Perspective: root exudation of herbicides as a novel mode of herbicide resistance in weeds

The evolution of resistance to herbicides in weeds has become a great challenge for global agricultural production. Weeds have evolved resistance to herbicides through many different physiological mechanisms. Some weed species are known to secrete herbicide molecules from roots into the rhizosphere upon being treated. However, root exudation of herbicides as a mechanism of resistance has only recently been identified in two weed species. Root exudation pathways have been investigated in Arabidopsis, and this work suggested that ATP‐binding cassette (ABC) and multidrug and toxic compound extrusion (MATE) transporters play a role in the secretion of primary and secondary plant products from roots. We hypothesize that the mechanisms involved in root exudation of herbicides that result in resistance are mediated by overactive or overexpressed transporters, probably similar to those found for the exudation of primary and secondary compounds from roots. Elucidating the molecular and physiological basis of root exudation in herbicide‐resistant weeds would improve our understanding of the pathways involved in herbicide root secretion mediated by transporters in plants. © 2020 Society of Chemical Industry     

杂草对9类常用不同作用机制除草剂的非靶标抗性机制研究进展

除草剂的应用为农业生产带来便利, 但长期、单一使用某一种或相同机制的除草剂也引发了杂草对除草剂的抗性问题。抗性杂草种类逐渐增加, 抗性形成机制复杂, 导致农田杂草的治理难度增加。杂草对除草剂的抗性机制主要分为两种, 一种是除草剂靶标位点基因的突变或过量表达导致的靶标抗性, 另一种是杂草对除草剂吸收、转运、固存和代谢等一个或多个生理过程发生变化导致的非靶标抗性。本文综述了杂草对9类不同作用方式除草剂的非靶标抗性机制的生理、生化和分子基础的研究进展, 以期为抗性杂草综合治理提供参考。     

Phytotoxic sites of action for molecular design of modern herbicides (Part 1): The photosynthetic electron transport system

A bird's eye review was tried to select the bio‐rational targets from known and novel plant‐specific ones for the molecular design of modern herbicides, which exhibit efficient phytotoxicity at a low‐use rate and preserve a good environment in the 21st century. In phytotoxic sites in the photosynthetic electron transport (PET) system discussed in the present article (Part 1), the generally called bleaching herbicides interfering with the biosynthesis of photosynthetic pigments, chlorophylls and carotenoids, and the biosynthesis of plastoquinone, were considered to be good models for the molecular design of modern herbicides. The PET itself was still considered as an interesting target site for new herbicides, although they need to exert their action in all green leaves of weeds to achieve herbicidal efficacy. Because these herbicides never form a tight binding with D1‐protein, their use‐rate cannot be expected to be as low as the herbicides inhibiting chlorophyll or branched amino‐acid biosynthesis. Other herbicidal targets found in chloroplasts, namely ATP and NADPH formations, have already been omitted from the worldwide biorational molecular design program of herbicides targeting the PET system.     

Evaluation of novel sulfonylurea derivatives with a fused heterocyclic moiety as paddy herbicides that control sulfonylurea‐resistant weeds

Herbicidal activity and acetolactate synthase (ALS) inhibition of sulfonylurea derivatives with a fused heterocyclic moiety bonded to a sulfonyl group were investigated. Some compounds that had an imidazo[1,2‐b]pyridazine moiety substituted at the 2‐position by chlorine or methyl controlled sulfonylurea‐resistant (SU‐R) weeds and showed inhibitory activity to ALS prepared from SU‐R Schoenoplectus juncoides shoot. There was a correlation between in vitro and whole‐plant herbicidal activity of the compounds mentioned above against SU‐R Schoenoplectus juncoides. Among them 1‐(2‐chloro‐6‐propylimidazo[1,2‐b]pyridazin‐3‐ylsulfonyl)‐3‐(4,6‐dimethoxypyrimidin‐2‐yl)urea, propyrisulfuron, was selected for further evaluation. Propyrisulfuron effectively controlled paddy weeds at doses of 70 and 140 g a.i. ha^?1 with good rice selectivity in a field trial.     

Application of bispyribac‐sodium provides effective weed control in direct‐planted rice on a sandy loam soil

An increasing water crisis, as well as the unavailability and high cost of labor, in Pakistan has forced rice‐growers to plant rice directly into the field. However, severe weed infestation causes disastrous effects on the productivity of this rice system. In this study, three herbicides (pendimethalin, penoxsulam and bispyribac‐sodium) were evaluated for weed control in direct‐planted rice on a sandy loam soil. Weedy check and weed‐free plots were established for comparison. Weed infestation decreased the rice yield by 75.2%. However, the application of herbicides suppressed the weed infestation, with a simultaneous increase in the rice yield. The postemergence application of bispyribac‐sodium was the most effective herbicide in reducing the total weed density and dry weight over the weedy check, followed by penoxsulam and pendimethalin, respectively. Bispyribac‐sodium increased the number of productive tillers, 1000‐grain weight, number of grains per panicle and grain yield over the control, as well as improved the water productivity and economic returns of direct‐planted rice. The weeds' proliferation increased the number of unproductive tillers and decreased the plant height. In conclusion, the postemergence application of bispyribac‐sodium can be used effectively to control weeds, increase water productivity and improve the economic returns and yield of direct‐planted rice on a sandy loam soil in Pakistan.     

新型茉莉酸类植物生长调节剂的QSAR研究

应用 Cerius2 软件中的遗传函数算法(GFA)和分子力场分析方法(MFA)对18个新型茉莉酸类化合物具有的对大麦和番茄的生物活性进行定量构效关系(QSAR)研究,所建模型都通过了显著性检验,交叉验证系数r2CV均大于0.810,表明模型都具有良好的预测可靠性。计算研究表明: 分子的热力学性质 (各种原子类型 AlogP 描述符)、空间结构状态(Jurs-RPSA参数)、 电性描述符(Dipole-mag 和 HOMO)和结构描述符(Hond Acceptor)是影响活性的主要二维因素。用三维QSAR方法研究了茉莉酸类化合物与其受体有效相互作用时所需的理化特征,并进一步验证了二维QSAR模型的可靠性。该研究可为进一步了解茉莉酸类化合物在植物体内的信号传导机制和研制具有生态农药性质的茉莉酸类植物生长调节剂提供理论指导。     

Synthesis and herbicidal activity of new oxazinone herbicides with a long-lasting herbicidal activity against Echinochloa oryzicola

Chemical modification of the herbicide 1-[2-(benzothiazol-2-yl)isopropyl]-4-methyl-3-phenyl-5H-pyrrolin-2-one (MI-2826) has revealed a new oxazinone herbicide, 3-[2-(7-chlorobenzothiazol-2-yl)isopropyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (MI-3069), for use in paddy fields. In comparing the phyototoxicity of the two herbicides to transplanted rice, the latter was superior to the former and kept the same predominant characteristic to control Echinochloa oryzicola Vasin for a long period of time owing to its long-lasting residual effect.     

The herbicide flamprop-M-methyl has a new antimicrotubule mechanism of action

BACKGROUND: The herbicidal mode of action of flamprop‐M‐methyl [methyl N‐benzoyl‐N‐(3‐chloro‐4‐fluorophenyl)‐D ‐alaninate] was investigated. RESULTS: For initial characterization, a series of bioassays was used, which indicated a mode of action similar to that of mitotic disrupter herbicides. Cytochemical fluorescence studies, which included monoclonal antibodies against polymerized tubulin, were applied to elucidate effects on mitosis and microtubule assembly in maize roots. When seedlings were root treated with 50 µM of flamprop‐M‐methyl, cell division activity in meristematic root tip cells ceased within 4 h. The compound severely disturbed the orientation of spindle and phragmoblast microtubules, leading to defective spindle and phragmoblast structures. Cortical microtubules were only slightly affected. In late anaphase and early telophase cells, phragmoblast microtubules were disorganized in multiple arrays that hampered regular cell plate deposition in cytokinesis. Microtubules of the spindle apparatus were found attached to chromosomal kinetochores, but did not show regular organization associated with a zone of microtubule‐organizing centres at the opposite ends of the cell. On account of this loss of spindle organization, chromosomes remained in a condensed state of prometaphase or metaphase. Unlike known microtubule disrupter herbicides, flamprop‐M‐methyl and its biologically active metabolite flamprop did not inhibit soybean tubulin polymerization to microtubules in vitro at 50 µM . In contrast, soybean plants responded sensitively to the compounds. CONCLUSION: The results indicate that flamprop‐M‐methyl is a mitotic disrupter herbicide with a new antimicrotubule mechanism of action that affects orientation of spindle and phragmoblast microtubules, possibly by minus‐end microtubule disassembly. Copyright © 2008 Society of Chemical Industry     

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. © 2001 Society of Chemical Industry     

Novel 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2] benzopyran derivatives: synthesis of chiral glycol benzyl ether herbicides

Novel tricyclic 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran (TFB) derivatives were synthesized, and their herbicidal activities were elucidated. They were synthesized from D-glucose as a natural chiral source. The formation of the TFB skeleton was achieved by a Friedel-Crafts type intramolecular cyclization of methyl 5-deoxy-2,3-O-dibenzyl-5-C-methyl-D-xylofranosides. The intramolecular cyclization was dependent upon the electronic effects of the substituents at the C-2 benzyloxy group of methyl xylofranosides. Some TFBs exhibited a remarkable herbicidal activity to annual paddy weeds, such as Echinochloa sp, without injury to the rice.     

Recent developments in our understanding of the plant cuticle as a barrier to the foliar uptake of pesticides†

The plant cuticle is a highly complex membrane which forms the outer surface of the aerial portion of plants. The nature of the plant cuticle is reviewed with particular regard to its action as a potential barrier to the penetration of pesticide molecules; the role of the cuticular waxes is highlighted. The physicochemical properties of the cuticle influence the behaviour of spray droplets and, in turn, may affect the rate and efficiency of cuticle penetration. The permeation of active ingredients is influenced by their solubility characteristics as indicated by octanol/water (log K_ow) and cuticle/water (K_cw) partition coefficients. Penetration of hydrophilic compounds (low log K_ow) may be enhanced by hydration of the cuticle, while transcuticular transport of non-polar solutes (high log K_ow) is increased by factors which reduce wax viscosity. The use of in-vitro models involving isolated cuticle membranes, isolated cuticle waxes, or isolated leaves has helped to focus on the activities of the cuticle in the absence of other physiological factors. Using these systems, the role of the waxes as a transport-limiting barrier has been identified and the factors influencing sorption, permeance and desorption examined. The action of surfactants, in vitro and in vivo, has been briefly addressed in regard to their role in facilitating cuticle penetration; other steps involving surfactant/solute/cuticle are complex, and synergy appears to depend on a number of factors including test species, concentration of active ingredient, surfactant type and concentration. Adjuvants may greatly influence the surface properties of the droplet, predispose the cuticle to solute transport, and enhance pesticide activity. The nature of these complex inter-relationships is discussed. © 1999 Society of Chemical Industry     

Persistence of <Emphasis Type="Italic">Xanthomonas axonopodis</Emphasis> pv. <Emphasis Type="Italic">vignicola</Emphasis> in weeds and crop debris and identification of <Emphasis Type="Italic">Sphenostylis stenocarpa</Emphasis> as a potential new host

The survival of Xanthomonas axonopodis pv. vignicola, incitant of cowpea bacterial blight and pustule, in residues of infested cowpea leaves was studied in the field in the forest savanna transition zone of South Benin and under variable controlled conditions. The pathogen survived for up to 60 days when placed on the soil surface, and up to 45 days buried at depths of 10 and 20 cm. In the glasshouse, bacteria survived in residue mixed with soil for at least 2 months in dry soil and less than 2 months in moist soil. The pathogen survived at least 30 days in the field after spray-inoculation on the weed species Euphorbia heterophylla, Digitaria horizontalis and Synedrella nodiflora; 20 days on Panicum subalbidum; 10 days on Euphorbia hirta; and 5 days on Talinum triangulare. After leaf-infiltration under glasshouse conditions, the pathogen was detected after 90 days in D. horizontalis; 75 days in T. triangulare, P. subalbidum and S. nodiflora; 60 days in E. hirta, and 30 days in E. heterophylla. Among 12 legume species tested as alternative hosts of X. axonopodis pv. vignicola, only Sphenostylis stenocarpa (African yam bean) showed typical symptoms of cowpea bacterial blight in a glasshouse experiment following artificial inoculation. This is the first time this legume species has been identified as a potential host of X. axonopodis pv.vignicola. Crop residue and weeds are likely sources of primary inoculum when planting two consecutive cowpea crops per year and they probably play a role in dissemination of the pathogen during the cropping season. The alternate host may form a bridge for primary inoculum between cropping seasons.     

基于超高效液相色谱-高分辨质谱快速筛查绿茶中12种植物生长调节剂的方法研究

建立了超高效液相色谱-高分辨质谱（ultra performance liquid chromatography-high resolution mass spectrometry,UPLC-HRMS）快速筛查绿茶中2,4-滴、对氯苯氧乙酸、吲哚丁酸、氯吡脲和吲哚乙酸等12种植物生长调节剂的方法。采用CAPCELL PKA-C18色谱柱（100 mm×2.1 mm,2 μm）,正离子模式下以体积分数为5%的甲醇水溶液（含有5 mmol/L乙酸铵和体积分数为0.1%甲酸）为流动相;负离子模式下以体积分数为5%甲醇水为流动相,梯度洗脱。在全扫描采集模式下,基于化合物的保留时间、准分子离子峰的精确质量数、碎片离子的精确质量数和同位素分布匹配指数,对目标物进行筛查分析。结果表明:12种植物生长调节剂在绿茶中的报告限（RL）为0.01 mg/kg;在0.01、0.1和0.5 mg/kg 3个添加水平下,其回收率在61%~130%之间,相对标准偏差在1.8%~17%之间。该方法简便快捷,可用于绿茶中常用植物生长调节剂的筛查。     

Serendipitous identification of a new Iflavirus‐like virus infecting tomato and its subsequent characterization

The genomic sequence of a previously undescribed virus was identified from symptomless tomato plants (Solanum lycopersicum). The viral genome is a positive‐sense ssRNA molecule of 8506 nucleotides. It is predicted to encode a single polyprotein of 314·5 kDa that is subsequently processed into three coat protein components of 13·7, 17·9 and 13·5 kDa, and a viral replicase of approximately 207 kDa with conserved motifs for a helicase, a protease and RNA‐dependent RNA polymerase (RdRp). Pairwise analysis of the deduced amino acid sequence of the RdRp revealed that it shares closest identity with members of the family Iflaviridae, genus Iflavirus (19–47% identity). Evidence of replication in plants was detected by RT‐PCR of the viral replicative strand, and short interfering RNAs (siRNAs) matching the virus. The name Tomato matilda virus (TMaV) is proposed, and furthermore, that the genus Tomavirus (Tomato matilda virus) be created within the family Iflaviridae. This is the first report of a plant‐infecting virus resembling members of the Iflaviridae.     

Effects of drought on weed emergence and growth vary with the seed burial depth and presence of a cover crop

In conservation agriculture, weed seed germination could decrease with the presence of a cover crop, surface weed seed location and temporal drought in summer just after seed shedding. This study simultaneously examined the effects of a cover crop, burial depth (seed location) and hydric stress on weed emergence and early growth. It was hypothesized that drought would reduce weed emergence and the initial growth of weed seeds and that this effect would be greater when the seeds were on the soil surface and in the presence of a cover crop. Four annual weed species were chosen that are frequently found (Anisantha sterilis, Vulpia myuros, Sonchus asper, Veronica persica) and not frequently found (Alopecurus myosuroides, Poa annua, Cyanus segetum, Capsella bursa‐pastoris) in fields that implement conservation agriculture. The unburied seeds had 26% lower emergence, on average, than the buried seeds (significant for six of the eight species), hydric stress reduced emergence by 20% (for seven of the eight species) and the presence of a cover crop reduced the level of emergence by 17% (for all species). The unburied seeds with hydric stress were emerging under the “most stressful” set of factors, with a 45% decrease in emergence, compared with the seeds emerging under the “least stressful” set of factors (buried seeds without hydric stress). All the weed growth measurements (height, dry matter content and number of leaves) decreased with the presence of a cover crop. The species that are found frequently in the fields that implement conservation agriculture, compared with the species that are not frequently found in conservation agriculture fields, had higher rates of germination and a higher tolerance of hydric stress when their seeds were unburied.