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CN-121974909-A - Pyrido [1,2-a ] pyrimidinone compound containing 1,3, 4-oxadiazole thioether unit, and preparation method and application thereof

CN121974909ACN 121974909 ACN121974909 ACN 121974909ACN-121974909-A

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a preparation method and application of a pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit, wherein the compound is shown as a general formula I, R 1 independently represents alkyl, aryl, heterocyclic group and the like, and R 2 independently represents hydrogen, alkyl, halogen and the like. R 3 independently represents methyl, ethyl, aryl, heterocyclic group and the like, and the compound has good control effect on plant hoppers, aphids and the like.

Inventors

  • ZHANG JIAN
  • Mu Shimei
  • WU ZENGXUE
  • SONG BAOAN
  • HU DEYU
  • ZHANG TINGTING
  • Peng Yanqun

Assignees

  • 贵州大学

Dates

Publication Date
20260505
Application Date
20260121

Claims (10)

  1. 1. A pyrido [1,2-a ] pyrimidinone compound containing a 1,3, 4-oxadiazole thioether unit 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 of hydrogen, 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; R 2 is independently selected from hydrogen, alkyl, halogen, and the like; R 3 is independently selected from one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl.
  2. 2. The pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit or a stereoisomer thereof, or a salt thereof or a solvate thereof according to claim 1, wherein: R 1 is independently selected from one or more of hydrogen, 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, alkyl, halogen; r 3 is independently selected from one or more of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkenyl, cyano, C 1 -C 6 haloalkyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl; 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 pyrido [1,2a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit or a stereoisomer thereof, or a salt thereof or a solvate thereof according to claim 1, wherein: R 1 is independently selected from hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridinyl, pyrazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, benzopyrrolyl, pyridazine, pyrimidine, pyrazine 、-CN、-CH 2 CN、-CH 2 CH 2 CN、-CCNCH 3 、-CCNCH 2 CH 3 、-CH 2 F、-CH 2 CH 2 F、-CHFCH 3 、-CH 2 Cl、-CH 2 CH 2 Cl、-CHClCH 3 、-CH 2 Br、-CH 2 CH 2 Br、-CHBrCH 3 、 、 、 、、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ; R 2 is independently selected from hydrogen, methyl, halogen; R 3 is independently selected from hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, methoxy, vinyl, phenyl, benzyl, pyridinyl 、-CH 2 F、-CH 2 CH 2 F、-CHFCH 3 、-CH 2 Cl、-CH 2 CH 2 Cl、-CHClCH 3 、-CH 2 Br、-CH 2 CH 2 Br、-CHBrCH 3 .
  4. 4. The pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit according to claim 1, wherein the pyrido [1,2-a ] pyrimidinone compound is selected from the group consisting of: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。
  5. 5. The process for producing a pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit or a stereoisomer thereof, or a salt thereof or a solvate thereof according to any one of claims 1 to 4, comprising the steps of: (1) ; (2) ; (3) ; (4) 。
  6. 6. The method for producing pyrido [1,2-a ] pyrimidinone compounds containing 1,3, 4-oxadiazole thioether unit or stereoisomers thereof, or salts thereof or solvates thereof according to claim 5, wherein said step (2) is: Wherein X is Br or I.
  7. 7. A composition characterized by comprising the pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether 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 acceptable adjuvant or fungicide, insecticide or herbicide, wherein the formulation of the composition is selected from the group consisting of 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 (FU), emulsions in water (EW), water dispersible granules (WG).
  8. 8. The use of a pyrido [1,2-a ] pyrimidinone compound containing a 1,3, 4-oxadiazole thioether unit or a stereoisomer thereof, or a salt thereof or a solvate thereof according to any one of claims 1 to 4, or the composition according to claim 7, for the preparation of a medicament for controlling agricultural pests, which are hemiptera pests, which are plant hoppers and aphids.
  9. 9. A method for controlling agricultural insect pests, which is characterized in that the pyrido [1,2-a ] pyrimidinone compound containing a 1,3, 4-oxadiazole thioether unit or a stereoisomer thereof, a salt thereof or a solvate thereof or the composition of claim 7 according to any one of claims 1 to 4 is allowed to act on harmful substances or living environments thereof, wherein the harmful substances are hemiptera pests, and the hemiptera pests are plant hoppers and aphids.
  10. 10. A method for protecting plants from agricultural pests, comprising the method step wherein the pest is contacted with a pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit as defined in any one of claims 1 to 4, or a stereoisomer thereof, or a salt thereof or a solvate thereof, or a composition as defined in claim 7.

Description

Pyrido [1,2-a ] pyrimidinone compound containing 1,3, 4-oxadiazole thioether unit, and preparation method and application thereof Technical Field The invention relates to the fields of chemical industry and pesticides, in particular to a pyrido [1,2-a ] pyrimidinone compound containing a1, 3, 4-oxadiazole thioether unit, a preparation method thereof and application thereof in medicines for preventing and controlling plant hoppers and aphids. Background Pea aphids (school name: acyrthosiphon pisum), belonging to the genus Sinonosma of the order Aphis of the order Hemiptera, are important agricultural pests widely distributed in the temperate region of the world, and are rampant especially in leguminous crop planting areas. The body is tiny, the length of the adult body is about 2-4 mm, the body color is mostly light green or yellow green, the back has clear black stripes, the antenna is slender, and the abdomen end has a pair of abdominal tubes, which is a typical characteristic of aphid insects. The wing-free parthenogenetic aphid is round in shape, and the wing-free parthenogenetic aphid has transparent veins and can diffuse to a new host plant through migration. The host range of pea aphids is mainly leguminous plants, and the core hosts comprise peas, broad beans, alfalfa, clover and the like, wherein peas are the most preferred host crops. The insect is originally produced in Europe and then is spread to various places of the world along with agricultural product trade, and is widely distributed in the main production areas of peas such as northeast China, north China, northwest China and the like at present, the warm and moist climatic conditions are most suitable for growth and reproduction of the peas, and the peas aphid has the characteristic of typical parthenogenesis and ampholytic reproduction alternation, can finish 10-20 generations in one year, and has extremely strong reproduction capability. The damage of pea aphids to agricultural production is mainly characterized in that firstly, juice of host plants is directly punctured and sucked, so that pea leaves curl and yellow, plant growth is weakened, the pod bearing rate is reduced, seeds are shrunken, the plants die when serious, the yield is generally reduced by 10% -30%, the yield of serious land parcels is reduced by more than 50%, and secondly, a plurality of plant virus diseases such as pea mosaic virus, broad bean wilting virus and the like are indirectly transmitted, and the damage caused by the virus diseases is more serious than the direct damage of aphids, so that the yield loss is further aggravated. In addition, the honeydew secreted by the pea aphids can induce coal pollution to influence photosynthesis of host plants, meanwhile, the honeydew can attract ants to eat, and the ants can protect the aphids from being invaded by natural enemies, so that an 'ant and aphid symbiotic' relationship is formed, and the harm of the aphids is further promoted. As typical phytophagous insects, pea aphids are also important members in the ecological system, and population quantity changes of the pea aphids influence survival of natural enemies such as ladybirds, green laces and aphidius gifuensis, and have a certain influence on ecological balance of farmlands. At present, the drug resistance of the drug for preventing and controlling pea aphids evolves rapidly, and the drug has higher safety risk to non-target organisms, so that the research and development of the green, safe, efficient, low-risk and novel-acting-mechanism alternative drug has become an urgent task for supporting the green development of agriculture and guaranteeing the grain safety. The mesoionic pesticide is superior to the traditional neonicotinoid pesticide in molecular structure innovation and drug resistance management potential as a novel pesticide, and is currently becoming the key research content in the fields of pesticide chemistry and insect toxicology. 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 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 aphids. Patent publication No. CN112851665A discloses a novel mesoionic compound which has excellent control effects on pests in agriculture, particularly on plutella xylostella, armyworm, alfalfa aphid and the like. Patent publication No. CN118126030A discloses a pyrazoline-1, 3, 4-oxadiazole thioacetamide compound with a novel structure, a preparation method thereof and application thereof as an agricultural pesticide, and a biological activity test shows that part of the compound has bet