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Miller, A. J., Bork, E. W., Hall, L. M. and Summers, B. 2015. Long-term forage dynamics in pastures sprayed with residual broadleaf herbicide: A test of legume recovery. Can. J. Plant Sci. 95: 43–53. Legumes such as alfalfa (Medicago sativa L.) and white clover (Trifolium repens L.) are important components of northern temperate pastures where they increase forage productivity and quality, but are susceptible to decline when exposed to broadleaf herbicides. Little is known about the long-term sward responses following herbicide use in northern temperate pastures, including the recovery of legumes and their subsequent contribution to forage production. We established five field sites over 2 yr to assess changes in grass, legume, total forage (grass+legume) and other forb biomass, as well as the recovery of a common weed, dandelion (Taraxacum officinale Weber), for up to 3 yr following a single application of two broad leaf herbicides with residual properties (aminopyralid and aminocyclopyrachlor). The importance of defoliation and the legume seed bank in facilitating legume biomass recovery were also evaluated with mowing and legume overseeding, respectively, in a strip/split-split design. Both herbicides had similar functional impacts on sward composition based on peak annual biomass, reducing legume biomass by an average of 71–100% across the 3 yr, equivalent to 63.4–22.6 g m−2 from year 1 to year 3, respectively. Although grass biomass did not change significantly with herbicides, net reductions in total forage were limited to 6.8% (28 g m−2) over the study, suggesting at least some ability of grasses to compensate for legume removal. Legume biomass was greater following overseeding and only in non-sprayed controls, but then decreased over time. Conversely, biomass of other forbs and cover of dandelion were lower shortly following herbicide application, only to reach levels similar to non-sprayed controls by the second growing season. Defoliation also influenced sward composition, favoring dandelion recovery following herbicide application. As both weed control and legume re-establishment are important objectives for livestock producers, the result of this study provides useful insight into the long-term impact of broad-leaf weed control on forage production in mixed swards of northern temperate pastures.

Previous research has shown that pyridine growth regulator herbicides can affect seed production in annual grasses including downy brome, Japanese brome, wheat, and other cereal grain crops. Aminocyclopyrachlor is a pyridine carboxylic acid growth regulator herbicide that has recently been registered for broadleaf weed and brush control in nonagricultural areas, which may help facilitate release of native perennial grasses in native plant restoration sites. The influence of aminocyclopyrachlor on downy brome seed production was evaluated at multiple application rates and timings under controlled field conditions. The effect of aminocyclopyrachlor on seed production was compared with aminopyralid, another pyridine growth regulator herbicide. When applied to downy brome plants in the early vegetative stage (EPOST) at approximately 580 growing degree days (GDD), aminocyclopyrachlor at 320 g ae ha 21 reduced seed germination by 50 to 88% in the first and second study years, respectively. Aminopyralid reduced seed germination by 94% in the first study year, but only 20% in the second year. When applied to downy brome plants in the early heading stage at approximately 1,235 GDD (LPOST), aminocyclopyrachlor at 320 g ae ha 21 reduced seed germination by 100% both years. Aminopyralid reduced seed germination by 95% in the first year, and 81% in the second year. Other than the observed reduction in seed germination, herbicides did not produce any visible changes in downy brome aboveground plant growth or development. Because downy brome seeds are relatively short-lived in soil, aminocyclopyrachlor and aminopyralid applications to downy brome–infested rangelands and other natural areas could result in reductions in downy brome population densities over time. No published data exist on the effect of aminocyclopyrachlor on seed production of desirable perennial grasses in natural ecosystems, thereby suggesting the need for further research. Nomenclature: Aminocyclopyrachlor, formerly DPX MAT28, 6-amino-5-chloro-2-cyclopropylpyrimidine-4carboxylic acid; aminopyralid, 4-amino-3,6-dichloropyridine-2-carboxylic acid; downy brome, Bromus tectorum L. BROTE; Japanese brome, Bromus japonicus Thunb. ex Murr. BROJA; wheat, Triticum aestivum L.

This study aimed to evaluate the sorption-desorption and leaching of aminocyclopyrachlor from three Brazilian soils. The sorption-desorption of 14C-aminocyclopyrachlor was evaluated using the batch...

The synthetic auxin herbicides, aminocyclopyrachlor and clopyralid, control dicotyledonous weeds in turf. Clippings of turfgrass treated with synthetic auxin herbicides have injured off-target plants exposed to herbicide-laden clippings. Labels of aminocyclopyrachlor and clopyralid recommend that clippings of treated turfgrass remain on the turf following a mowing event. Alternative uses for synthetic auxin-treated turfgrass clippings are needed because large quantities of clippings on the turf surface interfere with the functionality and aesthetics of golf courses, athletic fields, and residential turf. A white clover bioassay was conducted to determine the persistence and bioavailability of aminocyclopyrachlor and clopyralid in turfgrass clippings. Aminocyclopyrachlor and clopyralid were each applied at 79 g ae ha−1 to mature tall fescue at 56, 28, 14, 7, 3.5, and 1.75 d before clipping collection (DBCC). Clippings were collected, and the treated clippings were recycled onto adjacent white clover plots to determine herbicidal persistence and potential for additional weed control. Clippings of tall fescue treated with aminocyclopyrachlor produced a nonlinear regression pattern of response on white clover. Calculated values for 50% response (GR50) for visual control, for normalized difference vegetative index (NDVI), and for reduction in harvested biomass were 20.5, 17.3, and 18.7 DBCC, respectively, 8 wk after clippings were applied. Clippings of tall fescue treated with clopyralid did not demonstrate a significant pattern for white clover control, presumably because clopyralid was applied at a less-than-label rate. The persistence and bioavailability of synthetic auxin herbicides in clippings harvested from previously treated turfgrass creates the opportunity to recycle clippings for additional weed control.

Synthetic auxin herbicides have long been utilized for the selective control of broadleaf weeds in a variety of crop and noncrop environments. Recently, two agrochemical companies have begun to develop soybean with resistance to 2,4-D and dicamba which might lead to an increase in the application of these herbicides in soybean production areas in the near future. Additionally, little research has been published pertaining to the effects of a newly-discovered synthetic auxin herbicide, aminocyclopyrachlor, on soybean phytotoxicity. Two field trials were conducted in 2011 and 2012 to evaluate the effects of sublethal rates of 2,4-D amine, aminocyclopyrachlor, aminopyralid, clopyralid, dicamba, fluroxypyr, picloram, and triclopyr on visible estimates of soybean injury, height reduction, maturity, yield, and yield components. Each of these herbicides was applied to soybean at the V3 and R2 stages of growth at 0.028, 0.28, 2.8, and 28 g ae ha � 1 . Greater height reductions occurred with all herbicides, except 2,4-D amine and triclopyr when applied at the V3 compared to the R2 stage of growth. Greater soybean yield loss occurred with all herbicides except 2,4-D amine when applied at the R2 compared to the V3 stage of growth. The only herbicide applied that resulted in no yield loss at either stage was 2,4-D amine. When applied at 28 g ae ha � 1 at the V3 stage of growth, the general order of herbicide-induced yield reductions to soybean from greatest to least was aminopyralid . aminocyclopyrachlor ¼ clopyralid ¼ picloram . fluroxypyr . triclopyr . dicamba . 2,4-D amine. At the R2 stage of growth, the general order of herbicide-induced yiel dr eductions from greatest to least was aminopyralid . aminocyclopyrachlor ¼ picloram . clopyralid . dicamba . fluroxypyr ¼ triclopyr . 2,4-D amine. Yield reductions appeared to be more correlated with seeds per pod than to pods per plant and seed weight. An 18- to 26-d delay in soybean maturity also occurred with R2 applications of all synthetic auxin herbicides at 28 g ae ha � 1 except 2,4-D. Results from this research indicate that there are vast differences in the relative phytotoxicity of these synthetic auxin herbicides to soybean, and that the timing of the synthetic auxin herbicide exposure will have a significant impact on the severity of soybean height and/or yield reductions. Nomenclature: Aminocyclopyrachlor; aminopyralid; clopyralid; dicamba; fluroxypyr; picloram; triclopyr; 2,4-D; soybean, Glycine max (L.) Merr.

Aminocyclopyrachlor and indaziflam are under development in Brazil and there is no information about their behavior in Brazilian soils. This study aimed to evaluate the sensitivity of plant species to these new molecules, trying to select plants that can be used as bioindicators for testing the behavior of these herbicides in the soil. Two experiments were conducted, one for each herbicide. The treatments were arranged in a 8 x 6 factorial design, the factors being represented by eight species used as bioindicators cotton, maize, soybean, sorghum, sunflower, millet, cucumber and beet, and six doses of herbicides (aminocyclopyrachlor - 0, 10 , 20, 30 , 40 and 50 g ha-1 and indaziflam 0 , 20, 40 , 60, 80 and 100 g ha-1). Among the species studied, soybean and beet were quite sensitive to the two new herbicide molecules, being great alternatives for bioassays in order to detect low concentrations of aminocyclopyrachlor and indaziflam in the soil. O aminocyclopyrachlor e indaziflam encontram-se em fase de desenvolvimento no Brasil e não existem informações a respeito do comportamento destes em solos brasileiros. Este trabalho teve como objetivo avaliar a sensibilidade de espécies vegetais à estas novas moléculas, buscando selecionar plantas que possam ser utilizadas como bioindicadores em ensaios de comportamento destes herbicidas no solo. Foram conduzidos dois experimentos um para cada herbicida. Os tratamentos foram dispostos em esquema fatorial 8 x 6, sendo os fatores representados por oito espécies utilizadas como bioindicadoras algodão, milho, soja, sorgo, girassol, milheto, pepino e beterraba e seis doses dos herbicidas (aminocyclopyrachlor 0; 10; 20; 30; 40 e 50gha-1 e indaziflam 0; 20; 40; 60; 80 e 100gha-1 ). Dentre as espécies estudadas a soja e a beterraba mostraram-se bastante sensíveis as duas novas moléculas herbicidas, sendo ótimas alternativas para bioensaios visando a detecção biológica de baixas concentrações de aminocyclopyrachlor e indaziflam no solo.

Scotch broom is a large, nonnative shrub that has invaded forests and grasslands in 27 U.S. states. Without treatment, Scotch broom's persistent seedbank ensures a continuing source of regeneration after soil disturbance. In growth chamber studies, five rates of three synthetic auxin herbicides, aminocyclopyrachlor (AC), aminopyralid (AP), and clopyralid (CP), were compared for PRE control of Scotch broom. Cumulative 90-d emergence, mortality, and biomass of seedlings did not vary among herbicides, averaging 42% of seeds sown, 75% of emerged seedlings, and 9 mg seedling−1 for treated containers, respectively, versus 46%, 17%, and 26 mg seedling−1 for nontreated containers. Low rates of each herbicide (< 50% of the maximum labeled rate [MLR]) provided 60 to 80% control, whereas 100% MLR provided 69 to 89% control. Although the herbicides differed in cost per unit seedling mortality (AP < CP < AC), each demonstrated strong potential as a viable treatment for PRE control of Scotch broom.

Aminocyclopyrachlor has provided excellent control of many perennial weed species including leafy spurge, but control of yellow toadflax has been inconsistent.14C-aminocyclopyrachlor absorption was rapid in both leafy spurge and yellow toadflax and averaged 72% 48 h after treatment (HAT). However, translocation within the plant differed by species. More14C translocated to the aboveground portion of yellow toadflax (28% of applied) compared to leafy spurge (16.5% of applied). There was rapid translocation of14C-label to the roots of both species but more reached the belowground portion of leafy spurge than yellow toadflax. Over 12% of applied14C translocated into leafy spurge roots within 24 HAT but declined to 2% by 192 HAT. In comparison, only 2% of applied14C was found in yellow toadflax roots 24 HAT, and just 0.15% remained in belowground plant parts by 192 HAT. The inconsistent long-term control of yellow toadflax with aminocyclopyrachlor is likely due to poor translocation to the root system, which would allow for rapid regrowth in this hard to control perennial species.

Greenhouse experiments were conducted to evaluate mile-a-minute response to selected herbicides. In the first experiment, mile-a-minute response was evaluated following the application of aminocyclopyrachlor, aminopyralid, fluroxypyr, glufosinate, glyphosate, imazamox, imazapic, metsulfuron, penoxsulam, and triclopyr. Applications of aminocyclopyrachlor, aminopyralid, fluroxypyr, glufosinate, glyphosate, and triclopyr all resulted in mile-a-minute control 70% or greater 8 wk after treatment (WAT). Mile-a-minute sensitivity to these six herbicides was further evaluated in a dose-response study. Although 90% growth reduction (GR90) values were determined for aminopyralid and glyphosate, statistically significant results were not obtained for aminocyclopyrachlor, fluroxypyr, glufosinate, and triclopyr. The results of these experiments suggest that glyphosate, as well as the synthetic auxin herbicides aminocyclopyrachlor, aminopyralid, fluroxypyr, and triclopyr, should be further evaluated for mile-a-minute control in south Florida.

Aminocyclopyrachlor is a pyrimidine carboxylic acid herbicide used to control broadleaf weeds and brush. Amending soil with activated charcoal is recommended to prevent off-site transport of aminocyclopyrachlor and non-target plant damage. We used the batch-equilibrium method to determine the concentration of aminocyclopyrachlor in a pseudo-steady state with biochar, soil, and biochar-soil systems (10% biochar by weight). We observed that aminocyclopyrachlor is mobile in soils. Soil incorporation of activated charcoal removed nearly all of the aqueous aminocyclopyrachlor thereby limiting its bioavailability to non-target flora. On the other hand, biochars were less effective than activated charcoal. Biochar produced from olive mill waste feedstock was the most effective biochar that we assessed for reducing the aqueous herbicide concentration. Although these biochars reduced the aminocyclopyrachlor concentration, they would not be practical remediation media due to the extraordinarily high application rates required to reduce the concentration by 50% (2.13 × 10(5) kg ha(-1)-7.27 × 10(5) kg ha(-1)).

Synthetic auxin herbicides are widely utilized in golf course settings for selective broadleaf weed control. Aminocyclopyrachlor (AMCP) is a newly registered pyrimidine carboxylic acid with similar chemical mode-of-action and structure to triclopyr (TRIC) and clopyralid (CLPY). Off-target injury on terrestrial plants has been documented following exposure to turfgrass clippings previously treated with TRIC and CLPY. Management practices on golf courses can distribute turfgrass clippings into water bodies; however, research has not evaluated the bioavailability of synthetic auxin residues from turfgrass clippings to aquatic and riparian plants within these environments. A bioassay study was conducted to determine the response of alligatorweed and parrotfeather to tall fescue clippings previously treated with synthetic auxin herbicides. Previously treated AMCP and TRIC + CLPY clippings were placed into growth containers mimicking a lentic system containing both alligatorweed and parrotfeather. Results indicated all herbicide treated clippings induced significant growth responses to alligatorweed and parrotfeather growth compared to a nontreated mulch and nontreated control. Alligatorweed control was greater from AMCP clippings treated 14, 7, 3, and 1 DBCC (49, 60, 90, and 80%, respectively) than comparative TRIC + CLPY clippings (33, 25, 37, and 64%, respectively) at 10 weeks after treatment (WAT). Parrotfeather control was greater from AMCP clippings (57 to 87%) than TRIC + CLPY clippings (9 to 63%) collected from all days before clipping collection (DBCC) timings when evaluated 6 WAT. At 10 WAT, greater parrotfeather control and shoot reduction was observed from AMCP than TRIC + CLPY clippings when treated 14, 7, and 3 DBCC. Based on these data, synthetic auxin residues can become bioavailable to aquatic and riparian plants within aqueous environments.

The quick, easy, cheap, effective, rugged, and safe (QuEChERS) and the U. S. Food and Drug Administration pesticide multiresidue methods were systematically tested for the analysis of aminocyclopyrachlor, a new synthetic auxin herbicide. Results revealed that these procedures are not suitable, highlighting the need for a publicly available residue method for this new active ingredient. Such a method has been developed and is reported herein for aminocyclopyrachlor residue analysis in vegetation, including white pine, Norway spruce, grass forage, and grass hay. Aminocyclopyrachlor residues were purified from plant tissue extracts by filtration through SPE cartridges with strong anion exchange stationary phases and analyzed using LC/MS/MS. This method was validated at five laboratories across the United States; their results were compared to evaluate reproducibility and ruggedness. The method LOQ was 0.01 mg/kg (ppm) and the LOD 0.003 mg/kg (ppm) for the matrixes tested. A qualitative procedure to confirm the molecular identity of residues based on retention time measurements and ion transition peak area ratios (m/z 214 → 68/m/z 214 → 101) is also presented.

Virginia buttonweed and smooth crabgrass are problematic weeds in tall fescue and may warrant control with herbicides at similar timings. The objectives of these field experiments were to evaluate (1) aminocyclopyrachlor rate and application regimens for controlling Virginia buttonweed and (2) the influence of growth stage on aminocyclopyrachlor efficacy for controlling smooth crabgrass. Single applications of aminocyclopyrachlor at 0.05 and 0.08 kg ai ha−1 provided poor (< 70%) and fair (70 to 79%) control of Virginia buttonweed, respectively, but sequential applications improved control to 83 to 99%. Single and sequential applications of aminocyclopyrachlor at 0.11 kg ai ha−1 provided good (80 to 89%) and excellent (> 90%) control of Virginia buttonweed, respectively. Aminocyclopyrachlor at 0.11 kg ha−1 provided fair control of smooth crabgrass at the multileaf growth stage prior to tillering but control was poor when applied at the multitiller stage. Aminocyclopyrachlor at 0.05 and 0.08 kg ha−1 provided poor control of crabgrass at both timings and were less effective than fenoxaprop at 0.10 kg ai ha−1.

Synthetic auxin herbicides are commonly used in forage, pasture, range, and turfgrass settings for dicotyledonous weed control. Aminocyclopyrachlor (AMCP) is a newly developed pyrimidine carboxylic acid with a chemical structure and mode of action similar to the pyridine carboxylic acids—aminopyralid, clopyralid, and picloram. Injury to sensitive dicotyledonous plants has been observed following exposure to monocotyledonous plant material previously treated with pyridine compounds. The absorption, translocation, and metabolism of AMCP has been documented in susceptible broadleaf weeds; however, no information is available, to our knowledge, regarding AMCP fate in tolerant Poaceae, which may serve as the vector for off-target plant injury. Based on this premise, research was conducted to characterize absorption, translocation, and metabolism of AMCP in tall fescue.14C-AMCP was applied to single tiller tall fescue plant foliage under controlled laboratory conditions at North Carolina State University (Raleigh, NC). Radiation was quantified in leaf wash, treated leaf, foliage, crown, roots, and root exudates at 3, 12, 24, 48, 96, and 192 h after treatment (HAT).14C-AMCP was rapidly absorbed by tall fescue, reaching 38 and 68% at 3 and 48 HAT, respectively. Translocation of14C-AMCP was limited to the foliage, which reached maximum translocation (34%) at 96 HAT. Most of the recovered14C-AMCP remained in the leaf wash, treated leaf, or foliage, whereas minimal radiation was detected in the crown, roots, or root exudates throughout the 192-h period. No AMCP metabolism was observed in tall fescue through the 192 HAT. These data suggest AMCP applied to tall fescue can remain bioavailable, and mishandling treated plant material could result in off-target injury.

Dalmatian toadflax is listed as a noxious weed in most of the western United States, but control of this species has not been extensively studied in California. Studies in other states show effective control of Dalmatian toadflax with picloram, but this herbicide is not registered for use in California. In addition, reports vary as to the optimal timing for herbicide applications. In this study we evaluated several herbicides with combined foliar and soil-residual activity at two times of application: postsenescence (fall) and rosette (winter to early spring). We applied two series of treatments (2008 and 2009 to 2010) on adjacent sites in high desert scrub of southern California. In the year of treatment and the following year, we evaluated Dalmatian toadflax cover and presence/absence of associated dominant species (≥ 5% cover). Although time of application, treatment, and timing by treatment interaction all produced significant differences in Dalmatian toadflax cover in the 2008 trial, only the high rate of aminocyclopyrachlor (280 g ae ha−1) applied to dormant plants in fall consistently reduced cover through the second year. No treatments at the rosette stage consistently produced 2 yr of control. In 2009 to 2010, treatments were more effective, probably owing to higher precipitation in spring. In both dormant and rosette applications made in 2009 to 2010, aminocyclopyrachlor (140 and 280 g ae ha−1) and aminocyclopyrachlor + chlorsulfuron (140 g ae ha−1+ 53 g ai ha−1) gave second year control; chlorsulfuron at the dormant stage (105 and 158 g ai ha−1) and aminopyralid at the rosette stage (245 g ae ha−1) also gave 2 yr of control. The treatments had only minor effects on grass species. The response of broadleaf species varied among treatments, with aminocyclopyrachlor at the high rate increasingEriogonumspp., but greatly reducing Asteraceae species. These results provide options for the management of Dalmatian toadflax in California and other western states.

Aminocyclopyrachlor is an herbicide for broadleaf weed control that has recently come under scrutiny following reports of injury to landscape ornamentals across the upper Midwestern United States. This herbicide has been shown to provide excellent weed control in warm-season turfgrasses at much lower use rates than that used for cool-season turf, but data are lacking concerning its safety to landscape ornamentals in southern U.S. regions. Parallel studies were conducted in Dallas and Huntsville, TX, locations to evaluate off-target injury effects on sixteen ornamentals and trees commonly used in southern landscapes. In March 2012, just prior to the spring growth flush, aminocyclopyrachlor was applied to potted plants at 0, 0.5, 1, 2, or 4× rates as either as granular [0, 14, 28, 56, or 112 g ai·ha−1 (0.013, 0.03, 0.05, and 0.10 lbs ai·A−1)] or liquid [0, 11.2, 22.4, 44.8, or 89.6 g ai·ha−1 (0.01, 0.02, 0.04, 0.08 lbs ai·A−1)] formulations. For the next 8 weeks, plants were evaluated for injury to new growth. Injury was observed in 9 of the 16 species used, but was generally mild to moderate in nature. Species exhibiting the greatest sensitivity to aminocyclopyrachlor included loblolly pine (Pinus taeda), viburnum (Viburnum odoratissimum), nandina (Nandina domestica ‘Compacta’), and camellia (Camellia japonica). Extent of injury was not different between granular or liquid formulations, but was less severe at the Dallas location. Results of the study indicate sensitivity within some southern landscape ornamentals to aminocyclopyrachlor.

Aminocyclopyrachlor will control a variety of invasive weeds but may injure sensitive plant species if seeded into treated soil too soon after application. Aminocyclopyrachlor 50% dissipation time (DT50) ranged from 3 to > 112 d in four soils from the Northern Great Plains. The DT50was dependent on several factors including soil type, moisture content, and temperature. Across four different soil textures, aminocyclopyrachlor dissipation generally increased as soil moisture content increased, but moisture had less of an impact in sandy soils. Aminocyclopyrachlor dissipation also increased as temperature increased in the four soils. The most rapid dissipation occurred in soils with higher clay content, which also had the highest organic matter content of the soils evaluated, and an average DT50of less than 20 d. Seeding sensitive pasture, range, or crop species after aminocyclopyrachlor applications should be done with caution since the herbicide has potential for long persistence in the soil.

Aminocyclopyrachlor (AMCP) is a newly developed synthetic auxin herbicide for broadleaf weed control in turfgrass systems. AMCP has been observed to undergo rapid photodecomposition in shallow water when exposed to sunlight. Most herbicide applications on golf courses occur during the morning when dew is still present on the turfgrass canopy. These conditions could result in efficacy loss if photolysis occurred while AMCP is suspended in dew droplets. Research was conducted to determine the effect of ambient moisture on AMCP efficacy. AMCP (79 and 105 g ae ha−1), aminopyralid (280 g ae ha−1), and two AMCP granular formulations (84 g ha−1) were applied to dew-covered (WET) and dew-excluded (DRY) ‘Tifway' bermudagrass plots. Herbicide treatments applied to WET plots had greater visually rated bermudagrass injury than respective treatments applied to DRY plots at 7 and 21 d after treatment (DAT), with the exception of aminopyralid at 21 DAT. Normalized difference vegetative index on turfgrass quality complemented visual ratings, indicating greater turfgrass quality reductions when applied to WET vs. DRY plots. These results indicate that AMCP applications made to dew-covered turfgrass can increase herbicidal efficacy, and no significant losses due to photodegradation were observed.

Vapor movement of synthetic auxin herbicides can injure desirable plants outside the treatment zone. Vapor movement of the synthetic auxin herbicides aminocyclopyrachlor and aminocyclopyrachlor methyl was compared with that of the relatively volatile herbicide dicamba and the low volatile herbicide aminopyralid with a soybean bioassay under greenhouse and field conditions. Soybean is very sensitive to these active ingredients. Under greenhouse conditions, 82 (61 to 104) mg ae ha−1of aminocyclopyrachlor, 26 (18 to 33) mg ae ha−1of aminocyclopyrachlor methyl, 82 (69 to 95) mg ae ha−1of aminopyralid, and 61 (47 to 75) mg ae ha−1of dicamba produced an estimated 25% visual soybean phytotoxicity response when soybean was treated POST at the V3 growth stage (GR25[95% confidence interval]). In field studies, aminocyclopyrachlor, aminocyclopyrachlor methyl, and aminopyralid were applied at 70 g ae ha−1and dicamba was applied at 560 g ae ha−1(labeled application rates) to soybean at the V3 growth stage. All herbicides were applied within an enclosed chamber (3 m by 3 m by 1 m) to mitigate movement of spray droplets. The enclosures were removed shortly after spray application and soybean response immediately surrounding the treated area was recorded in each of eight directions approximately 10 d after treatment. On the basis of bioassay responses, relative amount of vapor movement was dicamba > aminocyclopyrachlor methyl > aminopyralid ≈ aminocyclopyrachlor. Vapor movement of aminocyclopyrachlor was very low indicating that the risk of phytotoxic response of sensitive plants due to volatility of aminocyclopyrachlor is negligible.

Field bindweed is extremely susceptible to aminocyclopyrachlor compared to other weed species. Laboratory studies were conducted to determine if absorption, translocation, and metabolism of aminocyclopyrachlor in field bindweed differs from other, less susceptible species. Field bindweed plants were treated with 3.3 kBq14C-aminocyclopyrachlor by spotting a single leaf mid-way up the stem with 10 µl of herbicide solution. Plants were then harvested at set intervals over 192 h after treatment (HAT). Aminocyclopyrachlor absorption reached a maximum of 48.3% of the applied radioactivity by 48 HAT. A translocation pattern of herbicide movement from the treated leaf into other plant tissues emerged, revealing a nearly equal aminocyclopyrachlor distribution between the treated leaf, aboveground tissue, and belowground tissue of 13, 14, and 14% of the applied radioactivity by 192 HAT. Over the time-course, no soluble aminocyclopyrachlor metabolites were observed, but there was an increase in radioactivity recovered bound in the nonsoluble fraction. These results suggest that aminocyclopyrachlor has greater translocation to belowground plant tissue in field bindweed compared with results from other studies with other herbicides and other weed species, which could explain the increased level of control observed in the field. The lack of soluble metabolites also suggests that very little metabolism occurred over the 192 h time course.

Aminocyclopyrachlor (AMCP) is a herbicide with an auxin-mimic mode of action. AMCP is registered for use in the United States on right-of-way and other noncropland sites, causing concern for potential off-target spray drift. The objectives of this study were to evaluate cantaloupe and eggplant response to simulated AMCP spray drift in the field and cotton response in the greenhouse. Cantaloupe and eggplant responded with little to no injury from drift rates up to 10 g AMCP ha−1, roughly 3.2% of the maximum labeled use rate for right-of-way weed control. Slight yield reductions occurred but were not consistent between 2008 and 2009. Therefore, eggplant and cantaloupe injury and yield-reduction potential from AMCP spray drift is low. Cotton response to AMCP drift was compared to similar spray drift rates of 2,4-D and aminopyralid. Cotton responded with injury and reductions in height and dry mass from all three herbicides. Responses were greatest from AMCP, indicating AMCP is potentially more damaging to cotton than 2,4-D or aminopyralid if spray drift occurs, when comparing percentages of labeled rates.

Herbicides aminocyclopyrachlor and indaziflam are under development in Brazil. Information about the behaviors in Brazilian soils and climate is scarce. Thus, the present work has aimed to evaluate the persistence of biological activity and leaching potential of aminocyclopyrachlor and indaziflam in contrasting textured soils by means of bioassays. For the evaluation of persistence, four experiments were performed, in which soils with different textures were studied in different time periods between herbicide application and bioindicator sowing (beet and soybeans). To determine leaching potential, three blades of rainfall (0, 30 and 60 mm) were simulated, each constituting a single experiment in soils with different textures and five bands of depth in the columns. The bioindicator used for the leaching tests was beet. The persistence of biological activity of aminocyclopyrachlor and indaziflam was greater than 150 days. In clayey soil there was less persistent aminocyclopyrachlor than in the loam texture. For indaziflam there was no difference in persistence between the two soils. Regarding the leaching potential, it was observed that the precipitations have the capacity to interfere with the leaching of herbicides aminocyclopyrachlor and indaziflam. Aminocyclopyrachlor has greater potential for leaching than indaziflam. The first one has its mobility increased when applied to soil of loam texture in relation to very clayey soil. As for indaziflam, marked differences between soils with different textures have not been noticed. RESUMO Os herbicidas aminocyclopyrachlor e indaziflam encontram-se em fase de desenvolvimento no Brasil. Informações a respeito do comportamento deles em condições edafoclimáticas brasileiras são escassas. O presente trabalho foi desenvolvido com o objetivo de avaliar a persistência da atividade biológica e o potencial de lixiviação do aminocyclopyrachlor e indaziflam em solos de texturas contrastantes, por meio de bioensaios. Para avaliação da persistência foram realizados quatro experimentos, em que foram estudados solos com texturas distintas em diferentes períodos de tempo entre a aplicação dos herbicidas e a semeadura do bioindicador (beterraba e soja). Para determinação do potencial de lixiviação, simularam-se três lâminas de precipitação (0, 30 e 60 mm), cada uma constituindo um experimento isolado, em solos com diferentes texturas e cinco faixas de profundidades nas colunas. O bioindicador utilizado para os ensaios de lixiviação foi a beterraba. A persistência da atividade biológica do aminocyclopyrachlor e indaziflam foi superior a 150 dias. No solo de textura muito argilosa, verificou-se menor persistência do aminocyclopyrachlor do que no de textura franco-argiloarenosa. Para o indaziflam, não se observou diferença na persistência entre os dois solos estudados. Com relação ao potencial de lixiviação, observou-se que as precipitações possuem capacidade de interferir na lixiviação dos herbicidas aminocyclopyrachlor e indaziflam. O aminocyclopyrachlor possui maior potencial de lixiviação do que o indaziflam; o primeiro tem sua mobilidade aumentada quando aplicado em solo de textura franco-argiloarenosa, em relação ao solo de textura muito argilosa. Quanto ao indaziflam, não foram notadas diferenças marcantes entre os solos com diferentes texturas.

The species Tecoma stans, introduced to Brazil to be cultivated in urban centers as street trees, in parks and gardens, became important pasture weed. The mechanical control of this species is difficult because the plant presents a large number of sprouts when are mowed. Furthermore, the herbicides usually used in pasture have been shown to be inefficient to control it. This research evaluated the trumpet flower control effectiveness using a new herbicide (aminocyclopyrachlor) applied alone in increasing doses to the cut stump for the control of resprouts and mixed with metsulfuron-methyl in applications to intact plant leaves. The experiment with foliar applications used increasing doses of herbicides (aminocyclopyrachlor + metsulfuron-methyl). Applications of only aminocyclopyrachlor to the cut stump and foliar application of a herbicidal mixture (aminocyclopyrachlor + metsulfuron-methyl) were effective in the control of trumpet flower. RESUMO A espécie Tecoma stans introduzida no Brasil para ser cultivada nos centros urbanos em arborização de ruas, praças e jardins tornou-se importante planta daninha em pastagens. O controle mecânico dessa espécie é difícil, por apresentar grande número de rebrotas quando as plantas são roçadas. Além disso, os herbicidas normalmente usados em pastagens têm-se mostrado ineficientes no seu controle. Nesta pesquisa foi avaliada a eficiência de controle do amarelinho por um novo herbicida, o aminocyclopyrachlor, aplicado em doses crescentes de forma isolada no toco, visando o controle das rebrotas, e em mistura com o metsulfuron-methyl, em aplicações nas folhas de plantas intactas. No experimento com aplicações foliares foram utilizadas doses crescentes de (aminocyclopyrachlor + metsulfuron-methyl). Aplicações no toco de aminocyclopyrachlor de forma isolada e foliares da mistura de (aminocyclopyrachlor + metsulfuron-methyl) foram eficazes no controle de amarelinho.

Trumpetcreeper (Campsis radicans) is a native, perennial, weedy vine of pastures, row crops, fence rows, and right-of-ways throughout most of the eastern United States. Field and greenhouse studies were conducted in 2008 and 2009 near Newport, TN, and in Knoxville, TN, to evaluate aminocyclopyrachlor-methyl and aminopyralid alone and in mixtures with 2,4-D and diflufenzopyr for selective trumpetcreeper control when applied postemergence in an abandoned nursery. These treatments were compared with commercial standards of dicamba and a prepackaged mixture of triclopyr plus 2,4-D. In the field, aminocyclopyrachlor-methyl alone controlled trumpetcreeper 77% to 93%, while aminopyralid alone only controlled trumpetcreeper 0% to 20% by 12 months after treatment (MAT). The addition of diflufenzopyr or 2,4-D to aminocyclopyrachlor-methyl did not improve trumpetcreeper control in the field; however, the addition of 2,4-D to aminopyralid improved control of trumpetcreeper from 50% to 58%. All aminocyclopyrachlor-methyl treatments controlled trumpetcreeper greater than or equal to dicamba and the prepackaged mixture of triclopyr plus 2,4-D. In the greenhouse, aminocyclopyrachlor and aminocyclopyrachlor-methyl applied at 8.75 to 35 g·ha−1 controlled trumpetcreeper 58% to 72% by 1 MAT. When both herbicides were applied at 70 g·ha−1, aminocyclopyrachlor controlled trumpetcreeper 64%, while aminocyclopyrachlor-methyl controlled trumpetcreeper 99%, similar to dicamba.

Research was conducted to determine the efficacy of aminocyclopyrachlor in comparison to glyphosate, clopyralid, fluroxypyr, and triclopyr for silk tree (commonly known as mimosa) control. In the greenhouse, aminocyclopyrachlor was applied at 8.75, 17.5, 35, and 70 g ha−1with and without methylated seed oil (MSO) at 0.5% v/v. Efficacy of these treatments was compared to glyphosate and triclopyr at 1,350 g ha−1, fluroxypyr at 103 g ha−1, and clopyralid at 100 g ha−1. Few differences in silk tree control were detected by 28 d after treatment (DAT), as aminocyclopyrachlor with MSO controlled silk tree 87 to 100% compared to 53 to 100% for aminocyclopyrachlor without MSO. Aminocyclopyrachlor at 35 g ha−1provided silk tree control similar to glyphosate, triclopyr, clopyralid, and fluroxypyr regardless of adjuvant. Inclusion of MSO enhanced initial activity of aminocyclopyrachlor after application. At 7 DAT, 8.75 g ha−1of aminocyclopyrachlor plus MSO controlled silk tree similar to aminocyclopyrachlor alone at 70 g ha−1. In laboratory studies, absorption of14C-aminocyclopyrachlor 2 h after treatment (HAT) with MSO measured 93% compared to only 62% for14C-aminocyclopyrachlor without MSO. By 24 HAT, absorption of14C-aminocyclopyrachlor measured 99 and 71% for applications with and without MSO, respectively. Increased foliar absorption with MSO may explain enhanced activity observed 7 DAT in greenhouse studies, as no effects in14C-aminocyclopyrachlor translocation due to adjuvant were observed. Responses suggest MSO increased the speed of silk tree control with aminocyclopyrachlor and may also improve rainfastness of aminocyclopyrachlor applications for control of silk tree and other woody species.

Largeleaf lantana is a perennial shrub that commonly infests pastures, roadsides, and natural areas. Many experiments have been conducted to manage this weed, but few successful herbicides have been found. Little information is available for the effectiveness of fluroxypyr, aminopyralid, or aminocyclopyrachlor on largeleaf lantana. Experiments were conducted in central Florida on dense, natural infestations of largeleaf lantana. Aminopyralid (0.12 kg ha−1), fluroxypyr (0.56 kg ha−1), and aminocyclopyrachlor (0.2 kg ha−1) were either applied in the fall (approximately 2 mo before frost) or in the fall followed by a spring application. Aminopyralid was ineffective on largeleaf lantana, and neither one nor two applications resulted in > 20% control 1 yr after treatment (YAT). Fluroxypyr applied once in the fall resulted in 12% control at 1 YAT, but two applications resulted in 80% control after 1 yr. The combination of fluroxypyr + aminopyralid, applied twice, resulted in approximately 90% control 1 YAT. A single application of fluroxypyr + aminopyralid failed to provide greater than 20% control. Conversely, aminocyclopyrachlor applied once in the fall provided 98% control of largeleaf at 1 YAT. Where aminocyclopyrachlor was applied twice, largeleaf lantana control was 100%. From these data, largeleaf lantana can be effectively controlled by two applications of fluroxypyr, two applications of fluroxypyr + aminopyralid, or a single application of aminocyclopyrachlor. Individual plant treatments were also investigated using herbicides applied as basal or cut surface applications. At 1 YAT, only triclopyr + aminopyralid provided > 90% control as a basal application. The other herbicide combinations appeared to be effective earlier, but significant regrowth had occurred by 1 YAT. Cut surface applications were similar with triclopyr + aminopyralid and triclopyr + fluroxypyr providing effective control. Neither triclopyr alone nor imazapyr provided effective control for 1 YAT with basal or cut surface applications.

Herbicides used to control many forb species in pastures may injure desirable native grass species. Buffalograss, a major component of shortgrass rangeland, often is injured by some growth regulator herbicides, such as 2,4-D and dicamba. Aminocyclopyrachlor (formerly known as DPX-MAT28 and herein termed ACPCR), a new synthetic auxin herbicide chemistry for control of broadleaf weeds, was investigated for injury to buffalograss and control of forbs in shortgrass prairie at varying rates of application. In the season of application, ACPCR at rates of 140 g ai ha−1or less caused buffalograss injury that was either negligible or short-lived, and visual estimates of grass injury were 8% or less at the end of the growing season. At ACPCR rates of 280 g ha−1, more injury was evident at 3 wk after treatment (WAT) than at the end of the season if adequate precipitation was available for new leaf growth. When precipitation was lacking, evidence of injury persisted through to the end of the season when treated at the greatest rate of ACPCR. Buffalograss injury was mainly in the form of browned leaf tips, but total buffalograss dry matter yield was not different between any treatments in either year. The year after treatment, no buffalograss injury was evident from any of the herbicide rates. Final forb control was 97% or greater each year for ACPCR at the 140 and 280 g ha−1rates. In this experiment, rates as low as ACPCR at 140 g ha−1provided excellent forb control and maintained buffalograss productivity.

Flue-cured tobacco is sensitive to foliar and soil residues of off-target synthetic auxin drift. Aminocyclopyrachlor is a newly developed synthetic auxin herbicide that may be used in right-of-way applications for broadleaf weed and brush control. Aminocyclopyrachlor is considered a reduced-risk alternative in rights-of-way compared with similar compounds because of its low application rate and volatility risk. However, no research is available on the response of field-grown, flue-cured tobacco to aminocyclopyrachlor drift exposure. Research was conducted in 2009 and 2010 at the Border Belt Tobacco Research Station in Whiteville, NC, to determine the response of ‘NC 71’ flue-cured tobacco to five simulated drift rates of aminocyclopyrachlor (0.31, 1.6, 3.1, 15.7, and 31.4 g ae ha−1) and one aminopyralid (6.1 g ae ha−1) simulated drift rates applied pretransplant incorporated, pretransplant unincorporated, 3 wk after transplant, and 6 wk after transplant. All herbicide rates and application timings caused significant visual tobacco injury, ranging from slight to severe with increasing herbicide drift rates. Tobacco plant heights and fresh weights were reduced at all application timings receiving ≥ 15.7 g ha−1aminocyclopyrachlor and the comparative aminopyralid rate.

Kudzu is an invasive perennial climbing vine characterized by fast growth rates and tolerance to control measures. Repeated applications with high rates of 2,4-D plus picloram provide effective kudzu control, but picloram use is not permitted in certain states due to groundwater pollution concerns. Studies were conducted in Alabama and Florida to compare kudzu control with aminocyclopyrachlor, a new herbicide, to control provided by aminopyralid, clopyralid, metsulfuron methyl, and picloram plus 2,4-D, which are common treatments for kudzu management. Two annual applications of the same herbicide treatment were evaluated for effects on kudzu cover, kudzu volume index, and cover of other vegetation. Aminocyclopyrachlor at 140 to 280 g ae ha−1 (2 to 4 oz ae ac−1) was as effective as the standard 4.48 kg ae ha−1 (4 lb ae ac−1) 2,4-D amine plus 1.2 kg ae ha−1 picloram for kudzu control. There were no differences in kudzu control among the three rates of aminocyclopyrachlor tested. Colonization by graminoids, forbs, and Rubus spp. at 2 yr was greatest for herbicides providing the best kudzu control: aminocyclopyrachlor, and 2,4-D plus picloram. Herbicide treatments were more effective in controlling kudzu at the Alabama location, but repeated annual applications for 2 yr did not completely eliminate kudzu with any treatment at either site.

Synthetic auxin herbicides are widely used because of their effective control of broadleaf weeds and safety in many turfgrass species. However, two synthetic auxin herbicides, triclopyr and aminocyclopyrachlor (AMCP; DPX-KJM44), are known to injure warm-season turfgrasses. Our objective was to quantify this injury through evaluations of turfgrass quality and turfgrass green cover in response to herbicide treatment. The results of this study indicate that relative to the labeled use rates of triclopyr (0.56 to 1.12 kg ae ha−1) and AMCP (0.053 kg ai ha−1), zoysiagrass is the only turfgrass tested with sufficient tolerance to the respective compounds for their use as weed-control agents. Bermudagrass and centipedegrass may be injured by triclopyr and AMCP at labeled rates, characterized by a reduction in turfgrass quality and green cover. St. Augustinegrass is not tolerant of either triclopyr or AMCP at labeled rates. Nomenclature: Aminocyclopyrachlor-methyl, DPX-KJM44; triclopyr; centipedegrass, Er...

Fenoxaprop effectively controls crabgrass in tall fescue turf, but antagonism with growth-regulating herbicides reduces potential to apply fenoxaprop in combination with many herbicides registered for broadleaf weed control. Aminocyclopyrachlor is a new broadleaf weed control herbicide that has not been evaluated in combination with fenoxaprop. Field experiments were conducted in Georgia, New Jersey, and Tennessee to investigate tank mixtures of fenoxaprop with aminocyclopyrachlor for smooth crabgrass and white clover control. Fenoxaprop alone exhibited substantial activity on smooth crabgrass but control was greater with fenoxaprop + aminocyclopyrachlor treatments. By 4 and 6 wk after treatment (WAT), approximately 22 and 44% less fenoxaprop was required to achieve 80% smooth crabgrass control when the herbicide was tank-mixed with aminocyclopyrachlor at 52.5 and 79 g ai ha−1, respectively. Fenoxaprop did not reduce white clover control with aminocyclopyrachlor because 97% control was achieved by 4 WAT for all aminocyclopyrachlor + fenoxaprop treatments. Tall fescue was not injured by any treatment. Results suggest aminocyclopyrachlor enhances fenoxaprop efficacy for smooth crabgrass control in tall fescue.

Researchers, product registration personnel, and growers desire the ability to chemically detect residual amounts of herbicides in soil at concentrations below those necessary to cause phytotoxicity to sensitive nontarget or rotational crop plants. Alfalfa, cotton, soybean, and sunflower, crops sensitive to low concentrations of aminocyclopyrachlor in soil, were planted at field test sites approximately 1 yr after aminocyclopyrachlor methyl was applied. Soil samples were collected when rotational crops were planted and were analyzed for aminocyclopyrachlor by a method based on high performance liquid chromatography tandem mass spectrometry (HPLC/MS/MS), with a limit of detection (LOD) of 0.1 part per billion (ppb) (soil oven-dry weight basis). Loglogistic dose–response analysis correlated visual phytotoxic plant responses to residual concentrations of aminocyclopyrachlor in the soil. Concentrations of aminocyclopyrachlor estimated to cause 25% phytotoxicity to alfalfa, cotton, soybean, and sunflower were 5.4, 3.2, 2.0, and 6.2 ppb, respectively, 20 to 60 times greater than the LOD of the analytical method available for soil analysis. Results from these studies suggest this HPLC/MS/MS method of analysis can be used to indicate potential risk and severity of plant response for alfalfa, cotton, soybean, and sunflower, and for other plant species once dose–response curves for these additional species are established. This chemical assay may be particularly important if researchers desire to study the concentration, movement, and dissipation of aminocyclopyrachlor in soil or as part of a forensic investigation to better understand the cause of an unanticipated or undesirable plant response.

BACKGROUND: Aminocyclopyrachlor is a new herbicide proposed to control broadleaf weeds and shrubs in non-crop and rangeland systems. To gain a better understanding of observed field efficacy, the uptake and translocation of foliar-applied aminocyclopyrachlor (DPX-MAT28) and aminocyclopyrachlor methyl ester (DPX-KJM44) were evaluated in two annuals, prickly lettuce (Lactuca serriola L.) and yellow starthistle (Centaurea solstitialis L.), and one perennial, rush skeletonweed (Chondrilla juncea L.). RESULTS: Absorption and translocation varied between species. While absorption of DPX-KJM44 was greater than absorption of DPX-MAT28, rush skeletonweed absorbed the most, followed by yellow starthistle and prickly lettuce. Overall, the total translocation of either herbicide was highest in yellow starthistle, followed by rush skeletonweed and prickly lettuce. Proportional herbicide movement between species was similar, with the majority translocating to developing shoots. However, in rush skeletonweed, early translocation was directed to root tissue. In rush skeletonweed, no DPX-MAT28 metabolism occurred, while DPX-KJM44 was rapidly de-esterified and translocated as DPX-MAT28. CONCLUSION: Aminocyclopyrachlor absorption and translocation are dependent on active ingredient structure and species sensitivity. Highly sensitive species such as prickly lettuce absorb and translocate less material than relatively less sensitive species such as rush skeletonweed. De-esterification of DPX-KJM44 appears to delay translocation of the resulting acid in yellow starthistle and rush skeletonweed. Copyright © 2011 Society of Chemical Industry

A prototype multiresidue method based on fast extraction and dilution of samples followed by flow injection mass spectrometric analysis is proposed here for high-throughput chemical screening in complex matrices. The method was tested for sulfonylurea herbicides (triflusulfuron methyl, azimsulfuron, chlorimuron ethyl, sulfometuron methyl, chlorsulfuron, and flupyrsulfuron methyl), carbamate insecticides (oxamyl and methomyl), pyrimidine carboxylic acid herbicides (aminocyclopyrachlor and aminocyclopyrachlor methyl), and anthranilic diamide insecticides (chlorantraniliprole and cyantraniliprole). Lemon and pecan were used as representative high-water and low-water content matrices, respectively, and a sample extraction procedure was designed for each commodity type. Matrix-matched external standards were used for calibration, yielding linear responses with correlation coefficients (r) consistently >0.99. The limits of detection (LOD) were estimated to be between 0.01 and 0.03 mg/kg for all analytes, allowing execution of recovery tests with samples fortified at ≥0.05 mg/kg. Average analyte recoveries obtained during method validation for lemon and pecan ranged from 75 to 118% with standard deviations between 3 and 21%. Representative food processed fractions were also tested, that is, soybean oil and corn meal, yielding individual analyte average recoveries ranging from 62 to 114% with standard deviations between 4 and 18%. An intralaboratory blind test was also performed; the method excelled with 0 false positives and 0 false negatives in 240 residue measurements (20 samples × 12 analytes). The daily throughput of the fast extraction and dilution (FED) procedure is estimated at 72 samples/chemist, whereas the flow injection mass spectrometry (FI-MS) throughput could be as high as 4.3 sample injections/min, making very efficient use of mass spectrometers with negligible instrumental analysis time compared to the sample homogenization, preparation, and data processing steps.

Bushkiller, an aggressive perennial vine native to Southeast Asia, has invaded several sites in Alabama, North Carolina, Texas, Louisiana, and Mississippi. Bushkiller has only recently been discovered in North Carolina. The potential economic and environmental consequences associated with established exotic invasive perennial vines and the lack of published control measures for bushkiller prompted research to be conducted at North Carolina State University that may be used in an early-detection rapid-response program. Field and greenhouse studies were conducted to determine bushkiller response to selected foliar-applied herbicides. Field study 1 evaluated efficacy of glyphosate, triclopyr, triclopyr plus 2,4-D, triclopyr plus aminopyralid, and triclopyr plus glyphosate applied postemergence to bushkiller. No control was evident from any treatment at 10 mo after application. In a separate experiment, aminocyclopyrachlor, imazapyr, metsulfuron, sulfometuron, and sulfometuron plus metsulfuron were applied postemergence to bushkiller. Control with aminocyclopyrachlor, imazapyr, sulfometuron, and sulfometuron plus metsulfuron was 88 to 99% at 10 mo after application. Each treatment was also applied to bushkiller in a greenhouse trial. Aminocyclopyrachlor and triclopyr-containing treatments generally resulted in the greatest control, lowest dry weights, and shortest vine lengths among the treatments. These results indicate that several herbicides may be employed initially in an early-detection, rapid-response program for bushkiller. Additional research is needed to determine how effective these herbicides would be in multiple-season treatments that may be required at well established bushkiller infestation sites.

Field studies were conducted in Wyoming and Nebraska in 2007 through 2009 to evaluate winter wheat response to aminocyclopyrachlor. Aminocyclopyrachlor was applied at rates between 15 and 120 g ai ha−1 6, 4, and 2 mo before winter wheat planting (MBP). Redroot pigweed control was 90% with aminocyclopyrachlor rates of 111 and 50 g ha−1 when applied 4 or 2 MBP. Aminocyclopyrachlor at 37 g ha−1 controlled Russian thistle 90% when applied 6 MBP. At Sidney, NE, winter wheat yield loss was > 10% at all aminocyclopyrachlor rates when applied 2 or 4 MBP, and at all rates > 15 g ha−1 when applied 6 MBP. At Lingle, WY, > 40% winter wheat yield loss was observed at all rates when averaged over application timings. Although the maturing wheat plants looked normal, few seed were produced in the aminocyclopyrachlor treatments, and therefore preharvest wheat injury ratings of only 5% corresponded to yield losses ranging from 23 to 90%, depending on location. The high potential for winter wheat crop injury will almost certainly preclude the use of aminocyclopyrachlor in the fallow period immediately preceding winter wheat.

Aminocyclopyrachlor, a newly discovered synthetic auxin herbicide, and its methyl ester, appear to control a number of perennial broadleaf weeds. The potential volatility of this new herbicide and its methyl ester were determined under laboratory conditions and were also compared to dicamba and aminopyralid with the use of enclosed chamber and open-air plant bioassays. Bioassays consisting of visual estimates of epinastic responses and kidney bean and soybean leaf-width measurements were developed to measure vapor release from glass and plastic. Vapor release of aminocyclopyrachlor from glass surfaces was undetectable under laboratory conditions, and no phytotoxic responses were observed when plants were exposed to vapors emanating from various surfaces. Results were similar to those of aminopyralid, indicating the risk of plant injury from vapor movement of aminocyclopyrachlor and aminopyralid was very low. When combined with 1% methylated seed oil, vapor release of aminocyclopyrachlor-methyl ester reached 86% 192 h after application to glass surfaces. Phytotoxic responses of plants exposed to vapors emanating from various surfaces treated with aminocyclopyrachlor-methyl ester were similar to responses to dicamba under enclosed incubation conditions, but were less in outdoor, open-air environments. Studies are needed to understand better the risk of injury to nontarget plants due to vapor movement of aminocyclopyrachlor-methyl ester under field applications.

Analytical methods have been developed for the detection and quantitation of a new herbicide active ingredient, aminocyclopyrachlor, and its analogue aminocyclopyrachlor methyl in environmental samples. The analytes were purified from soil extracts and water samples using solid phase extraction based on mixed-mode cation exchange/reverse phase retention. Analyte identification and quantitative analyses were performed by high performance liquid chromatography coupled to tandem mass spectrometry by an electrospray ionization source. External standards prepared in neat solvents were used for quantitation, providing acceptable accuracy, with no matrix effects observed during method validation. The method limits of quantitation (LOQ) were 0.10 ng/mL (ppb, parts-per-billion) in water and 1.0 ng/g in soil for both compounds. The limit of detection (LOD) in water was estimated to be 20 ng/L (ppt, parts-per-trillion) for aminocyclopyrachlor and 1 ng/L for aminocyclopyrachlor methyl, while LODs in soil were 100 ng/kg and 10 ng/kg for aminocyclopyrachlor and aminocyclopyrachlor methyl, respectively. The stability of both compounds in various solvents was evaluated as part of method development. Tandem mass spectrometry experiments were also conducted to investigate the gas-phase fragmentation of aminocyclopyrachlor and its methyl analogue, and the results are reported. A statistical analysis of method validation data generated at two laboratories by multiple chemists authenticates the ruggedness and good reproducibility of the analytical procedures tested.

The raw sugarcane harvesting system has changed the dynamics of weed tillage for this crop, changing the predominant weed species and providing a barrier between the herbicide and the soil. Thus, this study has aimed to assess the influence of precipitation and sugarcane straw in the aminocyclopyrachlor and indaziflam herbicides control efficiency for the species Ipomoea trilobaand Euphorbia heterophylla. There were two trials, one for aminocyclopyrachlor and one for the indaziflam, both in the greenhouse at the campus of Faculdade Integrado in the Brazilian city of Campo Mourão, PR. Each experiment consisted of eight treatments with four replications. The treatments consisted of the combination of the presence of straw (10 t ha-1), capillary irrigation and rainfall simulation (20 mm). Assessments of control percentage of I.triloba and E.heterophylla were carried out, as well as the number of plants per pot. The aminocyclopyrachlor and indaziflam herbicides applied directly to the soil were efficient in controlling these species. The 20 mm rainfall simulation or daily irrigation on the straw are indispensable to promote the removal of aminocyclopyrachlor and indaziflam from the straw and provide satisfactory control of I.triloba and E.heterophylla. RESUMOO sistema de colheita da cana crua modificou a dinâmica do manejo de plantas daninhas para essa cultura, alterando as espécies infestantes predominantes e proporcionando uma barreira entre o herbicida e o solo. Com isso, o presente trabalho teve por objetivo avaliar a influência da precipitação e da palhada de cana-de-açúcar na eficiência de controle dos herbicidas aminocyclopyrachlor e indaziflam para as espécies Ipomoea triloba e Euphorbia heterophylla. Foram realizados dois ensaios, um para o aminocyclopyrachlor e outro para o indaziflam, ambos em casa de vegetação no campus da Faculdade Integrado de Campo Mourão - PR. Cada experimento foi composto por oito tratamentos com quatro repetições. Os tratamentos consistiram na combinação entre a presença de palha (10 t ha-1), a irrigação por capilaridade e a simulação de precipitação (20 mm). Foram realizadas avaliações de porcentagem de controle de I. triloba e E. heterophylla além de número de plantas por vaso. Os herbicidas aminocyclopyrachlor e indaziflam aplicados diretamente ao solo foram eficientes no controle dessas espécies. A simulação de precipitação de 20 mm ou a irrigação diária sobre a palha é indispensável para promover a retirada do aminocyclopyrachlor e indaziflam da palha e proporcionar controle satisfatório de I. triloba e E. heterophylla.

Multiple classes of commercially important auxin herbicides have been discovered since the 1940s including the aryloxyacetates (2,4-D, MCPA, dichlorprop, mecoprop, triclopyr, and fluroxypyr), the benzoates (dicamba), the quinoline-2-carboxylates (quinclorac and quinmerac), the pyrimidine-4-carboxylates (aminocyclopyrachlor), and the pyridine-2-carboxylates (picloram, clopyralid, and aminopyralid). In the last 10 years, two novel pyridine-2-carboxylate (or picolinate) herbicides were discovered at Dow AgroSciences. This paper will describe the structure activity relationship study that led to the discovery of the 6-aryl-picolinate herbicides Arylex™ active (2005) and Rinskor™ active (2010). While Arylex was developed primarily for use in cereal crops and Rinskor is still in development primarily for use in rice crops, both herbicides will also be utilized in additional crops.

On the Hawaiian Islands, groundwater is the principal source of potable water and contamination of this key resource by pesticides is of great concern. To evaluate the leaching potential of four weak acid herbicides [aminocyclopyrachlor, picloram, metsulfuron-methyl, biologically active diketonitrile degradate of isoxaflutole (DKN)] and two neutral non-ionizable herbicides [oxyfluorfen, alachlor], their sorption coefficients were determined on three prevalent soils from the island of Oahu. Metsulfuron-methyl, aminocylcopyrachlor, picloram, and DKN were relatively low sorbing herbicides (K(oc) = 3-53 mL g(-1)), alachlor was intermediate (K(oc) = 120-150 mL g(-1)), and oxyfluorfen sorbed very strongly to the three soils (K(oc) > 12,000 mL g(-1)). Following determination of K(oc) values, the groundwater ubiquity score (GUS) indices for these compounds were calculated to predicted their behavior with the Comprehensive Leaching Risk Assessment System (CLEARS; Tier-1 methodology for Hawaii). Metsulfuron-methyl, aminocyclopyrachlor, picloram, and DKN would be categorized as likely leachers in all three Hawaiian soils, indicating a high risk of groundwater contamination across the island of Oahu. In contrast, oxyfluorfen, regardless of the degradation rate, would possess a low and acceptable leaching risk due to its high sorption on all three soils. The leaching potential of alachlor was more difficult to classify, with a GUS value between 1.8 and 2.8. In addition, four different biochar amendments to these soils did not significantly alter their sorption capacities for aminocyclopyrachlor, indicating a relatively low impact of black carbon additions from geologic volcanic inputs of black carbon. Due to the fact that pesticide environmental risks are chiefly dependent on local soil characteristics, this work has demonstrated that once soil specific sorption parameters are known one can assess the potential pesticide leaching risks.

The occurrence of herbicide resistance weeds across the southern United States has been increasing. Research is needed to develop alternative control measures, while supporting sound agronomic practices. Greenhouse and field studies were conducted to evaluate cereal cover cropping techniques along with novel herbicides to determine their value for Mississippi growers. Field studies were performed to determine which combination of cereal cover crops (cereal rye, wheat and oats) and residual herbicides (S-metolachlor + metribuzin, S-metolachlor + fomesafen, pendimethalin, flumioxazin, sulfentrazone + metribuzin and pyroxasulfone + flumioxazin) would maximize soybean yield in the presence of weeds. Cereal cover crop termination methods were evaluated and a partial budget was generated to examine the total costs of growing soybeans utilizing cereal cover crops and residual herbicides. Residual herbicide applications averaged across all cereal cover crops controlled Amaranthus spp. greater than 89% by 28 DAT. Control by the cover crops alone was 67% for of Amaranthus spp. In all cereal species tested, cutting the cover crops 10 cm above the soil and leaving the residue reduced weed numbers compared to other termination methods. However, high production and implementation costs may prevent widespread adoption of cereal cover crops and residual herbicides in Mississippi. Aminocyclopyrachlor (AMCP) is a synthetic auxin herbicide currently labeled for non-crop use, but has characteristics which may make it useful as a preplant burndown (PPB) herbicide. The application of AMCP prior to planting of corn and cotton were evaluated and carryover effects to soybean were also evaluated. Tank mix combinations of AMCP with residual herbicides (rimsulfuron, flumioxazin, pyroxasulfone, pyroxasulfone+ flumioxazin and atrazine) were also evaluated. A rate titration of AMCP and its impacts on crop species were evaluated in the greenhouse. Corn showed tolerance to AMCP except at 0.28 kg ai ha-1 applied prior to planting. Cotton was sensitive to AMCP as rate increased closer to the planting date, but response depended upon soil texture. AMCP impacts on soybean showed greater sensitivity (90% injury) then all other species evaluated. Due to potential impacts on soybean and cotton, AMCP is not a potential PPB for use in Mississippi.

Turfgrass managers applying aminocyclopyrachlor for annual and perennial broadleaf weed control in cool-season turfgrasses may want to reseed into treated areas. Field experiments were conducted in Georgia), Tennessee, and Texas to investigate perennial ryegrass (Lolium perenne L.) and tall fescue (Festuca arundinacea Schreb.) reseeding intervals after aminocyclopyrachlor applications. Perennial ryegrass and tall fescue establishment were similar to the non-treated control after treatments of aminocyclopyrachlor and 2,4-dichlorophenoxyacetic acid (2,4-D) + dicamba + methylchlorophenoxypropionic acid (MCPP) at 0, 2, 4, or 6 weeks before seeding. Results demonstrate that no reseeding interval is required after aminocyclopyrachlor treatment. Perennial ryegrass and tall fescue can be safely seeded immediately after aminocyclopyrachlor treatment at 39, 79, and 158 g/a.i./ha.

6 páginas.-- 2 figuras.-- 4 tablas.-- 42 referencias, The many advantageous properties of biochar have led to the recent interest in the use of this carbonaceous material as a soil amendment. However, there are limited studies dealing with the effect of biochar on the behavior of pesticides applied to crops. The objective of this work was to determine the effect of various biochars on the sorption-desorption of the herbicides aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinacarboxylic acid) and bentazone (3-isopropyl-1. H-2,1,3-benzothiadiazin-4(3. H)-one 2,2-dioxide) and the fungicide pyraclostrobin (methyl 2-[1-(4-chlorophenyl) pyrazol-3-yloxymethil]- N-methoxycarbanilate) to a silt loam soil. Aminocyclopyrachlor and bentazone were almost completely sorbed by the soils amended with the biochars produced from wood pellets. However, lower sorption of the herbicides was observed in the soils amended with the biochar made from macadamia nut shells as compared to the unamended soil, which was attributed to the competition between dissolved organic carbon (DOC) from the biochar and the herbicides for sorption sites. Our results showed that pyraclostrobin is highly sorbed to soil, and the addition of biochars to soil did not further increase its sorption. Thus, addition of biochars to increase the retention of low mobility pesticides in soil appears to not be necessary. On the other hand, biochars with high surface areas and low DOC contents can increase the sorption of highly mobile pesticides in soil. © 2013 Elsevier B.V., Projects: PAIDI-AGR-264 from Junta de Andalucía, AGL 2010-21421 from MICINN co-financed by the European Structural and Social Funds (FEDER-FSE), and i-LINK0025 from CSIC. A. Cabrera thanks the MICINN/FECYT for a postdoctoral fellowship.

Sorption and desorption of aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid) were compared to that of the structurally similar herbicide picloram (4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid) in three soils of differing origin and composition to determine if picloram data is representative of aminocyclopyrachlor behavior in soil. Aminocyclopyrachlor and picloram batch sorption data fit the Freundlich equation and was independent of concentration for aminocyclopyrachlor (1/n = 1), but not for picloram (1/n = 0.80-0.90). Freundlich sorption coefficients (K f) for aminocyclopyrachlor were lowest in the eroded and depositional Minnesota soils (0.04 and 0.12 μmol ((1-1/n)) L(1/n) kg(-1)) and the highest in Molokai soil (0.31 μmol ((1-1/n)) L(1/n) kg(-1)). For picloram, K f was lower in the eroded (0.28 μmol ((1-1/n)) L(1/n) kg(-1)) as compared to the depositional Minnesota soil (0.75 μmol ((1-1/n)) L(1/n) kg(-1)). Comparing soil to soil, K f for picloram was consistently higher than those found for aminocyclopyrachlor. Desorption of aminocyclopyrachlor and picloram was hysteretic on all three soils. With regard to the theoretical leaching potential based on groundwater ubiquity score (GUS), leaching potential of both herbicides was considered to be similar. Aminocyclopyrachlor would be ranked as leacher in all three soils if t1/2 was12.7 days. To be ranked as non-leacher in all three soils, aminocyclopyrachlor t1/2 would have to be3.3 days. Calculated half-life that would rank picloram as leacher was calculated to be ∼15.6 d. Using the current information for aminocycloprachlor, or using picloram data as representative of aminocycloprachlor behavior, scientists can now more accurately predict the potential for offsite transport of aminocycloprachlor.

4 pages, 4 references. Functions of Natural Organic Matter in Changing Environment presents contributions from the 16th Meeting of the International Humic Substances Society (IHSS 16) held in Hangzhou, China on September 9-14, 2012., Use of carbonaceous amendments in soil has been proposed to decrease potential off-site transport of weak acid herbicides and metabolites by increasing their sorption to soil. The effects of organic olive mill waste, biochars from different feed stocks, and humic acid bound to clay on sorption of 4-chloro-2-methylphenoxyacetic acid (MCPA), aminocyclopyrachlor, or indaziflam acid metabolite to soils with varying physical and chemical properties were determined. At natural agricultural pH soil levels, these chemicals are anionic and weakly sorbed to soils; sorption of the three weak acids on soil was in the order MCPA (K f = 0.1) < aminocyclopyrachlor (K f = 0.3) < indaziflam acid (K f = 1.6). Results indicate that not all carbonaceous amendments, including biochars, increase sorption, thereby decreasing the potential for off-site transport. The amount and composition of the organic amendment, along with pH of the system, affect sorption and potential off-site transport. For instance, depending on the feedstock of the biochar and the method of production, changes in sorption ranged from no effect, to a decrease by a factor of 3.3×, to an increase of 383× upon addition of amendment to soil. In contrast, activated charcoal increased sorption by >10,000×. While generalizations have been made that soil sorption of nonpolar, neutral, or weakly basic chemicals increases by the addition of different carbonaceous amendments, no such generalizations can be made for weak acids. More work on properties of these amendments, biochars in particular, and how they affect weak acid sorption is required.

Aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid), a new herbicide, was approved by US-EPA (United States Environmental Protection Agency) in September 2010 for the control of broadleaf weeds, grasses, vines and woody species in non-crops, turf, sod farms and residential areas. At typical soil pH levels, aminocyclopyrachlor is anionic. Anionic pesticides are generally weakly retained by most soil and sediment components and are subject to potential transport offsite. One strategy to minimize the risk of offsite transport associated with weakly sorbed, highly mobile pesticides is the application of these chemicals supported on a sorbent, such as modified clay minerals which contain exchangeable inorganic and organic cations. The aim was to determine the ability of unmodified and modified clay minerals to sorb aminocyclopyrachlor. Two montmorillonites (Ca-Arizona montorillonite (SAz-1) and Na-Wyoming montmorillonite (SWy-2)) were used as unmodified clay minerals and were also modified with an inorganic cation (Fe 3+), soil constituents (ferrihydrite, humic acid) and organic cations (hexadecyltrimethylammonium (HDTMA), hexadimethrine, spermine). Greater sorption of aminocyclopyrachlor was observed in the sorbent-solution systems with lower pH values, presumably because of protonation of the herbicide anion at low pH and subsequent sorption of molecular species and cationic species. FeSWy-2 (SWy-2 montmorillonite saturated with Fe 3+; system pH = 4.6) was the best sorbent for aminocyclopyrachlor (86% of applied). The best organo-clay (SA-HDTMA) (system pH = 6.1) sorbed 53% of the applied herbicide. Binary and ternary model sorbents (system pH > 6.7) did not sorb aminocyclopyrachlor. At the lowest pH value studied (2.8), the organo-clay SW-Sper was the best sorbent system for aminocyclopyrachlor. Our recommendation for the best adsorbent is the clay mineral modified with Fe 3+, although at pH values

Aminocyclopyrachlor sorption/desorption was investigated in 14 soils from Brazil, representing a range of pH, and organic carbon (OC) and clay contents. The Freundlich equation adequately described behavior of aminocyclopyrachlor in soil. Freundlich sorption coefficient (K(f)) values ranged from 0.06 to 1.64 and 1/n values for ranged from 0.9 to 1.0. Sorption was correlated to OC (K(f,oc) ranged from 11 to 64) and clay contents. The lowest sorption was found for soils with very low OC contents (0.50-0.65%) and loamy-sand to sand textures. The 1/n values for desorption were lower than those observed for sorption, suggesting that aminocyclopyrachlor sorption by soil was not reversible; hysteresis coefficients ranged from 0.13 to 0.74. The results suggest that although aminocyclopyrachlor would be very mobile based on its sorption coefficients, its potential depth of leaching may be overestimated due to the hysteretic desorption.