Hordenine is responsible for plant defense response through jasmonate-dependent defense pathway

Organic agriculture does not rely on synthetic chemical fungicides. An alternative pest management strategy to chemical fungicides is the use of bioactive natural compounds. Hordenine [4-(2-dimethylaminoethyl)] is a phenethylamine alkaloid found in barley. Although hordenine has various pharmacological effects, including antibiotic activity against microorganisms, no studies have been carried out to investigate the inhibitory effects of hordenine on phytopathogenic fungal infection in host plants. Both grape downy mildew and strawberry anthracnose were suppressed by hordenine treatment. Hordenine had no effect on mycelial growth of phytopathogenic fungi, whereas plant defense response through the jasmonate-dependent defense pathway was enhanced in hordenine-treated plants. The concern over environmental pollution has led to the introduction of new pesticides, including bioactive natural compound based pesticide. Hordenine may be used in organic agriculture as an innovative elicitor of plant defense response to downy mildew and anthracnose.     

Synthesis of 1,2,4-triazole compounds related to the fungicides flutriafol and hexaconazole

Triazole and imidazole compounds are important both as pharmaceutical and agrochemical fungicides. It has been demonstrated that they exhibit this activity because they inhibit the 14 α-demethylase enzyme involved in the biosynthesis of fungal sterols. A knowledge of the mode of action of the triazoles paclobutrazol, diclobutrazol and propiconazole has made it possible to devise inhibitors of the 14 α-demethylase enzyme somewhat more readily, using computer graphic techniques. These techniques were used in the discovery of flutriafol, one of the first examples of a triazole tertiary alcohol structure. They also assisted in identifying other triazole tertiary alcohol structures for testing as fungicides. Hexaconazole is one example of a highly active broad-spectrum fungicide. Modification of the hexaconazole structure has produced many other active fungicides, many of which can be conveniently synthesised by the addition of organometallic (e.g. lithium, magnesium, aluminium, titanium or zinc) reagents to α-1,2,4-triazol-1-yl ketones or α-haloketones. Alternatively, they can be prepared by the reaction of nucleophiles such as mercaptans, nitrogen heterocycles or organometallic (e.g. magnesium) reagents with epoxides.     

杀菌剂、除草剂和杀虫剂的先导筛选规则

为了寻找适合于农药的先导筛选规则,对242个杀菌剂、512个除草剂和399个杀虫剂的5个描述符: 疏水常数(LogP)、相对分子质量(MW)、氢键给体数(NHD)、氢键受体数(NHA)、分子极性表面积(PSA)和毒性进行了计算和分析,提出了杀菌剂、除草剂和杀虫剂先导化合物的筛选规则。测试结果显示:杀菌剂、除草剂和杀虫剂的先导筛选规则总体正确率分别为73.3%、 53.3%和63.3%。     

Synthesis and in-vitro antifungal activity of 6-trifluoromethyipyrazolo[3,4-6d]pyrimidin-4(5H)-thiones

Twelve 6-trifluoromethylpyrazolo[3,4-d]pyrimidin-4(5H)-thiones were prepared by the reaction between 4-thiocarbamoyl-5-aminopyrazoles and trifluoroacetic anhydride. They were tested in vitro for antifungal activity against a series of phytopathogenic fungi of different taxonomic classes. The EC50 and MIC values of four compounds were comparable or inferior to those of reference commercial fungicides in controlling Sclerotinia minor, Corticium solani and Phytium ultimum.     

植物挥发性有机化合物在农业病害防控中的潜能与应用

植物病害对全球粮食安全造成严重威胁，而病原物对杀菌剂日益严重的抗药性问题和杀菌剂施用导致的环境暴露风险极大限制了传统杀菌剂的开发。植物释放大量挥发性有机化合物 (volatile organic compounds, VOCs) 到大气中作为植物与周围环境交流互动的信号分子。植物VOCs可以保护自身免受食草动物的侵害，或吸引传粉者和种子传播者，它们还能够直接抑制病原菌的生长或者激活植物的防御系统。本文综述了植物VOCs在生物合成、收集分析、诱导释放、对病原微生物的活性和诱导植物免疫反应等方面的研究进展；总结了典型绿叶挥发物反-2-己烯醛的抑菌和抗性诱导机理；归纳和展望了植物VOCs在田间应用的局限性和今后的研究方向，可为该类化合物在可持续病害防控中的应用提供帮助。     

用于虫生真菌遗传转化的苯菌灵抗性菌株筛选

发展虫生真菌的抗药性是协调生防与化防,稳定真菌杀虫剂应用效果的一个重要策略。本研究从代表性地区采集植物病原样本,分离得到35株菌株,鉴定为3属5种,即灰葡萄孢霉Botrytis cinerea、扩展青霉Penicillium expansum、指状青霉Penicillium digitatum、长柄链格孢菌Alternaria longipes和茄链格孢菌Alternaria solani。应用菌落直径法测定其对苯菌灵的抗性,结果表明：供试的11株灰葡萄孢霉菌株中,最高EC50为936.2670μg·mL^-1;12株青霉属菌株中,最高EC50为0.0384μg·mL^-1;12株链格孢菌株中,最高EC50为703.5557μg·mL^-1。其中灰霉和链格孢属菌株中有4株EC50大于600μg·mL^-1的高抗菌株,即灰葡萄孢霉的菌株SD2和SD1以及茄链格孢的菌株CC2-2和LF1-2,这4株菌株可作为遗传转化抗性基因克隆的基础材料。     

N-(2-三氟甲基-4-氯苯基)-2-吡唑酰氨基环己烷基磺酰胺类化合物的合成与杀菌活性

吡唑酰胺类杀菌剂是近年新农药开发的热点。本研究采用EDCI/HOBt酰胺化法合成了14个结构新颖的N-(2-三氟甲基-4-氯苯基)-2-吡唑酰氨基环己烷基磺酰胺类化合物 ( 3a ~ 3n ),其结构均经1H NMR、13C NMR、质谱和元素分析确认,并用X-射线衍射法确定了化合物 3g 的单晶结构和立体构型。菌丝生长速率法试验结果表明,化合物 3a 、 3e 和 3j 对番茄灰霉病菌Botrytis cinerea KZ-9的EC₅₀值分别为4.28、10.08和11.31 mg/L,抑菌活性不及对照药剂啶酰菌胺和腐霉利;但在孢子萌发试验中,目标化合物表现出与对照药剂相近的抑菌活性,在10 mg/L下有7个化合物对灰霉病菌孢子萌发的抑制率超过了85%;在番茄活体盆栽试验中,化合物 3e 在200 mg/L下对番茄叶片及其花上灰霉病菌的防治效果分别为77.5%和65.2%,高于对照药剂啶酰菌胺 (防效分别为59.8%和30.3%),有进一步研究的价值。     

禾谷镰刀菌中硝基单加氧酶的功能分析

硝基单加氧酶(nitronate monooxygenase, NMO)将硝基烷烃氧化成相应的羰基化合物和亚硝酸盐。尽管硝基单加氧酶的生化特性在少数真菌中得到了深入解析,但是在植物病原真菌中关于其生物学功能的报道很少。本研究通过同源比对,在禾谷镰刀菌(Fusarium graminearium)中鉴定到了5个硝基单加氧酶,利用基因敲除获得了相应的单敲突变体。通过表型分析发现,基因缺失突变体ΔFgNMO1-5的生长速率、菌落形态以及致病力与野生型相比均未发生明显变化,说明硝基单加氧酶之间存在部分功能冗余。突变体ΔFgNMO1、ΔFgNMO4和ΔFgNMO5的分生孢子产量降低了约50%。通过融合绿色荧光蛋白进行功能回补发现,禾谷镰刀菌中这5个硝基单加氧酶在细胞内发挥催化功能的场所存在差异。     

Volatile metabolite profiling to detect and discriminate stem-end rot and anthracnose diseases of mango fruits

The volatile metabolites from the headspace gas of containerised mango ( Mangifera indica ) cv. Tommy Atkins fruits, surface wounded and inoculated with the two fungal anamorphic pathogens Colletotrichum gloeosporioides and Lasiodiplodia theobromae , or non-inoculated (controls), were profiled using a portable gas chromatograph/mass spectrometer to discriminate diseases of mango. Thirty-four compounds were detected relatively consistently among replicates. Several of these were disease/inoculation-discriminatory and were classified into three groups: (i) compounds unique to only one treatment; (ii) compounds common to two or more treatments, but not to all; and (iii) compounds common to all treatments, but varying in their abundance. Two compounds, 1-pentanol and ethyl boronate, were detected in L. theobromae- inoculated mangoes alone, while thujol was observed only in C. gloeosporioides- inoculated mangoes. Discriminant analysis models based on the abundance of significant mass ions and consistent compounds correctly classified diseases/inoculations in up to 100% of cases. The disease-discriminatory compounds and discriminant analysis models developed here have the potential to be used in the early detection of postharvest diseases of mango fruits after validation under commercial conditions.     

禾谷镰刀菌中硝基单加氧酶的功能分析

 硝基单加氧酶(nitronate monooxygenase, NMO)将硝基烷烃氧化成相应的羰基化合物和亚硝酸盐。尽管硝基单加氧酶的生化特性在少数真菌中得到了深入解析,但是在植物病原真菌中关于其生物学功能的报道很少。本研究通过同源比对,在禾谷镰刀菌(Fusarium graminearium)中鉴定到了5个硝基单加氧酶,利用基因敲除获得了相应的单敲突变体。通过表型分析发现,基因缺失突变体ΔFgNMO1-5的生长速率、菌落形态以及致病力与野生型相比均未发生明显变化,说明硝基单加氧酶之间存在部分功能冗余。突变体ΔFgNMO1、ΔFgNMO4和ΔFgNMO5的分生孢子产量降低了约50%。通过融合绿色荧光蛋白进行功能回补发现,禾谷镰刀菌中这5个硝基单加氧酶在细胞内发挥催化功能的场所存在差异。     

Recent Developments in the Mode of Action of Fungicides

This review considers the effect of various fungicides, especially synthetic strobilurins, on fungal respiration, discusses recent contributions of biochemistry to the anilinopyrimidines and the phenylpyrroles and also discusses the future development of chemical inducers of systemic acquired resistance in host plants.     

REMI (Restriction Enzyme Mediated Integration) and its Impact on the Isolation of Pathogenicity Genes in Fungi Attacking Plants

Development of molecular techniques for phytopathogenic fungi aims at the identification of fungal genes whose products are essential for successful infection of the host plant. Initial approaches have relied on isolating candidate genes and generating null-mutations by homologous recombination. Unfortunately, the results of this strategy have not been overly successful. This has led to a search for alternatives which allow an unbiased identification of pathogenicity genes. One method, which has proved successful in several systems, is a tagging mutagenesis procedure termed restriction enzyme mediated integration (REMI). In this mini-review we describe this procedure and review its features and results of its use when applied to the identification of fungal genes required for disease development in planta.     

A comparison of the potency of some fungicides as inhibitors of sterol 14-demethylation

An enzymatic assay system has been developed to measure the relative potency of fungicides such as triadimefon, triarimol, triforine, and buthiobate as inhibitors of sterol 14-demethylation. The enzyme preparation used is the 8000g supernatant derived from a homogenate of an aerobically adapted, anaerobically grown, high sterol strain of Saccharomyces cerevisiae. After incubation of the enzyme with [2-¹⁴C]mevalonic acid and the fungicide the ratio, radioactivity in 4,4-dimethyl sterols/radioactivity in 4-demethyl sterols is determined. The higher this ratio is, the more efficient is the fungicide as an inhibitor of fungal sterol 14-demethylation. The ratio has been determined for a number of commercial fungicides and two series of triazole compounds. A similar assay system based on the 10,000g supernatant from a rat liver homogenate was also tested but gave an inaccurate assessment of the relative potency of fungicides as inhibitors of fungal sterol 14-demethylation.     

Neural networks that distinguish infection periods of wheat tan spot in an outdoor environment

ABSTRACT Tan spot of wheat, caused by Pyrenophora tritici-repentis, provided a model system for testing disease forecasts based on an artificial neural network. Infection periods for P. tritici-repentis on susceptible wheat cultivars were identified from a bioassay system that correlated tan spot incidence with crop growth stage and 24-h summaries of environmental data, including temperature, relative humidity, wind speed, wind direction, solar radiation, precipitation, and flat-plate resistance-type wetness sensors. The resulting data set consisted of 97 discrete periods, of which 32 were reserved for validation analysis. Neural networks with zero to nine processing elements were evaluated 20 times each to identify the model that most accurately predicted an infection event. The 200 models averaged 74 to 77% accuracy, depending on the number of processing elements and random initialization of coefficients. The most accurate model had five processing elements and correctly predicted 87% of the infection periods in the validation set. In comparison, stepwise logistic regression correctly predicted 69% of the validation cases, and multivariate discriminant analysis distinguished 50% of the validation cases. When wetness-sensor inputs were withheld from the models, both the neural network and logistic regression models declined 6% in prediction accuracy. Thus, neural networks were more accurate than statistical procedures, both with and without wetness-sensor inputs. These results demonstrate the applicability of neural networks to plant disease forecasting.     

Effects of the aqueous extracts of Zygophyllum fabago on the growth of Fusarium oxyosporum f. sp. melonis and Pythium aphanidermatum

In this study, the effects of aqueous extracts from Zygophyllum fabago L. on two plant phytopathogenic fungal species (namely, Fusarium oxyosporum f. sp. melonis and Pythium aphanidermatum) were studied under laboratory conditions. The plant extracts (10% w/v) were prepared by using deionized water and fresh tissues. Dilutions (2, 4, 6, and 8% w/v) were obtained to test their effect on the mycelial growth of the phytopathogenic species. Additionally, the recovery of the fungi after their exposure to the Z. fabago extract was analyzed. The plant extracts inhibited the growth of F. oxyosporum and P. aphanidermatum (the maximum mean inhibition that was recorded with the 10% w/v extracts was 42.9% and 85.3%, respectively). A second series of experiments demonstrated the existence of residual effects in both species. The amount of residual inhibition by the 10% w/v extracts was 28.6% in F. oxyosporum and 53.8% in P. aphanidermatum. A dose–response was clearly observed in P. aphanidermatum, while an increase in extract concentration was not associated with a significantly greater reduction in the growth of F. oxyosporum. These findings give insights into the potential of Z. fabago as a growth inhibitor of F. oxyosporum and P. aphanidermatum, thus suggesting an interesting potential role for this common weed as a source of natural fungicides.     

Seed treatments to control seedborne fungal pathogens of vegetable crops

Vegetable crops are frequently infected by fungal pathogens, which can include seedborne fungi. In such cases, the pathogen is already present within or on the seed surface, and can thus cause seed rot and seedling damping‐off. Treatment of vegetable seeds has been shown to prevent plant disease epidemics caused by seedborne fungal pathogens. Furthermore, seed treatments can be useful in reducing the amounts of pesticides required to manage a disease, because effective seed treatments can eliminate the need for foliar application of fungicides later in the season. Although the application of fungicides is almost always effective, their non‐target environmental impact and the development of pathogen resistance have led to the search for alternative methods, especially in the past few years. Physical treatments that have already been used in the past and treatments with biopesticides, such as plant extracts, natural compounds and biocontrol agents, have proved to be effective in controlling seedborne pathogens. These have been applied alone or in combination, and they are widely used owing to their broad spectrum in terms of disease control and production yield. In this review, the effectiveness of different seed treatments against the main seedborne pathogens of some important vegetable crops is critically discussed. © 2013 Society of Chemical Industry     

Opportunities for chiral agrochemicals

Chiral compounds account for 25% of all agrochemical compounds used commercially and for 26% of the total value of the world agrochemical market. However, those sold in single isomer form contribute only 7% to the market value despite many potential advantages in terms of regulatory, intellectual property and marketing benefits. Limited access to chiral raw materials and economic synthesis routes are key reasons why single isomers are less common than they might be. The development of more chiral routes will encourage the development of single isomer compounds to capitalise on their advantages.     

Effect of amphotericin B nanodisks on plant fungal diseases

BACKGROUND: The development of water-soluble nanodevices extends the potential use of compounds developed for other purposes (e.g. antifungal drugs or antibiotics) for applications in agriculture. For example, the broad-spectrum, water-insoluble, macrolide polyene antibiotic amphotericin B (AMB) could be used to inhibit phytopathogenic fungi. A new formulation embedding AMB in nanodisks (NDs) enhances antibiotic solubility and confers protection against environmental damage. In the present study, AMB-NDs were tested for efficacy against several phytopathogenic fungi in vitro and on infected living plants (chickpea and wheat). RESULTS: Compared with AMB in dimethylsulfoxide (DMSO), AMB-NDs increased the sensitivity of several fungal species to this antimycotic in vitro. Sensitivity varied with fungal species as well as with the forma specialis. Phytophthora cinnamomi, previously reported as insensitive to other polyene antimycotics, remained unaffected at the doses examined. Some effect against disease symptoms were obtained with AMB-NDs against fusarium wilt in chickpea, whereas the results were highly variable in wheat, depending on both the species and treatment regimen. CONCLUSION: The results confirm that formulation of AMB into ND increases its effectiveness against phytopathogenic fungi in vitro, opening the possibility for its use on infected plants in the field. Copyright © 2011 Society of Chemical Industry     

基于判别分析的玉米茎腐病发生程度预测模型

对河南省夏玉米区2003年-2018年玉米茎腐病发生、流行情况进行分析,选择制约茎腐病发生流行的主要气象因素,采用判别分析法建立茎腐病发生的两阶段预测模型。应用2003年-2014年的数据进行模型训练,利用2015年-2018年数据进行测试。结果表明,第一阶段预测模型历史回代自身验证准确率为86%,交互验证准确率为79.1%;第二阶段自身验证准确率为83.7%,交互验证准确率为76.7%。应用2015年-2018年数据进行测试,第一阶段预测准确率75%,第二阶段预测准确率85%。说明利用判别分析建立玉米茎腐病流行模型是可行的。     

Distribution of the Consensus Sequences of ABC Transporter Gene among Several Taxonomically Distinct Phytopathogenic Fungi

The distribution of ABC (ATP-binding cassette) transporter genes among several taxonomically distinct phytopathogenic fungi was investigated by Southern blot hybridization, polymerase chain reaction assays and partial sequencing. Consensus sequences of the ABC transporter gene, which might be concerned with multidrug resistance against fungicides and with pathogenicity in phytopathogenic fungi, were found in all of the examined phytopathogenic fungi, which belonged to the Mastigomycotina, Ascomycotina, Basidiomycotina and Deuteromycotina. Received 24 August 2000/ Accepted in revised form 5 December 2000