8230 J. Agric. Food Chem., Vol. 56, No. 17, 2008
Lin et al.
curus myosuroides (Black-Grass). Pestic. Biochem. Physiol. 1999,
65 (3), 169–180.
sis, and vaporization. EnViron. Sci. Technol. 1975, 9 (13), 1144–
1150.
(5) Tal, A.; Romano, M. L.; Stephenson, G. R.; Schwan, A. L.; Hall,
J. C. Glutathione conjugation: A detoxification pathway for
fenoxaprop-ethyl in barley, crabgrassl, oat, and wheat. Pestic.
Biochem. Physiol. 1993, 46 (3), 190–199.
(20) Zertal, A.; Sehili, T.; Boulle, P. Photochemical behaviour of
4-chloro-2-methylphenoxyacetic acids—Influence of pH and ir-
radiation wavelength. J. Photochem. Photobiol. A 2001, 146 (1–
2), 37–48.
(6) Lin, J.; Chen, J. W.; Cai, X. Y.; Qiao, X. L.; Huang, L. P.; Wang,
D.; Wang, Z. Evolution of toxicity upon hydrolysis of fenoxaprop-
p-ethyl. J. Agric. Food Chem. 2007, 55 (18), 7626–7629.
(7) Toole, A. P.; Crosby, D. G. Environmental persistence and fate
of feoxaprop-ethyl. EnViron. Toxicol. Chem. 1989, 8, 1171–1176.
(8) Bravo, H. R.; Copaja, S. V.; Lazo, W. Antimicrobial activity of
natural 2-benzoxazolinones and related derivatives. J. Agric. Food
Chem. 1997, 45 (8), 3255–3257.
(21) Zablotowicz, R. M.; Hoagland, R. E.; Staddon, W. J.; Locke, M. A.
Effects of pH on chemical stability and de-esterification of
fenoxaprop-ethyl by purified enzymes, bacterial extracts, and soils.
J. Agric. Food Chem. 2000, 48 (10), 4711–4716.
(22) Hoagland, R. E.; Zablotowicz, R. M. Biotransformations of
fenoxaprop-ethyl by fluorescent Pseudomonas strains. J. Agric.
Food Chem. 1998, 46 (11), 4759–4765.
(23) Yaacoby, T.; Hall, J. C.; Stephenson, G. R. Influence of fenchlo-
razole-ethyl on the metabolism of fenoxaprop-ethyl in wheat,
barley, and crabgrass. Pestic. Biochem. Physiol. 1991, 41, 296–
304.
(9) Hoagland, R. E.; Zablotowicz, R. M. Biotransformations of
fenoxaprop-ethyl by fluorescent Pseudomonas strains. J. Agric.
Food. Chem. 1998, 46 (11), 4759–4765.
(10) OECD. Guidelines for Testing Chemicals. 202. Daphnia sp. Acute
Immobilization Test and Reproduction Test; Organisation for
Economic Co-operation and Development: Par´ıs, 1984.
(11) Liu, S. Z.; Li, Q. X. Photolysis of spinosyns in seawater, stream
water and various aqueous solutions. Chemosphere 2004, 56 (11),
1121–1127.
(12) Tissot, A.; Boule, P.; Lemaire, J. Photochemistry and environment.
VII. The photohydrolysis of chlorobenzene. Studies of the excited
state involved. Chemosphere 1984, 13 (3), 381–389.
(13) Chu, W.; Tsui, S. M. Photoreductive model of disperse orange
11 in aqueous acetone and triethylamine. J. EnViron. Eng. ASCE
2001, 127 (8), 741–747.
(24) Meunier, L.; Boule, P. Direct and induced phototransformation
of mecoprop [2-(4-chloro-2-methylphenoxy)propionic acid] in
aqueous solution. Pest Manage. Sci. 2000, 56 (12), 1077–1085.
(25) Climent, M. J.; Miranda, M. A. Photodegradation of dichlorprop
and 2-naphthoxyacetic acid in water. Combined GC-MS and GC-
FTIR study. J. Agric. Food Chem. 1997, 45 (5), 1916–1919.
(26) Schuurmann, G.; Aptula, A. O.; Kuhne, R.; Ebert, R. U. Stepwise
discrimination between four modes of toxic action of phenols in
the Tetrahymena pyriformis assay. Chem. Res. Toxicol. 2003, 16
(8), 974–987.
(27) Schultz, T. W.; Sinks, G. D.; Cronin, M. T. D. Quinone-induced
toxicity to Tetrahymena: Structure-activity relationships. Aquat.
Toxicol. 1997, 39 (3-4), 267–278.
(28) Cai, X. Y.; Liu, W. P.; Jin, M. Q.; Lin, K. D. Relation of diclofop-
methyl toxicity and degradation in algae cultures. EnViron.
Toxicol. Chem. 2007, 26 (5), 970–975.
(14) Walse, S. S.; Morgan, S. L.; Kong, L.; Ferry, J. L. Role of
dissolved organic matter, nitrate, and bicarbonate in the photolysis
of aqueous fipronil. EnViron. Sci. Technol. 2004, 38 (14), 3908–
3915.
(15) Peng, Z.; Wu, F.; Deng, N. S. Photodegradation of bisphenol A
in simulated lake water containing algae, humic acid and ferric
ions. EnViron. Pollut. 2006, 144 (3), 840–846.
(29) DeLorenzo, M. E.; Scott, G. I.; Ross, P. E. Toxicity of pesticides
to aquatic microorganisms: A review. EnViron. Toxicol. Chem.
2001, 20 (1), 84–98.
(16) Wang, L.; Zhang, C. B.; Wu, F.; Deng, N. S. Photodegradation
of aniline in aqueous suspensions of microalgae. J. Photochem.
Photobiol. B 2007, 87 (1), 49–57.
(30) Macias, F. A.; Marin, D.; Oliveros-Bastidas, A.; Castellano, D.;
Simonet, A. M.; Molinillo, J. M. G. Structure-activity relation-
ships (SAR) studies of benzoxazinones, their degradation products
and analogues. Phytotoxicity on standard target species (STS). J.
Agric. Food Chem. 2005, 53 (3), 538–548.
(31) Jia, C. H.; Kudsk, P.; Mathiassen, S. K. Joint action of benzox-
azinone derivatives and phenolic acids. J. Agric. Food Chem.
2006, 54 (11), 1049–1057.
(17) Fisher, J. M.; Reese, J. G.; Pellechia, P. J.; Moeller, P. L.; Ferry,
J. L. Role of Fe(III), phosphate, dissolved organic matter, and
nitrate during the photodegradation of domoic acid in the marine
environment. EnViron. Sci. Technol. 2006, 40 (7), 2200–2205.
(18) Smith, A. E. Persistence and transformation of the herbicides
[
14C]fenoxaprop-ethyl and [14C]fenthiaprop-ethyl in two prairie
soils under laboratory and field conditions. J. Agric. Food Chem.
1985, 33 (3), 483–488.
(19) Zepp, R. G.; Lee Wolfe, N.; Gordon, J. A.; Baughman, G. L.
Dynamics of 2, 4-D esters in surface waters: hydrolysis, photoly-
Received for review April 30, 2008. Revised manuscript received July
7, 2008. Accepted July 8, 2008.
JF801341S