Commercialization of florpyrauxifen-benzyl as Loyant® in 2018 as a synthetic auxin herbicide in rice was followed by soybean injury due to off-target movement of spray applications in the mid-southern United States. Concerns surrounding off-target movement led to the exploration of an alternative application method to help alleviate the issue. Field experiments were conducted in 2020 and 2021 to explore the likelihood of a reduction in soybean injury following applications of florpyrauxifen-benzyl coated on urea in narrow- and wide-row soybean systems and to determine the likelihood of volatilization from this novel application method. Florpyrauxifen-benzyl spray-applied at 0.18 g ai ha-1 caused greater than 60% injury, while coating the herbicide on urea at 5.63 g ai ha-1 never exceeded 30% injury in narrow-row soybean. Similarly, florpyrauxifen-benzyl spray-applied at 0.18 g ai ha-1 caused greater than 50% injury while coating the herbicide on urea at 5.63 g ai ha-1 never exceeded 30% injury in wide-row soybean. As soybean injury increased, relative yield decreased in both narrow- and wide-row soybean. Spray-applied florpyrauxifen-benzyl decreased relative soybean groundcover, yield components, and soybean survival rate as the herbicide rate increased, whereas coating the herbicide on urea resulted in little to no decrease in both narrow- and wide-row soybean assessments. No negative impacts on relative yield and yield components of soybean from florpyrauxifen-benzyl coated on urea indicates that even though visible injury may persist, there is a low likelihood of any yield losses associated with the herbicide exposure using this application method. Additionally, coating the florpyrauxifen-benzyl on urea did not increase the likelihood of volatilization under any of the evaluated soil moisture conditions. Overall, applying florpyrauxifen-benzyl coated on urea is likely to be a safer application method and can reduce soybean injury compared to spray applying the herbicide when favorable off-target movement conditions exist.

Dicamba and 2,4-D are postemergence herbicides widely used to control broadleaf weed species in crop and non-crop areas in the United States. Currently, multiple formulations of 2,4-D and dicamba are available on the market. Even though the active ingredient is the same, the chemical formulation may vary, which can influence the volatility potential of these herbicides. Therefore, the objective of this study was to evaluate the response of soybean, cotton, and tobacco plants exposed to vapors of 2,4-D and dicamba formulations alone or mixed in humidomes for 24 h. Humidome studies were conducted in an open pavilion at the Lake Wheeler Turfgrass Field Lab of the North Carolina State University in Raleigh, NC. Dicamba and mixture treatments injured and caused a reduction in the height of soybean. Injury varied from 55% to 70%, and average plant height was 8.8 cm shorter compared with untreated control plants. Treatments with 2,4-D caused the least injury to soybean (≤21%), and differences among formulations were identified (dimethylamine > choline > dimethylamine-monomethylamine). However, soybean height was not affected by 2,4-D treatments. No differences between treatments were observed when herbicides were applied to cotton. The greatest injury to tobacco (23.3%) was caused by dicamba dimethylamine. Overall, the effect of 2,4-D and dicamba vapor was species-specific and formulation-dependent. Additionally, environmental conditions in the humidomes may have played a major role on the outcome of this study.

Dicamba was labeled in dicamba-resistant cotton (Gossypium hirsutum L.) and soybean [Glycine max (L.) Merr.] in 2017, resulting in a record number of off-target complaints. To address off-target movement via volatilization, experiments were conducted to evaluate the effectiveness of potassium tetraborate tetrahydrate (KBo) as a volatility-reducing agent (VRA) with dicamba. Low-tunnel experiments examined: (1) whether KBo functions as a dicamba VRA, (2) the relationship between KBo concentration and dicamba volatilization, (3) the effectiveness of KBo compared with potassium acetate as a VRA, and (4) the impact of KBo on dicamba volatilization with and without glufosinate. In a large-scale trial (0.4-ha plots), the effectiveness of KBo in reducing dicamba volatilization was quantified relative to a commercial dicamba application labeled for use in 2020. The addition of KBo to dicamba reduced volatility over dicamba alone and a dicamba plus potassium acetate premix. As KBo concentration increased in the dicamba spray solution, volatilization was exponentially reduced. Dicamba volatilization with the addition of KBo at 0.01 M was comparable to dicamba plus potassium acetate at 0.05 M. Potassium tetraborate tetrahydrate was more effective than potassium acetate at reducing volatility of a dicamba plus glufosinate mixture. In large-scale experiments over a 30-h period, the addition of KBo to a diglycolamine plus glyphosate mixture lowered dicamba volatilization 82% to 89% over the herbicide mixture alone. Overall, the addition of KBo to dicamba appears promising as a VRA compared with what is commercially available.

Immediately following postemergence application, similar quantities of metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one] were retained on the foliage of downy brome (Bromus tectorum L. # BROTE) and winter wheat (Triticum aestivum L.). Three days following treatment, more metribuzin was present on the surface of the foliage of downy brome than of winter wheat and similar quantities of metribuzin had been absorbed into the interior of the foliage of both species. Fourteen days after treatment, metribuzin had disappeared from the surfaces of the foliage of both species but more metribuzin was present in the interior of the foliage of downy brome than of winter wheat. Results from petri dish studies in the field suggested that the amount of unaltered metribuzin available for absorption by leaves was influenced primarily by volatilization and secondarily by photodecomposition. In addition, small quantities of rainfall may have washed metribuzin from leaf surfaces. In 1984, yield of winter wheat was greater in metribuzin-treated plots than in nontreated check plots.

Increasing the air temperature from 20 to 32 C, the water temperature from 21 to 30 C, and the wind velocity from 0 to 8 km/h increased the loss of EPTC (S-ethyl dipropyl carbamothioate) from water applied through a sprinkler by 24 to 138%. Decreasing the water temperature from 21 to 10 C decreased the loss of EPTC by 35 to 50%. Decreasing the water pressure or nozzle size by 33% or doubling the herbicide concentration did not affect the percentage of EPTC lost.

Field studies were conducted in 1985 and 1986 to determine the influence of herbicide rate, carrier, and carrier volume on off-site movement of clomazone {2-[2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxalidinone} using sunflower (Helianthus annuus L. ‘HY-894’) and wheat (Triticum aestivum L. ‘Caldwell’) as indicator plants. Clomazone applied at the lowest rate (0.56 kg ai/ha) had less off-site movement than higher rates. Off-site movement was similar among water carrier volumes applied at each clomazone rate but was less when clomazone was impregnated onto dry fertilizer.

The behavior of the methyl ester of 14C-haloxyfop {2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl] oxy] phenoxy] propanoic acid} in common bermudagrass [Cynodon dactylon (L.) Pers. # CYNDA] stolons was examined in greenhouse experiments at two different seasons. The 14C from the herbicide applied on the leaves of a stolon node translocated no more than 3% of the applied radioactivity to the apex and base. Movement out of stolons was not significant. In early summer less than 1% translocated in each direction; in early fall more than 2% moved to the apex and less than 1% toward the base. Decrease of 14C recovery with time was evident in both seasons, particularly in early summer. Haloxyfop volatilization from the leaf surface apparently plays a significant role in recovery decrease. The 14C found in stolons in early summer was approximately the same as that of early fall, although herbicide remaining available for uptake on the leaf surface was lower in the former season. We suggest that environmental conditions that favor volatilization could enhance uptake.

Absorption and translocation of 14C-ethalfluralin (N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine) were measured in cucumber plants in the field and greenhouse. In field enclosures, cucumbers treated with 1.68 or 3.36 kg ai/ha preemergence soil-surface applications of 14C-ethalfluralin accumulated significantly more 14C in leaves than in petioles, stems, or fruits. In greenhouse studies, 14C-ethalfluralin vapor was absorbed by both cucumber seedling stems and cotyledons. Seedlings absorbed 14C-ethalfluralin from a nutrient solution and translocated 14C into all plant parts. Cucumber absorbed 14C-ethalfluralin topically applied to the stem and translocated 14C acropetally, while only limited basipetal translocation occurred. Although cotyledons absorbed 14C-ethalfluralin, very little 14 C moved out of the treated tissue.

The loss of metribuzin and ethyl-metribuzin from soil and glass surfaces was studied to determine if volatilization and/or photodegradation could explain inconsistent weed control with these herbicides. In growth chamber experiments, phytotoxicity of ethyl-metribuzin decreased as the time between surface application and initial watering increased. Approximately 50% of the applied metribuzin and ethyl-metribuzin volatilized from soil within 24 h, with an additional 15 to 20% lost during the next 11 days, except about 5% additional ethyl-metribuzin was lost from Chehalis sandy loam. Both herbicides volatilized more rapidly from glass than from soil, with 75 to 90% of the loss occurring within 24 h and as great as 99% loss after 12 days. Loss by photodecomposition from soil or glass surfaces was minimal.

As a result of applying arsenicals as herbicides, desiccants, or soil sterilants, soil As levels can increase under some conditions. Three arsenicals, sodium arsenite, (NaAsO2), cacodylic acid, (hydroxydimethylarsine oxide), and MSMA (monosodium methanearsonate) were applied to bare soil at 1, 2, and 10 times the recommended maximum application rates. After incorporation, radishes (Raphanus sativus L.) and soybeans [Glycine max (L.) Merr.] were planted as indicator crops to assess the phytotoxicity of accumulated soil As residues. Soil As residues increased at all levels of application. However, only 50% of the As applied at 10 times the recommended rate was found after seven annual applications, regardless of the source. Total losses of As from the soil averaged 14 to 15% of that applied each year. At 10 times the recommended rate, As generally reduced radish and soybean yields, but seldom reduced yields at the two lower rates. Results indicated little danger of As residue accumulating to phytotoxic levels under normal application rates.

The Persistence of substituted dinitroaniline herbicides in soil varied widely. First-order kinetics were used to describe the dissipation rates. Half-lives of the herbicides in moist soil ranged from 29 to 124 days in two soil types under greenhouse conditions. Flooding the soil significantly increased the dissipation rate of trifluralin (α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine), fluchloralin [N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)aniline], profluralin [N-(cyclopropylmethyl)-α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine], and pendimethalin [N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine]. Dissipation rates of dinitramine (N4,N4-diethyl-α,α,α-trifluoro-3,5-dinitrotoluene-2,4-diamine) and butralin [4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine] were affected to a lesser extent by flooding. Volatilization of trifluralin, fluchloralin, and ethalfluralin [N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine] from Bosket sandy loam was reduced by flooding when compared to volatilization from the same soil with a moisture content equivalent to field capacity. Pendimethalin exhibited low volatility. The effect of flooding on dissipation rates is apparently not due to increased volatilization.

Field studies conducted in 1991 to 1993 evaluated the efficacy of clomazone applied at various timings for weed control in soybean. Clomazone applied 45, 30, 15, or 0 days prior to planting (DPP) provided season-long control of velvetleaf and giant foxtail. In 1991 and 1992 clomazone alone 30 and 45 DPP failed to control redroot pigweed. Clomazone alone 45 DPP failed to control common lambsquarters. In 1991 and 1992 clomazone at 0.84 kg/ha plus metribuzin applied 45 DPP failed to control redroot pigweed. The addition of metribuzin plus chlorimuron to the above clomazone treatments resolved these weed control deficiencies. Weed control in 1993 was nearly complete across all clomazone treatments. In 1993 clomazone treatments which included metribuzin or metribuzin plus chlorimuron applied PPI or PRE reduced yield. Herbicide injury is the likely cause of this reduction because most treatments in 1993 provided 99% control of all weed species.

The volatilization, photolysis, microbial degradation, and field persistence of imazethapyr were studied using formulated and 14C-labeled imazethapyr. Volatilization losses from soil were less than 2%. Photodecomposition losses of up to 8% occurred from soil and up to 52% from a glass slide with no soil. Significantly greater photodecomposition occurred with chain-labeled than ring-labeled 14C-imazethapyr. The amount of 14CO2 evolution from soil treated with either ring- or chain-labeled 14C-imazethapyr was not significantly different. The total 14CO2 evolved from the soils ranged from 2.4 to 3.6% of the total 14C-imazethapyr applied to the soil. However, degradation of imazethapyr from the same soils, as determined by high-pressure liquid chromatography, indicated that 62 to 82% of the applied 14C-imazethapyr had been degraded. The degradation rate increased as soil moisture was increased from −100 to −33 kPa. Imazethapyr was more persistent in soil with the higher clay and organic matter content.

The behavior and dissipation of 26 dinitroaniline herbicides in soils are reviewed. Some of the compounds also are referred to as dinitrotoluidines, -benzen(e)amines, -benzenediamines, -cumidines, -benzenesulfonamides, -acetophenones, and sulfonylsulfilimines. All dinitroanilines are sorbed to soil particles, particularly to organic or humic substances, and are nearly immobile in soils. Soil K values range from 7 to 117 and KOC values range from 80 to 471 000. Compounds with vapor pressures greater than 50 × 10-6 mm of Hg at ambient temperatures were reported to volatilize and diffuse through, and out of, the soil in significant amounts, depending on temperature and moisture conditions. Greater losses occurred from warm, moist soils than from cool, dry soils. Photodecomposition of dinitroanilines on soil surfaces was low but occurred when the chemicals were present in the vapor state or in aqueous solutions. Bioavailability of the chemicals decreased as organic matter contents of the soils increased. Dinitroaniline herbicides were degraded primarily by soil microorganisms, and fungi were the major organisms involved. Degradation proceeded faster under anaerobic conditions than under aerobic conditions and faster under warm, moist conditions than under cool, dry conditions. Half-life values for dinitroanilines ranged from 7 to 27 days under anaerobic conditions and from 19 to 132 days under aerobic conditions. The chemicals did not affect most soil microflora; and any significant effects reported were of short duration.

Microbial degradation of imazaquin {2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid} was monitored by measuring 14CO2 evolution for 7 months under controlled laboratory conditions. Up to 10% of the 14C chain-labeled imazaquin that was applied to a Crowley silt loam was evolved as 14CO2 in 7 months. Less evolution of 14CO2 occurred on a Sharkey silty clay, a soil with higher clay and organic matter content, than on silt loam soils. The loss of 66 to 100% of the imazaquin applied to a Crowley silt loam incubated for 8 months at 18 C or 35 C, respectively, suggested that metabolic changes in addition to CO2 evolution were occurring. Rapid loss of imazaquin phytotoxicity occurred when soils were held at warm-moist (35 C and −33 kPa) conditions conducive to microbial growth. Imazaquin was more persistent in soils stored under cool, dry (18 C and −100 kPa) conditions. Imazaquin on a soil surface dissipated rapidly when exposed to ultraviolet light or sunlight. Photodecomposition could be a major mode of imazaquin dissipation if this herbicide is allowed to remain on the soil surface.

Low recoveries of total applied 14C in translocation studies and erratic control of hemp dogbane (Apocynum cannabinum L.) in the field showed a need for a balance-sheet study of absorption, translocation, and metabolism of 14C-2,4-D [(2,4-dichlorophenoxy) acetic acid] and 14C-glyphosate [N-(phosphonomethyl)glycine]. Total recovery of 14C-herbicides applied to hemp dogbane in the laboratory was 97% for 2,4-D and 105% for glyphosate. Of the 14C recovered after 12 days in the hemp dogbane, 34 to 55% was parent-2,4-D after 2,4-D treatment, and 93 to 96% was parent glyphosate after glyphosate treatment. Only negligible amounts of 14C were lost via volatilization or evolution as 14CO2. A broadcast treatment with unlabeled herbicide did not significantly affect subsequent absorption, translocation, or metabolism of either herbicide. Total herbicide absorbed and translocated out of the treated area of the leaf generally increased during the subsequent 12 days for 2,4-D but only 3 days for glyphosate. A greater percentage of the total applied 2,4-D (31 vs. 14%) and glyphosate (14 vs. 8%) was translocated from upper rather than lower leaves of hemp dogbane, respectively. Higher temperatures (30 vs. 25 C) resulted in greater translocation of glyphosate (39 vs. 18%) but not 2,4-D (35 vs. 39%). Higher light intensities resulted in greater accumulations of 2,4-D into roots and of glyphosate into untreated areas of the treated leaf. Autoradiographs showed that both herbicides moved through hemp dogbane in a typical symplastic pattern and accumulated in roots and new leaves.