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Pesticide metabolism in plants and microorganisms

  • Laura L. Van Eerd (a1), Robert E. Hoagland (a2), Robert M. Zablotowicz (a2) and J. Christopher Hall
Abstract

Understanding pesticide metabolism in plants and microorganisms is necessary for pesticide development, for safe and efficient use, as well as for developing pesticide bioremediation strategies for contaminated soil and water. Pesticide biotransformation may occur via multistep processes known as metabolism or cometabolism. Cometabolism is the biotransformation of an organic compound that is not used as an energy source or as a constitutive element of the organism. Individual reactions of degradation–detoxification pathways include oxidation, reduction, hydrolysis, and conjugation. Metabolic pathway diversity depends on the chemical structure of the xenobiotic compound, the organism, environmental conditions, metabolic factors, and the regulating expression of these biochemical pathways. Knowledge of these enzymatic processes, especially concepts related to pesticide mechanism of action, resistance, selectivity, tolerance, and environmental fate, has advanced our understanding of pesticide science, and of plant and microbial biochemistry and physiology. There are some fundamental similarities and differences between plant and microbial pesticide metabolism. In this review, directed to researchers in weed science, we present concepts that were discussed at a symposium of the American Chemical Society (ACS) in 1999 and in the subsequent book Pesticide Biotransformation in Plants and Microorganism: Similarities and Divergences, edited by J. C. Hall, R. E. Hoagland, and R. M. Zablotowicz, and published by Oxford University Press, 2001.

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Corresponding author
Corresponding author. Department of Environmental Biology, University of Guelph, Guelph, ON, Canada N1G 2W1; jchall@evb.uoguelph.ca
References
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Alexander, M. 1999. Biodegradation and Bioremediation. 2nd ed. San Diego, CA: Academic. 453 p.
Anderson, M. P. and Gronwald, J. W. 1991. Atrazine resistance in a velvetleaf (Abutilon theophrasti) biotype due to enhanced glutathione S-transferase activity. Plant Physiol. 96:104110.
Andreae, W. A. and Good, N. E. 1957. Studies on 3-indoleacetic acid metabolism. IV. Conjugation with aspartic acid and ammonia as processes in the metabolism of carboxylic acids. Plant Physiol. 32:566572.
Andreoni, V., Colombo, M., Gennari, M., Negre, M., and Ambosoli, R. 1994. Cometabolic degradation of acifluorfen by a mixed microbial culture. J. Environ. Sci. Health B 29:963987.
Arjmand, M. and Sandermann, H. Jr. 1985. Mineralization of chloroaniline/lignin conjugates and of free chloroanilines by the white rot fungus Phanerochaete chrysosporium . J. Agric. Food Chem. 40:20012007.
Armengaud, J. and Timmis, K. N. 1997. The reductase RedA2 of the multicomponent dioxin dioxygenase system of Sphingomonas sp. RW1 is related to class-I cytochrome P450-type reductases. Eur. J. Biochem. 247:833842.
Armstrong, R. N. 1994. Glutathione S-transferases: structure and mechanism of an archetypical detoxication enzyme. Adv. Enzymol. Relat. Areas Mol. Biol. 69:144.
Avila, L. Z. and Frost, J. W. 1988. Monomeric metaphosphate formation during radical-based dephosphorylation. J. Am. Chem Soc. 110:79047906.
Avila, L. Z. and Frost, J. W. 1989. Phosphonium ion fragmentations relevant to organophosphonate biodegradation. J. Am. Chem Soc. 111:89698970.
Balba, M. H. and Saha, J. G. 1974. Degradation of matacil by the ascorbic acid oxidation system. Bull. Environ. Contam. Toxicol. 11:193200.
Banks, M. K., Lee, E., and Schwab, A. 1999. Evaluation of dissipation mechanisms for benzo[a]pyrene in the rhizosphere of tall fescue. J. Environ. Qual. 28:294298.
Barik, S. and Munnecke, D. M. 1982. Enzymatic hydrolysis of concentrated diazinon in soil. Bull. Environ. Contam. Toxicol. 29:235239.
Barkovskii, A. L. 2001. Microbial reductive dehalogenation in the rhizosphere. Pages 4056 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Barkovskii, A. L. and Adriaenes, P. 1998. Impact of humic constituents on microbial dechlorination of polychlorinated dioxins. Environ. Toxicol. Chem. 17:10131020.
Barkovskii, A. L., Bouillant, M. L., and Balandreau, J. 1994. Polyphenolic compounds respired by bacteria. Pages 2842 In Anderson, T. A. and Coats, J. R., eds. Bioremediation through Rhizosphere Technology. ACS Symposium Series 563. Washington, DC: American Chemical Society.
Barkovskii, A. L., Bouillant, M. L., Jocteur-Monrozier, L., and Balandreau, J. 1995. Azospirillum strains use phenolic compounds as intermediates for electron transfer under oxygen-limiting conditions. Microbial Ecol. 29:99144.
Barr, D. P. and Augst, S. D. 1994. Pollutant degradation by white rot fungi. Rev. Environ. Contam. Toxicol. 138:4972.
Barrentine, W. L., Edwards, C. J. Jr., and Hartwig, E. E. 1976. Screening soybeans for tolerance to metribuzin. Agron. J. 68:351353.
Barrentine, W. L., Hartwig, E. E., Edwards, C. J. Jr., and Kilen, T. C. 1982. Tolerance of three soybean (Glycine max) cultivars to metribuzin injury. Weed Sci. 30:344348.
Barrett, M. 1998. Cloning and Heterologous Expression of Pesticide Metabolizing Cytochrome P450 Genes. Springfield, VA: National Technical Information Service, Fedrip Database.
Barrett, M. 2000. The role of cytochrome P450 enzymes in herbicide metabolism. Pages 2537 In Cobbs, A. H. and Kirkwood, R. C., eds. Herbicides and Their Mechanisms of Action. Sheffield, Great Britain: Sheffield Academic.
Barry, G., Kishore, G., Padgette, S. et al. 1992. Inhibitors of amino acid biosynthesis: strategies for imparting glyphosate tolerance to crop plants. Pages 139145 In Singh, B. K., Flores, H. E., and Shannon, J. C., eds. Biosynthesis and Molecular Regulation of Amino Acids in Plants. Madison, WI: American Society of Plant Physiology.
Bayley, C., Trolinder, N., Ray, C., Morgan, M., Quesenberry, J. E., and Ow, D. W. 1992. Engineering 2,4-D resistance into cotton. Theor. Appl. Genet. 83:645649.
Benyon, K. I., Stoydin, G., and Wright, A. N. 1972a. The breakdown of the triazine herbicide cyanazine in soils and maize. Pestic. Sci. 3:293305.
Benyon, K. I., Stoydin, G., and Wright, A. N. 1972b. The breakdown of the triazine herbicide cyanazine in wheat and potatoes grown under indoor conditions in treated soils. Pestic. Sci. 3:379387.
Bickerstaff, G. F. 1997. Immobilization of enzymes and cells: Some practical considerations. Pages 110 In Bickerstaff, G. F., ed. Methods in Biotechnology 1. Totowa, NJ: Humana.
Bilang, J. and Sturm, A. 1995. Cloning and characterization of a glutathione S-transferase that can be photolabelled with 5-azido-indole-3-acetic acid. Plant Physiol. 109:253260.
Blaabjerg, V. and Finster, K. 1998. Sulphate reduction associated with roots and rhizomes of the marine macrophyte Zostera marina . Aquat. Microb. Ecol. 15:311314.
Blake-Kalff, M.M.A., Randall, R. A., and Coleman, J.O.D. 1997. Compartmentation of detoxified xenobiotics in plant cells. Pages 245259 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic.
Bollag, J.-M. 1972. Biochemical transformation of pesticides by soil fungi. CRC Crit. Rev. Microbiol. 2:3558.
Bolwell, G. P., Bozak, K., and Zimmerlin, A. 1994. Plant cytochrome P450. Phytochemistry 37:14911505.
Boundy-Mills, K. L., de Souza, M. L., Mandelbaum, R. T., Wackett, L. P., and Sadowsky, M. J. 1997. The atzB gene of Pseudomonas sp. strain ADP encodes the second enzyme of a novel atrazine degradation pathway . Appl. Environ. Microbiol. 63:916923.
Bowling, C. C. and Hudgins, H. R. 1966. The effect of insecticides on the selectivity of propanil in rice. Weeds 14:9495.
Bradshaw, W. H., Conrad, H. E., Corey, E. J., Gunsalus, I. C., and Lednicer, D. 1959. Microbial degradation of (+)-camphor. J. Am. Chem. Soc. 81:5507.
Breaux, E. J. 1987. Initial metabolism of acetochlor in tolerant and susceptible seedlings. Weed Sci. 35:463469.
Breaux, E. J., Patanella, J. E., and Sanders, E. F. 1987. Chloroacetanilide herbicide selectivity: analysis of glutathione and homoglutathione in tolerant, susceptible, and safened seedlings. J. Agric. Food Chem. 35:474478.
Brenner, S. 1988. The molecular evolution of genes and proteins: a tale of two serines. Nature 334:528530.
Brown, H. M. and Kearney, P. C. 1991. Plant biochemistry, environmental properties and global impact of the sulfonylurea herbicides. Pages 3249 In Baker, D. R., Fenyes, J. G., and Moberg, W. K., eds. Synthesis and Chemistry of Agrochemicals II. American Chemical Society (ACS) Symposium Series 443. Washington, DC: American Chemical Society.
Bryant, D. W., McCalla, D. R., Leeksma, M., and Laneuville, P. 1981. Type I nitroreductases of Escherichia coli . Can. J. Microbiol. 27:8186.
Buckland, J. L., Collins, R. F., and Pullin, E. M. 1973. Metabolism of bromoxynil octanoate in growing wheat. Pestic. Sci. 4:149162.
Bujacz, B., Wieczorek, P., Krzysko-Lupicka, T., Golab, Z., Lejczak, B., and Kafarski, P. 1995. Organophosphonate utilization by the wild-type strain of Penicillium notatum . Appl. Environ. Microbiol. 61:29052910.
Cabanne, F., Huby, D., Gaillardon, P., Scalla, R., and Durst, F. 1987. Effect of the cytochrome P-450 inactivator 1-aminobenzotriazole on the metabolism of chlortoluron and isoproturon in wheat. Pestic. Biochem. Physiol. 28:371380.
Cai, B., Vuilleumier, S., and Wackett, L. P. 1998. Purification and characterization of the mutant enzyme W117Y of the dichloromethane dehalogenase from Methylophilus sp. strain DM11. Ann. N. Y. Acad. Sci. 264:210213.
Canivenc, M.-C., Cagnac, B., Cabanne, F., and Scalla, R. 1989. Induced changes of chlorotoluron metabolism in wheat cell suspension cultures. Plant Physiol. Biochem. 27:193201.
Carey, V. F. III, Duke, S. O., Hoagland, R. E., and Talbert, R. E. 1995a. Resistance mechanism of propanil-resistant barnyardgrass I. Absorption, translocation, and site of action studies. Pestic. Biochem. Physiol. 52:182189.
Carey, V. F. III, Hoagland, R. E., and Talbert, R. E. 1995b. Verification and distribution of propanil-resistant barnyardgrass (Echinochloa crus-galli) in Arkansas. Weed Technol. 9:366372.
Carey, V. F. III, Hoagland, R. E., and Talbert, R. E. 1997. Resistance mechanism of propanil-resistant barnyardgrass. II. In-vivo metabolism of the propanil molecule. Pestic. Sci. 49:333338.
Carringer, R. D., Rieck, C. E., and Bush, L. P. 1978. Effect of R-25788 on EPTC metabolism in corn (Zea mays). Weed Sci. 26:167171.
Cassidy, M. B., Lee, H., Trevors, J. T., and Zablotowicz, R. M. 1999. Chlorophenol and nitrophenol metabolism by Sphingomonas sp. UG30. J. Ind. Microbiol. Biotechnol. 23:232241.
Cerniglia, C. E. 1992. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 3:351368.
Chaudhry, G. R., Ali, A. N., and Wheeler, W. B. 1988. Isolation of a methyl parathion-degrading Pseudomonas sp. that possesses DNA homologous to the opd gene from a Flavobacterium sp. Appl. Environ. Microbiol. 54:288293.
Cheah, U. B., Kirkwood, R. C., and Lum, K.- Y. 1998. Degradation of four commonly used pesticides in Malaysian agricultural soils. J. Agric. Food Chem. 46:12171223.
Chen, C. M., Ye, Q. Z., Zhu, Z., Wanner, B. L., and Walsh, C. T. 1990. Molecular biology of carbon-phosphorus bond cleavage. J. Biol. Chem. 265:44614471.
Choi, K. D., Jeohn, G. H., Rhee, J. S., and Yoo, O. J. 1990. Cloning and nucleotide sequence of an esterase gene from Pseudomonas fluorescens and expression of the gene in Escherichia coli . Agric. Biol. Chem. 54:20392045.
Colbert, S. F., Schroth, M. N., Weinhold, A. R., and Hendson, M. 1993. Enhancement of population densities of Pseudomonas putida PpG7 in agricultural ecosystems by selective feeding with the carbon source salicylate. Appl. Environ. Microbiol. 59:20642070.
Cole, D. J., Cummins, I., Hutton, P. J., Dixon, D. P., and Edwards, R. 1997. Glutathione transferases in crops and major weeds. Pages 139154 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic.
Cook, A. M. 1987. Biodegradation of s-triazine xenobiotics. FEMS Microbiol. Rev. 46:93116.
Cook, A. M. and Hutter, R. 1981. s-Triazines as nitrogen sources for bacteria degradation of herbicides. J. Agric. Food Chem. 29:11351143.
Cordeiro, M. L., Pompliano, D. L., and Frost, J. W. 1986. Degradation and detoxification of organophosphonates: cleavage of the carbon to phosphorus bond. J. Am. Chem. Soc. 108:332334.
Criddle, C. S., McCarty, P. L., Eliott, M. C., and Barker, J. F. 1986. Reduction of hexachloroethane to tetrachloroethylene in groundwater. Contam. Hydrol. 1:133142.
Crowley, D. E., Alvey, S., and Gilbert, E. S. 1997. Rhizosphere ecology of xenobiotic-degrading microorganisms. Pages 2036 In Kruger, E. L., Anderson, T. A., and Coats, J. R., eds. Phytoremediation of Soil and Water Contaminants. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Crowley, D. E., Luepromechai, E., and Singer, A. 2001. Metabolism of xenobiotics in the rhizosphere. Pages 333352 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Cullimore, D. R. and Kohout, M. 1974. Isolation of a bacterial degrader of the herbicide bromoxynil from a Saskatchewan soil. Can. J. Microbiol. 20:14491452.
Cygler, M., Grochulski, P., and Schrag, J. B. 1995. Structural determinants defining common stereoselectivity of lipases toward secondary alcohols. Can. J. Microbiol. 41 (Suppl. 1): 289296.
da Silva, J. F. and Warren, G. F. 1976. Effect of stage of growth on metribuzin tolerance. Weed Sci. 24:612615.
Davies, J., Caseley, J. C., Jones, O., Barrett, M., and Polge, N. 1997. Mode of action of napthalic anhydride as a safener for the herbicide AC263222 in maize. Pestic. Sci. 52:2938.
Davies, J., Caseley, J. C., and Jones, O.T.G. 1993. Enhancement of AC 263222 metabolism by the herbicide safener naphthalic anhydride. Proc. Br. Crop Prot. Conf.—Weeds. pp. 195200.
De Kok, L. J., Maas, F. M., Godeke, J., Haaksma, A. B., and Kuiper, P.J.C. 1986. Glutathione, a tripeptide which may function as a temporary storage compound of excessive reduced sulphur in H2S fumigated spinach plants. Plant Soil. 91:349352.
de Souza, M. L., Sadowsky, M. J., and Wackett, L. P. 1996. Atrazine chlorohydrolase from Pseudomonas sp. strain ADP: gene sequence, enzyme purification and protein characterization. J. Bacteriol. 178:48944900.
de Souza, M. L., Seffernick, J., Martinez, B., Sadowsky, M. J., and Wackett, L. P. 1998a. The atrazine catabolism gene atzABC are widespread and highly conserved. J. Bacteriol. 180:19511954.
de Souza, M. L., Wackett, L. P., Boundy-Mills, K. L., Mandelbaum, R. T., and Sadowsky, M. J. 1995. Cloning, characterization, and expression of a gene region from Pseudomonas sp. strain ADP involved in the dechlorination of atrazine. J. Appl. Environ. Microbiol. 61:33733378.
de Souza, M. L., Wackett, L. P., and Sadowsky, M. J. 1998b. The atzABC genes encoding atrazine catabolism are located on a self-transmissible plasmid in Pseudomonas sp. strain ADP. J. Appl. Environ. Microbiol. 64:23232326.
Dec, J. and Bollag, J.-M. 1994. Use of plant material for the decontamination of water polluted with phenols. Biotechnol. Bioeng. 44:11321139.
Dec, J. and Bollag, J.-M. 2000. Phenoloxidase-mediated interactions of phenols and anilines with humic materials. J. Environ. Qual. 29:665676.
Dec, J. and Bollag, J.-M. 2001. Use of enzymes in bioremediation. Pages 182193 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Dixon, D. P., Cole, D. J., and Edwards, R. 1997. Characterisation of multiple glutathione transferases containing the GST I subunit with activities toward herbicide substrates in maize (Zea mays). Pestic. Sci. 50:7282.
Dixon, D. P., Cole, D. J., and Edwards, R. 1998a. Purification, regulation and cloning of a glutathione transferase (GST) from maize resembling the auxin-inducible type-III GSTs. Plant Mol. Biol. 36:7587.
Dixon, D. P., Cummins, I., Cole, D. J., and Edwards, R. 1998b. Glutathione-mediated detoxification systems in plants. Curr. Opin. Plant Biol. 1:258270.
Droog, F. 1997. Plant glutathione S-transferases, a tale of theta and tau. J. Plant Growth Regul. 16:95107.
Dudler, R., Hertig, C., Rebmann, G., Bull, J., and Mauch, F. 1991. A pathogen-induced wheat gene encodes a protein homologous to glutathione-S-transferases. Mol. Plant-Microbe Interact. 4:1418.
Durst, F. and O’Keefe, D. P. 1995. Plant cytochromes P450: an overview. Drug Metab. Drug Interact. 12:171186.
Dyer, E. and Wright, G. C. 1959. Thermal degradation of alkyl N-phenylcarbamates. J. Am. Chem. Soc. 81:21382143.
Edwards, R. and Dixon, D. P. 1991. Glutathione S-cinnamoyl transferases in plants. Phytochemistry 30:7984.
Ekler, Z., Dutka, F., and Stephenson, G. R. 1993. Safener effects on acetochlor toxicity, uptake, metabolism and glutathione S-transferase activity in maize. Weed Res. 33:311318.
Ekler, Z. and Stephenson, G. R. 1989. Physiological responses of maize and sorghum to four different safeners for metazachlor. Weed Res. 29:181191.
Engelhardt, G., Wallnofer, P. R., and Plapp, R. 1973. Purification and properties of an aryl acylamidase of Bacillus sphaericus, catalyzing the hydrolysis of various phenylamide herbicides and fungicides. Appl. Microbiol. 26:709718.
Erickson, L. E., Davis, L. C., and Narayanan, M. 1995. Bioenergetics and bioremediation of contaminated soil. Thermochim. Acta 250:353358.
Erickson, L. E. and Lee, K. H. 1989. Degradation of atrazine and related s-triazines. Crit. Rev. Environ. Control 19:114.
Ezra, G. and Gressel, J. 1982. Rapid effects of a thiocarbamate herbicide and its dichloroacetamide protectant on macromolecular syntheses and glutathione levels in maize cell cultures. Pestic. Biochem. Physiol. 17:4858.
Ezra, G., Krochmal, E., and Gressel, J. 1982. Competition between a thiocarbamate herbicide and herbicide protectants at the level of uptake into maize cells in culture. Pestic. Biochem. Physiol. 18:107112.
Fan, T. W., Lane, A. N., Pedler, J., Crowley, D., and Higashi, R. M. 1997. Comprehensive analysis of organic ligands in whole root exudates using nuclear magnetic resonance and gas chromatography-mass spectrometry. Anal. Biochem. 251:5768.
Farago, S., Kreuz, K., and Brunold, C. 1993. Decreased glutathione levels enhance the susceptibility of maize seedlings to metolachlor. Pestic. Biochem. Physiol. 47:199205.
Feng, P.C.C. 1991. Soil transformation of acetochlor via glutathione conjugation. Pestic. Biochem. Physiol. 40:136142.
Feng, P.C.C. and Ruff, T. G. 2001. A review of strategies to engineer plant tolerance to the pyridine herbicides. Pages 129144 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Feng, P.C.C. and Wratten, S. J. 1989. In vitro transformation of chloroacetanilide herbicides by rat liver enzymes: a comparative study of metolachlor and alachlor. J. Agric. Food Chem. 37:10881093.
Ferro, A., Sims, M.R.C., and Bugbee, B. 1994. Hycrest crested wheatgrass accelerates the degradation of pentachlorophenol in soil. J. Environ. Qual. 23:272279.
Feung, C., Hamilton, R. H., and Mumma, R. O. 1975. Metabolism of 2,4-dichlorophenoxyacetic acid. VII. Comparison of metabolities from five species of plant tissue cultures. J. Agric. Food Chem. 23:373376.
Feung, C., Hamilton, R. H., and Witham, F. H. 1971. Metabolism of 2,4-dichlorophenoxyacetic acid by soybean cotyledon callus tissue cultures. J. Agric. Food Chem. 19:475479.
Feung, C., Mumma, R. O., and Hamilton, R. H. 1974. Metabolism of 2,4-dichlorophenoxyacetic acid. VI. Biological properties of amino acid conjugates. J. Agric. Food Chem. 22:307309.
Field, J. A. and Thurmann, E. M. 1996. Glutathione conjugation and contaminant transformation. Environ. Sci. Technol. 30:14131418.
Flanders, C., Dec, J., and Bollag, J.- M. 1999. Horseradish-mediated binding of 2,4-dichlorophenol to soil. Bioremed. J. 3:315321.
Forlani, G., Mangiagalli, A., Nielsen, E., and Suardi, C. M. 1999. Degradation of the phosphonate herbicide glyphosate in soil: evidence for a possible involvement of unculturable microorganisms. Soil Biol. Biochem. 31:991997.
Frear, D. S. 1976. Pesticide conjugates-glycosides. Pages 3554 In Kaufman, D. D., Still, G. G., Paulson, G. D., and Bandal, S. K., eds. Bound and Conjugated Pesticide Residues. ACS Symposium Series 29. Washington, DC: American Chemical Society.
Frear, D. S., Mansager, E. R., and Swanson, H. R. 1989. Picloram metabolism in leafy spurge: isolation and identification of glucose and gentiobiose conjugates. J. Agric. Food Chem. 37:14081412.
Frear, D. S., Mansager, E. R., Swanson, H. R., and Tanaka, F. S. 1983. Metribuzin metabolism in tomato: isolation and identification of N-glucoside conjugates herbicide, residues, tolerance. Pestic. Biochem. Physiol. 19:270281.
Frear, D. S. and Still, G. G. 1968. The metabolism of 3,4-dichloropropionanilide in plants. Partial purification and properties of an aryl acylamidase from rice. Phytochemistry 7:913920.
Frear, D. S., Swanson, H. R., and Mansager, E. R. 1985. Alternate pathways of metribuzin metabolism in soybean: formation of N-glucoside and homoglutathione conjugates. Pestic. Biochem. Physiol. 23:5665.
Frear, D. S., Swanson, H. R., Mansager, E. R., and Wien, R. G. 1978. Chloramben metabolism in plants: isolation and identification of glucose ester. J. Agric. Food Chem. 26:13471351.
Frear, D. S., Swanson, H. R., and Tanaka, F. S. 1993. Metabolism of flumetsulam (DE498) in wheat, corn and barley. Pestic. Biochem. Physiol. 45:178192.
Freedman, L. D. and Doak, G. O. 1957. The preparation and properties of phosphonic acids. Chem. Rev. 57:479523.
Frenzel, P., Bosse, U., and Janssen, P. H. 1999. Rice roots and methanogenesis in a paddy soil: ferric iron as an alternative electron acceptor in the rooted soil. Soil Biol. Biochem. 31:421430.
Frey, M., Chomet, P., Glaswischnig, E. et al. 1997. Analysis of a chemical plant defense mechanism in grasses. Science 277:696699.
Frost, J. W., Loo, S., Cordeiro, M. L., and Li, D. 1987. Radical-based dephosphorylation and organophosphonate biodegradation. J. Am. Chem. Soc. 109:21662171.
Frova, C., Sari Gorla, M., Pe, M. E., Greenland, A., Jepson, I., and Rossini, L. 1997. Role of the different GST isozymes of maize in herbicide tolerance: genetics and biochemical analysis. Pages 171181 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic.
Fuenmayor, S. L., Wild, M., Boyes, A. L., and Williams, P. A. 1998. A gene cluster encoding steps in conversion of naphthalene to gentisate in Pseudomonas sp. strain U2. J. Bacteriol. 180:25222530.
Fuerst, E. P. and Gronwald, J. W. 1986. Induction of rapid metabolism of metolachlor in sorghum (Sorghum bicolor) shoots by CGA-92194 and other antidotes. Weed Sci. 34:354361.
Gaillard, C., Dufaud, A., Tommasini, R., Kreuz, K., Amhreim, N., and Martinoia, E. 1994. A herbicide antidote (safener) induces the activity of both the herbicide detoxifying enzyme and of vacuolar transporter for the detoxified herbicide. FEBS Lett. 352:219221.
Gaillardon, P., Cabanne, F., Scalla, R., and Durst, F. 1985. Effect of mixed function oxidase inhibitors on the toxicity of chlortoluron and isoproturon to wheat. Weed Res. 25:397402.
Gaynor, J. D. 1992. Microbial hydrolysis of diclofop-methyl in soil. Soil Biol. Biochem. 24:2932.
Gennari, M., Negre, M., Ambosoli, R., Andreoni, V., Vincenti, M., and Acquati, A. 1994. Anaerobic degradation of acifluorfen by different enrichment cultures. J. Agric. Food Chem. 42:12321236.
Gennari, M., Vincenti, M., Negre, M., and Ambosoli, R. 1995. Microbial metabolism of fenoxaprop-ethyl. Pestic. Sci. 44:299303.
Ghisalba, O., Kuenzi, M., Ramos Tombo, G. M., and Schar, H.- P. 1987. Microbial degradation and utilization of selected organophosphorus compounds—strategies and applications. Chimia 41:206215.
Gray, J. A., Balke, N. E., and Stoltenberg, D. E. 1996. Increased glutathione conjugation of atrazine confers resistance in a Wisconsin velvetleaf (Abutilon theophrasti) biotype. Pestic. Biochem. Physiol. 55:157167.
Griffith, G. D., Cole, J. R., Quensen, J. F. III, and Tiedje, J. M. 1992. Specific deuteration of dichlorobenzoate during reductive dehalogenation by Desulfomonile tiedjei in D2O. Appl. Environ. Microbiol. 58:409411.
Groenewegen, P.E.J., Breeuwer, P., van Helvoort, J.M.L.M., Langenhoff, A.A.M., de Vries, F. P., and de Bont, J.A. M. 1992. Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10. J. Gen. Microbiol. 138:15991605.
Groenewegen, P.E.J. and de Bont, J.A.M. 1992. Degradation of 4-nitrobenzoate via 4-hydroxylaminobenzoate and 3,4-dihydroxybenzoate in Comamonas acidovorans NBA-10. Arch. Microbiol. 158:381386.
Gronwald, J. W., Fuerst, E. P., Eberlein, C. V., and Egli, M. A. 1987. Effect of herbicide antidotes on glutathione content and glutathione S-transferase activity of sorghum shoots. Pestic. Biochem. Physiol. 29:6676.
Haby, P. A. and Crowley, D. E. 1996. Biodegradation of 3-chlorobenzoate as affected by rhizodeposition and selected carbon substrates. J. Environ. Qual. 25:304310.
Hagen, G., Uhrhammer, N., and Guilfoyle, T. J. 1988. Regulation of expression of an auxin-induced soybean sequence by cadmium. J. Biol. Chem. 263:64426446.
Häggblom, M. M. 1990. Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds. J. Basic Microbiol. 2:115141.
Häggblom, M. M., Janke, D., and Salkinoja-Salonen, M. S. 1989. Hydroxylation and dechlorination of tetrachlorohydroquinone by Rhodoccus sp. strain CP-2 cell extracts. Appl. Environ. Microbiol. 55:516519.
Haider, K., Mosier, A., and Heinemeyer, O. 1987. The effect of growing plants on denitrification at high soil nitrate concentrations. Soil. Sci. Soc. Am. J. 51:97102.
Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M. 2001a. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. Washington, DC: American Chemical Society. 432 p.
Hall, J. C., Wickenden, J. S., and Yau, K.Y.F. 2001b. Biochemical conjugation of pesticides in plants and microogranisms: an overview of similarities and divergences. Pages 89118 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. Washington, DC: American Chemical Society.
Hallas, L. E., Hahn, E. M., and Korndorfer, C. 1988. Characterization of microbial traits associated with glyphosate biodegradation in industrial activated sludge. J. Ind. Microbiol. 3:377385.
Hammond, P. M., Price, C. P., and Scaven, M. D. 1983. Purification and properties of aryl acylamidase from Pseudomonas fluorescens ATCCC 39004. Eur. J. Biochem. 132:651655.
Han, S. and Hatzios, K. K. 1991. Physiological interactions between the herbicide pretilachlor and the safener fenclorim on rice. Pestic. Biochem. Physiol. 39:270280.
Hardcastle, W. S. 1974. Differences in the tolerance of metribuzin by varieties of soybeans. Weed Res. 14:181184.
Hardcastle, W. S. 1979. Soybean (Glycine max) cultivar response to metribuzin in solution culture. Weed Sci. 27:278279.
Hartwig, E. E., Barrentine, W. L., and Edwards, J. Jr. 1980. Registration of Tracy-M soybeans. J. Crop Sci. 20:825.
Hatzios, K. K. 1991. Biotransformations of herbicides in higher plants. Pages 141185 In Grover, R. and Cessna, A. J., eds. Environmental Chemistry of Herbicides. Boca Raton, FL: CRC Press.
Hatzios, K. K. 1997. Regulation of xenobiotic degrading enzymes with herbicide safeners. Pages 275288 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic Publishers.
Hatzios, K. K. 2001. Functions and regulation of plant glutathione-S-transferases. Pages 218239 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. Washington, DC: American Chemical Society.
Hatzios, K. K. and Hoagland, R. E. 1989. Development of herbicide safeners: industrial and university perspectives. Pages 338 In Hatzios, K. K. and Hoagland, R. E., eds. Crop Safeners for Herbicides: Development, Uses, and Mechanisms of Action. San Diego, CA: Academic Press.
Hausladen, A. and Alscher, R. G. 1993. Glutathione. Pages 130 In Alscher, R. G. and Hess, J. L., eds. Antioxidants in Higher Plants. Boca Raton, FL: CRC Press.
Hershey, H. P. and Stoner, T. D. 1991. Isolation and characterization of cDNA clones for RNA species induced by substituted benzenesulfonamides in corn. Plant Mol. Biol. 17:679690.
Hirase, K. and Matsunaka, S. 1991. Purification and properties of propanil hydrolase in Pseudomonas picketti . Pestic. Biochem. Physiol. 39:302308.
Hoagland, R. E. 1975. Hydrolysis of 3’,4'-dichloropropionanilide by an aryl acylamidase from Taraxacum officinale . Phytochemistry 14:383386.
Hoagland, R. E. 1978. Isolation and some properties of an aryl acylamidase from red rice, Oryza sativa L., that metabolizes 3’,4'-dichloropropionanilide. Plant Cell Physiol. 19:10191027.
Hoagland, R. E. and Graf, G. 1972. An aryl acylamidase from tulip which hydrolyzes 3',4'-dichloropropionanilide. Phytochemistry 11:521527.
Hoagland, R. E. and Zablotowicz, R. M. 1995. Rhizobacteria with exceptionally high aryl acylamidase activity. Pestic. Biochem. Physiol. 52:190200.
Hoagland, R. E. and Zablotowicz, R. M. 1998. Biotransformations of fenoxaprop-ethyl by fluorescent Pseudomonas strains. J. Agric. Food Chem. 45:47594765.
Hoagland, R. E. and Zablotowicz, R. M. 2001. The role of plant and microbial hydrolytic enzymes in pesticide metabolism. Pages 5888 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Hoagland, R. E., Zablotowicz, R. M., and Locke, M. A. 1997. An integrated phytoremediation strategy for chloroacetamides in soil. Pages 3853 In Kruger, E. L., Anderson, T. A., and Coats, J. R., eds. Phytoremediation of Soil and Water Contaminants. ACS Symposium Series 664. Washington, DC: American Chemical Society.
Hodgson, R. H., Frear, D. S., Swanson, H. R., and Regan, L. A. 1973. Alteration of diphenamid metabolism in tomato by ozone. Weed Sci. 21:542549.
Hoffman, O. L. 1962. Chemical seed treatments as herbicidal antidotes. Weed Sci. 10:322323.
Hückelhoven, R., Schuphan, I., Thiede, B., and Schmidt, B. 1997. Biotransformation of pyrene by cell cultures of soybean (Glycine max L.), wheat (Triticum aestivum L.), jimsonweed (Datura stramonium L.), and purple foxglove (Digitalis purpurea L.). J. Agric. Food Chem. 45:263269.
Hustler, A. and Marschner, H. 1994. The influence of root exudates on the uptake of PCDD/PCDE by plants. Organohalogen Compounds 20:3134.
Incledon, B. J. and Hall, J. C. 1997. Enzymatic de-esterification of xenobiotics in plants. Pages 6782 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic Publishers.
Iwan, J. 1976. Miscellaneous conjugations—acylation and alkylation of xenobiotics in physiologically active systems. Pages 132152 In Kaufman, D. D., Still, G. G., Paulson, G. D., and Bandal, S. K., eds. Bound and Conjugated Pesticide Residues. ACS Symposium Series 29. Washington, DC: American Chemical Society.
Jepson, I., Andrews, C. J., Roussel, V., Skipsey, M., and Towson, J. K. 1999. Transgenic approaches to understanding glutathione S-transferases. Abstr. Weed Sci. Soc. Am. 39:355.
Jepson, I., Lay, V. J., Holt, D. C., Bright, S.W.J., and Greenland, A. 1994. Cloning and characterization of maize herbicide safener-induced cDNAs encoding subunits of glutathione S-transferase isoforms I, II, and IV. J. Plant Mol. Biol. 26:18551866.
Jones, A. M. 1994. Auxin-binding proteins. Annu. Rev. Plant Physiol. Plant Mol. Biol. 45:393420.
Jordahl, J. L., Foster, L., Schnoor, J. L., and Alvarez, P. J. 1997. Effect of hybrid poplar trees on microbial populations important to hazardous waste bioremediation. J. Environ. Toxicol. Chem. 16:13181321.
Joshi, D. K. and Gold, M. H. 1993. Degradation of 2,4,5-trichlorophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium . Appl. Environ. Microbiol. 59:17791785.
Kadiyala, V. and Spain, J. C. 1998. A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905. Appl. Environ. Microbiol. 64:24792484.
Kafarski, P., Lejczak, B., and Forlani, G. 2001. Biodegradation of pesticides containing carbon-to-phosphorous bond. Pages 145163 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Katayama, A. and Matsumura, F. 1993. Degradation of organochlorine pesticides, particularly endosulfan, by Trichoderma harzianum . Environ. Toxicol. Chem. 12:10591065.
Kaufman, D. D., Blake, J., and Miller, D. E. 1971. Methylcarbamates affect acylanilide herbicide residues in soil. J. Agric. Food Chem. 19:204206.
Kearney, P. C. and Kaufman, D. D. 1965. Enzyme from soil bacterium hydroylzes phenylcarbamate herbicides. Science 147:740741.
Ketchersid, M. L., Vietor, D. M., and Merkle, M. G. 1982. CGA-43089 effects on metolachlor uptake and membrane permeability in grain sorghum (Sorghum bicolor). J. Growth Regul. 1:285294.
Kim, S. K., Makino, K., Amemura, M., Shinagawa, H., and Nakata, A. 1993. Molecular analysis of the phoH gene, belonging to the phosphate regulon in Escherichia coli . J. Bacteriol. 175:13161324.
Kinouchi, T. and Ohnishi, Y. 1983. Purification and characterization of 1-nitropyrene nitroreductases from Bacteroides fragilis . Appl. Environ. Microbiol. 46:596604.
Klambt, D. H. 1961. Stoffwechselprodukte der naphthyl-1-essigsaure und 2,4-dichlorphenoxyessigsaure und der vergleich mit jenen der indol-3-essigsaure und benzoesaure. Planta 57:339353.
Köcher, H., Kellner, H. M., Lötzsch, K., Dorn, E., and Wink, O. 1982. Mode of action and metabolic fate of the herbicide fenoxaprop-ethyl, HOE 33171. Br. Crop Prot. Conf. Weeds 1:341347.
Komoβa, D., Gennity, I., and Sandermann, H. Jr. 1992. Plant metabolism of herbicides with C-P bonds: glyphosate. Pestic. Biochem. Physiol. 43:8594.
Komoβa, D. and Sandermann, H. Jr. 1992. Plant metabolism of herbicides with C-P bonds: phosphinothricin. Pestic. Biochem. Physiol. 43:95102.
Korpraditskul, R., Katayama, A., and Kuwatsuka, S. 1993. Degradation of atrazine by soil bacteria in the stationary phase. J. Pestic. Sci. 18:293298.
Kreslavski, V. D., Vasilyeva, G. K., Comfort, S. D., Drijber, R. A., and Shea, P. J. 1999. Accelerated transformation and binding of 2,4,6-trinitrotoluene in rhizosphere soil. Bioremed. J. 3:5969.
Kreuz, K., Gaudin, J., Stingelin, J., and Ebert, E. Z. 1991. Metabolism of the aryloxyphenoxypropanoate herbicide, CGA 184927, in wheat, barley and maize: differential effects of the safener CGA 185072. Z. Naturforsch. 46c:901905.
Kreuz, K., Tommasini, R., and Martinoia, E. 1996. Old enzymes for a new job: herbicide detoxification in plants. Plant Physiol. 111:349353.
Krzysko-Lupicka, T. and Orlik, A. 1997. The use of glyphosate as the sole source of phosphorus or carbon for the selection of soil-borne fungal strains capable to degrade this herbicide. Chemosphere 34:26012605.
Kullman, S. W. and Matsumura, F. 1996. Metabolic pathways utilized by Phanerochaete chrysosporium for degradation of the cyclodiene pesticide endosulfan. Appl. Environ. Microbiol. 62:593600.
Kusaba, M., Takahashi, Y., and Nagata, T. 1996. A multiple-stimuli-responsive as-1-related element of parA gene confers responsiveness to cadmium but not to copper. Plant Physiol. 111:11611167.
Lamar, R. T. and Dietrich, D. M. 1990. In situ depletion of pentachlorophenol from contaminated soil by Phanerochaete spp . Appl. Environ. Microbiol. 56:30933100.
Lamoureux, G. L. and Frear, D. S. 1979. Pesticide metabolism in higher plants: in vitro enzyme studies. Pages 77128 In Paulson, G. D., Frear, D. S., and Marks, E. P., eds. Xenobiotic Metabolism: In Vitro Methods. ACS Symposium Series 97. Washington, DC: American Chemical Soceity.
Lamoureux, G. L. and Rusness, D. G. 1980. Pentachloronitrobenzene metabolism in peanut. 1. Mass spectral characterization of seven glutathione-related conjugates produced in vivo or in vitro . J. Agric. Food Chem. 28:10571070.
Lamoureux, G. L. and Rusness, D. G. 1986. Xenobiotic conjugation in higher plants. Pages 62105 In Paulson, G. D., Caldwell, J., Hutson, D. H., and Menn, J. J., eds. Xenobiotic Conjugation Chemistry. ACS Symposium Series 97. Washington, DC: American Chemical Society.
Lamoureux, G. L. and Rusness, D. G. 1989. The role of glutathione-S-transferases in pesticide metabolism, selectivity, and mode of action in plants and insects. Pages 153196 In Dolphin, D., Polson, R., and Avramovic, O., eds. Coenezymes and Cofactors. Glutathione: Chemical, Biochemical and Medical Aspects. Volume 3. New York: Wiley.
Lamoureux, G. L. and Rusness, D. G. 1991. The effect of BAS 145138 safener on chlorimuron ethyl metabolism and toxicity in corn. Z. Naturforsch. 46c:882886.
Lamoureux, G. L. and Rusness, D. G. 1993. Glutathione in the metabolism and detoxification of xenobiotics in plants. Pages 221237 In De Kok, L. J., Stulen, I., Rennenberg, H., Brunold, C., and Rauser, W., eds. Sulfur Nutrition and Assimilation in Higher Plants. The Hague, The Netherlands: SPB Academic Publishing.
Lamoureux, G. L., Shimabukuro, R. H., and Frear, D. S. 1991. Glutathione and glucoside conjugation in herbicide selectivity. Pages 227261 In Casely, J. C., Cussans, G. W., and Atkin, R. K., eds. Herbicide Resistance in Weeds and Crops. Oxford: Butterworth-Heinemann.
Lamoureux, G. L., Simoneaux, B., and Larson, J. 1998. The metabolism of atrazine and related 2-chloro-4,6-bis(alkylamino)-s-triazines in plants. Pages 6081 In Ballantine, L. G., McFarland, J. E., and Hackett, D. S., eds. Triazine Herbicides: Risk Assessment. ACS Symposium Series 68. Washington, DC: American Chemical Society.
Lay, M. M. and Casida, J. E. 1976. Dichloroacetamide antidotes enhance thiocarbamate sulfoxide detoxification by elevating corn root glutathione content and glutathione S-transferase activity. Pestic. Biochem. Physiol. 6:442456.
Leah, J. M., Caseley, J. C., Riches, C. R., and Valverde, B. 1994. Association between elevated activity of aryl acylamidase and propanil resistance in jungle-rice Echinochloa colona . Pestic. Sci. 42:281289.
Leavitt, J.R.C. and Penner, D. 1979. In vitro conjugation of glutathione and other thiols with acetanilide herbicides and EPTC sulfoxide and the action of the herbicide antidote R-25688. J. Agric. Food Chem. 27:533536.
Leisinger, T., Bader, R., Hermann, R., Schmid-Appert, M., and Vuilleumier, S. 1994. Microbes, enzymes and genes involved in dichloromethane utilization. Biodegradation 5:237248.
Lenke, H. and Knackmuss, H. J. 1992. Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2. Appl. Environ. Microbiol. 58:29332937.
Lenke, H., Pieper, D. H., Bruhn, C., and Knackmuss, H. J. 1992. Degradation of 2,4-dinitrophenol by two Rhodococcus erythropolis strains, HL 24-1 and HL 24-2. Appl. Environ. Microbiol. 58:29282932.
Leung, K. T., Cassidy, M. B., Shaw, K. W., Lee, H., Trevors, J. T., Lohmeier-Vogel, E. L., and Vogel, H. J. 1997. Pentachlorophenol biodegradation by Pseudomonas spp. UG25 and UG30. World J. Microbiol. Biotech. 13:305313.
Li, Z.-S., Zhao, Y., and Rhea, P. A. 1995a. Magnesium adenosine 5'-triphosphate-energized transport of glutathione S-conjugates by plant vacuolar membrane vesicles. Plant Physiol. 107:12571268.
Li, Z.-S., Zhen, R.-G., and Rea, P. A. 1995b. 1-Chloro-2,4-dinitrobenzeneelicited increase in vacuolar glutathione-S-conjugate transport activity. Plant Physiol. 109:177185.
Liu, S. Y., Schocken, M. J., and Rosazza, J.P.N. 1996. Microbial transformations of clomazone. J. Agric. Food Chem. 44:313319.
Llewellyn, D. and Last, D. 1996. Genetic engineering of crops for tolerance to 2,4-D. Pages 159174 In Duke, S. O., ed. Herbicide Resistant Crops. Boca Raton, FL: CRC Press.
Locke, M. A., Gaston, L. A., and Zablotowicz, R. M. 1997. Acifluorfen sorption and sorption kinetics in soil. J. Agric. Food Chem. 45:286293.
Lovley, D. T., Coates, J. D., Blunt-Harris, E. L., Phillips, E.J.P., and Woodward, J. C. 1996. Humic substances as electron acceptors for microbial respiration. Nature 382:445448.
Low, P. S. and Merida, J. R. 1996. The oxidative burst in plant defense: function and signal transduction. Physiol. Plant. 96:533542.
Lusby, W. R., Oliver, J. E., and Kearney, P. C. 1980. Metabolism of 2,6-dinitro-4-(trifluoromethyl)benzenamine by a Streptomyces isolated from soil. J. Agric. Food Chem. 28:641644.
Macnicol, P. K. 1987. Homoglutathione and glutathione synthetases of legume seedlings: partial purification and substrate specificity. Plant Sci. 53:229235.
Malik, J., Barry, G., and Kishore, G. M. 1989. The herbicide glyphosate. Biofactors 2:1725.
Mandelbaum, R. T., Allan, D. L., and Wackett, L. P. 1995. Isolation and characterization of a Pseudomonas sp. that mineralizes the s-triazine herbicide atrazine. Appl. Environ. Microbiol. 61:14511457.
Mangeot, B. L., Slife, F. E., and Rieck, C. E. 1979. Differential metabolism of metribuzin herbicide by two soybean (Glycine max) cultivars. Weed Sci. 27:267269.
Marrs, K. A. 1996. The functions and regulation of glutathione S-transferases in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 47:127158.
Marrs, K. A., Alfenito, M. R., Lloyd, A. M., and Walbot, V. 1995. A glutathione S-transferase involved in vacuolar transfer encoded by the maize gene Bronze-2 . Nature 375:397400.
Martinez, B., Tompkins, J., Wackett, L. P., Wing, R., and Sadowsky, M. J. 2001. Complete nucleotide sequence and organization of the atrazine catabolic plasmid pADP-1 from Pseudomonas sp. strain ADP. J. Bacteriol. 183:56845697.
Martinoia, E., Grill, E., Tommasini, R., Kreuz, K., and Amhreim, N. 1993. ATP-dependent glutathione S-conjugate ‘export’ pump in the vacuolar membrane of plants. Nature 364:247249.
Matsunaka, S. 1968. Propanil hydrolysis: inhibition in rice plants by insecticides. Science 160:13601361.
McBride, K. E., Kenny, J. W., and Stalker, D. M. 1986. Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae . Appl. Environ. Microbiol. 52:325330.
McCarthy, D. L., Navarrete, S., Willett, W. S., Babbitt, P. C., and Copley, S. D. 1996. Exploration of the relationship between tetrachlorohydroquinone dehalogenase and the glutathione S-transferase superfamily. Biochemistry 35:14 63414 642.
McDaniel, C. S., Harper, L. L., and Wild, J. R. 1988. Cloning and sequencing of a plasmid-borne gene (opd) encoding a phosphotriesterase. J. Bacteriol. 170:23062311.
McGonigle, B., Lau, S.-M. C., and O’Keefe, D. P. 1997. Endogenous reactions and substrate specificity of herbicide metabolizing enzymes. Pages 918 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic Publishers.
Menendez, J. and De Prado, R. 1997. Detoxification of chlorotoluron in a chlorotoluron-resistant biotype of Alopecurus myosuroides . Comparison between cell cultures and whole plants. Physiol. Plant. 99:97104.
Metcalf, W. W. and Wanner, B. L. 1991. Involvement of the Escherichia coliphn (psiD) gene cluster I assimilation of phosphorus in the form of phosphonates, phosphite, Pi esters, and Pi . J. Bacteriol. 173:587600.
Milcamps, A. and deBruijn, F. J. 1999. Identification of a novel nutrientdeprivation-induced Sinorhizobium meliloti gene (hmgA) involved in the degradation of tyrosine. Microbiology 145:935947.
Mine, A., Miyakado, M., and Matsunaka, S. 1975. The mechanism of bentazon selectivity. Pestic. Biochem. Physiol. 5:566574.
Mochida, K., Nakamura, T., Li, W. X., and Ozoe, Y. 1993. Purification of extracellular aryl acylamidase from a coryneform bacterium, strain A-1. J. Pestic. Sci. 18:211216.
Mougin, C., Cabanne, F., Canivenc, M.-C., and Scalla, R. 1990. Hydroxylation and N-demethylation of chlorotoluron by wheat microsomal enzymes. Plant Sci. 66:195203.
Mougin, C. P., Corio-Costet, M.-F., and Werck-Reichhart, D. 2001. Plant and fungal cytochrome P-450s: their role in pesticide transformation. Pages 166182 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Mougin, C., Pericaud, C., Dubroca, J., and Asther, M. 1997. Enhanced mineralization of lindane in soils supplemented with the white rot basidiomycete Phanerochaete chrysosporium . Soil Biol. Biochem. 29:13211324.
Mougin, C., Pericaud, C., Malosse, C., Laugero, C., and Asther, M. 1996. Biotransformation of the insecticide lindane by the white rot basidiomycete Phanerochaete chrysosporium . Pestic. Sci. 47:5159.
Mulbry, W. W. and Karns, J. S. 1989. Parathion hydrolase specified by the Flavobacterium opd gene relationship between the gene and protein. J. Bacteriol. 171:67406746.
Munnecke, D. M. 1976. Enzymatic hydrolysis of organophosphate insecticides, a possible disposal method. Appl. Environ. Microbiol. 32:713.
Nagata, Y., Miyauchi, K., and Takagi, M. 1999. Complete analysis of genes and enzymes for γ-hexachlorocyclohexane degradation in Sphingomonas paucimobilis UT26. J. Ind. Microbiol. Biotechnol. 23:380390.
Nannipieri, P. and Bollag, J.-M. 1991. Use of enzymes to detoxify pesticide-contaminated soils and waters. J. Environ. Qual. 20:510517.
Nardi, S., Reniero, F., and Concheri, G. 1997. Soil organic matter mobilization by root exudates of three maize hybrids. Chemosphere 35:22372244.
Neuefeind, T., Huber, R., Dasenbrock, H., Prade, L., and Bieseler, B. 1997a. Crystal structure of herbicide-detoxifying maize glutathione S-transferase-I in complex with lactoylglutathione: evidence for an inducedfit mechanism. J. Mol. Biol. 274:446453.
Neuefeind, T., Huber, R., Knablein, J., Prade, L., Mann, K., and Bieseler, B. 1997b. Cloning, sequencing, crystallization and x-ray structure of glutathione S-transferase-III from Zea mays var. mutin: a leading enzyme in detoxification of maize herbicides. J. Mol. Biol. 274:577587.
Nichols, T. D., Wolf, D. C., Roders, H. B., Beyrouty, C. A., and Renolds, C. M. 1997. Rhizosphere microbial populations in contaminated soils. Water Air Soil Pollut. 95:165178.
Nishida, M., Harada, S., Noguchi, S., Satow, Y., Inoue, H., and Takahashi, K. 1998. Three-dimensional structure of Escherichia coli glutathione S-transferase complexed with glutathione sulfonate: catalytic roles of Cys10 and His106. J. Mol. Biol. 281:135147.
Nishino, S. F. and Spain, J. C. 1993. Degradation of nitrobenzene by a Pseudomonas pseudocaligenes . Appl. Environ. Microbiol. 59:25202525.
Nomura, N. S. and Hilton, H. W. 1977. The absorption and degradation of glyphosate in five Hawaiian sugarcane soils. Weed Res. 17:113121.
Norsworthy, J. K., Talbert, R. E., and Hoagland, R. E. 1999. Chlorophyll fluorescence evaluation of agrochemical interactions with propanil on propanil-resistant barnyardgrass (Echinochloa crus-galli). Weed Sci. 47:1319.
Obojska, A., Lejczak, B., and Kubrak, M. 1999. Degradation of phosphonates by streptomycete isolates. Appl. Microbiol. Biotechnol. 51:872876.
Oyamada, M. and Kuwatsuka, S. 1989. Reduction mechanism of the nitro group of chlornitrofen, a diphenyl ether herbicide, in flooded soils. J. Pestic. Sci. 14:321327.
Padgette, S. R., Re, D. B., Barry, G. F., Eichholtz, D. E., Delannay, X., Fuchs, R. L., Kishore, G. M., and Fraley, R. T. 1996. New weed control opportunities: development of soybeans with a Roundup Ready gene. Pages 5384 In Duke, S. O., ed. Herbicide Resistant Crops. Boca Raton, FL: CRC Press.
Pallet, K. E., Little, J. P., Sheekey, M., and Veerasekaran, P. 1998. Mode of action of isoxaflutole I. Physiological effects of metabolism and selectivity. Pestic. Biochem. Physiol. 62:113124.
Pimental, D. and Levitan, L. 1986. Pesticides: amounts applied and amounts reaching pests. Biosciences 36:8691.
Plaisance, K. L. and Gronwald, J. W. 1999. Enhanced catalytic constant for glutathione S-transferase (atrazine) activity in an atrazine-resistant Abutilon theophrasti biotype. Pestic. Biochem. Physiol. 63:3449.
Pothuluri, J. V., Hinson, J. A., and Cerniglia, C. E. 1991. Propanil: toxicological characteristics, metabolism, and biodegradation potential in soil. J. Environ. Qual. 20:330347.
Prade, L., Huber, R., and Bieseler, B. 1998. Structures of herbicides in complex with their detoxifying enzyme glutathione S-transferase—explanations for the selectivity of the enzyme in plants. Structure 6:14451452.
Preston, C., Tardif, F. J., Christopher, J. T., and Powles, S. B. 1996. Multiple resistance to dissimilar herbicide chemistries in a biotype of Lolium rigidum due to enhanced activity of several herbicide degrading enzymes. Pestic. Biochem. Physiol. 54:123134.
Probst, G. W. and Tepe, J. B. 1969. Trifluralin and related compounds. Pages 255282 In Kearney, P. C. and Kaufman, D. D., eds. Degradation of Herbicides. New York: Marcel Dekker.
Quinn, J. P., Peden, J.M.M., and Dick, R. E. 1989. Carbon-phosphorus bond cleavage by gram-positive and gram-negative soil bacteria. Appl. Microbiol. Biotechnol. 31:283287.
Ramsey, R.J.L., Mena, F. L., and Stephenson, G. R. 2001. Effects of chemical safeners on herbicide action and metabolism in plants. Pages 310332 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., ed. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Reddy, G.V.B., Joshi, D. K., and Gold, M. H. 1993. Degradation of chlorophenoxyacetic acids by the lignin-degrading fungus Dichomitus squalens . Microbiology 143:23532360.
Reilley, K. A., Banks, M. K., and Schwab, A. P. 1996. Dissipation of polycyclic aromatic hydrocarbons in the rhizosphere. J. Environ. Qual. 25:212219.
Reinemer, P., Prade, L., Hof, P. et al. 1996. Three-dimensional structure of glutathione S-transferase from Arabidopsis thaliana at 2.2 resolution: structural characterization of herbicide-conjugating plant glutathione S-transferases and a novel active site architecture. J. Mol. Biol. 255:289309.
Rennenberg, H. 1982. Glutathione metabolism and possible biological roles in higher plants. Phytochemistry 21:27712781.
Rennenberg, H. and Brunold, C. 1994. Significance of glutathione metabolism in plants under stress. Prog. Bot. 55:142156.
Rheinwald, J. G., Chakrabarty, A. M., and Gunsalus, I. C. 1973. A transmissible plasmid controlling camphor oxidation in Pseudomonas putida . Proc. Natl. Acad. Sci. USA 70:885889.
Riley, P. S. and Behal, F. J. 1971. Amino acid-naphthylamide hydrolysis by Pseudomonas aeruginosa arylamidase. J. Bacteriol. 108:809816.
Robineau, T., Batard, Y., Nedelkina, S., Cabello-Hurtado, F., LeRet, M., Sorokine, O., Didierjean, L., and Werck-Reichhart, D. 1998. The chemically inducible plant cytochrome P450 CYP76B1 actively metabolizes phenylureas and other xenobiotics. Plant Physiol. 118:10491056.
Roden, E. E. and Wetzel, R. G. 1996. Organic carbon oxidation and suppression of methane production by microbial Fe(III) oxide reduction in vegetated and unvegetated freshwater wetland sediments. Limnol. Oceanogr. 41:17331748.
Romano, M. L., Stephenson, G. R., Tal, A., and Hall, J. C. 1993. The effect of monooxygenase and glutathione S-transferase inhibitors on the metabolism of diclofop-methyl and fenoxaprop-ethyl in barley and wheat. Pestic. Biochem. Physiol. 46:181189.
Rossjohn, J., Polekhina, G., Feil, S. C., Allocati, N., Masulli, M., De Illio, C., and Parker, M. W. 1998. A mixed disulfide bond in bacterial glutathione transferase: functional and evolutionary implications. Structure 6:721734.
Rozman, K. K. and Klaassen, C. D. 1996. Absorption, distribution, and excretion of toxicants. Pages 177183 In Casarett, L. and Doull, J., eds. Toxicology: The Basic Science of Poisons. New York: McGraw-Hill Health Professions Division.
Ruepple, M. L., Brighthwell, B. B., Schaefer, J., and Marvel, J. T. 1977. Metabolism and degradation of glyphosate in soil and water. J. Agric. Food Chem. 25:517528.
Rushmore, T. H. and Pickett, C. B. 1993. Glutathione S-transferases, structure, regulation, and therapeutic implications. J. Biol. Chem. 268:11 47511 478.
Rusness, D. G. and Lamoureux, G. L. 1980. Pentachloronitrobenzene fungicide metabolism in peanut. 2. Characterization of chloroform-soluble metabolites produced in vivo. J. Agric. Food Chem. 28:10701077.
Sadowsky, M. J., Tong, Z., de Souza, M., and Wackett, L. P. 1998. AtzC is a new member of the amidohydrolase protein superfamily and is homologous to other atrazine-metabolizing enzymes. J. Bacteriol. 180:152158.
Sadowsky, M. J. and Wackett, L. P. 2001. Genetics of atrazine and s-triazine degradation by Psedomonas sp. strain ADP and other bacteria. Pages 268282 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Sanchez-Fernandez, R., Ardiles-Diaz, W., Van Montagu, M., Inze, D., and May, M. 1998. Cloning and expression analyses of AtMRP4, a novel MRP-like gene from Arabidopsis thaliana . J. Mol. Genet. 258:655662.
Sandermann, H. Jr., Arjmand, M., Gennity, I., Winkler, R., Stuble, C. B., and Aschbacher, P. W. 1990. Animal bioavailability of defined xenobiotic lignin metabolites. J. Agric. Food Chem. 38:18771880.
Sandermann, H. Jr., Haas, M., Messner, B., Pflumacher, S., Schroder, P., and Wetzel, A. 1997. The role of glucosyl and malonyl conjugation in herbicide selectivity. Pages 211231 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic Publishers.
Sandermann, H. Jr., Hertkorn, N., May, R. G., and Lange, B. M. 2001. Bound pesticidal residues in crop plants: chemistry, bioavailability, and toxicology. Pages 119128 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Sandermann, H. Jr., Scheel, D., and Trenck, T.v.d. 1983. Metabolism of environmental chemicals by plants—copolymerization into lignin. J. Appl. Polym. Sci.: Appl. Polym. Symp. 37:407420.
Sarkar, J. M., Malcolm, R. L., and Bollag, J.- M. 1988. Enzymatic coupling of 2,4-dichlorophenol to stream fulvic acid in the presence of oxidoreductases. Soil Sci. Soc. Am. J. 52:688694.
Schmidt, B. 2001. Metabolic profiling using plant cell suspension cultures. Pages 4056 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Schocken, M. J. 2001. In vitro methods in metabolism and environmental fate studies. Pages 3039 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Schocken, M. J., Mao, J., and Schabacker, D. J. 1997. Microbial transformations of the fungicide cyprodinil (CGA-219417). J. Agric. Food Chem. 45:36473651.
Schröder, P. 1997. Fate of glutathione S-conjugation in plants: degradation of gluathione moiety. Pages 233244 In Hatzios, K. K., ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer Academic Publishers.
Schwab, A. P., Banks, M. K., and Arunachalam, M. 1995. Biodegradation of polycyclic aromatic hydrocarbons in rhizosphere soil. Pages 2329 In Hinchee, R. E., Hoeppel, R. E., and Anderson, D. B., eds. Bioremediation of Recalcitrant Organics. Columbus, OH: Battelle Memorial Institute.
Shaner, D. L. and Mallipudi, M. 1991. Mechanisms of selectivity of the imidazolinone herbicides. Pages 91102 In Shaner, D. L. and O’Connor, S. L., eds. The Imidazolinone Herbicides. Boca Raton, FL: CRC Press.
Shaner, D. L. and Tecle, B. 2001. Designing herbicide tolerance based on metabolic alteration: the challenges and the future. Pages 353374 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Sharma, Y. K. and Davis, K. R. 1994. Ozone-induced expression of stressrelated genes in Arabidopsis thaliana . Plant Physiol. 105:10891096.
Shields, M. S., Reagin, M. J., Gerger, R. R., Campbell, R., and Somerville, R. 1995. TOM, a new aromatic degradative plasmid from Burkholderia (Pseudomonas) cepacia G4. Appl. Environ. Microbiol. 61:13521356.
Shimabukuro, R. H. 1985. Detoxification of herbicides. Pages 215240 In Duke, S. O., ed. Weed Physiology. Volume 2. Boca Raton, FL: CRC Press.
Shiota, N., Inui, H., and Okhawa, H. 1996. Metabolism of the herbicide chlortoluron in transgenic tobacco plants expressing the fused enzyme between rat cytochrome P4501A1 and yeast NADPH-cytochrome P450 oxidoreductase. Pestic. Biochem. Physiol. 54:190198.
Siminszky, B., Corbin, F. T., Ward, E. R., Fleischmann, T. J., and Dewey, R. E. 1999. Expression of a soybean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. Proc. Natl. Acad. Sci. USA 96:17501755.
Skidmore, M. W., Paulson, G. D., Kuiper, H. A., Ohlin, B., and Reynolds, S. 1998. Bound xenobiotic residues in food commodities of plant and animal origin. Pure Appl. Chem. 70:14231447.
Smith, A. E. and Aubin, A. J. 1990. Degradation studies with 14C-fenoxaprop in Prairie soils. Can. J. Soil Sci. 70:343350.
Smith, A. E., Phatak, S. C., and Emmatty, D. A. 1989. Metribuzin metabolism by tomato cultivars with low, medium, and high levels of tolerance to metribuzin. Pestic. Biochem. Physiol. 35:284290.
Sobera, M., Wieczorek, P., Lejczak, B., and Kafarski, P. 1997. Organophosphonate utilization by the wild-type strain Chladosporum resinae . Toxicol. Environ. Chem. 61:229235.
Sommer, A. and Böger, P. 1999. Characterization of recombinant corn glutathione S-transferase isoforms I, II, III, and IV. Pestic. Biochem. Physiol. 63:127138.
Sommer, A. and Böger, P. 2001. Enzymological studies on recombinant isoforms of glutathione s-transferase from corn. Pages 253267 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Sprankle, P., Meggitt, W. F., and Penner, D. 1975. Absorption, mobility, and microbial degradation of glyphosate in the soil. Weed Sci. 23:229234.
Stalker, D. M., Kiser, J. A., Baldwin, G., Coulombe, B., and Houck, C. M. 1996. Cotton weed control using the BXN system. Pages 93105 In Duke, S. O., ed. Herbicide Resistant Crops. Boca Raton, FL: CRC Press.
Stalker, D. M., Malyj, L. B., and McBride, K. E. 1988a. Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene. J. Biol. Chem. 263:63106314.
Stalker, D. M. and McBride, K. E. 1987. Cloning and expression in Escherichia coli of a Klebsiella ozaenae plasmid-borne gene encoding a nitrilase specific for the herbicide bromoxynil. J. Bacteriol. 169:955960.
Stalker, D. M., McBride, K. E., and Malyj, L. B. 1988b. Herbicide resistance in transgenic plants expressing a bacterial detoxification gene. Science 242:419423.
Steiert, J. G. and Crawford, R. L. 1986. Catabolism of pentachlorophenol by a Flavobacterium sp. Biochem. Biophys. Res. Commun. 141:825830.
Steinkamp, R. and Rennenberg, H. 1985. Degradation of glutathione in plant cells: evidence against the participation of a γ-glutamyltranspeptidase. Z. Naturforsch. 40c:2933.
Stephenson, G. R., Bunce, N. J., Makowski, R. I., Bergsma, M. D., and Curry, J. C. 1979. Structure-activity relationships for thiocarbamate herbicides in corn. J. Agric. Food Chem. 27:543547.
Stephenson, G. R., Bunce, N. J., Makowski, R. I., and Curry, J. C. 1978. Structure-activity relationships for S-ethyl N,N-dipropylthiocarbamate (EPTC) antidotes in corn. J. Agric. Food Chem. 26:137140.
Stephenson, G. R., Tal, A., Vincent, N. A., and Hall, J. C. 1993. Interactions of fenoxaprop-ethyl with fenchlorazole-ethyl in annual grasses. Weed Technol. 7:163168.
Still, G. G. and Mansager, E. R. 1972. Aryl hydroxylation of isopropyl-3-chlorocarbanilate by soybean plants. Phytochemistry 11:515520.
Still, G. G. and Mansager, E. R. 1973. Soybean shoot metabolism of isopropyl-3-chlorocarbanilate: ortho and para aryl hydroxylation. Pestic. Biochem. Physiol. 3:8795.
Stomp, A. M., Han, K. H., Wilbert, S., and Gordon, M. P. 1993. Genetic improvement of tree species for remediation of hazardous wastes. In Vitro Cell. Dev. Biol. Plant 29:227232.
Streber, W. R., Timmis, K. N., and Zenk, M. H. 1987. Analysis, cloning, and high-level expression of 2,4-dichlorophenoxyacetate monooxygenase gene tfdA of Alcaligenes eutrophus JMP134. J. Bacteriol. 169:29502955.
Suflita, J. M., Loll, M. J., Snipes, W. C., and Bollag, J.- M. 1981. Electron spin resonance study of free radicals generated by a soil extract. Soil Sci. 131:145150.
Suzuki, T. J. 1983. Methylation and hydroxylation of pentachlorophenol by Mycobacterium sp. isolated from soil. J. Pestic. Sci. 8:419428.
Tal, J. A., Hall, J. C., and Stephenson, G. R. 1995. Non-enzymatic conjugation of fenoxaprop-ethyl with glutathione and cysteine in several grass species. Weed Res. 35:133139.
Tal, J. A., Romano, M. L., Stephenson, G. R., Schwan, A. L., and Hall, J. C. 1993. Glutathione conjugation: a detoxification pathway for fenoxaprop-ethyl in barley, crabgrass, oat and wheat. Pestic. Biochem. Physiol. 46:190199.
Tate, R. L. and Alexander, M. 1974. Formation of dimethylamine and diethylamine in soil treated with pesticides. Soil Sci. 118:317321.
Taylor, J. L., Fritzemeier, K.-H., Häuser, I., Kombrink, E., Rohwer, F., Schröder, M., Strittmatter, G., and Hahlbrock, K. 1990. Structural analysis and activation by fungal infection of a gene encoding a pathogenesisrelated protein in potato. Mol. Plant-Microbe Interact. 3:7277.
Tebbe, C. C. and Reber, H. H. 1988. Utilization of the herbicide phosphinothricin as a nitrogen source by soil bacteria. Appl. Microbiol. Biotechnol. 29:103105.
Tecle, B., Da Cunha, A., and Shaner, D. L. 1993. Differential routes of metabolism of imidazolinones: basis for soybean (Glycine max) selectivity. Pestic. Biochem. Physiol. 46:120130.
Tenhaken, R., Levine, A., Brisson, L. F., Dixon, R. A., and Lamb, C. 1995. Function of the oxidative burst in hypersensitive disease resistance. Proc. Natl. Acad. Sci. USA 92:41584163.
Ternan, N. G., McGrath, J. W., McMullan, G., and Quinn, J. P. 1998. Review: organophosphonates: occurrence, synthesis and biodegradation by microorganisms. World J. Microbiol. Biotechnol. 14:635647.
Thiessen, E. P. 1978. Barban Plus Naphthalic Anhydride for the Selective Control of Wild Oats in Oats. . University of Guelph, Guelph, ON, Canada.
Timmerman, K. P. 1989. Molecular characterization of corn glutathione S-transferase isozymes involved in herbicide detoxification. Plant Physiol. 77:323342.
Tong, Z., Board, P. G., and Anders, M. W. 1998a. Glutathione transferase zeta catalyses the oxygenation of the carcinogen dichloroacetic acid to glyoxylic acid. Biochem. J. 371:371374.
Tong, Z., Board, P. G., and Anders, M. W. 1998b. Glutathione transferase zeta-catalyzed biotransformation of dichloroacetic acid and other alpha-haloacids. Chem. Res. Toxicol. 11:13321338.
Torstensson, N.T.L. and Aamisepp, A. 1977. Detoxification of glyphosate in soil. Weed Res. 17:209211.
Trower, M. K., Sariaslani, F. S., and Kitson, F. G. 1988. Xenobiotic oxidation by cytochrome P-450-enriched extracts of Streptomyces griseus . Biochem. Biophys. Res. Commun. 157:14171422.
Tsuchida, S. and Sato, K. 1992. Glutathione transferases and cancer. CRC Crit. Rev. Biochem. Mol. Biol. 27:337384.
Tweedy, B. G., Loeppy, C., and Ross, J. A. 1970. Metabolism of 3-(pbromophenyl)-1-methoxy-1-methylurea (metobromuron) by selected soil microorganisms. Science 168:482483.
Valli, K. and Gold, M. H. 1991. Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium . J. Bacteriol. 173:345352.
van den Brink, H.J.M., van Gorcom, R.F.M., van den Hondel, C.A.M., and Punt, P. J. 1998. Cytochrome P450 enzyme systems in fungi. Fungal Genet. Biol. 23:117.
van den Tweel, W.J.J., van der Kok, J. B., and de Bont, J.A.M. 1987. Reductive dechlorination of 2,4-dichlorobenzoate to 4-chlorobenzoate and hydrolytic dehalogenation of 4-chloro-, 4-bromo, and 4-iodobenzoate by Alcaligenes denitrificans NTB-1. Appl. Environ. Microbiol. 53:810815.
van der Krol, D., Schuphan, I., Thiede, B., and Schmidt, B. 1995. Metabolism of [ring-2,6-14C]parathion in plant cell suspension cultures of carrot (Daucus carota), purple foxglove (Digitalis purpurea), soybean, thorn apple (Datura stramonium) and wheat (Triticum aestivum). Pestic. Sci. 45:143152.
van Hylckama, J.E.T., Kingma, J., Kruizinga, W., and Janssen, D. B. 1999. Purification of a glutathione S-transferase and a glutathione conjugate-specific dehydrogenase involved in isoprene metabolism in Rhodococcus sp. strain AD45. J. Bacteriol. 181:20942101.
van Hylckama, J.E.T., Kingma, J., van den Wijngaard, A. J., and Janssen, D. B. 1998. A glutathione S-transferase with activity towards cis- 1,2-dichloroepoxyethane is involved in isoprene utilization by Rhodococcus sp. strain AD45. Appl. Environ. Microbiol. 64:28002805.
Vuilleumier, S. 2001. Bacterial glutathione S-transferases and the detoxification of xenobiotics: dehalogenation through glutathione conjugation and beyond. Pages 240252 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Vuilleumier, S., Gisi, D., Stumpp, M. T., and Leisinger, T. 1999. Bacterial dichloromethane dehalogenase: a particular brand of glutathione S-transferases. Clin. Chem. Enzymol. Commun. 8:367378.
Vuilleumier, S. and Leisinger, T. 1996. Protein engineering studies of dichloromethane dehalogenase/glutathione S-transferase from Methylophilus sp. strain DM11 Ser12 but not Tyr6 is required for enzyme activity. Eur. J. Biochem. 239:410417.
Vuilleumier, S., Sorribas, H., and Leisinger, T. 1997. Identification of a novel determinant of glutathione affinity in dichloromethane dehalogenases/glutathione S-transferases. Biochem. Biophys. Res. Commun. 238:452456.
Wackett, L. P., Wanner, B. L., Venditti, C. P., and Walsh, C. T. 1987. Involvement of the phosphate regulon and the psiD locus in carbon-phosphorus lyase activity of Escherichia coli K-12. J. Bacteriol. 169:17531756.
Walton, B. T., Hoylman, A. M., Perez, M. M., Anderson, T. A., Johnson, T. R., Guthrie, E. A., and Christman, R. F. 1994. Rhizosphere microbial communities as a plant defense against toxic substances in soils. Pages 8292 In Anderson, T. A. and Coats, J. R., eds. Bioremediation through Rhizosphere Technology. ACS Symposium Series 563. Washington, DC: American Chemical Society.
Wang, T. G. and Peverly, J. H. 1999. Iron oxidation states on root surfaces of a wetland plant (Phragmites australis). Soil Sci. Soc. Am. J. 63:247252.
Wanner, B. L. and Boline, J. A. 1990. Mapping and molecular cloning of the phn (psiD) locus for phosphonate utilization in Escherichia coli . J. Bacteriol. 172:11861196.
Wanner, B. L. and McSharry, R. 1982. Phosphate-controlled gene expression in Escherichia coli K12 using Mudl-directed lacZ fusion. J. Mol. Biol. 158:347363.
Wanner, B. L. and Metcalf, W. W. 1992. Molecular genetic studies of a 10.9-kb operon in Escherichia coli for phosphonate uptake and biodegradation. FEMS Microbiol. Lett. 100:133140.
Werwath, J., Arfmann, H.-A., Piepers, D. H., Timmis, K. H., and Wittich, R.- M. 1998. Biochemical and genetic characterization of a gentisate 1,2-dioxygenase from Sphingomonas sp. strain RW5. J. Bacteriol. 180:41714176.
Williams, P. A. and Sayers, J. R. 1994. The evolution of pathways for aromatic hydrocarbon oxidation in Pseudomonas . Biodegradation 5:195217.
Wu, J., Cramer, C. L., and Hatzios, K. K. 1999. Characterization of two cDNAs encoding glutathione S-transferases in rice and induction of their transcripts by the herbicide safener fenclorim. Physiol. Plant. 105:102108.
Yaacoby, T., Hall, J. C., and Stephenson, G. R. 1991. Influence of fenchlorazole-ethyl on the metabolism of fenoxaprop-ethyl in wheat barley and crabgrass. Pestic. Biochem. Physiol. 41:296304.
Yee, D. C., Maynard, J. A., and Wood, T. K. 1998. Rhizoremediation of trichloroethylene by a recombinant, root-colonizing Pseudomonas fluorescens strain expressing toluene ortho-monooxygenase constitutively. Appl. Environ. Microbiol. 64:112118.
Yenne, S. P. and Hatzios, K. K. 1990. Molecular comparisons of selected herbicides and their safeners by computer-aided molecular modeling. J. Agric. Food Chem. 38:19501956.
Yenne, S. P., Hatzios, K. K., and Meredith, S. A. 1990. Uptake, translocation, and metabolism of oxabetrinil and CGA-133205 in grain sorghum (Sorghum bicolor) and their influence on metolachlor metabolism. J. Agric. Food Chem. 38:19571961.
Yoshioka, H., Nagasawa, T., and Yamada, H. 1991. Purification and characterization of aryl acylamidase from Nocardia globerula . Eur. J. Biochem. 199:1724.
Zablotowicz, R. M., Hoagland, R. E., Lee, H., Alber, T., Trevors, J. T., Hall, J. C., and Locke, M. A. 2001. Transformation of nitroaromatic pesticides and related xenobiotics by microorganisms and plants. Pages 194216 In Hall, J. C., Hoagland, R. E., and Zablotowicz, R. M., eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, DC: American Chemical Society.
Zablotowicz, R. M., Hoagland, R. E., and Locke, M. A. 1994. Glutathione S-transferase activity in rhizosphere bacteria and the potential for herbicide detoxification. Pages 184198 In Anderson, T. A. and Coats, J. R., eds. Bioremediation through Rhizosphere Technology. ACS Symposium Series 563. Washington, DC: American Chemical Society.
Zablotowicz, R. M., Hoagland, R. E., Locke, M. A., and Hickey, W. J. 1995. Glutathione-S-transferase activity and metabolism of glutathione conjugates by rhizosphere bacteria. Appl. Environ. Microbiol. 61:10541060.
Zablotowicz, R. M., Hoagland, R. E., Staddon, W. J., and Locke, M. A. 2000. Effects of pH on chemical stability and de-esterification of fenoxaprop-ethyl by purified enzymes, bacterial extracts, and soils. J. Agric. Food Chem. 48:47114716.
Zablotowicz, R. M., Leung, K. T., Alber, T., Cassidy, M. B., Trevors, J. T., Lee, H., Veldhuis, L., and Hall, J. C. 1999. Degradation of 2,4-dinitrophenol and selected nitroaromatic compounds by Sphingomonas sp. UG30. Can. J. Microbiol. 45:840848.
Zablotowicz, R. M., Locke, M. A., and Hoagland, R. E. 1997. Aromatic nitroreduction of acifluorfen in soils, rhizospheres, and pure cultures of rhizobacteria. Pages 3853 In Kruger, E. L., Anderson, T. A., and Coats, J. R., eds. Phytoremediation of Soil and Water Contaminants. ACS Symposium Series 664. Washington, DC: American Chemical Society.
Zajc, A., Neuefeind, T., Prade, L., Reinemer, P., Huber, R., and Bieseler, B. 1999. Herbicide detoxification by glutathione S-transferases as implicated from X-ray structures. Pestic. Sci. 55:248252.
Zama, P. and Hatzios, K. K. 1986. Effects of CGA-92194 on the chemical reactivity of metolachlor with glutathione and metabolism of metolachlor in grain sorghum (Sorghum bicolour). Weed Sci. 34:834841.
Zaranyika, M. F. and Nyandoro, M. G. 1993. Degradation of glyphosate in the aquatic environment: an enzymatic kinetic model that takes into account microbial degradation of both free and colloidal (or sediment) particle adsorbed glyphosate. J. Agric. Food Chem. 41:838842.
Zboinska, E., Maliszewska, I., Lejczak, B., and Kafarski, P. 1992. Degradation of organophosphonates by Penicillium citrinum . Lett. Appl. Microbiol. 15:269272.