Selectivity and mode of action of carfentrazone-ethyl,a novel phenyl triazolinone herbicide

Post-emergence application of carfentrazone-ethyl at rates as low as 2·2 g ha^-1 caused greater leaf injury and growth reduction in ivyleaf morningglory (Ipomoea hederacea) and velvetleaf (Abutilon theophrasti) than in soybean (Glycine max). The herbicide was more rapidly metabolized in the crop than in the weed species, with 26·7, 54·3 and 60·6% of the parent compound remaining in soybean, ivyleaf morningglory and velvetleaf, respectively, 24 h after exposure. The free acid metabolite, carfentrazone, was present in all species and accounted for 21·2–27·4% of the total radioactivity. Unknown metabolites (R_f 0 and 0·22) were four to five times more abundant in soybean than in the weed species. Carfentrazone-ethyl induced more leakage from leaf discs from the weeds than those from soybean and the degree of injury correlated with the amount of protoporphyrin IX (Proto IX) present in the treated tissues. Both carfentrazone-ethyl and carfentrazone were potent inhibitors of protoporphyrinogen oxidase (Protox). Therefore, the selectivity of this herbicide may, at least in part, be attributed to the lower accumulation of Proto IX in soybean than in the weeds, probably because of the ability of soybean to metabolize more carfentrazone into unknown metabolites than the weeds. © 1997 SCI.     

On the mechanism of action and selectivity of the corn herbicide topramezone: a new inhibitor of 4-hydroxyphenylpyruvate dioxygenase

Topramezone is a new, highly selective herbicide of pyrazole structure for the post-emergence control of broadleaf and grass weeds in corn. The biokinetic properties and mode of action of topramezone were investigated in plants of Setaria faberi Herrm, Sorghum bicolor (L.) Moench, Solanum nigrum L. and the crop species corn (Zea mays L.). Within 2-5 days after treatment, topramezone caused strong photobleaching effects on the shoot, followed by plant death of sensitive weeds. The selectivity of topramezone between corn and the weed species has been quantified as above 1000-fold. By virtue of the plant symptoms and the reversal of the effects in Lemna paucicostata L. by adding homogentisate, it was hypothesized that topramezone blocks the formation of homogentisate, possibly through inhibition of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD). Indeed, topramezone strongly inhibited 4-HPPD activity in vitro, with I(50) values of 15 and 23 nM for the enzyme isolated from S. faberi and recombinant enzyme of Arabidopsis thaliana L. respectively. The enzyme activity from corn was approximately 10 times less sensitive. After root and foliar application of [(14)C]topramezone, equivalent to field rates of 75 g ha(-1), the herbicide was rapidly absorbed and systemically translocated in the plant. Only marginal differences between leaf uptake and translocation of topramezone by the weeds and corn were found. Metabolism of foliar-applied [(14)C]topramezone was far more rapid in corn than in the weeds. A more rapid metabolism combined with a lower sensitivity of the 4-HPPD target enzyme contributes to the tolerance of corn to topramezone.     

On the mechanism of selectivity of the corn herbicide BAS 662H: a combination of the novel auxin transport inhibitor diflufenzopyr and the auxin herbicide dicamba

BAS 662H, a 1:2.5 combination of the semicarbazone-type auxin transport inhibitor diflufenzopyr and the auxin herbicide dicamba, is used as a post-emergence herbicide in corn. The combination has been observed to provide more effective broadleaf weed control and improved tolerance in corn than typical rates of dicamba used alone. In order to analyze this phenomenon, the uptake, translocation, metabolism and action of both compounds, applied alone and in combination, were investigated in Amaranthus retroflexus L, Galium aparine L and corn (Zea mays L). When plants at the third-leaf stage were foliarly treated with diflufenzopyr and dicamba equivalent to field rates of 100 and 250 gha-1, respectively, diflufenzopyr synergistically increased dicamba-induced 1-aminocyclopropane-1-carboxylic acid (ACC) synthase activity and ethylene formation in G aparine and even more in A retroflexus, followed by accumulations of (+)-abscisic acid (ABA) in the shoot tissue within 20 h. This correlated with subsequent growth inhibition, hydrogen peroxide overproduction and progressive tissue damage. Diflufenzopyr also enhanced the activity of other auxin herbicides, such as quinclorac and picloram, and of the synthetic auxin, 1-naphthaleneacetic acid. After foliar and root application of [14C]diflufenzopyr, alone or as BAS 662H, considerably lower tissue concentrations and systemic translocation of radioactivity beyond treated plant parts were found in corn, compared to G aparine and particularly A retroflexus. Furthermore, diflufenzopyr decreased foliar uptake of [14C]dicamba by c 50% selectively in corn, compared to the treatment alone. Metabolism of [14C]diflufenzopyr was more rapid in corn than in the weed species. In combination, the two compounds had no mutual effect on their metabolic degradation. In BAS 662H, diflufenzopyr synergizes the herbicidal activity of dicamba in sensitive weed species. In corn this effect is prevented by a more rapid metabolism of diflufenzopyr, coupled with lower uptake and translocation. Selectivity of BAS 662H is additionally favoured by a higher crop tolerance to dicamba because of reduced foliar uptake of this herbicide in corn under the influence of diflufenzopyr.     

Uptake,translocation and metabolism of the herbicide molinate in tobacco and rice

Molinate, a selective herbicide, is used for the control of annual and perennial weeds in rice paddy fields. This study was designed to assess the basis of the selective action of molinate between a susceptible broadleaf crop, tobacco, and a resistant graminaceous plant, rice. Experiments were conducted comparing plant growth under different concentrations of molinate, determining the absorption and translocation of the herbicide in the plant and identifying the metabolites in suspension cells. Rice showed greater tolerance to molinate than tobacco. Leaves of tobacco showed retarded and distorted growth at 10 mg liter^-1 of molinate 14 days after treatment, but rice leaves were unaffected at this concentration. Higher concentrations of molinate accumulating in the root of tobacco seedlings may inhibit root development and represent a significant factor in the herbicide's selective action. Seven and eight metabolites were found in tobacco and rice cells, respectively, with molinate sulfoxide and molinate sulfone present in both species. © 1998 SCI     

Uptake, translocation and metabolism of the herbicide florasulam in wheat and broadleaf weeds

Florasulam is a triazolopyrimidine sulfonanilide post-emergence broadleaf herbicide for use in wheat (Triticum aestivum L.). The selectivity of florasulam to wheat has been determined to be related primarily to a differential rate of metabolism between wheat with a half-life of 2.4 h and broadleaf weeds with half-lives ranging from 19 to >48 h. To a lesser extent, selectivity, at least for the broadleaf weed cleavers (Galium aparine L.), involves uptake differences. Rate of metabolism data were generated using greenhouse-grown plants injected with radiolabelled florasulam and subsequent extraction and processing by high-performance liquid chromatography (HPLC). Structures of metabolites were determined by isolation for nuclear magnetic resonance and liquid chromatography/mass spectrometry. Wheat plants metabolised florasulam by hydroxylation of the aniline ring para to the nitrogen, followed by conjugation to glucose. Metabolism by broadleaf weeds was so slow that isolation of metabolite was not possible, but comparison of HPLC data suggested hydroxylation as the major pathway.     

Root exudation of diclofop-methyl and triasulfuron from foliar-treated durum wheat and ryegrass

In this study, we evaluated the release of diclofop-methyl and triasulfuron from the roots of foliar-treated ryegrass and wheat. The study with ¹⁴C-diclofop-methyl indicated a basipetal translocation of foliar-applied herbicide in wheat and ryegrass. No root exudation from ¹⁴C-diclofop-methyl-treated wheat plants was observed, while 20 days after treatment (DAT) 0.2–0.9% of radioactivity absorbed by ryegrass was found exuded in the growing medium. Root exudation was stimulated three to six times by the presence of untreated wheat or ryegrass sharing the growing medium with diclofop-methyl-treated ryegrass. No subsequent uptake of exuded radiolabel by untreated plants (ryegrass or wheat) in the same pot with ¹⁴C-diclofop-methyl-treated ryegrass was observed. The study with ¹⁴C-triasulfuron indicated a basipetal translocation of foliar-applied herbicide in wheat and ryegrass and also into the growing medium. By 20 DAT, 0.5–4.2% of radioactivity absorbed by wheat or ryegrass was found exuded in the growing medium. The presence of untreated plants (wheat or ryegrass) in the same pot as triasulfuron-treated ryegrass or wheat induced exudation seven to 32 times more. The study also revealed a subsequent uptake of exuded compounds by untreated wheat or ryegrass sharing the medium of ¹⁴C-triasulfuron-treated plants. This study has demonstrated for the first time that the root exudation of exogenous compounds can be related to plant arrangement in pots. The implication is that herbicide root exudation and transfer, a form of allelopathy, could be significant in the field. A precise estimation of environmental fate, unexpected ecological side effects and residual activity of herbicides may require quantification of such exudation.     

新型酰胺类除草剂NC1的除草作用及对水稻的安全性

为了明确新型除草剂NC1的杀草谱、施药时期、使用剂量及对水稻的安全性,采用种子生物测定法测定34.5％ NCI悬浮剂对稗草的生物活性,并与30乡丙草胺乳油进行比较;采用室内整株生物测定法测定34.5％NC1 SC不同时期处理对禾本科杂草的控制作用和对水稻的安全性,并进行田间验证.结果 表明:NC1对稗草种子的生物活性优...     

Biological activity of the new herbicide LGC-40863 {benzophenone O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime}

Herbicidal characteristics of the experimental compound LGC-40863 (ISO proposed common name: pyribenzoxim) were investigated in greenhouse and field. In the greenhouse, LGC-40863 had strong post-emergent activity on various grass and broadleaf weeds including Echinochloa crus-galli L. Beauv., Alopecurus myosuroides Huds. and Polygonum hydropiper L., while it was safe in rice (Oryza sativa L.), wheat (Triticum aestivum L.) and zoysiagrass (Zoysia japonica Steud; (a turf species). Among important rice weeds, E. crus-galli was controlled over a wide window from the one-leaf to the six-leaf stages. In the field, LGC-40863 provided excellent control of E. crus-galli (>95%) at 30 to 40 g ha^-1 when applied alone, or at 15 to 30 g ha^-1 when applied in combination with pendimethalin, while it did not cause injury to rice at up to 60 g ha^-1. These results suggest that LGC-40863 has potential as a new selective post-emergent herbicide in rice. © 1997 SCI     

Cuticular uptake of xenobiotics into living plants. Part 2: influence of the xenobiotic dose on the uptake of bentazone, epoxiconazole and pyraclostrobin, applied in the presence of various surfactants, into Chenopodium album, Sinapis alba and Triticum aestivum leaves

This study has determined the uptake of three pesticides, applied as commercial or model formulations in the presence of a wide range of surfactants, into the leaves of three plant species (bentazone into Chenopodium album L. and Sinapis alba L., epoxiconazole and pyraclostrobin into Triticum aestivum L.). The results have confirmed previous findings that the initial dose (nmol mm(-2)) of xenobiotic applied to plant foliage is a strong, positive determinant of uptake. This held true for all the pesticide formulations studied, although surfactant concentration was found to have an effect. The lower surfactant concentrations studied showed an inferior relationship between the amount of xenobiotic applied and uptake. High molecular mass surfactants also produced much lower uptake than expected from the dose uptake equations in specific situations.     

Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: chemistry and biology of the cereal herbicide pinoxaden

BACKGROUND: Pinoxaden is a new cereal herbicide that provides outstanding levels of post‐emergence activity against a broad spectrum of grass weed species for worldwide selective use in both wheat and barley. RESULTS: Factors influencing activity and tolerance to pinoxaden were in part linked to distinct structural parts of the active ingredient. Three complementary contributions that decisively impact upon the herbicidal potency against grasses were identified: a preferred 2,6‐diethyl‐4‐methyl aromatic substitution pattern, a dione area suitable for proherbicide formation and beneficial adjuvant effects. The uptake and translocation pattern of pinoxaden when coapplied with its tailored adjuvant were analysed by autoradiography, indicating extensive and rapid penetration, followed by effective distribution throughout the plant. Crop injury reduction on incorporation of the [1,4,5]oxadiazepane ring into the aryldione template was reinforced with safener technology. Comparative studies on the behaviour of pinoxaden applied either alone or in combination with the safener cloquintocet‐mexyl demonstrated that addition of the safener resulted in significant enhancement of metabolic degradation in wheat and barley, providing excellent crop tolerance and a substantial selectivity margin without adverse effects on weed control. CONCLUSION: The biological potential of pinoxaden and its active principle pinoxaden dione in terms of grass weed control and tolerance in cereals was fully exploited by inclusion of the safener cloquintocet‐mexyl in the formulation in combination with a specific and tailor‐made tank‐mix adjuvant based on methylated rape seed oil. Copyright © 2011 Society of Chemical Industry