Natural herbicides, or environment-friendly bioherbicides have been attracted more and more attentions. Isolation and structural identification of natural herbicide-active compounds from plant pathogens has been prove...Natural herbicides, or environment-friendly bioherbicides have been attracted more and more attentions. Isolation and structural identification of natural herbicide-active compounds from plant pathogens has been proved to be an effective approach for novel lead discovery of the pesticide development. In this study, the metabolites of the mutant strain PAM1, which obtained from PA1 of Pythium aphanidermatum （Eds.） Fitzp by ultraviolet radiation were separated and identified by HPLC, NMR, and IR. The results revealed that three active compounds including 4-hydroxy-3-methoxycinnamic acid and two indole derivatives, exhibited inhibition activity on the elongation of radical and coleoptile of Digtaria sanguinalis （L.） Scop.展开更多
The volatiles produced by Paenibacillus polymyxa strain BMP-11 which was isolated from the rhizosphere soil of cucumber in a greenhouse were analyzed by SPME-GC-MS.Based on the preliminary test,three kinds of purchase...The volatiles produced by Paenibacillus polymyxa strain BMP-11 which was isolated from the rhizosphere soil of cucumber in a greenhouse were analyzed by SPME-GC-MS.Based on the preliminary test,three kinds of purchased commercial products 1-octen-3-ol,benzothiazole and citronellol were chosen to give further assessment of their bioactivity.Antifungal bioassays in sealed dishes revealed that those three compounds strongly inhibited the mycelia growth of the eight pathogens at a low treatment dosage and induced the mycelial morphological abnormalities.During the experiment,we even found that citronellol completely prevented the pigment production of the tested fungus,Fusarium oxysporum,however,1-octen-3-ol and benzothiazole had slight effect.The germination was inhibited to different degrees when spores of Botrytis cinerea exposed to these compounds for 24 h in water agar plate.Furthermore,fumigation results showed that 1-octen-3-ol and benzothiazole had strong toxicity against Tribolium castaneum,LC50 was 16.76 and 3.50 mg L-1,respectively.The fumigation activity was also found similar to the positive control,1,3-dichloropropene （LC50 =10.13 mg L-1）.Results of herbicidal assays showed that tested compounds had inhibitory effects on the seed germination and seedling growth of Amaranthus retroflexus,Echinochloa crusgalli and Chenopodium album.Findings of the present study suggested that the antifungal,insecticidal and herbicidal properties of the components were contained in volatiles.These agents or even their derivatives may have a potential to be used as fungicide,insecticide as well as herbicide.展开更多
A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their...A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis （L） Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.展开更多
Three series of novel 2-cyanoacrylates 7a--7f, 9a-9f, 10a--10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II （PS II） electron transportation. Their structures...Three series of novel 2-cyanoacrylates 7a--7f, 9a-9f, 10a--10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II （PS II） electron transportation. Their structures were clearly verified by lH NMR, 13C NMR, elemental analysis （or HRMS analysis） and single-crystal X-ray diffraction analysis. Bioassay showed that a suitable group at the 3-position of acrylates was essential for high herbicidal activ- ity. In particular, compound 7e showed the best herbicidal activities and gave 100% inhibitory activity against rape and amaranth pigweed at a dose of 1.5 kg/ha. Introduction of substituent with higher polarity such as sulfinyl or sulfonyl to the 5-position of 1,3,4-thiadiazole decreased herbicidal activities.展开更多
In order to understand the compsition and structure of herbicidal component of Pythium aphanidermatum,the isolation and structural indentification were researched.The culture filtrate was extracted by ethyl acetate,pe...In order to understand the compsition and structure of herbicidal component of Pythium aphanidermatum,the isolation and structural indentification were researched.The culture filtrate was extracted by ethyl acetate,petroleum,and chloroform with the same volume respectively and the activity of the crude toxin was bioassayed.The toxin was separated by using the method of thin layer chromatography（TLC）,then the main fraction was separated by HPLC,and the structure was analyzed by the sepctrum of IR,13C-NMR and 1HNMR.The results showed that the ethyl acetate extracts had the strongest herbicidal activity.Using the method of TLC,the bioassay results showed that the extracts with Rf 0.19 had the strongest effect on weeds and the inhibition to Digitaria sanguinalis and Amaranthus retroflexus reached five levels,and the component was proved to be dimethyl o-phthalate from the spectrum of IR,13C-NMR and 1HNMR,which was one of the components from the toxin,and it had herbicidal activity.展开更多
p-Menthane type monoterpene derivatives were identified as bio-based compounds with high herbicidal activities. In order to search novel p-menthane type monoterpene derivatives in good performance, a series of novel c...p-Menthane type monoterpene derivatives were identified as bio-based compounds with high herbicidal activities. In order to search novel p-menthane type monoterpene derivatives in good performance, a series of novel cis-p-menthane type Schiff base derivatives were designed and synthesized. All target products were easily available novel compounds and characterized by FT-IR,^1H NMR,^13 C NMR and ESI＋-MS. Their pre-emergence herbicidal activities against annual ryegrass were evaluated. The bioassays indicated that most of the target compounds displayed excellent herbicidal activities in pre-emergence treatment.展开更多
Several novel 3-(substituted phenyl)isoxazole derivatives were prepared from phenyl butan-1,3-dione. Their structures were confirmed by 1H NMR, IR, and CIMS. Preliminary bioassay showed that some of them exhibited goo...Several novel 3-(substituted phenyl)isoxazole derivatives were prepared from phenyl butan-1,3-dione. Their structures were confirmed by 1H NMR, IR, and CIMS. Preliminary bioassay showed that some of them exhibited good activities toward various weeds.展开更多
With the increase of herbicide-resistant weeds, novel, more selective and even more potent herbicides to control weeds are needed. In this paper, a series of N-fluorinated phenyl-N＇-pyrimidyl urea derivatives were sy...With the increase of herbicide-resistant weeds, novel, more selective and even more potent herbicides to control weeds are needed. In this paper, a series of N-fluorinated phenyl-N＇-pyrimidyl urea derivatives were synthesized and screened for their herbicidal activities against Amaranthus retroflexus （AR） and Setaria viridis （ SV）. Compound 2S （N-（3-trifluoromethylphenyl）-N＇-（2-amino-4-chloro-6-methylpyr- imidyl） urea） exhibited marked herbicidal activity against SV（IC50 =11.67 mg/L） and is more potent than bensulfuron （IC50= 27.45 mg/L）, a commercially available herbicide. A statistically significant CoMFA model with high prediction abilities （q2 = 0.869, r2 = 0.989） was obtained.展开更多
Thirteen novel sulfonylureas containing thiadiazole moiety were synthesized in a two-step reaction. Their structures were determined using IR, ^1H NMR, HRFTMS, and elemental analysis. Herbicidal activities of these co...Thirteen novel sulfonylureas containing thiadiazole moiety were synthesized in a two-step reaction. Their structures were determined using IR, ^1H NMR, HRFTMS, and elemental analysis. Herbicidal activities of these compounds were determined in the green house bio-assay. The results show that four compounds among them exhibit some activity toward four tested herbs.展开更多
In order to find novel herbicidal active compounds, a series of N-（2,2-dimethyl-7-alkoxy-2,3-dihydro- benzofuran-5-yl）-2-（4-arylxoyphenoxy）propionamides was designed, prepared and evaluated for their herbicidal ac...In order to find novel herbicidal active compounds, a series of N-（2,2-dimethyl-7-alkoxy-2,3-dihydro- benzofuran-5-yl）-2-（4-arylxoyphenoxy）propionamides was designed, prepared and evaluated for their herbicidal activity. Bioassay results showed that most of the title compounds had excellent and selective herbicidal activity against the monocotyledonous grasses. In particular, compounds lg and lm showed 100% inhibition against the growth of three monocotyledonous grasses under both postemergence and preemergence treatments at the dose of 2250 g/hm2 （1 hm2= 104 m2）, and could be used as lead compounds for further development of novel potential herbicidal agents.展开更多
Sulfonylurea herbicides have been widely used because of their low application rates, good crop sdeetivities and low mammalian toxicities. However, some sulfonylureas might persist unfavourably in the environment with...Sulfonylurea herbicides have been widely used because of their low application rates, good crop sdeetivities and low mammalian toxicities. However, some sulfonylureas might persist unfavourably in the environment with residual problems. In order to look for ecologically safer and environmentally benign sulfonylureas, and on keeping the pyrimidine ring being monosubstitated, 15 novd C5-monosubstituted benzenesulfonylurea compounds were synthesized. The structures of all the compounds synthesized were confirmed by demental analysis and ^1H NMR. Preliminary herbicidal activities of these new sulfonylurea compounds were determined by ALS screening （ in vitro） and pot bioassay experiments（ in vivo）. The herbicidal results show that some novel sulfonylureas are comparable to commercial Foramsulfuron and Monosulfuron.展开更多
A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yie...A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yields. The crystal structure of compound 6i was determined to show a chair conformation of the piperazine ring and an （E）-configuration of the C=N double bond. The bioassay results indicated that most of the newly synthesized compounds exhibited excellent in vitro inhibitory activities and broader spectrum against several plant fungi, and were more effective than the control Triadimefon. Several compounds also displayed favourable in vivo antifungal activities. The relationships between the compound structures and various biological activities were discussed. Furthermore, the CoMFA calculation based on the antifungal activity data of compounds 6 against R. cerealis was carried out to establish a 3D-QSAR model, which revealed that steric and electrostatic fields were two most important factors for contributing the bioactivity of the compounds. The present work will provide significant information for guiding optimization of such new structures to develop novel agrochemicals with higher antifungal activities.展开更多
Two novel bis(2-hydroxy-5-R-benzylidene)carbohydrazide dibutyltin complexes(R:Cl(T1),Me(T2))with hexanuclear and triangular frame structures were obtained by microwave-assisted solvothermal reaction of dibutyltin oxid...Two novel bis(2-hydroxy-5-R-benzylidene)carbohydrazide dibutyltin complexes(R:Cl(T1),Me(T2))with hexanuclear and triangular frame structures were obtained by microwave-assisted solvothermal reaction of dibutyltin oxide precursor with the ligands in methanol environments,However,their structures are characterized by elemental analysis,IR,(1H,13C)NMR spectra,and the molecular structures of T1 and T2 were confirmed by X-ray diffraction.The crystal of T1 belongs to triclinic system,space group P1,and T2 is of monoclinic system,space group C2/c.Five-coordinated distorted triangular bipyramids and six-coordinated distorted octahedral configurations were formed by the coordination of oxygen and nitrogen atoms of ligands with two dibutyltins,respectively,and trimer hexanuclear dibutyltin complexes were constructed by the cross-coordination of enol imines.The two complexes exhibit fluorescence emission in DMF solvents and DMF-water mixtures.When the volume fraction of water content is between 0 and 10%(V/V),the aggregation fluorescence enhancement effect is good,and fluorescence quenching occurs when the water content is more than 10%(V/V).The T1 can inhibit the growth of target plants,such as Portulaca oleracea,Cassia tora L.,Brassica campestris L.ssp.chinensis var.utilis Tsen et Lee and Amaranthus tricolor L.The T2 can selectively inhibit the growth of Portulaca oleracea L.,Amaranthus spinosus L.and Amaranthus tricolor L.It can be used as a candidate herbicide for Portulaca oleracea L.,Amaranthus spinosus L.and Amaranthus tricolor L.展开更多
基金supported by the grants from the National High Technology Research and Development Program of China(2011AA10A206)the National NaturalScience Foundation of China(31171877)
文摘Natural herbicides, or environment-friendly bioherbicides have been attracted more and more attentions. Isolation and structural identification of natural herbicide-active compounds from plant pathogens has been proved to be an effective approach for novel lead discovery of the pesticide development. In this study, the metabolites of the mutant strain PAM1, which obtained from PA1 of Pythium aphanidermatum （Eds.） Fitzp by ultraviolet radiation were separated and identified by HPLC, NMR, and IR. The results revealed that three active compounds including 4-hydroxy-3-methoxycinnamic acid and two indole derivatives, exhibited inhibition activity on the elongation of radical and coleoptile of Digtaria sanguinalis （L.） Scop.
基金funded by the Special Fund for Agro-Scientific Research in the Public Internet of China(200903033)
文摘The volatiles produced by Paenibacillus polymyxa strain BMP-11 which was isolated from the rhizosphere soil of cucumber in a greenhouse were analyzed by SPME-GC-MS.Based on the preliminary test,three kinds of purchased commercial products 1-octen-3-ol,benzothiazole and citronellol were chosen to give further assessment of their bioactivity.Antifungal bioassays in sealed dishes revealed that those three compounds strongly inhibited the mycelia growth of the eight pathogens at a low treatment dosage and induced the mycelial morphological abnormalities.During the experiment,we even found that citronellol completely prevented the pigment production of the tested fungus,Fusarium oxysporum,however,1-octen-3-ol and benzothiazole had slight effect.The germination was inhibited to different degrees when spores of Botrytis cinerea exposed to these compounds for 24 h in water agar plate.Furthermore,fumigation results showed that 1-octen-3-ol and benzothiazole had strong toxicity against Tribolium castaneum,LC50 was 16.76 and 3.50 mg L-1,respectively.The fumigation activity was also found similar to the positive control,1,3-dichloropropene （LC50 =10.13 mg L-1）.Results of herbicidal assays showed that tested compounds had inhibitory effects on the seed germination and seedling growth of Amaranthus retroflexus,Echinochloa crusgalli and Chenopodium album.Findings of the present study suggested that the antifungal,insecticidal and herbicidal properties of the components were contained in volatiles.These agents or even their derivatives may have a potential to be used as fungicide,insecticide as well as herbicide.
基金financially supported by the National Natural Science Foundation of China (Nos.31171877,31571991,21372132)the International Science & Technology Cooperation Program of China (No.2014DFR41030)
文摘A series of novel N-（3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl） amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis （L） Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.
基金Project supported by the National Natural Science Foundation of China （NNSFC） （No. 20772068） and the National Key Project of Scientific and Technical Supporting Programs Funded by Ministry of Science ＆ Technology of China （No. 2006BAE01A01-5）.
文摘Three series of novel 2-cyanoacrylates 7a--7f, 9a-9f, 10a--10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II （PS II） electron transportation. Their structures were clearly verified by lH NMR, 13C NMR, elemental analysis （or HRMS analysis） and single-crystal X-ray diffraction analysis. Bioassay showed that a suitable group at the 3-position of acrylates was essential for high herbicidal activ- ity. In particular, compound 7e showed the best herbicidal activities and gave 100% inhibitory activity against rape and amaranth pigweed at a dose of 1.5 kg/ha. Introduction of substituent with higher polarity such as sulfinyl or sulfonyl to the 5-position of 1,3,4-thiadiazole decreased herbicidal activities.
基金supported by a grant from the National High Technology Research and Development Program of China (2006AA10A214)the Natural Science Foundation of Hebei Province,China (C2007000464)
文摘In order to understand the compsition and structure of herbicidal component of Pythium aphanidermatum,the isolation and structural indentification were researched.The culture filtrate was extracted by ethyl acetate,petroleum,and chloroform with the same volume respectively and the activity of the crude toxin was bioassayed.The toxin was separated by using the method of thin layer chromatography（TLC）,then the main fraction was separated by HPLC,and the structure was analyzed by the sepctrum of IR,13C-NMR and 1HNMR.The results showed that the ethyl acetate extracts had the strongest herbicidal activity.Using the method of TLC,the bioassay results showed that the extracts with Rf 0.19 had the strongest effect on weeds and the inhibition to Digitaria sanguinalis and Amaranthus retroflexus reached five levels,and the component was proved to be dimethyl o-phthalate from the spectrum of IR,13C-NMR and 1HNMR,which was one of the components from the toxin,and it had herbicidal activity.
基金funded by the Key Projects in the National Science&Technology Pillar Program during the Twelfth Five-year Plan Period(No.2015BAD15B04)the National Natural Science Foundation of China(No.31600466)the Fundamental Research Funds for Jiangsu Key Laboratory of Biomass Energy and Material(No.JSBEM-S-201605)
文摘p-Menthane type monoterpene derivatives were identified as bio-based compounds with high herbicidal activities. In order to search novel p-menthane type monoterpene derivatives in good performance, a series of novel cis-p-menthane type Schiff base derivatives were designed and synthesized. All target products were easily available novel compounds and characterized by FT-IR,^1H NMR,^13 C NMR and ESI＋-MS. Their pre-emergence herbicidal activities against annual ryegrass were evaluated. The bioassays indicated that most of the target compounds displayed excellent herbicidal activities in pre-emergence treatment.
文摘Several novel 3-(substituted phenyl)isoxazole derivatives were prepared from phenyl butan-1,3-dione. Their structures were confirmed by 1H NMR, IR, and CIMS. Preliminary bioassay showed that some of them exhibited good activities toward various weeds.
基金supported by the National Natural Science Foundation of China(No.30900935)the Fundamental Research Funds for the Central Universities(Nos.2011PY086,2011PY039)
文摘With the increase of herbicide-resistant weeds, novel, more selective and even more potent herbicides to control weeds are needed. In this paper, a series of N-fluorinated phenyl-N＇-pyrimidyl urea derivatives were synthesized and screened for their herbicidal activities against Amaranthus retroflexus （AR） and Setaria viridis （ SV）. Compound 2S （N-（3-trifluoromethylphenyl）-N＇-（2-amino-4-chloro-6-methylpyr- imidyl） urea） exhibited marked herbicidal activity against SV（IC50 =11.67 mg/L） and is more potent than bensulfuron （IC50= 27.45 mg/L）, a commercially available herbicide. A statistically significant CoMFA model with high prediction abilities （q2 = 0.869, r2 = 0.989） was obtained.
基金National Basic Research Program of China(No.2003CB11406)Key Project of National Natural Science Foucndation of China(No.20432010)
文摘Thirteen novel sulfonylureas containing thiadiazole moiety were synthesized in a two-step reaction. Their structures were determined using IR, ^1H NMR, HRFTMS, and elemental analysis. Herbicidal activities of these compounds were determined in the green house bio-assay. The results show that four compounds among them exhibit some activity toward four tested herbs.
文摘In order to find novel herbicidal active compounds, a series of N-（2,2-dimethyl-7-alkoxy-2,3-dihydro- benzofuran-5-yl）-2-（4-arylxoyphenoxy）propionamides was designed, prepared and evaluated for their herbicidal activity. Bioassay results showed that most of the title compounds had excellent and selective herbicidal activity against the monocotyledonous grasses. In particular, compounds lg and lm showed 100% inhibition against the growth of three monocotyledonous grasses under both postemergence and preemergence treatments at the dose of 2250 g/hm2 （1 hm2= 104 m2）, and could be used as lead compounds for further development of novel potential herbicidal agents.
基金Supported by the National Key Basic Research Program of China(No.2003CB114406)the National Natural Science Foundation Key Project of China(No.20432010).
文摘Sulfonylurea herbicides have been widely used because of their low application rates, good crop sdeetivities and low mammalian toxicities. However, some sulfonylureas might persist unfavourably in the environment with residual problems. In order to look for ecologically safer and environmentally benign sulfonylureas, and on keeping the pyrimidine ring being monosubstitated, 15 novd C5-monosubstituted benzenesulfonylurea compounds were synthesized. The structures of all the compounds synthesized were confirmed by demental analysis and ^1H NMR. Preliminary herbicidal activities of these new sulfonylurea compounds were determined by ALS screening （ in vitro） and pot bioassay experiments（ in vivo）. The herbicidal results show that some novel sulfonylureas are comparable to commercial Foramsulfuron and Monosulfuron.
基金supported by the National Natural Science Foundation of China(No. 21372133)Tianjin Natural Science Foundation(No. 17JCYBJC19900)
文摘A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yields. The crystal structure of compound 6i was determined to show a chair conformation of the piperazine ring and an （E）-configuration of the C=N double bond. The bioassay results indicated that most of the newly synthesized compounds exhibited excellent in vitro inhibitory activities and broader spectrum against several plant fungi, and were more effective than the control Triadimefon. Several compounds also displayed favourable in vivo antifungal activities. The relationships between the compound structures and various biological activities were discussed. Furthermore, the CoMFA calculation based on the antifungal activity data of compounds 6 against R. cerealis was carried out to establish a 3D-QSAR model, which revealed that steric and electrostatic fields were two most important factors for contributing the bioactivity of the compounds. The present work will provide significant information for guiding optimization of such new structures to develop novel agrochemicals with higher antifungal activities.
基金Supported by the Innovation Platform Open Foundation for Colleges and Universities of Hunan Province(No.16k011)the Foundation of Key Laboratory of Functional Metal-organic Compounds of Hunan Province。
文摘Two novel bis(2-hydroxy-5-R-benzylidene)carbohydrazide dibutyltin complexes(R:Cl(T1),Me(T2))with hexanuclear and triangular frame structures were obtained by microwave-assisted solvothermal reaction of dibutyltin oxide precursor with the ligands in methanol environments,However,their structures are characterized by elemental analysis,IR,(1H,13C)NMR spectra,and the molecular structures of T1 and T2 were confirmed by X-ray diffraction.The crystal of T1 belongs to triclinic system,space group P1,and T2 is of monoclinic system,space group C2/c.Five-coordinated distorted triangular bipyramids and six-coordinated distorted octahedral configurations were formed by the coordination of oxygen and nitrogen atoms of ligands with two dibutyltins,respectively,and trimer hexanuclear dibutyltin complexes were constructed by the cross-coordination of enol imines.The two complexes exhibit fluorescence emission in DMF solvents and DMF-water mixtures.When the volume fraction of water content is between 0 and 10%(V/V),the aggregation fluorescence enhancement effect is good,and fluorescence quenching occurs when the water content is more than 10%(V/V).The T1 can inhibit the growth of target plants,such as Portulaca oleracea,Cassia tora L.,Brassica campestris L.ssp.chinensis var.utilis Tsen et Lee and Amaranthus tricolor L.The T2 can selectively inhibit the growth of Portulaca oleracea L.,Amaranthus spinosus L.and Amaranthus tricolor L.It can be used as a candidate herbicide for Portulaca oleracea L.,Amaranthus spinosus L.and Amaranthus tricolor L.
