3-氨基-6-甲基吡啶-2(1H)-酮 | 43029-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-氨基-6-甲基吡啶-2(1H)-酮
• 英文名称: 3-amino-6-methyl-2(1H)-pyrazinone
• 英文别名: 3-amino-6-methyl-1H-pyrazin-2-one；3-Amino-6-methyl-1H-pyrazin-2-on；3-amino-6-methylpyrazin-2-one；3-Amino-6-methylpyrazin-2(1H)-one；3-amino-6-methyl-1H-pyrazin-2-one
• CAS: 43029-20-5
• 化学式: C₅H₇N₃O
• mdl: MFCD19216347
• 分子量: 125.13
• InChiKey: YVGTVIOWXKGPRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基-6-甲基吡啶-2(1H)-酮 在 sodium hydroxide 、 硫酸二甲酯 作用下， 生成 3-amino-1,6-dimethylpyrazin-2-one
  参考文献：
  名称：

  Aminopyrazinones and aminotriazinones

  摘要：

  Aminopyrazinones和aminotriazinones的化学式为##STR1##，以及这些化合物与胺、碱金属或碱土金属碱或季铵盐的盐具有良好的前后除草和生长调节性能。在这个化学式中，E是氮或.dbd.CR.sup.4 --，R.sup.1是C.sub.1 -C.sub.4 -烷基，R.sup.2是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.1 -C.sub.3 -烷基亚硫醇、C.sub.1 -C.sub.2 -氧烷氧基、C.sub.1 -C.sub.3 -烷基磺酰基、卤素或--NR.sup.5 R.sup.6，R.sup.3是氢或C.sub.1 -C.sub.3 -烷基，Q是一个基团##STR2##，其中R.sup.4是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、环丙基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.2 -C.sub.4 -氧烷基、C.sub.3 -C.sub.5 -二烷氧甲基、卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地是氢或C.sub.1 -C.sub.3 -烷基，X是氧或硫，A是一个基团##STR3##，其中Y是氧、硫、--CH.dbd.CH--、--NR.sup.9 --或--CR.sup.10 .dbd.N--，R.sup.7是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基或三氟甲基，R.sup.8是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基、--C.dbd.CH，或以下基团之一##STR4##，R.sup.9和R.sup.10彼此独立地是氢、C.sub.1 -C.sub.3 -烷基或C.sub.2 -C.sub.4 -烯基，R.sup.11是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.3 -C.sub.6 -环烷基或C.sub.2 -C.sub.4 -氧烷基，R.sup.12是C.sub.1 -C.sub.6 -氧烷基、C.sub.3 -C.sub.6 -烯氧基、C.sub.3 -C.sub.6 -炔氧基、C.sub.2 -C.sub.6 -卤代氧烷基、C.sub.1 -C.sub.4 -氰基氧烷基、C.sub.1 -C.sub.6 -硫烷基、C.sub.3 -C.sub.6 -烯基硫、C.sub.3 -C.sub.6 -炔基硫、C.sub.5 -C.sub.6 -环烷氧基、C.sub.2 -C.sub.6 -氧烷氧基或--NR.sup.16 R.sup.17，R.sup.13是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.14是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.15是C.sub.3 -C.sub.6 -炔基、C.sub.2 -C.sub.6 -烯基、C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.4 -卤代烷基、C.sub. 2 -C.sub.4 -卤代烯基或C.sub.1 -C.sub.4 -烷基，通过氰基、甲氧基、乙氧基、硝基、C.sub.1 -C.sub.4 -氧基羰基、甲硫基、乙硫基、甲基磺酰基或乙基磺酰基取代；或通过硝基、氰基、甲氧基或乙氧基取代的C.sub.3 -C.sub.4 -烯基，R.sup.16是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.17是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.18是C.sub.1 -C.sub.3 -烷基和C.sub.1 -C.sub.3 -卤代烷基，W是氧或硫，Z是氧、硫、--SO--或--SO.sub.2 --，m是数字零或一。

  公开号：

  US04795486A1
• 作为产物：
  描述：

  3,4-二氢-5-甲基-3-氧代-吡嗪羧酰胺(9ci) 在 sodium hydroxide 、 溴 作用下， 生成 3-氨基-6-甲基吡啶-2(1H)-酮
  参考文献：
  名称：

  Metabolite Analogs. V. Preparation of Some Substituted Pyrazines and Imidazo [b]pyrazines

  摘要：

  DOI：

  10.1021/ja01582a066

文献信息

• Studies on Pyrazines; Part 30:¹Synthesis of Aminopyrazines from Azidopyrazines
  作者：Nobuhiro Sato、Tomoyuki Matsuura、Naoko Miwa

  DOI：10.1055/s-1994-25607

  日期：——

  Azidopyrazines do not undergo reduction by reagents that are effective for the preparation of alkyl- or arylamines from the azides because the heterocyclic azides exist in the bicyclic form of tetrazolo[1,5-a]pyrazines. Nevertheless, the conversion into aminopyrazines was achieved by hydrogenolysis in the presence of ammonium hydroxide and palladium-on-carbon or particularly by reduction with tin(II) chloride in methanolic hydrochloric acid, in 34-87% yields. To elucidate the successful progress of the reaction, the equilibrium of azide-tetrazole was examined by 1H NMR spectroscopy in various solvents.

  叠氮吡嗪不能通过有效制备烷基或芳基胺的试剂进行还原，因为杂环叠氮化物以双环形式存在于四唑[1,5-a]吡嗪中。然而，通过在氨 hydroxide 和钯-炭存在下进行加氢裂解，或通过在醇溶盐酸中用氯化锡(II)还原，成功转化为氨基吡嗪，产率为34-87%。为了阐明反应的成功进展，通过1H NMR光谱在不同溶剂中检查了叠氮-四唑的平衡。
• Aminopyrazinones and aminotriazinones
  申请人：——

  公开号：US04795486A1

  公开（公告）日：1989-01-03

  Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl, halogen or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, --NR.sup.9 -- or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro, --C.dbd.CH, or one of the groups ##STR4## R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub. 2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO.sub.2 -- and m is the number zero or one.

  Aminopyrazinones和aminotriazinones的化学式为##STR1##，以及这些化合物与胺、碱金属或碱土金属碱或季铵盐的盐具有良好的前后除草和生长调节性能。在这个化学式中，E是氮或.dbd.CR.sup.4 --，R.sup.1是C.sub.1 -C.sub.4 -烷基，R.sup.2是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.1 -C.sub.3 -烷基亚硫醇、C.sub.1 -C.sub.2 -氧烷氧基、C.sub.1 -C.sub.3 -烷基磺酰基、卤素或--NR.sup.5 R.sup.6，R.sup.3是氢或C.sub.1 -C.sub.3 -烷基，Q是一个基团##STR2##，其中R.sup.4是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、环丙基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.2 -C.sub.4 -氧烷基、C.sub.3 -C.sub.5 -二烷氧甲基、卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地是氢或C.sub.1 -C.sub.3 -烷基，X是氧或硫，A是一个基团##STR3##，其中Y是氧、硫、--CH.dbd.CH--、--NR.sup.9 --或--CR.sup.10 .dbd.N--，R.sup.7是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基或三氟甲基，R.sup.8是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基、--C.dbd.CH，或以下基团之一##STR4##，R.sup.9和R.sup.10彼此独立地是氢、C.sub.1 -C.sub.3 -烷基或C.sub.2 -C.sub.4 -烯基，R.sup.11是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.3 -C.sub.6 -环烷基或C.sub.2 -C.sub.4 -氧烷基，R.sup.12是C.sub.1 -C.sub.6 -氧烷基、C.sub.3 -C.sub.6 -烯氧基、C.sub.3 -C.sub.6 -炔氧基、C.sub.2 -C.sub.6 -卤代氧烷基、C.sub.1 -C.sub.4 -氰基氧烷基、C.sub.1 -C.sub.6 -硫烷基、C.sub.3 -C.sub.6 -烯基硫、C.sub.3 -C.sub.6 -炔基硫、C.sub.5 -C.sub.6 -环烷氧基、C.sub.2 -C.sub.6 -氧烷氧基或--NR.sup.16 R.sup.17，R.sup.13是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.14是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.15是C.sub.3 -C.sub.6 -炔基、C.sub.2 -C.sub.6 -烯基、C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.4 -卤代烷基、C.sub. 2 -C.sub.4 -卤代烯基或C.sub.1 -C.sub.4 -烷基，通过氰基、甲氧基、乙氧基、硝基、C.sub.1 -C.sub.4 -氧基羰基、甲硫基、乙硫基、甲基磺酰基或乙基磺酰基取代；或通过硝基、氰基、甲氧基或乙氧基取代的C.sub.3 -C.sub.4 -烯基，R.sup.16是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.17是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.18是C.sub.1 -C.sub.3 -烷基和C.sub.1 -C.sub.3 -卤代烷基，W是氧或硫，Z是氧、硫、--SO--或--SO.sub.2 --，m是数字零或一。
• Aminopyrazinones
  申请人：Ciba-Geigy Corporation

  公开号：US04871853A1

  公开（公告）日：1989-10-03

  Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl, halogen or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, -- NR.sup.9 --or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl C.sub.1 -C.sub.3 -alkoxy, nirtro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro --C.tbd.CH, or one of the groups R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl,C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub. 4 -halogenoalkyl, C.sub.2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO.sub.2 -- and m is the number zero or one.

  式为##STR1##的氨基吡嗪酮和氨基三嗪酮以及这些化合物与胺、碱金属或碱土金属碱或季铵碱的盐具有良好的前、后除草和生长调节性能。在这个式子中，E是氮或.dbd.CR.sup.4 --，R.sup.1是C.sub.1-C.sub.4-烷基，R.sup.2是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.1-C.sub.3-烷氧基、C.sub.1-C.sub.3-卤代烷氧基、C.sub.1-C.sub.3-烷基硫基、C.sub.1-C.sub.3-烷基亚砜基、C.sub.1-C.sub.2-烷氧基乙氧基、C.sub.1-C.sub.3-烷基磺酰基、卤素或--NR.sup.5 R.sup.6，R.sup.3是氢或C.sub.1-C.sub.3-烷基，Q是一个基团##STR2##其中R.sup.4是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.1-C.sub.3-烷氧基、环丙基、C.sub.1-C.sub.3-卤代烷氧基、C.sub.1-C.sub.3-烷基硫基、C.sub.2-C.sub.4-烷氧基烷基、C.sub.3-C.sub.5-二烷氧甲基、卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地是氢或C.sub.1-C.sub.3-烷基，X是氧或硫，A是一个基团##STR3##其中Y是氧、硫、--CH.dbd.CH--、--NR.sup.9--或--CR.sup.10.dbd.N--，R.sup.7是氢、卤素、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-烷氧基、硝基或三氟甲基，R.sup.8是氢、卤素、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-烷氧基、硝基、--C.tbd.CH或其中之一R.sup.9和R.sup.10独立地是氢、C.sub.1-C.sub.3-烷基或C.sub.2-C.sub.4-烯基，R.sup.11是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.3-C.sub.6-环烷基或C.sub.2-C.sub.4-烷氧基烷基，R.sup.12是C.sub.1-C.sub.6-烷氧基、C.sub.3-C.sub.6-烯氧基、C.sub.3-C.sub.6-炔氧基、C.sub.2-C.sub.6-卤代烷氧基、C.sub.1-C.sub.4-氰基烷氧基、C.sub.1-C.sub.6-烷基硫氧基、C.sub.3-C.sub.6-烯基硫氧基、C.sub.3-C.sub.6-炔基硫氧基、C.sub.5-C.sub.6-环烷氧基、C.sub.2-C.sub.6-烷氧基烷氧基或--NR.sup.16 R.sup.17，R.sup.13是氢、C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.14是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.15是C.sub.3-C.sub.6-炔基、C.sub.2-C.sub.6-烯基、C.sub.1-C.sub.6-烷基、C.sub.1-C.sub.4-卤代烷基、C.sub.2-C.sub.4-卤代烯基或C.sub.1-C.sub.4-烷基，通过氰基、甲氧基、乙氧基、硝基、C.sub.1-C.sub.4-烷氧羰基、甲硫基、乙硫基、甲磺酰基或乙磺酰基取代；或C.sub.3-C.sub.4-烯基通过硝基、氰基、甲氧基或乙氧基取代，R.sup.16是氢、C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.17是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.18是C.sub.1-C.sub.3-烷基和C.sub.1-C.sub.3-卤代烷基，W是氧或硫，Z是氧、硫、--SO--或--SO.sub.2--，m是数字零或一。
• Metabolite Analogs. V. Preparation of Some Substituted Pyrazines and Imidazo [b]pyrazines
  作者：Frank L. Muehlmann、Allan R. Day

  DOI：10.1021/ja01582a066

  日期：1956.1
• Aminopyrazinones and aminotriazinones of the formula
  申请人：Ciba-Geigy Corporation

  公开号：US04940482A1

  公开（公告）日：1990-07-10

  Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub. 1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, --NR.sup.9 -- or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub. 1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub. 1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro, --C.tbd.CH, or one of the groups ##STR4## R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub. 3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halo-genoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --So.sub.2 -- and m is the number zero or one.

  公式为##STR1##的氨基吡唑酮和氨基三唑酮以及这些化合物与胺、碱金属或碱土金属基或季铵基的盐具有良好的选择性除草和生长调节性能。 在此公式中，E为.dbd.CR.sup.4 --，R.sup.1为C.sub.1-C.sub.4-烷基，R.sup.2为C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-卤代烷基，C.sub.1-C.sub.3-烷氧基，C.sub.1-C.sub.3-卤代烷氧基，C.sub.1-C.sub.3-烷基硫基，C.sub.1-C.sub.3-烷基亚砜基，C.sub.1-C.sub.2-烷氧基乙氧基，C.sub.1-C.sub.3-烷基磺酰基或--NR.sup.5 R.sup.6，R.sup.3为氢或C.sub.1-C.sub.3-烷基，Q是一个基团##STR2##其中R.sup.4为氢，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-卤代烷基，C.sub.1-C.sub.3-烷氧基，环丙基，C.sub.1-C.sub.3-卤代烷氧基，C.sub.1-C.sub.3-烷基硫基，C.sub.2-C.sub.4-烷氧基烷基，C.sub.3-C.sub.5-二烷氧甲基，卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地为氢或C.sub.1-C.sub.3-烷基，X为氧或硫，A是一个基团##STR3##其中Y为氧，硫，--CH.dbd.CH--，--NR.sup.9--或--CR.sup.10.dbd.N--，R.sup.7为氢，卤素，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-烷氧基，硝基或三氟甲基，R.sup.8为氢，卤素，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-烷氧基，硝基，--C.tbd.CH或以下之一的基团之一##STR4##R.sup.9和R.sup.10彼此独立地为氢，C.sub.1-C.sub.3-烷基或C.sub.2-C.sub.4-烯基，R.sup.11为氢，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-卤代烷基，C.sub.3-C.sub.6-环烷基或C.sub.2-C.sub.4-烷氧基烷基，R.sup.12为C.sub.1-C.sub.6-烷氧基，C.sub.3-C.sub.6-烯氧基，C.sub.3-C.sub.6-炔氧基，C.sub.2-C.sub.6-卤代烷氧基，C.sub.1-C.sub.4-氰基烷氧基，C.sub.1-C.sub.6-烷基硫基，C.sub.3-C.sub.6-烯基硫基，C.sub.3-C.sub.6-烷基硫基，C.sub.5-C.sub.6-环烷氧基，C.sub.2-C.sub.6-烷氧基烷氧基或--NR.sup.16 R.sup.17，R.sup.13为氢，C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.14为氢，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.15为C.sub.3-C.sub.6-炔基，C.sub.2-C.sub.6-烯基，C.sub.1-C.sub.6-烷基，C.sub.1-C.sub.4-卤代烷基，C.sub.2-C.sub.4-卤代烯基或C.sub.1-C.sub.4-烷基，通过氰基，甲氧基，乙氧基，硝基，C.sub.1-C.sub.4-烷氧羰基，甲硫基，乙硫基，甲基磺酰基或乙基磺酰基取代;或通过硝基，氰基，甲氧基或乙氧基取代的C.sub.3-C.sub.4-烯基，R.sup.16为氢，C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.17为氢，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.18为C.sub.1-C.sub.3-烷基和C.sub.1-C.sub.3-卤代烷基，W为氧或硫，Z为氧，硫，--SO--或--SO.sub.2--，m为数字零或一。