@article{moreland_1999, title={Biochemical mechanisms of action of herbicides and the impact of biotechnology on the development of herbicides}, volume={24}, DOI={10.1584/jpestics.24.299}, number={3}, journal={Journal of Pesticide Science (International Ed.)}, author={Moreland, D. E.}, year={1999}, pages={299–307} }
 @article{moreland_fleischmann_corbin_mcfarland_1996, title={Differential metabolism of the sulfonylurea herbicide prosulfuron (CGA-152005) by plant microsomes}, volume={51}, DOI={10.1515/znc-1996-9-1015}, abstractNote={Microsomes isolated from excised shoots of 3-day-old. dark grown, grain sorghum [Sorghum bicolor (L.) Moench, Funk G522DR and DK 41Y] and corn seedlings [Zea mays (L.), Pioneer 3245] metabolized the sulfonylurea herbicide prosulfuron (CGA-152005). Corn microsomes predominantly formed a single major metabolite that resulted from hydroxylation of the phenyl ring at the C5 position. However, sorghum microsomes formed two major metabolites in an approximate 1:1 ratio. One was the 5-hydroxyphenyl metabolite, whereas the second metabolite resulted from ö-demethylation at C4 of the triazine ring. Metabolite identity was established by mass spectrometry and co-chromatography with authentic standards. Metabolism in both corn and sorghum was greatly enhanced by pretreatment of the seed with naphthalic anhydride and by subirrigation with 2.5% ethanol 24 h prior to harvest. Metabolism required a reduced pyridine nucleotide and was affected by several cytochrome P450 monooxygenase inhibitors (carbon monoxide, tetcyclacis, piperonyl butoxide, 1 aminobenzotriazole, and SKF-525A). The inhibitors differentially affected metabolism of prosulfuron. Microsomal oxidations from both untreated and inducer-treated tissue responded similarly to the inhibitors. In exploratory studies, microsomes isolated from shoots of wheat [Triticum aestivum L., Pioneer 2548], barley [Hordeum vulgare L., Boone], oats [Avena sativa L., Southern States 76-30-P242] and rice [Oryza sativa L„ Gulfmont], and room ripened avocado [Persea americana, Mill., Hass] mesocarp tissue also primarily formed the 5-hydroxyphenyl metabolite. Titration of seven different avocado microsomal preparations with prosulfuron provided typical type I difference spectra from which an average binding constant (Ks) of 187 ± 35 μm was obtained}, number={9}, journal={Zeitschrift fur Naturforschung. C, Biosciences}, author={Moreland, D. E. and Fleischmann, T. J. and Corbin, F. T. and McFarland, J. E.}, year={1996}, pages={698} }
 @article{moreland_corbin_fleischmann_mcfarland_1995, title={PARTIAL CHARACTERIZATION OF MICROSOMES ISOLATED FROM MUNG BEAN COTYLEDONS}, volume={52}, ISSN={["0048-3575"]}, DOI={10.1006/pest.1995.1034}, abstractNote={Abstract Microsomes isolated from excised cotyledons of 3-day-old, dark-grown, mung bean ( Vigna radiata , L., cv Berken) seedlings metabolized two endogenous substrates (cinnamic acid and lauric acid), three organophosphate insecticides (diazinon, isazofos, and methidathion), three acetamide herbicides (metolachlor, CGA-24704, and alachlor), and bentazon. Cinnamic acid was aryl hydroxylated forming p -coumaric acid. Lauric acid was primarily hydroxylated at the terminal carbon (ω-hydroxylation). The three α-chloroacetamides were O-demethylated. With all three organophosphate insecticides, the phosphorothionate sulfur was oxidized to the corresponding oxon and the phosphoroester oxygen was cleaved in both diazinon and isazofos. Bentazon was aryl hydroxylated forming the 6-hydroxy derivative. The concentration of cytochrome P450 in the microsomal preparations was marginally enhanced by pretreatment of the seed with naphthalic anhydride (NA), but was markedly increased by subirrigation of NA-treated seed with ethanol and was additionally increased with the combination of NA, clofibrate, and ethanol. The extent of metabolism of only lauric acid paralleled the increases in cytochrome P450 content. The various seed/seedling treatments, however, did approximately double the rate of metabolism of the three organophosphates, the three chloroacetamides, and bentazon. Metabolism required a reduced pyridine nucleotide and was affected by several cytochrome P450 monooxygenase inhibitors (carbon monoxide, tetcyclacis, piperonyl butoxide, 1-aminobenzotriazole, and SKF-525A). The inhibitors differentially affected metabolism of the substrates. Microsomal oxidations from both untreated and inducer-treated tissue responded similarly to the inhibitors. The differential inhibitory responses suggest that metabolism may involve several monooxygenase isoforms.}, number={2}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={MORELAND, DE and CORBIN, FT and FLEISCHMANN, TJ and MCFARLAND, JE}, year={1995}, month={Jun}, pages={98–108} }
 @article{moreland_corbin_mcfarland_1993, title={EFFECTS OF SAFENERS ON THE OXIDATION OF MULTIPLE SUBSTRATES BY GRAIN-SORGHUM MICROSOMES}, volume={45}, ISSN={["0048-3575"]}, DOI={10.1006/pest.1993.1006}, abstractNote={Abstract Microsomes isolated from excised shoots of 3-day-old, dark-grown, grain sorghum [ Sorghum bicolor (L.) Moench. Funk G522DR, and DK 41Y] seedlings metabolized cinnamic acid, lauric acid, metolachlor, bentazon, and diazinon. but did not metabolize triasulfuron or primisulfuron. Pretreatment of G522DR seed with safeners (naphthalic anhydride, dichlormid, flurazole, BAS 145138, oxabetrinil, fluxofenim, and benoxacor) resulted in enhanced metabolism of lauric acid, bentazon, and diazinon. However, metabolism of cinnamic acid was not affected and that of metolachlor was depressed by safener treatments. Microsomes isolated from DK 41Y seedlings had higher endogenous levels of oxidative activity for lauric acid and bentazon than microsomes isolated from G522DR seedlings. Metabolism required NADPH and was affected by CO and other cytochrome P450 monooxygenase inhibitors (tetcyclacis, piperonyl butoxide, 1-aminobenzotriazole, SKF-525A, and tridiphane). The inhibitors differentially affected metabolism of the substrates. Only tetcyclacis strongly inhibited the metabolism of all substrates except cinnamic acid. Microsomal oxidations from both unsafened and safener-treated tissue responded similarly to the inhibitors. The differential inhibitory responses suggest that each substrate was probably metabolized by a different monooxygenase isoform.}, number={1}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={MORELAND, DE and CORBIN, FT and MCFARLAND, JE}, year={1993}, month={Jan}, pages={43–53} }
 @article{moreland_1993, title={Research on biochemistry of herbicides: An historical overview}, volume={48}, DOI={10.1515/znc-1993-3-402}, abstractNote={Abstract}, number={3-4}, journal={Zeitschrift fur Naturforschung. C, Biosciences}, author={Moreland, D. E.}, year={1993}, pages={121} }
 @article{moreland_corbin_1991, title={Influence of safeners on the in vivo and in vitro metabolism of bentazon and metolachlor by grain sorghum shoots: A preliminary report}, volume={46}, DOI={10.1515/znc-1991-9-1031}, abstractNote={Abstract}, number={9-10}, journal={Zeitschrift fur Naturforschung. C, Biosciences}, author={Moreland, D. E. and Corbin, F. T.}, year={1991}, pages={906} }
 @article{moreland_corbin_novitzky_parker_tomer_1990, title={Metabolism of metolachlor by a microsomal fraction isolated from grain sorghum (Sorghum bicolor) shoots}, volume={45}, DOI={10.1515/znc-1990-0544}, abstractNote={A microsomal fraction isolated from the shoots of 3- to 4-day-old, dark-grown, grain sorghum (Sorghum bicolor cv. Funk G 522 D R ) seedlings was characterized. The preparations had a cytochrome P-450 content that varied from approximately 90 to 150 pmol P-450/mg protein with cytochrome P-420 varying from 0 to 3% of the P-450 content. Type I difference spectra were formed with cinnamic acid and metolachlor, and a type II spectrum was formed with tetcyclacis. In short-term assays with [14C]metolachlor as substrate, the preparations produced a single time-dependent product that separated on silica gel TLC plates developed in benzene/acetone (2:1, v/v). RF values for metolachlor and the metabolite were approximately 0.70 and 0.48, respectively. The microsomal reaction required N A D P H and oxygen, and was inhibited by carbon monoxide, with the inhibition being partially reversed by actinic light. Compounds known to inhibit the activity of cytochrome P-450 monooxygenases (piperonyl butoxide, tetcyclacis, and tridiphane) also prevented formation of the metabolite. Identity of the metabolite was confirmed by TLC and positive ion thermospray LC/MS to be 2-chloro-N-(2-ethyl-6- methylphenyl)-N-(2-hydroxy-l-methylethyl)acetamide. Hence, the reaction catalyzed by the sorghum microsomes involved O-demethylation of the methoxypropyl side chain of metolachlor.}, number={5}, journal={Zeitschrift fur Naturforschung. C, Biosciences}, author={Moreland, D. E. and Corbin, F. T. and Novitzky, W. P. and Parker, C. E. and Tomer, K. B.}, year={1990}, pages={558} }
 @article{moreland_novitzky_levi_1989, title={SELECTIVE-INHIBITION OF CYTOCHROME-P450 ISOZYMES BY THE HERBICIDE SYNERGIST TRIDIPHANE}, volume={35}, ISSN={["0048-3575"]}, DOI={10.1016/0048-3575(89)90101-6}, abstractNote={Tridiphane [2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane] cross-reacts as a synergist to both herbicides and insecticides. As reported herein, tridiphane inhibited the monooxygenase activity of one or more mouse hepatic cytochrome P450 isozymes. With hepatic microsomes isolated from mice pretreated with phenobarbitol (PB) as well as with purified P450 enzymes, tridiphane efficiently inhibited demethylase and deethylase activities catalyzed by PB-induced P450 enzymes, i.e., I50 values of approximately 4.0 μM. However, tridiphane was a weak inhibitor of enzyme activities catalyzed by hepatic microsomes isolated from 3-methylcholanthrene (3-MC)-pretreated mice. Type I binding spectra were obtained with hepatic microsomes isolated from uninduced mice (Ks = 12.6 μM) and PB-induced mice (Ks = 1.0 μM), and with a purified enzyme isolated from PB-induced mice (Ks = 0.12 μM). However, tridiphane did not form difference spectra with microsomes isolated from 3-MC-treated mice or with a purified P450 enzyme isolated from 3-MC-treated mice. Inhibition of p-nitroanisole O-demethylase suggested that tridiphane acted as a competitive inhibitor of enzyme activity and produced a Km of 440 μM with a Ki between 0.72 and 1.04 μM.}, number={1}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={MORELAND, DE and NOVITZKY, WP and LEVI, PE}, year={1989}, month={Sep}, pages={42–49} }
 @article{moreland_novitzky_1988, title={EFFECTS OF INHIBITORS AND HERBICIDES ON THE MEMBRANE-POTENTIAL OF MUNG BEAN MITOCHONDRIA}, volume={31}, ISSN={["0048-3575"]}, DOI={10.1016/0048-3575(88)90130-7}, abstractNote={Alterations imposed by herbicides on the membrane potential (Δψ), oxygen utilization, and ATP synthesis of intact mung bean mitochondria were measured under state 3 conditions. Effects were correlated with changes imposed by classical electron transport inhibitors, energy transfer inhibitors, and uncouplers. In the dose-response studies, complete inhibition of ATP synthesis produced by electron transport inhibitors (rotenone, antimycin A, KCN), uncouplers [bis(hexafluoroacetonyl)acetone (1799) and carbonyl cyanide 4-trifluoromethoxyphenylhydrazone (FCCP)], and the herbicides was associated with a decrease in Δψ from the state 3 value of 126 mV to between 90 and 100 mV. In contrast, the complete inhibition of phosphorylation produced by the energy transfer inhibitor N,N′-dicyclohexylcarbodimide correlated with an increase in Δψ from the state 3 to the state 4 potential (145 mV). In the titrations, the herbicides and classical uncouplers, but not the electron transport inhibitors, progressively collapsed Δψ below the potential associated with the complete inhibition of phosphorylation (to the apparent Donnan potential of 60 mV). The herbicides could be placed into two groups according to the dose-response relationships exhibited with respect to Δψ and oxygen utilization. The first group, designated as dinoseb types (dinitrophenols, benzimidazoles, benzonitriles, thiadiazoles, and bromofenoxim), uncoupled phosphorylation and collapsed Δψ to the Donnan level before oxygen utilization was inhibited. These compounds possess dissociable protons and are postulated to act as protonophores, much like 1799 and FCCP. With the second group, termed dicryl types (acylanilides, dinitroanilines, diphenylethers, bis-carbamates, and perfluidone), collapse of Δψ was paralleled by uncoupling of phosphorylation and inhibition of oxygen utilization. However, phosphorylation was inhibited to a greater extent than was respiration. The dicryl-type herbicides are not classical-type protonophores. Some of their action can be attributed to interference with the redox pumps. The complete collapse of Δψ to the Donnan potential is associated with alterations and perturbations induced in the membranes by classical uncouplers and by both types of herbicides. The perturbations are postulated to increase the permeability of the membranes to protons and other cations and to induce unfavorable conformational changes that impede interactions between redox enzymes. Conceivably, the combined responses collapse Δψ and inhibit electron transport.}, number={3}, journal={PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY}, author={MORELAND, DE and NOVITZKY, WP}, year={1988}, month={Jul}, pages={247–260} }
 @article{moreland_novitzky_1988, title={INTERFERENCE BY FLAVONE AND FLAVONOLS WITH CHLOROPLAST-MEDIATED ELECTRON-TRANSPORT AND PHOSPHORYLATION}, volume={27}, ISSN={["0031-9422"]}, DOI={10.1016/0031-9422(88)80732-5}, abstractNote={Abstract The effects of flavone and seven flavonols on the light-induced electron transport and phosphorylation of isolated spinach ( Spinacia oleracea L.) chloroplasts were investigated. With the exception of flavonol (3-hydroxyflavone), all of the compounds interacted with components of both the ATP-generating and electron transport pathways. Flavonol only interacted with the phosphorylation pathway. Interference with the phosphorylation pathway was evidenced by the greater sensitivity of the phosphorylation reaction than coupled whole-chain electron transport, inhibition of cyclic phosphorylation, inhibition of the light-activated Mg 2+ -ATPase, and inhibition of the heat-activated Ca 2+ -ATPase associated with CF 1 . The overall decreasing order of effectiveness for inhibition of cyclic phosphorylation was: galangin > quercetin = kaempferol = myricetin = flavonol > fisetin > flavone > morin. On the electron transport pathway, all of the compounds, except flavonol, interacted with the Q B -protein complex as, evidenced by inhibition of uncoupled electron transport, alteration of chlorophyll fluorescence transients, and competitive displacement of previously bound radiolabeled atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)- s -triazine]. The decreasing order of effectiveness for inhibition of uncoupled electron transport was: fisetin > quercetir = galangin > kaempferol > flavone > morin.}, number={11}, journal={PHYTOCHEMISTRY}, author={MORELAND, DE and NOVITZKY, WP}, year={1988}, pages={3359–3366} }
 @article{moreland_novitzky_1987, title={Interference by herbicides with the transmembrane potential of thylakoids}, volume={42}, DOI={10.1515/znc-1987-0612}, abstractNote={Interferences expressed by herbicides classified as inhibitory uncouplers were measured on the induction and maintenance of ΔpH and ΔΨ, the chemical and electrical components, respectively. of the proton motive force (pmf) generated by light-induced cyclic electron transport in spinach thylakoids. Maintenance of the pmf is required for the synthesis of ATP. The inhibitory uncouplers arc known to inhibit photophosphorylation, but the mechanisms involved remain to be identified. The dinoseb types (dinitrophenols. benzimidazoles. benzonitriles. bromophenoxim. perfluidone. thiadiazoles) of inhibitory uncouplers, most of which contain dissociable protons, were found to discharge ΔpΗ at low concentrations and to collapse ΔΨ at high concentrations. Collapse of ΔpΗ can be attributed to the protonophoric (proton shuttling) action of the herbicides. However, collapse of ΔΨ can be caused by alterations induced to the integrity and loss of semipermeability of the thylakoid membrane. As a result the membrane bccomes permeable to protons and other cations, and the electrical charges across the membrane are neutralized. The non-ionic dicryl types of inhibitory uncouplers (acylanilides. dinitroanilines. diphenylethcrs. bis-carbamates) collapsed ΔΨ at concentrations that were somewhat lower than those required for the collapse of ΔpΗ. These herbicides appear only to alter the integrity and permeability of the thylakoid membrane. Inhibition of photophosphorylation by the inhibitory uncouplcrs correlated with their ability to dissipate the pmf. }, number={6}, journal={Zeitschrift fur Naturforschung. C, Biosciences}, author={Moreland, D. E. and Novitzky, W. P.}, year={1987}, pages={718} }
 @misc{moreland_1980, title={MECHANISMS OF ACTION OF HERBICIDES}, volume={31}, ISSN={["1040-2519"]}, DOI={10.1146/annurev.pp.31.060180.003121}, journal={ANNUAL REVIEW OF PLANT PHYSIOLOGY AND PLANT MOLECULAR BIOLOGY}, author={MORELAND, DE}, year={1980}, pages={597–638} }
 @article{moreland_hussey_shriner_farmer_1974, title={ADENOSINE PHOSPHATES IN GERMINATING RADISH (RAPHANUS-SATIVUS L) SEEDS}, volume={54}, ISSN={["0032-0889"]}, DOI={10.1104/pp.54.4.560}, abstractNote={Changes in concentrations of adenosine phosphates (AMP, ADP, and ATP), oxygen utilization, and fresh weights were measured during the first 48 hours after imbibition of water by quiescent radish seeds (Raphanus sativus L.) at 22.5 C. The changes in ATP concentrations, oxygen utilization, and fresh weights followed a triphasic time course, characterized by a rapid initial increase, which extended from 0 to approximately 1.5 hours, a lag phase from 1.5 to 16 hours, and a sharp linear increase from 16 to 48 hours. In unimbibed seeds, the concentrations of ATP, ADP, and AMP were <0.1, 0.9, and 2.2 nmoles/seed, respectively. After imbibition of water by the quiescent seeds, for 1 hour, the ATP concentration had increased to 2.5, and ADP and AMP concentrations had decreased to 0.3 and 0.1 nmole/seed, respectively. These early changes occurred also in seeds maintained under anaerobic conditions (argon), or when treated with either 5 mm fluoroacetate, or 5 mm iodoacetate. The concentrations of ADP and AMP did not change significantly from 1 to 48 hours. The termination of the lag phase at 16 hours correlated with radicle emergence. Cell division in the radicles was initiated at approximately 28 hours. ATP concentrations in seeds maintained under argon or treated with fluoroacetate remained relatively constant from approximately 2 to 48 hours. In contrast, the ATP concentration of iodoacetate-treated seeds decreased curvilinearly from 4 to 48 hours. Oxidative phosphorylation was estimated to have contributed 15, 20, and 65% of the pool ATP at 1.5, 16, and 48 hours, respectively.}, number={4}, journal={PLANT PHYSIOLOGY}, author={MORELAND, DE and HUSSEY, GG and SHRINER, CR and FARMER, FS}, year={1974}, pages={560–563} }