegradation

AEROBIC: Degradation of terbutryne was analyzed in soil (pH 6.68, 11.54% clay, 64.81% sand, 1.75% organic matter) using a packed core method to give a half-life of 161 (4 °C and 10% moisture content), 31 (25 °C and 10% moisture content), 17 (32 °C and 10% moisture content), 36 (25 °C and 7% moisture content), and 17 days (25 °C and 13% moisture content)(1). In another soil (pH 7.69, 18.22% clay, 44.34% sand, 0.97% organic matter) also using a packed core method half-lives of 227 (4 °C and 10% moisture content), 19 (25 °C and 10% moisture content), 14 (32 °C and 10% moisture content), 31 (25 °C and 7% moisture content), and 14 days (25 °C and 13% moisture content) were given(1). Degradation of terbutryne was analyzed in soil (pH 6.68, 11.54% clay, 64.81% sand, 1.75% organic matter) using a flask method to give a half-life of 17 (4 °C and 10% moisture content), 13 (25 °C and 10% moisture content), 7 (32 °C and 10% moisture content), 9 (25 °C and 7% moisture content), and 9 days (25 °C and 13% moisture content)(1). In another soil (pH 7.69, 18.22% clay, 44.34% sand, 0.97% organic matter), also using a flask method, half-lives of 58 (4 °C and 10% moisture content), 13 (25 °C and 10% moisture content), 8 (32 °C and 10% moisture content), 19 (25 °C and 7% moisture content), and 8 days (25 °C and 13% moisture content) were given(1). Terbutryne degradation in soil which was sterilized by methyl bromide (fumigated) or by solar heating was much slower (half-life approx 11 weeks) than in the soil which was not sterilized (half-life approx 2 weeks)(2). The suppression of terbutryne degradation in the fumigated soil was still evident 8 months after fumigation, similar to the behavior found in autoclaved soil(2). Addition of fungicides also strongly inhibited the degradation of terbutryne in soil(2). These observations suggest that biodegradation accounted for the majority of the terbutryne degradation in soil in these experiments(2). Data from the UK data base as of 1993 gave degradation rates from 7 to 358 days with a mean value of 118.67(3).
(1) Lechon Y et al; J Agric Food Chem 45: 951-4 (1997)
(2) Avidov E et al; Weed Sci 33: 457-61 (1985)
(3) Worral F et al; J Geol Soc 157: 877-84 (2000)
AEROBIC: Half-lives of 240 and 180 days have been reported for degradation of terbutryne in pond and river sediment under static aerobic conditions (loosely capped flasks), respectively(1). Terbutryne had a degradation half-life of 18.2 days following a 40 day lag phase in Nile River water and a 6.9 day half-life after a 38 day lag phase in Nile River water with domestic settled sewage added(2). Terbutryne was applied to 2 farm ponds (A and C) near Winnipeg, Canada, in June 1978 to give 100 ug/L water concentrations(3). The half-life for terbutryne in the ponds ranged from 3 wk in pond C, which contained growths of cattails and duckweed to 30 days in pond A which was free from aquatic macrophytes(3). Biological oxidation of the methylthio-sulfur in terbutryne may occur based upon the report that the methylthio group of the structurally similar herbicide prometryne is oxidized by soil microorganisms to the sulfoxide and sulfone(4). Adaptation and enrichment of viable microbial populations may be necessary for the degradation of methylthio-s-triazines such as terbutryne(5).
(1) Muir DCG, Yarechewski AL; J Environ Sci Health B17: 363-80 (1982)
(2) El-Dib MA, Abou-Waly HF; Water Res 32: 1881-7 (1998)
(3) Muir DCG et al; Weed Res 21: 59-70 (1981)
(4) Kearney PC; Proc Int Biodeg Symp 3rd p. 843-52 (1976)
(5) Kaufman DD, Kearney PC; Res Rev 32: 235-65 (1970)

13.2.10 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of terbutryne with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 36 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Terbutryne may be susceptible to sensitized photolysis(3) and photooxidation by photochemically produced hydroxyl radicals(2) based upon data for other methylthio-s-triazine herbicides such as prometryne(2) and ametryne(3). Infrared studies of interactions of s-triazines such as terbutryne with mineral surfaces indicate that adsorption is usually accompanied by protonation and hydrolysis(4).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Khan SU, Gamble DS; J Agric Food Chem 31: 1099-104 (1983)
(3) Rejto M et al; J Agric Food Chem 31: 138-42 (1983)
(4) White JL; Arch Environ Contam Toxicol 3: 461-9 (1981)

13.2.11 Environmental Bioconcentration

A BCF of 25 was reported in fish for terbutryne(SRC), using catfish (Ictaluris melas), specific conditions not provided(1). According to a classification scheme(2), this BCF suggests that bioconcentration in aquatic organisms is low(SRC). Little potential for bioconcentration of terbutryne was observed in sediment dwelling Chironomus tentans larvae that were living in water-sediment mixtures contaminated with the herbicide(3).
(1) Wang X et al; Chemosphere 32: 1783-93 (1996)
(2) Franke C et al; Chemosphere 29: 1501-14 (1994)
(3) Muir DCG et al; Environ Toxicol Chem 2: 269-81 (1983)

13.2.12 Soil Adsorption / Mobility

Data from the UK data base as of 1993 gave Koc value ranges from 700 to 11,660 with a mean value of 2863.11(1). Koc values were measured for two Kishon River, Israel sediments; Kfar Yehushua was 389.57 (7.1 pH, 30% sand, 30% silt 40% clay 1.63% TOC) and Haifa industrial area was 729.60 (6.8 pH, 30 % sand, 20% silt, 50% clay, 1.25% TOC)(2). Koc values were analyzed for terbutryne in 5 EUROSOILS (country, %Clay, % organic carbon, pH); EUROSOIL1- 41,757 (Italy, 75, 1.3, 5.1), EUROSOIL2- 372.7 (Greece, 22.6, 3.7, 7.4), EUROSOIL3- 788 (United Kingdom, 17.0, 3.45, 5.2), EUROSOIL4- 366.2 (France, 20.3, 1.55, 6.5), EUROSOIL5- 3539 (Germany, 6.0, 9.25, 3.2)(3). Another measured Koc value of 700 was given for an unspecified soil type(4). According to a classification scheme(5), Koc values of 150 to 500 indicate moderate mobility and >5,000 indicate immobility in soil(SRC).
(1) Worral F et al; J Geol Soc 157: 877-84 (2000)
(2) Chefetz B et al; Wat Res 38: 4383-94 (2004)
(3) Gawlik BM et al; Chemosphere 36: 2903-19 (1998)
(4) Kenaga EE; Ecotox Environ Safety 4: 26-38 (1980)
(5) Swann RL et al; Res Rev 85: 16-28 (1983)
Terbutryne was classified as immobile in soil thin-layer and thick-layer chromatography and soil-column leaching experiments with sandy loam and silty clay soils in which the Rf range for terbutryne was 0.00-0.10(1). Adsorption of 96-98% and 86-97%, respectively, of the terbutryne applied to an unlimed and limed silt loam soil has been observed(2). Evidence has been reported that indicates that the basicity of s-triazine herbicides, such as terbutryne, is not the main factor governing adsorption to soil humic acids(3). It has been shown that the ability of s-triazines herbicides to act as electron donors to electron acceptor quinone-like units of humic acids also plays an important role in the adsorption(4). Adsorption of terbutryne is favored in soils containing higher concn of clay and organic matter and leaching is limited by adsorption to certain soil constituents(5). Adsorption is reversible and desorption can occur readily depending on conditions including temperature, moisture, and pH(5). Simulated field conditions for a loam soil (pH 7.8, 63.4% sand, 24.6% silt, 12.0% clay, 1.01% organic matter), under saturated field conditions and an application rate of 10 kg/ha of terbutryne gave leaching results of; 5.25, 0.30, 0.03, <0.01, and <0.01 ppm at depths of 0 to 6, 6 to 12, 12 to 18, 18 to 24, and 24 to 30 cm, respectively, after 10 days(6). Terbutryne was found at 0.3% of the applied amount in runoff water and sediment from a rain water simulated sample after 12 hours from unlimed soil(7).
(1) Helling CS, Dragun J; pp 43-88 in Test Protocols for Environmental Fate and Movement of Toxicants. Proc Symp AOAC (1981)
(2) Gaynor JD, Volk VV; Environ Sci Technol 15: 440-3 (1981)
(3) Senesi N, Testini C; Geoderma 28: 129-46 (1982)
(4) Senesi N, Testini C; Chemosphere 13: 461-8 (1984)
(5) WSSA; Herbicide Handbook p 244-6 (1983)
(6) Gomezdebarreda D et al; Sci Tot Environ 132: 155-65 (1993)
(7) Gaynor JD, Volk VV; Environ Sci Technol 15: 440-3 (1981)

13.2.13 Volatilization from Water / Soil

The Henry's Law constant for terbutryne is estimated as 2.1X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.69X10-6 mm Hg(1), and water solubility, 25 mg/L(2). This Henry's Law constant indicates that terbutryne is expected to be essentially nonvolatile from water surfaces(3). However, terbutryne volatilized 6% and <1% in 50 days from a sandy soil (pH 7.9, 97% sand, 0.3% clay, 1.0% organic matter) at 25 and 15 °C, respectively(4). Terbutryne volatilized 3% and <1% in 50 days from another soil (pH 8.9, 49% sand, 29% clay, 1.3% organic matter) at 25 and 15 °C, respectively(4).
(1) Tomlin CDS, ed. Terbutryn (886-50-0). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council.
(2) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC, Boca Raton, FL. p. 710 (2003)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Alvarez-Benedi J et al; Chemosphere 38: 1583-93 (1999)

13.2.14 Environmental Water Concentrations

GROUNDWATER: Terbutryne was not detected in groundwater from new wells in the Northern Italy province of Bergamo which were shown to contain simazine and propazine(1). Terbutryne was not detected (detection limit 0.05 ug/L) in 303 well water samples from 12 Midwest states in the summer of 1991 and 66 samples in the summer of 1992(2). Terbutryne was not detected (detection limit 0.05 ug/L) in 106 municipal well water samples from Iowa in the summer of 1995(3), and 88 samples in the summer of 1996(4). Terbutryne has been identified in 1+ Netherlands ground water sample at a concentration of 2.4 ug/L, number of total samples and locations not reported(5). Well water samples taken from Spanish citrus orchards in 1989 and 1999 contained no terbutryne(6).
(1) Bagnati R et al; Chemosphere 17: 59-65 (1988)
(2) Kolpin DW et al; J Environ Qual 24: 1125-32 (1995)
(3) Kolpin DW et al; Ground Water 35: 679-88 (1997)
(4) Kolpin DW et al; Arch Environ Contam Toxicol 35: 385-90 (1998)
(5) Vandenberg R, Vanderlinden TMA; IN: Environ Sci Pollut Control Ser 11(Groundwater Contam and Control) pp. 293-313 (1994)
(6) Dorfler U et al; Chemosphere 35: 99-106 (1997)
DRINKING WATER: Terbutryne was not detected in US drinking water samples compiled by the National Pesticide Survey(1).
(1) US EPA; US EPA Off Water Off Pest Toxic Sub Fall 1990. NTIS PB93-116 010 17 pp. (1990)
SURFACE WATER: Terbutryne was detected in 19 of 20 samples with a concn range of 2.0-19 ng/L in samples taken from the River Elbe at Zollenspieker, Germany in 1992-1993(1). Terbutryne was detected in 19 of 20 samples with a concn range of 2.0-12 ng/L in samples taken from the River Elbe at Seemannshoft, Germany in 1992-1993(1). Terbutryne has been identified in Dutch surface water, concentrations and locations not reported(2). Terbutryne was not found in fresh surface water samples in England, Wales and the Anglian region, number of total samples and locations not reported(3). Terbutryne was not found in estuaries and coastal water samples in England and Wales(3). Terbutryne was not found in surface water samples taken at 149 sites in 10 Midwestern states; 55 samples taken before planting (3-4/1989), 132 after planting (5-6/1989) and 145 taken at harvest time (10-11/1989)(4). 53 rivers in the Midwest, covering 9 states were analyzed for terbutryne, none of the 50 samples taken in 1989, 52 samples in 1990, 52 samples in 1994 or 50 samples taken in 1995 contained terbutryne(5). Samples taken in April and June of 1990 from the Adige river in Italy contained no terbutryne(6). Terbutryne was identified in water samples from tailwater pits used to collect irrigation runoff(7).
(1) Gotz R et al; Chemosphere 36: 2103-18 (1998)
(2) Oskam G et al; Water Supply 11: 1-17 (1993)
(3) Stangroom SJ et al; Environ Technol 19: 643-66 (1998)
(4) Thurman EM et al; Environ Sci Technol 26: 2440-7 (1992)
(5) Battaglin WA, Goolsby DA; Environ Sci Technol 33: 2917-25 (1999)
(6) Benfenati E et al; Chemosphere 21: 1411-21 (1990)
(7) Kadoum AM, Mock DE; J Agric Food Chem 26: 45-50 (1978)
RAIN/SNOW/FOG: Terbutryne was not detected in rain water samples taken from Mar to Nov 1996 from samples collected in Hannover, Germany(1). Terbutryne was detected in Paris, France rain water samples taken 3/3/1991 at 34 ng/L and 6/20/1991 at 25 ng/L(2). Terbutryne was not detected in Paris rain water samples taken 9/25, 10/30, 11/11 and 12/16-18/1991(2).
(1) Jager ME et al; Int J Environ Anal Chem 70: 149-62 (1998)
(2) Chevreuil M, Garmouma M; Chemosphere 27: 1605-8 (1993)

13.2.15 Sediment / Soil Concentrations

SEDIMENT: Terbutryne was identified in soil sediment samples from tailwater pits located in Haskell County, Kansaswhich, used to collect irrigation runoff from fields of corn or grain sorghum and sampled in May, June, July, August, and November, 1974(1).
(1) Kadoum AM, Mock DE; J Agric Food Chem 26: 45-50 (1978)

13.2.16 Fish / Seafood Concentrations

Terbutryne was reported at <5.0 ug/kg wet weight in zebra mussels (Dreissena polymorpha) and eels (Anguilla anguilla) from the Rhine-Meuse river delta in The Netherlands(1).
(1) Hendriks AJ et al; Environ Toxicol Chem 17: 1885-98 (1998)

13.2.17 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 567 workers (13 of these are female) are potentially exposed to terbutryne in the US(1). The NOES Survey does not include farm workers. Occupational exposure to terbutryne may occur through inhalation of dust particles or spray mists and dermal contact with this herbicide during or after its application or at workplaces where ametryne is produced(SRC). Although specific monitoring data were not located, the general population may be exposed to terbutryne via contact with contaminated water(SRC).
(1) NIOSH; International Safety Cards. Terbutryne. 886-50-0. Available at http//www.cdc.gov/niosh/ipcs/nicstart.html as of Dec 2006.

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Chemical Co-Occurrences in Literature

14.5 Chemical-Gene Co-Occurrences in Literature

14.6 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 KEGG: Pesticides

18.4 ChemIDplus

18.5 UN GHS Classification

18.6 EPA CPDat Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 CCSBase Classification

18.9 EPA DSSTox Classification

18.10 EPA Substance Registry Services Tree

18.11 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1,3,5-Triazine-2,4-diamine, N-(1,1-dimethylethyl)-N'-ethyl-6-(methylthio)-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. EPA Integrated Risk Information System (IRIS)
  7. European Chemicals Agency (ECHA)
    LICENSE
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  37. Springer Nature
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  42. GHS Classification (UNECE)
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CONTENTS