3-Isopropylisoxazole-4,5-dicarboxylic acid 4-methyl ester | 170865-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Isopropylisoxazole-4,5-dicarboxylic acid 4-methyl ester
• 英文别名: 4-methoxycarbonyl-3-propan-2-yl-1,2-oxazole-5-carboxylic acid
• CAS: 170865-15-3
• 化学式: C₉H₁₁NO₅
• 分子量: 213.19
• InChiKey: YTKLQBYTVPPFHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Isopropylisoxazole-4,5-dicarboxylic acid 4-methyl ester 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 3-Isopropyl-5-methylcarbamoyl-isoxazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives

  摘要：

  AbstractStarting from bulk chemicals, novel isoxazoledicarboxylic acid esters were prepared and converted to the corresponding dicarboxylic acid mono‐amides in a few reaction steps and in high overall yields. Key intermediates for the cycloaddition step were chlorooximinoacetates or amides as nitrile oxide equivalents, prepared in one‐pot reactions from diketene or acetoacetic acid esters. Isoxazoledicarboxylic acid monoamides combined good herbicidal activity with chemical flexibility. They were characterized as inhibitors of photosynthesis. Particularly, they affected the photosynthetic electron transport in photosystem II and the rate of carbon dioxide assimilation. Applied post‐emergence, the new compounds were found to control a broad spectrum of key weeds in corn. Excellent activity was found on Abutilon theophrasti (L.) Medik., Amaranthus retroflexus L., Chenopodium album L., Ipomoea spp., Polygonum persicaria L., Solanum nigrum L. and Xanthium strumarium L. with rates between 0.2 and 0.5 kg ha−1. As a side‐effect, the compounds also showed activity against grass weeds. The compounds are excellent tank‐mix partners, e.g. for sulfonyl‐ureas, to complete the weed spectrum (Chenopodium album L., Solanum nigrum L.) and/or to reduce the risk of developing herbicide‐resistant weeds.

  DOI：

  10.1002/ps.2780440104
• 作为产物：
  描述：

  1,4-dimethyl but-2-enedioate 在 sodium hydroxide 、 sodium hypochlorite 作用下， 生成 3-Isopropylisoxazole-4,5-dicarboxylic acid 4-methyl ester
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives

  摘要：

  AbstractStarting from bulk chemicals, novel isoxazoledicarboxylic acid esters were prepared and converted to the corresponding dicarboxylic acid mono‐amides in a few reaction steps and in high overall yields. Key intermediates for the cycloaddition step were chlorooximinoacetates or amides as nitrile oxide equivalents, prepared in one‐pot reactions from diketene or acetoacetic acid esters. Isoxazoledicarboxylic acid monoamides combined good herbicidal activity with chemical flexibility. They were characterized as inhibitors of photosynthesis. Particularly, they affected the photosynthetic electron transport in photosystem II and the rate of carbon dioxide assimilation. Applied post‐emergence, the new compounds were found to control a broad spectrum of key weeds in corn. Excellent activity was found on Abutilon theophrasti (L.) Medik., Amaranthus retroflexus L., Chenopodium album L., Ipomoea spp., Polygonum persicaria L., Solanum nigrum L. and Xanthium strumarium L. with rates between 0.2 and 0.5 kg ha−1. As a side‐effect, the compounds also showed activity against grass weeds. The compounds are excellent tank‐mix partners, e.g. for sulfonyl‐ureas, to complete the weed spectrum (Chenopodium album L., Solanum nigrum L.) and/or to reduce the risk of developing herbicide‐resistant weeds.

  DOI：

  10.1002/ps.2780440104

文献信息

• Cyanoisoxazoles
  申请人：BASF Aktiengesellschaft

  公开号：US05543416A1

  公开（公告）日：1996-08-06

  Cyanoisoxazoles of the formula Ia or Ib ##STR1## where R.sup.1 is hydrogen, alkyl, cycloalkyl, phenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl and R.sup.3 is alkoxy, alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl or phenyl, it being possible for the organic radicals mentioned under R.sup.1, R.sup.2 and R.sup.3 to be substituted in each case. The compounds of the Formula Ia or Ib are useful as herbicides.

  公式Ia或Ib的氰基异噁唑化合物##STR1##其中，R.sup.1为氢，烷基，环烷基，苯基；R.sup.2为氢，烷基，环烷基，R.sup.3为烷氧基，烷基，环烷基，环烯基，烯基，炔基或苯基，R.sup.1，R.sup.2和R.sup.3下所提到的有机基团在每种情况下均可被取代。公式Ia或Ib的化合物可用作除草剂。
• US5543416A
  申请人：——

  公开号：US5543416A

  公开（公告）日：1996-08-06