Synthesis and herbicidal potential of substituted aurones

BACKGROUND: With the objective of exploring the herbicidal activity of substituted aurones, a series of 4,6‐disubstituted and 4,5,6‐trisubstituted aurones were synthesised, and their herbicidal activities against Brassica campestris L. and Echinochloa crusgalli (L.) Beauv. were evaluated in laboratory bioassays. Effects of some of the compounds were evaluated on seed germination. The most active compounds in the laboratory were evaluated in the greenhouse. RESULTS: The compounds were characterised by ¹H NMR, ¹³C NMR and HRMS; some of them were further identified by IR. A (Z)‐configuration was assigned to the aurones, based on spectroscopic and crystallographic data. Bioassay results of root growth showed that the aurones had a moderate herbicidal activity against the dicotyledonous plant Brassica campestris. (Z)‐2‐Phenylmethylene‐4,6‐dimethoxy‐3(2H)‐benzofuranone(6o) was the most active compound, with 81.3 and 88.5% inhibition at 10 and 100 µg ml^?1 respectively, equal to the activity of mesotrione. Some of the aurones possessed some inhibition of germination on several plant species. For glasshouse tests, the substituted aurones had lower herbicidal activity than metolachlor and mesotrione. CONCLUSION: It is possible that aurone derivatives, which possess structures different from those of the commercial herbicides, may become novel lead compounds for the development of herbicides against dicotyledonous weeds with further structure modification. Copyright © 2012 Society of Chemical Industry     

Effects of certain herbicides on the fate of sporangiospores of Mucor piriformis and conidia of Botrytis cinerea and Penicillium expansum

The effects of several herbicides used in pome fruit orchards on the germination of spores and growth of mycelia of Botrytis cinerea, Mucor piriformis and Penicillium expansum in vitro and the survival of propagules of these fungi in soil were studied. Diuron in agar at 4–128 μg ml^?1 reduced germination of spores of B. cinerea and M. piriformis, and 2,4-D and paraquat at 32 μg ml^?1 similarly affected B. cinerea and P. expansum. Several herbicides at 128 μg ml^?1 in agar reduced growth of B. cinerea and M. piriformis but were ineffective against P. expansum. Propagule survival levels of the three fungi generally were lower in both autoclaved and non-autoclaved soil amended with herbicides than in non-amended soil. This effect was greatest in non-autoclaved soil, suggesting involvement of microbial antagonists. The most effective herbicides for reduction of fungal propagules in soil were 2,4-D, diuron, and paraquat.     

Effect of propiconazole on growth and sterol biosynthesis by Sclerotium rolfsii

Germination of sclerotia ofSclerotium rolfsii on agar nutrient medium was delayed or slightly inhibited by concentrations of propiconazole between 0.4 and 4.0 μg ml^?1, but was strongly inhibited by 8 μg ml^?1 and completely inhibited by 16 μg ml^?1. On the other hand, growth of hyphae from the germinated sclerotia was strongly inhibited by propiconazole at 1 μg ml^?1 or greater. Hyphal growth from agar discs on agar medium was about 8 times less sensitive than hyphal growth from the sclerotia or from hyphal inoculum in liquid media. Propiconazole at 0.25 and 1.0 μg ml^?1 strongly inhibited ergosterol biosynthesis, but this was not associated with large accumulations of C-14 methyl sterols. The ratio of eburicol to ergosterol in hyphae grown in the presence of 0.25 μg ml^?1 propiconazole for 16, 30 or 45 h was 0.11, 0.13 and 0.04, respectively, for the three intervals while for hyphae grown in the presence of 1 μg ml^?1, the ratios were 0.29, 0.36 and 0.30, respectively, for the same intervals. In view of a ratio of 23.5 for¹⁴C-acetate incorporation into the two sterols during the initial 6 h growth period in the presence of propiconazole, it is believed that the lack of large accumulation of C-14 methyl sterols is due to the feedback inhibition by eburicol or to cell lysis when the content of ergosterol becomes too low in the actively growing cells.     

Disposition kinetics of cypermethrin and fenvalerate in black bengal lactating goats

Disposition kinetics of cypermethrin and fenvalerate were investigated in lactating black Bengal goats following single dose intravenous administration at 57 and 45 mg kg^?1 respectively. The maximum and minimum blood concentrations of cypermethrin were 18.49 (±3.17) and 0.06 (±0.002) μg ml^?1, while the corresponding values for fenvalerate were 14.58 (±2.37) and 0.04 (±0.005) μg ml^?1 respectively. Both cypermethrin and fenvalerate remained present in blood for 36 h. The mean t1/2β) and Vd_area values were 5.56 (±0.28) h and 10.38 (±2.20) litre kg^?1 for cypermethrin and 5.66 (±0.35) h and 11.31 (±2.20) litre kg^?1 respectively for fenvalerate. Both cypermethrin and fenvalerate persisted in goat milk for 36 h. The t1/2β) and AUC values of fenvalerate were 7.37 (±1.84) h and 122.38 (±11.65) μg h ml^?1 whilst the corresponding values for cypermethrin were 6.66 (±1.54) h and 99.48 (±7.81) μg h ml^?1 in milk respectively.     

Effect of fenpropimorph and imazalil on sterol biosynthesis in penicillium italicum

Fenpropimorph was found to be highly active against Penicillium italicum (EC₅₀ 0.01/μg ml^?1). Conidia of P. italicum, treated with low concentrations of fenpropimorph, swelled in size and showed distorted germ tubes. During the initial stages of mycelial growth, fenpropimorph had little or no effect on the dry weight increase, which became strongly inhibited within 24 h after addition of the toxicant (0.05, 0.1 and 0.2 μg ml^?1). Irregular deposition of β–1,3 and β–1, 4 polysaccharides, probably chitin, was observed after treatment with fenpropimorph or imazalil. Fenpropimorph (0.05 and 0.2 μ ml^?1) caused the accumulation of a major demethyl-sterol that was different from ergosterol. It was identified as ergosta-8, 14, 24(28)-trien-3β-ol by mass, infrared, ultraviolet and proton nuclear magnetic resonance, spectrometric procedures. At both concentrations, the accumulation was already detected after incubation for 2 h. In contrast, imazalil (0.1 μg ml^?1) caused the accumulation of several methyl- and dimethyl-sterols which were tentatively identified as eburicol (24-methylene-24, 25-dihydrolanosterol), 4, 14α-dimethylergosta-8, 24(28)-dien-3-one, 14α-methylergosta-8, 24(28)-dien-3-one and obtusifoliol (4, 14α-dimethylergosta-8, 24(28)-dien-3α-ol). The accumulation of ergosta-8, 14,24(28)-trien-3β-ol indicates inhibition of the Δ¹⁴-reductase in P. italicum in a similar manner to that found previously in Ustilago maydis.     

Quantitative bioassays for determining residues and availability to plants of sulphonylurea herbicides

A bioassay procedure for quantitative determination of sulphonylurea herbicides is described. Turnips (Brassica rapa) were found very suitable as test plants and gave results within 10 days. Six sulphonylurea compounds were investigated for their activity in three widely differing soils. The potential availability to plants was calculated from the dose-response curves of vermiculite (non-sorptive substrate) and the corresponding ED₅₀-values of the soils. The dose-response relationship (logistic curve) was described by a computer model by a position parameter, the slope of the curve and the minimum and maximum fresh weights of plants. The limit of quantitative detection in the range of ED₃₀ in vermiculite was 0·06 μg 1^?1 for sulfometuron and 1·03 μg 1^?1 for DPX-L5300, methy12-([4-methoxy-6-methyl-1,3,5-triazin-2-yl (methyl)carbamoyl]-sulphamoyl) benzoate. Results with turnips showed that sulfometuron was the most active compound in all substrates (ED₅₀ in vermiculite 0·12 μg 1^?1) followed by chlorsulfuron, metsulfuron-methyl, triasulfuron, DPX-M6316, methyl 3-([(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbamoyl]-aminosulphaphamoyl)-2-thiophenecarboxylate, and DPX-L5300 which had ED₅₀ or 1·98 μg 1^?1, The Horotiu sandy loam soil showed the highest ED₅₀-values and the lowest plant availability for all compounds compared to the other soils. Probit and logistic evaluation methods for deriving dose-response relationships are compared and their applicability is discussed.     

Characterization of herbicidal injury by acifluorfen-methyl in excised cucumber (Cucumis sativus L.) cotyledons

Initial signs of herbicidal injury by several diphenyl ether herbicides were monitored by following the efflux of ⁸⁶Rb⁺ from treated cucumber (Cucumis sativis L.) cotyledons after exposure to light (600 μE m^?2 sec^?1; measured as PAR, i.e., photosynthetically active radiation between 400 and 700 nm). This very sensitive, rapid, and quantitative bioassay proved quite useful in (a) a structure-activity correlations study of the diphenyl ether compounds investigated and (b) an examination of herbicidal characteristics. The following diphenyl ether herbicides were analyzed: acifluorfen, sodium 5-[2-chloro-4-(trifluormethyl)phenoxy]-2-nitrobenzoate; acifluorfen-methyl (MC-10108), methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate; bifenox, methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate; nitrofen, 2,4-dichlorophenyl p-nitrophenyl ether; nitrofluorfen, 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene; oxyfluorfen, 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene; MC-7783, potassium 5-(2,4-dichlorophenoxy)-2-nitrobenzoate; and MC-10982, ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate. Of the compounds investigated, acifluorfen-methyl (AFM) had the greatest degree of herbicidal activity. Cucumber cotyledons placed in high light (600 μE m^?2 sec^?1; PAR) with 10 nM AFM showed a significant increase in the efflux of ⁸⁶Rb⁺ within 2 to 4 hr. Light was required for herbicidal activity by AFM, and when treated cotyledons were returned to darkness, no further damage to the tissue occurred. By decreasing the quantity of light, the effect of the compound was delayed, although the magnitudes of the responses at the different intensities (600, 300, 150, and 75 μE m^?2 sec^?1; PAR) were nearly equal. By increasing the length of time of dark pretreatment with 1 μM AFM, ⁸⁶Rb⁺ efflux could be detected as early as 10 to 15 min after exposure to light (600 μE m^?2 sec^?1; PAR). Following light activation of AFM there was a simultaneous efflux of ⁸⁶Rb⁺, ³⁶Cl^?, ⁴⁵Ca²⁺, 3-O-methyl-[¹⁴C]glucose, and [¹⁴C]methylamine⁺. These data suggest the initial response to the herbicidal activity of AFM is expressed as a general increase in membrane permeability.     

Adsorption-leaching study of the herbicides metamitron and chloridazon

Freundlich isotherms were obtained for the adsorption equilibrium of the herbicides metamitron and chloridazon with the components of a representative soil in a pesticide concentration range of 10-1000 γg ml^?1 for metamitron and 10-500 μg ml^?1 for chloridazon. The mobility of these herbicides through soil columns was also studied using the displacement technique described by Davidson (Soil Sci. Soc. Amer. Proc., 32 (1968) 629). The experiment was carried out simultaneously in three columns, two of which were fed with solutions of the herbicides while the third was used as a control. The herbicide solutions flowed down by gravity and were collected at the outlet at different times. The herbicide content of these outlet solutions was determined by Differential Pulse Polarography.     

Variations among field isolates of Botrytis cinerea in their sensitivity to antifungal compounds

Seventeen field isolates of Botrytis cinerea were compared by determining their radial growth on synthetic media containing various amounts of 21 antifungal compounds. Twelve of these compounds were fungicides that are recommended for the control of Botrytis infections. There were marked differences between the isolates in their sensitivity to the compounds. Individual isolates displayed high levels of resistance to some of the fungicides, including benomyl, carbendazim, iprodione, thiabendazole, thiophanate-methyl, vinclozolin and zineb. The most potent growth inhibitors were benomyl and carbendazim (ED₉₅ values for most isolates <0.1 μg fungicide ml^?1 media), dichlofluanid, iprodione, nystatin, thiabendazole, thiophanatemethyl and vinclozolin (ED₉₅ values for most isolates < 1.0 μg ml^?1), and captan, chlorothalonil, dicloran and thiram (ED₉₅ values for most isolates < 6.0 μg ml^?1). Zineb was much less potent than the other recommended anti-Botrytis fungicides; it was no more effective than carboxin, dinocap and mancozeb (ED₉₅ values for most isolates > 25 μg ml^?1).     

Non-target effect of herbicides: I. effect of glyphosate and hexazinone on soil microbial activity. Microbial population,and in-vitro growth of ectomycorrhizal fungi

The effects of two herbicides, glyphosate (as a 359 g litre^?1 SL) and hexazinone (as a 50gkg^?1 granule) on soil microbial population, carbon dioxide evolution, and in-vitro growth of five species of ectomycorrhizal fungi were investigated. Glyphosate at 0–54 and 3.23 kg a.i. ha^?1 and hexazinone at 1. 2 and 8 kg a.i. ha^?1 did not reduce soil microbial population or carbon dioxide evolution in the long term (6 months). However, there was a significant short-term (2 months) effect of glyphosate on both fungal and bacterial counts at the 0.54 kg ha^?1 treatment. In in-vitro tests, Cenococcum graniforme. Hebeloma crustuliniforme and Laccaria laccata were more susceptible to both herbicides than was Suillus tomentosus. which was, in turn, more susceptible than Paxillus involutus. The growth of all five ectomycorrhizal fungi was significantly reduced when subjected to concentrations above 50 μl formulation litre^?1 (glyphosate) or 50 μg formulation litre^?1 (hexazinone).     

Integrated pest management: A strategy to control resistance of Spodoptera exigua and Helicoverpa armigera caterpillars to insecticides on soybean in the Mekong Delta

The antibiotic nucleoside tubercidin produced by Streptomyces viola-ceoniger was evaluated for in-vivo efficacy and in-vitro activity against Phytophthora capsici, Magnaporthe grisea and Colletotrichum gloeosporioides. Tubercidin was more effective against P. capsici and M. grisea than against C. gloeosporioides in inhibiting mycelial growth. The bioassay on TLC plates was the most sensitive method and allowed the evaluation of antifungal activity of tubercidin even at a low concentration of 0.1 μgml^?1. As compared to the systemic fungicide metalaxyl, tubercidin was similar or somewhat higher in inhibition of mycelial growth of P. capsici. When applied to pepper stems, tubercidin was equally as effective as metalaxyl in the control of phytophthora blight in pepper plants, irrespective of application time and concentration. The treatment with 1000 μg ml^?1 tubercidin induced phytotoxicity in pepper plants. No control efficacy of phytophtora blight was observed in pepper plants supplied with a soil drench of tubercidin. Treatment with tubercidin at 500 μg ml^?1 completely protected pepper plants at first branch stage from phytophthora blight until four days after application. The control efficacy of tubercidin drastically declined seven days after application.     

Failure to detect highly resistant strains in dicarboximide resistant field populations of Botrytis cinerea1

Field isolates of Botrytis cinerea with moderate levels of resistance to dicarboximide fungicides (ED50 1.0–4.9 μg ml^?1) and to dicloran were obtained from glasshouses where vinclozolin and iprodione failed to control grey mould. From sensitive and moderatcly-resistant cultures, laboratory isolates were selected on dicarboximide-amended medium, which were highly resistant to these fungicides (ED50 125->3000 μg ml^?1). Conidia of all the resistant isolates germinated well on media amended with 100 μg ml^?1 of the dicarboximides vinclozolin, iprodione, procymidone and myclozolin and with 5 μg ml^?1 of metomeclan. However, the spores of the moderately resistant isolates did not germinate on 100 μg ml^?1 metomeclan while the spores of the highly resistant isolates germinated well. Using media with 100 μg ml^?1 of metomeclan to distinguish between the two phenotypes, no highly resistant strain was detected among 312 resistant samples from five cucumber glasshouses with a high frequency of moderately resistant strains. From air-borne inoculum of five glasshouses with 100% resistant populations, 1604 colonies were recovered on vinclozolin-amended (100 μg ml^?1) medium and none on metomeclan-amended (100 μg ml^?1) medium. It is concluded that strains of B. cinerea highly resistant to dicarboximides are absent from field populations.     

Uptake,metabolism and effects of DDT,fenitrothion and chlorpyrifos on Tetrahymena pyriformis

The uptake and metabolism of DDT, fenitrothion and chlorpyrifos were studied in cultures of the ciliate protozoan Tetrahymena pyriformis. When cultures were treated with DDT in concentrations varying from 0.01 to 0.5 μg ml⁻¹, concentrations found in T. pyriformis were 3.8 to 335 μg g⁻¹ dry weight. The accumulation of fenitrothion ranged from 28.7 μg g⁻¹ in cultures treated with 1 μg ml⁻¹ to 2260 μg g⁻¹ in cultures treated with 10 μg ml⁻¹. Under similar experimental conditions chlorpyrifos was accumulated from 24.7 to 15400 μg g⁻¹. The patterns of uptake were dependent on the growth cycle, the ability of the organism to metabolise insecticide and the type of the insecticide used. Maximum accumulation of DDT, fenitrothion and chlorpyrifos occurred in 2, 4 and 6 h respectively. Tetrahymena metabolised DDT to DDD and DDE but failed to metabolise fenitrothion and chlorpyrifos. The effects on growth and morphology of T. pyriformis were studied over a period of 5 days. Higher concentrations (10, 50 and 100 μg ml⁻¹) of DDT inhibited only the growth of the organisms and did not change cell morphology. Fenitrothion was extremely toxic to the organisms and at 5 and 10 μg ml⁻¹ cells became more or less spherical and died after 48 h. However, concentrations of 0.5, 1 and 2.5 μg ml⁻¹ fenitrothion caused growth inhibition, but only at 2.5 μg ml⁻¹ was this permanent. Chlorpyrifos inhibited the growth of the organisms at 1, 5 and 10 μg ml⁻¹ but the morphology was affected only at 5 and 10 μg ml⁻¹.     

Effect of atrazine on growth, production of aflatoxin, and fatty acid and sterol biosynthesis by Aspergillus spp.

The effects of atrazine were studied on growth, production of aflatoxin, and fatty acid and sterol biosynthesis by four isolates of Aspergillus in vitro. There was little effect of atrazine on Aspergillus spp. at concentrations up to 20 μg ml^?1 but at 40 μg ml^?1 or above, growth, production of aflatoxin, and fatty acid and sterol biosynthesis were remarkably reduced. Palmitic, stearic and linoleic acid synthesis were inhibited in three of the isolates tested at 60 μg ml^?1. At 100 μg ml^?1, except ergosterol, the cholesterol and 5, 7-ergostadienol synthesis was totally inhibited in all isolates. Effet de l'atrazine sur la croissance, la production d'aflatoxine, et la biosynthèse d'acides gras et de stérols par Aspergillus spp. Chez quatre isolats d'Aspergillus, les effets de l'atrazine sur la croissance, la production d'aflatoxine, et la biosynthèse d'acides gras et de stérols ont étéétudiés in vitro. Jusqu'à des concentrations de 20 μg ml^?1, l'atrazine n'a eu que peu d'effets, mais à 40 μg ml^?1 et au-dessus, la croissance, la production d'aflatoxine, et la biosynthèse d'acides gras et de stérols ont été nettement réduites. Les synthèses d'acides palmitique, stéarique et linoléique ont été inhibées chez trois des isolats, à 60 μg ml^?1. A 100 μg ml^?1, mis à part l'ergostérol, les synthèses de cholestérol et de 5, 7-ergostanediol ont été totalement inhibées chez tous les isolats. Die Wirkung von Atrazin aufdas Wachslum, die Bildung von Aflatoxin und die Fettsäuren- und Sterol-Biosynthese von Aspergillus spp. Bei vier Isolaten von Aspergillus wurde in vitro die Wirkung auf das Wachstum sowie auf die Bildung von Aflatoxin, Fettsäuren und Sterolen untersucht. Bei Atrazin-Konzentrationen bis zu 20 μg ml^?1 war keine Wirkung zu beobachten, aber ab 40 μg ml^?1 wurden das Wachstum und die Bildung von Aflatoxin, Fettsäuren und Sterolen deutlich herabgesetzt. Bei 60 μg ml^?1 war bei drei Isolaten die Bildung von Palmitin-, Stearin- und Linolensäure gehemmt. Bei 100 μg ml^?1 war bei alien Isolaten die Bildung von Cholesterol und 5, 7-Ergostadienol, aber nicht Ergosterol, unterbunden.     

Structure-activity relationship of herbicides inhibiting ACh-induced contractions in a molluscan smooth muscle

Certain herbicides are known to influence the muscle function of molluscs. The penis-retractor muscle complex (PRM complex) of the edible snail, Helix pomatia, is a suitable test object for studying these side effects in smooth muscle, because sequential contractions can be induced in vitro by adding and removing acetylcholine (ACh). In the presence of herbicidal amides, carbamates, and ureas (concentration, 10^?4 mol/liter) the muscle tension was found to be reduced to a variable extent. In contrast, the relaxing effect of herbicidal phenoxycarbonic acids was weak. The inhibitory properties of the herbicides tested were correlated with the electron-withdrawing properties of certain substituents. These substituents are bound to an amino function. Their structure is either aromatic (amides, biscarbamates, carbamates, ureas), aliphatic (thiocarbamates), or cycloaliphatic (cycloat). The structure-activity relationship is comparable with that found for herbicidal activity in plants.     

Leaching of atrazine and hexazinone from Abies nordmanniana (Steven) spach plantations

The content of the herbicides atrazine and hexazinone was measured in drainage water from seven to ten-year-old plantations grown with Abies nordmanniana (Steven) Spach on two clayey soils in Denmark. The concentrations of atrazine varied between 0.06 and 7.79 μg litre^?1. The concentrations of hexazinone were different at the two locations, ranging from 0.07 to 2.09 μg litre^?1 at Bremersvold and from 3.47 to 42.66 μg litre^?1 at Koege. Metabolites of both herbicides were identified.     

Effects of the experimental fungicide RH 886 on Mucor piriformis

No registered fungicide controls Mucor piriformis, a cause of severe postharvest storage rot in pears, but the experimental fungicide RH 886 (active ingredients: 77% 5-chloro-2-methylisothiazol-3-(2H)-one and 23% 2-methylisothiazol-3-(2H)-one) has an ED₅₀ of 23.1 μg ml^?1 in 5 min exposure for germination of sporangiospores of M. piriformis and an ED₅₀ of 9.9 μg ml^?1 for mycelial growth. Mixing RH 886 into infested, amended soil at 8 mg g^?1 soil or mixing copper sulfate into soil at 1 mg g^?1 soil prevented sporulation of M. piriformis. Application of RH 886 to pear fruits prior to inoculation, or immersion of fruits in solutions of RH 886 containing sporangiospores of M. piriformis significantly reduced fruit infection.     

Cytological and physiological studies of the effects of IBP on Pyricularia oryzae (II): Effects on apical cells of single hyphae

The effects of IBP (S-benzyl O,O-diisopropyl phosphorothioate) on tips of single hyphae of Pyricularia oryzae were investigated by interference contrast microscopy. Labelling hyphae with calcofluor white followed by IBP treatment revealed that elongation of apices of almost all hyphae at the colony margin was inhibited after treatment for 4 h. Successive observations on single hyphae of an IBP-sensitive isolate indicated that apical cells stopped elongating approximately 10 min after the onset of treatment with 2 μg IBP ml^?l. Small vacuoles appeared after 50 min; later they increased in number and size, and coalesced, finally producing a chain-like arrangement of vacuoles in the cytoplasm. When hyphae were treated with 10 μg IBP ml^?1, cessation of elongation and vacuolation occurred earlier than when treated with 2 μg ml^?1. Apical cells of hyphae of an IBP-tolerant isolate appeared unaltered even when treated with 10 μg ml^?1. These results indicate that a major effect of IBP is to inhibit specifically the growth of apical cells of the IBP-sensitive isolate.     

含肟醚并取代异 NFDA1唑环的氨基甲酸酯类化合物的合成及生物活性

为寻找具有优异生物活性的氨基甲酸酯类化合物,根据活性亚结构拼接原理,将取代异 NFDA1 唑和肟醚基团引入多菌灵结构中,以取代苯甲醛 (1) 和2-氯苄胺(3) 为起始原料,经多步反应设计合成了10个未见文献报道的含肟醚并取代异 NFDA1 唑的氨基甲酸酯类化合物,其结构经 1H NMR 和 MS 确证。初步生物活性测定结果表明,部分目标化合物不仅具有一定的杀菌活性,同时还具有较好的除草活性。其中,活体盆栽试验结果表明,化合物11b对黄瓜霜霉病Pseudoperonospora cubensis 的相对防效为90%,对黄瓜白粉病Sphaerotheca fuliginea 的相对防效达95%,低于对照药剂多菌灵;除草活性皿测法表明,化合物11c和11j 200 mg/L下对靶标作物的根、茎抑制率均达80%以上,与对照药剂异丙酯草醚活性相当。盆栽法表明,150 g/hm2下,化合物11c和11j对繁缕Stellaria media苗前和苗后的抑制率均在70%以上,低于异丙酯草醚。此类化合物的构效关系有待进一步研究。     

Laboratory studies on benzimidazole resistance in Septoria tritici1

A technique is described for testing isolates of Septoria tritici from winter wheat for resistance to benzimidazole fungicides. Secondary spores from 23 isolates were tested on Czapek Dox V-8 agar amended with benomyl at 1–10 μg ml. Twenty-one isolates were recovered from eight crops in England in 1984 and two (PBI isolates) were obtained in 1973. Thirteen isolates, including both PBI isolates, were sensitive to benomyl at 1 μg ml^?1 and nine were resistant at 10 μg ml^?1. The remaining isolate had a low proportion (1:3.7 x 10⁴) of resistant spores. The minimum inhibitory concentration for sensitive isolates was 0.2–0.4 μg ml ¹ benomyl and for resistant isolates was more than 1000 μg ml ¹. Benomyl-resistant isolates were cross-resistant to carbendazim, thiabendazole and thiophanate-methyl, but not to 12 other fungicides with different modes of action. The implications of these findings are discussed.