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1.
BACKGROUND: The intermediate derivatisation method based on bioisosteric replacement led to the discovery of the lead strobilurin compound 5a. To produce new strobilurin analogues with improved activity, a series of substituted pyrimidines were synthesised and bioassayed. RESULTS: The compounds were identified by 1H NMR, IR, MS and elemental analysis. The highly active compound 5g was studied by X‐ray diffraction. Preliminary bioassays demonstrated that some of the title compounds exhibited excellent acaricidal activity against Tetranychus cinnabarinus (Boisd.) at 10 mg L?1. The relationship between structure and acaricidal activity is reported. CONCLUSION: The present work demonstrates that strobilurin derivatives containing pyrimidine moieties can be used as possible lead compounds for developing novel acaricides. Copyright © 2010 Society of Chemical Industry  相似文献   

2.
BACKGROUND: As previously reported, methyl (E)‐2‐[2‐(2‐phenylamino‐6‐trifluoromethylpyrimidin‐4‐yloxymethyl)phenyl]‐3‐methoxyacrylate has proven to be a new lead with highly acaricidal activity. Following on from this, in an effort to discover new strobilurin analogues with improved activity, a series of substituted pyrimidines were synthesised and bioassayed. RESULTS: All compounds were characterised by 1H NMR, IR, MS and elemental analysis. Preliminary bioassays demonstrated that some of the title compounds exhibited notable control of Tetranychus cinnabarinus (Boisd.) at 1.25 mg L?1. The relationship between structure and acaricidal activity is discussed. CONCLUSION: Two compounds of particular interest, 6j (SYP‐10913) and 6k (SYP‐11277), exhibited potent acaricidal activity. The acaricidal potencies of these analogues are higher than that of fluacrypyrim in greenhouse applications, and are comparable with those of commercial acaricides such as spirodiclofen and propargite in field trials. Copyright © 2011 Society of Chemical Industry  相似文献   

3.
BACKGROUND: The lead coumarin derivative (E)‐methyl 3‐methoxy‐2‐[2‐(4‐methylcoumarin‐7‐yloxymethyl)phenyl]acrylate was discovered by using an intermediate derivatisation method. To discover new coumarin derivatives with improved activity, a series of substituted coumarins were synthesised and bioassayed. RESULTS: The compounds were identified by 1H NMR, IR, MS and elemental analysis. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activity against cucumber downy mildew at 25 mg L?1. The relationship between structure and fungicidal activity is reported. CONCLUSION: The present work demonstrates that coumarin derivatives containing methoxyacrylate moieties can be used as possible lead compounds for developing novel fungicides. Copyright © 2011 Society of Chemical Industry  相似文献   

4.
Fifty-three heterocyclic sulphonyl derivatives including eight sulphonamides, three sulphonyl azides, nine sulphonohydrazides and twenty sulphonohydrazones of substituted thiophenes, and a smaller range of analogous isoxazoles pryazoles and thiazoles, were tested as potential fungicides in a simple screening procedure against Mucor mucedo, Septoria nodorum, Trichoderma viride, Chaetomium globosum and Aspergillus niger. Several thiophene-2-sulphonyl based compounds exhibited a high level of antifungal activity at 100 mg litre?1 against the five test species, especially the mono-halogen-substituted sulphonamides and sulphonohydrazines, in which a single chlorine or bromine atom was substituted in the para position of an attached phenyl ring. The most active compound, against all five species of fungus was N-(4-chlorophenyl)-N-(trichloromethylthio) thiophene-2-sulphonamide which had average MIC50 and MIC100 values of 86 and 180 μmol respectively. (MIC50 and MIC100 values are, respectively, the concentrations required to inhibit fungal growth by 50% and to inhibit it totally.) In general, the isoxazole analogues of the thiophene-2-sulphonyl compounds exhibited a much lower fungitoxic activity, whilst the pyrazole and thiazole based compounds had little or no activity. Compared with the other results, the considerable activity shown by 4-[2′-(3,4-dichlorobenzylidene)hydrazinosulphonyl]thiophene-2-carboxylic acid was unexpected.  相似文献   

5.
BACKGROUND: Testing the compatibility of chemical pesticides and fungal biocontrol agents is necessary if these two agents are to be applied together in the integrated management of plant pests and diseases. In this study, the fungicides azoxystrobin (a strobilurin) and flutriafol (a triazole) were tested in vitro for their effects on germination of conidia and mycelial growth of Beauveria bassiana (Bals.) Vuill. and in bioassay for their effect on fungal activity against Tetranychus urticae Koch. The fungicides were tested at three different concentrations [recommended rate for field use (1 × X) and the dilutions 10?1× X and 10?2× X]. RESULTS: Flutriafol inhibited growth of mycelia and germination of the fungal conidia at all concentrations tested in vitro, and also reduced the efficacy of B. bassiana in bioassays against mites. The inhibitive effect of azoxystrobin in vitro varied with the concentration applied. A significant effect was observed at 1 × X and 10?1× X concentrations on both the germination of conidia and mycelia growth. At 10?2× X concentration, azoxystrobin showed little effect on B. bassiana. However, when this fungicide was tested in bioassays, none of the concentrations reduced B. bassiana activity against mites. CONCLUSION: Azoxystrobin was most compatible with B. bassiana, while flutriafol was the most harmful. Further studies are required to confirm the negative effect of flutriafol on B. bassiana activity. Copyright © 2010 Society of Chemical Industry  相似文献   

6.
BACKGROUND: The small number of available nematicides and restrictions on the use of non‐fumigant nematicides owing to high toxicity to human and non‐target organisms hinder effective nematode control. The nematicidal efficacy of MCW‐2, a new nematicide of the fluoroalkenyl group, was evaluated against the root‐knot nematode Meloidogyne javanica (Treub.) Chitwood. RESULTS: MCW‐2 showed irreversible nematicidal activity against second‐stage juveniles of M. javanica in vitro, following exposure for 48 h at concentrations as low as 0.5 mg L?1, in contrast to fenamiphos or cadusafos. When exposed to MCW‐2 for shorter periods, motile juveniles became immobile with time after rinsing in water. MCW‐2 at 8 mg L?1 inhibited nematode hatching, which, however, recovered after rinsing in water. In pot and plot experiments, 0.5 mg MCW‐2 L?1 soil and 2 kg MCW‐2 ha?1, respectively, controlled M. javanica similarly to or better than fenamiphos or cadusafos at the same concentrations or at their recommended doses. In the soil, the nematicidal activity of MCW‐2 was less persistent than that of fenamiphos. CONCLUSION: MCW‐2 has potential to be used as a new non‐fumigant nematicide that probably has a novel mode of action. Copyright © 2009 Society of Chemical Industry  相似文献   

7.
BACKGROUND: Many plant essential oils show a broad spectrum of activity against pests. This study investigated the effects of two essential oils on Tetranychus urticae, one of the most serious pests in the world. RESULTS: The chemical composition of the two oils was characterised by GC‐MS. The most abundant component in the Santolina africana (Jord. & Fourr) oil was terpinen‐4‐ol (54.96%), while thymol (61%) was prevalent in the Hertia cheirifolia (L.) oil. Mortality and fecundity were measured upon treatment with oil concentrations ranging from 0.07 to 6.75 mg L?1 with a Potter spray tower. Mite mortality increased with oil concentration, with LC50 values of 2.35 mg L?1 for S. africana and 3.43 mg L?1 for H. cheirifolia respectively. For both oils, a reduction in fecundity was observed at concentrations of 0.07, 0.09 and 0.29 mg L?1. Artificial blends of constituents of oils were also prepared and tested with individual constituents missing from the mixture. The results showed that the presence of all constituents was necessary to equal the toxicity of the two natural oils. CONCLUSION: S. africana and H. cheirifolia oils can provide valuable acaricide activity with significantly lower LC50 values. Thus, these oils cause important mortality and reduce the number of eggs laid by females. Copyright © 2012 Society of Chemical Industry  相似文献   

8.
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  相似文献   

9.
以(E)-2-[2'-(bromo-methyl)phenyl]3-甲氧基丙烯酸甲酯和2(1H)-喹啉酮类化合物为原料,通过醚化等反应,合成了11个新型含2(1H)-喹啉酮结构的甲氧基丙烯酸酯类化合物,其结构经红外、电喷雾串联质谱(ESI-MS)和核磁共振氢谱确证。初步生物活性测试结果表明:在100 mg/L质量浓度下,部分目标化合物对烟草赤星病菌Alternaria alternata等6种病原菌具有一定的抑菌活性,其中5a对水稻稻瘟病菌Pyricularia grisea的抑菌率达100%。  相似文献   

10.
BACKGROUND: Natural limonoids are one group of compounds being studied for their insecticidal properties. To discover new limonoids with better activities, analogs were prepared via acylation and hydrolysis, and bioassayed. RESULTS: Analogs were identified using one‐ and two‐dimensional (COSY, HMQC and HMBC) 1H and 13C NMR, IR and MS. 3‐O‐Isovalerylswietenolide (13) and 3‐O‐isobutyrylswietenolide (14) showed excellent antifeedant activity, with DC50 values of 0.19 and 0.009 mg L?1 respectively, compared with the natural limonoid swietenolide (80.6 mg L?1) against fourth‐instar Spodoptera frugiperda (JE Smith) larvae. CONCLUSION: This work shows that limonoid analogs prepared through semi‐synthesis can be used as lead compounds for the development of new insecticides. Copyright © 2010 Society of Chemical Industry  相似文献   

11.
BACKGROUND: Isolates of Didymella bryoniae (Auersw.) Rehm, causal agent of gummy stem blight on cucurbits, developed insensitivity to azoxystrobin in the eastern United States 2 years after first commercial use in 1998. Baseline sensitivity of this fungus to azoxystrobin has never been reported. The objectives were to compare baseline sensitivities of D. bryoniae from South Carolina and other locations to sensitivities of isolates exposed to azoxystrobin for one or more seasons, and to compare sensitivity in vitro and in vivo. RESULTS: Sixty‐one isolates of D. bryoniae collected before 1998 were sensitive. Median EC50 was 0.055 mg L?1 azoxystrobin (range 0.005 to 0.81). Forty isolates collected after exposure during 1998 also were sensitive. Fifty‐three of 64 isolates collected in South and North Carolina between 2000 and 2006 were insensitive to 10 mg L?1 azoxystrobin. Sensitive and insensitive isolates were distinguished by disease severity on Cucumis melo L. seedlings treated with azoxystrobin (20 or 200 mg L?1). CONCLUSIONS: An azoxystrobin baseline sensitivity distribution was established in vitro for isolates of D. bryoniae never exposed to strobilurins. Baseline values were comparable with those of other ascomycetes. Insensitive isolates were found in fields with a history of strobilurin applications. An in vivo method distinguished sensitive and insensitive isolates. Copyright © 2009 Society of Chemical Industry  相似文献   

12.
BACKGROUND: 4‐(3‐Trifluoromethylphenyl)pyridazine represents a new series of compounds with bleaching and herbicidal activities. RESULTS: A total of 43 novel 3‐(substituted benzyloxy or phenoxy)‐6‐methyl‐4‐(3‐trifluoromethylphenyl)pyridazine derivatives were synthesised, and their bleaching and herbicidal activities were evaluated through Spirodela polyrrhiza and greenhouse tests. Some compounds exhibited excellent herbicidal activities, even at a dose of 7.5 g ha?1. CONCLUSION: The results showed that a substituted phenoxy group at the 3‐position of the pyridazine ring and the electron‐withdrawing group at the para ‐position on the benzene ring were essential for high herbicidal activity. Copyright © 2011 Society of Chemical Industry  相似文献   

13.
以取代α-三氟甲基苯乙烯和取代的肉桂醛肟为原料,经过1,3-偶极环加成反应,合成了16个未见文献报道的含三氟甲基异噁唑啉结构的目标化合物,其结构经1H NMR和LC-MS确认。初步杀虫活性测试结果表明:在500 mg/L下,大部分目标化合物对斜纹夜蛾Prodenia litura和粘虫Mythimna sepatara具有一定的杀虫活性,其中ZJ11对粘虫的致死率达100%,即使在100 mg/L下,其致死率仍达80%。  相似文献   

14.
Wang Z  Kim JR  Wang M  Shu S  Ahn YJ 《Pest management science》2012,68(7):1041-1047
BACKGROUND: An assessment was made of the toxicity of imperatorin and osthole identified in Cnidium monnieri fruit, 11 related compounds and five insecticides to larvae from insecticide‐susceptible Culex pipiens pallens (KS‐CP strain) and Aedes aegypti and wild C.p. pallens (YS‐CP colony) using a direct‐contact mortality bioassay. Results were compared with those of the conventional larvicide temephos. RESULTS: Imperatorin (LC50 = 3.14 and 2.88 mg L?1) was 1.9‐, 3.7‐ and 4.2‐fold and 2.4‐, 4.5‐ and 4.6‐fold more toxic than isopimpinellin, isoimperatorin and osthole against susceptible C. p. pallens and A. aegypti larvae respectively. Overall, all of the compounds were less toxic than temephos (0.011 and 0.019 mg L?1). The toxicity of these compounds was virtually identical against larvae from the two Culex strains, even though YS‐CP larvae were resistant to fenthion (resistance ratio RR = 390), deltamethrin (RR = 164), cyfluthrin (RR = 14) and temephos (RR = 14). This finding indicates that the coumarins and the insecticides do not share a common mode of action. The structure–activity relationship indicates that the chemical structure and alkoxy substitution and length of the alkoxyl side chain at the C8 position are essential for imparting toxicity. CONCLUSION: The C. monnieri fruit‐derived coumarins and the related coumarins described merit further study as potential insecticides or lead molecules for the control of insecticide‐resistant mosquito populations. Copyright © 2012 Society of Chemical Industry  相似文献   

15.
BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, 1H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC50 values of 8.05 and 10.56 µg mL?1 respectively. Commercial fungicide procymidone provided an EC50 value of 0.63 µg mL?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry  相似文献   

16.
BACKGROUND: The excellent fungicidal activity of [1,2,4]triazolo[1,5‐a]pyrimidines suggested the search for further analogues with improved properties. RESULTS: A series of novel trisubstituted pyrido[2,3‐b]pyrazines has been designed and prepared as 6,6‐biheterocyclic analogues of related 5,6‐bicyclic [1,2,4]triazolo[1,5‐a]pyrimidines. Their fungicidal activity was evaluated against the plant pathogens Puccinia recondita Rob. ex Desm. f. sp. tritici (Eriks.) CO Johnston (wheat brown rust), Mycosphaerella graminicola (Fuckel) Schroter (Septoria tritici Rob., leaf spot of wheat) and Magnaporthe grisea (Hebert) Barr (Pyricularia oryzae Cav., rice blast). Structure–activity relationship studies revealed the advantage of a fluoro substituent in position 6 and of a secondary amine in position 8. CONCLUSION: 8‐Amino‐7‐aryl‐6‐halogen‐substituted pyrido[2,3‐b]pyrazines have been prepared as 6,6‐biheterocyclic analogues of similarly substituted triazolopyrimidine fungicides. A concise four‐step synthesis route has been worked out to prepare these novel compounds from commercially available starting materials. [(R)‐(1,2‐Dimethylpropyl)]‐[6‐fluoro‐7‐(2,4,6‐trifluorophenyl)pyrido[2,3‐b]pyrazin‐8‐yl]amine showed excellent activity against three economically important phytopathogens. Copyright © 2009 Society of Chemical Industry  相似文献   

17.
BACKGROUND: Botrytis cinerea Pers.: Fr. is a high‐risk pathogen for fungicide resistance development that has caused resistance problems on many crops throughout the world. This study investigated the fungicide sensitivity profile of isolates from kiwifruits originating from three Greek locations with different fungicide use histories. Sensitivity was measured by in vitro fungitoxicity tests on artificial nutrient media. RESULTS: Seventy‐six single‐spore isolates were tested for sensitivity to the SDHI fungicide boscalid, the QoI pyraclostrobin, the anilinopyrimidine cyprodinil, the hydroxyanilide fenhexamid, the phenylpyrrole fludioxonil, the dicarboxamide iprodione and the benzimidazole carbendazim. All isolates from Thessaloniki showed resistance to both boscalid and pyraclostrobin, while in the other two locations the fungal population was sensitive to these two fungicides. Sensitive isolates showed EC50 values to boscalid and pyraclostrobin ranging from 0.9 to 5.2 and from 0.04 to 0.14 mg L?1 respectively, while the resistant isolates showed EC50 values higher than 50 mg L?1 for boscalid and from 16 to > 50 mg L?1 for pyraclostrobin. All QoI‐resistant isolates carried the G143A mutation in cytb. Sensitivity determinations to the remaining fungicides revealed in total eight resistance phenotypes. No isolates were resistant to the fungicides fenhexamid and fludioxonil. CONCLUSION: This is the first report of B. cinerea field isolates with resistance to both boscalid and pyraclostrobin, and it strongly suggests that there may be a major problem in controlling this important pathogen on kiwifruit. Copyright © 2010 Society of Chemical Industry  相似文献   

18.
设计合成了14个含1,2,4-噻二唑环的甲氧丙烯酸酯类新化合物,其结构经红外、电喷雾串联质谱(ESI-MS)和核磁共振氢谱确证。生物活性测定结果表明,化合物 7j、7k、7m、7n 在 100 mg/L质量浓度下对小麦赤霉病菌等6种供试病原菌均有较高抑菌活性, 其中7i 对小麦赤霉病菌Fusarium graminearum的抑菌率为100%。  相似文献   

19.
BACKGROUND: Although more than ten strobilurin analogues have been commercialized since 1996 as fungicides, only one was available as an acaricide as of 2003. To search for novel strobilurin analogues with unique biological activities, a synthetic screening programme was carried out. RESULTS: Syntheses of compounds analogous to the commercialized fungicide metominostrobin and the acaricide fluacrypyrim led to the discovery of a lead compound, (E)‐2‐{2‐[[3,5‐bis(trifluoromethyl)phenoxy]methyl]phenyl}‐2‐(methoxyimino)‐N‐methylacetamide (3b), that showed moderate acaricidal activity against Tetranychus urticae Koch. Compound 3b has a 3,5‐(CF3)2‐phenoxymethyl group instead of the unsubstituted phenoxy substituent in metominostrobin. Optimization of compound 3b was achieved by introducing an oxime ether bridge along with an alkylthio(alkyl) branch in place of the oxymethylene chain between two aromatic moieties, as well as by replacing the methoxyiminoacetamide group with a methoxyacrylate structure, leading to (E)‐ methyl 2‐{2‐[[[(Z)[1‐(3,5‐bis(trifluoromethyl)phenyl)‐2‐methylthioethylidene]amino]oxy] methyl]phenyl}‐3‐methoxyacrylate (6c) and (E)‐ methyl 2‐{2‐[[[(Z)[1‐(3,5‐bis(trifluoromethyl)phenyl)‐1‐methylthiomethylidene]amino]oxy]methyl]phenyl}‐3‐methoxyacrylate (9a, HNPC‐A3066). CONCLUSION: The above two compounds (6c, 9a) were shown to exhibit potent acaricidal and fungicidal activity. Compound 9a (HNPC‐A3066) also exhibits larvicidal and ovicidal activities against various acarids. The acaricidal potency is comparable with those of commercial acaricides such as fluacrypyrim, tebufenpyrad and chlorfenapyr. Copyright © 2008 Society of Chemical Industry  相似文献   

20.
BACKGROUND: In 2004, field isolates of Botrytis cinerea Pers. ex Fr., resistant to strobilurin fungicides (QoIs), were first found in commercial citrus orchards in Wakayama Prefecture, Japan. Subsequently, QoI‐resistant isolates of this fungus were also detected in plastic strawberry greenhouses in Saga, Ibaraki and Chiba prefectures, Japan. Biological and molecular characterisation of resistant isolates was conducted in this study. RESULTS: QoI‐resistant isolates of B. cinerea grew well on PDA plates containing kresoxim‐methyl or azoxystrobin at 1 mg L?1, supplemented with 1 mM of n‐propyl gallate, an inhibitor of alternative oxidase, whereas the growth of sensitive isolates was strongly suppressed. Results from this in vitro test were in good agreement with those of fungus inoculation tests in vivo. In resistant isolates, the mutation at amino acid position 143 of the cytochrome b gene, known to be the cause of high QoI resistance in various fungal pathogens, was found, but only occasionally. The heteroplasmy of cytochrome b gene was confirmed, and the wild‐type sequence often present in the majority of resistant isolates, indicating that the proportion of mutated cytochrome b gene was very low. CONCLUSION: The conventional RFLP and sequence analyses of PCR‐amplified cytochrome b gene are insufficient for molecular identification of QoI resistance in B. cinerea. Copyright © 2009 Society of Chemical Industry  相似文献   

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