- Synthesis and fungicidal activity of (E)-α-(Methoxyimino)benzeneacetate derivatives containing 1,2,4-triazole schiff base side Chain
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Figure presented To find new strobilurin analogs with high activity against resistant pathogens, twelve (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,2,4-triazole Schiff base side chain 3a-3l were designed and synthesized. Their structures were confirmed by IR, 1H-NMR, EIMS, and elemental analyses. Bioassays indicated that most of the target compounds showed moderate to good fungicidal activities against Physalospora piricola Nose and Alternaria solani. For example, compounds 3d, 3e, and 3f possessed 99.5%, 100%, and 95.6% inhibition against Physalospora piricola Nose, whereas compounds 3d, 3f, and 3g exhibited 92%, 91%, and 92% inhibition against Alternaria solani at the concentration of 50 mg/L, respectively.
- Song, Hong-Xing,Shi, De-Qing
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- Preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and intermediate thereof
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The invention provides a preparation method of (E)-2-methyl-alpha-methoxyimino methyl phenylacetate and an intermediate thereof, and the intermediate 2-methyl-alpha-hydroxyimino phenylacetic acid is prepared by taking 2-methyl-alpha-hydroxyimino phenylace
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Paragraph 0080-0107
(2021/05/29)
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- Intermediate for preparing trifloxystrobin and synthesis method of intermediate
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The invention relates to an intermediate for preparing trifloxystrobin and a synthesis method of the intermediate, wherein the synthesis method comprises the steps: by taking 2-oxime-o-methyl phenylacetonitrile as a raw material, heating and hydrolyzing i
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Paragraph 0066; 0072; 0073
(2020/11/01)
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- (E)-2-(2-tolyl)-2-methoxyimino methyl acetate preparation method
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The invention provides a (E)-2-(2-tolyl)-2-methoxyimino methyl acetate preparation method, which comprises: carrying out a saponification reaction on (Z)-2-(2-tolyl)-2-methoxyimino methyl acetate or (E/Z)-2-(2-tolyl)-2-methoxyimino methyl acetate or a mother liquor containing (E/Z)-2-(2-tolyl)-2-methoxyimino methyl acetate and an alkali to obtain (E)-2-(2-tolyl)-2-methoxyimino acetic acid, and carrying out a reaction on the obtained (E)-2-(2-tolyl)-2-methoxyimino acetic acid and a methylation reagent under an alkaline condition to obtain (E)-2-(2-tolyl)-2-methoxyimino methyl acetate. Accordingto the method disclosed by the invention, the Z configuration is converted into the E configuration product, so that the yield of the obtained E configuration product is obviously improved, the corrosion to equipment is small, the environmental pollution is not easily caused, and the method is an environment-friendly chemical synthesis process.
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- Green synthetic method of kresoxim-methyl
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The invention belongs to the technical field of fine chemical engineering, and particularly relates to a green synthetic method of kresoxim-methyl. The method comprises the following steps: carrying out nitrous nitrification by using 2-methylbenzyl cyanide as an initial raw material, carrying out methylation, carrying out hydrolytic methylation or hydrolytic esterification, carrying out bromination and carrying out an etherification reaction to obtain the high-content kresoxim-methyl. The method provided by the invention has a short reaction period, a high conversion rate, and excellent product quality, changes the defect that high-concentration hydrochloric acid gas is used for preparation in a traditional process, and has the advantages of simple operation steps, simple equipment, low energy consumption, a short period, high productivity and environmental protection.
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Paragraph 0062; 0067; 0068
(2019/11/13)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN
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The present invention relates to an improved process for the preparation of trifloxystrobin of formula (I), which is simple, economical, efficient, user and environment friendly, moreover commercially viable with higher yield and chemical purity.
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- Preparation method for methyl (E)-2-methoxyimino-2-(o-methylphenyl) acetate
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The invention belongs to the field of chemical synthesis, in particular to a preparation method for the methyl (E)-2-methoxyimino-2-(o-methylphenyl) acetate. The method comprises the following steps:in the presence of a catalyst, making a compound shown in a formula (I) and a compound show as a formula (II) react to obtain the methyl (E)-2-methoxyimino-2-(o-methylphenyl) acetate; in the formula (I), X is selected from Cl, Br, -I, -OTs, -OMs or -OTf. The preparation method provided by the invention has the advantages of low-cost and readily-available raw materials, low production cost, short synthesis route, simple process and high yield; meanwhile no extremely toxic substances are used in the preparation process of raw materials, injury on people and damage to environment are lowered, sothat the preparation method can meet the requirement on environment-friendly development. The formulas are shown in the description.
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- Synthesis and evaluation of essential oil-derived β-methoxyacrylate derivatives as high potential fungicides
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Essential oils (EOs) are plant-derived aroma compounds with a wide range of biological activity, but their actions are slow, and they are typically unstable to light or heat, difficult to extract and so on. To find highly potential fungicides derived from natural EOs, a series of essential oil-based β-methoxyacrylate derivatives have been designed and synthesized. The target compounds have been screened for their potential fungicidal activity against eleven species of plant pathogen fungi, including Alternaria alternata, Phomopsis adianticola, Pestalotiopsis theae, Sclerotinia sclerotiorum, etc. Compared with intermediates I, the parent essential oils and azoxystrobin, almost all of essential oil-based β-methoxyacrylate derivatives exhibited significantly better fungicidal activity. Further investigation revealed that some compounds showed remarkable inhibitory activities against Pestalotiopsis theae, Phomopsis adianticola, Sclerotinia sclerotiorum and Magnapothe grisea at different concentrations in contrast to the commercial product azoxystrobin. Compound II-8 exhibited particularly significant fungicidal activity.
- Su, Haihuan,Wang, Wenda,Bao, Longzhu,Wang, Shuangshuang,Cao, Xiufang
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- A NOVEL PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN
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The present invention relates to a novel process for preparation of methyl (αE)-(α- (methoxyimino)-2-[[[(E)-[1-[3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzeneaceate (Trifloxystrobin) compound of formula (I) in free form or in agro chemically acceptable salt form useful as a pest control agent.The present invention also relates to a novel process for preparation of methyl (2E)-[2-(bromomethyl) phenyl] (methoxyimino) ethanoate of formula (X) intermediate of Trifloxystrobin. [Formula should be inserted here].
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- Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells
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We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60–0.94?μM. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1α protein.
- Lee, Sanghyuck,Kwon, Oh Seok,Lee, Chang-Soo,Won, Misun,Ban, Hyun Seung,Ra, Choon Sup
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p. 3026 - 3029
(2017/05/31)
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- Synthesis and fungicidal activity of novel chloro-containing 1-Aryl-3-oxypyrazoles with an oximino ester or oximino amide moiety
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Six novel chloro-containing 1-aryl-3-oxypyrazoles TMa-TMf with an oximino ester or an oximino amide moiety were prepared by the reaction of 1-aryl-1H-pyrazol-3-ols with benzyl bromide. Their structures were characterized by 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. A preliminary in vitro bioassay indicated that compounds TMa, TMe and TMf displayed excellent fungicidal activity against Rhizoctonia solani and could be used as potential lead compounds for further development of novel fungicides.
- Liu, Yuanyuan,Li, Yi,Chen, Nanqing,Lv, Kunzhi,Zhou, Chao,Xiong, Xiaohui,Li, Fangshi
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p. 8140 - 8150
(2014/07/08)
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- AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL
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The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.
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Page/Page column 28; 30; 31
(2013/10/21)
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- METHOXYIMINO COMPOUNDS AND FUNGICIDE COMPOSITION COMPRISING SAME
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The present invention provides a methoxyimino compound, and a fungicide composition comprising same as an active ingredient. The methoxyimino compound of the present invention, which has an excellent antifungal activity against a wide spectrum of fungi even at a low application rate, can be used to protect various crops.
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Page/Page column 15-16
(2009/07/17)
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- Stereoselective synthesis and antifungal activities of (E)-α- (methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring
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Thirteen novel (E)-α-(methoxyimino)benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of the methyl (E)-methoxyiminoacetate moiety and 1,3,5-substituted pyrazole ring, were stereoselectively synthesized. It was found that the coupling reaction could give stereoselectively (E:Z ca. 14:1) the key intermediate material (E)-methyl 2-(hydroxyimino)-2-o-tolyl acetate (2). An X-ray crystallographic structure determination was carried out in a representative product. The preliminary bioassays indicated that all of the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola, and Bipolaris mayclis.
- Li, Yan,Zhang, Hong-Quan,Liu, Jie,Yang, Xiang-Ping,Liu, Zhao-Jie
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p. 3636 - 3640
(2007/10/03)
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- Stereoselective synthesis and fungicidal activities of (E)-α- (methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring
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Fifteen novel (E)-α-(methoxyimino)-benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of (E)-methyl methoxyiminoacetate moiety and 1,3,4-oxadiazole ring were stereoselectively synthesized. It was first found that the coupling reaction could give stereoselectively the key intermediate (E) and (Z)-methyl 2-(hydroxyimino)-2-o-tolylacetate 2 with a ratio of 14:1. The preliminary bioassays indicated that all the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola and Bipolaris mayclis, and all of the tested compounds 1a-1o had more potent fungicidal activities against R. solani than Kresoxim-methyl.
- Li, Yan,Liu, Jie,Zhang, Hongquan,Yang, Xiangping,Liu, Zhaojie
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p. 2278 - 2282
(2007/10/03)
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- Acrylate fungicides
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Compounds of formula I STR1 wherein X is oxygen or sulphur, W is CH or N, m is 0 or 1, and either a) n is 1 and Q is a non-aromatic heterocyclic ring of 3 to 10 ring atoms, containing one to three hetero atoms selected from oxygen, sulphur and nitrogen, which may be substituted and may be fused to another ring, with the proviso a) that if Q is thiazol-2-in-2-yl, it is substituted but not by methylene, and b) Q is not a six membered ring containing only two nitrogen atoms, or b) n is 0 or 1 and STR2 where R1 is alkyl, alkoxy or alkylthio, and R2 is heteroaryl, non aromatic heterocyclyl, optionally substituted cycloalkyl or optionally substituted alkyl containing at least 5 carbon atoms, phenyl substituted by one or more groups selected from halogen, optionally substituted alkyl, alkoxy, haloalkoxy, aryloxy, alkylthio and alkoxycarbonyl, and when R1 is alkyl or alkoxy, or, when W is nitrogen, R2 can also be unsubstituted phenyl, have pesticidal especially fungicidal activity.
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- Acrylate fungicides
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The invention provides compounds of formula I STR1 wherein W, D, R1, R2, R3, x, m, n and p are as defined in the description. The compound have valuable pesticidal activity especially against fungi, insects, nematodes, aca
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