Search

CN-121991062-A - Pyridopyrimidine diketone compound containing isoxazole unit and preparation method and application thereof

CN121991062ACN 121991062 ACN121991062 ACN 121991062ACN-121991062-A

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a preparation method and application of pyridopyrimidine diketones containing isoxazole units, wherein the compounds are shown in a general formula I, X independently represents O or S, and R 1 independently represents hydrogen, methyl and the like. R 2 independently represents aryl, heterocyclic group and the like, and the compound has excellent control effect on pests such as pea aphid, brown planthopper, bemisia tabaci and the like.

Inventors

  • ZHANG JIAN
  • LI QING
  • SONG BAOAN
  • HU DEYU
  • Peng Yanqun
  • ZHANG LUOMAN
  • WU ZENGXUE

Assignees

  • 贵州大学

Dates

Publication Date
20260508
Application Date
20251215

Claims (10)

  1. 1. A pyridopyrimidine dione compound containing isoxazole units or a stereoisomer thereof, or a salt thereof or a solvate thereof, characterized by the general formula I: (I); Wherein R 1 is independently selected from one or more of hydrogen, deuterium, halogen, nitro, hydroxy, amino, mercapto, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl; R 2 is independently selected from one of hydrogen, deuterium, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl; x independently represents O or S.
  2. 2. The pyridopyrimidine dione compound containing isoxazole units, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, as claimed in claim 1, wherein: R 1 is independently selected from one or more of hydrogen, deuterium, halogen, nitro, hydroxy, amino, mercapto, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl; R 2 is independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C 1 -C 6 alkyl, C 1 -C 6 alkenyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl; X independently represents O or S; The substitution refers to an alkyl group optionally substituted with halogen, nitro, hydroxy, amino, mercapto, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkenyl, cyano, C 1 -C 6 haloalkyl.
  3. 3. The pyridopyrimidine dione compound containing isoxazole units, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, as claimed in claim 1, wherein: R 1 is independently selected from one or more of hydrogen, deuterium, halogen, nitro, hydroxy, amino, mercapto, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, isobutyl, phenyl, benzyl, pyridyl; R 2 is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, isobutyl, phenyl, benzyl, pyridyl, pyrazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, benzopyrrolyl, pyridazine, pyrimidine, pyrazine 、-CH 2 CH 2 CN、-CHCNCH 3 、-CH 2 CH 2 CH 2 CN、-CH 2 CHCNCH 3 、-CHCNCH 2 CH 3 、-CH 2 CH 2 F、-CHFCH 3 、-CH 2 CH 2 CH 2 F、-CH 2 CHFCH 3 、-CHFCH 2 CH 3 、-CH 2 CH 2 Cl、-CHClCH 3 、-CH 2 CH 2 CH 2 Cl、-CH 2 CHClCH 3 、-CHClCH 2 CH 3 、-CH 2 CH 2 Br、-CHBrCH 3 、-CH 2 CH 2 CH 2 Br、CH 2 CHBrCH 3 、-CHBrCH 2 CH 3 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ; ; ; ; ; ; ; ; ; ; X independently represents O or S.
  4. 4. The pyridopyrimidine dione compound containing isoxazole units, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, as claimed in claim 1, wherein the compound is selected from the group consisting of: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。
  5. 5. A process for producing a pyridopyrimidine dione compound containing an isoxazole unit, or a stereoisomer thereof, or a salt thereof or a solvate thereof as claimed in any one of claims 1 to 4, comprising the steps of: (1) ; (2) 。
  6. 6. The method for producing a pyridopyrimidine dione compound having an isoxazole unit, or a stereoisomer thereof, or a salt thereof, or a solvate thereof according to claim 5, wherein the step (2) is: 。
  7. 7. A composition characterized by comprising the pyridopyrimidine diketone compound containing an isoxazole unit or a stereoisomer thereof or a salt thereof or a solvate thereof according to any one of claims 1 to 4, and an agriculturally usable adjuvant or fungicide, insecticide or herbicide, wherein the formulation of the composition is selected from Emulsifiable Concentrates (EC), powders (DP), wettable Powders (WP), granules (GR), aqueous Solutions (AS), suspensions (SC), ultra low volume sprays (ULV), soluble Powders (SP), microcapsules (MC), smoke agents (FU), aqueous Emulsions (EW), water dispersible granules (WG).
  8. 8. Use of a pyridopyrimidine dione compound containing an isoxazole unit, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, as claimed in any one of claims 1 to 4, or a composition as claimed in claim 7, for the manufacture of a medicament for controlling an agricultural pest which is a hemipteran pest, wherein the hemipteran pest is a pisiform, brown planthopper, bemisia tabaci.
  9. 9. A method for controlling agricultural diseases and insect pests is characterized in that the pyridopyrimidine diketone compound containing an isoxazole unit or a stereoisomer thereof, or a salt thereof or a solvate thereof or the composition of claim 7 is allowed to act on harmful pests or living environments thereof, wherein the harmful pests are hemiptera pests, and the hemiptera pests are Pisum sativum aphid, brown planthopper and bemisia tabaci.
  10. 10. A method for protecting plants from agricultural pests, comprising the method step wherein the pest is contacted with a pyridopyrimidine dione compound containing isoxazole units, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, as claimed in any one of claims 1 to 4, or a composition as claimed in claim 7.

Description

Pyridopyrimidine diketone compound containing isoxazole unit and preparation method and application thereof Technical Field The invention relates to the field of chemical industry and pesticides, in particular to a pyridopyrimidine diketone compound containing an isoxazole unit, a preparation method thereof and application thereof in preparing medicines for preventing and controlling pea aphids, brown planthoppers and bemisia tabaci. Background Pea aphids, brown planthoppers and bemisia tabaci are three important pests which are widely harmful and obviously affected in the current agricultural production, and have the characteristics of high explosiveness, high transmissibility and high adaptability in various crop planting systems, so that serious threat is formed to the agricultural production and grain safety. The Pisum sativum aphid is one of the most common and most damaging pests on leguminous crops in China. The breeding capability is extremely strong, the population quantity can be rapidly amplified through parthenogenesis, and the population quantity is geometrically increased under proper conditions, so that the insect population density is rapidly increased in a short time. The pea aphid sucks the juice of the leaf blade, the tender tip and the flower device by the piercing-sucking type mouth device, so that the plant has the symptoms of leaf rolling, deformity, growth stagnation and the like, secretes a large amount of honeydew to cause coal pollution, and seriously influences photosynthesis. In addition, pea aphids are an important medium for various plant viruses, and can transmit diseases such as bean mosaic virus and the like, thereby obviously aggravating yield loss. When the large-area outbreak occurs, the yield of crops can be reduced by 30% -50%, and even the crops are in harvest-free. Brown planthoppers are one of homoptera pests which are most serious in rice production, and have the biological characteristics of strong migratory property, high propagation speed, wide applicable range and the like. Brown planthoppers mainly absorb juice from the base of rice stems, so that plants are desiccated and withered to form typical dead-center withered plants. Large-scale migration and group outbreak are easy to occur under the high-temperature and high-humidity conditions, and large-area lodging and withering of the paddy field are often caused. Brown planthoppers not only cause direct damage, but also can transmit virus diseases such as rice black streaked dwarf and the like, and further enlarge the damage degree. Main rice areas in China are affected by different degrees each year, and 20% -60% of rice yield reduction can be caused in severe outbreak years. Bemisia tabaci is an important worldwide invasive pest, and the host range is extremely wide, so that more than 300 cash crops including vegetables, cotton, fruit trees, flowers and the like can be known to be damaged. The bemisia tabaci has strong fertility, overlapped generation and outstanding stress resistance, and is easy to generate resistance to conventional medicaments. It takes the juice of the leaf back of the host to cause yellowing, wilting and poor growth of the leaf, and induces the coal pollution disease by secreting honeydew, thus reducing the photosynthesis efficiency of crops. Of particular importance, bemisia tabaci is a highly efficient transmission medium for a variety of plant viruses (e.g., tomato yellow leaf curl virus), one of the most threatening pests in the global horticultural and vegetable industries. Outbreaks in facility agriculture and open field vegetables are common, and yield losses can be 30% -70%. The current medicines for preventing and controlling pea aphids, brown planthoppers and bemisia tabaci are mostly conventional chemical pesticides, and the medicines generally have the problems of high environmental protection pressure, quick resistance generation, high risk on non-target organisms and the like. With the increase of forbidden pesticides, development of green, safe, efficient and novel-mechanism-of-action alternative medicaments has become an urgent need for green development of agriculture and ensuring of grain safety. Patent publication number CN113651811a discloses a pyridopyrimidinone compound containing isoxazole, and biological activity test results show that part of the compound has better insecticidal activity on sogatella furcifera. Patent publication No. CN120923496A discloses a pyridopyrimidinone mesoionic derivative containing a dithioacetal unit, a preparation method and application thereof, and biological activity test results show that part of compounds have better insecticidal activity on pea aphids. Patent publication No. CN113292557A discloses a pyridopyrimidinone mesoionic derivative containing indole units, a preparation method and application thereof, and biological activity test results show that part of compounds have better insecticidal activity on pea aphids. The abov