A number of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines were synthesized. The structures of these new compounds were confirmed by ^1H NMR, IR and elemental analysis. Biological evalua...A number of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines were synthesized. The structures of these new compounds were confirmed by ^1H NMR, IR and elemental analysis. Biological evaluation in the greenhouse showed several compounds have good fungicidal activities at 25 mg/L.展开更多
The title compound has been synthesized by the reaction of 4-tert-butyl-5-（1,2,4- triazol-1-yl）-2-aminothiazole with propionic anhydride, and its crystal structure was determined by single-crystal X-ray diffraction....The title compound has been synthesized by the reaction of 4-tert-butyl-5-（1,2,4- triazol-1-yl）-2-aminothiazole with propionic anhydride, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group Pbca with α = 18.441（2）, b = 8.3284（9）, c = 19.257（2） A, Z = 8, V = 2957.5（5） A3, Mr = 279.37, Dc = 1.255 mg/m3, S = 1.033, μ =0.219 mm^-1, F（000） = 1184, the final R = 0.0349 and wR = 0.0876 for 2629 observed reflections （I 〉 2σ（I））. X-ray crystal structure presents the intermolecular N–H···N hydrogen bond, which plays an important role in stabilizing the crystal structure. The preliminary bioassay indicates that the title compound exhibits potent fungicidal activity against R. Solani （25 mg/L） with inhibition rate of 80.0%.展开更多
The title compound has been synthesized by the reaction of 3,3-dimethyl-1-（1H-1,2,4-triazol-1-yl）butan-2-one oxime with 2-chlorobenzyl chloride, and then treated with 65～68% HNO3. Its crystal structure was determin...The title compound has been synthesized by the reaction of 3,3-dimethyl-1-（1H-1,2,4-triazol-1-yl）butan-2-one oxime with 2-chlorobenzyl chloride, and then treated with 65～68% HNO3. Its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 14.5481（8）, b = 9.3351（5）, c = 13.1911（7） , β = 98.9450（10）°, Z = 4, V = 1769.67（17） 3, Mr = 369.81, Dc = 1.388 g/cm3, S = 1.06, μ = 0.247 mm-1, F（000） = 776, the final R = 0.0352 and wR = 0.0960 for 3069 observed reflections （I 2σ（I））. X-ray crystal structure presents the intramolecular N–H…O hydrogen bond. The packing is nearly parallel without π-π stacking interactions between two adjacent phenyl rings and stabilized by Van der Waals force. The preliminary bioassay shows that the title compound possesses fungicidal activity against Gibberella zeae at the dosage of 25 mg/L.展开更多
The title compound （E）-2-[（4-tert-butyl-5-（4-methoxybenzyl）thiazol-2-ylimino）methyl]phenol was synthesized by the reaction of 5-（4-methoxybenzyl）-4-tert- butylthiazol-2-amine with salicylaldehyde, and its crys...The title compound （E）-2-[（4-tert-butyl-5-（4-methoxybenzyl）thiazol-2-ylimino）methyl]phenol was synthesized by the reaction of 5-（4-methoxybenzyl）-4-tert- butylthiazol-2-amine with salicylaldehyde, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 5.9362（8）, b = 11.5070（15）, c = 29.460（4）A, β= 97.326（3）°, V = 1995.9（5） A^3, Z = 4, F（000） = 808, C22H24N2O2S, Mr= 380.49, De= 1.266 g/cm^3, S = 1.031,μ = 0.181 mm^-1, the final R = 0.0474 and wR = 0.1441 for 4327 observed reflections （I 〉 2σ（I））. Intramolecular O-H…N hydrogen bond is observed in the crystal. The preliminary bioassay showed that the title compound exhibits 95% inhibition rate against Rhizoctonia solani at the test concentration of 500 mg/L.展开更多
Citral(Eo)exhibits excellent fungicidal activities.However,it is difficult to maintain long-term fungicidal activity due to its strong volatility.Herein,a controlled-release strategy by using biomass-derived porous ca...Citral(Eo)exhibits excellent fungicidal activities.However,it is difficult to maintain long-term fungicidal activity due to its strong volatility.Herein,a controlled-release strategy by using biomass-derived porous carbon(BC)was developed to overcome the drawback of Eo.New composite materials were prepared by loading Eo on tea stem porous carbon(BC@Eo),and their controlled-release fungicidal activity against Exobasidium vexans was assessed.BC with a large specific surface area of 1001.6 m2/g and mesoporous structure was fabricated through carbonization tempera-ture of 700℃.The BC@Eo materials were characterized using Fourier-transform infrared spectroscopy and X-ray powder diffraction.The results suggested that chemical and physical interactions occurred in BC@Eo.The Eo release profile suggested a biphasic pattern with an initial fast release on days 1–14 and a subsequent controlled phase on days 14–30.The in vitro cumulative release percentage of Eo from BC@Eo was 51%during one month,and this result was significantly lower than that from free Eo(cumulative release percentage of Eo of 82%in one week).The anti-fungal activities of Eo and BC@Eo against E.vexans were determined using the inhibition zone method.The results indicated that Eo and BC@Eo formed large inhibition zones of 19.66±0.79 and 21.92±0.77 mm,respectively.The influence on the hyphal structure of E.vexans was observed by scanning electron microscopy on day 30.The hyphal structure of E.vexans treated with BC@Eo was more shrunken than that treated with Eo at 30 days,suggesting that BC@Eo prolongs the fungicidal activity against E.vexans.This study demonstrated that the encapsulation of Eo in BC for developing the BC@Eo materials could be a promising strategy to inhibit volatility and maintain the fungicidal activity of Eo and provide a potential alternative for the reuse of abundant tea biomass waste resources.展开更多
The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by...The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by single crystal X ray diffraction. The crystal is monoclinic, space group P2 1/n , a=10.862(2), b=11.541(2), c=14\^994(3), β=108.41(3)°, V=1783(1), Z=4, D x =1.381 g/cm -3 , μ =0.3361 mm -1 , and F (000)=768. The results confirmed that the title compound belongs to type E of stereochemistry. The dihedral angle between triazole and 1,3,4 thiadiaole ring is 3° and the torsion angle between 1,3,4 thiadiazole and pyrazole ring is 134.0°.展开更多
A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one（I） from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety ...A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one（I） from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR,1H NMR, and HRMS（ESI） or elemental analysis,13 C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method.All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 mmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure–activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.展开更多
[Objective]The paper was to develop a novel fungicide with high efficacy and low toxicity.[Method]Chlorothalonil was used as the parent structure,and its 4-position substituent was converted to amino group.Totally 12 ...[Objective]The paper was to develop a novel fungicide with high efficacy and low toxicity.[Method]Chlorothalonil was used as the parent structure,and its 4-position substituent was converted to amino group.Totally 12 amide compounds not reported in the literature were designed and synthesized.Their structures were conformed by 1H NMR.[Result]The preliminary bioassay test showed that compounds JTCN-01,JTCN-05 and JTCN-07 had good control effect on corn rust at the concentration of 200 mg/L,and the control effect of compound JTCN-05 reached 95%.[Conclusion]Some chlorothalonil derivatives had the potential for further development.展开更多
This study was undertaken to explore new antifungal compounds from the methanolic extract of G. sinaicus. Two cardenolide compounds were isolated and identified by GC-MS as cardenolide glycoside, 15-hydroxy-3,4,5,6-de...This study was undertaken to explore new antifungal compounds from the methanolic extract of G. sinaicus. Two cardenolide compounds were isolated and identified by GC-MS as cardenolide glycoside, 15-hydroxy-3,4,5,6-dehydrocalotropin and cardenolide genin, 3,4,5,6-dehydrocalotropagenin. The antifungal activity of these compounds was assessed. Results revealed that both compounds showed pronounced fungicidal activity against both soil borne fungi, R. solani, F. oxysporium, and postharvest fungi, R. stolonifer, P. digtatum, compared to the standard fungicides, flutolanil and copper oxychloride, respectively. The ECs0 values of the cardenolide genin were 0.703, 13.63 and 4.22, 8.403 lag/mL forR. solani, F. oxysporium andR. stolonifer, P. digtatum respectively. On the other hand, the ECs0 values of the standard fungicide, flutolanil, were 9.49 and 61.22 ~tg/mL against R. solani and F. oxysporium. While the ECso values of copper oxychloride were 279.94 and 187.13 p.g/mL against R. stolonifer and P. digtatum, respectively. The results showed that cellulase, PME, PPO of the tested fungi was more sensitive than to cardenolide genin. The strong antifungal activity of cardenolide genin reported in this study indicated that has a potential to be used as fungicides.展开更多
Benzoxaborole,a five-membered oxaborole ring fused with a phenyl ring,has demonstrated potent pharmacological activity.In order to explore their potential applications in agriculture,five-membered and six-membered ben...Benzoxaborole,a five-membered oxaborole ring fused with a phenyl ring,has demonstrated potent pharmacological activity.In order to explore their potential applications in agriculture,five-membered and six-membered benzoxaborole derivatives were synthesized and evaluated for their fungicidal activity against six common plant pathogenic fungi in vitro.The bioassay results showed that most of the target compounds exhibited significant fungicidal activity at concentrations below 50μg/mL,particularly the highlighted compounds 4b and 4e,which demonstrated impressive fungicidal activity superior to those of the positive controls.Molecular docking was also performed to confirm the practical value of the active compound as a potential inhibitor of Leucyl-tRNA Synthetase(LeuRS).This study indicates that the designed benzoxaborole derivatives could serve as template molecules for the development of novel fungicides.展开更多
3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2 H-chromen-2-ones,a kind of coumarin derivatives,were synthesized byβ-ketoester formation and cyclization.Target compound 5 e was crystallized from methano...3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2 H-chromen-2-ones,a kind of coumarin derivatives,were synthesized byβ-ketoester formation and cyclization.Target compound 5 e was crystallized from methanol for structural identification as monoclinic crystal system,space group C2/c with a=16.2700(6),b=7.1801(5),c=23.4861(10)A,V=2742.6(2)A^(3),Z=8,Dc=1.756 g/cm^(3),F(000)=1456 andμ=0.827 mm-1.8308 Reflections were collected(6.01≤2θ≤50.05°),of which 2428 were unique(Rint=0.0432)and used in all calculations.The final R=0.0408(I>2σ(I))and w R=0.1056(reflections).In vitro bioassay indicated that compounds 5 d&5 e possessed good activity against Botrytis cinerea,Physalospora piricola,Rhizoctonia solani,and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85μg/m L than that of positive control osthole with its EC50 values between 7.38 and 74.59μg/mL.In vivo screening showed that 5 e exhibited 98%and 95%efficacy against Pseudoperonospora cubensis(Berk.&Curt.)Rostov.at 100 and 50μg/mL,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with coumarin was an effective way to novel fungicide development.展开更多
3,4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole,a novel purine derivative,was synthesized by the cyclization of pyrimidine amine.Its structure was characterized by ^(1)H NMR,^(13)C NMR,^(19)FNMR,...3,4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole,a novel purine derivative,was synthesized by the cyclization of pyrimidine amine.Its structure was characterized by ^(1)H NMR,^(13)C NMR,^(19)FNMR,H RMS and single-crystal X-ray diffraction.This compound 3 is crystallized from a mixed solvent of dichloromethane and n-hexane (1:2,v/v) for structural identification as monoclinic crystal system,space group P2_(1)/n with a=11.66250(10),b=8.21300(10),c=17.77920(10)?,V=1676.34(3)?^(3),Z=4,D_(c)=1.643 g/cm^(3),F(000)=832.0 andμ=6.301 mm^(-1).22315 reflections were measured (8.43≤2θ≤158.10°),of which 3532 were unique (R_(int)=0.0311) and used in all calculations.The final R=0.0334 (I>2σ(I)) and w R=0.0842 (reflections).The title compound showed over 50%of growth inhibition against Botrytis cinereal,Cercospora arachidicola,Gibberella zeae,Rhizoctonia solani and Sclerotinia sclerotiorum at 50 mg/L,and its EC_(50) value against R.solani was 60.44μmol/L,which was active at the same level as that of positive control diflumetorim with its EC_(50) value of 60.29μmol/L and less active than YZK-C22 with its EC_(50) value of 12.32μmol/L,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with purine could be an effective way to novel fungicide development.展开更多
The novel fungicidal agents, （E）-5-[1-（2-oxo-l-oxaspiro[4,5]dec/non-3-en-3-yl）ethylidene]-2-aminoimidazolin- 4-one derivatives, were designed and synthesized in moderate to excellent yields in four steps using a-h...The novel fungicidal agents, （E）-5-[1-（2-oxo-l-oxaspiro[4,5]dec/non-3-en-3-yl）ethylidene]-2-aminoimidazolin- 4-one derivatives, were designed and synthesized in moderate to excellent yields in four steps using a-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7h exhibit 96.4%, 92.5%, 90.3% and 76.9% inhibition rates against Phytophthora capsici at the concentration of 50 μg/mL, respectively. These compounds exhibited significant fungicidal activities against S. scleotiorum and P. capsici with EC50 values of 2.56 --11.60 μg/mL, and compounds 6e and 7h exhibited weak inhibition against the spore germination of S. scleoti- orum, while the spore germination ofP. capsici was strongly inhibited by compound 7h solution. Scanning electron microscopy （SEM） and transmission electron microscopy （TEM） observation indicated that compound 7h had a significant impact on the structure and function of the hyphal cell wall ofP. capsici mycelium.展开更多
[ Objective] The paper was to preliminarily identify the species of six actinomyeetes strains, and to determine the fungicidal activities of their fermenta- tion products. E Method ] The species of six aefinomyeetes s...[ Objective] The paper was to preliminarily identify the species of six actinomyeetes strains, and to determine the fungicidal activities of their fermenta- tion products. E Method ] The species of six aefinomyeetes strains were identified by morphological method, and the fungicidal activities of the fermentation products of six aetinomycetes strains were systematically determined by series of methods including mycellal growth rate inhibition method, spore germination method, potting and field test. []Result] Morphological identification results showed that six strains belonged to Streptornyces. Biological determination results indicated that the in- hibition rates of the fermentation products of six actinomycetes strains with the concentration of 500μg/nd against the mycelial growth of Fusar/um oxysporum f. sp. Vasinfeetum were all greater than 90% ; the inhibition rates against the myeelial growth of Botrytis cinerea Pers. , A/ternar/a a/zernate and Fusarium oxysporum were also greater than 80%. The inhibition rates of the fermentation products of GZ-204 and GZ-331 strains against the spore germination of Bipolaria sorokiniana and Cercospora sorghl were 97. 8% , 98.2%, 99.5% and 94.6%, respectively. Potting test showed that the protection effects of the fermentation products of GZ-204 and GZ-331 strains on wheat powdery mildew（Erysiphe graminis） were 78.8% and 87.1% , and their cure effects were 62.4% and 68.5% , respectively. Field test showed that the control effects of 200 times fermentation liquids of GZ-204 and GZ-331 strains on wheat powdery mildew were 50.5% and 69. 2%, respective- ly. [Condusion] The research provided the reference for the development of new pesticides with actinomyeetes as the resource.展开更多
Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP...Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP51) and the docking results of inhibitors to the active site of the enzyme. All title compounds were first by reported. Results of preliminary biological tests showed that most of title compounds exhibited activity against the seven common pathogenic fungi. Compound 11 showed best antifungal activity with broad antifungal spectrum and proved to be more active against Cryptococcus neoformans, Candida albicans, Microsporum lanosum and Trichophyton rubrum than ketoconazole. Compounds 3, 10 and 4 also had high activities.展开更多
In recent years,the damage caused by soil nematodes has become increasingly serious;however,the varieties and structures of the nematicides available on the market are deficient.Fluopyram,a succinate dehydrogenase inh...In recent years,the damage caused by soil nematodes has become increasingly serious;however,the varieties and structures of the nematicides available on the market are deficient.Fluopyram,a succinate dehydrogenase inhibitor(SDHI)fungicide developed by Bayer AG in Germany,has been widely used in the prevention and control of soil nematodes due to its high efficiency and novel mechanism of action.In this paper,two series of novel target compounds were designed and synthesized with nematicidal and fungicidal fluopyram as the molecular skeleton in order to introduce sulfide and sulfone substructures.The structures were identified and characterized by 1H nuclear magnetic resonance(NMR),13C NMR,and high-resolution mass spectrometer(HRMS).The bioassays revealed that most of the compounds showed excellent nematicidal activities at 200 lgmL-1 in comparison with fluopyram,while the nematode mortality rate dropped sharply at 100μg·mL-1,except for compounds I-11 and II-6.In terms of fungicidal activity,compound I-9 was discovered to have an excellent inhibitory rate,and a molecular docking simulation was performed that can provide important guidance for the design and exploration of efficient fungicidal lead compounds.展开更多
The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-...The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.展开更多
Abstract： Ten novel 2-alkylthio-5-（3, 4, 5-tribenzyloxyphenyl）-1, 3, 4-oxadiazole derivatives （5a-j） were synthesized from methyl 3, 4, 5-trihydroxybenzoate by ethedfication, hydrazidation, cyclization and thioet...Abstract： Ten novel 2-alkylthio-5-（3, 4, 5-tribenzyloxyphenyl）-1, 3, 4-oxadiazole derivatives （5a-j） were synthesized from methyl 3, 4, 5-trihydroxybenzoate by ethedfication, hydrazidation, cyclization and thioetherification reactions. The structures of 5a-j were confirmed by 1HNMR, MS spectra and elemental analysis. The results indicated that most of the compounds 5 exhibited good fungicidal activities. The activity of 5h is higher than 90% against Fusarium oxysporum and Botrytis cinereapers in 50 mg/L.展开更多
The biological activities of a series of 3,3-spirocyclic indole derivatives containing CF_(2), phosphine oxide,indole, and cyano functional groups were evaluated, and these derivatives were found to exhibit antiTMV, f...The biological activities of a series of 3,3-spirocyclic indole derivatives containing CF_(2), phosphine oxide,indole, and cyano functional groups were evaluated, and these derivatives were found to exhibit antiTMV, fungicidal, and insecticidal activities.展开更多
A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by 1H NMR, 13C NMR spectra and elemental analyses. Preliminary bioass...A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by 1H NMR, 13C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.展开更多
文摘A number of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines were synthesized. The structures of these new compounds were confirmed by ^1H NMR, IR and elemental analysis. Biological evaluation in the greenhouse showed several compounds have good fungicidal activities at 25 mg/L.
基金supported by the Natural Science Foundation of Hunan Province(No.12jj3012)
文摘The title compound has been synthesized by the reaction of 4-tert-butyl-5-（1,2,4- triazol-1-yl）-2-aminothiazole with propionic anhydride, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group Pbca with α = 18.441（2）, b = 8.3284（9）, c = 19.257（2） A, Z = 8, V = 2957.5（5） A3, Mr = 279.37, Dc = 1.255 mg/m3, S = 1.033, μ =0.219 mm^-1, F（000） = 1184, the final R = 0.0349 and wR = 0.0876 for 2629 observed reflections （I 〉 2σ（I））. X-ray crystal structure presents the intermolecular N–H···N hydrogen bond, which plays an important role in stabilizing the crystal structure. The preliminary bioassay indicates that the title compound exhibits potent fungicidal activity against R. Solani （25 mg/L） with inhibition rate of 80.0%.
基金Supported by the Central University Basic Scientific Research Fund of Hunan University (2009)the Key Scientific and Technological Project of Changsha, Hunan Province (No. 0901077-31)
文摘The title compound has been synthesized by the reaction of 3,3-dimethyl-1-（1H-1,2,4-triazol-1-yl）butan-2-one oxime with 2-chlorobenzyl chloride, and then treated with 65～68% HNO3. Its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 14.5481（8）, b = 9.3351（5）, c = 13.1911（7） , β = 98.9450（10）°, Z = 4, V = 1769.67（17） 3, Mr = 369.81, Dc = 1.388 g/cm3, S = 1.06, μ = 0.247 mm-1, F（000） = 776, the final R = 0.0352 and wR = 0.0960 for 3069 observed reflections （I 2σ（I））. X-ray crystal structure presents the intramolecular N–H…O hydrogen bond. The packing is nearly parallel without π-π stacking interactions between two adjacent phenyl rings and stabilized by Van der Waals force. The preliminary bioassay shows that the title compound possesses fungicidal activity against Gibberella zeae at the dosage of 25 mg/L.
基金the National Project of Scientific and Technical Supporting Programs and Ministry of Science & Technology of China (No.2006BAE01A01-4)
文摘The title compound （E）-2-[（4-tert-butyl-5-（4-methoxybenzyl）thiazol-2-ylimino）methyl]phenol was synthesized by the reaction of 5-（4-methoxybenzyl）-4-tert- butylthiazol-2-amine with salicylaldehyde, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 5.9362（8）, b = 11.5070（15）, c = 29.460（4）A, β= 97.326（3）°, V = 1995.9（5） A^3, Z = 4, F（000） = 808, C22H24N2O2S, Mr= 380.49, De= 1.266 g/cm^3, S = 1.031,μ = 0.181 mm^-1, the final R = 0.0474 and wR = 0.1441 for 4327 observed reflections （I 〉 2σ（I））. Intramolecular O-H…N hydrogen bond is observed in the crystal. The preliminary bioassay showed that the title compound exhibits 95% inhibition rate against Rhizoctonia solani at the test concentration of 500 mg/L.
基金Supported by National Modern Agricultural Industry Technology System,Youth Science and Technology Fund of Guizhou Academy of Agricultural Sciences No.[2020]02,Guiding Project of Guizhou Academy of Agricultural Sciences No.[2018]01.
文摘Citral(Eo)exhibits excellent fungicidal activities.However,it is difficult to maintain long-term fungicidal activity due to its strong volatility.Herein,a controlled-release strategy by using biomass-derived porous carbon(BC)was developed to overcome the drawback of Eo.New composite materials were prepared by loading Eo on tea stem porous carbon(BC@Eo),and their controlled-release fungicidal activity against Exobasidium vexans was assessed.BC with a large specific surface area of 1001.6 m2/g and mesoporous structure was fabricated through carbonization tempera-ture of 700℃.The BC@Eo materials were characterized using Fourier-transform infrared spectroscopy and X-ray powder diffraction.The results suggested that chemical and physical interactions occurred in BC@Eo.The Eo release profile suggested a biphasic pattern with an initial fast release on days 1–14 and a subsequent controlled phase on days 14–30.The in vitro cumulative release percentage of Eo from BC@Eo was 51%during one month,and this result was significantly lower than that from free Eo(cumulative release percentage of Eo of 82%in one week).The anti-fungal activities of Eo and BC@Eo against E.vexans were determined using the inhibition zone method.The results indicated that Eo and BC@Eo formed large inhibition zones of 19.66±0.79 and 21.92±0.77 mm,respectively.The influence on the hyphal structure of E.vexans was observed by scanning electron microscopy on day 30.The hyphal structure of E.vexans treated with BC@Eo was more shrunken than that treated with Eo at 30 days,suggesting that BC@Eo prolongs the fungicidal activity against E.vexans.This study demonstrated that the encapsulation of Eo in BC for developing the BC@Eo materials could be a promising strategy to inhibit volatility and maintain the fungicidal activity of Eo and provide a potential alternative for the reuse of abundant tea biomass waste resources.
文摘The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by single crystal X ray diffraction. The crystal is monoclinic, space group P2 1/n , a=10.862(2), b=11.541(2), c=14\^994(3), β=108.41(3)°, V=1783(1), Z=4, D x =1.381 g/cm -3 , μ =0.3361 mm -1 , and F (000)=768. The results confirmed that the title compound belongs to type E of stereochemistry. The dihedral angle between triazole and 1,3,4 thiadiaole ring is 3° and the torsion angle between 1,3,4 thiadiazole and pyrazole ring is 134.0°.
基金supported by the National Natural Science Foundation of China (No. 21272266)the National High Technology Research and Development Program of China (No. 2011AA10A202)
文摘A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one（I） from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR,1H NMR, and HRMS（ESI） or elemental analysis,13 C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method.All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 mmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure–activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.
基金Supported by Agricultural Science and Technology Innovation Project of Shandong Academy of Agricultural Sciences(CXGC2018E19).
文摘[Objective]The paper was to develop a novel fungicide with high efficacy and low toxicity.[Method]Chlorothalonil was used as the parent structure,and its 4-position substituent was converted to amino group.Totally 12 amide compounds not reported in the literature were designed and synthesized.Their structures were conformed by 1H NMR.[Result]The preliminary bioassay test showed that compounds JTCN-01,JTCN-05 and JTCN-07 had good control effect on corn rust at the concentration of 200 mg/L,and the control effect of compound JTCN-05 reached 95%.[Conclusion]Some chlorothalonil derivatives had the potential for further development.
文摘This study was undertaken to explore new antifungal compounds from the methanolic extract of G. sinaicus. Two cardenolide compounds were isolated and identified by GC-MS as cardenolide glycoside, 15-hydroxy-3,4,5,6-dehydrocalotropin and cardenolide genin, 3,4,5,6-dehydrocalotropagenin. The antifungal activity of these compounds was assessed. Results revealed that both compounds showed pronounced fungicidal activity against both soil borne fungi, R. solani, F. oxysporium, and postharvest fungi, R. stolonifer, P. digtatum, compared to the standard fungicides, flutolanil and copper oxychloride, respectively. The ECs0 values of the cardenolide genin were 0.703, 13.63 and 4.22, 8.403 lag/mL forR. solani, F. oxysporium andR. stolonifer, P. digtatum respectively. On the other hand, the ECs0 values of the standard fungicide, flutolanil, were 9.49 and 61.22 ~tg/mL against R. solani and F. oxysporium. While the ECso values of copper oxychloride were 279.94 and 187.13 p.g/mL against R. stolonifer and P. digtatum, respectively. The results showed that cellulase, PME, PPO of the tested fungi was more sensitive than to cardenolide genin. The strong antifungal activity of cardenolide genin reported in this study indicated that has a potential to be used as fungicides.
基金the financial support for this research from the National Natural Science Foundation of China(22177051,32061143045)the Fundamental Research Funds for the Central Universities(KYCYXT2022010)+1 种基金Sichuan Key Research and Development Program(22ZDYF0186,2021YFN0134)the College Student Research Training Program(202110307002T).
文摘Benzoxaborole,a five-membered oxaborole ring fused with a phenyl ring,has demonstrated potent pharmacological activity.In order to explore their potential applications in agriculture,five-membered and six-membered benzoxaborole derivatives were synthesized and evaluated for their fungicidal activity against six common plant pathogenic fungi in vitro.The bioassay results showed that most of the target compounds exhibited significant fungicidal activity at concentrations below 50μg/mL,particularly the highlighted compounds 4b and 4e,which demonstrated impressive fungicidal activity superior to those of the positive controls.Molecular docking was also performed to confirm the practical value of the active compound as a potential inhibitor of Leucyl-tRNA Synthetase(LeuRS).This study indicates that the designed benzoxaborole derivatives could serve as template molecules for the development of novel fungicides.
基金supported in part by the Tianjin Natural Science Foundation(No.18JCZDJC33500)the National Natural Science Foundation of China(No.31872007)the Tianjin Development Program for Innovation and Entrepreneurship。
文摘3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2 H-chromen-2-ones,a kind of coumarin derivatives,were synthesized byβ-ketoester formation and cyclization.Target compound 5 e was crystallized from methanol for structural identification as monoclinic crystal system,space group C2/c with a=16.2700(6),b=7.1801(5),c=23.4861(10)A,V=2742.6(2)A^(3),Z=8,Dc=1.756 g/cm^(3),F(000)=1456 andμ=0.827 mm-1.8308 Reflections were collected(6.01≤2θ≤50.05°),of which 2428 were unique(Rint=0.0432)and used in all calculations.The final R=0.0408(I>2σ(I))and w R=0.1056(reflections).In vitro bioassay indicated that compounds 5 d&5 e possessed good activity against Botrytis cinerea,Physalospora piricola,Rhizoctonia solani,and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85μg/m L than that of positive control osthole with its EC50 values between 7.38 and 74.59μg/mL.In vivo screening showed that 5 e exhibited 98%and 95%efficacy against Pseudoperonospora cubensis(Berk.&Curt.)Rostov.at 100 and 50μg/mL,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with coumarin was an effective way to novel fungicide development.
基金supported in part by the Tianjin Natural Science Foundation (No. 18JCZDJC33500)the Frontiers Science Center for New Organic Matter,Nankai University (No. 63181206)the Tianjin Development Program for Innovation and Entrepreneurship。
文摘3,4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole,a novel purine derivative,was synthesized by the cyclization of pyrimidine amine.Its structure was characterized by ^(1)H NMR,^(13)C NMR,^(19)FNMR,H RMS and single-crystal X-ray diffraction.This compound 3 is crystallized from a mixed solvent of dichloromethane and n-hexane (1:2,v/v) for structural identification as monoclinic crystal system,space group P2_(1)/n with a=11.66250(10),b=8.21300(10),c=17.77920(10)?,V=1676.34(3)?^(3),Z=4,D_(c)=1.643 g/cm^(3),F(000)=832.0 andμ=6.301 mm^(-1).22315 reflections were measured (8.43≤2θ≤158.10°),of which 3532 were unique (R_(int)=0.0311) and used in all calculations.The final R=0.0334 (I>2σ(I)) and w R=0.0842 (reflections).The title compound showed over 50%of growth inhibition against Botrytis cinereal,Cercospora arachidicola,Gibberella zeae,Rhizoctonia solani and Sclerotinia sclerotiorum at 50 mg/L,and its EC_(50) value against R.solani was 60.44μmol/L,which was active at the same level as that of positive control diflumetorim with its EC_(50) value of 60.29μmol/L and less active than YZK-C22 with its EC_(50) value of 12.32μmol/L,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with purine could be an effective way to novel fungicide development.
基金This project was co-tbunded by the Ph.D Program of Ministry of Education, China （No. 20130008110003）, and the National Natural Science Foundation of China （No. 21172254）.
文摘The novel fungicidal agents, （E）-5-[1-（2-oxo-l-oxaspiro[4,5]dec/non-3-en-3-yl）ethylidene]-2-aminoimidazolin- 4-one derivatives, were designed and synthesized in moderate to excellent yields in four steps using a-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7h exhibit 96.4%, 92.5%, 90.3% and 76.9% inhibition rates against Phytophthora capsici at the concentration of 50 μg/mL, respectively. These compounds exhibited significant fungicidal activities against S. scleotiorum and P. capsici with EC50 values of 2.56 --11.60 μg/mL, and compounds 6e and 7h exhibited weak inhibition against the spore germination of S. scleoti- orum, while the spore germination ofP. capsici was strongly inhibited by compound 7h solution. Scanning electron microscopy （SEM） and transmission electron microscopy （TEM） observation indicated that compound 7h had a significant impact on the structure and function of the hyphal cell wall ofP. capsici mycelium.
基金Supported by Bureau of Education in Guangzhou City(08C034)Educational Commission of Guangdong Province(LYM08081)~~
文摘[ Objective] The paper was to preliminarily identify the species of six actinomyeetes strains, and to determine the fungicidal activities of their fermenta- tion products. E Method ] The species of six aefinomyeetes strains were identified by morphological method, and the fungicidal activities of the fermentation products of six aetinomycetes strains were systematically determined by series of methods including mycellal growth rate inhibition method, spore germination method, potting and field test. []Result] Morphological identification results showed that six strains belonged to Streptornyces. Biological determination results indicated that the in- hibition rates of the fermentation products of six actinomycetes strains with the concentration of 500μg/nd against the mycelial growth of Fusar/um oxysporum f. sp. Vasinfeetum were all greater than 90% ; the inhibition rates against the myeelial growth of Botrytis cinerea Pers. , A/ternar/a a/zernate and Fusarium oxysporum were also greater than 80%. The inhibition rates of the fermentation products of GZ-204 and GZ-331 strains against the spore germination of Bipolaria sorokiniana and Cercospora sorghl were 97. 8% , 98.2%, 99.5% and 94.6%, respectively. Potting test showed that the protection effects of the fermentation products of GZ-204 and GZ-331 strains on wheat powdery mildew（Erysiphe graminis） were 78.8% and 87.1% , and their cure effects were 62.4% and 68.5% , respectively. Field test showed that the control effects of 200 times fermentation liquids of GZ-204 and GZ-331 strains on wheat powdery mildew were 50.5% and 69. 2%, respective- ly. [Condusion] The research provided the reference for the development of new pesticides with actinomyeetes as the resource.
文摘Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP51) and the docking results of inhibitors to the active site of the enzyme. All title compounds were first by reported. Results of preliminary biological tests showed that most of title compounds exhibited activity against the seven common pathogenic fungi. Compound 11 showed best antifungal activity with broad antifungal spectrum and proved to be more active against Cryptococcus neoformans, Candida albicans, Microsporum lanosum and Trichophyton rubrum than ketoconazole. Compounds 3, 10 and 4 also had high activities.
基金This work was financially supported by the Natural Science Foundation of Shandong Province,China(ZR2017BC053)the Doctoral Research Startup Foundation of Liaocheng University(318051625).
文摘In recent years,the damage caused by soil nematodes has become increasingly serious;however,the varieties and structures of the nematicides available on the market are deficient.Fluopyram,a succinate dehydrogenase inhibitor(SDHI)fungicide developed by Bayer AG in Germany,has been widely used in the prevention and control of soil nematodes due to its high efficiency and novel mechanism of action.In this paper,two series of novel target compounds were designed and synthesized with nematicidal and fungicidal fluopyram as the molecular skeleton in order to introduce sulfide and sulfone substructures.The structures were identified and characterized by 1H nuclear magnetic resonance(NMR),13C NMR,and high-resolution mass spectrometer(HRMS).The bioassays revealed that most of the compounds showed excellent nematicidal activities at 200 lgmL-1 in comparison with fluopyram,while the nematode mortality rate dropped sharply at 100μg·mL-1,except for compounds I-11 and II-6.In terms of fungicidal activity,compound I-9 was discovered to have an excellent inhibitory rate,and a molecular docking simulation was performed that can provide important guidance for the design and exploration of efficient fungicidal lead compounds.
基金funded in part by the NNSFC (20872071)the NSF of Tianjin (10JCZDJC17500)+3 种基金the National Key Project for Basic Research(2010CB126105)National Key Technology Research and Development Program (2011BAE06B02 and 2011BAE06B05)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (201002250)Tianjin Key Technology Research and Development Program (11ZCGYNC00100)
文摘The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.
基金We gratefully acknowledge the financial support of the Natural Science Foundation of Education Department of Hubei Province （No. 2004D001）.
文摘Abstract： Ten novel 2-alkylthio-5-（3, 4, 5-tribenzyloxyphenyl）-1, 3, 4-oxadiazole derivatives （5a-j） were synthesized from methyl 3, 4, 5-trihydroxybenzoate by ethedfication, hydrazidation, cyclization and thioetherification reactions. The structures of 5a-j were confirmed by 1HNMR, MS spectra and elemental analysis. The results indicated that most of the compounds 5 exhibited good fungicidal activities. The activity of 5h is higher than 90% against Fusarium oxysporum and Botrytis cinereapers in 50 mg/L.
基金National Natural Science Foundation of China (Nos.21732002,22077071,21977056)Frontiers Science Center for New Organic Matter,Nankai University (No.63181206)the Fundamental Research Funds for the Central Universities,Nankai University (No.63201043)。
文摘The biological activities of a series of 3,3-spirocyclic indole derivatives containing CF_(2), phosphine oxide,indole, and cyano functional groups were evaluated, and these derivatives were found to exhibit antiTMV, fungicidal, and insecticidal activities.
基金funded by the National Natural Science Foundation of China (No.21202089)the Research Foundation of the Six People Peak of Jiangsu Province (Nos.2011-SWYY-009,2013-SWYY-013)the Technology Project Fund of Nantong City (Nos.AS2013004,CP12013002)
文摘A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by 1H NMR, 13C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.
