Metabolism of isopropyl carbanilate (propham) in alfalfa grown in nutrient solution

Alfalfa plants, Moapa variety, were grown in nutrient solution containing isopropylring-[¹⁴C] carbanilate (43.8 μCi/liter propham). After 8 days, 41.2% of the radioactivity initially added to the nutrient culture was recovered; 10.9% of this was from shoots, 3.4% from roots and 26.9% from nutrient medium. Nonextracted residues accounted for 23% of the radioactivity in shoots and 62% of that in roots. The parent herbicide constituted 53 and 38% of the radioactivity extracted from shoots and roots, respectively. The balance of extracted ¹⁴C was polar metabolites which were purified and subjected to enzymatic and acid hydrolysis. Four aglycones were isolated, three of which were purified by thin-layer chromatography and characterized by mass spectrometry. The principal aglycones were: isopropyl-2-hydroxycarbanilate, isopropyl-4-hydroxycarbanilate, and 1-hydroxy-2-propylcarbanilate. The fourth aglycone was not identified.     

Animal metabolism of propham (isopropyl carbanilate): The fate of residues in alfalfa when consumed by the rat and sheep

Alfalfa was root-treated with [¹⁴C]propham (isopropyl carbanilate[¹⁴C-phenyl(U)]) for 7 days and then harvested and freeze-dried. Rats and sheep were orally given either ¹⁴C-labeled alfalfa roots ([¹⁴C]root) or ¹⁴C-labeled alfalfa shoots ([¹⁴C]shoot). When the [¹⁴C]root was given, 6.5–11.0% of the ¹⁴C was excreted in the urine and 84.6–89.4% was excreted in the feces within 96 h after treatment. Less than 3% of the ¹⁴C remained in the carcass (total body—gastrointestinal tract and contents) 96 h after treatment. When [¹⁴C]shoot was given, 53.2–55.2% of the ¹⁴C was excreted in the urine, 32.1–43.4% was excreted in the feces, and the carcass contained 0.2–1.1% of the ¹⁴C 96 h after treatment. When the insoluble fraction (not extracted by a mixture of CHCl₃, CH₃OH, and H₂O) of both alfalfa roots and shoots was fed to rats, more than 86% of the ¹⁴C was excreted in the feces and less than 3% remained in the carcass 96 h after treatment. The major radiolabeled metabolites in the urine of the sheep fed ¹⁴C shoot were purified by chromatography and identified as the sulfate ester and the glucuronic acid conjugates of isopropyl 4-hydroxycarbanilate. Metabolites in the urine of the sheep treated with [¹⁴C]root were tentatively identified as conjugated forms of isopropyl 4-hydroxycarbanilate, isopropyl 2-hydroxycarbanilate, and 4-hydroxyaniline. The combined urine of rats dosed with [¹⁴C]shoot and [¹⁴C]root contained metabolites tentatively identified as conjugated forms of isopropyl 4-hydroxycarbanilate, isopropyl 2-hydroxycarbanilate, and 4-hydroxyaniline.     

Nitric oxide reduces oxidative stress generated by lactofen in soybean plants

Nitric oxide (NO) is a molecule able to directly scavenge ROS and end chain reactions, which can be generated by some herbicides. This study aimed to evaluate whether the pretreatment of soybean plants with sodium nitroprusside (SNP) solution, a NO-donor substance, provides protection against oxidative stress generated by lactofen. Soybean plants were pretreated with SNP before lactofen application. The levels of lipoperoxides and photosynthetic pigments were quantified, and the activity of the antioxidant enzymes glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD) was assessed. Although lipid peroxidation was not completely prevented, NO was able to scavenge ROS generated by the lactofen action, avoiding the photosynthetic pigment breakdown. Consequently, ROS scavenging by NO leads to a decrease in the available substrate for the antioxidant enzymes SOD, CAT, and POD, which are essential to protect plants under oxidative stress situations such as absence of GST induction by H₂O₂.     

Metabolism of bifenox in soil and plants

The herbicide, methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (bifenox), had a half-life of 3 to 7 days after preemergence application to a greenhouse soil mix. Metabolites identified included: 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, 2,4-dichlorophenyl 4-nitrophenyl ether (nitrofen), and 5-(2,4-dichlorophenoxy)anthranilic acid over a 313-day sampling period. Comparison of the total ¹⁴C in the soil to that extractable by methanol showed an increase in the proportion of bound material. The major metabolite eluted from a Frederick clay loam soil column was identified as the acid of bifenox and its mobility was associated with the short half-life of bifenox in soil. In vitro studies with shoot-tissue macerates showed that bifenox was not degraded by corn (Zea mays L.) or soybeans (Glycine max (L.) Merr.) and was degraded to less than 1% by velvetleaf (Abutilon theophrasti Medic.).     

Metabolism and selectivity of rice herbicides in plants

Chemical weed control with effective and highly active herbicides has been very useful and convenient means. It has contributed to stable crop production and is labor saving. Recent herbicides have had characteristics such as high effectiveness without causing environmental pollution or harmful effects, and appropriate herbicides having high activity, low toxicity, high selectivity and being non-persistent have been developed. The metabolism of rice herbicides used mainly in Japan, such as sulfonylurea, chloroacetamide, acylamide, urea, thiocarbamate, pyrazole, triazine, diphenyl ether, phthalimide, phenoxy, aryloxyphenoxypropionate, etc., is reviewed, and its involvement in selectivity is also discussed. The metabolism of herbicides is closely related to their activity and selectivity. Differential herbicide metabolism in plants is a contributing factor of selectivity between crops and weeds. Chemicals that are more detoxified in crops and/or more activated or less detoxified in weeds are considered as being effective and selective herbicides. The metabolism of various types of rice herbicides includes: oxidative reaction (ring and chain hydroxylation, O - and N -dealkylation), hydrolysis and subsequent glucose conjugation, and glutathione conjugation in rice. These detoxicative activities are much higher in rice than weeds in paddies, and this leads to the selectivity of herbicides. Enzymes, oxidase, P-450 mono-oxygenase, esterase, acylamidase, glucosyl transferase, glutathione transferase, etc., play important roles in herbicide metabolism and selectivity.     

Metabolism of the fungicide triforine in barley plants

The metabolic fate of [³H]-triforine in barley plants has been studied. 15 and 30 days after treatment, unchanged triforine amounted to 57.5 and 43.2% respectively, and of three soluble metabolites detected, piperazine (0.3 and 4.0%) and N-[2, 2,2-trichloro-1-(piperazin-1-yl)ethyl] formamide (12.9 and 8.4%), the latter for the first time as a metabolite in plants, were identified using t.1.c. with four solvent systems. The solid residue contained 23.1 and 38.2% of bound label after 15 and 30 days respectively.     

Metabolism of 2-aminobenzimidazole and benzimidazole in melon plants

Melon plants grown in a liquid nutrient solution were separately treated either with benomyl, 2-aminobenzimidazole (2-AB), or benzimidazole (BZ), and after 60 days each compound had decomposed into significant concentrations of metabolites, those from 2-AB and BZ corresponding to the metabolites from benomyl. This supported the following postulated metabolic pathway for benomyl in melon plants: benomyl → carbendazim → 2-AB→BZ Involvement of the other identified metabolites of benomyl (2-aminobenzonitrile, o-phenylenediamine, aniline, and the conjugates of carbendazim and 2-AB) cannot be proposed unequivocally. In the extracts from plants treated with 2-AB or BZ, new and unidentified metabolites have also been observed using gas-liquid chromatography (g.l.c.).     

Translocation, metabolism and residues of fluazifop-butyl in soybean plants

Translocation of fluazifop-butyl in soybean plants and hydrolysis of the ester to fluazifop-acid were investigated in a field experiment. The herbicide was translocated rapidly from the leaves to the roots, but the concentration in the leaves remained about 10-fold higher than that in the roots. Rapid hydrolysis of fluazifop-butyl to fluazifop-acid was observed, and residues of the metabolite were found to persist much longer in the plant than the active compound. Increased temperatures resulted in more rapid hydrolysis. No traces of active compound or of its main metabolite were found in the seeds after harvest. A reversed-phase HPLC method for simultaneous détérmination of fluazifop-butyl and fluazifop-acid residues in soybean plants was developed. Transport, metabolisme et residus du fluazifop-butyl chez les plantes de soja Le transport du fluazifop-butyl dans les plantes de soja et l'hydrolyse de Tester en fluazifop-acide ont étéétudiés dans une experimentation de plein champ. L'herbicide a été vehiculé rapidement des feuilles vers les racines, mais la concentration dans les feuilles est demeurée 10 fois plus haute que celle dans les racines. Une hydrolyse rapide de la forme ester en acide a été observee, et les residus du metabolite se sont reveles beaucoup plus persistants dans la plante que le composé actif. Une augmentation des températures a accéléré l'hydrolyse. Aucunes traces de la matière active ou de son principal métabolite n'ont été trouvées dans les graines après la récolte. Une methode HPLC en phase inverse pour la détérmination simultanée des residus de fluazifop-butyl et de fluazifop-acide chez le soja a été développée. Translokation, Metabolismus und Ruckstande von Fluazifop-butyl in Sojabohnen-Pflanzen Die Translokation von Fluazifop-butyl in Sojabohnen-Pflanzen und die Hydrolyse des Esters zu Fluazifop-Saure wurden in einem Freilandversuch untersucht. Das Herbizid wurde von den Blattern in die Wurzein schnell transloziert, doch in den Blattern blieb die Konzentration etwa 10mal großer als in den Wurzein. Es wurde eine schnelle Hydrolyse des Fluazifop-butyls zu Fluazifop-Saure beob-achtet, und die Ruckstande des Metaboliten in den Pflanzen erwiesen sich als viel bestandiger als der Wirkstoff. Bei hoheren Temperaturen lief die Hydrolyse schneller ab. In den Samen wurden nach der Ernte keine Ruckstande des Wirkstoffs oder seiner Hauptmetaboliten gefunden. Eine Reversed-Phase-HPLC-Methode zur gleichzeitigen Bestimmung von Ruckstanden von Fluazifop-butyl und Fluazifop-Saure in Sojabohnen-Pflanzen wurde entwickelt.     

Aggressiveness of Xanthomonas axonopodis pv. glycines isolates to soybean and hypersensitivity responses by other plants

Xanthomonas axonopodis pv. glycines ( Xag ) causes bacterial pustule disease which can significantly reduce the production of soybean. A collection of 26 isolates of Xag from different soybean-production areas of Thailand was shown to differ with regard to aggressiveness on soybean. They also differed in their ability to induce a hypersensitive response (HR) on four cultivars of tobacco and on other plant species including pepper, tomato, cucumber, pea and sesame. Tomato was most sensitive to HR induction by Xag . Isolate KU-P-34017 caused an HR on all the plant species tested. The minimal concentration of KU-P-34017 needed to induce HR on tobacco was approximately 5 × 10⁸ CFU mL⁻¹. A bacterium–plant interaction period of at least 2·5 h was necessary for HR, and different temperatures, relative humidity and light periods did not affect HR development. Inhibitors of eukaryotic metabolism, including cobalt chloride, lanthanum chloride and sodium orthovanadate (completely), and cycloheximide (partially) blocked the HR on tobacco, indicating the association of an active plant response. In contrast, the HR on tomato was inhibited only by cobalt chloride.     

Metabolism of N-hydroxymethyl dimethoate and N-desmethyl dimethoate in bean plants

N-Hydroxymethyl [carbonyl-¹⁴C] dimethoate (0.43 ppm) and N-desmethyl [carbonyl-¹⁴C] dimethoate (0.50 ppm) were stem-injected into bean plants (Phaseolus vulgaris) in two separate experiments. Plants were harvested periodically, extracted, fractionated, and analyzed for metabolites. The resulting pattern of metabolites formed from the administration of these two compounds was different. Radioactivity was not detected in the organic fraction 2 days after N-desmethyl dimethoate administration. N-Desmethyl dimethoate was rapidly broken down to dimethoate carboxylic acid and other polar metabolites, then further degraded into materials which became part of the plant constituents. N-Hydroxymethyl dimethoate was quite stable in the plant. Most of the material not remaining as parent became rapidly conjugated and constant levels of conjugate were maintained. Very little radioactivity was bound in the plant marc. The metabolic pathway of these compounds is as follows: N-hydroxymethyl to the glucoside or N-desmethyl derivative; the N-desmethyl metabolite degrades primarily to the carboxylic acid but also to N-desmethyl dimethoxon, either of which in turn may be degraded to dimethoxon carboxylic acid. The conversion of -NHCH₂OH to -NH₂ is a slow reaction so that conjugation becomes the route of choice when the plant is treated with N-hydroxymethyl dimethoate.     

Metabolism of chlorsulfuron by plants: Biological basis for selectivity of a new herbicide for cereals

A major factor responsible for the selectivity of chlorsulfuron [2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide] (formerly DPX-4189), as a postemergence herbicide for small grains is the ability of the crop plants to metabolize the herbicide. Chlorsulfuron is the active ingredient in Du Pont “Glean” weed killer. Tolerant plants such as wheat, oats, and barley rapidly metabolize chlorsulfuron to a polar, inactive product. This metabolite has been characterized as the O-glycoside of chlorsulfuron in which the phenyl ring has undergone hydroxylation followed by conjugation with a carbohydrate moiety. Sensitive broadleaf plants show little or no metabolism of chlorsulfuron.     

Systemic properties of myclobutanil in soybean plants, affecting control of Asian soybean rust (Phakopsora pachyrhizi)

BACKGROUND: The demethylation inhibitor (DMI) fungicide myclobutanil can be an effective component of spray programmes designed to control the highly destructive plant pathogen Phakopsora pachyrhizi Syd. & P. Syd., causal agent of Asian soybean rust. Myclobutanil is known from previous studies in grapevines to be xylem mobile. This study investigates the mobility profile of myclobutanil in soybean as an important component of its effective field performance. RESULTS: Over a 12 day period under greenhouse conditions, a constant uptake of myclobutanil from leaflet surfaces into the leaflet tissue was observed. Once in the leaflet, myclobutanil was seen to redistribute throughout the tissue, although no movement out of leaflets occurred owing to a lack of phloem mobility. The ability of myclobutanil to redistribute over distance within the soybean plant was revealed when visualizing movement of the compound to foliage above the point of application on the plant stem. An efficacy bioassay demonstrated that the systemic properties of myclobutanil allow control of disease at a point remote from the initial site of compound application. CONCLUSION: It is suggested that the high degree of xylem systemicity displayed by myclobutanil in soybean foliage is a contributory factor towards its commercial effectiveness for control of Asian soybean rust. Copyright © 2008 Society of Chemical Industry     

Coinfection of soybean plants with Phytophthora sojae and soybean cyst nematode does not alter the efficacy of resistance genes

The soybean cyst nematode (SCN) Heterodera glycines and the oomycete Phytophthora sojae are among the most damaging pathogens of soybean worldwide. Resistant cultivars are commonly used to manage these diseases. As it is known that the presence of SCN can facilitate the development of other pathogens, it is important to verify if there is a synergistic activity between SCN and P. sojae. The purpose of this study was to evaluate a possible interaction on susceptible and resistant soybean lines. The plants were inoculated with one or both organisms at different stages (5 or 10 days old). Two levels of SCN inoculum (2,000 and 10,000 eggs/plant) and different timing between SCN and P. sojae inoculation (2, 5, or 8 days) were compared. The results on 5-day-old plants showed that SCN did not influence P. sojae development. The resistant cultivar to P. sojae remained effective (0% mortality) and susceptible cultivars exhibited high mortality (100%) in the presence or absence of SCN. Experiments on 10-day-old plants showed that SCN resistance was not affected by the presence of P. sojae. SCN inoculum density and timing of P. sojae infection did not affect the virulence of these pathogens and the efficacy of resistance genes. However, the number of SCN cysts was decreased by more than 50% (p < .001) when P. sojae was coinfesting the susceptible cultivar. This suggests that P. sojae might indirectly influence SCN development by reducing the root mass. This study confirmed that resistant cultivars remain a valid option for the management of P. sojae and SCN.     

Metabolism and cell wall incorporation of phenoxyacetic acid in soybean cell suspension culture

The metabolism of [¹⁴C]phenoxyacetic acid (POA) was studied in cell suspension culture of soybean (Glycine max). POA was metabolized to 4-HO-POA, 4-HO-POA glucoside and 4-HO-POA glycosidic ester. A large part of the 4-HO-POA glucoside and small amounts of the glycosidic ester were recovered in the medium. POA was also converted to non-extractable residues bound to cell walls. Sequential extraction of cell-wall polymers showed that non-extractable residues, partly identified with 4-HO-POA and POA, were mainly associated with hemicelluloses and lignin. Comparison of the metabolism of [carboxy-¹⁴C]- and [phenyl-¹⁴C]POA revealed some degradation of the POA side-chain, followed in all probability by the incorporation of the aromatic moiety into cell walls. However, the sturdiness of the resulting bonds prevented precise identification of these bound aromatic structures. In summary, the degradation of POA in soybean cell culture provided a good model to study the formation of non-extractable residues of pesticides. © 1999 Society of Chemical Industry     

菜豆荚斑驳病毒-危害大豆等豆科植物的重要病毒

大豆原产中国，是我国重要的经济作物，我国大豆产量居世界第4位。近年来，位居大豆产量前三位的美国、巴西和阿根廷对华出口大豆数量不断增加，有害生物随大豆传人风险也在不断加大。菜豆荚斑驳病毒是危害大豆等豆科植物的重要病毒，在美国已引起大豆巨大的产量损失。我国无此病毒的分布。最近，我出入境口岸从进口的美国大豆中多次检出该病毒，它已对我国的大豆生产构成了现实的威胁，若此病毒随进口大豆传人国内，并定殖下来，将会对国内的大豆生产造成不可估量的损失。本文对该病毒的生物学特性，检验和鉴定方法以及重要性进行了介绍，供口岸检疫人员参考。     

Metabolism of [14C]-2,4-dichlorophenol in edible plants

Several 2,4-dichlorophenoxyacetic acid (2,4-D)-sensitive plants have been modified by genetic engineering with tfdA gene to acquire 2,4-D tolerance. The expression product of this gene degrades 2,4-D to 2,4-dichlorophenol (DCP), which is less phytotoxic but could cause a problem of food safety. After a comparison of 2,4-D and DCP metabolism in transgenic 2,4-D-tolerant and wild cotton (Gossypium hirsutum L.), a direct study of DCP metabolism in edible plants was performed. After petiolar uptake of a [U-phenyl-(14)C]-DCP solution followed by a 48 h water chase, aqueous extracts were analysed by high-performance liquid chromatography. Metabolites were thereafter isolated and their structural identities were determined by enzymatic and chemical hydrolyses and mass spectrometry analyses. The metabolic fate of DCP was equivalent to 2,4-D metabolism in transgenic 2,4-D-tolerant cotton. In addition, DCP metabolism was similar in transgenic and wild cotton. The major terminal metabolites were DCP-saccharide conjugates in all species, essentially DCP-(6-O-malonyl)-glucoside or its precursor DCP-glucose. The significance of this metabolic pathway with regard to food safety is discussed.     

Metabolism of [2,5-14c]piperazine in barley plants

The shoots of barley plants root-treated with [2,5-¹⁴C]piperazine were analysed 30 days after treatment. Methanol extraction left a solid residue which contained 31.9% of ¹⁴C (all percentages refer to the total of ¹⁴C incorporated into the shoots); further extraction with acidified methanol and dimethyl sulphoxide dissolved respectively 3.2% and 5.8% of ¹⁴C. The initial methanol extract contained radioactive piperazine (16.8%), iminodiacetic acid (8.6%), glycine (15.4%), oxalic acid (7.2%), and un-identified compounds (20.1%). In barley, piperazine is the product of the most advanced metabolism so far identified of the fungicide triforine, 1,4-bis(2,2,2-trichloro-1-formamidoethyl)piperazine; the results obtained here show that piperazine is certainly not the end-product of the metabolism of triforine in barley.     

磷营养和土壤含水量对大豆光合特性的交互影响

采用盆栽砂培,对不同磷(0.05、0.5、1.02、.0 mmol/L KH2PO4)、水(田间持水量的20%、40%、60%和80%)条件下大豆的光合特性进行了研究。结果表明:(1)低磷和干旱胁迫导致大豆叶片含水量和地上部分生物量显著降低,水分饱和亏缺和根冠比增大。磷营养和土壤含水量对叶片水分饱和亏缺、根冠比、叶片含水量、比叶面积、地上部分生物量具有显著的交互效应。(2)低磷和干旱胁迫显著降低了大豆的叶绿素含量(Chl a、Chl b和Chl a+b),缺磷导致叶绿素a/b比值显著升高,且具有显著的磷×水交互效应。(3)缺磷和干旱胁迫显著降低了Fv/Fm和ΦPSII,并对Fv/Fm具有显著的交互效应。(4)低磷和干旱胁迫下,大豆叶片的净光合速率(Pn)、气孔导度(Gs)、胞间CO2浓度(Ci)和蒸腾速率(E)显著减小,气孔限制值(Ls)增大,磷营养和土壤含水量对水分利用效率(WUE)和Ls的交互效应显著。     

Chloroaniline peroxidation by soybean peroxidases

4-chloroaniline was oxidized by soya cell-wall peroxidases in the presence of hydrogen peroxide. The main product, an orange compound with a maximal absorbance at 455 nm, was probably 4, 4′-dichloroazobenzene. The optimum pH of the reaction was 4. Michaelis constants, determined as described by Dalziel, were 21 mM for 4-chloroaniline and 94 μM for hydrogen peroxide. Syringaldazine was an uncompetitive inhibitor of 4-chloroaniline peroxidation (K_i =46 μM) and modified the progress of the reaction with the appearance of a lag period. By contrast, 4-chloroaniline was a non-competitive inhibitor of syringaldazine peroxidation with a K_i value of 21 mM_x at pH 7.5. Therefore, these two inhibiting effects were compatible with the presence of two binding sites for two different hydrogen donors. Both sites were linked by allosteric interactions. The inferences on chloroaniline binding are discussed.     

大豆凝集素基因lec-s转化烟草>增强对烟草花叶病毒的抗性

 将编码大豆凝集素的lec-s基因插入植物表达载体pBI121中,构建植物重组表达质粒pBI121:: lec-s。由根癌土壤杆菌EHA105介导的叶盘法转化烟草,获得了转基因烟草株系。PCR和RT-PCR检测证明lec-s基因已转入烟草植株中。接种烟草花叶病毒（Tobacco mosaic virus,TMV）进行抗病性试验结果表明,转基因烟草叶片上的病斑数显著减少,说明转基因烟草表现出对TMV的抗性。定量RT-PCR检测发现,接种TMV后,抗病防卫基因（PR-1a、GST1、Pal和hsr515）在转基因烟草叶片中显著上调表达。这些结果表明,大豆凝集素基因lec-s转化烟草可对TMV产生抗性,其作用机制可能在于lec-s基因参与了植物的防卫信号通路,诱导了抗病防卫基因在转基因植株体内的表达,增强了植株对TMV的系统抗性。