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1.
Cyclization of 3‐aryl‐1‐(2‐hydroxyphenyl)prop‐2‐en‐1‐ones with hydrazine hydrate in refluxing formic acid afforded the title ligands, 5‐aryl‐1‐formyl‐4,5‐dihydro‐3‐(2‐hydroxyphenyl)‐1H‐pyrazoles (HL1–HL4, Ar = Ph, 4‐CH3O‐C6H4‐, 2‐furyl, 2‐thienyl). Reaction of HL1–HL4 with the divalent metal ions, Mn2+, Co2+, Ni2+, Cu2+, and Zn2+, afforded novel complexes of the type [ML2] (M = metal ion; L = deprotonated ligand) which were characterized by elemental analyses, molecular weight determinations, molar conductances, magnetic moments and electronic and infrared spectral data. The ligands behaved as tridentate, coordinating through the phenolic oxygen after deprotonation, N‐2 of the pyrazole ring and oxygen of the 1‐formyl group. The ligands and their complexes were evaluated for growth‐inhibiting activity against four phytopathogenic fungi. Macrophomina phaseoli was generally most sensitive followed by Alternaria alternata and Colletotrichum falcatum while Fusarium oxysporum was least sensitive to the tested compounds. The ligand HL1 and its complexes showed the best activity against the fungi tested. © 2000 Society of Chemical Industry  相似文献   

2.
1,5‐Diphenyl‐1‐pentanone (A) and 1,5‐diphenyl‐2‐penten‐1‐one (B) are natural products extracted for the first time from Stellera chamaejasme. Laboratory bioassay showed that the two products have strong contact activity and very good anti‐feedant activity against Aphis gossypii and Schizaphis graminum. Both products showed dose‐dependent relationships for both forms of activity against the two aphids, the contact activity of B being about twice that of A. Both products were inferior to methomyl in contact activity but superior in anti‐feedant activity against the two aphids. This is the first report of aphicidal activity in these two compounds, which may represent a new class of aphicide. © 2001 Society of Chemical Industry  相似文献   

3.
BACKGROUND: The susceptibility of adult house cricket, Acheta domesticus (L.), adult convergent lady beetle, Hippodamia convergens (Guérin‐Méneville), and larval fall armyworm, Spodoptera frugiperda (JE Smith), to resmethrin and δ‐phenothrin synergized with piperonyl butoxide (PBO) was evaluated in a laboratory bioassay procedure. RESULTS: The 1 day LC50 values for resmethrin + PBO were 23.2, 32.08 and 307.18 ng cm?2 for A. domesticus, H. convergens and S. frugiperda respectively. The 1 day LC50 values for δ‐phenothrin + PBO were 26.9, 74.91 and 228.57 ng cm?2 for A. domesticus, H. convergens and S. frugiperda respectively. The regression relationship between species mortality and concentration explained 51–81% of the variation for resmethrin + PBO and 72–97% of the variation for δ‐phenothrin + PBO. The LC50 values decreased with time for these insecticides for all surrogate species. In terms of sensitivities among the insects to resmethrin + PBO and δ‐phenothrin + PBO, A. domesticus was most sensitive, followed by H. convergens and then S. frugiperda. CONCLUSION: The results indicate that resmethrin + PBO was generally more toxic than δ‐phenothrin + PBO. Based on the results, A. domesticus seems to be a good surrogate species for estimating potential non‐target terrestrial insect impacts from exposure to pyrethroids used in public health applications. Copyright © 2008 Society of Chemical Industry  相似文献   

4.
Derivatives of 2‐ethyl‐1,3,4(2H)‐isoquinolinetrione in which the 4‐keto group has been modified to (Z)‐oxime, (E)‐ and (Z)‐O‐methyl oxime, (Z)‐N,N‐dimethyl hydrazone, cyano‐imine and dicyanomethylene moieties have been prepared and evaluated as redox mediator herbicides. All of the compounds have the free‐radical properties required to function as redox mediators, as determined by cyclic voltammetry, though only the O‐methyl oximes, the N,N‐dimethyl hydrazone and the cyano‐imine have reduction potentials in the range required to stimulate the light‐dependent consumption of oxygen at photosystem I in isolated chloroplasts. The O‐methyl oximes and the cyano‐imine are fast‐acting post‐emergence herbicides, producing symptoms of rapid desiccation; the (E)‐O‐methyl oxime is the most active herbicide, being somewhat more potent than the parent isoquinolinetrione. Hydrolysis studies indicate that it is unlikely that any compound generates the parent isoquinolinetrione in vivo. Attempts to explain differences between in vitro and in vivo activities using hydrolytic stabilities and physical properties were unsuccessful, and it was concluded that these factors probably play a less significant role in moderating the herbicidal activity of isoquinolinetrione derivatives than originally thought. © 2000 Society of Chemical Industry  相似文献   

5.
All isomers of α‐asarone [(E)‐4‐prop‐1‐enyl‐1,2,5‐trimethoxybenzene] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)‐2‐prop‐1‐enyl‐1,3,5‐trimethoxybenzene exhibited the strongest deterrent activity against all the species tested. The total coefficients of deterrency for this compound were 140.6 and 169.7 for Tribolium confusum adults and larvae, respectively, and 144.9 and 104.6 for larvae of Trogoderma granarium and adults of Sitophilus granarius, respectively. © 2000 Society of Chemical Industry  相似文献   

6.
A series of novel 3‐(2,4,6‐trisubstituted phenyl)uracil derivatives has been synthesised and assayed for insecticidal/acaricidal activity. The assay indicated certain requirements for optimal insecticidal activity, which can be summarised as follows: (a) the substituents on the phenyl ring should possess hydrophobicity and electron‐withdrawing properties, and the sum of their volumes determines the level of activity; (b) the substituent at the 6‐position on the uracil ring should also possess electron‐withdrawing properties and hydrophobicity, together with the correct volume; (c) the 1‐position on the uracil ring should be unsubstituted for activity against Nephotettix cincticeps and Epilachna vigintioctopunctata, but substituents with length C3 to C4 may be optimal for activity against Tetranychus urticae; (d) certain substituents at the 5‐position of the uracil ring give activity against E vigintioctopunctata and T urticae, but not against N cincticeps; (e) a thiocarbonyl group at the 2‐position of the uracil ring is less effective than a carbonyl group. Of the compounds assayed, 3‐(2,6‐dichloro‐4‐trifluoromethylphenyl)‐6‐trifluoromethyluracil showed high activity against all the species assayed. © 2000 Society of Chemical Industry  相似文献   

7.
BACKGROUND: Finger millet is a major food crop as well as feed and fodder for livestock, especially in regions of southern India. A sturdy crop to fluctuating environmental conditions, it can be cultivated in all seasons of the year. Leaf, neck and finger blast caused by Pyricularia grisea Sacc. and Bipolaris setariae (Saw.) Shoem, as well as leaf spot disease, Bipolaris nodulosa (Berk & M.A.Curtis) Shoem, are major production constraints in southern India. Apart from environmental conditions, the use of harvested seeds by farmers is a major reason for disease prevalence. Benzophenone analogues have been investigated for controlling phytopathogenic fungi. In addition, the most important applications of azetidin‐2‐ones are as antibiotics. Based on this information, the present study was conducted to explore the antifungal activity of integrated 2‐azetidinonyl and 1,3,4‐oxadiazoles moieties into a benzophenone framework. RESULTS: A simple high‐yielding method for the integration of heterocyclic rings, namely 2‐azetidinonyl, at the benzophenone nucleus has been achieved, starting from substituted 2‐hydroxybenzophenones under mild conditions on a wet solid surface using microwave irradiation. In the present study, an array of newly synthesised compounds, 2‐azetidinonyl‐5‐(2‐benzoylphenoxy)methyl‐1,3,4‐oxadiazoles, were screened for their antifungal property against blast and leaf spot causing fungi associated with the seeds of finger millet, cv. Indof‐9. CONCLUSION: Two of the newly synthesised compounds showed promising effects in depleting the incidence of seed‐borne pathogenic fungi of finger millet. The suppression of Pyricularia grisea and Bipolaris setariae resulted in enhanced seed germination and seedling growth. Copyright © 2009 Society of Chemical Industry  相似文献   

8.
6‐Hydroxy‐5‐isopropyl‐3,8‐dimethyl‐4a,5,6,7,8,8a‐hexahydronaphthalen‐2(1H)‐one (HHO) is an allelopathic substance that is related to allelochemical metabolism in Eupatorium adenophorum. In this study, the full‐length complementary DNA of two phenylalanine ammonia‐lyase (PAL) genes and a fragment of the cinnamate 4‐hydroxylase (CA4H) gene from E. adenophorum (Ea) were cloned. The expression of all three genes was increased by the HHO treatment, with varying sensitivity: EaPAL2 > EaPAL1 > EaCA4H. Southern blotting suggested that there is a third member of the PAL gene family in this species.  相似文献   

9.
Until recently, Digitaria aequiglumis var. aequiglumis, native to South America, and Digitaria ciliaris subsp. nubica, native to Northeast Africa, were completely overlooked in Belgium due to their close morphological resemblance to Digitaria sanguinalis and Digitaria ischaemum. One of the possible reasons for their expansion in maize fields, besides for example the lack of crop rotation, might be a lower sensitivity to post‐emergence herbicides acting against panicoid grasses. Dose – response pot experiments were conducted in the glasshouse to evaluate the effectiveness of four foliar‐applied HPPD‐inhibiting herbicides (mesotrione, sulcotrione, tembotrione, topramezone) and two foliar‐applied ALS‐inhibiting herbicides (foramsulfuron, nicosulfuron) for controlling Belgian populations of D. aequiglumis and D. ciliaris subsp. Nubica, as well as local D. sanguinalis and D. ischaemum populations. In another dose–response pot experiment, the influence of growth stage at time of herbicide application on efficacy of topramezone and nicosulfuron for Digitaria spp. control was evaluated. In general, D. aequiglumis and D. ciliaris subsp. nubica populations were less sensitive to HPPD inhibitors than D. ischaemum and D. sanguinalis populations, except for D. aequiglumis treated with topramezone. Contrary to other herbicides tested, topramezone adequately controlled all D. aequiglumis populations at doses well below maximum authorised field dose. All species tested showed a progressive decrease in sensitivity to topramezone and nicosulfuron with seedling age. A satisfactory post‐emergence control of Digitaria species in the field will require appropriate choice of herbicide and dose, as well as more timely application.  相似文献   

10.
BACKGROUND: Some twig beetles in the genus Pityophthorus (Coleoptera: Scolytinae) may vector pitch canker disease Fusarium circinatum (Niremberg & O'Donnell) of Pinus spp. (Pinaceae). Because Pityophthorus pubescens (Marsh.) has been found to be associated with F. circinatum in the Basque Country (northern Spain), various experiments were conducted to assess the beetle's behavioural responses to (E, E)‐α‐farnesene, (R)‐(+)‐limonene and (S)‐(?)‐verbenone to develop a potential inhibitor to host attraction. These experiments comprise electroantennographic and double‐choice olfactometer tests, as well as field assays in Pinus radiata D. Don stands. RESULTS: Both sexes of P. pubescens showed similar electroantennographic responses to different doses (from 1 ng to 1 µg in decadic steps) of each individual compound, with depolarisations to (S)‐(‐)‐verbenone (100 ng) being similar to those of the aggregation pheromone (+)‐trans‐pityol. In olfactometer assays, both sexes were significantly attracted to (+)‐trans‐pityol, but the attraction was reduced when increasing amounts of the chemicals were added to the pheromone. Particularly relevant was the repellent effect induced by (S)‐(?)‐verbenone at 1 ng dose and higher. In the field, (E, E)‐α‐farnesene, (R)‐(+)‐limonene and (S)‐(?)‐verbenone reduced significantly the number of beetles attracted to (+)‐trans‐pityol and racemic trans‐pityol, with (S)‐(?)‐verbenone being the most effective. CONCLUSIONS: (S)‐(?)‐Verbenone showed an interesting potential for use in the protection of P. radiata stands. A potentially effective strategy, which could be implemented in further, more in‐depth studies, could involve the use of this semiochemical as repellent and (+)‐trans‐pityol‐baited traps as attractant in a ‘push‐pull’ strategy. Copyright © 2012 Society of Chemical Industry  相似文献   

11.
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12.
Studies were conducted to explain the relative success of ‘Dickeya solani’, a genetic clade of Dickeya biovar 3 and a blackleg‐causing organism that, after recent introduction, has spread rapidly in seed potato production in Europe to the extent that it is now more frequently detected than D. dianthicola. In vitro experiments showed that both species were motile, had comparable siderophore production and pectinolytic activity, and that there was no antagonism between them when growing. Both ‘D. solani’ and biovar 1 and biovar 7 of D. dianthicola rotted tuber tissue when inoculated at a low density of 103 CFU mL?1. In an agar overlay assay, D. dianthicola was susceptible to 80% of saprophytic bacteria isolated from tuber extracts, whereas ‘D. solani’ was susceptible to only 31%, suggesting that ‘D. solani’ could be a stronger competitor in the potato ecosystem. In greenhouse experiments at high temperatures (28°C), roots were more rapidly colonized by ‘D. solani’ than by biovar 1 or 7 of D. dianthicola and at 30 days after inoculation higher densities of ‘D. solani’ were found in stolons and progeny tubers. In co‐inoculated plants, fluorescent protein (GFP or DsRed)‐tagged ‘D. solani’ outcompeted D. dianthicola in plants grown from vacuum‐infiltrated tubers. In 3 years of field studies in the Netherlands with D. dianthicola and ‘D. solani’, disease incidence varied greatly annually and with strain. In summary, ‘D. solani’ possesses features which allow more efficient plant colonization than D. dianthicola at high temperatures. In temperate climates, however, tuber infections with ‘D. solani’ will not necessarily result in a higher disease incidence than infections with D. dianthicola, but latent seed infection could be more prevalent.  相似文献   

13.

BACKGROUND

Transgenic maize (Zea mays L.) event TC1507 (Herculex® I insect protection), expressing Cry1F δ‐endotoxin derived from Bacillus thuringiensis var. aizawai, was commercialized in 2003 in the Americas. Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) susceptibility to Cry1F was monitored annually across several regions in Argentina using diagnostic concentration bioassays. Reduced performance of TC1507 maize against S. frugiperda was reported in 2013. A resistant population was established in the laboratory and the dominance of Cry1F resistance was characterized.

RESULTS

During 2012–2015, high‐survivorship of several populations was observed in the resistance monitoring program. Reciprocal crosses of a Cry1F‐resistant population with a Cry1F‐susceptible population were evaluated to calculate effective dominance (DML) based on mortality levels observed at 100 µg/ml Cry1F. Two additional dominance levels (DLC and DEC) were calculated using lethal (LC50) or effective concentration (EC50) derived from concentration–response bioassays. Estimates indicated that Cry1F resistance in S. frugiperda in Argentina was either highly recessive (DML = 0.005) or incompletely recessive (DLC < 0.26 and DEC < 0.19).

CONCLUSION

This study is the first documented confirmation and characterization of S. frugiperda Cry1F field‐evolved resistance in Argentina. The resistance to Cry1F in S. frugiperda populations collected in Argentina, is autosomal and incompletely recessive similar to the resistance reported in Brazil. © 2017 The Authors. Pest Management Science published by John Wiley © Sons Ltd on behalf of Society of Chemical Industry.  相似文献   

14.
UV irradiation of metoxuron in aerated aqueous solution at 254 nm or between 300 and 450 nm led initially to an almost specific photohydrolysis of the C–Cl bond, resulting in the formation of 3‐(3‐hydroxy‐4‐methoxyphenyl)‐1,1‐dimethylurea (MX3) and hydrogen chloride. The quantum yield was determined to be 0.020 (±0.005) in solutions irradiated at 254 nm. Five minor photoproducts were also identified, in particular the dihydroxydimethoxybiphenyl derivatives resulting from the phototransformation of MX3. Irradiation increased the toxicity of an aqueous solution of metoxuron to the marine bacterium Vibrio fischeri. © 2001 Society of Chemical Industry  相似文献   

15.
A preinoculative soil drench application of 0·5 mm β‐aminobutyric acid (BABA) significantly inhibited colonization of oilseed rape (Brassica napus, susceptible cultivar Falcon) by Verticillium longisporum and also prevented plant stunting caused by the pathogen. To better understand the defence responses induced by BABA, the presence of occlusions in the plant hypocotyl, levels of salicylic acid (SA) and hydrogen peroxide (H2O2), phenylalanine ammonia lyase (PAL) activity and expression of PR‐1 and PDF1.2 genes were examined. Transverse sections through the hypocotyl region of BABA‐treated plants showed clear vessels surrounded by phenol‐storing cells, in contrast to numerous obstructed vessels in water‐treated plants, in response to the pathogen. A significant increase in SA levels was observed in the hypocotyls of both water‐ and BABA‐treated plants in response to the pathogen; however, SA levels were unrelated to disease resistance. The level of H2O2 decreased in both treatments in response to the pathogen. A significant increase in PAL activity was observed in hypocotyl tissues of BABA‐treated plants. The expression patterns of PR‐1 and PDF1.2 were similar in the two treatments in response to the pathogen, indicating no involvement of these genes in resistance. The results indicate a similar organ specificity of the plant hypocotyl for chemically induced internal resistance as for genotype‐related resistance, two phenomena which, however, are based on contrasting cytological responses in the vascular tissues. Nonetheless, evidence is provided that the activity of the phenylpropanoid pathway plays a crucial role in both types of resistance.  相似文献   

16.
Insecticidal δ‐endotoxin proteins, degraded from parasporal crystals by protease, were recovered by a simple procedure using heat treatment, solubilization, and ultrafiltration of a fermentation broth of Bacillus thuringiensis subsp kurstaki HD‐1. A 68 kDa insecticidal protein was obtained and characterized by SDS‐PAGE. The procedure described gave a nearly quantitative recovery of toxicity. Furthermore, bioassay results on larvae of the diamondback moth (Plutella xylostella) showed that the 68 kDa δ‐endotoxin fraction (P1) was the principal insecticidal component to this target insect. A similar molecular mass polypeptide P2 (65 kDa) which was solubilized together with P1 from the parasporal crystals, gave relatively low mortality. © 2000 Society of Chemical Industry  相似文献   

17.
The association of the cell wall degrading enzyme endo‐beta‐1,4‐xylanase (EC 3.2.1.8) with pathogenicity of Mycosphaerella graminicola was examined in planta. The enzyme production of two M. graminicola isolates (T0372 and T0491), as well as their ability to infect seedlings of susceptible wheat cv. Scorpion, was first compared. No significant difference was found between the two isolates regarding spore germination rates, mycelial growth on the leaf surface or direct and stomatal penetrations. However, restricted hyphal growth was observed inside leaves inoculated with T0372, whereas successful mesophyll colonization with a strong intercellular fungal growth was found in leaves infected with T0491. Likewise, T0372 was unable to induce lesions bearing pycnidia and to produce endo‐beta‐1,4‐xylanase activity until 22 days post‐inoculation (d.p.i.). On the other hand, significant high increases of both diseased leaf area bearing pycnidia and endo‐beta‐1,4‐xylanase activity were observed between 16 and 22 d.p.i. for T0491 (r = 0·98). The investigation of 24 additional isolates, including the IPO323 and IPO94269 reference isolates, highlighted a strong correlation between endo‐beta‐1,4‐xylanase activity and disease development levels (r = 0·94). This study demonstrates that differences in pathogenicity in M. graminicola are not linked to events on the leaf surface or to frequency of leaf penetration, but to the ability of the fungus to colonize the mesophyll and to produce the cell wall degrading enzyme endo‐1,4‐beta‐xylanase during the necrotrophic phase.  相似文献   

18.
Mecoprop was irradiated under various conditions of pH, oxygenation and wavelengths in order to study the reactions involved in the phototransformation. Four main photoproducts were identified: 2‐(4‐hydroxy‐2‐methylphenoxy)propionic acid ( I ), o‐cresol ( II ), 2‐(5‐chloro‐2‐hydroxy‐3‐methylphenyl)propionic acid ( III ) and 4‐chloro‐o‐cresol ( IV ). When the anionic form of mecoprop was irradiated between 254 nm and 310 nm (UV‐C or UV‐B), I was the main photoproduct. At 254 nm its formation initially accounted for more than 80% of the transformation. It has not previously been reported in the literature. The reaction results from a heterolytic photohydrolysis. Product II accounted for only a low percentage of the transformation. The stoichiometry was different with the molecular form: the main photoproduct, III , resulted from a rearrangement after a homolytic scission. Products I, II and IV were also formed as minor photoproducts. Some other minor photoproducts were also identified. In contrast, IV was the main photoproduct under sunlight irradiation or when solutions were irradiated in near‐UV light (UV‐A). This wavelength effect is attributed to the involvement of an induced phototransformation; IV is also the main photoproduct when the phototransformation is induced by Fe( III ) perchlorate or nitrite ions. In usual environmental conditions the excitation of the molecular form is negligible and the phototransformation is mainly due to induced photoreactions. © 2000 Society of Chemical Industry  相似文献   

19.
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20.
Cinnamate‐4‐hydroxylase (CA4H), a cytochrome P450‐dependent monooxygenase, plays crucial roles in phenylpropanoid metabolism and plant defense. Previously, the authors showed that the expression of CA4H was induced in response to an allelopathic substance in Eupatorium adenophorum. Here, the full‐length cDNA of EaCA4H was cloned by using rapid amplification of cDNA ends. The 1518 bp open reading frame of EaCA4H was deduced to encode a protein of 505 amino acid residues. Like other CA4H proteins, the predicted EaCA4H polypeptides contained conserved domains of cytochrome P450. A Southern blot analysis indicated that at least five copies of EaCA4H exists in the genome of E. adenophorum. Subcellular localization revealed nuclear‐localized EaCA4H–green fluorescent protein fusion protein in onion epidermal cells. Heterologous silencing of endogenous CA4H in tobacco by a conserved EaCA4H fragment resulted in reduced expressions of key enzymatic genes and the production of downstream flavonoids in the phenylpropanoid pathway. Intriguingly, similar effects were observed in transgenic tobacco plants overexpressing EaCA4H. Altogether, the results indicate that the disturbed expression of CA4H in plants leads to relatively low expression levels of key enzymatic genes and the accumulation of the flavonoids that are involved in phenylpropanoid metabolism.  相似文献   

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