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Invasive watermilfoils, specifically Eurasian watermilfoil and the interspecific hybrid of Eurasian watermilfoil × northern watermilfoil, continue to be problematic for water resource managers. Herbicides are often used to control these nuisance weeds and have been historically successful in controlling Eurasian watermilfoil. A population of hybrid watermilfoil from Townline Lake in Michigan has shown increased tolerance to the herbicide fluridone. The objective of this work is to determine if cross- and multiple tolerance have also developed in this population. Eurasian watermilfoil plants collected from multiple sites and plants from Townline Lake were treated with 0, 5, 10, 20, 40, or 80 µg L−1of fluridone, norflurazon, or topramezone. Fluridone and norflurazon inhibit phytoene desaturase, whereas topramezone is a 4-hydroxyphenylpyruvate dioxygenase-inhibiting herbicide. Chlorophyll fluorescence (Fv/Fm) and pigment content was measured at 10 d after treatment. Townline Lake plants responded differently from susceptible plants when treated with fluridone, norflurazon, and topramezone at 40 µg L−1. These results indicate that the Townline population of hybrid watermilfoil has inherent tolerance to multiple herbicide modes of action. These results are especially significant as topramezone has recently been labeled for aquatic use. Screening of additional herbicides to determine potential herbicide tolerance of the Townline Lake population is recommended.

Florida hydrilla populations have shown an alarming increase in resistance to fluridone, an herbicide used extensively for controlling invasive US hydrilla populations. A rapid PCR and sequencing method was developed to identify and screen hydrilla genomic DNA for three previously identified phytoene desaturase (pds) gene mutations that confer resistance to fluridone. Ninety hydrilla accessions were screened for fluridone resistant genotypes including 46 accessions from the US and 44 accessions from 15 other countries. In Florida, hydrilla from five of nine sites tested was heterozygous for wild-type and herbicide-resistant alleles. Additionally, a new resistant population was identified from Lake Seminole in Georgia, the first genetically confirmed strain of resistant hydrilla outside of Florida. All resistance-conferring mutations were located on the same homologous haplotype of US dioecious hydrilla. All other hydrilla samples tested possessed only wild type alleles, including monoecious strains that had been exposed to fluridone. Management implications are discussed.

The development of fluridone resistance by hydrilla has significantly impacted hydrilla management, and research is ongoing to develop alternate herbicides for effective hydrilla control. We determined the potential cross-resistance in fluridone-resistant hydrilla to other bleaching herbicides norflurazon, mesotrione, and topramezone-methyl. Phytoene, β-carotene, and chlorophyll contents as a function of hydrilla biotype and herbicide treatment were evaluated. Hydrilla shoot tips were collected from fluridone-susceptible (S) and -resistant (R) biotypes and exposed to 5, 25, 50, 75, and 100 µg L−1of herbicide. The susceptible biotype showed an increase in phytoene and a decrease in β-carotene and chlorophyll contents when treated with 5 µg L−1fluridone, whereas higher doses of fluridone were required to affect these pigments in the resistant biotype. There was no difference in response by S and R biotypes to mesotrione and topramezone-methyl, with both biotypes showing significant affects on pigment contents at 5 µg L−1. Higher doses of norflurazon were required to affect these pigments in the R compared to the S biotype. The S biotype had EC50values of 11.7, 12.2, and 4.7 µg L−1, whereas the R biotype had EC50values of 56.6, 41.1, and 41.7 µg L−1fluridone for phytoene, β-carotene, and chlorophyll contents, respectively. There was no difference in EC50for phytoene, β-carotene, and chlorophyll values between the hydrilla biotypes for mesotrione and topramezone-methyl herbicides. In fluridone-susceptible and -resistant hydrilla biotypes, EC50values for phytoene, β-carotene, and chlorophyll were 12.4 to 11.8, 10.2 to 13.2, and 3.1 to 4.6 µg L−1mesotrione and 12.6 to 13.5, 13.3 to 11.9, and 4.6 to 5.7 µg L−1topramezone-methyl, respectively. For norflurazon, S and R biotypes had EC50values of 33.1, 45.4, and 40.6 µg L−1and 84.6, 81.0, and 92.7 µg L−1for phytoene, β-carotene, and chlorophyll, respectively. These studies confirmed negative cross-resistance of fluridone-resistant hydrilla to mesotrione and topramezone-methyl and a positive cross-resistance to norflurazon.

Hydrilla is one of the most serious aquatic weed problems in the United States, and fluridone is the United States Environment Protection Agency (USEPA)-approved herbicide that provides relatively long-term systemic control. Mature (6-wk-old) and young (freshly planted from 10-cm apical shoot apices) hydrilla were grown in 540 L fiberglass vaults under short- (natural 8 to 10 hr light/14 to 16 hr dark photoperiod) or long- (artificially extended 16 h light/8 h dark photoperiod) day greenhouse conditions. Fluridone treatments of 0, 1, 5, and 10 µg L−1 were applied after 2 wk and maintained within each population and photoperiodic regime throughout the study. Short days promoted subterranean turion formation, but this effect was reduced by long days and 5 and 10 µg L−1 fluridone. Fluridone caused a reduction in chlorophyll and carotenoid levels but the effect on anthocyanin content was variable. Short days caused elevated anthocyanin, and this effect was diminished by fluridone. Fluridone reduced t...

Hydrilla is one of the most serious aquatic weed problems in the United States, and fluridone is the only U.S. Environment Protection Agency (USEPA)–approved herbicide that provides relatively long-term systemic control. Recently, hydrilla biotypes with varying levels of fluridone resistance have been documented in Florida. Fluridone-susceptible (S) and several fluridone-resistant (R1 to R5) hydrilla biotypes varying in resistance levels were maintained in 950-L tanks under ambient sunlight and day-length conditions. To correlate varying levels of fluridone resistance to ploidy in hydrilla, flow cytometric analysis was performed. Differential ploidy levels (diploid, 2n = 2x = 16; triploid, 2n = 3x = 24; and tetraploid, 2n = 4x = 32) were reported among different hydrilla biotypes, plants within each biotype, and within shoot tissues of the same plant. Triploid plants were predominant in all biotypes. Diploid plants were observed in all hydrilla biotypes except the susceptible hydrilla (S). Plants with tetraploidy were rare within biotypes. The diploid, triploid, and tetraploid plants had nuclear DNA contents of 2.43 to 2.73 pg, 3.44 to 3.71 pg, and 4.64 to 4.90 pg, respectively, and no differences were observed among plants with same ploidy for nuclear DNA content in different hydrilla biotypes. Endoreduplication patterns were observed in diploid plants of R1 and R3 biotypes. However, no plant with higher ploidy levels (triploid or tetraploid) in any hydrilla biotypes showed endoreduplication.

Hydrilla is one of the most serious aquatic weed problems in the United States, and fluridone is the only U.S. Environment Protection Agency (USEPA)–approved herbicide that provides relatively long-term systemic control. Recently, hydrilla biotypes with varying levels of fluridone resistance have been documented in Florida. One susceptible and five fluridone-resistant biotypes of hydrilla varying in resistance levels were maintained in 950-L tanks under ambient sunlight and day-length conditions from September 2004 to September 2005 in absence of fluridone. Because fluridone is an inhibitor of the enzyme phytoene desaturase (PDS), the gene for PDS (pds) was cloned from fluridone-susceptible and -resistant hydrilla biotypes. Somatic mutations in amino acid 304 of hydrilla PDS are known to confer herbicide resistance. We determinedpdssequence from these hydrilla biotypes at planting and 12-mo after planting. Two independent mutations at the arginine 304 codon ofpdswere found in the resistant hydrilla plants. The codon usage for arginine 304 is CGT, and a single point mutation yielding either serine (AGT) or histidine (CAT) was identified in different resistant hydrilla biotypes. There were no differences at codon 304 in the PDS protein of any hydrilla biotype 12-mo after planting. Several other mutations were also found in resistantpdsalleles, though their possible role in herbicide resistance is unclear.

Hydrilla is one of the most serious aquatic weed problems in the United States, and fluridone is the only U.S. Environment Protection Agency (USEPA)–approved herbicide that provides relatively long-term systemic control. Recently, hydrilla biotypes with varying levels of fluridone resistance have been documented in Florida. Several biotypes of hydrilla varying in resistance levels were maintained in 950-L tanks under ambient sunlight and day-length conditions from September 2004 to September 2005 in absence of fluridone. Phenotypic measurements were performed during this 1-yr period to monitor differences in growth and reproductive physiology. All fluridone-resistant biotypes (except R3) were growing at the same rate or greater than the susceptible hydrilla. These data suggested that there are no deleterious effects on growth and reproductive physiology because of development of fluridone resistance. Aggressive spread of fluridone-resistant dioecious hydrilla in aquatic ecosystems can severely affect hydrilla management and, consequently, cause substantial and long-lasting ecological and economic problems throughout the southern United States.

Hydrilla is one of the most serious aquatic weed problems in the United States, and fluridone is the only herbicide approved by the U.S. Environment Protection Agency that provides systemic control. Recently, hydrilla biotypes with varying levels of fluridone resistance have been documented in Florida. Hydrilla biotypes of varying fluridone resistance levels were maintained in 900-L tanks under natural atmospheric conditions from September 2004 to September 2005 in the absence of fluridone. Hydrilla shoot tips were collected from each biotype during September 2004 (at planting), December 2004 (3 mo after planting [MAP]), March 2005 (6 MAP), June 2005 (9 MAP), and September 2005 (12 MAP) and exposed to 5, 10, 15, 20, 30, and 50 µg L−1fluridone to assess changes in susceptibility to this herbicide over time. Nonlinear regression analysis was used to calculate EC50values for phytoene and β-carotene (effective fluridone concentration to increase/decrease the phytoene/β-carotene content in hydrilla plant tissue by 50% over the untreated control) at each time interval. EC50values did not change in the susceptible hydrilla biotype over time. The EC50values for phytoene and β-carotene for the susceptible biotype were 7.5 and 8.9 µg L−1, respectively, at planting and 7.6 and 9.4 µg L−1, respectively, at 12 MAP. Resistant hydrilla biotypes (R1–R5) also showed no change in EC50phytoene values over time. Although, EC50β-carotene values in resistant biotypes R1, R3, R4, and R5 did not change over time, R2 recorded a reduction in EC50β-carotene at 12 MAP. Also, a 0.5-point decrease in resistance factor was observed for all resistant biotypes. Future long-term studies are needed to evaluate stability of resistant hydrilla biotypes in the absence of fluridone selection pressure.

Fluridone has been widely used for control of the submersed aquatic weed hydrilla in Florida for over 25 years. Recently, some hydrilla biotypes were suspected of having developed resistance to fluridone. Laboratory studies were conducted to monitor changes in phytoene and β-carotene contents as a function of suspected susceptible and resistant hydrilla biotypes to fluridone treatment. Hydrilla shoot tips from each biotype were exposed to 5, 10, 15, 20, 30, and 50 μg L−1 fluridone. Higher β-carotene and lower phytoene content was observed in all resistant hydrilla biotypes compared with the susceptible. The susceptible biotype showed an increase in phytoene or a decrease in β-carotene content when treated with as little as 5 μg L−1 of fluridone, whereas much higher doses were needed for the resistant biotypes. EC50 β-carotene values of 9 and 63 μg L−1 fluridone were found in the susceptible and the most resistant biotype, respectively. Consistent levels of hydrilla injury occurred at phytoene/β c...

Activities of a surprisingly large number of herbicide families are directly or indirectly influenced by light. Herbicide mechanisms that are dependent on light or are enhanced by light fall into several different categories. These herbicides inhibit electron flow in photosystem II in the photosynthetic light reaction (e.g., triazines, phenyl ureas, and uracils), capture electrons in photosystem I in the photosynthetic light reaction (e.g., bipyridiniums such as paraquat), inhibit glutamine synthetase in the nitrogen assimilation pathway (e.g., glufosinate), inhibit protoporphyrinogen oxidase during chlorophyll biosynthesis (e.g., diphenyl ethers [DPEs] and N-phenyl heterocycles), directly inhibit carotenoid biosynthesis by inhibiting one of the desaturase enzymes (e.g., norflurazon and fluridone), or indirectly inhibit carotenoid biosynthesis by inhibiting a quinone cofactor involved in the desaturase reaction (e.g., triketones and isoxazoles). Surprisingly, in all instances the involvement of light in herbicide action is not a direct interaction of light and herbicide at the primary site of action. In addition, the events that cause tissue damage (necrosis) are not associated with the primary target and are always due to membrane damage caused by lipid peroxidation of polyunsaturated fatty acids.

Many bleaching herbicides with different core structures inhibit phytoene desaturase (PD), a membranebound enzyme in the carotenogenic pathway catalyzing the hydrogen abstraction step at the first C40 precursor of n-carotene. Prospects are good that new PD-active herbicides will be discovered by screening for bleaching activity. Accordingly, interest in PD enzymology and molecular genetics has increased. Although active carotenogenic cell-free systems are available, no isolation of PD has been achieved since the enzyme cannot be detected in its isolated form due to complete loss of activity. A portion of the Rhodobacter PD gene was incorporated into an appropriate plasmid which could be expressed in E. coli. This system was used to produce an antibody specific against PD from higher plants as well as Rhodobacter. All PDs assayed had an apparent molecular weight of 52 to 55 kDa. A Rhodobacter gene probe hybridized with a 3.1 kbBamH I fragment from Aphanocapsa which allowed us to sequence the PD gene from this cyanobacterium. Its DNA sequence matched with the apparent molecular weight of the PD band in the western blot, and a fusion-gene product was found to be immunoreactive with the Rhodobacter PD antibody, Anacystis mutants were produced exhibiting cross-resistance against norflurazon and fluorochloridone. Apparently, this resistance is due to an altered PD with concurrent decrease of inhibitor binding affinity. Cloning of the resistant gene into the wild type is in progress. Additional index words. Herbicide resistance, cell-free carotenogenic assays, phytoene desaturase. THE CAROTENOGENIC PATHWAY Chlorophylls and carotenoids are formed by plant-specific pathways, and interruption of biosynthesis by inhibitors causes bleaching of cells and plant foliage (4, 25). Carotenogenesis is affected by many agrochemicals. Carotenoids, namely carotenes and xanthophylls, play an essential role in photosynthesis by protecting chlorophyll against photooxidative destruction by singlet oxygen. This highly reactive oxygen species is formed in excess through excited chlorophyll when the photosynthetic machinery (electron transport and subsequent CO2 assimilation) operates too slowly to accommodate strong light. Protection against singlet 02 is achieved when nine or more double bonds are 'Received for publication February 22, 1990, and in revised form January 15, 1991. 2Assoc. Prof., former Grad. Student, Grad. Student, and Prof. of Plant Physiol. and Biochem., Univ. Konstanz, Konstanz, Germany. Present address of senior author Lehrstuhl fUr Physiologie und Biochemie der Pflanzen, Universitit Konstanz, D-7750 Konstanz, Germany. present in the carotenoid molecule (13) as is the case with lycopene, 5-carotene, or with the xanthophylls. These molecules physically interact with triplet state chlorophyll and dissipate its energy as heat. If a herbicide prevents carotene and xanthophyll formation, chlorophyll although formed will not accumulate either. Consequently leaves emerging after herbicide treatment will be depleted of all colored plastidic pigments. The mode of action of bleaching herbicides is inhibition of formation of carotenes. Thylakoids having an intact pigment inventory before herbicide treatment are not affected by application of the bleaching herbicide. Typically, bleaching occurs only in newly formed leaves as is well known to herbicide "screeners" in the greenhouse. This phenomenon is in contrast to peroxidative, degradative herbicides like p

Four cropping systems were evaluated from 1975 to 1977 for the control of yellow nutsedge (Cyperus esculentusL.). Crops grown in 1975 and 1976 included alfalfa (Medicago sativaL. ‘Elcamino WL-600′), barley(Hordeum vulgareL. ‘CM-67′), corn (Zea maysL. ‘Dekalb T214′), and cotton (Gossypium hirsutumL. ‘Acala SJ-2′). Herbicides used included butylate (S-ethyl diisobutylthiocarbamate) in corn, EPTC (S-ethyl dipropylthiocarbamate) in alfalfa, glyphosate [N-(phosphonomethyl)glycine] in fallow plots, and MSMA (monosodium methanearsonate) in cotton. Cotton, which was grown continuously as one of the four cropping systems, was the only crop grown in 1977. Based on weed counts, crop yields, and the consistent decline in the number of tubers, all cropping systems provided substantial control of yellow nutsedge each year. Two years of either alfalfa treated with EPTC or double cropping barley with corn treated with butylate preceeding cotton reduced the number of viable yellow nutsedge tubers by 96%. Two years of chemically fallowing plots with glyphosate following barley and preceeding cotton was 98% effective in reducing viable tubers. Treating continuous cotton with MSMA, although somewhat inferior to the above systems, reduced the number of viable nutsedge tubers by 91% in 3 yr.

Solar heating (SH) of the soil by mulching it with transparent polyethylene (PE) during the hot season elevated the soil temperature by 10 to 18 C above that of the non-mulched soil. SH for 4 to 5 weeks resulted in effective control of most summer and winter annual weeds, the effect lasting for more than 5 months after PE removal.Melilotus sulcatusDesf.,Astragalus boeticusL. and bull mallow (Malva nicaeensisAll. # MALNI) were not controlled by SH. Perennial weeds which propagate from vegetative parts were only partially controlled with short SH, but mulching for 8 to 10 weeks improved control. Mulching the soil with perforated or shaded transparent PE or black PE resulted in a smaller increase of soil temperature and thus less efficient weed control. A combination of SH with soil-incorporated EPTC (S-ethyl dipropylthiocarbamate) or vernolate (S-propyl dipropylthiocarbamate) did not improve the weed control over SH alone, but significantly enhanced the disappearance of the herbicides from the soil. SH inhibited the disappearance of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl) phenyl]-4(1H)-pyridinone} but did not change the residual phytotoxicity of bromacil (5-bromo-3-sec-butyl-6-methyluracil). SH treatment improved plant growth and increased the yield of wheat (Triticum aestivumL. ‘895′) and turnip (Brassica rapaL. ‘Purple top’), but not of parsley (Petroselinum sativumHoffm.).

Soybeans [Glycine max(L.) Merr.] are often the replacement crop when cotton (Gossypium hirsutumL.) is abandoned because of stand failure in the southern United States. Injury from cotton herbicides may be reduced if the soybean planting is delayed more than 4 weeks after cotton planting or if the original herbicide-treated area is fully tilled and a new seedbed formed. Planting delay intervals were compared with five cotton preemergence herbicides on Calloway silt loam at one location. Seedbed-preparation methods were included in a similar experiment at two locations on Sharkey silty clay. Herbicides compared were fluometuron [1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea], norflurazon [4-chloro-5-(methylamino)-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone], cyanazine {2-[[4-chloro-6-(ethylamino)-s-triazin-2-yl] amino]-2-methylpropionitrile}, perfluidone {1,1,1-trifluoro-N-[2-methyl-4-phenylsulfonyl)phenyl] methanesulfonamide}, fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone}, and diuron [3-(3,4-dichlorophenyl)-1,1-dimethylurea]. Seedbeds compared were no-till and conventional (fully tilled). Soybean planting delays after cotton planting were 20, 29, and 56 days (first year), and 15 and 29 or 15 and 30 days (second year). We found in the 2-yr studies that fluridone severely damaged soybeans both years. Fluometuron and diuron also caused damage the second year when we experienced wet, cool conditions in the spring. Most injury occurred on the clay, with yield reductions occurring even after the 30-day delay. Norflurazon was most injurious at this location. The no-tillage planting method resulted in the least herbicide injury on the silt loam and the conventional tillage method was better on the clay. Detailed studies with fluometuron under incubation conditions showed that degradation was inhibited most by low temperatures and high soil moisture.

Fluridone {1-methyl-3-phenyl-5-[3-(trifluromethyl)phenyl]-4(1H)-pyridinone} and norflurazon [4-chloro-5-(methylamino)-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone] inhibited carotenoid synthesis in wheat(Triticum aestivumL. ‘Maricopa’) seedlings and caused the accumulation of colorless carotenoid precursors, phytoene, and phytofluene. These data suggested that dehydrogenation reactions following phytoene formation were inhibited by the herbicides. Chlorophyll accumulated in the treated seedlings grown under 10 lux of light but was destroyed in seedlings illuminated with 16 klux of light. Seedlings illuminated with 16 klux of light lacked chloroplast ribosomes and normal ultrastructure whereas dark grown seedlings contained pastid ribosomes and had normal etioplast ultrastructure. The disruption of the chloroplasts and loss of chlorophyll was due to the absence of carotenoids in the treated plants, which would normally act to protect the chloroplasts from photodestruction.

The effects of 16 herbicides from 14 different chemical classes on levels of soluble protein, hydroxyphenolics, anthocyanin, and chlorophyll were determined in light- and dark-grown soybean [Glycine max(L.) Merr. ‘Hill’] seedlings. Growth-reducing concentrations of the herbicides were supplied to 3-day-old dark-grown soybean seedlings in liquid culture. Soluble protein (per axis) was reduced by fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone}, paraquat (1,1′-dimethyl-4,4′-bipyridinium ion), perfluidone {1,1,1-trifluoro-N-[2-methyl-4-(phenylsulfonyl)phenyl] methanesulfonamide}, and propanil (3′,4′-dichloropropionanilide) 24 or 48 h after treatment. In light-grown plants, soluble hydroxyphenolic compound levels were decreased on a per axis basis after 48 h by all chemical treatments except by atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine], the methyl ester of diclofop {2-[4-(2,4-dichlorophenoxy)phenoxy] propanoate}, DSMA (disodium methanearsonate), fluridone, MH (1,2-dihydro-3,6-pyridazinedione), nitralin [4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline], TCA (trichloroacetic acid), and 2,4-D [(2,4-dichlorophenoxy)acetic acid]. Total chlorophyll content in hypocotyls of these seedlings was decreased by fluridone, metribuzin [4-amino-6-tert-butyl-3-(methylthio)-as-triazin-5 (4H)-one], norflurazon [4-chloro-5-(methylamino)-2-(α,α,α-trifluoro-m-tolyl)-3 (2H)-pyridazinone], paraquat, and 2,4-D, but others had no significant effect. Anthocyanin accumulation in hypocotyls of 48-h light-grown seedlings was decreased by atrazine, fenuron (1,1-dimethyl-3-phenylurea), metribuzin, norflurazon, paraquat, propanil, and propham (isopropyl carbanilate). Phenylalanine ammonia-lyase (PAL) activity (previously reported work) was positively correlated with anthocyanin levels in tissues after treatment with these 16 herbicides, but not with glyphosate [N-(phosphonomethyl)glycine]. There was, however, no correlation between extractable PAL activity and chlorophyll, soluble hydroxyphenolic compounds, or soluble protein content. These results indicated that extracted PAL activities usually reflect relative in vivo activities and that PAL activity is limiting to phenylpropanoid synthesis in vivo.

Adsorption isotherms were obtained for buthidazole {3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone}, VEL 3510 {1-β,β-dimethoxy-1-methyl-3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]urea}, tebuthiuron {N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-N,N′-dimethylurea}, and fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4 (1H)-pyridinone} on soil organic matter (H- and Ca-saturated), Ca-montmorillonite, and Cape Fear sandy loam soil. Prometryn [2,4-bis(isopropylamino)-6-(methylthio)-s-triazine] was included as a reference. The order of adsorption on all adsorbents was fluridone ≥ prometryn > > tebuthiuron ≥ VEL 3510 > buthidazole. Fluridone adsorption on the various adsorbents was: H-organic matter > Ca-montmorillonite > Ca-organic matter > > Cape Fear sandy loam. Tebuthiuron, VEL 3510, and buthidazole adsorption on the various adsorbents was in the order: H-organic matter > Ca-organic matter = Ca-montmorillonite > Cape Fear sandy loam. Adsorption of all herbicides increased with decreasing pH, suggesting that the adsorption mechanism was molecular under neutral pH conditions and ionic under acidic conditions. All of the herbicides were adsorbed in high amounts as protonated species on IR-120-H cation exchange resin and in low amounts as molecular species on IR-400-Cl anion exchange resin. Buthidazole and VEL 3510 were adsorbed in high amounts as anionic species by the IR-400-Cl exchange resin at high pH levels.

Response of grain sorghum [Sorghum bicolor(L.) Moench. ‘BR 64’] to norflurazon [4-chloro-5-(methylamino)-2-(3-(trifluoromethyl)phenyl)-3(2H)-pyridazinone] and fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl) phenyl]-4(1H)pyridinone} and the effect of previous treatment on the persistence of herbicide activity in five soils were determined in the greenhouse. Relative phytotoxicity of fluridone in the soils was ordered as Greenville sandy clay loam > Appling coarse sandy loam > Dothan loamy sand = Rome gravelly clay loam > Bradson clay loam. Phytotoxicity of norflurazon was ordered as Greenville = Appling = Dothan > Rome > Bradson. Fluridone was more phytotoxic than norflurazon. Field soil that has been previously treated with norflurazon or fluridone (500 days earlier at 1.7 kg ai/ha) still had low concentrations of each herbicide present at the time of retreatment in the greenhouse. Previous treatment of norflurazon did not affect the rate of decline in activity in any of the soils compared to previously nontreated soils except for Appling. Significantly higher concentrations of norflurazon remained in all previously treated soils 297 days after treatment (DAT) compared to previously nontreated soil. Residual carryover of norflurazon was greater in the Bradson soil (2.8% O.M.) than soils having less than 2% O.M. Fluridone dissipation was significantly faster in previously treated soil than in previously nontreated soil, indicating enhanced microbial degradation of the herbicide.

Adsorption and desorption characteristics of fluridone (1-methyl-3-phenyl-5-[3-txifluoromethyl)phenyl]-4-(1H)-pyridinone} on prepared clays and organic matter were studied in unbuffered and buffered aqueous solutions. In unbuffered aqueous solution the adsorption of fluridone decreased in the order: H-saturated organic matter (H-OM) > Ca-saturated montmorillonite (Ca-mont) > Ca-saturated organic matter (Ca-OM) > kaolinite. Based on the chemistry of fluridone, the nature of the adsorbent, and previously reported studies, the major adsorption mechanisms appear to be pH-dependent adsorption of protonated fluridone and direct protonation of the herbicide at acidic surfaces, supplemented by physical adsorption forces such as van der Waals attractions and charge transfer bonds. The adsorption of fluridone on Norfolk sand (Typic Paleudult; fine-loamy, siliceous, thermic), unmodified (CK), or amended with montmorillonite (HC) or organic matter (HM) at pH 4.0, 5.2, and 7.0 was also studied. Over all adsorption was greatest on HC soil, least on CK soil, and intermediate on the HM soil. In each system adsorption was inversely related to pH. These results were interpreted by comparison with adsorption observed on prepared clay minerals and organic matter.

Field research was conducted in 1982 and 1983 to characterize the persistence of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)pyridinone} in five Georgia soils. Fluridone persisted less than 365 days in all soils, with shorter persistence upon reapplication in 1983 which indicated the potential for enhanced microbial degradation. A significantly higher rate of loss in 1983 compared to 1982 was recorded in the Greenville sandy clay and Dothan loamy sand soils. A higher rate of loss was recorded for the 1.7 kg ai/ha than the 0.6 kg/ha treatment in the Bradson clay loam and Rome gravelly clay loam soils. No grain sorghum [Sorghum bicolor(L.) Moench. ‘BR 64’) injury was observed in a field bio assay planted in the spring of 1984. Herbicide leaching did not appear to be an important method of loss.

Pretreatment of etiolated cucumber cotyledons with potassium (K), benzyladenine (BA), or δ-aminolevulinic acid (ALA) for 20 h in the dark, followed by exposure to light for 24 h, increased chlorophyll and carotenoid content. A similar treatment with fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} decreased the levels of these photosynthetic pigments. However, when the etiolated cotyledons were pretreated with either BA or ALA for 20 h in the dark, followed by fluridone during a 24-h light period, the inhibitory effects of fluridone on chlorophyll content were reversed and the values were higher than the controls. In these treatments, ALA did not counteract the inhibitory effects of fluridone on carotenoids, but BA reduced the effects. In the cucumber cotyledon greening system, K was found to be most effective in stimulating both chlorophyll and carotenoid accumulation. When K was administered to the cotyledons either together with, prior to, or after the fluridone treatment, the inhibitory effect of fluridone on chlorophyll accumulation was totally eliminated and the stimulatory effects due to K were still maintained. Although K increased carotenoid content, it did not reverse the inhibitory effect of fluridone on carotenoids. From these findings it is concluded that the inhibition of chlorophyll and carotenoid accumulation by fluridone may be mediated via unrelated mechanisms at fluridone concentrations that do not totally eliminate or drastically reduce carotenoid content.

The effect of 1.0 ppmw fluridone {1-methyl-3-phenyl-5-[3-trifluoromethyl)phenyl]-4(1H)-pyridinone} on growth of American pondweed (Potamogeton nodosusPoir.) and sago pondweed (Potamogeton pectinatusL.) was examined in plants kept in darkness or under various numbers of 12-h photoperiods. When plants were exposed to 1.0 ppmw fluridone for 1 to 10 12-h days, no stunting of American pondweed occurred until 21 days after treatment. Thirtythree days after treatment, plants that had received 4 to 10 days' exposure were most stunted. Sago pondweed was slightly more susceptible than American pondweed (87% and 50% reduction in length, respectively) 37 days after a 10-day exposure. Chlorophyllsaandbwere significantly lower in both species 14 days after all fluridone treatments. American pondweed plants exposed to fluridone continuously (1.0 ppmw) for 15 days, but given 0, 3, 6, 9, 12, or 15 12-h days were stunted only after having received at least six photoperiods. Stunting in sago pondweed was only slightly light-dependent. Neither species absorbed significantly more14C-labeled fluridone after 2, 4, or 14 photoperiods compared to plants kept in darkness for the same time.

Residue levels of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} in soil were determined indirectly by measuring the chlorophyll content of wheat (Triticum aestivumL.) grown on a Norfolk sandy loam (Typic paleudult; fine loam, siliceous, thermic) 14, 22, 39, and66days after a preemergence application of the herbicide. The half-life for 0.22 and 0.45 kg/ha of fluridone was estimated to be 18 days. Phytotoxicity increased with increasing pH in newly-treated soils and in soil sampled 14 days after treatment. Higher chlorophyll levels in wheat grown in soil sampled 39 days after fluridone application indicated a decrease in biologically-active herbicide. Soil removed from the field following later cultivation produced small reductions in chlorophyll at pH 4.0 and 5.2, but at pH 7.0 significant fluridone activity was still present in the soil after 66 days. Cultivation may have increased the surface concentration of the herbicide.

The rate of herbicide required to reduce growth of grain sorghum (Sorghum vulgare, Per. ‘Pioneer 8417′) by 50% (GR50) and soil adsorption coefficients (Ka) were determined for the experimental herbicide, fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone}, in 14 soils. A linear correlation analysis was conducted between GR50values and the chemical and physical properties and fluridone absorption coefficient (Ka) for 14 soils. The GR50values were significantly correlated to soil organic matter and Ka. A stepwise regression analysis suggests that Kaor organic matter content can be used to predict the rate of fluridone application required for herbicidal activity.

The uptake and translocation of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} were examined in sago pondweed (Potamogeton pectinatusL.) and Richardson pondweed [Potamogeton richardsonii(Ar. Benn.) Rydb.]. Root and shoot tissues of both species were isolated from each other with wax barriers and treated individually with 1.0 ppm14C-fluridone. Both tissues bioconcentrated fluridone, but the amount absorbed represented 1% or less of the total herbicide available. Limited root-to-shoot translocation occurred, but shoot-to-root transport was negligible. In contrast to fluridone, highly mobile glyphosate [N-(phosphonomethyl) glycine] translocated from the shoots to the roots in sago pondweed. No metabolism of fluridone was detected in sago pondweed.

Bioassay and gas chromatographic procedures were evaluated for their effectiveness in detecting fluridone [1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone] in soil. Bioassay procedures were limited to a detection range of 0.05 to 0.45 ppmw if grain sorghum (Sorghum bicolor(L.) Monech) was used. Visual estimations of chlorophyll content in affected plants, used as an indicator of fluridone concentration, were as reliable as spectrophotometric determinations. Gas-liquid chromatographic (GLC) procedures were less variable than the bioassay and had no upper limit of detection. Recovery of fluridone from treated soil ranged from 60 to 100 percent, depending on soil type. Soil water content affected percent recovery. Fluridone did not leach more than 1 cm in clay or sandy loam soils when up to 10 cm of water was passed through a soil column containing the herbicide, as determined by GLC. Extensive downward movement, 12 to 16 cm, occurred in a coarse sand when 5 or 10 cm of water was passed through the column.

Aqueous solutions of buthidazole {3-[5-(1,1-dimethylethyl)-1,3,4-thiadazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone}, VEL 3510 {1-β,β-dimethoxyethyl-1-methyl-3-[5-(1,1-dimethylethyl)-1,3,4-thiadazol-2-yl] urea}, tebuthiuron {N-[5-(1,1-dimethylethyl)-1,3,4-thiadazol-2-yl]-N,N′-dimethylurea}, fluridone 1-methyl-3-phenyl-5-[3-trifluoromethyl)phenyl]-4(1H)-pyridinone, metribuzin [4-amino-6-tert-butyl-3-(methylthio)-as-triazin-5(4H)-one], and prometryn [2,4-bis(isopropylamino)-6-(methylthio)-s-triazine] were spectrophotometrically titrated to obtain pKAvalues. Ionizing properties of the chemicals were compared with other related compounds reported in the literature. The pKAvalues for the six herbicides were 0.6 and 11.3, 0.9 and 9.0, 1.2, 1.7, 1.1, and 4.1, respectively.

In greenhouse experiments, sago pondweed plants were grown from three different size classes of tubers and treated with four levels of fluridone. Results indicate that although fluridone significantly reduced mean plant weight, the extent of the reduction in weight depended on the size of tuber from which the plant was grown. Mean plant weight was greater for plants exposed to fluridone (up to 0.5 mg/L) for 7 days, if the plants were initially from larger tubers (51 to 60 or 101 to 200 vs. 11 to 20 mg fresh weight). Mean plant length and the number of ramets/plant were affected in a similar manner. The results underscore the importance of specifying the size of tubers used in growth studies and contribute to understanding of the roles that biological factors play in regulating aquatic plant response to herbicide treatment.

The double pot technique was used to study the effects of uptake site of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl—phenyl]-4(1H)-pyridinone} on early shoot and root development of soybean [Glycine max(L.) Merr. ‘Williams’] and cotton (Gossypium hirsutumL. ‘Acala SJ-1′). Soybean is susceptible and cotton is resistant to fluridone. Root uptake in soybean resulted in increased shoot length in the epicotyl and shoot apex, reduced shoot fresh weight, chlorosis of primary and trifoliolate leaves, as well as reduced root length, branching, and fresh weight. Shoot uptake resulted in reduced shoot length above the hypocotyl, reduced shoot weight, severe chlorosis of primary leaves, and inhibition of trifoliolate leaf formation. The reduction in the root length, branching, and weight was less by shoot uptake than by root uptake. In cotton, root uptake resulted in reduced shoot length in the epicotyl and shoot apex, slight reduction in shoot weight, no effect on chlorosis of cotyledon leaves, moderate to slight chlorosis of the true leaves, and no effect on root length, branching, or fresh weight. Shoot uptake resulted in reduced length of all shoot components and shoot weight, chlorosis of cotyledon leaves and the true leaves, and reduced root length, branching, and weight. Compared to soybean, cotton required much higher fluridone concentrations to show the above effects. It was generally concluded that in soybean, uptake by both the root and the shoot contributed significantly to the injury, whereas in cotton, shoot uptake was relatively more important.

Two 1-yr field studies were conducted to evaluate preemergence and preplant incorporated treatments of alachlor [2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide], EPTC (S-ethyl dipropylthiocarbamate), fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone}, and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide] for the control of yellow nutsedge (Cyperus esculentusL.). Preemergence applications of metolachlor at 2.24, 3.36, and 4.48 kg/ha gave the best control with no significant differences observed among rates of metolachlor. Depth of herbicide incorporation did not result in any significant increase in control. Preplant incorporation of metolachlor at all rates, or fluridone at 0.56 and 0.84 kg/ha provided seasonal control of yellow nutsedge. Translocation of14C-metolachlor applied to the root or shoot of yellow nutsedge was primarily acropetal with some limited basipetal movement. Application of14C-metolachlor to the root or shoot of purple nutsedge (Cyperus rotundusL.) resulted in mostly acropetal translocation with little movement of14C from the treatment site.

A fiber system for controlled delivery of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} was evaluated for its potential use in the management of the submersed aquatic weed hydrilla [Hydrilla verticillata(L.f.) Royle # HYLLI] in slow-moving water. The release of fluridone from the fibers was first order and could be extended over several days simply by using fibers of larger diameters. Fibers of 0.8- and 1.2-mm diam released fluridone over a period of 40 and 50 days, respectively. Both effectively controlled hydrilla at a rate of 2.2 kg ai/ha in a 4-month study in replicated pools with water flow adjusted to provide one volume change every 24 h. Under the same conditions, the conventional liquid formulation was ineffective and a pellet formulation provided only marginal control.

Nine soil-applied herbicides were evaluated in the field in cotton (Gossypium hirsutumL.) and soybeans [Glycine max(L.) Merr.] and in the greenhouse without crops to determine their effects on the control, regrowth, and tuber production of yellow nutsedge (Cyperus esculentusL.). Fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl) phenyl]-4(1H)-pyridinone} and norflurazon [4-chloro-5-(methylamino)-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone] provided the best (100%) control in the greenhouse. Tubers exposed to herbicide-treated soil in the greenhouse for 4 or 8 weeks produced fewer new tubers when transplanted into nontreated soil than nontreated tubers did. Yellow nutsedge shoot and tuber populations in the field were significantly reduced by all herbicides, except for alachlor [2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide], after 2 yr of treatment in cotton and soybeans.

Time- and concentration-course studies were conducted to determine the metabolic sites of action of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} in isolated mesophyll cells of cotton (Gossypium hirsutumL. ‘Acala SJ-1′) and red kidney bean (Phaseolus vulgarisL.). Cotton is resistant and bean is susceptible to fluridone. The herbicide was not metabolized in cells of either species during the 2-h incubation period. At the highest concentration (10-4M) and longest incubation time (2 h), fluridone inhibited photosynthesis, RNA synthesis, and protein synthesis 59, 56, and 32%, respectively in bean and 24, 21, and 14% in cotton. Lipid synthesis and dark respiration were only slightly affected. The lowest concentration and the shortest incubation period that inhibited photosynthesis, RNA synthesis, and protein synthesis in bean did not have any significant effect in cotton. The difference in responses may contribute to the selectivity of the herbicide. Although photosynthesis appeared to be the primary site of action, RNA synthesis was also markedly inhibited. These inhibitions and the somewhat lower inhibition of protein synthesis may ultimately contribute to the herbicidal action of fluridone in the intact plant.

The concentration of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone} residue in Miller clay and Lufkin fine sandy loam was determined at various intervals following incorporated and nonincorporated applications in the field. Low levels of fluridone were present in Miller clay after 250 days while up to 25% remained in Lufkin fine sandy loam 385 days after treatment. Incorporation of fluridone increased its persistence in, Lufkin fine sandy loam but not in Miller clay. Fluridone degradation in Miller clay and Lufkin fine sandy loam was more rapid in the field than under controlled conditions. Fluridone degradation in sterilized Brennan fine sandy loam and Hidalgo sandy clay loam was significantly slower than in nonsterilized soil kept under the same conditions. These differences were not observed in Lufkin fine sandy loam and Miller clay.

The uptake, translocation, and metabolism of the herbicide fluridone 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone was studied in cotton (Gossypium hirsutum L. ‘Stoneville 213’) (fluridone tolerant) and corn (Zea mays L. ‘Migro 5040’), soybean [Glycine max (L.) Merr. ‘Calland’], and rice (Oryza sativa L. ‘Nato’) (fluridone susceptible). Uptake studies with 14C fluridone demonstrated that all species absorbed radioactivity with rice having the highest concentration. Equivalent concentrations of radioactivity were observed in corn, cotton, and soybean. Absorbed fluridone was retained primarily in the roots and the basal region of the stem of cotton, while in the herbicide susceptible species fluridone was readily translocated into the shoots. No appreciable metabolism of fluridone was observed in the roots or shoots of cotton and soybean. Tolerance of cotton to fluridone was primarily attributed to the limited translocation of the compound.

Chlorophyll content of wheat (Triticum aestivum L. ‘Mericopa’) and corn (Zea mays L. ‘Merit’) treated with the herbicide fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)-phenyl]-4(1H)-pyridinone} and grown under high light intensity (10.8 klux), was markedly reduced. Corn and wheat germinated from seeds treated with 10 uM fluridone and grown for 6 days were almost completely bleached. Under low light intensity (108 lux) the influence of fluridone on chlorophyll production was greatly reduced. Under very low light intensity (21.5 lux) this influence was almost completely lost. The effect of light on the activity of fluridone suggests that the inhibition of carotenoid production may represent the mode of action of this herbicide. This study shows that the carotenoid content of wheat or corn drops dramatically when these plants are treated with fluridone.

Fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4 (1H)-pyridinone} and R-4-0244 [1-(m-trifluoromethylphenyl)-3-chloro-4-chloromethyl-2-pyrrolidone], herbicides that block carotenoid synthesis, increase the sensitivity of corn (Zea maysL. ‘Merit’) to exogenously-applied gibberellic acid (GA). Increase in shoot length due to the application of GA to imbibing corn seeds was considerably enhanced by simultaneously applying either fluridone or R-40244. Fluridone was more active in this respect than R-40244.