Grass Herbicides Research Articles

Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles.

A novel series of substituted 3-phenyl benzoylpyrazoles were prepared and tested as potential grass herbicides. The targeted materials were prepared by three newly developed synthetic routes, which allowed a comprehensive study of the SAR (structure-activity relationships) of this series. The best combination of grass weed activity (Avena fatua L, Setaria viridis (L) Beauv and Alopecurus myosuroides Huds) and wheat selectivity was obtained with an alkoxy group in the 4-position of the phenyl ring. Activity was further enhanced by the presence of tert-butyl on the pyrazole and a methyl group at the C-2 position of the benzoyl moiety. The alkoxy-substituted 3-phenylbenzoylpyrazoles are a novel class of herbicides with potential utility for control of important grass weeds in cereals.

Texas Panicum (Panicum texanum) Control in Strip-Tillage Peanut (Arachis hypogaea) Production

Abstract Studies were conducted from 1999 through 2001 in Georgia to develop Texas panicum management systems in strip-tillage peanut production into a killed rye cover crop. The experimental design was a split-plot with four replications. Main plots were preemergence (PRE) herbicides for annual grass control—ethalfluralin, pendimethalin, metolachlor, alachlor, dimethenamid, and a nontreated PRE control. All plots were irrigated immediately after PRE applications to activate herbicides. Subplots were postemergence (POST) graminicides applied 28 d after peanut emergence—sethoxydim, clethodim, and a nontreated POST control. POST graminicides were applied with a crop oil concentrate. None of the PRE herbicides alone adequately controlled Texas panicum in strip-till peanut production, even with optimum activation with irrigation. Sethoxydim and clethodim controlled Texas panicum at least 91%, regardless of PRE treatments. Peanut yields were greater where ethalfluralin or pendimethalin PRE were applied sequentially with a POST graminicides, compared to PRE herbicides or POST graminicides alone. This suggests that, while POST graminicides effectively control Texas panicum, the reduced efficacy of dinitroaniline herbicides is still beneficial. The additional cost of a POST graminicide needs to be factored into production budgets for strip-tillage peanut production.

Susceptibility of a broad‐leaved weed, Acanthospermum hispidum, to the grass herbicide fluazifop‐butyl

Broad‐leaved plants are generally resistant to aryloxyphenoxypropionate (AOPP) and cyclohexanedione (CHD) herbicides. In laboratory experiments, however, we confirmed that Acanthospermum hispidum, a Compositae weed, was susceptible to one of the AOPP herbicides, fluazifop‐butyl, but tolerant to other AOPP herbicides (quizalofop‐ethyl and fenoxaprop‐ethyl) and a CHD herbicide (sethoxydim). The symptoms induced by fluazifop‐butyl in A. hispidum (wilting and necrosis) were distinctly different from those induced in oat (chlorosis). The period required to cause seedling death of A. hispidum (48–72 h) was shorter than that of oat (ca 15 days). The (R)‐enantiomer of fluazifop‐butyl was more active on this weed. In oat, lipid biosynthesis and acetyl‐CoA carboxylase (ACCase) activity were inhibited, and electrolyte leakage from the shoots was increased by fluazifop‐butyl and sethoxydim. In the case of A. hispidum, the membrane permeability increased and the lipid biosynthesis was inhibited only by fluazifop‐butyl. These results indicate that A. hispidum is particularly sensitive to fluazifop‐butyl, and its mechanism of action in the plant may be different from its mechanism of action in oat.

Weed management at the time of perennial cereal rye establishment

Perennial cereal rye (PC rye) is a new crop that is being developed at the Lethbridge Research Centre for the production of silage for cattle. Its ability to compete with weeds during establishment and tolerance to herbicides for weed control was unknown. Therefore, experiments were established with PC rye, and several herbicide treatments were applied to test crop tolerance and weed control. PC rye was not injured by bromoxynil/MCPA, 2,4-D, thifensulfuron/tribenuron, fenoxaprop, clodinafop-propargyl, and tralkoxydim. Combinations of herbicides for broadleaf weed control and annual grass control usually reduced weed dry matter (DM) to < 5 g m-2 in the establishment year. Weeds made up 20 to 36% of the total DM when herbicides were not applied. However, this level of weed content did not affect the digestibility of the forage samples or the total DM produced as weed DM compensated for reduced PC rye yield in weedy plots. Also, the presence of weeds during establishment of PC rye did not affect weed content or PC rye yields the year after establishment. Key words: Acid detergent fibre, digestibility, neutral detergent fibre, perennial cereal rye, weed control, yield

Tolerance to Quinclorac by Seedling Creeping Bentgrass

Annual grassy weeds often inhibit establishment of spring-seeded creeping bentgrass (Agrostis palustris Huds.) on golf courses. The objective of this experiment was to evaluate the safety of the annual grass herbicide quinclorac in spring-seeded creeping bentgrass in varying climatic regions of the United States. Experiments were initiated in Indiana, Iowa, and North Carolina in Spring 2000. Treatments included siduron at 6.72 kg·ha-1 a.i. applied immediately prior to planting (PRE), and quinclorac at 0.84 kg·ha-1 a.i. applied 7 days before seeding (DBS), PRE, and 14 or 28 days after emergence (DAE). Herbicides were applied to three creeping bentgrass cultivars at each location. Siduron reduced establishment of `Providence', `L93', and `Putter' creeping bentgrass in Indiana. Quinclorac applied PRE, 14 DAE, and 28 DAE caused short-term phytotoxicity, primarily in `Providence' in Indiana. Quinclorac applications did not significantly affect cover of `Providence', `L93', or `Putter' in Indiana or `L93', `Pennlinks', or `Penncross' in Iowa. All applications of quinclorac reduced cover of `L93', `Pennlinks', and `Penncross' in North Carolina. Though quinclorac applications resulted in no long-term damage when applied to creeping bentgrass seedlings in Indiana or Iowa, results from North Carolina indicate that caution should be exercised when using quinclorac on seedlings of creeping bentgrass. Chemical names used: 3,7-dichloro-8-quinolinecarboxylic acid (quinclorac); 1-(2-methylcyclohexyl)-3-phenylurea (siduron).

The Chiral Switch of (S)-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric Catalysis

This account chronicles the various development phases of the Ir-catalyzed enantioselective hydrogenation for the production of (S)-metolachlor, the active ingredient of Dual Magnum® (one of the most important grass herbicides for use in maize). The final process is today's largest application of asymmetric catalysis and the Ir-xyliphos catalyst achieves unprecedented ton's of 2,000,000 and tof values around 600,000 h−1. The development started in 1982 and ended when the first production batch was run in November 1996. On the one hand, the paper recounts the various breakthroughs and set-backs and how the final catalytic system slowly evolved, and discusses on the other hand the strategies and approaches used for attaining the elusive goal. The various actions and decision points are analyzed and commented, and the roles and the seminal contributions of three key team members, Felix Spindler, Benoit Pugin, and Hans-Peter Jalett are presented.

Seletividade de herbicidas a cinco tipos de gramas

Dentre as opções de controle de plantas daninhas em gramados, destaca-se o uso de herbicidas, porém poucas informações existem na literatura sobre a sua seletividade a gramados. Assim, foi desenvolvida a presente pesquisa em casa de vegetação da ESALQ - Piracicaba, com o objetivo de testar a seletividade de herbicidas aplicados em pré-plantio (sulfentrazone a 1,4 kg i.a. ha-1 e oxadiazon a 1,0 kg i.a. ha-1) e em pós-emergência (halosulfuron a 112,5 g i.a. ha-1, 2,4-D a 2,010 kg i.a. ha-1 e MSMA a 2,4 kg i.a. ha-1), em cinco espécies de gramas (família Poaceae): são-carlos (Axonopus affinis), esmeralda (Zoysia japonica), bermuda (Cynodon dactylon), zoysia (Zoysia matrella) e santo-agostinho (Stenotaphrum secundatum). As conclusões gerais deste trabalho de pesquisa foram de que a seletividade de herbicidas aos diversos tipos de grama é função principalmente da espécie de grama e do tipo e da dose do herbicida aplicado. Dentre os herbicidas testados, destacam-se como mais seletivos o halosulfuron na dose de 112,5 g i.a. ha-1 e o 2,4-D na de 2,010 kg i.a. ha-1; as espécies de grama do gênero Zoysia (esmeralda [Z. japonica] e zoysia [Z. matrella]), de maneira geral, são mais tolerantes aos herbicidas testados nesta pesquisa.

Weed Community as an Indicator of Summer Crop Yield and Site Quality

We studied relationships between weed community characteristics and management practices, soil degradation (reductions of the A horizon, organic matter, total N, and available P) levels, and soybean [Glycine max (L.) Merr.] and corn (Zea mays L.). Our objective was to provide a scale based on floristic information that could be used to evaluate sites in terms of summer crop yields and agroecosystem degradation. Weed surveys were carried out in 1995 and 1999 in corn and soybean fields. Cluster analysis and canonical correspondence analysis (CCA) were used with data from 1995. Regional or gamma diversity, local or alpha diversity, and exchange of species between habitats or beta diversity of weed communities were estimated as well as changes in origin, morphotype, and life cycle for data from both surveys. Four weed communities related to crops and yields were identified. In both corn and soybean fields, the potential for high crop yield (low soil degradation) may be indicated by the presence of the weed groups identifying the weed community of a crop species. Sowing date, agronomic index, mechanical control, and the use of grass herbicide also accounted for weed community structure. Sites with higher than average yield had the highest alpha diversity. The number of native species in the community was related to soil degradation levels. Soil degradation proved to be more important than type of crop in determining the structure of a weed community.

7-(4,6-Dimethoxypyrimidinyl)oxy- and -thiophthalides as novel herbicides: Part 1. CGA 279 233: a new grass-killer for rice.

A series of novel types of 7-(4,6-dimethoxypyrimidin-2-yl)oxy- and -thio-3-methyl-1 (3H)-isobenzofuranones were discovered at Dr R Maag AG. From the thio-isobenzofuranyl series, CGA 279 233--BSI-proposed common name pyriftalid--was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid-derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico-chemical behaviour.

Use of Herbicides and Plant Growth Regulators to Suppress Italian Ryegrass Growth

Several concentrations of mefluidide (Embark), a plant growth regulator; sethoxydim (Poast), a grass herbicide; and triclopyr (Rely) a nonselective herbicide, were evaluated to determine if italian ryegrass (Lolium multiflorum Lam.) growth could be suppressed. Ryegrass grows prolifically during the winter in states adjacent to the Gulf of Mexico and may serve as a living mulch for strawberry (Fragaria×ananassa Duch.) and other winter crops if its growth can be controlled. Different chemicals and concentrations were screened over 5 years for their efficacy to produce living mulch. Mefluidide produced good ryegrass control but was not evaluated after Study 1 because it is designed for industrial use and does not have an U.S. Environmental Protection Agency fruit crop label. Triclopyr, which has a label for several fruit crops, was studied only in the final year and it provided desired ryegrass control at the 0.016 and 0.030 mL·L-1 (parts per thousand) rate. Prime oil (paraffin base petroleum oil + polyol fatty acid esters) concentration affected results when sprayed with various sethoxydim rates. We concluded that 0.156 mL·L-1 sethoxydim plus 0.25 mL·L-1 prime oil will control ryegrass growth at the desired level (reduce growth by 40% to 50%) for living mulch. These rates are too low to cause much ryegrass browning. Chemical names used: N-[2,4dimethyl-5-[[(trifluoromethyl)-sulfony]amino]phenyl]acetamide, 2-[1-(ethoxylmino)buty1]-5-[2-(ethylthio)propy1]-3-hydroxy-2-cyclohexen-1-one), and ammonium-Dl-homoalanin-4-yl-(methyl) phosphinate.

283 Response of Forbs to Grass Herbicides, Fire, and Mowing in Mid-successional Tallgrass Prairies of Central Missouri

Because of thousands of years of adaptation to the native climate, prairie forbs (“wildflowers”) present a large potential for their use in beautification projects along roadsides, in large backyards, and in nature centers. Vegetation in abandoned, naturally revegetated, grass-dominated areas can be managed to encourage a forb-dominated stage. Two grass herbicides [sethoxydim (PoastTM) and fluazifop (Ornamec-170TM)], three burning treatments (winter, early spring, and late spring), and two mowing treatments (fall and late spring) were tested to determine their effect on forb cover and species diversity in a mid-successional tallgrass prairie. One application of either of the herbicides, at the time of recommended growth stage of target grasses, changed species composition significantly (80% forbs vs. 46% forbs in control plots; P < 0.05) in favor of showy forbs. Species diversity of sprayed plots was relatively low, however. Burning was the next best alternative (averaging 63% forbs) that also resulted in highest species diversity. Fall and late spring mowing reduced cover of forbs (32%) and species diversity to levels lower than those found in control plots. Cover of Solidago canadensis (tall goldenrod) in sethoxydim-treated plots increased to 22.8% compared to 2.5% in control plots. Cirsium discolor (pasture thistle) and Rudbeckia hirta (black-eyed susan) also increased significantly in response to herbicide treatments.

An Integrated Weed Management Approach to Managing Foxtail Barley (Hordeum jubatum) in Conservation Tillage Systems

A 4-yr field experiment was conducted to determine the merits of combining cultural and chemical controls to manage foxtail barley in reduced-tillage systems. Factors studied were crop row spacing, seeding rate, and application rate and timing of glyphosate within a spring wheat-flax cropping sequence. Glyphosate applied preseeding at 400 or 800 g/ha killed foxtail barley seedlings but only suppressed established perennial plants. Glyphosate applied postharvest at 800 g/ha killed 60 to 70% of established plants. Combinations of preseeding and postharvest glyphosate gave the greatest reductions in foxtail barley biomass and seed production and resulted in the greatest increases in crop yield. Including flax in the rotation allowed use of grass herbicides such as quizalofop or sethoxydim that effectively controlled foxtail barley seedlings and provided some suppression of perennial plants. An increase in wheat seeding rate from 75 to 115 kg/ha reduced foxtail barley growth and increased wheat yield in 3 of 4 yr. Increasing the flax seeding rate from 40 to 80 kg/ha or reducing wheat and flax row spacing from 30 to 20 cm provided little benefit in managing foxtail barley or increasing crop yield. A multiyear approach combining agronomic practices and timely use of herbicides should allow growers to effectively manage foxtail barley in annual cropping systems using conservation tillage.

PALWEED: WHEAT II: revision of a weed management decision model in response to field testing

PALWEED:WHEAT is a bioeconomic decision model for determining profit-maximizing postemergence herbicide treatments for winter wheat in the Washington–Idaho Palouse region. PALWEED:WHEAT performed relatively well economically in 2 yr of on-farm field tests. However, the model was less sensitive than desired in prescribing postemergence broadleaved herbicides in the presence of high densities of broadleaved weed seedlings. Therefore, PALWEED:WHEAT was revised in response to the field testing. This paper compares the revised model's agronomic and economic performance to the original model in computer simulations. The revised model, PALWEED:WHEAT II, differs from the original model in several respects: (1) exponential functions replace linear functions in predicting weed survival, (2) preplant application of a nonselective herbicide is entered as an exogenous binary variable, (3) separate indices of broadleaved and grass competition are substituted for an aggregate weed competition index in the wheat yield function, (4) hyperbolic replaces logistic functional representation of weed damage to wheat yield, and (5) separate models are estimated for winter wheat after spring dry pea and for winter wheat in all examined crop rotation positions. In simulations including a variety of agronomic and economic conditions, PALWEED:WHEAT II recommended postemergence herbicide types and rates that consistently complied with agronomic and economic theory. Furthermore, the revised model, especially when estimated from the relevant wheat after pea data set, was markedly more balanced in recommending both broadleaved and grass herbicides in response to observed densities of both weed groups. The substantial change in herbicide recommendations in response to changes in model functional specifications following field testing confirms the importance of field testing and revision of bioeconomic decision models.

Giant foxtail (Setaria faberi) control in sethoxydim-resistant corn (Zea mays)

Field studies were conducted at Dekalb and Urbana, IL, in 1995 and 1996 to evaluate the effectiveness of sethoxydim for giant foxtail control in sethoxydim-resistant (SR) corn. Experiments studied sequential and total postemergence applications of grass herbicide standards compared to sethoxydim. Additional studies evaluated the compatibility of sethoxydim with postemergence broadleaf herbicides. Metolachlor plus atrazine and metolachlor followed by dicamba plus atrazine gave at least 88% control of giant foxtail at both locations in both years. Metolachlor plus flumetsulam plus clopyralid provided 90% or greater grass control over all experiments, with the exception of only 75% control at Dekalb in 1995 due to a heavy giant foxtail infestation. In comparison, flumetsulam plus clopyralid followed by postemergence applications of sethoxydim or nicosulfuron provided the same level of grass control as preemergence metolachlor, except at Dekalb in 1995 where control was 72% for both sethoxydim and nicosulfuron. Sequential applications of sethoxydim increased control of giant foxtail compared to a single sethoxydim application in 1995. Sethoxydim applied alone controlled giant foxtail 8% better than nicosulfuron at Urbana in 1996. Postemergence sethoxydim applied alone provided 87% or better control of giant foxtail. Sethoxydim performance was consistent when applied with flumetsulam plus clopyralid plus 2,4-D (NAF-73), halosulfuron plus dicamba, and bromoxynil. The efficacy of sethoxydim was reduced in combination with dicamba plus atrazine in three of the four trials, and bentazon plus atrazine as well as primisulfuron plus prosulfuron in all trials. Sethoxydim outperformed nicosulfuron in combinations with bromoxynil at Urbana. These studies indicate sethoxydim has excellent potential to be used in corn for postemergence control of giant foxtail.

Evaluation of Herbicides for Phytotoxicity to Rose Plants and Efficacy

Roses are likely the most popular garden plant in the United States, and cultivars are also used as landscape plant materials. Three herbicide trials with two main objectives were conducted with rose plants. The first objective was to evaluate injury to the roses when over-sprayed at various stages of growth. The second objective was to evaluate the efficacy of the herbicides. All herbicides were used at label rates and applied over the top of rose plants. In the first trial, the pre-emergent herbicides pendimethalin, oryzalin, trifluralin, metolachlor, napropamide, and oxyfluorfen were applied to plots containing dormant roses with ≈1-cm shoots just pushing. Evaluations of shoot length taken over the next 6 weeks showed no differences in growth of rose plants, but weed populations were reduced. In the second trial, five post-emergent herbicides were applied to plots containing dormant roses. Herbicides evaluated included the grass herbicides fluazifop-p-butyl, sethoxydim, and clethodim. The nonselective herbicide glyphosate was included in the trial, as was a combination herbicide containing 2,4-D, mecoprop, and dicamba. There was no visible injury to rose plants until 6 weeks after treatment. At that time, roses treated with glyphosate had shorter shoots. Recovery from glyphosate appeared more rapidly than recovery from the combination herbicide. Weed control varied with each herbicide. The third trial evaluated the same five herbicides for control of bermudagrass in late spring. Injury to roses was noted immediately from the combination herbicide and glyphosate. All the grass herbicides and glyphosate were effective in controlling bermudagrass.

Noxious Weed Population Dynamics Education Model

An educational software program was developed to demonstrate the interactions among weed population demographic processes, plant community interactions, and grassland noxious weed management options. The software includes an example model parameterized to simulate yellow starthistle population dynamics and graphic output. The software allows students to change weed and competing grass population demographic parameters, herbicide, and biological control management options. The graphic output allows the user to observe the outcome of integration of weed biology and various weed management options.

WEED INTERFERENCE AND WEED PROBLEMS IN LOUISIANA SWEETPOTATOES—A REVIEW

High annual rainfall and frequent torrential deluges have always made weed control a tenuous affair in Louisiana. Herbicide leaching and soil erosion often take preemergence herbicides to the nether regions. Before the time of postemergent grass herbicides, frequent cultivation was the only method to try to salvage the sweetpotato crop when preemergence weed control was lost. For many years, the most serious weed problems were prickly sida, cocklebur, and purple nutsedge with occasional hotspots of morning-glory. However, due to the change in herbicides used, the species of problem weeds have shifted to rice flatsedge, yellow and purple nutsedge, carpetweed, and various pigweeds. Before the registration of Command herbicide for use in sweetpotatoes, many sweetpotato growers used herbicides that effectively controlled or suppressed the current problem weeds. With the widespread use of Command, prior problem weed species are effectively controlled, but these other problem weeds are released.

Grass Herbicide Efficacy as Influenced by Adjuvant, Spray Solution pH, and Ultraviolet Light

Research was conducted at the Brandon Research Centre to determine the effect of spray solution pH or adjuvants on the efficacy of two cyclohexanedione (CHD) herbicides, clethodim and tralkoxydim, and two aryloxyphenoxypropionate (APP) herbicides, fenoxaprop-P and quizalofop, and if ultraviolet light is a factor influencing their activity. CHD herbicide efficacy decreased as spray solution pH increased above 7. APP herbicide efficacy was not affected by spray solution pH, probably due to their formulation as proherbicide esters. The choice of adjuvant affected CHD herbicide efficacy but not APP herbicide efficacy. Amigo®, Canplus-411® plus ammonium sulfate, and Merge® were usually the most effective adjuvants with the two CHD herbicides. Physical removal of ultraviolet light did not improve APP herbicide efficacy but did improve CHD herbicide efficacy.

Effects of Ultra-low Volume Application on Herbicide Efficacy Using Oil Diluents as Carriers

The efficacy of postemergence herbicide applications was evaluated in the greenhouse and the field in 1993 and 1994, using variables of carrier volume and diluent type. Ultra-low volume (ULV) applications of herbicides using an air-assisted sprayer calibrated at a volume of 9.4 L/ha were compared to 94 and 187 L/ha applications with a conventional hydraulic system. In greenhouse studies, reduced rates of sethoxydim, clethodim, fluazifop-P, and quizalofop were used to compare the effects of carrier types and volumes on their efficacy to yellow foxtail. All herbicides applied in oil diluents at 9.4 L/ha, with the exception of fluazifop-P and quizalofop applied in soybean oil, provided better yellow foxtail control than when applied in water at 94 and 187 L/ha. Sethoxydim and clethodim applied at 25 and 16% of the recommended rate, respectively, provided over 90% control in both petroleum oil and methylated seed oil. Reduced rates of glyphosate in petroleum oil or soybean oil were more effective at reducing bermudagrass growth than in water or methylated seed oil. Activity of glyphosate in methylated seed oil was no more effective than in water. Field experiments were conducted to study the efficacy of ULV applications of sethoxydim, clethodim, fluazifop-P, imazethapyr, and bentazon. Rates of the postemergence grass herbicides could be reduced by applying them at ULV in oil diluents while maintaining annual grass control equal to that achieved with higher herbicide rates in larger volumes of water. Control of annual grasses and annual broadleaf weeds with bentazon and imazethapyr applied at ULV were inconsistent and did not provide acceptable weed control. This may be partially due to the poor suspension of these herbicides in oil carriers.

Ethametsulfuron Interactions with Grass Herbicides on Canola (Brassica napus, B. rapa)

Field experiments were conducted from 1986 to 1988 at Lacombe and Lethbridge, Alberta and Scott, Saskatchewan to determine growth and yield response of canola to mixtures of ethametsulfuron with specific grass herbicides. Ethametsulfuron did not usually cause canola injury when mixed with sethoxydim. However, ethametsulfuron mixtures with the following grass herbicides listed in decreasing order of injury potential, often caused canola injury and yield loss: haloxyfop > fluazifop > fluazifop-P > quizalofop > quizalofop-P. Canola yield losses were severe in some experiments, ranging from 59% with quizalofop mixtures to 97% with haloxyfop mixtures; in other experiments, the same mixtures did not cause significant yield losses. ‘Tobin,’ aBrassica rapacultivar, tended to be more susceptible to injury than theB. napuscultivars ‘Pivot’ and ‘Westar.’ Canola injury symptoms were consistent with those expected from sulfonylurea herbicides. Therefore, we suggest that specific grass herbicides differentially impair the ability of canola to metabolize ethametsulfuron to inactive forms.