at . z. ,. afimwmrs w. a. .H t u: it»), 5,1. , 145:» 3 4%. .. a? Jan». . c ‘ wt . . , H.125; 71 1‘ 3:... at. (I? l . .2? .2. 31 :2; r N. 11:35 53;): .Y 99‘. 2) . AI .3 $11.32;"; 3.7.: ”I ‘5.) . (I. a Ayggqfi M AN "1??? muuummlit'fiw TE I RAH! i 1 [iii “W 7710 3 1293 LIBRARY Michigan State University This is to certify that the dissertation entitled ENHANCING POSTEMERGENCE WEED CONTROL PROGRAMS IN CORN AND SOYBEAN WITH FLUTHIACET AND FLUMICLORAC presented by JASON C. FAUSEY has been accepted towards fulfillment of the requirements for PhoDo degreein Crop and SOil Sciences {51% a (WW I Major professor Date gZ/m / H99 L// J MSU i: an Affirmative Action/Equal Opportunity Institution 0-12771 PLACE IN RETURN BOX to remove this checkout from your record. To AVOID FINES return on or before date due. MAY BE RECALLED with earlier due date if requested. DATE DUE DATE DUE DATE DUE ma cane/0.03M“ ENHANCING POSTEMERGENCE WEED CONTROL PROGRAMS IN CORN AND SOYBEAN WITH FLUTHIACET AND FLUMICLORAC By Jason C. Fausey A DISSERTATION Submitted to Michigan State University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Department of Crop and Soil Sciences 1999 1h: V6 en. 561 to] her COl det‘ exp eff]. 100 hum herb SlL ABSTRACT ENHANCING POSTEMERGENCE WEED CONTROL PROGRAMS IN CORN AND SOYBEAN WITH FLUTHIACET AND F LUMICLORAC BY Jason C. Fausey The recently developed cyclic imide herbicides fluthiacet and flumiclorac control one of the most troublesome broadleaf weeds, velvetleaf. These herbicides selectively control velvetleaf and other broadleaf weeds by inhibiting the protoporphyrinogen IX oxidase enzyme. Studies examined the physiological basis for fluthiacet and flumiclorac selectivity in five plant species. Enhanced herbicide metabolism contributed to the tolerance of redroot pigweed to fluthiacet and wild mustard to flumiclorac. Decreased herbicide retention, absorption, and translocation; and increased herbicide metabolism contributed to com tolerance to these herbicides. Soybean tolerance resulted from decreased herbicide retention and increased herbicide metabolism. Experiments examined the effect temperature, light intensity, time to initial light exposure, relative humidity, and the presence of dew have on fluthiacet and flumiclorac efficacy. Increasing temperature from 10 to 40 C and increasing light intensity from O to 1000 umol rn’2 3'1 increased herbicide activity. Time to initial light exposure and relative humidity did not affect fluthiacet and flumiclorac activity. The presence of dew reduced herbicide activity. Studies evaluated broadleaf weed control with fluthiacet and flumiclorac applied alone w—vr‘ b3: cro- nag \clx piam 3.4-E Plguc lath n COED. 1 Field llULHfac am}, 17 Wilde ‘ lzerbjci'dc and in tank mixtures. Velvetleaf, common lambsquarters, redroot pigweed, common ragweed, common cocklebur, eastern black nightshade, and wild mustard growth in the greenhouse were reduced by 50% from 0.1, 2.9, 0.9, 1.1, 0.8, 0.4, and 1.2 g ha'l of fluthiacet and 0.7, 3.0, 2.4, 3.3, 3.0, 3.4, and 74.1 g ha" of flumiclorac, respectively. Adjuvants enhanced common lambsquarters, redroot pigweed, common ragweed, and velvetleaf control with fluthiacet by 53, 57, 29, and 29% and with flumiclorac by 36, 62, 41, and 34%, respectively, in the greenhouse. In field studies, soybean injury and broadleaf weed control were equivalent when fluthiacet or flumiclorac was applied with a crop oil concentrate or a nonionic surfactant. Velvetleaf control with these herbicides was greatest in the field when applied to S cm tall plants. However, season-long velvetleaf control with both herbicides was greatest when applied to 45 or 60 cm tall plants. In field studies, fluthiacet and flumiclorac tank mixtures with atrazine, dicamba, 2,4-D, and primisulfuron plus prosulfuron controlled common lambsquarters, redroot pigweed, and velvetleaf season-long. Similarly, tank mixing fluthiacet or flumiclorac with imazethapyr provided season-long common lambsquarters, redroot pigweed, common ragweed, and eastern black nightshade control. Field studies evaluated the performance of annual weed control programs that included fluthiacet and flumiclorac. Experiments revealed these herbicides are effective applied in a tank mixture with other postemergence herbicides. Alternatively, these herbicides provide excellent weed control when applied postemergence following a preemergence herbicide application. USIOF lNTROD CHAPTI in NI TABLE OF CONTENTS PAGE LIST OF TABLES .................................................... vii INTRODUCTION ...................................................... 1 CHAPTER 1. PHYSIOLOGICAL BASIS FOR FLUTHIACET AND FLUMICLORAC SELECTIVITY. Abstract ......................................................... 2 Introduction ..................................................... 4 Materials and Methods ............................................ 6 Electrolyte Leakage ......................................... 6 General Greenhouse Methods ................................ 6 Species Sensitivity .......................................... 7 Herbicide Retention ......................................... 8 Herbicide Absorption, Translocation, and Metabolism ............ 9 Statistical Analyses ......................................... 12 Results and Discussion ............................................ 12 Herbicide Effect on the Porphyrin Pathway .................... 12 Electrolyte Leakage .................................. 12 Fluthiacet and Flumiclorac Selectivity ......................... 14 Species Sensitivity ................................... 14 Herbicide Retention .................................. 14 Herbicide Absorption ................................ 15 Herbicide Translocation .............................. 16 Herbicide Metabolism ................................ 16 Acknowledgments ......................................... 19 Literature Cited ................................................. 20 CHAPTER 2. ENVIRONMENTAL EFFECTS ON F LUTHIACET AND FLUMICLORAC EFFICACY AND SOYBEAN TOLERANCE. Abstract ........................................................ 30 Introduction .................................................... 32 Materials and Methods ........................................... 34 General Methods for Laboratory Experiments ................. 34 Temperature ........................................ 35 Light Intensity ...................................... 35 Time to Initial Light Exposure ......................... 35 Relative Humidity ................................... 35 Influence of Dew on Efficacy .......................... 36 iv Cl TABLE OF CONTENTS (cont.) PAGE Field Experiment .......................................... 37 Statistical Analyses ......................................... 38 Results and Discussion ............................................ 38 Laboratory Experiments .................................... 38 Temperature ........................................ 38 Light Intensity ...................................... 39 Time to Initial Light Exposure ......................... 39 Relative Humidity ................................... 40 Influence of Dew on Efficacy .......................... 40 Field Experiment .......................................... 40 Acknowledgments ......................................... 43 Literature Cited ................................................. 44 CHAPTER 3. ADJUVANT EFFECTS ON FLUTHIACET AND FLUMICLORAC EFFICACY AND SOYBEAN TOLERANCE. Abstract ........................................................ 54 Introduction .................................................... 57 Materials and Methods ........................................... 59 General Methods for Laboratory Experiments ................. 59 Adjuvant Efficacy ................................... 60 Tank Mixtures with Fluthiacet and Flumiclorac .......... 60 Field Experiments ......................................... 61 Species Sensitivity ................................... 61 Tank Mixtures with Fluthiacet and Flumiclorac .......... 62 Statistical Analyses ......................................... 63 Results and Discussion ............................................ 64 Adjuvant Efficacy ................................... 64 Tank Mixtures with Fluthiacet and Flumiclorac ................ 66 Greenhouse ......................................... 66 Field ............................................... 66 Acknowledgments ......................................... 68 Literature Cited ................................................. 69 CHAPTER 4. BROADLEAF WEED CONTROL IN CORN AND SOYBEAN WITH FLUTHIACET AND F LUMICLORAC ALONE AND IN TANK MIXTURES. Abstract ........................................................ 77 Introduction .................................................... 80 Materials and Methods ........................................... 82 IA CH TABLE OF CONTENTS (cont.) PAGE General Methods for Laboratory Experiments ................. 82 Species Sensitivity ................................... 83 Tank Mixtures with Fluthiacet and Flumiclorac .......... 84 Field Experiments ......................................... 85 Corn ............................................... 85 Soybean ............................................ 86 Statistical Analyses ......................................... 87 Results and Discussion ............................................ 88 Greenhouse Experiments ................................... 88 Species Sensitivity ................................... 88 Tank Mixtures with Fluthiacet and Flumiclorac .......... 89 Field Experiments ......................................... 91 Corn ............................................... 91 Soybean ............................................ 92 Acknowledgments ......................................... 95 Literature Cited ................................................. 96 CHAPTER 5. INCORPORATING FLUTHIACET AND FLUMICLORAC INTO ANNUAL WEED CONTROL PROGRAMS FOR CORN AND SOYBEAN. Abstract ....................................................... 105 Introduction ................................................... 108 Materials and Methods .......................................... 109 Greenhouse Experiments .................................. 109 Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures ............. 109 Field Experiments ........................................ 1 1 1 Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures ............. 111 Velvetleaf Control .................................. l 11 Annual Weed Control in Corn ........................ 112 Annual Weed Control in Soybean ..................... 114 Statistical Analyses ........................................ 1 16 Results and Discussion ........................................... 116 Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures ............. 116 Weed Control Programs ................................... 117 Velvetleaf Control .................................. 117 Annual Weed Control in Corn ........................ 117 Annual Weed Control in Soybean ..................... 118 Acknowledgments ........................................ 121 Literature Cited ................................................ 122 vi CHAP CHAP LIST OF TABLES CHAPTER 1. PHYSIOLOGICAL BASIS FOR FLUTHIACET AND FLUMICLORAC SELECTIVITY. Table 1. Table 2. Table 3. Table 4. Table 5. Table 6. Table 7. PAGE Characterization of fluthiacet and flumiclorac metabolites ...... 23 Effect of 4,6-dioxoheptanoic acid (DA) on electrolyte leakage 24 h after fluthiacet and flumiclorac treatment ................ 24 Effect of aminolevulinic acid (ALA) on electrolyte leakage 24 h after fluthiacet and flumiclorac treatment ................ 25 Species sensitivity to 2 g ha‘l fluthiacet and 15 g ha‘l flumiclorac in the greenhouse 14 d after treatment ....................... 26 Fluthiacet and flumiclorac retention in five plant species ........ 27 Fluthiacet and flumiclorac absorption, translocation, and metabolism in five plant species ............................. 28 Factors affecting plant tolerance to fluthiacet and flumiclorac 12 h after treatment ..................................... 29 CHAPTER 2. ENVIRONMENTAL EFFECTS ON F LUTHIACET AND FLUMICLORAC EFFICACY AND SOYBEAN TOLERANCE. Table 1. Table 2. Table 3. Table 4. Table 5. Table 6. Table 7. Effect of temperature on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment ...................................... 47 Effect of light intensity on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment ...................................... 48 Effect of time to initial light exposure on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment ...................................... 49 Effect of relative humidity on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment ...................................... 50 Effect of dew on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment ...................................... 51 Herbicide application conditions in 1996, 1997, and 1998 field experiments ................................. 52 Effect of time of application on tolerance and efficacy of fluthiacet and flumiclorac applied at 0600, 1400, and 2000 h ..... 53 vii LBT( CHAP CH! Cl LIST OF TABLES (Cont) PAGE CHAPTER 3. ADJUVANT EFFECTS ON F LUTHIACET AND FLUMICLORAC EFFICACY AND SOYBEAN TOLERANCE. Table 1. Adjuvant effect on fluthiacet efficacy in the greenhouse 14 d after treatment ....................... 72 Table 2. Adjuvant effect on flumiclorac efficacy in the greenhouse 14 d after treatment ....................... 73 Table 3. Adjuvant effect on fluthiacet or flumiclorac soybean tolerance and efficacy in the field .................... 74 Table 4. Broadleaf weed control in the greenhouse with fluthiacet and flumiclorac tank mixtures 14 d after treatment . . . 75 Table 5. Weed control and soybean yield in the field with fluthiacet and flumiclorac alone and in tank mixtures ................... 76 CHAPTER 4. BROADLEAF WEED CONTROL IN CORN AND SOYBEAN WITH FLUTHIACET AND FLUMICLORAC ALONE AND IN TANK MIXTURES. Table l. Weed species sensitivity to fluthiacet and flumiclorac in the greenhouse ......................................... 99 Table 2. Corn injury 3 d after treatment (DAT) and broadleaf weed control 14 DAT in the greenhouse with fluthiacet or flumiclorac tank mixtures ..................... 100 Table 3. Soybean injury 3 d after treatment (DAT) and broadleaf weed control 14 DAT in the greenhouse with fluthiacet or flumiclorac tank mixtures ..................... 101 Table 4. Corn injury, broadleaf weed control, and corn yield in the field with fluthiacet or flumiclorac tank mixtures ....... 102 Table 5. Soybean injury, broadleaf weed control, and soybean yield In the field with fluthiacet or flumiclorac tank mixtures ....... 104 CHAPTER 5. INCORPORATING FLUTHIACET AND FLUMICLORAC INTO ANNUAL WEED CONTROL PROGRAMS IN CORN AND SOYBEAN. Table 1. Giant foxtail and barnyardgrass control with fluthiacet and flumiclorac tank mixtures in the greenhouse 14 d after treatment ...................... 124 Table 2. Giant foxtail and barnyardgrass control with fluthiacet and flumiclorac tank mixtures in the field 28 d after treatment ............................ 125 Table 3. Corn injury and velvetleaf control with fluthiacet and flumiclorac in the field ....................... 126 viii LIST OF TABLES (Cont.) PAGE Table 4. Corn injury, weed control, and corn yield with fluthiacet and flumiclorac alone and in tank mixtures ......... 127 Table 5. Soybean injury, weed control, and soybean yield in 1997 with fluthiacet and flumiclorac alone and in tank mixtures ......... 129 Table 6. Soybean injury, weed control, and soybean yield in 1998 with fluthiacet and flumiclorac alone and in tank mixtures ......... 131 ix INTRODUCTION Velvetleaf (Abutilon theophrasti Medik.) is one of the most troublesome weeds in agricultural crops. Acceptable postemergence velvetleaf control in corn (Zea mays L.) and soybean (Glycine max (L.) Merr.) was difficult before the development of fluthiacet and flumiclorac. These herbicides provide unprecedented postemergence velvetleaf control and offer several advantages over other commercial postemergence herbicides including low use rates, short half-lives, rapid bumdown, resistance management, and the ability to broaden the spectrum of other com and soybean herbicides when applied in a tank mixture. Additionally, each herbicide provides a varying degree of activity on common lambsquarters (Chenopodium album L), kochia (Kochia scoparia L.), Amaranthus species, Solanaceae species, and other broadleaf weeds. Understanding the mechanism of selectivity would provide information that may be used to maximize fluthiacet and flumiclorac efficacy of marginally controlled weeds. To determine the most effective way to use fluthiacet and flumiclorac, research will determine the basis of selectivity, evaluate the effect environmental conditions at application have on efficacy, examine the effect adjuvant selection has on efficacy, examine tank mixture interactions, and establish an optimal system that incorporates these herbicides into corn and soybean weed control programs. flL CHAPTER 1 Physiological Basis for Fluthiacet and Flumiclorac Selectivity in Five Plant Species ABSTRACT Greenhouse and laboratory studies were conducted to determine the physiological basis for fluthiacet and flumiclorac selectivity in five plant species. These herbicides selectively control weeds postemergence by inhibiting protoporphyrinogen oxidase (Protox). Injury symptoms include rapid desiccation and necrosis, Similar to diphenyl ether and bipyridinium herbicide injury. Species sensitivity was evaluated by comparing the dry weight reduction from postemergence fluthiacet and flumiclorac applications. Velvetleaf was sensitive to both herbicides, redroot pigweed was more sensitive to flumiclorac than fluthiacet, wild mustard was sensitive to fluthiacet yet tolerant to flumiclorac, and corn and soybean were tolerant to both herbicides. Studies evaluated the effects of herbicide retention, absorption, translocation, or metabolism on fluthiacet and flumiclorac selectivity. Enhanced herbicide metabolism contributed to the tolerance of redroot pigweed to fluthiacet and wild mustard to flumiclorac. Decreased herbicide retention, absorption, and translocation; and increased metabolism contributed to corn tolerance to fluthiacet and flumiclorac. Decreased herbicide retention and increased .ah herbicide metabolism provided soybean tolerance to these herbicides. Nomenclature: Fluthiacet, [[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H- [1 ,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)arnino]phenyl]thio]acetate; flumiclorac, pentyl[2-chloro-4-fluoro-5-(1 ,3,4,5 ,6,7-hexahydro- l ,3-dioxo-2H-isoindol-2— yl)phenoxy]acetic acid; velvetleaf, Abutilon theophrasti Medik. #' ABUTH; redroot pigweed, Amaranthus retroflexus L. # AMARE; wild mustard, Brassica kaber, (D.C.) L.C. Wheeler # SINAR; corn, Zea mays L.‘Pioneer 3751’ # ZEAMA; soybean, Glycine max (L.) Merr. ‘Conrad’ # GLYMA. Key Words: Absorption, metabolism, protoporphyrin, retention, translocation, ABUTH, AMARE, SINAR, ZEAMA, GLYMA. Abbreviations: ALA, 6-aminolevulinic acid; DA, 4,6-dioxoheptanoic acid; DAT, days after treatment; HAT, hours after treatment; LSS, liquid scintillation spectrometry; MES, 2-(N-morpholino) ethanesulfonic acid; NIS, nonionic surfactant; Proto, protoporphyrin IX; Protogen, protoporphyrinogen IX; Protox, protoporphyrinogen oxidase; TLC, thin layer chromatography; v/v volume per volume. lLetters following this symbol are a WSSA-approved computer code from Composite List of Weeds, Revised 1989. Available from WSSA, 810 East 10th Street, Lawrence, KA 66044-8897. 1'9 10 SI] 16‘: pr Pr dc 5P he INTRODUCTION F luthiacet and flumiclorac are recently developed cyclic irnide herbicides that selectively control broadleaf weeds postemergence in corn and soybean (Porpiglia et a1. 1994; Kamoshita et a1. 1993). F luthiacet and flumiclorac have a similar mode of action to diphenyl ether, oxadiazole, and triazolinone herbicides despite their different chemical structures (Sato et al. 1991). These herbicides inhibit the protoporphyrinogen oxidase (Protox) enzyme in susceptible plant species which leads to an uncontrolled nonenzymatic oxidation of protoporphyrinogen IX (Protogen) to protoporphyrin IX (Proto) (Anonymous 1995; Duke et a1. 1991; Mito et al. 1991). Proto, a photodynamic tetrapyrrole intermediate, is a potent photosensitizer generating singlet oxygen in the presence of molecular oxygen and light (Duke et al. 1991). Injury in plants treated with Protox-inhibiting herbicides includes rapid light-dependent chlorophyll bleaching, desiccation, and necrosis (Wright et al. 1995). Although detectable in sensitive plant species 30 minutes after herbicide exposure, Protox inhibition requires light to initiate herbicidal activity (Duke et a1. 1990). Predicting herbicide efficacy is challenging. Environmental conditions at application (Doran and Anderson 1976), herbicide rate (King and Oliver 1992), weed size (Kells et al. 1984), interactions with other herbicides (Hatzios and Penner 1985), and the addition of an adjuvant (Roggenbuck et al. 1990) influence herbicidal activity. Enhanced herbicidal efficacy generally reflects increased herbicide absorption (Harrison and Wax 1986); however, increased herbicide absorption does not always correlate with increased efficacy (Starke et al. 1996). Ritter and Coble (1981) reported that soybean tolerance to 1hr nii CO 3.11 lb: an t.) (I; Hi the diphenyl ether herbicide acifluorfen (5-[2-chloro-4-(trifluoromethyl)phenoxy]-2- nitrobenzoic acid) was explained by less rapid herbicide absorption and translocation coupled with increased metabolism. Similarly, acifluorfen caused widespread cell membrane disruption decreasing weed control by reducing systemic herbicide absorption and translocation (Westberg and Coble 1992). Temperature and relative humidity influence Protox-inhibiting herbicides translocation and efficacy. Increasing relative humidity from 50 to 85% enhanced acifluorfen, fomesafen (5-[2-chloro-4-(trifluoromethyl)phenoxy] (methylsulfonyl)-2-nitrobenzamide), and lactofen ((:)-2-ethoxy- 1 -methy1-2-oxoethyl-5-[2-chloro-4-(trifluoromethyl)phenoxy] -2-nitrobenzoate) activity on prickly Sida (Sida spinosa L.), pitted momingglory (Ipomoea lacunosa L.), entireleaf momingglory (Ipomoea hederacea var. integriuscula L.), and common cocklebur (Xanthium strumarium L.) (Wichert et a1. 1992). However, Higgins et al. (1988) reported that acifluorfen and lactofen translocation and metabolism in pitted momingglory was negligible. Weeds prevent crops from reaching their yield potential. Fluthiacet and flumiclorac effectively control velvetleaf, one of the most troublesome broadleaf weeds in corn and soybean. However, research investigating the physiological basis for fluthiacet and flumiclorac selectivity is limited. Studies have not determined the mechanism of selectivity for these herbicides. Conceivably, research could increase control of marginally controlled weed species though crop tolerance may limit the potential to increase fluthiacet and flumiclorac efficacy. Therefore, the objective of this research was to determine the physiological basis for fluthiacet and flumiclorac selectivity in velvetleaf, redroot pigweed, wild mustard, corn, and soybean. H.- El. C 1n- Cut. MATERIALS AND METHODS Herbicide Effect on the Porphyrin Pathway Electrolyte Leakage. Experiments evaluating the effects fluthiacet and flumiclorac have on membrane integrity of velvetleaf, redroot pigweed, wild mustard, corn, and soybean leaf disks used the electrolyte leakage assay procedure described by Duke et al. (1984). Treatments included technical grade fluthiacet or flumiclorac alone or with 4,6- dioxoheptanoic acid2 (DA) or o-aminolevulinic acid2 (ALA). DA and ALA were used as a herbicide antagonist and synergist, respectively. Five-mm diameter leaf disks were excised and washed for 2 h in a 1% sucrose, 1 mM 2-(N-morpholino) ethanesulfonic acid2 (MES) solution with a pH of 6.8. Fifty leaf disks were placed in 13 by 100-mm test tubes containing 3 ml of fresh sucrose/MES solution with various rates of herbicide, antagonist, and synergist (see Tables 2 and 3). Leaf disks were added to the test tubes and incubated at 25 C in darkness for 16 h followed by exposure to 1000 amol rn‘2 s‘1 at 25 C for 24 h. The experiment was a completely randomized design with six replications and repeated. Electrolyte leakage from the leaf disks was monitored 0, 12, and 24 h after initial light exposure using a conductivity meter’. Results are expressed as the change in conductivity from the 0 h light exposure. General Greenhouse Methods Velvetleaf and wild mustard seed were collected at the Michigan State University 2 Sigma Chemical Company, St. Louis, MO 63178. 3Omega Engineering Inc., Stamford, CT 06907-0047. 6 D. CC 11: u: II"; .. 1‘ A acj Research Farm in East Lansing. Redroot pigweed seed was obtained from a commercial seed supplier‘. The corn variety ‘Pioneer 3751 ’5 and soybean variety ‘Conrad’ were used in the following studies. Seeds were planted in BACCTO6 potting soil in 946-ml plastic pots. Environmental conditions were maintained within a greenhouse at 27 i 5 C. Plants were grown under a 16-h photoperiod of natural and supplemental high pressure sodium lighting with a photosynthetic photon flux density of 1000 amol m2 5“. Plants were thinned to 1 plant pot“, fertilized with 50 ml of a water-soluble fertilizer solution (400 ppm N, 400 ppm P205, and 400 ppm K20), and watered as needed. Species Sensitivity. Experiments compared velvetleaf, redroot pigweed, wild mustard, corn, and soybean sensitivity to fluthiacet and flumiclorac. Treatments included an untreated control, 2 g ha" fluthiacet, and 15 g ha’l flumiclorac. Herbicides were applied with 0.25% (v/v) nonionic surfactant7 (NIS). At application, velvetleaf plants were 10 cm tall with five to six leaves; redroot pigweed plants were 10 cm tall with seven to eight leaves; wild mustard plants were 8 cm tall with four to five leaves; corn plants were 20 cm tall with four leaves; and soybean plants were 13 cm tall with two fully developed trifoliolates. Herbicides were applied with a continuous belt-linked sprayer fitted with an 4Seed, V & J Seed F arms, PO. Box 82, Woodstock, IL 60098. SCorn, Pioneer Hi-Bred International, Inc., DeS Moines, IA 50301. 6BACCTO professional planting mix, Michigan Peat Co., PO. Box 98129, Houston, TX 77098. 7Activator-90, nonionic surfactant, a mixture of alkyl polyoxyethylene ether and fatty acids, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 7 t“) 8001B flat—fan nozzle8 traveling at 1.53 km h‘1 and delivering 234 L ha“ at 193 kPa of pressure. The experiment was a completely randomized design with four replications. Plants were visually evaluated 3, 7, and 14 d afier treatment (DAT). Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 indicating plant death. Evaluations represented visual stunting, chlorosis, and necrosis. Dry weight reduction was determined 14 DAT by harvesting the aboveground plant material. Dry weight reduction was calculated as 100[1 - (plant dry weight/untreated plant dry weight)]. Herbicide Retention. Experiments were conducted to determine fluthiacet and flumiclorac foliar spray retention on velvetleaf, redroot pi gweed, wild mustard, corn, and soybean using a modified Boldt and Putnam (1980) procedure. Treatments included 2 g ha’l fluthiacet or 15 g ha" flumiclorac plus 0.25% (v/v) N187 and 2.5 g L'1 Chicago Sky blue dyez. Herbicides were applied with a continuous belt-linked sprayer fitted with an 8001E flat-fan nozzle8 traveling at 1.53 km h" and delivering 234 L ha‘l at 193 kPa of pressure. At application, velvetleaf plants were 10 cm tall with five to Six leaves; redroot pigweed plants were 10 cm tall with seven to eight leaves; wild mustard plants were 8 cm tall with four to five leaves; corn plants were 20 cm tall with four leaves; and soybean plants were 13 cm tall with two trifoliolates. The experiment was a completely randomized design with four replications. Following herbicide application, aboveground plant segments were harvested and rinsed with distilled water containing 0.25% (v/v) NIS7. Plant leaf area was determined while the 8Teejet flat-fan nozzles, Spraying Systems Co., North Avenue and Schmale Road, Wheaton, IL 60532. rins rete the 1 01] are; flur stag for the Fete dur “an bro; 1h at rinsate absorbance was measured with a spectrophotometer at 625 nm. Whole plant retention was calculated from a standard curve, and results are expressed as a percent of the theoretical maximum retention. Theoretical maximum retention was calculated as 100[1 - (herbicide concentration retained/maximum retention: based on the plant leaf area)]. Herbicide Absorption, T ranslocation, and Metabolism. Experiments compared fluthiacet and flumiclorac absorption, translocation, and metabolism in velvetleaf, redroot pigweed, wild mustard, corn, and soybean. Herbicide absorption, translocation, and metabolism were determined in a Single plant treated with l4C-radiolabeled fluthiacet or flumiclorac. Plants were grown in the greenhouse as previously described to the growth stages in the spray retention experiment. The youngest fiilly developed leaf was chosen for the l‘lC-radiolabeled herbicide treatment; the 4th true velvetleaf and wild mustard leaf, the 6th true redroot pigweed leaf, the 2“d true corn leaf, and the middle soybean leaflet of the 1St trifoliolate. Velvetleaf, redroot pigweed, wild mustard, corn, and soybean plants, except the leaf chosen for 1“C treatment, were Sprayed with 2 g ha" fluthiacet or 15 g ha" flumiclorac plus 0.25% (v/v) NIS7. Herbicides were applied as previously discussed in the Spray retention experiment. The leaf chosen for 1“C treatment was covered with cellophane during the broadcast herbicide application to prevent Spray interception. The cellophane was removed immediately following herbicide application. The spray retention study determined the quantity of spray solution intercepted during a broadcast herbicide application. All hand-treated leaves received a herbicide treatment that simulated a broadcast herbicide application. To ensure sufficient radioactivity for the K I a? in: Th Pr: COIf metabolism analysis, a minimum of 2.7 x 103 Bq was applied to the treated leaf. The radiolabeled Spotting solution contained phenyl-labeled l“C-fluthiacet (1.5 x 103 kBq mg'l specific activity, 95.4% purity) or tetrahydrophthaloyl-l, 2-labeled l“C- flumiclorac (9.5 x 103 kBq mg" specific activity, 94.9% purity) with the appropriate formulation blank, NIS7, and water volumes. Treatments consisting of fifteen, 2 ul droplets of solution totaling 2.7 x 103 Bq were applied to the adaxial leaf surface. Unabsorbed l“C fluthiacet or flumiclorac was removed by gently swirling the treated leaf in a 20 ml liquid scintillation vial containing 3 ml of methanol : water (1:1) solution for 60 seconds. Leaves were rinsed with an additional 0.5 ml of solvent as they were removed fiom the scintillation vial. The rinse solution was radioassayed by liquid scintillation spectrometry (LSS). Fluthiacet and flumiclorac absorption was calculated by dividing the recovered l“C-herbicide by the quantity of I“C-herbicide applied. Radiolabeled plants were harvested 2, 4, and 12 h after treatment (HAT) and divided into three sections; the treated leaf, above the treated leaf, and below the treated leaf. These parts were immediately frozen and stored at -30 C until further analysis. Preliminary experiments found that only treated leaves contained sufficient l4C herbicide concentrations to conduct metabolism analysis; therefore, the other leaf sections were separately combusted in a biological sample oxidizer", and the evolved radiolabeled herbicide was sustained within a MC trapping cocktail. Cocktail samples were assayed with LSS to quantify herbicide translocation above and below the treated leaf. l“C translocation out of the treated leaf was calculated as the 14C recovered above and below the treated leaf divided by the total 14C recovered in the plant. 9 R. J. Harvey Instruments Corp., 123 Patterson St., Hillsdale, NJ 07642. 10 lu ml of with 00ml: u‘asc was t air st: by 21; SCpar acetic Value TLt herbl. prOCe metat ”litm- SlllCa Fluthiacet and flumiclorac metabolism was investigated in the 1“C treated leaf. Leaves were ground in a tissue homogenizerlo with 20 ml of an acetonitrile : water (6:4) solution. The homogenate was vacuum-filtered, and the residue was rinsed with an additional 20 ml of solvent. Rinsate volumes were recorded and two, 1 ml aliquots were radioassayed with LSS to determine the extractable MC. The filter paper and residue were air dried and combusted to determine the unextractable 1“C. Total radioactivity within the treated leaf was calculated by adding the extractable and unextractable l“C. The filtrate was evaporated to 2 ml with a rotary evaporator at 35 C, and the solution was transferred to a 13 by 100 mm test tube and concentrated to 100 to 150 it] under an air stream in a 40 C water bath. Fifty pl of the concentrated extract were Spotted on 20 by 20 cm Silica gel (60 F 254) thin layer chromatography (TLC) plates” for metabolite separation. Plates were developed in a 13 cm solvent front in toluene : ethyl acetate : acetic acid (5:7:1 v/v/v). Radioactive positions, proportions, and their corresponding R, values were determined by scanning TLC plates with a radiochromatogram scanner”. TLC separations revealed parent fluthiacet, flumiclorac, and three metabolites for each herbicide (Table 1). To determine metabolite biological activity, the previously discussed procedures were followed using nonradioactive herbicide treated plants. Nomadioactive metabolites were separated on the TLC plates, and their location was confirmed using ultraviolet lighting. The parent herbicides and their metabolites were scraped from the silica gel plates and placed in 13 by 100 mm test tubes. The modified Duke et al. (1984) '0 Sorvall Omni-mixer, Sorvall Inc., Newton, CT 06470. ” Whatrnan Inc., Clifton, NJ 07011. ‘2 Ambis Systems, Inc., 3939 Ruffin Road, San Diego, CA 92123. 11 was total four Stat TCVC‘ leas Her E184 and P110 herb [he 1 plan: electrolyte leakage assay procedures established biological activity of the parent herbicides and the metabolites. Fluthiacet, two fluthiacet metabolites, flumiclorac, and one flumiclorac metabolite were biologically active (data not presented). Metabolism was calculated in the treated leaf by dividing the remaining biologically active 14C by the total 1“C in the treated leaf. The experiment was a completely randomized design with four replications. Statistical Analyses All experiments were repeated over time, and data were analyzed using analysis of variance (ANOVA). Data for individual experiments were combined as analyses revealed no treatment by time interaction. Means were separated by Fisher’s protected least significant difference test (LSD) at the 5% level. RESULTS AND DISCUSSION Herbicide Effect on the Porphyrin Pathway Electrolyte Leakage. Several herbicide classes, including cyclic imides, diphenyl ethers, and oxadiazoles, initiate light-dependent chlorosis resulting from an accumulation of the photodynamic tetrapyrrole, protoporphyrin IX (Proto) (Duke et al. 1990). These herbicides also inhibit protoporphyrinogen oxidase (Protox), the last common enzyme in the heme and chlorophyll biosynthesis pathways (Duke et al. 1991). Protox iS present in plant plastids and mitochondria and catalyzes the oxidation of protoporphyrinogen IX (Protogen) to protoporphyrin IX (Proto) (Jacobs et al. 1991). Reports suggest Protox- 12 inhfi 150) 199? then OXYE cond herb rnedi dado flunt The flum; (Tabl fiudn done DAN flUrm‘. PNNO: enzm ALA 19881 acCum; a1-(195 inhibiting herbicides induce Protogen accumulation that diffuses into the cytoplasm and is oxidized to Proto by an unidentified oxidase in the plasma membrane (Jacobs et al. 1991). Once outside the normal porphyrin pathway, Proto induces the formation of membrane and chlorophyll-destroying singlet oxygen (Lydon and Duke 1988). Singlet oxygen is highly toxic to plants and results in a measurable increase in cellular conductivity. Herbicide initiated electrolyte efflux was assessed by monitoring the herbicide treated bathing medium conductivity (Duke et a1. 1984). However, the bathing medium conductivity did not increase when Protox-inhibiting herbicides were applied in darkness (Wright et al. 1995). Similarly, preliminary experiments revealed fluthiacet and flumiclorac require light to initiate herbicidal activity (data not presented). The herbicidal effects evident by electrolyte leakage from 1 HM fluthiacet and 1 aM flumiclorac on velvetleaf, redroot pigweed, corn, and soybean leaf disks were equivalent (Table 2). However, herbicidal effects on wild mustard leaf disks were greater with fluthiacet when compared with flumiclorac. One mM 4,6-dioxoheptanoic acid (DA) alone did not induce electrolyte leakage compared with an untreated control. Yet, adding DA to fluthiacet or flumiclorac reduced herbicidal activity compared with fluthiacet and flumiclorac applied without DA. Duke et al. (1991) reported that the addition of DA to Protox-inhibiting herbicides reduces their herbicidal activity by inhibiting an early enzyme in the prophyrin synthesis pathway, 5-aminolevulinic acid (ALA) dehydratase. ALA is an early intermediate in the prophyrin synthesis pathway (Lydon and Duke 1988). Exogenous ALA applications may result in herbicidal effects by initiating the accumulation of photodynamic porphyrin compounds (Lydon and Duke 1988). Wright et al. (1995) reported treating cucumber (Cueumis sativus L.) leaf disks with 50 MM ALA l3 increased redroot p: addition t and soyh. .51 ALA I redroot p; herbicidal Fluthiace Species 5 Whereas f Velvetlea fluthiacet 4). Verve reduced V' reduced it more S€ns redUCiiOn “fight by Weight re He'bl'cr'dp alleged b increased the bathing medium conductivity. However, in our experiments, velvetleaf, redroot pigweed, wild mustard, corn, and soybean leaf disks were not affected by the addition of 50 aM ALA (Table 3). Conductivity in the velvetleaf, wild mustard, corn, and soybean assay tubes was equivalent between fluthiacet and flumiclorac. Applying 50 aM ALA to fluthiacet or flumiclorac increased herbicidal activity except for fluthiacet on redroot pigweed. All data suggest fluthiacet and flumiclorac exert their light-dependent herbicidal effects by inhibiting Protox. Fluthiacet and Flumiclorac Selectivity Species Sensitivity. The field use rate for fluthiacet is 4 to 5 g ha" (Anonymous 1995), whereas flumiclorac is used at rates of 30 to 60 g ha’l (Kurtz and Pawlak 1993). Velvetleaf, redroot pigweed, wild mustard, corn, and soybean sensitivities to 2 g ha‘l fluthiacet or 15 g ha‘l flumiclorac were determined for greenhouse grown plants (Table 4). Velvetleaf was sensitive to both herbicides, as a postemergence herbicide application reduced velvetleaf dry weight by 96% (Table 4). Similarly, fluthiacet and flumiclorac reduced redroot pigweed dry weight by at least 90%. However, redroot pigweed was more sensitive to flumiclorac when compared with fluthiacet. Fluthiacet provided a 91% reduction in wild mustard dry weight, yet flumiclorac only reduced wild mustard dry weight by 53%. Corn and soybean were tolerant to fluthiacet and flumiclorac as dry weight reduction was less than 5%. Herbicide Retention. Species susceptibility to a postemergence herbicide application is affected by herbicide retention (Gillespie 1994). Sprague et al. (1997) reported a fivefold increase in isoxaflutole (5-cyclopropyl isoxazol-4-yl-2-mesyl-4-trifluoromethylphenyl l4 ketone) retention when metolachlor/benoxacor (2-chloro-N-(2-ethyl-6-methylphenyl)-‘(2- methoxy-l -methylethyl)acetamide/(4-dichloroacetyl)-3 ,1dihydro-3-methyl-2H-l ,4- benzoxazine) was added which resulted in enhanced corn injury compared with isoxaflutole alone. Fluthiacet and flumiclorac retention on leaves varied among test species with the greatest differences occurring between the crop and weed species (Table 5). Fluthiacet and flumiclorac retention by redroot pigweed was eightfold greater than soybean. Thus, for each square leaf area unit, eight times more herbicide was present on a redroot pigweed leaf than a soybean leaf. Velvetleaf and wild mustard retained less fluthiacet and flumiclorac than redroot pigweed; however, herbicide retention by these species was twice that of corn or soybean. Differences in redroot pigweed and soybean epicuticular wax structure could explain differences in herbicide retention of these species. Harr et al. (1991) reported 54 and 75° leaf contact angles for redroot pigweed and soybean, respectively, confirming differences in the epicuticular wax of these two Species. Herbicide Absorption. Fluthiacet and flumiclorac both provide excellent postemergence velvetleaf control (Table 4). However, fluthiacet absorption by velvetleaf foliage was greater than flumiclorac 12 HAT (Table 6). Although soybean is tolerant to both herbicides, foliar absorption of fluthiacet and flumiclorac was greater in soybean than velvetleaf. However, corn absorbed less fluthiacet than velvetleaf. Fluthiacet absorption was greater by redroot pigweed, wild mustard, and corn when compared with absorption of flumiclorac 12 HAT. Increased fluthiacet absorption in wild mustard may explain greater sensitivity of wild mustard to fluthiacet than flumiclorac. However, redroot pigweed absorbed more fluthiacet than flumiclorac, yet 15 redroot pigweed is more tolerant of fluthiacet than flumiclorac. Corn is equally sensitive to both herbicides; and fluthiacet and flumiclorac foliar absorption was Similar in corn 2 HAT. Foliar absorption of fluthiacet and flumiclorac alone cannot account for differences in herbicide sensitivity or selectivity. Herbicide T ranslocation. Protox-inhibiting herbicides are regarded as contact herbicides because of limited translocation (Scalla and Matringe 1994). F luthiacet and flumiclorac movement within plants was evaluated by measuring l“C translocation out of the l"C treated leaf. Herbicide translocation was limited as less than 29% of the MC herbicide was translocated out of the treated leaves (Table 6). Relative herbicide translocation did not vary between species and herbicides 2 and 12 HAT. This was not surprising Since herbicidal injury symptoms from fluthiacet or flumiclorac were present within 3 h after treatment (data not presented). Differences in species sensitivity to fluthiacet and flumiclorac are not explained by differential herbicide translocation. Translocation of fluthiacet and flumiclorac 12 HAT was greater in wild mustard and corn compared with velvetleaf. However, translocation did not correlate with fluthiacet and flumiclorac selectivity. Wild mustard is tolerant to flumiclorac yet susceptible to fluthiacet, while corn is tolerant to both herbicides (Table 4). Fluthiacet and flumiclorac tolerant Species translocated similar or greater amounts of herbicide compared with plants susceptible to these herbicides. Thus, herbicide translocation did not appear to contribute to fluthiacet or flumiclorac selectivity. Herbicide Metabolism. Research evaluated differences in fluthiacet and flumiclorac metabolism to a nonbiologically active metabolite. Although both herbicides were metabolized, the structural characterization of these metabolites was beyond the scope of 16 this study. Velvetleaf, redroot pigweed, and corn metabolized more fluthiacet than flumiclorac 12 HAT to nonbiologically active metabolites (Table 6). However, redroot pigweed was the only species more sensitive to flumiclorac than fluthiacet. Fluthiacet metabolism to a nonbiologically active metabolite was greater in redroot pi gweed, corn, and soybean 12 HAT when compared with velvetleaf and wild mustard (Table 6). Metabolism results support the species sensitivity experiment where redroot pigweed, corn, and soybean were more tolerant to fluthiacet than velvetleaf (Table 4). Likewise, there were more of the biologically active forms of flumiclorac present in the most sensitive Species, velvetleaf and redroot pigweed. Flumiclorac metabolism to a nonactive form was greater in wild mustard, corn, and soybean than velvetleaf and redroot pigweed. Fluthiacet and flumiclorac tolerant species metabolize these herbicides more rapidly than sensitive species. Fluthiacet and flumiclorac exert their light-dependent herbicidal effects by inhibiting Protox. However, the selectivity mechanisms plants use to protect against these herbicides varies by species. Table 7 identifies the factors that Si gnificantly contribute to species tolerance to these herbicides when compared with velvetleaf. Differential herbicide metabolism and differential foliar herbicide retention, absorption, and translocation contribute to fluthiacet and flumiclorac selectivity. However, the differences in foliar absorption and metabolism in wild mustard treated with fluthiacet compared with flumiclorac does not account for the dramatic differences in the whole plant sensitivity to these herbicides. Sherman et al. (1991) reported that mustard, which is tolerant to acifluorfen, produced limited Proto in response to acifluorfen despite having 17 susceptible Protox. Jacobs et al. (1990) reported tolerant soybean root mitochondria are insensitive to acifluorfen, thus suggesting acifluorfen selectivity may be explained by differences in Protox sensitivity. However, further investigations by Sherman et al. (1991) found no correlation between Protox sensitivity and herbicidal effects from acifluorfen. Thus, species selectivity to Protox-inhibiting herbicides may be explained by less Proto accumulation, decreased absorption, increased translocation, rapid metabolism, and other mechanisms; but apparently, it is not due to differences in Protox sensitivity (Scalla and Matringe 1994). Another explanation for tolerance to Protox-inhibiting herbicides is an enhanced capacity to detoxify singlet oxygen. Plants contain natural defense mechanisms that provide protection from damaging oxygen radicals. The reductant, ascorbate, is one such molecule. Sandmann and Boger (1990) reported fifteenfold greater ascorbate levels in Protox-inhibiting herbicide tolerant Bumilleriopsis microalgae when compared with susceptible Scendesmus. Similarly, tobacco (Nicotiana tabacum L.)) susceptibility to flumiclorac and acifluorfen was attributed to an enhanced antioxidant system in tolerant biotypes (Gullner et al. 1991). Antioxidant systems that can protect plants from Protox- inhibiting herbicides are one selectivity mechanism. However, their impact on Protox- inhibiting herbicide efficacy is unclear. Plant tolerance to Protox-inhibiting herbicides is a complex process, and factors not examined in these experiments may contribute to fluthiacet and flumiclorac selectivity. A complex interaction of factors including herbicide retention, absorption, translocation, and metabolism ultimately determine Species sensitivity to a particular Protox-inhibiting herbicide. 18 ACKNOWLEDGMENTS The authors thank Jason Simon for his assistance in this research. Appreciation is extended to Valent U.S.A. Corporation and Novartis Crop Protection, Inc. for their financial support. 19 10. 11. 12. LITERATURE CITED Anonymous. 1995. Fluthiacet herbicide technical information bulletin. Greensboro, NC: CIBA-GEIGY Corp., Agricultural Division. Boldt, P. F. and A. R. Putnam. 1980. Selectivity mechanisms for foliar applications of diclofop-methyl. I. Retention, absorption, translocation, and volatility. Weed Sci. 28:474-477. Coupland, D. 1983. Influence of light, temperature and humidity on the translocation and activity of glyphosate in Elymus repens (=Agropyron repens). Weed Res. 23:347-355. Doran, D. L. and R. N. Andersen. 1976. Effectiveness of bentazon applied at various times of day. Weed Sci. 24:567-570. Duke, S. O., J. M. Becerril, T. D. Sherman, J. Lydon, and H. Matsumoto. 1990. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci. 30:367-378. Duke, S. O., J. Lydon, J. M. Becerril, T. D. Sherman, L. P. Lehnen, Jr., and H. Matsumoto. 1991. Protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 39:465-473. Duke, S. O., K. C. Vaughn, and R. L. Meeusen. 1984. Mitochondrial involvement in the mode of action of acifluorfen. Pestic. Biochem. Physiol. 21:368-373. Gillespie, G. R. 1994. 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Absorption, translocation, and metabolism of acifluorfen and lactofen in pitted momingglory(1pomoea lacunosa) and ivyleaf momingglory (Ipomoea hederacea). Weed Sci. 36:141-145. Jacobs, J. M., N. J. Jacobs, T. D. Sherman, and S. 0. Duke. 1991. Effect of diphenyl ether herbicides on oxidation of protoporphyrinogen to protoporphyrin in organellar and plasma membrane enriched fractions of barley. Plant Physiol. 97: 197-203. Jacobs, J. M., N. J. Jacobs, S. F. Borotz, and M. L. Guerinot. 1990. Effects of photobleaching herbicide, acifluorfen-methyl, on protoporphyrinogen oxidation in barley organelles, soybean root mitochondria, soybean root nodules, and bacteria. Arch. Biochem. Biophys. 280:369-375. Kamoshita, K., E. Nagano, S. Hashimoto, R. Sato, R. Yoshida, and H. Oshio. 1993. V-23031-A new herbicide for postemergence weed control in soybeans and field corn. Abstr. Weed Sci. Soc. Am. 53:3. Kells, J. J ., W. F. Meggitt, and D. Penner. 1984. Absorption, translocation, and activity of fluazifop-butyl as influenced by plant growth stage and environment. Weed Sci. 32:143-149. King, C. A. and L. R. Oliver. 1992. Application rate and timing of acifluorfen, bentazon, chlorimuron, and imazaquin. Weed Technol. 6:526-534. Kurtz, A. R. and J. A. Pawlak. 1993. V-23031-A new postemergence herbicide for use in field corn. Abstr. Weed Sci. Soc. Am. 53:9. Lydon J. and S. 0. Duke. 1988. Porphyrin synthesis is required for photobleaching activity of the p-nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol. 31:74-83. Mito, N., R. Sato, M. Miyakado, H. Oshio, and S. Tanaka. 1991. In vitro mode of action of N-Phenylimide photobleaching herbicides. Pestic. Biochem. Physiol. 40:128-135. Porpiglia, P. J ., E. R. Hill, and A. Tally. 1994. CGA-248757 for postemergence broadleaf weed control in corn (Zea mays L.) and soybeans (Glycine max (L.) Merr.). Abstr. Weed Sci. Soc. Am. 34:2. Ritter, R. L. and H. D. Coble. 1981. Penetration, translocation, and metabolism of acifluorfen in soybean (Glycine max), common ragweed (Ambrosia artemisiifolia), and common cocklebur (Xanthium pensylvanicum). Weed Sci. 29:474-480. 21 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. Roggenbuck, F. C., L. Rowe, D. Penner, L. Petroff, and R. Burrow. 1990. Increasing postemergence herbicide efficacy and rainfastness with Silicone adjuvants. Weed Technol. 4:576-580. Sandmann, G. and P. Bbger. 1990. Peroxidizing herbicides: Some aspects on tolerance. American Chemical Society Symposium series No. 421: Washington DC, pp. 407-418. Sato, R., H. Oshio, H. Koike, Y. Inoue, S. Yoshida, and N. Takahashi. 1991. Specific binding of protoporphyrin IX to membrane-bound 63 kilodalton polypeptide in cucumber cotyledons treated with diphenyl ether-type herbicides. Plant Physiol. 96:432-437. Scalla R. and M. Matringe. 1994. Inhibitors of protoporphyrinogen oxidase as herbicides: Diphenyl ethers and related photobleaching molecules. Rev. Weed Sci. 62103-132. Sherman, T. D., J. M. Becerril, H. Matsurnoto, M. V. Duke, J. M. Jacobs, N. J. Jacobs, and S. 0. Duke. 1991. Physiological basis for differential sensitivities of plant Species to protoporphyrinogen oxidase-inhibiting herbicides. Plant Physiol. 97:280-287. Sprague, C. L., J. J. Kells, and D. Penner. 1997. Weed control and corn tolerance as affected by the timing of isoxaflutole application. Proc. N. Cent. Weed Sci. Soc. 52:65. Starke, R. J ., K. A. Renner, D. Penner, and F. C. Roggenbuck. 1996. Influence of adj uvants and desmedipham plus phenmedipham on velvetleaf (Abutilon theophrasti) and sugarbeet response to triflusulfiiron. Wed Sci. 44:489-495. Westberg D. E. and H. D. Coble. 1992. Effect of acifluorfen on the absorption, translocation, and metabolism of chlorimuron in certain weeds. Weed Technol. 6:4-12. Wichert, R. A. and R. E. Talbert. 1993. Soybean [Glycine max (L.)] response to lactofen. Weed Sci. 41:23-27. Wright, T. R., E. P. Fuerst, A. G. Ogg, Jr.,U. B. Nandihalli, and H. J. Lee. 1995. Herbicidal activity of UCC-C4243 and acifluorfen is due to inhibition of protoporphyrinogen oxidase. Weed Sci. 43:47-54. 22 Table 1. Characterization of fluthiacet and flumiclorac metabolites.a Herbicide Metabolite Rf Biologically activeb Fluthiacet Parent 0.75 Yes A 0.52 Yes B 0.3 1 Yes C 0. 1 3 No Flumiclorac Parent 0.88 Yes A 0.44 Yes B 0.27 No C O. 1 3 No ‘ Quantified parent herbicide and metabolites from Thin Layer Chromatography (TLC) separation using 20 by 20 cm Silica gel (60 F 254) TLC plates. Plates were developed in a 13 cm solvent front in toluene : ethyl acetate : acetic acid (5:7:1 v/v/v). b Electrolyte leakage assay indicated biological activity equivalent to the parent herbicide. 23 Table 2. Effect of 4,6-dioxoheptanoic acid (DA) on electrolyte leakage 24 h after fluthiacet and flumiclorac treatment.a Species Redroot Wild Treatment Rate Velvetleaf pigweed mustard Corn Soybean aM —— amhos" cm" assay tube" Fluthiacet 1 194 144 291 73 255 Flumiclorac 1 181 139 208 75 213 DA 1000 3 28 2 4 11 Fluthiacet + DA 1000 + 1 56 9 89 33 166 F lumiclorac + DA 1000 + 1 82 3O 74 36 155 LSD (0.05) 43 ‘ Means may be compared within or across columns within herbicides and within Species. 24 Table 3. Effect of 6-aminolevulinic acid (ALA) on electrolyte leakage 24 h afier fluthiacet and flumiclorac treatment.al Species Redroot Wild Treatment Rate Velvetleaf pigweed mustard Corn Soybean aM amhos" cm" assay tube" Fluthiacet 0.2 155 171 175 73 138 Flumiclorac 0.2 126 129 144 42 157 ALA 50 27 9 15 4 3 Fluthiacet + ALA 0.2 +50 206 182 226 127 201 Flumiclorac + ALA 0.2 + 50 210 196 240 94 229 LSD (0.05) 41 “ Means may be compared within or across columns within herbicides and within Species. 25 Table 4. Species sensitivity to 2 g ha" fluthiacet and 15 g ha" flumiclorac in the greenhouse 14 d after treatment.“ Herbicide Species Fluthiacet Flumiclorac % dry weight reduction Velvetleaf 96 a 96 a Redroot pigweed 90 b 97 a Wild mustard 91 b 53 0 Corn 5 d 2 d Soybean 5 d 5 d ‘ Means may be compared within or across columns within herbicides and within species. Means followed by the same letter are not significantly different according to Fisher’s Protected LSD (or= 0.05). All treatments included nonionic surfactant at 0.25% v/v. 26 Table 5. F luthiacet and flumiclorac retention in five plant species.“ Herbicide Species Fluthiacet Flumiclorac % of theoretical maximum retention Velvetleaf 45 c 42 c Redroot pigweed 78 a 66 b Wild mustard 37 c 42 c Corn 17 d 17 d Soybean 8 d 8 d " Means may be compared within or across columns within herbicides and within species. Means followed by the same letter are not significantly different according to Fisher’s Protected LSD (th= 0.05). All treatments included nonionic surfactant at 0.25% WV. 27 Table 6. Fluthiacet and flumiclorac absorption, translocation, and metabolism in 5 plant species.ll Harvest time 12 h Species F luthiacet Flumiclorac Fluthiacet Flumiclorac Foliar absorption % of applied l"C Velvetleaf 64 c 44 d 81 c 56 f Redroot pigweed 79 a 42 d 93 a 66 e Wild mustard 79 a 68 be 95 a 85 bc Corn 50 d 43 d 73 d 60 f Soybean 75 ab 70 abc 90 ab 87 b Translocationb % of applied l“C Velvetleaf 99 a 99 a 96 a 98 a Redroot pigweed 96 ab 86 b 98 a 92 ab Wild mustard 89 ab 90 ab 82 be 84 b Corn 76 c 74 c 73 c 71 c Soybean 99 a 99 a 96 a 99 a Metabolismc % of applied 1“C Velvetleaf 83 a 77 ab 49 be 63 a Redroot pigweed 68 b 70 b 35 de 54 ab Wild mustard 80 ab 72 ab 39 cde 46 bed Corn 78 ab 46 c 36 de 30 e Soybean 40 c 72 ab 15 f 40 cde “ Means may be compared within or across columns within factors and within harvest time. Means followed by the same letter are not Significantly different according to Fisher’s Protected LSD (or = 0.05). b Radioactive herbicide remaining in the treated leaf. ° Metabolism expressed as percentage remaining biologically active within the treated leaf. 28 1a 116 Table 7. Factors affecting plant tolerance to fluthiacet and flumiclorac 12 h after treatment.3 Herbicide Herbicide Species Toleranceb Retention Absorption Translocation Metabolism Fluthiacet velvetleaf S — — _ _ redroot S _ _ _ X pigweed wild mustard S X corn T X X X X soybean T X — _ X Flumiclorac velvetleaf S — — ._ _ redroot . S — —— _ _ pigweed wrld ST __ _ X X mustard corn T X — X X soybean T X — _ X ‘X = significantly contributes, — = does not significantly contribute to Species tolerance. b S= sensitive, T= tolerant based on Table 4. 29 CHAPTER 2 Environmental Effects on Fluthiacet and Flumiclorac Efficacy and Soybean Tolerance ABSTRACT Laboratory and field experiments were designed to examine the effect temperature, light intensity, time to initial light exposure, relative humidity, and the presence of dew had on fluthiacet and flumiclorac efficacy. Increasing temperature fiom 10 to 40 C and light intensity fiom 0 to 1000 mm] m‘2 S" increased fluthiacet and flumiclorac activity on redroot pigweed and common lambsquarters. Time to initial light exposure and relative humidity did not affect fluthiacet and flumiclorac activity on redroot pigweed and common lambsquarters. The presence of dew reduced herbicide activity on redroot pigweed and common lambsquarters. A field study was conducted to determine if fluthiacet or fltuniclorac applications at 0600 h, 1400 h, or 2200 h influenced soybean tolerance and weed control. The greatest soybean injury occurred from fluthiacet or flumiclorac applications at 0600 h compared with 1400 or 2200 h. Common lambsquarters control was greatest when fluthiacet or flumiclorac was applied at 0600 h or 1400 h compared with 2200 h. However, redroot pigweed control was greatest when fluthiacet or flumiclorac was applied at 1400 h. Application time of day did not effect 30 velvetleaf control with either herbicide. Results suggest environmental conditions at application influence soybean tolerance and weed control with fluthiacet and flumiclorac. Nomenclature: F luthiacet, [[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H- [1 ,3 ,4]thiadiazolo[3 ,4-a]pyridazin— 1 -ylidene)amino]phenyl]thio]aceate; flumiclorac, pentyl[2-chloro-4-fluoro-5-(1 ,3,4,5 ,6,7-hexahydro-1 ,3-dioxo-2H-isoindol-2- yl)phenoxy]acetic acid; common lambsquarters, Chenopodium album L. #‘ CHEAL; redroot pigweed, Amaranthus retroflexus # AMARE; velvetleaf, Abutilon theophrasti Medik. # ABUTH; soybean Glycine max (L.) Merr. ‘Conrad’ # GLYMA. Key Words: Application time of day, temperature, relative humidity, light intensity, dew, CHEAL, AMARE, ABUTH, GLYMA. Abbreviations: COC, crop oil concentrate; DAT days after treatment; HAT, hours after treatment; NTS, nonionic surfactant; Protox, protoporphyrinogen oxidase; UAN, 28% urea ammonium nitrate; v/v, volume per volume. 'Letters following this symbol are a WSSA-approved computer code from Composite List of Weed, Revised 1989. Available from WSSA. 31 INTRODUCTION Environmental conditions at application such as temperature, light, relative humidity, rainfall, and soil moisture influence herbicide efficacy (Coupland 1983; Kudsk et al. 1990). Because environmental conditions vary within the day, application time may influence the herbicidal activity of cyclic imide herbicides such as fluthiacet and flumiclorac. Several classes of photodynamic herbicides including cyclic imides, diphenyl ethers, and oxadiazoles block the enzymatic oxidation of protoporphyrinogen IX to protoporphyrin IX by protoporphyrinogen oxidase (Protox) (Duke et al. 1991). Protoporphyrin IX rapidly generates singlet oxygen in the presence of light and molecular oxygen, subsequently causing lipid peroxidation and immediate cellular death in sensitive plant species (Lee and Duke 1994). Research investigating environmental effects on soybean tolerance and efficacy of photodynamic herbicides is limited. Common cocklebur (Xanthium strumarium L.) and velvetleaf control with bentazon (3-(l-methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)- one 2,2-dioxide) were reduced when bentazon was applied early morning, late evening, or at night (Doran and Anderson 1976). Paraquat (l ,1'-dimethyl-4,4'-bipyridinium ion) provided greater quackgrass (Elyitrigia repens L.) control when applied at 2000 h compared with an application at 1400 h (Putnam and Ries 1968). Yet, common lambsquarters and redroot pigweed control with paraquat and acifluorfen (5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoic acid) increased when applied at 0900 h or 1500 h compared with 0300 h or 2100 h (Zhou and Ahrens 1995). Hemp sesbania (Sesbania 32 exaltata (Raf) Cory) control with acifluorfen increased when applied at 2100 h compared with 0600 h or 1200 h (Lee and Oliver 1982). Temperature and relative humidity influence the translocation and efficacy of diphenyl ether herbicides. Acifluorfen translocation in showy crotalaria (Crotalaria spectabilis Roth) increased fourfold when relative humidity increased from 40 to 100% (Wills and McWhorter 1981). Common cocklebur and common ragweed (Ambrosia artemisiifolia L.) control with acifluorfen was 10 to 30% greater when acifluorfen was applied at 85% relative humidity compared with 50% relative humidity (Ritter and Coble 1981). Similarly, increasing relative humidity from 50 to 85% enhanced acifluorfen, fomesafen (5-[2-chloro-4-(trifluoromethyl)phenoxy](methylsulfonyl)-2-nitrobenzamide), and lactofen ((:)-2-ethoxy- l -methyl-2-oxoethyl-5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoate) activity on prickly Sida (Sida spinosa L.), pitted momingglory, (Ipomoea lacunosa L.), entireleaf momingglory (Ipomoea hederacea var. integriuscula L.), and common cocklebur (Wichert et al. 1992). Inconsistent weed control with flumiclorac was reported in 1995 (K. A. Renner, personal communication). The effect environmental conditions have on soybean tolerance and weed control with fluthiacet or flumiclorac has not been documented. Therefore, the objectives of this research were to evaluate the effect temperature, light intensity, time to initial light exposure, relative humidity, the presence of dew, and the application time of day has on fluthiacet or flumiclorac efficacy and soybean tolerance. 33 MATERIALS AND METHODS General methods for laboratory experiments. Experiments were conducted to determine the effect temperature, light intensity, time to initial light exposure, and relative humidity have on fluthiacet and flumiclorac efficacy. Uniform, fully expanded leaves from natural populations of field-grown common lambsquarters and redroot pigweed were harvested at the Michigan State University Research Farm in East Lansing, MI, in August 1998. Leaf sections of 1.5 by 1.5 cm were excised and placed in 20 by lOO-mm petri dishes containing No. 2 Whatrnan filter paper2 and 5 ml of distilled water. Distilled water was added throughout the experiment to maintain leaf turgor. Herbicide application consisted of five, 1 ul droplets of solution applied to the adaxial leaf surface. Treatments included 4 g ha" fluthiacet, 30 g ha" flumiclorac, and an untreated control. Herbicide treatments were applied with 0.25% (v/v) nonionic surfactant3 (NIS). F luthiacet and flumiclorac activity on common lambsquarters and redroot pigweed leaf sections were visually evaluated 72 h after treatment (HAT). Visual ratings were based on a scale from 0 (no effect) to 100% (complete dessication). Values represent leaf discoloration and necrosis. Each experiment was a completely randomized design with Six replications. Experiments were conducted twice, and the data presented are the means of the two experiments. Unless otherwise indicated, the following conditions were standardized: 2Filter paper, Whatrnan #2. Whatman International Ltd., Maidstone, England. 3Activator-90, nonionic surfactant, a mixture of alkyl polyoxyethylene ether and fatty acids. Loveland Industries, Inc., PO. Box 1289, Greeley, CO 80632. 34 temperature at 30 C, 24-h illumination at 40 amol m’2 s", and 6 leaf sections per treatment. Temperature. Petri dishes containing hydrated leaf sections were placed in water baths calibrated to 10, 20, 30, or 40 C. Leaf sections were equilibrated to the water temperature for 45 min before herbicide application. Light intensity. Light intensity was examined by comparing herbicidal activity on hydrated leaf sections exposed to 0, 4, 40, or 1,000 amol In2 S" for 72 h. Time to initial light exposure. Leaf sections were equilibrated for l h at 30 C in darkness before herbicide application. Leaf sections were removed from darkness at 0, 2, 4, 6, 8, or 12 HAT and exposed to 24-h illumination at 40 amol rn'2 3". Relative humidity. A continuous flow system consisting of a vapor generator and three 9.3 L glass chambers connected with 3 mm id. teflon tubing was designed. In-line microbial filters4 filtered incoming air. Flow rate of 150 ml per min was regulated with glass microbore capillary tubes and a pressure regulators. Humidity was established within the chambers by directing air flow through 1) sterilized water (90% relative humidity), 2) saturated calcium nitrate solution (50% relative humidity), or 3) by directly transferring air into the chamber (10% relative humidity). The glass chambers were equilibrated for 24 h before leaf sections were treated with herbicide. Treated leaf sections were placed in the chambers for 8 h and exposed to 4 amol rn‘2 5". Leaf sections were removed from the glass chambers and exposed to 40 amol m2 s" for 64 h. 4Microbial filter, Alltech Associates, Inc., Deerfield, IL 60015. 5Scientific pressure regulator, South Plainfield, NJ 07080. 35 Influence of dew on efficacy. Experiments were conducted at the Michigan State University Research Farm in East Lansing, MI, in 1998. Locally collected common lambsquarters and redroot pigweed seeds were planted in BACCTO" potting soil in 946- ml plastic pots. Initial environmental conditions were maintained within a greenhouse at 27 d: 5 C. Following emergence, seedlings were transferred to outdoor environmental conditions. Plants were thinned to 1 plant pot", fertilized with 50 ml of a water—soluble fertilizer solution (400 ppm N, 400 ppm P205, and 400 ppm K20), and watered as needed. Plants were split into two groups the evening prior to herbicide application, dew or no dew. Dew designated plants were left uncovered while the no dew plants were loosely covered with burlap to inhibit natural dew formation. Plants were treated with fluthiacet or flumiclorac 30 min after burlap removal. The experiment was a completely randomized design with four replications. Treatments included 4 g ha" fluthiacet, 30 g ha" flumiclorac, and an untreated control. All treatments were applied in combination with 0.25% (v/v) NIS. Herbicides were applied on July 4, 1998 and July 6, 1998 with a carbon dioxide backpack sprayer traveling at 6.3 km h" and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles7 spaced 51 cm apart and 48 cm above the canopy. At application, common lambsquarters plants were 1 to 6 cm tall with two to ten leaves; and redroot pigweed plants were 1 to 10 cm tall with two to twelve leaves. 6BACCTO professional planting mix, Michigan Peat Co., Houston, TX 77098. 7Teejet flat-fan tips, Spraying Systems Co., North Avenue and Schmale Road, Wheaton, IL 60188. 36 Common lambsquarters and redroot pigweed control was visually evaluated for phytotoxicity 7 and 14 d after treatment (DAT). Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 indicating plant death. Evaluations represented visual stunting, chlorosis, and necrosis. Field experiment. Experiments were conducted at the Michigan State University Research Farm at East Lansing, MI, in 1996 and 1998 and at the Michigan State University Horticulture Research Station at Clarksville, MI, in 1997. The East Lansing soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aerie Ochraqualfs) with 3.3 and 2.2% organic matter in 1996 and 1998, respectively. The Clarksville soil was a Lapeer sandy loam (coarse-loamy, mixed, mesic Mollic Haplaquepts) with 1.9% organic matter. The soil pH was 7.0, 6.8, and 7.1 in 1996, 1997, and 1998, respectively. The 1996 and 1998 Sites were fall chisel plowed with secondary tillage consisting of two field cultivations at planting. The 1997 Site was spring moldboard plowed, and secondary tillage consisted of two field cultivations at planting. ‘Conrad’ soybean was planted in 76-cm rows at 395,000 seed ha". Plots were 3 m wide by 9.1 m in length. The experimental design was a split plot with four replications. Main plots were herbicide. Subplots were time of application. Main plots included either 4 g ha" fluthiacet or 30 g ha" flumiclorac. Each herbicide treatment was applied within a 24 h time period at 0600 h, 1400 h, and 2200 h (Table 6). All treatments included either 0.25% (v/v) NIS plus 1.0% (v/v) 28% urea ammonium nitrate (UAN) or 0.5% (v/v) crop oil concentrate8 (COC). 8Herbirnax, crop oil concentrate, 83% petroleum oil, 17% surfactant, Loveland Industries, Inc., PO. Box 1289, Greeley, CO 80632. 37 Herbicides were applied June 13, 1996, June 24, 1997, and June 9, 1998, 26, 31, and 27 d after planting, with a compressed air tractor-mounted sprayer traveling at 6.3 km h" and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat- fan nozzles Spaced 51 cm apart and 48 cm above the weed canopy. At application, soybean plants were 10 to 12 cm tall with two fully developed trifoliolates, common lambsquarters plants were 1 to 10 cm tall with 2 to 24 leaves, redroot pigweed plants were 1 to 10 cm tall with 2 to 12 leaves, and velvetleaf plants were 1 to 10 cm tall with l to 7 leaves. Soybean injury was visually evaluated 3, 7, l4, and 21 DAT. Weed control was evaluated for each Species 7, 14, and 21 DAT. Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 signifying plant death. Soybean injury and weed control evaluations represent visual stunting, chlorosis, and necrosis. Statistical analyses. All experiments were repeated over time, and data were analyzed using analysis of variance (ANOVA). Data for individual experiments were combined as analyses revealed no treatment by time interaction. Means were separated by Fisher’s protected least significant difference (LSD) at the 5% level. RESULTS AND DISCUSSION Laboratory experiments. Temperature. F luthiacet and flumiclorac activity on common lambsquarters increased four and sevenfold, respectively, when temperature increased from 10 to 40 C (Table 1). Similarly, when temperature increased from 10 to 40 C, activity of both herbicides increased threefold on redroot pigweed. However, fluthiacet and flumiclorac activity on 38 x _2. redroot pigweed increased, while activity on common lambsquarters did not increase when temperature increased from 30 to 40 C. Eckl and Gruler (1980) found species dependent phase changes in plant cuticles were associated with changes in temperature. The composition and structure of epicuticular wax affects herbicide efficacy (Flore and Bukovac 197 8). Harr et a1. (1991) reported nonpolar fractions of common lambsquarters and redroot pigweed cuticles were 30 and 42%, respectively, confirming natural differences exist in the epicuticular wax of these species. Differences in phase changes or the epicuticular wax structure of common lambsquarters and redroot pigweed cuticles may explain differences in herbicidal response of these weed species at 30 and 40 C. Light intensity. Increasing light intensity from 4 to 1,000 amol m'2 5" increased fluthiacet and flurrriclorac activity on common lambsquarters and redroot pigweed 4 to 15 fold (Table 2). Light and molecular oxygen combine with protoporphyrin IX to generate Singlet oxygen, which initiates lipid peroxidation and cellular death in Protox susceptible plant species (Lee and Duke 1994). Thus, increased herbicidal activity on common lambsquarters and redroot pigweed was observed with increasing light intensity. Time to initial light exposure. Time to initial light exposure did not affect fluthiacet and flumiclorac activity on common lambsquarters or redroot pigweed 72 HAT (Table 3). Fluthiacet and flumiclorac activity is evident within 3 h after application if light is present at application (data not presented). Thus, the mechanism of fluthiacet or flumiclorac selectivity must occur rapidly in tolerant Species. Ritter and Coble (1981) reported that soybean tolerance to acifluorfen was explained by less rapid herbicide penetration and translocation coupled with increased metabolism rates. Less rapid absorption and 39 decreased translocation rates of fluthiacet and flumiclorac may account for differences in herbicidal response of common lambsquarters and redroot pigweed. Relative humidity. Increased relative humidity can enhance herbicidal activity by prolonging the drying time and increasing cuticle hydration (Caseley 1989; Ritter and Coble 1981). Wichert et al. (1992) reported increased relative humidity enhanced Protox- inhibiting herbicide activity on prickly Sida, pitted and entireleaf momingglory, and common cocklebur. In our research, increased relative humidity prolonged drying time (personal observation), but did not affect fluthiacet or flumiclorac activity on common lambsquarters and redroot pigweed 72 HAT (Table 4). The lack of response to relative humidity may result from factors such as temperature and light masking the subtle effects of relative humidity. Influence of dew on efficacy. The presence of dew at application may increase or decrease herbicide performance depending upon the herbicide and species involved (Caseley 1989; Wanamarta and Penner 1989). The presence of dew at application reduced common lambsquarters and redroot pigweed control with fluthiacet or flumiclorac l4 DAT (Table 5). Field experiment. Preliminary experiments revealed soybean tolerance and weed control with lactofen, oxasulfuron, and tank mixtures of lactofen or oxasulfuron with fluthiacet or flumiclorac were unaffected by application time of day (data not presented). However, application time of day affected soybean tolerance and weed control with fluthiacet or flumiclorac applied alone (Table 7). Soybean injury was greatest 7 DAT for both herbicides applied at 0600 h (Table 7). Fluthiacet or flumiclorac applied at 0600 h and 1400 h provided greater common 40 lambsquarters control compared with herbicides applied at 2200 h (Table 7). Either herbicide applied at 1400 h provided greater redroot pigweed control compared with applications at 0600 h or 2200 h. Velvetleaf control 14 DAT with fluthiacet or flumiclorac was unaffected by application time of day (Table 7). Fluthiacet or flumiclorac applied at 1400 h provided the greatest broad-spectrum broadleaf weed control. At 1400 h, air temperature and light intensity in the field were greatest (Table 6). Interestingly, soybean injury did not increase with increasing temperature or light intensity. Therefore, soybean tolerance to fluthiacet and flumiclorac must be influenced by other factors. Common lambsquarters and redroot pigweed control decreased in the field when initial light exposure occurred 8 h after fluthiacet or flumiclorac applications. Laboratory experiments suggest reduced weed control with evening applications of fluthiacet or flumiclorac is not related to a delay in light exposure. However, laboratory experiments were conducted at 30 C, whereas the air temperature in the field was 526 C and decreased following herbicide application (Table 6). Thus, at low temperatures time to initial light exposure may influence fluthiacet or flumiclorac activity. Dew was only present at 0600 h in 1996 (Table 6), and weed control was not reduced compared with other years (data not presented). Herbicide absorption is a complex process with no single controlling factor. Spray solution, plant foliage, and environmental conditions before, at, and following application determine herbicide response (Holen and Dexter 1993; Wanamarta and Penner 1989). Leaf movements have important implications on herbicide efficacy (Anderson and Koukkari 1979). Rhythmic leaf movements allow leaves to maximize the capture of light (Akey et al. 1990). Daily leaf oscillations in velvetleaf account for decreased velvetleaf 41 control with bentazon by reducing spray interception when leaves are positioned vertically (Anderson and Koukkari 1978; Doran and Anderson 1979). However, Koukkari and Johnson (1979) reported the physical orientation of velvetleaf leaves did not affect bentazon retention, thus concluding plant susceptibility was due to diurnal changes in the plants physiological ability to detoxify the herbicide. Similarly, velvetleaf control with fluthiacet or flumiclorac did not decrease at 2200 h although the leaves had a vertical orientation. Weaver and Nylund (1963) reported increased carbohydrate concentrations at application were associated with the susceptibility of field pea to MCPA (2-methyl-4-chlorophenoxyacetic acid). These aspects and others ultimately combine to influence herbicide tolerance and efficacy in the field. Laboratory results suggest a herbicide application at high temperature, high light intensity, and in the absence of dew would increase fluthiacet or flumiclorac activity on common lambsquarters and redroot pigweed. Field studies confirmed these observations for redroot pigweed as maximum control was obtained from an application of fluthiacet or flumiclorac at 1400 h. The greatest common lambsquarters control in the field was achieved with fluthiacet or flumiclorac applications at 0600 h or 1400 h. Equivalent common lambsquarters susceptibility to fluthiacet or flumiclorac applied in the field early morning and afiemoon illustrates the complex nature of herbicide selectivity. A reduction in herbicide retention or absorption may not be relevant for velvetleaf control with fluthiacet or flumiclorac because of high velvetleaf sensitivity to these herbicides (Fausey and Renner 1998). Greater soybean tolerance to fluthiacet or flumiclorac at 1400 h or 2200 h applications compared with 0600 h applications could be due to more rapid 42 herbicide drying, less herbicide uptake, or an increase in the detoxifying capabilities of soybean. Beyers and Smeda (1997) reported reduced weed control with a late evening glufosinate (2-amino-4-(hydroxymethylphosphinyl)butanoic acid) application. The presence of dew, lower air temperature, or a lack of light may explain ineffective weed control with an evening glufosinate application. A further understanding of the direct and indirect effect environmental conditions at and following herbicide application is needed to identify the ideal application time of day for photodynamic herbicides. ACKNOWLEDGMENTS The authors thank Gary Powell and Dr. Randy Beaudry for their assistance in this research. Appreciation is extended to Valent U.S.A. Corporation and Novartis Crop Protection, Inc. for their financial support. 43 10. 11. 12. LITERATURE CITED Akey, W. C., T. W. Jurik, and J. Dekker. 1990. Competition for light between velvetleaf (Abutilon theophrasti) and soybean (Glycine max). Weed Res. 30:403- 41 1. Anderson, R. N. and W. L. Koukkari. 1978. Response of velvetleaf (Abutilon theophrasti) to bentazon as affected by leaf orientation. Weed Sci. 26:393-395. Anderson, R. N. and W. L. Koukkari. 1979. Rhythmic movements of some common weeds. Weed Sci. 27:401-415. Beyers, J. T. and R. J. Smeda. 1997. Influence of time of day on glufosinate activity. Proc. N. Cent. Weed Sci. Soc. 52:123. Black, F. S. and H. P. Wilson. 1969. Performance of herbicide adjuvant-sprays as effected by the time of day, by the ratio of herbicide adjuvant, and by the chemical type of the adjuvant. Abstr. Weed Sci. Soc. Am. p. l. Caseley, J. C. 1989. Variations in foliar pesticide performance attributable to humidity, dew, and rain effects. Aspects of App. Biol. 215-225. Coupland, D. 1983. Influence of light, temperature and humidity on the translocation and activity of glyphosate in Elymus repens (=Agropyr0n repens). Weed Res. 23:347-355. Doran, D. L. and R. N. Andersen. 1976. Effectiveness of bentazon applied at various times of day. Weed Sci. 24:567-570. Duke, S. O., J. Lydon, J. M. Becerril, T. D. Sherman, L. P. Lehnen, Jr., and H. Matsumoto. 1991. Protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 39:465-473. Eckl, K. and H. Gruler. 1980. Phase transitions in plant cuticle. Planta 150:102-113. Fausey, J. C. and K. A. Renner. 1998. Broadleaf weed control in soybean with flumiclorac and CGA-248757 alone and in tank mixtures. Abstr. Weed Sci. Soc. Am. 38:9. Flore, J. A. and M. J. Bukovac. 1978. Pesticide effects on the plant cuticle: HI. EPTC effects on the qualitative composition of Brassica oleracea L. leaf cuticles. J. Amer. Soc. Hort. Sci. 103:297-301. 44 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. Gossett, B. J. and C. E. Rieck. 1970. Performance of chloroxuron as influenced by spray additives, spray volumes, and early morning versus late afternoon applications. Proc. South. Weed Sci. Soc. 23:163. Harr J ., R. Guggenheim, G. Schulke, and R. H. Falk. 1991. The leaf surface of major weeds. Basel: Sandoz Agro Ltd. Holen, C. D. and A. G. Dexter. 1993. Effect of increased temperature before and after desmedipham application. Proc. N. Cent. Weed Sci. Soc. 48:86-87. Koukkari, W. L. and M. A. Johnson. 1979. Oscillations of leaves of Abutilon theophrasti (velvetleaf) and their sensitivity to bentazon in relation to low and high humidity. Physiol. Plant. 47:158-162. KudSk, P., T. Olsen, and K. E. Thonke. 1990. The influence of temperature, humidity and simulated rain on the performance of thiarneturon-methyl. Weed Res. 30:261 -269. Lee, H. J. and S. 0. Duke. 1994. Protoporphyrinogen IX-oxidizing activities involved in the mode of fluthiacet of peroxidizing herbicides. J. Agric. Food Chem. 42:2610-2618. Lee, S. D. and L. R. Oliver. 1982. Efficacy of acifluorfen on broadleaf weeds. Times and methods for application. Weed Sci. 30:520-526. Putman, A. R. and S. K. Ries. 1968. Factors influencing the phytotoxicity and movement of paraquat in quackgrass. Weed Sci. 16:80-83. Ritter, R. L. and H. D. Coble. 1981. Influence of temperature and relative humidity on the activity of acifluorfen. Weed Sci. 29:480-485. Wanamarta, G. and D. Penner. 1989. Foliar absorption of herbicides. Rev. Weed Sci. 42215-231 . Weaver, M. L. and R. E. Nylund. 1963. Factors influencing the tolerance of peas to MCPA. Weed Sci. 11:142-148 Weaver, M. L. and R. E. Nylund. 1965. The susceptibility of annual weeds and Canada thistle to MCPA applied at different times of day. Weed Sci. 13:110-113. Wichert, R. A., R. Bozsa, R. E. Talbert, and L. R. Oliver. 1992. Temperature and relative humidity effects on diphenylether herbicides. Weed Technol. 6: 19-24. 45 26. Wills, G. D. and C. G. McWhorter. 1981. Effect of environment on the translocation and toxicity of acifluorfen to showy crotalaria (Crotalaria spectabilis). Weed Sci. 29:397-401. 27. Zhou, P. and W. H. Ahrens. 1995. The effect of time of day of application on herbicide efficacy. Proc. N. Cent. Weed Sci. Soc. 50:90-91. 46 Table 1. Effect of temperature on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment. Treatmenta Rate Temperature Common lambsquarters Redroot pigweed g ha" C % control Fluthiacet 4 10 6 20 4 20 14 36 4 30 24 53 4 40 28 63 F lumiclorac 30 1 0 4 23 30 20 16 32 30 3O 29 41 30 40 31 58 LSD (0.05) 7 10 ‘All treatments were applied with 0.25% nonionic surfactant (NIS). 47 Table 2. Effect of light intensity on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment. Treatment"I Rate Light intensity Common lambsquarters Redroot pigweed g ha" amol m'2 S" % control Fluthiacet 4 0 3 4 4 4 9 8 4 40 23 43 4 1000 38 56 Flumiclorac 30 0 4 1 30 4 5 5 30 40 20 49 30 1000 46 75 LSD (0.05) 5 4 aAll treatments were applied with 0.25% nonionic surfactant (NIS). 48 Table 3. Effect of time to initial light exposure on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment. Time to initial Treatment“ Rate light exposure Common lambsquarters Redroot pi gweed g ha" h % control Fluthiacet 4 0 21 33 4 2 21 33 4 4 21 33 4 6 19 32 4 8 19 31 4 12 19 32 Flumiclorac 30 0 24 42 30 2 23 41 30 4 24 43 30 6 24 43 30 8 23 41 30 12 23 42 LSD (0.05) 3 4 2'All treatments were applied with 0.25% nonionic surfactant (NIS). 49 Table 4. Effect of relative humidity on common lambsquarters and redroot pigweed control with fluthiacet and flumiclorac 72 h after treatment. Treatmenta Rate Relative humidity Commonlambsquarters Redroot pigweed g ha" % % control Fluthiacet 4 10 38 45 4 50 36 44 4 90 38 45 Flumiclorac 30 10 40 48 30 50 39 48 30 90 36 50 LSD (0.05) 7 6 2‘All treatments were applied with 0.25% nonionic surfactant (NIS). 50 Table 5. Effect of dew on common lambsquarters and redroot pi gweed control with fluthiacet and flumiclorac 14 d after treatment. Treatment“ Rate Leaf surface Commonlambsquarters Redroot pigweed g ha" % control F luthiacet 4 dew 92 69 4 no dew 97 87 Flumiclorac 30 dew 91 76 30 no dew 96 95 LSD (0.05) 3 8 “All treatments were applied with 0.25% nonionic surfactant (NIS). 51 Table 6. Herbicide application conditions in 1996, 1997, and 1998 field experiments. Application Air Relative Leaf surface Date treated time Cloud cover temperature humidity moisture“ h % C % 6/13/96 0600 90 19 95 1 1400 30 29 62 5 2200 100 26 88 4 6/24/97 0600 80 26 65 5 1400 20 33 47 5 2200 90 29 62 5 6/9/98 0600 95 14 70 5 1400 30 21 26 5 2200 100 16 55 5 “Visual l to 5 rating with 1 signifying wet and 5 dry. 52 Table 7. Effect of time of application on tolerance and efficacy of fluthiacet and flumiclorac applied at 0600, 1400, and 2000 h.“ Application Common Redroot Treatmentb Rate time Soybean lambsquarters pigweed Velvetleaf g ha" h % injuryc % controld F luthiacet 4 0600 14 74 51 98 4 1400 11 73 74 99 4 2200 12 61 52 98 Flumiclorac 30 0600 16 71 60 94 30 1400 11 68 77 94 30 2200 12 53 60 90 LSD (0.05) 2 7 7 6 “Data averaged over 1996, 1997, and 1998. bAll treatments included either 0.25% (v/v) nonionic surfactant (N18) plus 1.0% (WV) 28% urea ammonium nitrate (UAN) or 0.5% (v/v) crop oil concentrate (COC). cPercent injury 7 d after treatment (DAT). dPercent control 14 DAT. 53 CHAPTER 3 Adjuvant Effects on Fluthiacet and Flumiclorac Efficacy and Soybean Tolerance ABSTRACT Greenhouse and field studies evaluated adj uvant effects on weed control and soybean tolerance with fluthiacet or flumiclorac applied alone and in combination with imazethapyr and oxasulfuron. Adjuvants enhanced common lambsquarters, redroot pigweed, common ragweed, and velvetleaf control with fluthiacet by 53, 57, 29, and 29% and flumiclorac by 36, 62, 41, and 34%, respectively, in the greenhouse. In field studies, soybean injury and common lambsquarters, redroot pi gweed, and common ragweed control were equivalent when fluthiacet or flumiclorac was applied with a cr0p oil concentratel (0.5 or 1.0% v/v) or a nonionic surfactant2 plus 28% urea ammonium nitrate (UAN) (0.25 + 1.0% v/v). In greenhouse studies, a tank mixture of fluthiacet and imazethapyr with a methylated seed oil3 or an organosilicone4 adjuvant enhanced common lambsquarters and velvetleaf control compared with a nonionic surfactant. Redroot pigweed control with fluthiacet plus imazethapyr; and common lambsquarters and velvetleaf control with flumiclorac plus imazethapyr increased by the addition of an organosilicone adjuvant compared with a nonionic surfactant. Redroot pigweed and 54 common ragweed control with tank mixtures of fluthiacet or flumiclorac plus oxasulfuron were enhanced by adding an organosilicone adj uvant compared with a nonionic surfactant. In field evaluations of fluthiacet or flumiclorac plus imazethapyr, adding a nonionic surfactant or an organosilicone adjuvant resulted in equivalent soybean injury and giant foxtail, common lambsquarters, and redroot pi gweed control. The addition of an organosilicone adjuvant increased redroot pigweed control and soybean yield in tank mixtures of fluthiacet or flumiclorac plus oxasulfuron compared with a nonionic surfactant. Nomenclature: Fluthiacet, [[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H- [1 ,3,4]thiadiazolo[3 ,4-a]pyridazin-1-ylidene)amino]phenyl]thio]acetate; flumiclorac, pentyl[2-chloro-4-fluoro-5-(l ,3 ,4,5,6,7-hexahydro-1 ,3-dioxo-2H-isoindol-2- yl)phenoxy]acetic acid; imazethapyr, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo- 1H—imidazol-Z-yl]-5-ethyl-3-pyridinecarboxylic acid; oxasulfuron, 2-[[[[(4,6-dimethyl-2- pyrimidinyl)-amino]carbonyl]aminojsulfonyl] benzoic acid, 3-oxetanyl ester; velvetleaf, Abutilon theophrasti Medik. #' ABUTH; redroot pigweed, Amaranthus retroflexus L. # AMARE; common ragweed, Ambrosia artemisiifolia L. # AMBEL; common lambsquarters, Chenopodium album L. # CHEAL; giant foxtail, Setariafaberi Henm. # SETFA; soybean, Glycine max (L.) Merr. ‘Conrad’ # GLYMA. Key Words: Herbicide additive, surfactant, ABUTH, AMARE, AMBEL, CHEAL, GLYMA. Abbreviations: COC, crop oil concentrate; DAT, days after treatment; MSO, methylated ‘Letters following this symbol are a WSSA-approved computer code from Composite List of Weeds, Revised 1989. Available from WSSA, 810 East 10th Street, Lawrence, KA 66044-8897. 55 seed oil; NIS, nonionic surfactant; Protox, protoporphyrinogen oxidase; UAN, 28% urea ammonium nitrate; v/v, volume per volume. 56 INTRODUCTION Predicting herbicide efficacy is challenging. Environmental conditions at application (Doran and Anderson 1976), herbicide rate (King and Oliver 1992), weed size (Kells et al. 1984), interactions with other herbicides (Hatzios and Penner 1985), and the addition of an adjuvant (Roggenbuck et al. 1990) influence herbicidal response. Adjuvants optimize herbicide penetration and efficacy under adverse environmental conditions (Sun et al. 1996) and provide more consistent control of marginally controlled species (Wills and McWhorter 1981). Enhanced herbicidal efficacy generally reflects increased herbicide absorption (Harrison and Wax 1986); however, increased herbicide absorption does not always correlate with increased efficacy (Starke et al. 1996). The recently developed cyclic imide herbicides fluthiacet and flumiclorac control broadleaf weeds postemergence in corn (Zea mays L.) and soybean (Porpiglia et al. 1994; Kamoshita et al. 1993). The mode of action of cyclic imide, diphenyl ether, oxadiazole, and triazolinone herbicides is protoporphyrinogen oxidase (Protox) inhibition (Anonymous 1995; Duke et a1. 1991; Mito et al. 1991). Protox inhibition leads to an uncontrolled nonenzymatic oxidation of protoporphyrinogen IX to protoporphyrin IX in sensitive plant species. Herbicidal activity of these herbicide classes is light-dependent and closely associated with the concentration of accumulated protoporphyrin IX (Duke et al. 1990). F luthiacet and flumiclorac provide exceptional postemergence velvetleaf control (Brown et al. 1991; Fausey and Renner 1998; Kapusta et al. 1995). Roeth and Schleufer (1994) reported that velvetleaf control with flumiclorac was not affected when flumiclorac was applied with a crop oil concentrate (COC) or a COC plus 28% urea 57 ammonium nitrate (U AN). However, Dill et al. (1994) reported that a COC or an organosilicone spray additive provided more consistent weed control with fluthiacet than a nonionic spray additive. Weed control programs must provide acceptable season-long weed control for each weed species present. This is commonly achieved by tank mixing herbicides. Understanding the potential interactions between herbicides used in tank mixtures is important when developing weed management systems (Young et al. 1996). Tank mixtures of fluthiacet or flumiclorac with imazethapyr or oxasulfuron provide more consistent broad-spectrum weed control compared with fluthiacet or flumiclorac alone (Dill et al. 1994; James et al. 1994; Krutz and Pawlak 1992). Potentially, tank mixtures of fluthiacet or flumiclorac with imazethapyr or oxasulfuron may enhance velvetleaf control and provide consistent broad-Spectrum broadleaf weed control (Dill et al. 1994; James et al. 1994; Kurtz and Pawlak 1992). However, Nelson and Renner (1998) reported that adding fluthiacet to oxasulfuron reduced common ragweed control compared with oxasulfuron alone. Research investigating adjuvant effects on fluthiacet or flumiclorac efficacy and soybean tolerance is limited. Conceivably, adjuvant selection may enhance or reduce efficacy and affect soybean tolerance in tank mixtures with fluthiacet or flumiclorac. Therefore, the objectives of this research were to determine the influence adjuvant selection has on efficacy and soybean tolerance with fluthiacet or flumiclorac applied alone and in tank mixtures with imazethapyr and oxasulfuron. 58 MATERIALS AND METHODS General Methods for Greenhouse Experiments Velvetleaf and common lambsquarters seed was collected at the Michigan State University Crop and Soil Sciences Research Farm in East Lansing, Michigan. Redroot pigweed and common ragweed seed was obtained from a commercial seed supplierz. Seeds were planted in BACCTO3 potting soil in 946 ml plastic pots. Environmental conditions were maintained within a greenhouse at 27 i: 5 C. Plants were grown under a 16-h photoperiod of natural and supplemental high pressure sodium lighting with a photosynthetic photon flux density of 1000 umol m'2 3". Plants were thinned to 1 plant pot", fertilized with 50 ml of a water-soluble fertilizer solution (400 ppm N, 400 ppm P205, and 400 ppm K20), and watered as needed. Herbicides were applied with a continuous belt-linked sprayer fitted with an 8001B flat-fan nozzle4 traveling at 1.53 km h" and delivering 234 L ha‘l at 193 kPa of pressure. Each experiment was a completely randomized design with four replications. Weed control was visually evaluated in each experiment 3, 7 and 14 d after treatment (DAT). Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 indicating plant death. Evaluations represented visual stunting, chlorosis, and necrosis. Dry weight reduction was determined in each experiment 14 DAT by harvesting the 2Seed, V & J Seed Farms, PO. Box 82, Woodstock, IL 60098. 3BACCTO professional planting mix, Michigan Peat Co., PO. Box 98129, Houston, TX 77098. ”Teejet flat-fan nozzles, Spraying Systems Co., North Avenue and Schmale Road, Wheaton, IL 60532. 59 aboveground plant material. Percent dry weight reduction was calculated as 100[1 - (plant dry weight/untreated plant dry weight)]. Adjuvant Efficacy. Experiments were conducted to evaluate adjuvant effects on fluthiacet and flumiclorac efficacy. Commercial formulations of fluthiacet or flumiclorac were applied at 2 g ha" and 15 g ha", respectively. Herbicides were applied with: no adjuvant; UAN (1.0% v/v); Activator 905 (0.25% v/v), Activator 90 plus UAN (0.25 + 1.0% v/v); Herbimax6 (05,10, and 2.0% v/v); Herbimax plus UAN (0.5 + 1.0% v/v); Dash7 (1.0% v/v); Scoil8 (1.0% v/v); Scoil plus UAN (1.0 + 1.0% v/v); Sylgard 3099 (0.25% v/v); and Sylgard 309 plus UAN (0.25 + 1.0% v/v). Separate experiments were conducted for velvetleaf, common lambsquarters, redroot pigweed, and common ragweed. At application, velvetleaf plants were 10 to 11 cm tall with six leaves; common lambsquarters plants were 6 cm tall with six to eight leaves; redroot pi gweed plants were 6 cm tall with four to six leaves; and common ragweed plants were 6 cm tall with Six leaves. Herbicide injury was visually evaluated, and aboveground biomass was harvested 14 DAT, oven dried, and weighed. Tank Mixtures with Fluthiacet and Flumiclorac. Experiments were conducted to 5Activator-90, nonionic surfactant, a mixture of alkyl poloxyethlene ether and free fatty acids, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 6Herbimax, 83% petroleum oil, 17% surfactant, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 7Dash, 45% petroleum hydrocarbons, 5% naphthalene, 1.5% phosphoric acid, and 48.5% mixture of alkyl esters and anionic surfactant. BASF Corp., RTP, NC 27709. 8Scoil, methylated seed oil, AGSCO. Inc., PO. Box 458 Grand Forks, ND 58206. 9Sylgard 309, organosilicone adjuvant, 2-(3-hydroxy-propyl)-heptamethyl-triSiloxane, ethoxylated acetate, Dow Corning Corp., Midland, MI 48686-0944. 60 evaluate adjuvant effect on weed control with tank mixtures of fluthiacet or flumiclorac with imazethapyr and oxasulfuron (Table 4). Treatments included 18 g ha" imazethapyr or 16 g ha" oxasulfuron applied in combination with 1 g ha" fluthiacet or 8 g ha" flumiclorac. All treatments were applied with Activator 90 plus UAN (0.25 + 0.1% v/v), Scoil plus UAN (1.0 + 1.0% v/v), and Sylgard 309 plus UAN (0.25 + 1.0% v/v). At application, velvetleaf plants were 12 cm tall with four to Six leaves; common lambsquarters plants were 9 cm tall with ten to 12 leaves; redroot pigweed plants were 10 cm tall with eight to ten leaves; and common ragweed plants were 6 cm tall with eight to 10 leaves. Herbicide injury was visually evaluated, and aboveground biomass was harvested 14 DAT, oven dried, and weighed. Field Experiments Species Sensitivity. Experiments were conducted at the Michigan State University Research Farm in East Lansing, MI in 1996 and 1997. The soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aerie Ochraqualfs) with 2.4% organic matter in 1996 and a sandy loam with 2.5% organic matter in 1997. The soil pH was 7.9 and 6.7 in 1996 and 1997, respectively. Sites were fall chisel plowed with secondary tillage consisting of two field cultivations at planting. ‘Conrad’ soybean was planted in 76-cm rows at 395,000 seed ha". Plots were 3 m wide by 12.2 m in length in 1996 and 3 m wide by 9.1 m in length in 1997. The experiment was a randomized complete block with four replications. Treatments included 4 g ha" fluthiacet or 30 g ha" flumiclorac applied with Herbimax (0.5 and 1.0% v/v) or Activator 90 plus UAN (0.25 + 1.0% v/v). 61 Herbicides were applied on June 10, 1996 and June 17, 1997, 24 and 26 d after planting (DAP), with a compressed air tractor-mounted sprayer traveling at 6.3 km h" and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles4 spaced 51 cm apart and 48 cm above the weed canOpy. At application, soybean plants were 8 to 10 cm tall with one fully developed trifoliolate; common lambsquarters plants were 1 to 10 cm tall with two to 24 leaves; redroot pigweed plants were 1 to 8 cm tall and from cotyledon to eight leaves; and common ragweed plants were 1 to 7 cm tall and from cotyledon to eight leaves. Soybean injury and weed control were visually evaluated 7, 14, and 28 DAT. Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 signifying plant death. Soybean injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. Tank Mixtures with Fluthiacet and Flumiclorac. Experiments were conducted at the Michigan State University Research Farm at East Lansing, MI in 1997 and 1998. The soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aerie Ochraqualfs) with 2.8 and 4.2% organic matter in 1997 and 1998, respectively. The soil pH was 6.6 and 6.3 in 1997 and 1998, respectively. Sites were fall chisel plowed with secondary tillage consisting of two field cultivations at planting. Asgrowl0 ‘2701 RR’ soybean was planted in 76-cm rows at 345,000 seed ha". Plots were 3 m wide by 10.6 min length. The experiment was a randomized complete block with four replications. Treatments included 2240 g ha" metolachlor preemergence (PRE) followed by 4 g ha" fluthiacet or 30 g ha" flumiclorac postemergence (POST); and tank mixtures of 4 g ha" fluthiacet or 10Soybean, Asgrow Seed Company, PO. Box 7570, Des Moines, IA 50322. 62 30 g ha" flumiclorac with 70 g ha" imazethapyr or 65 g ha" oxasulfuron plus 60 g ha" quizalofop (POST). All POST herbicide treatments were applied with Activator 90 plus UAN (0.25 + 1.0% v/v) or Sylgard 309 plus UAN (0.25 + 1.0% v/v). PRE herbicide applications were applied on May 13, 1997 and 1998. POST herbicide applications were applied on June 17, 1997, and June 8, 1998, 35 and 26 DAP. All herbicide treatments were applied with a compressed air tractor-mounted sprayer traveling at 6.3 km h" and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles“ spaced 51 cm apart and 48 cm above the weed canopy. At application, soybean plants were 10 to 14 cm tall with two fully developed trifoliolates; giant foxtail plants were 1 to 15 cm tall with one to four leaves; common lambsquarters plants were 1 to 10 cm tall with two to 22 leaves; and redroot pigweed plants were 1 to 8 cm tall and from cotyledon to ten leaves. Soybean injury was visually evaluated 3, 7, and 14 DAT. Weed control was evaluated for each species 7, 14, 21, 35, and 56 DAT. Visual ratings were based on a scale fiom 0 to 100%, with 0 indicating no effect and 100 Signifying plant death. Soybean injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. The two middle rows from each plot were harvested with a Massey 10” small-plot combine. Soybean yield was adjusted to 13% moisture. Statistical Analyses All experiments were repeated overtime, and data were analyzed using analysis of variance (ANOVA). Data for individual experiments were combined as analyses revealed no treatment by time interaction. Means were separated by Fisher’s protected l‘Kincaid Equipment Manufacturing, PO. Box 400, Haven, KS 47543. 63 least Significant difference test (LSD) at the 5% level. RESULTS AND DISCUSSION Adjuvant Efficacy. Selected adjuvants increased velvetleaf, common lambsquarters, redroot pigweed, and common ragweed control by fluthiacet in the greenhouse, however, enhancement varied by species (Table 1). All adjuvants, except UAN alone, increased velvetleaf, common lambsquarters, redroot pigweed, and common ragweed control by fluthiacet compared with fluthiacet applied without an adjuvant. Velvetleaf control with fluthiacet was greatest when applied with Herbimax (0.5, 1.0, 2.0% v/v), Herbimax plus UAN, Dash, Scoil, or Scoil plus UAN. Maximum common lambsquarters control with fluthiacet was obtained with Scoil plus UAN, while common ragweed control with fluthiacet was greatest with Sylgard 309 plus UAN. Redroot pigweed control with fluthiacet was greatest with Dash, Scoil plus UAN, Sylgard 309, or Sylgard 309 plus UAN. Although other adjuvants provided maximum control of a single Species, adding Scoil plus UAN to fluthiacet provided the most effective velvetleaf, common lambsquarters, and redroot pigweed control. Velvetleaf, common lambsquarters, redroot pigweed, and common ragweed control with flumiclorac was enhanced in the greenhouse with all adjuvants but UAN alone (Table 2). Maximum velvetleaf control was obtained with flumiclorac plus Herbimax plus UAN or flumiclorac plus Sylgard 309 plus UAN. Adding Sylgard 309 plus UAN provided the greatest redroot pigweed control with flumiclorac. Maximum common lambsquarters control with flumiclorac was achieved by adding Activator 90 plus UAN, 64 Herbimax (2.0% v/v), Dash, Scoil plus UAN, or Sylgard 309 plus UAN. Herbimax (2.0% v/v), Herbimax plus UAN, Scoil plus UAN, or Sylgard 309 plus UAN provided the greatest common ragweed control with flumiclorac. Adjuvants enhanced flumiclorac activity on a Single Species, however, Sylgard 309 plus UAN provided the most effective velvetleaf, common lambsquarters, redroot pigweed, and common ragweed control with flumiclorac. Adding an adjuvant to fluthiacet or flumiclorac increased soybean injury and common lambsquarters, redroot pigweed, and common ragweed control in the field compared with these herbicides applied without an adjuvant (Table 3). Adding Herbimax (0.5 or 1.0% v/v) or Activator 90 plus UAN to fluthiacet or flumiclorac resulted in equivalent soybean tolerance and weed control in the field. This differed from greenhouse studies where common lambsquarters control with fluthiacet or flumiclorac increased when Activator 90 plus UAN was added compared with 0.5% (v/v) Herbimax. In a second field experiment, weed control with fluthiacet or flumiclorac did not increase by adding Sylgard 309 plus UAN or Activator 90 plus UAN when compared with Activator 90 plus UAN (Table 5). Field results were contrary to the greenhouse results where redroot pigweed control with these herbicides increased when applied with Sylgard 309 plus UAN compared with Activator 90 plus UAN. Differences in the greenhouse and field application rates of fluthiacet or flumiclorac may explain these conflicting results. Fluthiacet and flumiclorac were applied in the greenhouse at one-half the field application rate. Thus, weed control in the field may increase by adding Sylgard 309 plus UAN compared with Activator 90 plus UAN if fluthiacet or flumiclorac are applied at reduced rates. Altematively, a change in cuticle development may explain the differences in 65 efficacy between greenhouse and field grown plants. Regardless, field results indicated adjuvant selection did not affect soybean tolerance or weed control with 4 g ha" fluthiacet or 15 g ha" flumiclorac. Tank Mixtures with Fluthiacet and Flumiclorac. Greenhouse. Velvetleaf and common lambsquarters control with fluthiacet plus imazethapyr increased when Scoil plus UAN or Sylgard 309 plus UAN was added. Sylgard 309 plus UAN provided the greatest velvetleaf and common lambsquarters control with flumiclorac plus imazethapyr (Table 4). Redroot pigweed control with fluthiacet plus imazethapyr was greatest with Sylgard 309 plus UAN. Scoil plus UAN or Sylgard 309 plus UAN increased redroot pigweed control with fluthiacet plus oxasulfuron compared with Activator 90 plus UAN. Adding Sylgard 309 plus UAN to flumiclorac plus oxasulfuron maximized redroot pigweed control while common ragweed control was greatest with Sylgard 309 plus UAN (Table 4). Field. Soybean exhibited leaf necrosis from tank mixtures with fluthiacet or flumiclorac, but this was not apparent 21 DAT (data not presented). Kapusta et al. (1986) and Wichert and Talbert (1993) reported that leaf necrosis from Protox-inhibiting herbicides does not affect soybean yield. In contrast to our greenhouse results, common lambsquarters and redroot pigweed control in the field with tank mixtures of fluthiacet or flumiclorac plus imazethapyr and Activator 90 plus UAN equaled that of Sylgard 309 plus UAN (Table 5). Adjuvant selection did not affect soybean injury, weed control, and soybean yield with tank mixtures of fluthiacet or flumiclorac with imazethapyr in the field. 66 Adding Sylgard 309 plus UAN to fluthiacet plus oxasulfuron plus quizalofop increased common lambsquarters and redroot pi gweed control which was reflected as a 14% increase in soybean yield when compared with adding Activator 90 plus UAN. Similarly, redroot pigweed control and soybean yield with flumiclorac plus oxasulfuron plus quizalofop increased by 12 and 16%, respectively, by adding Sylgard 309 plus UAN compared with Activator 90 plus UAN. Field results suggest adj uvant selection does affect the efficacy of fluthiacet or flumiclorac tank mixtures in the field. Thus, careful consideration must be given when choosing an adjuvant for fluthiacet and flumiclorac tank mixtures. Cantwell et al. (1989) and Wesley and Shaw (1992) reported that tank mixtures with Protox-inhibiting herbicides may increase or decrease weed control. Nelson and Renner (1998) observed decreased common ragweed control with a tank mixture of fluthiacet plus oxasulfuron compared with oxasulfuron alone. An alternate adjuvant choice may eliminate antagonism between fluthiacet and oxasulfuron when applied in a tank mixture. Fluthiacet and flumiclorac activity on velvetleaf, common lambsquarters, redroot pi gweed, and common ragweed was enhanced by selected adjuvants. However, a Single application of fluthiacet or flumiclorac provided insufficient broad-Spectrum broadleaf weed control in the field (Fausey and Renner 1998). James et al. (1994) and Kurtz and Pawlak (1993) reported enhanced broadleaf weed control by adding fluthiacet or flumiclorac to several postemergence broadleaf herbicides. With the appropriate adjuvant, tank mixtures of imazethapyr or oxasulfuron plus quizalofop with fluthiacet or flumiclorac may provide season-long broad-spectrum weed control in the field. 67 ACKNOWLEDGMENTS The authors thank Gary Powell and Jason Simon for their assistance in this research. Appreciation is extended to Valent U.S.A. Corporation and Novartis Crop Protection, Inc. for their financial support. 68 10. 11. 12. LITERATURE CITED Anonymous. 1995. F luthiacet herbicide technical information bulletin. Greensboro, NC: CIBA-GEIGY Corp., Agricultural Division. Brown, W. B., M. S. DeFelice, and C. S. Holman. 1991. Weed control in corn and soybeans with V-23031. Proc. N. Cent. Weed Sci. Soc. 46:40. Cantwell, J. R., R. A. Liebl, and F. W. Slife. 1989. Irnazethapyr for weed control in soybean (Glycine max). Weed Technol. 7:345-351. Doran, D. L. and R. N. Anderson. 1976. Effectiveness of bentazon applied at various times of day. Weed Sci. 24:567-570. Dill, T. R., J. R. James, L. Stahlberg, and E. R. Hill. 1994. Update on the herbicidal activity of CGA-248757 in corn in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:58. Duke, S. O., J. M. Becerril, T. D. Sherman, J. Lydon, and H. Matsumoto. 1990. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci. 30:367-378. Fausey, J. C. and K. A. Renner. 1998. Broadleaf weed control in soybeans with flumiclorac and CGA-248757 alone and in tank mixtures. Abstr. Weed Sci. Soc. Am. 38:9. Hatzios, K. K. and D. Penner. 1985. Interactions of herbicides with other agrochemicals in higher plants. Rev. Weed Sci. 1:1-63. Harrison, S. K. and L. M. Wax. 1986. Adjuvant effects on absorption, translocation, and metabolism of haloxyfop-methyl in corn (Zea mays). Weed Sci. 34: 1 85-195. James, J. R., L. Stahlberg, T. R. Dill, and G. Hill. 1994. Update on the herbicidal activity of CGA-248757 in soybeans in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:129. Kamoshita, K., E. Nagano, S. Hashimoto, R. Sato, R. Yoshida, and H. Oshio. 1993. V-23031-A new herbicide for postemergence weed control in soybeans and field corn. Abstr. Weed Sci. Soc. Am. 53:3. Kapusta, G., S. E. Curvey, and S. T. Autrnan. 1995. Soybean weed control with CGA-248757 and CGA-277476 at three weed growth stages. Research Report N. Cent. Weed Sci. Soc. 52:253-255. 69 l3. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. Kells, J. J ., W. F. Meggitt, and D. Penner. 1984. Absorption, translocation, and activity of fluazifop-butyl as influenced by plant growth stage and environment. Weed Sci. 32: 143-149. King, C. A. and L. R. Oliver. 1992. Application rate and timing of acifluorfen, bentazon, chlorimuron, and imazaquin. Weed Technol. 6:526-534. Kurtz, A. R. and J. A. Pawlak. 1992. Postemergence weed control in field corn with V-23031 herbicide. Proc. N. Cent. Weed Sci. Soc. 47:47. Mito, N., R. Sato, M. Miyakado, H. Oshio, and S. Tanaka. 1991. In vitro mode of fluthiacet of N—Phenylimide photobleaching herbicides. Pestic. Biochem. Physiol. 40:128-135. Nelson, K. A. and K. A. Renner. 1998. Weed control in wide- and narrow-row soybean (Glycine max) with imazamox, imazethapyr, and CGA-277476 plus quizalofop. Weed Technol. 12:137-144. Porpiglia, P. J ., E. R. Hill, and A. Tally. 1994. CGA-248757 for postemergence broadleaf weed control in corn (Zea mays L.) and soybeans (Glycine max (L.) Merr.). Abstr. Weed Sci. Soc. Am. 34:2. Roggenbuck, F. C., L. Rowe, D. Penner, L. Petroff, and R. Burrow. 1990. Increasing postemergence herbicide efficacy and rainfastness with silicone adjuvants. Weed Technol. 4:576-580. Roeth, F. W. and I. Schleufer. 1994. Postemergence velvetleaf control in soybeans. Proc. N. Cent. Weed Sci. Soc. 49:36-41. Sander, K. W. and P. J. Porpiglia. 1996. CGA-248757 combinations for broadleaf weed control in soybeans. Proc. N. Cent. Weed Sci. Soc. 51:132. Starke, R. J ., K. A. Renner, D. Penner, and F. C. Roggenbuck. 1996. Influence of adjuvants and desmedipham plus phenmedipham on velvetleaf (Abutilon theophrasti) and sugarbeet response to triflusulfuron. Wed Sci. 442489-495. Sun J ., C. L. Foy, and H. L. Witt. 1996. Effect of organosilicone surfactants on the rainfastness of primisulfuron in velvetleaf (Abutilon theophrasti). Weed Technol. 10:263-267. Wesley, T. M. and D. R. Shaw. 1992. Interactions of diphenylether herbicides with chlorimuron and imazaquin. Weed Technol. 62345-351. Wills, G. D. and C. G. McWhorter. 1981. Effect of environment on the translocation and toxicity of acifluorfen to showy crotalaria (Crotalaria 70 26. spectabilis). Weed Sci. 29:397-401. Young, B. G., S. E. Hart, and L. M. Wax. 1996. Interactions of sethoxydim and corn (Zea mays) postemergence broadleaf herbicides on three annual grasses. Weed Technol. 10:914-922. 71 Table I. Adjuvant effect on fluthiacet efficacy in the greenhouse 14 d after treatment.“ Adjuvant Rate ABUTH CHEAL AMARE AMBEL % v/v % control No adjuvant — 69 18 16 12 UANb 1.0 93 14 48 19 Activator 90 0.25 52 34 37 19 Activator 90 + UAN 0.25 + 1.0 83 41 48 20 Herbimax 0.5 91 28 46 19 Herbimax 1 .0 95 36 46 24 Herbimax 2.0 97 44 57 24 Herbimax + UAN 0.5 + 1.0 97 25 45 24 Dash 1.0 96 56 64 29 Scoil 1.0 96 53 45 24 Scoil + UAN 1.0 + 1.0 98 71 63 30 Sylgard 309 0.25 76 35 68 19 Sylgard 309 + UAN 0.25 + 1.0 90 45 73 41 Untreated control — 0 0 0 LSD (0.05) 7 5 ll 4 “All treatments received 2 g ha" fluthiacet. bUAN, 28% urea ammonium nitrate. 72 Table 2. Adjuvant effect on flumiclorac efficacy in the greenhouse 14 d after treatment.“ Adjuvant Rate ABUTH CHEAL AMARE AMBEL % v/v % control No adjuvant — 51 20 28 25 UAN“ 1.0 54 21 37 28 Activator 90 0.25 66 48 49 36 Activator 90 + UAN 0.25 + 1.0 73 54 57 52 Herbimax 0.5 66 30 63 44 Herbimax 1.0 66 48 74 53 Herbimax 2.0 62 54 61 61 Herbimax + UAN 0.5 + 1.0 85 43 66 63 Dash 1 .0 71 51 73 58 Scoil 1.0 68 48 54 46 Scoil + UAN 1.0 + 1.0 63 54 71 64 Sylgard 309 0.25 59 49 71 51 Sylgard 309 + UAN 0.25 + 1.0 78 56 90 66 Untreated control — 0 0 0 0 LSD (0.05) 7 5 14 7 “All treatments received 15 g ha" flumiclorac. bUAN, 28% urea ammonium nitrate. 73 Table 3. Adjuvant effect on fluthiacet or flumiclorac soybean tolerance and efficacy in the field.“ Herbicide“ Adjuvantc Rate GLYMA CHEAL AMARE AMBEL % v/v % injury % control F luthiacet no adjuvant — 5 24 57 65 Herbimax 0.5 14 98 76 97 Herbimax 1.0 1 5 91 77 92 Activator 90 + UAN 0.25 + 1.0 16 95 80 92 Flumiclorac no adjuvant —— 7 52 74 78 Herbimax 0.5 13 90 97 98 Herbimax l .0 1 5 99 99 99 Activator 90 + UAN 0.25 + 1.0 15 89 99 98 LSD (0.05) 2 19 17 12 “ Soybean injury 7 d after treatment (DAT) and weed control 14 DAT. l’I‘reatrnents applied with either 4 g ha" fluthiacet or 30 g ha" flumiclorac. cUAN, 28% urea ammonium nitrate. 74 Table 4. Broadleaf weed control in the greenhouse with fluthiacet and flumiclorac tank mixtures 14 d after treatment. Treatment Rate Adjuvant“ ABUTH CHEAL AMARE AMBEL g ha" % control Imazethapyr + fluthiacet 18 + 1 Activator 90 87 25 81 56 Imazethapyr + fluthiacet 18 + 1 Scoil 97 43 77 63 Imazethapyr + fluthiacet 18 + 1 Sylgard 309 96 48 92 54 Imazethapyr + flumiclorac 18 + 8 Activator 90 68 44 85 66 Imazethapyr + flumiclorac 18 + 8 Scoil 69 33 87 57 Imazethapyr + flumiclorac 18 + 8 Sylgard 309 91 53 92 58 Oxasulfiiron + fluthiacet 16 + l Activator 90 91 48 67 57 Oxasulfuron + fluthiacet 16 + l Scoil 98 56 80 54 Oxasulfuron + fluthiacet 16 + 1 Sylgard 309 96 55 88 68 Oxasulfuron + flumiclorac 16 + 8 Activator 90 83 53 68 46 Oxasulfuron + flumiclorac 16 + 8 Scoil 83 54 71 57 Oxasulfuron + flumiclorac 16 + 8 Sylgard 309 90 60 93 59 LSD (0.05) 8 9 10 10 “Activator 90 and Sylgard 309 treatments were applied at 0.25% v/v. Scoil treatments were applied at 1.0% v/v. 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Row 05 E 22% 83528 98 35:8 833 .m. 8385 76 CHAPTER 4 Broadleaf Weed Control in Corn (Zea mays) and Soybean (Glycine max) with Fluthiacet and Flumiclorac Alone and in Tank Mixtures ABSTRACT Greenhouse and field studies evaluated broadleaf weed control with fluthiacet and flumiclorac applied alone and in tank mixtures. Velvetleaf, common lambsquarters, redroot pi gweed, common ragweed, common cocklebur, eastern black nightshade, and wild mustard growth in the greenhouse were reduced by 50% from 0.1, 2.9, 0.9, 1.1, 0.8, 0.4, and 1.2 g ha" of fluthiacet and 0.7, 3.0, 2.4, 3.3, 3.0, 3.4, and 74.1 g ha“ of flumiclorac, respectively. Fluthiacet or flumiclorac tank mixtures with atrazine, bentazon, bromoxynil, dicamba, halosulfuron, imazethapyr, lactofen, primisulfuron plus prosulfuron, or 2,4-D increased velvetleaf, common lambsquarters, redroot pigweed, or common ragweed control in the greenhouse 14 d after treatment (DAT) when compared with the control provided by the tank mix partner alone. Redroot pigweed control increased when flumiclorac was tank mixed with oxasulfuron compared with oxasulfuron alone. However, adding fluthiacet to oxasulfuron did not increase velvetleaf, common lambsquarters, redroot pigweed, or common ragweed control in the greenhouse. In field studies, tank mixtures of fluthiacet or flumiclorac plus atrazine, dicamba, and 2,4-D 77 increased velvetleaf control compared with control by atrazine, dicamba, and 2,4-D alone. Fluthiacet or flumiclorac tank mixtures with primisulfuron plus prosulfuron increased common lambsquarters control compared with primisulfuron plus prosulfinon alone. Fluthiacet or flumiclorac tank mixtures with bentazon, lactofen, or oxasulfuron increased weed control in the field 14 DAT; however, season-long control of redroot pigweed, common ragweed, and eastern black nightshade with bentazon tank mixtures; common ragweed and eastern black nightshade with oxasulfuron tank mixtures; and common lambsquarters with lactofen tank mixtures was less than 80%. Tank mixing flumiclorac with imazethapyr provided season-long common lambsquarters, redroot pigweed, common ragweed, and eastern black nightshade control. Nomenclature: Atrazine, 6-chloro-N-ethyl-N’ -( 1-methylethyl)—1,3 ,5-triazine-2,4— diamine; bentazon, 3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin—4(3H)-one 2,2-dioxide; bromoxynil, 3,5-dibromo-4-hydroxybenzonitrile; 2,4-D, (2,4-dichlorophenoxy)acetic acid; dicamba, 3,6-dichloro-2-methoxybenzoic acid; fluthiacet, methy1[[2-chloro-4- fluoro-S-[(tetrahydro-3-oxo-1H, 3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1- ylidene)amino]phenyl]thio]acetate; flumiclorac, pentyl[2-chloro-4-fluoro-5-(1,3,4,5,6,7- hexahydro-l,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid; halosulfuron, methyl 5- [[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonylaminosulfonyl]-3-chloro-1-methyl- 1 -H— pyrazole-4-carboxylate; imazethapyr, 2-[4,5-dihydro-4-methyl—4-(1-methylethyl)-5-oxo- 1H—imidazol-Z-yl]-5-ethyl-3-pyridinecarboxylic acid; lactofen, (fi-Z-ethoxy-l-methyl-Z- oxoethyl 5-[2-chloro—4-(trifluoromethyl)phenoxy]-2-nitrobenzoate; oxasulfiiron, 2- [[[[(4,6-dimethyl-2-pyrimidinyl)-amino]carbonyl]amino]sulfonyl] benzoic acid, 3- oxetanyl ester; primisulfuron, 2-[[[[[4,6-bis(difluoromethoxy)—2- 78 pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid; prosulfuron, 1-(4-methoxy-6- methyl-triazin-Z-yl)-3-[2-(3,3,3-trifluoropropyl)-phenylsulfonyl]-urea; common cocklebur, Xanthium strumarium L. # XANST; common lambsquarters, Chenopodium album L. # CHEAL; common ragweed, Ambrosia artemisiifolia L. # AMBEL; eastern black nightshade, Solanum ptycanthum Dun. # SOLPT; Pennsylvania smartweed, Polygonum pensylvanicum L. # POLPY; redroot pigweed, Amaranthus retroflexus L. # AMARE; velvetleaf, Abutilon theophrasti Medik. #1 ABUTH; wild mustard, Brassica kaber (D.C.) L.C. Wheeler # SINAR; corn, Zea mays L. ‘Pioneer 3751’, ‘Dekalb 404SR’, and ‘Dekalb 493 SR’ # ZEAMA; soybean, Glycine max (L.) Merr. ‘Conrad’ # GLYMA. Key Words: Antagonism, herbicide interaction, Protox, ABUTH, AMARE, AMBEL, CHEAL, POLPY, SINAR, SOLPT, XAN ST, GLYMA, ZEAMA. Abbreviations: COC, crop oil concentrate; DAP, days after planting; DAT, days after treatment; NIS, nonionic surfactant; Protox, protoporphyrinogen oxidase; UAN, 28% urea ammonium nitrate; v/v, volume per volume. ‘Letters following this symbol are a WSSA-approved computer code from Composite List of Weeds, Revised 1989. Available from WSSA, 810 East 10th Street, Lawrence, KA 66044-8897. 79 INTRODUCTION Several commercial and experimental herbicides including cyclic imides, diphenyl ethers, oxadiazoles, and triazolinones inhibit protoporphyrinogen oxidase (Protox), the enzyme that converts protoporphyrinogen IX to protoporphyrin IX (Anonymous 1995; Duke et a1. 1991; Mito et al. 1991). Protox inhibition, although detectable in sensitive plant species 30 minutes after herbicide exposure, requires light to initiate herbicidal activity (Duke et al. 1990; Lehnen et al. 1990). Fluthiacet and flumiclorac are cyclic imide herbicides used in corn and soybean to control broadleaf weeds postemergence (Porpiglia et al. 1994; Kamoshita et al. 1993). F luthiacet and flumiclorac provided greater than 96% season-long velvetleaf control (Brown et al. 1991; F ausey and Renner 1998; Kapusta et al. 1995). However, season- long common cocklebur control with fluthiacet was 83% (Kapusta et al. 1995), and Pennsylvania smartweed control with flumiclorac was 60% (Brown et al. 1991). Tank mixtures with fluthiacet or flumiclorac provided more consistent broad-spectrum weed control when compared with fluthiacet or flumiclorac alone (Dill et a1. 1994; James et al. 1994; Kurtz and Pawlak 1992). Fluthiacet or flumiclorac tank mixtures with acifluorfen (5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid), atrazine, bentazon, chlorimuron (2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl] benzoic acid), dicamba, imazethapyr, nicosulfuron (2-[[[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N,N—dimethyl-3-pyridinecarboxamide), primisulfuron, prosulfuron, or 2,4-D may enhance velvetleaf control and provide more consistent broadleaf weed control compared with these herbicides applied alone (Dill et al. 1994; James et al. 1994; Kurtz and Pawlak 1992). 80 Understanding interactions between herbicides used in tank mixtures is important for the development of effective weed control programs. Giant foxtail (Setariafaberi Herrm.) control with sethoxydim (2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3- hydroxy-Z-cyclohexen-l-one) was not affected by adding fluthiacet or flumiclorac (James et al. 1994; Young et al. 1996); yet, shattercane (Sorghum bicolor (L.) Moench) control was reduced (Young et al. 1996). Large crabgrass (Digitaria sanguinalis (L.) Scop.) control with sethoxydim was not affected by the addition of fluthiacet, however, control was reduced when flumiclorac was added. Fluthiacet or flumiclorac tank mixtures with glyphosate (N-(phosphonomethy1)glycine) increased velvetleaf and common ragweed control compared with glyphosate alone (Lich et a1. 1997). In contrast, tank mixing fluthiacet with oxasulfuron decreased common ragweed control compared with oxasulfuron alone (Nelson and Renner 1998). Potential benefits of fluthiacet and flumiclorac include low use rates, short-half lives, resistance management, and the ability to broaden the spectrum of other herbicides (Anonymous 1995). Research investigating corn and soybean tolerance and weed control with fluthiacet or flumiclorac is limited. Tank mixtures including fluthiacet or flumiclorac may increase broadleaf weed control, however, affects on crop tolerance have not been reported. Therefore, the objective of this research was to evaluate corn and soybean tolerance and broadleaf weed control with fluthiacet and flumiclorac applied alone and in tank mixtures. 81 MATERIALS AND METHODS General Methods for Greenhouse Experiments Velvetleaf, common lambsquarters, common cocklebur, and eastern black nightshade seed were collected at the Michigan State University Research Farm in East Lansing. Redroot pigweed and common ragweed seed was obtained from a commercial seed supplier’. The corn variety ‘Pioneer 3751’3 and soybean variety ‘Conrad’ were evaluated. Seeds were planted in BACCTO‘1 potting soil in 946 ml plastic pots. Environmental conditions were maintained within a greenhouse at 27 i 5 C. Plants were grown under a 16-h photoperiod of natural and supplemental high pressure sodium lighting with a photosynthetic photon flux density of 1000 amol m2 5". Plants were thinned to 1 plant pot", fertilized with 50 ml of a water-soluble fertilizer solution (400 ppm N, 400 ppm P205, and 400 ppm K20), and watered as needed. Herbicides were applied with a continuous belt-linked sprayer fitted with an 8001B flat-fan nozzles traveling at 1.53 km h" and delivering 234 L ha‘l at 193 kPa of pressure. Each experiment was a completely randomized design with four replications. Crop tolerance and weed control were visually evaluated in each experiment 3, 7 and 14 d after treatment (DAT). Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 indicating plant death. Evaluations represented visual stunting, 2Seed, V & J Seed Farms, PO. Box 82, Woodstock, IL 60098. 3Corn, Pioneer Hi-Bred International, Inc., Des Moines, IA 50301. ‘BACCTO professional planting mix, Michigan Peat Co., PO. Box 98129, Houston, TX 77098. 5Teej et flat-fan nozzles, Spraying Systems Co., North Avenue and Schmale Road, Wheaton, IL 60532. 82 chlorosis, and necrosis. Dry weight reduction was determined in each experiment 14 DAT by harvesting the aboveground plant material. Percent dry weight reduction was calculated as 100[1 - (plant dry weight/untreated plant dry weight)]. Species Sensitivity. Experiments compared weed sensitivity to fluthiacet and flumiclorac. Commercial formulations of each herbicide were applied at various rates. Herbicides were applied with 0.25% (v/v) nonionic surfactant6 (NIS) and 1.0% (v/v) 28% urea ammonium nitrate (U AN). At application, velvetleaf plants were 5 cm tall with two leaves, 7.5 cm tall with four leaves, and 11 cm tall with six to seven leaves; common lambsquarters plants were 6 cm tall with six to eight leaves; redroot pi gweed plants were 6 cm tall with four to six leaves; common ragweed plants were 6 cm tall with six to eight leaves; common cocklebur plants were 9 cm tall with four to five leaves; eastern black nightshade plants were 5 cm tall with five to seven leaves; and wild mustard plants were 6 cm tall with five to six leaves. Herbicide injury was visually evaluated, and aboveground biomass was harvested 14 DAT, oven dried, and weighed. Separate experiments were conducted for each weed species. Data were fit to the log logistic model as described by Seefeldt et al. (1995). Nonlinear regression was conducted with SAS7, and GR50 values were calculated for both plant dry weight reduction and the percent of the field use rate required to reduce plant growth by 50% (Table 1). Dry weight reduction represents the g ha‘l required to reduce plant grth by 50%, whereas percent of the field use rate represents the percent of either 4 g ha'l fluthiacet or 30 g ha" 6Activator-9O, nonionic surfactant, a mixture of alkyl polyoxyethylene ether and fatty acids, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 7SAS Institute Inc., SAS Circle, Box 8000, Cary, NC 27512-8000. 83 flumiclorac required to reduce plant growth by 50%. Tank Mixtures with Fluthiacet and Flumiclorac. Experiments evaluated corn tolerance and weed control with tank mixtures including fluthiacet or flumiclorac. Treatments included an untreated control, 210 g ha'l atrazine, 70 g ha" bromoxynil, 70 g ha" dicamba, 9 g ha‘l halosulfuron, 10 g ha" primisulfuron plus prosulfirron (6:4), and 140 g ha" 2,4-D amine applied alone and in a tank mixture with 1 g ha'l fluthiacet or 8 g ha" flumiclorac. All atrazine treatments were applied with 1.0% (v/v) crop oil concentrate8 (COC); and bromoxynil, dicamba, halosulfuron, primisulfuron plus prosulfuron, and 2,4- D treatments included 0.25% (v/v) NIS“. Corn plants were 16 cm tall with four leaves; velvetleaf plants were 11 cm tall with four to five leaves; common lambsquarters plants were 9 cm tall with 10 to 12 leaves; redroot pigweed plants were 10 cm tall with eight to ten leaves; and common ragweed plants were 10 cm tall with eight to 12 leaves. Herbicide injury was visually evaluated, and aboveground biomass was harvested 14 DAT, oven dried, and weighed. Experiments evaluated soybean tolerance and weed control in the greenhouse with fluthiacet or flumiclorac tank mixtures. Treatments included an untreated control, 210 g ha’l bentazon, 18 g ha‘l imazethapyr, 26 g ha" lactofen, and 16 g ha" oxasulfuron applied alone and in a tank mixture with 1 g ha" fluthiacet or 8 g ha'1 flumiclorac. All bentazon treatments were applied with 1.0% (v/v) COC“; imazethapyr and oxasulfuron treatments included 0.25% (v/v) NIS" plus 1.0% (v/v) UAN; and lactofen treatments included 0.5% COCB. At application, soybean plants were 10 cm tall with two trifoliolates, and weed 8Herbimax, 83% petroleum oil, 17% surfactant, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 84 sizes were as previously described. Herbicide injury was visually evaluated, and aboveground biomass was harvested 14 DAT, oven dried, and weighed. Field Experiments Corn. Experiments were conducted at the Michigan State University Research Farm in East Lansing, MI in 1996 and 1997. The soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aeric Ochraqualfs) with 3.1 and 3.2% organic matter in 1996 and 1997, respectively. The soil pH was 6.5 and 7.2 in 1996 and 1997, respectively. Sites were fall moldboard plowed with secondary tillage consisting of two field cultivations at planting. ‘DK 404 SR’9 corn was planted in 76-cm rows at 62,000 seed ha‘1 in 1996, and ‘DK 493 SR’9 corn was planted in 76-cm rows at 56,000 seed ha" in 1997. Plots were 3 m wide by 9.1 m in length. The experiment was a randomized complete block with three replications. Treatments included 840 g ha‘l atrazine, 280 g ha" bromoxynil, 208 g ha'l dicamba, 35 g ha" halosulfuron, 40 g ha‘l primisulfuron plus prosulfiiron (6:4), and 560 g ha'l 2,4-D amine applied alone and in a tank mixture with 4 g ha‘1 fluthiacet or 30 g ha'l flumiclorac. A weed-free control and an untreated control were included. All atrazine treatments included 1.0% (v/v) COCS; and bromoxynil, dicamba, halosulfuron, primisulfuron plus prosulfuron, and 2,4—D treatments included 0.25% (v/v) NIS". Sethoxydim was applied broadcast for annual grass control June 3, 1996 and June 9, 1997. Herbicides were applied on June 14, 1996 and June 13, 1997, 28 and 30 d after planting (DAP), with a compressed air tractor-mounted sprayer traveling at 5.7 km h" and 9Corn, DEKALB Genetics Corporation, 3100 Sycamore Road Dekalb, IL 60115. 85 delivering 187 L ha“l at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At application, corn plants were 13 to 20 cm tall with five to six leaves; Pennsylvania smartweed plants were 1 to 3 cm tall and from cotyledon to three leaves; velvetleaf plants were 1 to 10 cm tall and from cotyledon to five leaves; common lambsquarters plants were 1 to 7 cm tall with two to ten leaves; and redroot pigweed plants were 1 to 8 cm tall and from cotyledon to eight leaves. Corn injury was visually evaluated 3, 7, and 14 DAT. Weed control was evaluated for each species 7, 14, 21, 3S, and 56 DAT. Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 signifying plant death. Corn injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. The two middle rows from each plot were harvested with a Massey 10IO small-plot combine. Corn yield was adjusted to 15.5% moisture. Soybean. Experiments were conducted at the Michigan State University Research Farm in East Lansing, MI in 1996 and 1997. The soil was a Capac sandy clay loam (fine- loamy, mixed mesic Aeric Ochraqualfs) with 2.4% organic matter in 1996 and a sandy loam with 2.5% organic matter in 1997. The soil pH was 7.9 and 6.7 in 1996 and 1997, respectively. The 1996 and 1997 sites were fall chisel plowed with secondary tillage consisting of two field cultivations at planting. ‘Conrad’ soybean was planted in 76-cm rows at 395,000 seed ha". Plots were 3 m wide by 12.2 m in length in 1996, and 3 m wide by 9.1 m in length in 1997. The experiment was a randomized complete block with four replications. Treatments loKincaid Equipment Manufacturing, PO. Box 400, Haven, KS 47543. 86 included 840 g ha" bentazon, 105 g ha‘l lactofen, 70 g ha'l imazethapyr, 65 g ha" oxasulfuron applied alone and in a tank mixture with 4 g ha‘l fluthiacet or 30 g ha‘l flumiclorac, a weed-free control, and an untreated control. All bentazon treatments were applied in combination with 1.0% (v/v) COCs; imazethapyr and oxasulfuron treatments included 0.25% (v/v) NIS" plus 1.0% (v/v) UAN; and lactofen treatments included 0.5% (v/v) COC”. Herbicides were applied on June 10, 1996 and June 17, 1997, 24 and 26 DAP, with a compressed air tractor-mounted sprayer traveling at 6.3 km h'1 and delivering 178 L ha'l at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At application, soybean plants were 8 to 10 cm tall with one fiilly developed trifoliolate; eastern black nightshade plants were 1 to 4 cm tall and from cotyledon to five leaves; common lambsquarters plants were 1 to 10 cm tall with two to 24 leaves; redroot pi gweed plants were 1 to 8 cm tall and fi'om cotyledon to eight leaves; and common ragweed plants were l to 7 cm tall and from cotyledon to eight leaves. Soybean injury was visually evaluated 3, 7, and 14 DAT. Weed control was evaluated for each species 7, 14, 21, 35, and 56 DAT. Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 signifying plant death. Soybean injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. The two middle rows from each plot were harvested with a Massey 10lo small-plot combine. Soybean yield was adjusted to 13% moisture. Statistical Analyses All experiments were repeated over time, and data were analyzed using analysis of 87 variance (AN OVA). Data for individual experiments were combined as analyses revealed no treatment by time interaction. Means were separated by Fisher’s protected least significant difference test (LSD) at the 5% level. RESULTS AND DISCUSSION Greenhouse Experiments Species Sensitivity. Species sensitivities to fluthiacet or flumiclorac were calculated as GR50 values based on a percent dry weight reduction and converted to the percent of the field use rate (Table 1). The field use rate for fluthiacet is 4 to 5 g ha" (Anonymous 1995), whereas flumiclorac is used at rates of 30 to 60 g ha" (Kurtz and Pawlak 1993). Calculated values for the percent of the field use rate of fluthiacet or flumiclorac required to reduce plant growth by 50% are based on application rates used in our field research; 4 and 30 g ha", respectively. Velvetleaf was sensitive to both herbicides. GR50 values were below 10% of the field use rate for either herbicide (Table 1). Two, four, and six to seven-leaf velvetleaf were more sensitive to fluthiacet when compared with flumiclorac. GR50 values calculated on the percent of the field use rate required to reduce the growth of four and six to seven leaf velvetleaf by 50% revealed greater sensitivity to fluthiacet compared with flumiclorac. However, GR50 values calculated on the percent of the field use rate revealed two leaf velvetleaf were more sensitive to flumiclorac than fluthiacet. The quantity of active ingredient required to reduce common lambsquarters dry weight by 50% did not differ between fluthiacet and flumiclorac (Table 1). However, based on 88 the percent of the field rate required for a 50% reduction in growth, common lambsquarters had greater tolerance to fluthiacet compared with flumiclorac. GRso values calculated on redroot pi gweed, common ragweed, and common cocklebur dry weight reduction indicated these species were more sensitive to fluthiacet than flumiclorac. When the GR50 values were converted to a percent of the field use rate, values revealed redroot pigweed, common ragweed, and cormnon cocklebur were more sensitive to flumiclorac than fluthiacet. These data support Kapusta et al. (1995) and Brown et al. (1991) that common ragweed is more sensitive to flumiclorac when compared with fluthiacet. Eastern black nightshade and wild mustard required less active ingredient and a lower percent of the field use rate of fluthiacet to reduce growth by 50% when compared with flumiclorac. GR50 values for eastern black nightshade were below 12% of the field use rate for either herbicide, while GR,0 values for wild mustard were 30% of the field use rate for fluthiacet and 245% for flumiclorac. Thus, our results suggest broadleaf weed sensitivity to fluthiacet and flumiclorac varies by species. Tank Mixtures with Fluthiacet and Flumiclorac. Adding fluthiacet or flumiclorac to atrazine, dicamba, 2,4-D, bromoxynil, halosulfuron, or primisulfuron plus prosulfuron increased corn injury 3 DAT compared with these herbicides applied alone (Table 2). Tank mixtures with flumiclorac resulted in greater corn injury compared with fluthiacet tank mixtures. Cantwell et al. (1989) and Wesley and Shaw (1992) reported that tank mixtures with Protox-inhibiting herbicides may increase or decrease weed control. Fluthiacet or flumiclorac tank mixtures with atrazine or dicamba increased velvetleaf and common 89 lambsquarters control 14 DAT compared with atrazine or dicamba alone (Table 2). Redroot pigweed and common ragweed control increased when flumiclorac, but not when fluthiacet was tank mixed with atrazine or dicamba. Fluthiacet or flumiclorac tank mixtures with 2,4-D increased velvetleaf, redroot pi gweed, and cormnon ragweed control compared with 2,4-D alone. Velvetleaf, common lambsquarters, and redroot pigweed control with bromoxynil increased by adding fluthiacet or flumiclorac. Common lambsquarters control increased, but common ragweed control decreased with fluthiacet or flumiclorac plus halosulfuron compared with halosulfuron alone. Redroot pigweed control with primisulfuron plus prosulfuron increased by adding fluthiacet or flumiclorac. Fluthiacet or flumiclorac tank mixtures with halosulfuron or primisulfuron plus prosulfuron did not reduce velvetleaf control as previously reported (Hart 1997). With the exception of halosulfuron, the addition of fluthiacet or flumiclorac did not decrease broadleaf weed control in these greenhouse studies. Adding fluthiacet or flumiclorac to bentazon, imazethapyr, lactofen, or oxasulfuron increased soybean injury 3 DAT compared with bentazon, imazethapyr, lactofen, or oxasulfuron alone (Table 3). Fluthiacet or flumiclorac tank mixtures with bentazon increased velvetleaf, common lambsquarters, and redroot pigweed control compared with bentazon alone 14 DAT. Common lambsquarters, redroot pigweed, and common ragweed control with imazethapyr increased by adding flumiclorac. However, adding fluthiacet to imazethapyr only increased common lambsquarters control. Adding fluthiacet or flumiclorac to lactofen increased velvetleaf, common lambsquarters, and common ragweed control. However, redroot pigweed control with lactofen increased only when flumiclorac was added. Fluthiacet or flumiclorac tank mixtures with 90 oxasulfuron decreased common ragweed control compared with oxasulfuron alone. Similarly, Nelson and Renner (1998) observed decreased common ragweed control in a tank mixture of oxasulfuron plus fluthiacet. Greenhouse results confirm reports that tank mixtures with Protox-inhibiting herbicides, such as fluthiacet and flumiclorac, can increase or decrease weed control. Field Experiments Corn. Adding fluthiacet or flumiclorac to atrazine, dicamba, 2,4—D, bromoxynil, halosulfuron, or primisulfuron plus prosulfuron increased corn injury 7 DAT compared with these herbicides alone (Table 4). Corn injury was greater from flumiclorac tank mixtures with atrazine, bromoxynil, halosulfuron, and 2,4-D compared with fluthiacet tank mixtures. These results support our greenhouse observations that suggested corn injury increased more by the addition of flumiclorac to these herbicides. Fluthiacet or flumiclorac tank mixtures with atrazine, dicamba, or 2,4-D increased velvetleaf control 56 DAT compared with the control provided by atrazine, dicamba, or 2,4-D alone. However, Pennsylvania smartweed control was less than 50% 35 DAT when 2,4-D was tank mixed with fluthiacet or flumiclorac. Broadleaf weed control in the greenhouse and in the field was not reduced when fluthiacet or flumiclorac was tank mixed with atrazine, dicamba, or 2,4-D. However, corn yield did not increase with increased weed control. Schmenk and Kells (1998) reported reduced velvetleaf competition in corn following an atrazine application. Thus, applying atrazine, dicamba, or 2,4—D may reduce velvetleaf competitiveness in corn to a level where increased velvetleaf control from fluthiacet or flumiclorac tank mixtures would not increase com 91 yield. In contrast to our greenhouse studies, velvetleaf, common lambsquarters, and redroot pi gweed control with bromoxynil in the field were not affected by the addition of fluthiacet or flumiclorac. Fluthiacet or flumiclorac tank mixtures with the fast-acting contact herbicide lactofen displayed similar inconsistences. Tank mixtures of fluthiacet or flumiclorac with halosulfuron increased early season cormnon lambsquarters control (data not presented), but by 56 DAT, common lambsquarters control was less than 75%. In contrast to our greenhouse studies, broadleaf weed control did not decrease in the field when fluthiacet or flumiclorac were tank mixed with halosulfuron. F luthiacet or flumiclorac tank mixtures with primisulfuron plus prosulfuron increased common lambsquarters control 56 DAT compared with primisulfuron plus prosulfuron alone. Soybean. Fluthiacet or flumiclorac added to bentazon, imazethapyr, lactofen, or oxasulfuron increased soybean injury 7 DAT compared with these herbicides alone (Table 5). In the greenhouse, soybean injury was similar from tank mixtures of fluthiacet or flumiclorac with bentazon, imazethapyr, lactofen, and oxasulfuron. However, soybean injury in the field was greater from flumiclorac tank mixtures with bentazon or oxasulfirron compared with fluthiacet plus bentazon or oxasulfiiron. Tank mixtures of fluthiacet or flumiclorac with bentazon increased velvetleaf, common lambsquarters, and redroot pi gweed control in the greenhouse (Table 3). Similarly, broadleaf weed control in the field with bentazon plus fluthiacet or flumiclorac was greater than 90% for all species 14 DAT (data not presented). However, late emerging redroot pigweed, common ragweed, and eastern black nightshade reduced season-long 92 control to less than 80% with these tank mixtures (Table 5). In the field, common lambsquarters control with lactofen increased by adding fluthiacet or flumiclorac compared with lactofen alone, but was less than 60% 56 DAT (Table 5). The addition of fluthiacet to lactofen reduced common ragweed control in the field but increased control in the greenhouse compared with lactofen alone. Fluthiacet or flumiclorac tank mixtures with lactofen did not provide season-long broadleaf weed control in the field. Data suggests fluthiacet or flumiclorac tank mixtures with fast—acting contact herbicides, such as lactofen or bromoxynil, may provide fewer benefits than tank mixtures with other herbicides. Despite reports of acifluorfen or bentazon antagonism with imazethapyr (Cantwell et al. 1989), weed control in the greenhouse and in the field was not reduced by fluthiacet or flumiclorac tank mixtures with imazethapyr. Tank mixtures of imazethapyr with fluthiacet or flumiclorac increased common ragweed control and soybean yield in the field compared with imazethapyr alone. Common lambsquarters control with fluthiacet or flumiclorac plus imazethapyr was 90 and 92% 56 DAT, respectively. Similarly, common lambsquarters control with 2 or 3 g ha‘l thifensulfuron (3-[[[[(4—methoxy-6- methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2- thiophenecarboxylic acid) plus 70 g ha" imazethapyr was 85 and 93% 28 DAT, respectively (Simpson and Stoller 1995) Tank mixtures of fluthiacet or flumiclorac with oxasulfuron increased redroot pigweed and common ragweed control in the field yet reduced common ragweed control in the greenhouse compared with oxasulfuron alone. Fluthiacet or flumiclorac tank mixtures with oxasulfuron increased eastern black nightshade control compared with oxasulfuron 93 alone, yet control was less than 60% 35 DAT. Fluthiacet and flumiclorac display activity on various broadleaf weeds. A single application of these herbicides provided exceptional velvetleaf control but insufficient broad-spectrum broadleaf weed control in the field (Fausey and Renner 1998). Likewise, no other postemergence herbicide applied alone provided season-long control of all broadleaf species evaluated. However, tank mixtures of atrazine, dicamba, imazethapyr, and primisulfuron plus prosulfuron with fluthiacet or flumiclorac provided season-long broadleaf weed control of all the species evaluated. These results confirm reports by James et al. (1994) and Kurtz and Pawlak (1993) that adding fluthiacet or flumiclorac to atrazine, bentazon, dicamba, imazethapyr, or 2,4-D improved broadleaf weed control. Corn and soybean exhibited minor leaf necrosis from tank mixtures with fluthiacet or flumiclorac but outgrew the injury by 21 DAT (data not presented). Kapusta et al. (1986) and Wichert and Talbert (1993) reported that leaf necrosis does not affect soybean yield, yet the effect Protox-inhibiting herbicides have on corn yield remains unclear. Corn yield did not increase when weed control increased with fluthiacet or flumiclorac tank mixtures plus atrazine or dicamba. However, soybean yield increased when fluthiacet or flumiclorac was tank mixed with imazethapyr or oxasulfuron compared with imazethapyr or oxasulfuron alone. Tank mixtures including fluthiacet or flumiclorac have several advantages. Increased weed control with fluthiacet or flumiclorac tank mixtures would decrease future weed infestations by reducing weed seed return to the soil seed bank. Tank mixtures including fluthiacet or flumiclorac also provide additional strategies for managing weed resistance. Research investigating fluthiacet or flumiclorac tank mixtures in herbicide resistant com 94 and soybean would be beneficial for weed control programs in these genetically modified crops. ACKNOWLEDGMENTS The authors thank Jason Simon, Gary Powell, and Andy Chomas for their assistance in this research. Appreciation is extended to Valent U.S.A. Corporation and Novartis Crop Protection, Inc. for their financial support. 95 10. ll. 12. LITERATURE CITED Anonymous. 1995. Fluthiacet herbicide technical information bulletin. Greensboro, NC: CIBA-GEIGY Corp., Agricultural Division. Brown, W. B., M. S. DeFelice, and C. S. Hohnan. 1991. Weed control in corn and soybeans with V-23031. Proc. N. Cent. Weed Sci. Soc. 46:40. Cantwell, J. R., R. A. Liebl, and F. W. Slife. 1989. Imazethapyr for weed control in soybean (Glycine max). Weed Technol. 72345-351. Dill, T. R., J. R. James, L. Stahlberg, and E. R. Hill. 1994. Update on the herbicidal activity of CGA-248757 in corn in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:58. Duke, S. 0., J. M. Becerril, T. D. Sherman, J. Lydon, and H. Matsumoto. 1990. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci. 30:367-378. Duke, S. 0., J. Lydon, J. M. Becerril, T. D. Sherman, L. P. Lehnen, Jr., and H. Matsumoto. 1991. Protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 39:465-473. Fausey, J. C. and K. A. Renner. 1998. Broadleaf weed control in soybeans with flumiclorac and CGA-248757 alone and in tank mixtures. Abstr. Weed Sci. Soc. Am. 38:9. Hart S. E. 1997. Interacting effects of MON 12000 and CGA-152005 with other herbicides in velvetleaf (Abutilon theophrasti). Weed Sci. 45:434-438. James, J. R., D. W. Kidder, and T. R. Dill. 1996. Postemergence dicot weed control in soybeans with CGA-277476 applied alone and in combination with other herbicides. Proc. N. Cent. Weed Sci. Soc. 51:132. James, J. R., L. Stahlberg, T. R. Dill, and G. Hill. 1994. Update on the herbicidal activity of CGA-248757 in soybeans in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:129. Kamoshita, K., E. Nagano, S. Hashimoto, R. Sato, R. Yoshida, and H. Oshio. 1993. V-23031-A new herbicide for postemergence weed control in soybeans and field corn. Abstr. Weed Sci. Soc. Am. 53:3. Kapusta, G., S. E. Curvey, and S. T. Autrnan. 1995. Soybean weed control with CGA-248757 and CGA-277476 at three weed growth stages. Research Report N. Cent. Weed Sci. Soc. 52:253-255. 96 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. Kapusta, G., L. A. Jackson, and D. S. Mason. 1986. Yield response of weed-free soybeans (Glycine max) to injury from postemergence herbicides. Weed Sci. 34:304-307. Kurtz, A. R. and J. A. Pawlak. 1992. Postemergence weed control in field corn with V-23031 herbicide. Proc. N. Cent. Weed Sci. Soc. 47:47. Kurtz, A. R. and J. A. Pawlak. 1993. V-23031-A new postemergence herbicide for use in field corn. Abstr. Weed Sci. Soc. Am. 53:9. Lehnen, Jr. L. P., T. D. Sherman, J. M. Becerril, and S. 0. Duke. 1990. Tissue and cellular localization of acifluorfen-induced porphyrins in cucumber cotyledons. Pestic. Biochem. Physiol. 37:239-248. Lich, J. M., K. A. Renner, and D. Penner. 1997. Interaction of glyphosate with postemergence soybean (Glycine max) herbicides. Weed Sci. 45:12-21. Mito, N., R. Sato, M. Miyakado, H. Oshio, and S. Tanaka. 1991. In vitro mode of fluthiacet of N—Phenylimide photobleaching herbicides. Pestic. Biochem. Physiol. 401128-135. Nelson, K. A. and K. A. Renner. 1998. Weed control in wide- and narrow-row soybean (Glycine max) with imazamox, imazethapyr, and CGA-277476 plus quizalofop. Weed Technol. 12:137-144. Porpiglia, P. J ., E. R. Hill, and A. Tally. 1994. CGA-248757 for postemergence broadleaf weed control in corn (Zea mays L.) and soybeans (Glycine max (L.) Merr.). Abstr. Weed Sci. Soc. Am. 34:2. Schmenk, R. E. and J. J. Kells. 1998. Effect of soil applied atrazine and pendimethalin on velvetleaf (Abutilon theophrasti) competitiveness in corn. Weed Technol. 122-47-52. Seefeldt, S. S., J. E. Jensen, and E. P. Fuerst. 1995. Log-logistic analysis of herbicide dose-response relationships. Weed Technol. 92218-227. Simpson, D. M. and E. W. Stoller. 1995. Response of sulfonylurea-tolerant soybean (Glycine max) and selected weed species to imazethapyr and thifensulfuron combinations. Weed Technol. 92582-586. Wesley, T. M. and D. R. Shaw. 1992. Interactions of diphenylether herbicides with chlorimuron and imazaquin. Weed Technol. 61345-35 1. Wichert, R. A. and R. E. Talbert. 1993. Soybean [Glycine max (L.)] response to lactofen. Weed Sci. 41:23-27. 97 26. Young, B. G., S. E. Hart, and L. M. Wax. 1996. Interactions of sethoxydim and corn (Zea mays) postemergence broadleaf herbicides on three annual grasses. Weed Technol. 10:914-922. 98 Table 1. Weed species sensitivities to fluthiacet and flumiclorac in the greenhouse.a Growth Dry weight basis Field ratec Species stage Fluthiacet Flumiclorac Fluthiacet Flumiclorac True leaves — g ha'l Velvetleaf 2 0.1 a 0.7 b 3 b 2 a 4 0.3 a 2.5 b 6 a 8 b 6-7 0.2 a 1.5 b 4 a 5 b Common lambsquarters 6-8 2.9 a 3.0 a 70 b 10 a Redroot pigweed 4-6 0.9 a 2.4 b 22 b 8 a Common ragweed 6-8 1.1 a 3.3 b 27 b 11 a Common cocklebur 4-5 0.8 a 3.0 b 19 b 10 a Eastern black nightshade 5-7 0.4 a 3.4 b 10 a 11 a Wild mustard 5-6 1.2 a 74.1 b 30 a 245 b aAll treatments included 0.25% (v/v) nonionic surfactant (NIS) and 1.0% (WV) 28% urea ammonium nitrate (UAN). Significance between herbicides is only to be compared across rows. Values followed by a common letter are not significantly different at the 5% level. bDry weight reduction represents the g ha'I required to reduce plant growth by 50%, whereas percent of the field use rate represents the percent of either 4 g ha“l fluthiacet or 30 g ha‘1 flumiclorac required to reduce plant grth by 50%. cCalculated based on a field use rate of 4 g ha" fluthiacet and 30 g ha‘l flumiclorac. 99 Table 2. Corn injury 3 d after treatment (DAT) and broadleaf weed control 14 DAT in the greenhouse with fluthiacet or flumiclorac tank mixtures.a Herbicide Rate ZEAMA ABUTH C HEAL AMARE AMBEL g ha" % injury % control Atrazine 210 0 19 31 72 59 Atrazine + fluthiacet 210 +1 5 59 45 78 63 Atrazine + flumiclorac 210 +8 10 74 53 93 71 Dicamba 70 0 30 57 60 61 Dicamba + fluthiacet 70 + 1 3 50 67 65 62 Dicamba + flumiclorac 70 + 8 6 68 77 81 74 2, 4-D 140 5 39 77 32 53 2,4-D + fluthiacet 140 +1 8 61 77 62 60 2,4-D + flumiclorac 140 +8 11 60 78 85 74 Bromoxynil 70 l 43 32 15 67 Bromoxynil + fluthiacet 70 + l 6 63 48 49 65 Bromoxynil + flumiclorac 70 + 8 12 63 57 85 66 Halosulfuron 9 0 71 0 58 75 Halosulfuron + fluthiacet 9 + 1 3 67 21 63 66 Halosulfuron + flumiclorac 9 + 8 6 54 26 70 53 Prinrisulfirron + prosulfuron 10 0 72 51 64 76 Primisulfuron + prosulfuron 10 + 1 4 68 48 75 73 + flutlnacet Primisulfuron + prosulfuron 10 + 8 7 67 52 81 75 + flumrclorac Untreated control — 0 0 0 0 0 LSD (0.05) 2 6 5 8 6 aAll atrazine treatments included 1.0% crop oil concentrate (COC); bromoxynil, dicamba, halosulfuron, primisulfuron plus prosulfuron, and 2, 4-D treatments included 0.25% (v/v) nonionic surfactant (NIS). 100 Table 3. Soybean injury 3 d after treatment (DAT) and broadleaf weed control 14 DAT in the greenhouse with fluthiacet or flumiclorac tank mixtures.a Herbicide Rate GLYMA ABUTH CHEAL AMARE AMBEL g ha‘1 % % control Bentazon 210 1 65 33 35 46 Bentazon + fluthiacet 210 + 1 1.2 96 40 58 49 Bentazon + flumiclorac 210 + 8 12 95 47 80 53 Imazethapyr 1 8 10 66 28 78 46 Imazethapyr + fluthiacet 18 + 1 12 68 36 80 53 Imazethapyr + 18 + 8 12 67 40 93 64 Lactofen 26 1 5 43 20 87 79 Lactofen + fluthiacet 26 + 1 19 67 39 87 89 Lactofen + flumiclorac 26 + 8 20 81 57 97 92 Oxasulfuron 16 7 85 5 1 66 5 5 Oxasulfuron + fluthiacet 16 + l 10 87 44 60 46 Oxasulfuron + flumiclorac 16 + 8 12 81 47 76 42 Untreated control — 0 O 0 0 0 LSD (0.05) 2 6 6 9 8 aAll bentazon treatments included 1.0% crop oil concentrate (COC); imazethapyr and oxasulfuron treatments included 0.25% (v/v) nonionic surfactant (NIS) plus 1.0% (WV) 28% urea ammonium nitrate (U AN); and lactofen treatments included 0.5% (v/v) COC. 101 88 8 8 8 8 m 8 88338 + 883388 882 8 8 8 8 2 8 + 8 38888 + 883338 88 8 8 8 S w v + 8 8388 + 883388 88 8 8 8 8 m 8 88338: ~82 8 8 8 8 8 8 + o8 38838 + 8.888 882 8 8 2 8 8 v + 28 8388 + =8833m 88 8 8 8 8 2 28 88888 :8 8 8 8 8 3 8 + o8 38838 + 38. 88 8 8 8 3 8 a. + o8 8388 + 38 28 8 8 8 8 8 o8 38 882 8 8 8 8 2 8 + 28 38888 + 8885 82: 8 8 8 8 8 a. + o8 8388 + 3385 882 8 8 8 8 _ o8 835 8:: 8 8 8 8 2 8 + 98 38.288 + 838. 8:: 8 8 8 8 : e + 98 8388 + 838. 8:: 8 8 3 8 o 38 838 was 3 68:8 38 83.5 88 was w .828 mm<2< 3880 8.59.. .3208 <2V $36 wows—oi 85:88.: 8:53me 98 b32353: MAUOUV 8955280 :0 nob :\:o._ 33:05 35:58:: 55359 =< u 555v “5:53.: Ban $39 : .32 :5 82 :26 83?: 33 a as a e w : N 30.8 am: 2: o o o o o .I 6::8 38:5 gm 2: :2 2: :2 o I 3::8 8:635 SR c: N: N: S 2 on + 8 88.28:: + 55335 $2 K m: m: o: E v + B 685:: + 85:85 QR o: E mm a n B 83:85 82 a :w mm mm x. 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Fluthiacet or flumiclorac added to fluazifop increased giant foxtail control compared with fluazifop alone. However, barnyardgrass control with fluazifop decreased in the greenhouse when flumiclorac was added. Velvetleaf control with fluthiacet and flumiclorac was greatest 7 DAT when applied to 5 cm tall plants in the field. However, season-long velvetleaf control with both herbicides was greatest when applied to 45 or 60 cm tall plants. In field studies, fluthiacet or flumiclorac applied POST following metolachlor or metolachlor plus atrazine PRE increased velvetleaf control compared to only a PRE application of metolachlor plus atrazine. Similarly, fluthiacet or flumiclorac added to 2,4-D applied POST following metolachlor applied PRE increased velvetleaf control compared to metolachlor followed by 2,4-D alone. Velvetleaf control also increased when fluthiacet or flumiclorac were tank mixed with nicosulfuron plus 105 atrazine, or nicosulfuron plus dicamba applied POST. In soybean, metolachlor plus metribuzin plus clomazone applied PRE, metolachlor applied PRE followed by fluthiacet or flumiclorac applied POST, metolachlor plus metribuzin applied PRE followed by fluthiacet or flumiclorac applied POST, imazethapyr plus fluthiacet or flumiclorac applied POST, glyphosate alone, and tank mixtures of glyphosate with fluthiacet or flumiclorac applied LATE POST controlled giant foxtail, common lambsquarters, redroot pigweed, and velvetleaf in 1997. However, only metolachlor plus metribuzin applied PRE followed by fluthiacet or flumiclorac applied POST and imazethapyr plus fluthiacet or flumiclorac applied POST controlled these weeds in 1998. Nomenclature: Atrazine, 6-chloro-N-ethyl-N’-(1-rnethylethyl)-1,3,5-triazine-2,4- diamine; bromoxynil, 3,5-dibromo-4-hydroxybenzonitrile; 2,4-D, (2,4- dichlorophenoxy)acetic acid; clethodim, (E,E)-(:t)-2-[1-[[(3-chloro-2- propenyl)oxy]imino]butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one; clomazone, 2-[(2-chlorophenyl)methyl]4,4-dimethyl-3-isoxazolidinone; dicamba, 3,6- dichloro-Z-methoxybenzoic acid; fluazifop, (i)-2-[4-[[5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid; fluthiacet, methyl[[2-chloro-4-fluoro-5- [(tetrahydro-3-oxo- 1H, 3H—[ 1 ,3 ,4]thiadiazolo[3,4-a]pyridazin-1- ylidene)amino]phenyl]thio]acetate; flumiclorac, pentyl[2-chloro-4-fluoro-5-(1,3,4,5,6,7- hexahydro-l,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid; glyphosate (N- (phosphonomethyl)glycine); imazethapyr, 2-[4,5~dihydro-4-methyl-4-(1-methylethyl)-5- oxo-1H-imidazol-2-y1]-5-ethyl-3-pyridinecarboxylic acid; metolachlor, 2-chloro-N-(2- ethyl-6-methy1phenyl)—N—(2-methoxy- l -methylethyl)acetamide; metribuzin, 4-amino-6- (1 ,1-dimethylethyl)-3-(methylthio)-1 ,2,4-t1iazin-5(4H)-one; nicosulfuron (2-[[[[(4,6- 106 dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N,N-dimethyl-B- pyridinecarboxamide); oxasulfuron, 2-[[[[(4,6-dimethyl—2-pyrimidinyl)- amino]carbonyl]amino]sulfonyl] benzoic acid, 3-oxetany1 ester; quizalofop (:t)-2-[4-[(6- chloro-Z-quinoxalinyl)oxy]phenoxy]propanoic acid; sethoxydim, 2-[1- (ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one; 2,4-D, (2,4- dichlorophenoxy)acetic acid; common lambsquarters, Chenopodium album L. # CHEAL; redroot pigweed, Amaranthus retroflexus L. # AMARE; barnyardgrass, Echinochloa Crus-galli L. Beauv. ECHCG; giant foxtail, Setariafaberi Herrm. # SETFA; velvetleaf, Abutilon theophrasti Medik. #' ABUTH; wild mustard, Brassica kaber (D.C.) L.C. Wheeler # SINAR; corn, Zea mays L. # ZEAMA; soybean, Glycine max (L.) Merr. # GLYMA. Key Words: Antagonism, herbicide interaction, Protox, ABUTH, AMARE, CHEAL, SETFA, GLYMA, ZEAMA. Abbreviations: COC, crop oil concentrate; DAP, days after planting; DAT, days after treatment; LATE POST, late postemergence; NIS, nonionic surfactant; POST, postemergence; Protox, protoporphyrinogen oxidase; PRE, preemergence; UAN, 28% urea ammonium nitrate. 'Letters following this symbol are a WSSA-approved computer code from Composite List of Weeds, Revised 1989. Available from WSSA, 810 East 10th Street, Lawrence, KA 66044-8897. 107 INTRODUCTION Fluthiacet and flumiclorac are cyclic imide herbicides that effectively control velvetleaf, one of the most troublesome broadleaf weeds in corn and soybean (Porpiglia et a1. 1994; Kamoshita et a1. 1993). These selective herbicides control weeds by inhibiting the protoporphyrinogen oxidase (Protox) enzyme in susceptible plants (Duke et a1. 1990; Duke et al. 1991; Mito et al. 1991). F luthiacet and flumiclorac provided greater than 96% season-long velvetleaf control (Brown et a]. 1991; Kapusta et al. 1995). However, season-long common cocklebur control with fluthiacet was 83% (Kapusta et al. 1995), and Pennsylvania smartweed control with flumiclorac was 60% (Brown et al. 1991). Broad-spectrum weed control is commonly achieved by tank mixing herbicides. Tank mixtures including fluthiacet or flumiclorac may enhance velvetleaf control and provide more consistent broadleaf weed control compared with the tank mix partner alone (Dill et a1. 1994; James et al. 1994; Kurtz and Pawlak 1992). Understanding herbicide performance in tank mixtures is important when creating weed management programs (Young et al. 1996). Giant foxtail control with sethoxydim (2-[1-(ethoxyimino)butyl]-S- [2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one) was not affected by the addition of fluthiacet or flumiclorac (James et al. 1994; Young et al. 1996); however, shattercane (Sorghum bicolor (L.) Moench) control was reduced (Young et al. 1996). Similarly, large crabgrass (Digitaria sanguinalis (L.) Scop.) control with sethoxydim was not affected by the addition of fluthiacet, however, control was reduced by adding flumiclorac. F luthiacet or flumiclorac tank mixtures with glyphosate (N- (phosphonomethyl)glycine) increased velvetleaf and common ragweed control compared 108 with glyphosate alone (Lich et a1. 1997). However, adding fluthiacet to oxasulfuron reduced common ragweed control compared with oxasulfuron alone (Nelson and Renner 1998) Potential benefits of fluthiacet and flumiclorac include low use rates, short-half lives, resistance management, and the ability to broaden the spectrum of other herbicides (Anonymous 1995). Research investigating broad-spectrum weed control programs in corn and soybean with fluthiacet or flumiclorac is limited. Field research has not determined the most effective time to apply fluthiacet or flumiclorac in corn or soybean or their performance with other postemergence herbicides. Therefore, the objective of this research was to evaluate broad-spectrum weed control programs in corn and soybean that include fluthiacet and flumiclorac. MATERIALS AND METHODS Greenhouse Experiments Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures. Giant foxtail and barnyardgrass seed was obtained fi'om a commercial seed supplier-z. Seeds were planted in BACCTO3 potting soil in 946 m1 plastic pots. Environmental conditions were maintained within a greenhouse at 27 :t 5 C. Plants were grown under a 16-h photoperiod of natural and supplemental high pressure sodium lighting with a photosynthetic photon 2Seed, V & J Seed Farms, PO. Box 82, Woodstock, IL 60098. 3BACCTO professional planting mix, Michigan Peat Co., PO. Box 98129, Houston, TX 77098. 109 flux density of 1000 ,umol m‘2 5". Plants were thinned to 1 plant pot“, fertilized with 50 ml of a water-soluble fertilizer solution (400 ppm N, 400 ppm P205, and 400 ppm K20), and watered as needed. Herbicides were applied with a continuous belt-linked sprayer fitted with an 8001E flat-fan nozzle4 traveling at 1.53 km h" and delivering 234 L ha‘l at 193 kPa of pressure. The experiment was a completely randomized design with four replications. Giant foxtail and barnyardgrass were visually evaluated in each experiment 3, 7 and 14 d after treatment (DAT). Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 indicating plant death. Evaluations represented visual stunting, chlorosis, and necrosis. Experiments evaluated giant foxtail and barnyardgrass control with tank mixtures including fluthiacet and flumiclorac. Treatments included an untreated control, 18 g ha‘l imazethapyr, 12 g ha" quizalofop, 52 g ha'l sethoxydim, 35 g ha'1 clethodim, and 52 g ha'l fluazifop applied alone and in a tank mixture with 1 g ha" fluthiacet or 8 g ha" flumiclorac. All treatments were applied with crop oil concentrate5 (COC) (1 .0% v/v). Giant foxtail plants were 10 cm tall with three to four leaves, and barnyardgrass plants were 10 cm tall with two to three leaves at application. Giant foxtail and barnyardgrass were visually evaluated for phytotoxicity 7 and 14 DAT. Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 signifying plant death. Evaluations represented visual stunting, chlorosis, and necrosis. 4Teejet flat-fan nozzles, Spraying Systems Co., North Avenue and Schmale Road, Wheaton, IL 60532. 5Herbimax, 83% petroleum oil, 17% surfactant, Loveland Industries Inc., PO. Box 1289, Greeley, CO 80632. 110 Field Experiments Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures. Research was conducted at the Michigan State University Research Farm in East Lansing, MI in 1997. The soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aerie Ochraqualfs) with 2.8% organic matter and a pH of 6.6. The site was fall moldboard plowed with secondary tillage consisting of two field cultivations at planting. ‘Conrad’ soybean was planted in 76-cm rows at 345,000 seed ha". Plots were 3 m wide by 10.6 min length. The experiment was a randomized complete block with four replications. Treatments included an untreated control, 140 g ha’l clethodim, and 210 g ha’l fluazifop applied alone and in a tank mixture with 5 g ha‘l fluthiacet or 45 g ha‘l flumiclorac. All treatments included COC5 (1 .0% v/v). Herbicides were applied on June 17, 1997, 35 d after planting (DAP), with a compressed air tractor-mounted sprayer traveling at 6.3 km h‘1 and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At application, soybean plants were 8 to 10 cm tall with one fully developed trifoliolate; and giant foxtail and barnyardgrass plants were 1 to 12 cm tall with one to five leaves. Giant foxtail and barnyardgrass control was evaluated 7, 14, and 28 DAT. Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 signifying plant death. Evaluations represented visual stunting, chlorosis, and necrosis. Velvetleaf Control. Experiments were conducted at the Michigan State University Research Farm in East Lansing, MI in 1996 and 1997. The soil was a Capac sandy loam (fine-loamy, mixed mesic Aeric Ochraqualfs) with 2.5 and 2.4% organic matter in 1996 111 and 1997, respectively. The soil pH was 6.5 in 1996 and 1997. Sites were spring chisel plowed with secondary tillage consisting of two field cultivations at planting. Dekalb6 ‘404 SR’ corn was planted in 76-cm rows at 62,000 seed ha". Plots were 3 m wide by 9.1 m in length. The experiment was a randomized complete block with four replications. Treatments included 4 and 5 g ha“ fluthiacet or 30 and 45 g ha'l flumiclorac applied with COC5 0.5% (v/v). Herbicides were applied on June 12, July 2, and July 9, 1996 and June 10, June 27, and July 1, 1997 with a compressed air tractor-mounted sprayer traveling at 6.3 km h'1 and delivering 178 L ha'l at 207 kPa of pressure. Treatments were applied with 8003 flat- fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At application, velvetleaf plants were 2 cm tall and from cotyledon to two-leaf stage; 45 cm tall with eight to 10 leaves; and 60 cm tall with ten to 12 leaves. Corn injury was visually evaluated 3, 7, and 14 DAT. Velvetleaf control was evaluated 7 and 14 DAT, and 21 d after the third application timing. Visual ratings were based on a scale from 0 to 100%, with 0 indicating no effect and 100 signifying plant death. Corn injury and velvetleaf control evaluations represented visual stunting, chlorosis, and necrosis. Annual Weed Control in Corn. Experiments were conducted at the Michigan State University Research Farm at East Lansing, MI and at the Michigan State Horticultural Research Station at Clarksville, MI in 1998. The East Lansing soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aeric Ochraqualfs) with 2.5% organic matter and a pH of 6.5. The Clarksville soil was a Lapeer sandy loam (coarse-loamy, mixed mesic 6Corn, DEKALB Genetics Corporation, 3100 Sycamore Road Dekalb, IL 60115. 112 Mollic Haplaquepts) with 1.9% organic matter and a pH of 6.8. Sites were spring moldboard plowed with secondary tillage consisting of two field cultivations at planting. Dekalb6 ‘493 RR’ corn was planted in 76-cm rows at 62,000 seed ha". Plots were 3 m wide by 10.6 m in length. The experiment was a randomized complete block with four replications. Treatments included a weed-free and an untreated control. All POST atrazine treatments included COC5 (1.0% v/v). All 2,4—D, dicamba, and bromoxynil treatments included Activator 9O7 (NIS) (0.25% v/v). Fluthiacet, flumiclorac, and glyphosate treatments included NIS7 plus UAN (0.25 + 1.0% v/v). PRE herbicide applications were applied on May 26, 1998 at East Lansing and May 19, 1998 at Clarksville. POST herbicide applications were applied at East Lansing and Clarksville on June 26, 1998 and June 18, 1998, 31 and 30 DAP, respectively. LATE POST applications were applied at East Lansing and Clarksville on June 29, 1998 and June 23, 1998, respectively. All herbicide treatments were applied with a compressed air tractor-mounted sprayer traveling at 6.3 km h'l and delivering 178 L ha‘l at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At the time of POST applications corn plants were 25 to 30 cm tall with five collars; giant foxtail plants were 1 to 15 cm tall with one to four leaves; common lambsquarters plants were 1 to 10 cm tall with two to 18 leaves; redroot pigweed plants were 1 to 8 cm tall and from cotyledon to ten leaves; and velvetleaf plants were 1 to 10 cm tall and from cotyledon to six leaves. At the time of LATE POST 7Activator 90, nonionic surfactant, a mixture of alkyl polyoxyethylene ether and fatty acids, Loveland Industries, Inc., PO. Box 1289, Greeley, CO 80632. 113 application corn plants were 30 to 38 cm tall with six collars; giant foxtail plants were 1 to 22 cm tall with one to six leaves; common lambsquarters plants were 1 to 15 cm tall with two to 30 leaves; redroot pigweed plants were 1 to 18 cm tall with two to 12 leaves; and velvetleaf plants were 1 to 18 cm tall with two to eight leaves. Corn injury was visually evaluated 7 and 14 DAT. Weed control was evaluated for each species 14, 28, and 56 DAT. Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 signifying plant death. Corn injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. The two middle rows from each plot were harvested with a Massey 108 small-plot combine. Corn yield was adjusted to 15.5% moisture. Annual Weed Control in Soybean. Experiments were conducted at the Michigan State University Research Farm at East Lansing, MI in 1997 and 1998. The soil was a Capac sandy clay loam (fine-loamy, mixed mesic Aeric Ochraqualfs) with 2.8 and 4.2% organic matter in 1997 and 1998, respectively. The soil pH was 6.6 and 6.3 in 1997 and 1998, respectively. Sites were fall chisel plowed with secondary tillage consisting of two field cultivations at planting. Asgrow9 ‘2701 RR’ soybean was planted in 76-cm rows at 345,000 seed ha". Plots were 3 m wide by 10.6 m in length. The experiment was a randomized complete block with four replications. Treatments included a weed-free and an untreated control. All fluthiacet, flumiclorac, imazethapyr, oxasulfuron, and glyphosate treatments were applied with NIS7 plus UAN (0.25 + 1.0% v/v). All clethodim treatments included COC5 (1 .0% v/v). 8Kincaid Equipment Manufacturing, PO. Box 400, Haven, KS 47543. 9Soybean, Asgrow Seed Company, PO. Box 7570, Des Moines, IA 50322. 114 PRE herbicide applications were applied on May 13, 1997 and 1998. POST herbicide applications were applied on June 17, 1997 and June 8, 1998, 35 and 26 DAP, and LATE POST applications were applied on June 22, 1997 and June 14, 1998. All herbicide treatments were applied with a compressed air tractor-mounted sprayer traveling at 6.3 km h" and delivering 178 L ha" at 207 kPa of pressure. Treatments were applied with 8003 flat-fan nozzles spaced 51 cm apart and 48 cm above the weed canopy. At the time of POST applcations soybean plants were 10 to 14 cm tall with two fully developed trifoliolates; giant foxtail plants were 1 to 15 cm tall and from one to four leaves; common lambsquarters plants were 1 to 10 cm tall with two to 22 leaves; redroot pi gweed plants were 1 to 8 cm tall and from cotyledon to ten leaves; and velvetleaf plants were 1 to 10 cm tall and from cotyledon to five leaves. At the time of LATE POST applications soybean plants were 15 to 20 cm tall with two to three trifoliolates; giant foxtail plants were 1 to 20 cm tall and fi'om one to six leaves; common lambsquarters plants were 1 to 15 cm tall with four to 26 leaves; redroot pigweed plants were 1 to 10 cm tall with two to 12 leaves; and velvetleaf plants were 1 to 13 cm tall and from cotyledon to seven leaves. Soybean injury was visually evaluated 7 and 14 DAT. Weed control was evaluated for each species 14, 28, and 56 DAT. Visual ratings were based on a scale from O to 100%, with 0 indicating no effect and 100 signifying plant death. Soybean injury and weed control evaluations represented visual stunting, chlorosis, and necrosis. The two middle rows from each plot were harvested with a Massey 108 small-plot combine. Soybean yield was adjusted to 13% moisture. 115 Statistical Analyses All experiments were repeated over time, and data were analyzed using analysis of variance (ANOVA). When data for individual experiments revealed no treatment by time interaction experiments were combined. Means were separated by Fisher’s protected least significant difference test (LSD) at the 5% level. RESULTS AND DISCUSSION Annual Grass Control with Fluthiacet and Flumiclorac Tank Mixtures. F luthiacet tank mixed with imazethapyr, quizalofop, sethoxydim, clethodim, and fluazifop did not reduce giant foxtail or barnyardgrass control with these herbicides in the greenhouse (Table 1). Similarly, when flumiclorac was added to imazethapyr, quizalofop, sethoxydim, or clethodim giant foxtail and barnyardgrass control was not reduced (Table 1). Giant foxtail control with flumiclorac plus fluazifop increased by 4%, yet barnyardgrass control decreased by 32% in the greenhouse when compared with fluazifop alone. Similarly, Young et al. (1996) reported giant foxtail and large crabgrass control with sethoxydim was not affected by the addition of fluthiacet; however, large crabgrass control with sethoxydim was reduced by the addition of flumiclorac. Adding fluthiacet or flumiclorac to clethodim or fluazifop did not reduce giant foxtail or barnyardgrass control in the field when compared with clethodim or fluazifop alone (Table 2). Differing results between the greenhouse and field may be explained by flumiclorac and fluazifop application rates; both were applied in the greenhouse at one-fourth the application rate used in the field. Thus, increased herbicide rates in the field may have 116 overcome any antagonism between flumiclorac and fluazifop. Regardless, our results suggest that fluthiacet and flumiclorac do not antagonize giant foxtail or barnyardgrass control by imazethapyr, quizalofop, sethoxydim, or clethodim. Weed Control Programs. Velvetleaf Control. Velvetleaf control was equivalent between 4 and 5 g ha‘l fluthiacet and 30 and 45 g ha‘l flumiclorac in the field at all three application timings, thus the data for each herbicide is combined over application rates. Fluthiacet and flumiclorac provided greater than 80% control of 60 cm-tall velvetleaf plants (Table 3). Velvetleaf control with fluthiacet and flumiclorac was greatest 7 DAT when applied to 5-cm tall plants in the field. However, season-long velvetleaf control with both herbicides was greatest when applied to 45 or 60 cm tall plants. Because fluthiacet and flumiclorac have no soil activity, delaying herbicide application allowed more velvetleaf to emerge prior to herbicide application. Similarly, Tharp and Kells (1997) reported that delaying glyphosate or glufosinate (2-amino-4-(hydroxymethylphosphinyl)butanoic acid) applications, which also have no soil activity, enhanced season-long weed control. Annual Weed Control in Corn. Corn exhibited leaf necrosis from tank mixtures including fluthiacet or flumiclorac (Table 4), but injury was no longer evident by 21 DAT (data not presented). Giant foxtail, common lambsquarters, and redroot pigweed were controlled by all of the herbicide programs evaluated. A POST application of fluthiacet or flumiclorac following metolachlor or metolachlor plus atrazine applied PRE increased velvetleaf control 56 DAT compared with metolachlor plus atrazine applied PRE (Table 4). Adding fluthiacet or flumiclorac to 2,4-D applied POST following metolachlor 117 applied PRE increased velvetleaf control compared with metolachlor followed by 2,4-D alone. Velvetleaf control also increased when fluthiacet or flumiclorac were added to nicosulfuron plus atrazine, or nicosulfuron plus dicamba applied POST. Corn yield in the metolachlor applied PRE followed by fluthiacet plus atrazine applied POST treatment was greater than yield in the metolachlor plus atrazine applied PRE followed by fluthiacet applied POST. Corn yield with metolachlor applied PRE followed by 2,4-D applied POST, nicosulfuron plus bromoxynil applied POST, and glyphosate alone and tank mixtures of glyphosate with fluthiacet or flumiclorac applied LATE POST had lower yields when compared with the weed-free control. The yield reduction in the metolachlor applied PRE followed by 2,4-D applied POST and the nicosulfuron plus bromoxynil applied POST treatments resulted from a lack of velvetleaf control. However, corn yield did not increase with increased velvetleaf control from tank mixtures of fluthiacet or flumiclorac with nicosulfuron plus atrazine or dicamba. Schmenk and Kells (1998) reported reduced velvetleaf competitiveness in corn following an atrazine application. Thus, applying atrazine or dicamba may reduce velvetleaf competitiveness to a level where increased velvetleaf control from tank mixtures including fluthiacet or flumiclorac would not increase corn yield. Because reduced corn yield cannot be attributed to a lack of weed control in the glyphosate and glyphosate tank mixture treatments, yield loss may be attributed to weed competition. All glyphosate treatments were applied LATE POST, three to five days alter POST herbicide treatments. Our data suggests weed competition during this time period reduced corn yield. Annual Weed Control in Soybean. Soybean exhibited leaf necrosis from tank mixtures with fluthiacet or flumiclorac, but injury was not evident by 21 DAT (data not presented). 118 Kapusta et al. (1986) and Wichert and Talbert (1993) reported that leaf necrosis from Protox-inhibiting herbicides did not reduce soybean yield. In 1997, metolachlor plus metribuzin plus clomazone applied PRE, metolachlor applied PRE followed by fluthiacet or flumiclorac applied POST, metolachlor plus metribuzin applied PRE followed by fluthiacet or flumiclorac applied POST, imazethapyr plus fluthiacet or flumiclorac applied POST, or glyphosate, and glyphosate tank mixtures with fluthiacet or flumiclorac applied LATE POST provided season-long, common lambsquarters, redroot pigweed, and velvetleaf control (Table 5). However, only metolachlor plus metribuzin applied PRE followed by fluthiacet or flumiclorac applied POST, or imazethapyr plus fluthiacet or flumiclorac applied POST controlled these weeds in 1998 (Table 6). Precipitation affects herbicide performance (Wanamarta and Penner 1989). The first rainfall greater than 2.5 cm occurred 5 and 18 d after PRE application in 1997 and 1998, respectively. The total PRE herbicide program of metolachlor plus metribuzin plus clomazone provided adequate season-long weed control in 1997, but the lack of rainfall for two weeks after herbicide application resulted in insufficient weed control in 1998. Alternatively, the total POST treatments of fluthiacet or flumiclorac plus imazethapyr resulted in season-long weed control both years. Overall, PRE applications followed by POST applications and total POST herbicide programs provided more consistent weed control when compared with total PRE herbicide programs. Previous research showed tank mixtures of fluthiacet or flumiclorac plus imazethapyr or oxasulfirron increased broadleaf weed control compared with imazethapyr or oxasulfuron alone (Fausey and Renner 1998). However, acceptable broad-spectrum weed 119 control was only achieved by fluthiacet or flumiclorac tank mixtures with imazethapyr. F luthiacet or flumiclorac tank mixtures with oxasulfuron and quizalofop provided less than 80% giant foxtail control in 1997 and less than 60% redroot pigweed control in 1998, and soybean yield was reduced compared with the weed-free control in 1997 and 1998. Glyphosate and glyphosate tank mixtures with fluthiacet or flumiclorac provided season-long weed control with soybean yields equal to the weed-free control in 1997. However, the addition of fluthiacet to glyphosate reduced redroot pigweed control compared with glyphosate alone. Weed control with glyphosate alone and in tank mixtures including fluthiacet or flumiclorac provided excellent weed control 14 DAT in 1998 (data not presented). However, dry conditions followed by rainfall after herbicide application resulted in late emerging weeds. These weeds reduced soybean yield in the glyphosate treatments when compared with the weed-fiee control. Field results suggest herbicide selection and time of application are critical to assure maximum crop yield. Cantwell et al. (1989) and Wesley and Shaw (1992) reported that tank mixtures with Protox-inhibiting herbicides may increase or decrease weed control. Thus, careful consideration must be given when choosing a tank mix partner for fluthiacet or flumiclorac. These herbicides control velvetleaf and have activity on common lambsquarters and redroot pigweed. However, a single fluthiacet or flumiclorac application in the field provided sufficient broad-spectrum weed control when applied following a PRE application of metolachlor plus atrazine in corn or a PRE application of metolachlor plus metribuzin in soybean. Likewise, a PRE application of metolachlor followed by atrazine or 2,4-D tank mixed with fluthiacet or flumiclorac provided season- 120 long broadleaf weed control in corn. James et al. (1994) and Kurtz and Pawlak (1993) reported that adding fluthiacet or flumiclorac to several postemergence herbicides enhanced broadleaf weed control. Fluthiacet or flumiclorac tank mixtures with nicosulfuron plus atrazine or nicosulfuron plus dicamba in corn and imazethapyr in soybean provided season-long broadleaf weed control. Weed control programs that include fluthiacet or flumiclorac have several benefits over current commercial standards. These herbicides provide unprecedented postemergence velvetleaf control and have the flexibility to be used in corn and soybean. Tank mixtures including these herbicides also provide an additional mode of action for managing weed resistance. Further research should investigate crop tolerance and weed control programs with fluthiacet and flumiclorac in herbicide resistant corn and soybean. ACKNOWLEDGMENTS The authors thank Gary Powell for his assistance in this research. Appreciation is extended to Valent U.S.A. Corporation and Novartis Crop Protection, Inc. for their financial support. 121 10. ll. 12. LITERATURE CITED Brown, W. B., M. S. DeFelice, and C. S. Holman. 1991. Weed control in corn and soybeans with V-23031. Proc. N. Cent. Weed Sci. Soc. 46:40. Cantwell, J. R., R. A. Liebl, and F. W. Slife. 1989. Imazethapyr for weed control in soybean (Glycine max). Weed Technol. 7 2345-35 1. Dill, T. R., J. R. James, L. Stahlberg, and E. R. Hill. 1994. Update on the herbicidal activity of CGA-248757 in corn in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:58. Duke, S. O., J. M. Becerril, T. D. Sherman, J. Lydon, and H. Matsumoto. 1990. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci. 30:367-378. F ausey, J. C. and K. A. Renner. 1998. Broadleaf weed control in soybeans with flumiclorac and CGA-248757 alone and in tank mixtures. Abstr. Weed Sci. Soc. Am. 38:9. James, J. R., L. Stahlberg, T. R. Dill, and G. Hill. 1994. Update on the herbicidal activity of CGA-248757 in soybeans in the Midwest. Proc. N. Cent. Weed Sci. Soc. 49:129. Kamoshita, K., E. Nagano, S. Hashimoto, R. Sato, R. Yoshida, and H. Oshio. 1993. V-23031-A new herbicide for postemergence weed control in soybeans and field corn. Abstr. Weed Sci. Soc. Am. 5323. Kapusta, G., S. E. Curvey, and S. T. Autman. 1995. Soybean weed control with CGA-248757 and CGA-277476 at three weed growth stages. Research Report N. Cent. Weed Sci. Soc. 52:253-255. King, C. A. and L. R. Oliver. 1992. Application rate and timing of acifluorfen, bentazon, chlorimuron, and imazaquin. Weed Technol. 6:526-534. Kurtz, A. R. and J. A. Pawlak. 1992. Postemergence weed control in field corn with V-23031 herbicide. Proc. N. Cent. Weed Sci. Soc. 47:47. Lich J. M., K. A. Renner, and D. Penner. 1997. Interaction of glyphosate with postemergence soybean (Glycine max) herbicides. Weed Sci. 45:12-21. Mito, N., R. Sato, M. Miyakado, H. Oshio, and S. Tanaka. 1991. In vitro mode of action of N-Phenylimide photobleaching herbicides. Pestic. Biochem. Physiol. 40: 128-135. 122 13. 14. 15. l6. 17. 18. 19. Nelson, K. A. and K. A. Renner. 1998. Weed control in wide- and narrow-row soybean (Glycine max) with imazamox, imazethapyr, and CGA-277476 plus quizalofop. Weed Technol. 12:137—144. Porpiglia, P. J ., E. R. Hill, and A. Tally. 1994. CGA-248757 for postemergence broadleaf weed control in corn (Zea mays L.) and soybeans (Glycine max (L.) Merr.). Abstr. Weed Sci. Soc. Am. 34:2. Sander, K. W. and P. J. Porpiglia. 1996. GOA-248757 combinations for broadleaf weed control in soybeans. Proc. N. Cent. Weed Sci. Soc. 51:132. Schmenk, R. E. and J. J. Kells. 1998. Effect of soil applied atrazine and pendimethalin on velvetleaf (Abutilon theophrasti) competitiveness in corn. Weed Technol. 12:-47-52. Tharp, B. E. and J. J. Kells. 1997. Weed management strategies in glufosinate resistant and glyphosate resistant corn. Proc. N. Cent. Weed Sci. Soc. 52:64. Wesley, T. M. and D. R. Shaw. 1992. Interactions of diphenylether herbicides with chlorimuron and imazaquin. Weed Technol. 62345-351. Young, B. G., S. E. Hart, and L. M. Wax. 1996. Interactions of sethoxydim and corn (Zea mays) postemergence broadleaf herbicides on three annual grasses. Weed Technol. 10:914-922. 123 Table 1. Giant foxtail and barnyardgrass control with fluthiacet or flumiclorac tank mixtures in the greenhouse 14 d after treatment.3 Herbicide Rate Giant foxtail Bamyardgrass g ha" % control Imazethapyr 1 8 1 9 1 8 Imazethapyr + fluthiacet 18 + 1 23 20 Imazethapyr + flumiclorac 18 + 8 32 44 Quizalofop 12 98 98 Quizalofop + fluthiacet 12 + 1 98 97 Quizalofop + flumiclorac 12 + 8 97 98 Sethoxydim 52 8 1 89 Sethoxydim + fluthiacet 52 + 1 84 93 Sethoxydim + flumiclorac 52 + 8 86 94 Clethodim 35 86 98 Clethodim + fluthiacet 35 + 1 86 98 Clethodim + flumiclorac 35 + 8 86 97 F luazifop 52 8O 95 Fluazifop + fluthiacet 52 + 1 83 95 Fluazifop + flumiclorac 52 + 8 84 63 Untreated control —— O O LSD (0.05) 2 a All treatments received 1.0% (v/v) crop oil concentrate (COC). 124 Table 2. Giant foxtail and barnyardgrass control with fluthiacet or flumiclorac tank mixtures in the field 28 d after treatment.3 Herbicide Rate Giant foxtail Bamyardgrass g ha'l % control Clethodim 140 100 100 Clethodim + fluthiacet 140 + 5 100 98 Clethodim + flumiclorac 140 + 45 100 100 Fluazifop 210 100 99 Fluazifop + fluthiacet 210 + 5 99 100 Fluazifop + flumiclorac 210 + 45 99 99 Untreated control — O O LSD (0.05) 2 3 a All treatments included 1.0% (v/v) crop oil concentrate (COC). 125 Table 3. 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