CN-122010934-A - Pyrido [1,2-a ] pyrimidine mesoionic derivative containing amide structure, and preparation method and application thereof

CN122010934ACN 122010934 ACN122010934 ACN 122010934ACN-122010934-A

Abstract

The invention relates to a pyrido [1,2-a ] pyrimidine mesoionic derivative containing an amide structure, a preparation method and application thereof. The compound has the structure shown in the formula (I), has excellent insecticidal activity on the pea tail-trimming aphids, the sogatella furcifera, the plutella xylostella, the spodoptera frugiperda and the like, can be used for preparing medicines for preventing and controlling the pests such as the pea tail-trimming aphids, the sogatella furcifera, the plutella xylostella and the spodoptera frugiperda, and has the advantages of simple structure and preparation process and low production cost. (I)

Inventors

SONG BAOAN
ZHANG LUOMAN
Song Runjiang
HU DEYU
ZHANG JIAN
WANG JIAN
LUO YUQIN

Assignees

贵州大学

Dates

Publication Date: 20260512
Application Date: 20260107

Claims (9)

1. A pyrido [1,2-a ] pyrimidine-based mesogenic derivative containing an amide structure, which is characterized by comprising a compound shown as a general formula (I) or a stereoisomer thereof, or a salt thereof or a solvate thereof, wherein the general formula (I) has the following structural formula: (I) Wherein X represents a nitrogen atom or a carbon atom; R 1 is independently selected from one or more 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; R 2 is independently selected from one or more of hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, mercapto, 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; R 3 is independently selected from one or more of optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl; R 4 is independently selected from one or more of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl; R 5 is independently selected from one or more of hydrogen, deuterium, halogen, nitro, hydroxy, amino, mercapto, cyano, optionally substituted or unsubstituted alkyl.
2. The pyrido [1,2-a ] pyrimidine-based mesoionic derivative having an amide structure according to claim 1, wherein: R 1 is independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted 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, halogen, cyano, nitro, hydroxy, amino, mercapto, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkenyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl; R 3 is independently selected from one or more of substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkynyl, substituted or unsubstituted C 3 -C 6 cycloalkyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl; R 4 is independently selected from one or more of hydrogen, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkynyl, substituted or unsubstituted C 3 -C 6 cycloalkyl, substituted or unsubstituted C 6 -C 15 aryl, substituted or unsubstituted C 5 -C 6 heteroaryl. R 5 is independently selected from one or more of hydrogen, deuterium, halogen, nitro, hydroxy, amino, mercapto, cyano, C1-C6 alkyl; the substitution means substitution with at least one of halogens.
3. The pyrido [1, 2-a ] pyrimidine-based mesoionic derivative having an amide structure according to claim 1, wherein: R 1 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 、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、 ; R 3 is independently selected from methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, propenyl 、-CH 2 F、-CHF 2 、-CH 2 Cl、-CHCl 2 、-CCl 3 、-CH 2 Br、-CHBr 2 、-CBr 3 、-CH 2 CH 2 Cl、-CH 2 CH 2 Br、-CH 2 CH 2 F、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、。
4. The pyrido [1, 2-a ] pyrimidine derivatives containing an amide structure according to claim 1, wherein the specific compounds are selected from the group consisting of: 。
5. the process for producing pyrido [1, 2-a ] pyrimidine derivatives containing an amide structure according to claim 1 to 4, comprising: the compound shown in the general formula II and the compound shown in the general formula III are reacted to prepare the compound shown in the general formula I, and the reaction equation is as follows: 。
6. A composition characterized by comprising the pyrido [1, 2-a ] pyrimidine dielectric ion derivative containing an amide structure AS defined in any one of claims 1-4 and an agriculturally-useful auxiliary agent, wherein the formulation of the composition is selected from Emulsifiable Concentrates (EC), powders (DP), wettable Powders (WP), granules (GR), aqueous Solutions (AS), suspending agents (SC), ultra-low volume sprays (ULV), soluble Powders (SP), microcapsules (MC), smoke agents (FU), aqueous Emulsions (EW) and water dispersible granules (WG).
7. Use of pyrido [1, 2-a ] pyrimidine derivatives containing an amide structure according to any one of claims 1 to 4, or of the composition according to claim 6, for controlling agricultural pests, which are hemiptera and lepidoptera pests, which are aphids, hawk hoppers, plutella xylostella, spodoptera frugiperda.
8. A method for controlling agricultural pests, which is characterized in that the pyrido [1, 2-a ] pyrimidine mesoionic derivative containing an amide structure according to any one of claims 1 to 4 or the composition according to claim 6 is allowed to act on harmful pests or living environments thereof, wherein the agricultural pests are hemiptera and lepidoptera pests, and the agricultural pests are aphids, hawk hoppers, plutella xylostella and spodoptera frugiperda.
9. A method for protecting plants from agricultural pests comprising the method step wherein the pest is contacted with a pyrido [1,2-a ] pyrimidine-based mesogenic derivative containing an amide structure according to any of claims 1 to 4, or a composition according to claim 6.

Description

Pyrido [1,2-a ] pyrimidine mesoionic derivative containing amide structure, and preparation method and application thereof Technical Field The invention relates to the field of chemical industry and pesticides, in particular to a pyrido [1, 2-a ] pyrimidine medium ion derivative containing an amide unit, a preparation method thereof and application of the pyrido [1, 2-a ] pyrimidine medium ion derivative containing the amide unit in medicines for preventing and treating pests such as aphids, sogatella furcifera, plutella xylostella, spodoptera frugiperda and the like. Background Hemiptera and lepidoptera pests are two important agricultural pests, and have the characteristics of multiple types, large influence and frequent outbreaks of disasters, the occurrence range and the severity of the pests often cause great losses to national economy of China, particularly agricultural production, and the yield and the quality of crops are seriously influenced. Therefore, the prevention and control of agricultural diseases and insect pests plays an important role in guaranteeing grain safety, improving crop quality and protecting ecological environment. The rice planthoppers belong to Hemiptera plant hopper (DELPHACIDAE) pests, are migratory plant hopper-onset pests with the largest occurrence area and the heaviest loss in the production of rice in China and the world, and mainly comprise brown planthoppers (NILAPARVATA LUGENS), sogatella furcifera (Sogatella furcifera) and Laodelphax striatellus (Laodelphax striatellus). The pests have high propagation speed and strong destructive power, are also the culprit of carrying viruses, can spread the germs such as southern black streaked dwarf virus, rice sheath blight and the like of rice, cause the growth of the rice to be blocked, even cause the whole rice plant to be withered, lodged and even have no particles to be harvested when serious, and greatly influence the health and the yield of the rice. During the serious outbreak, the occurrence area of the national rice planthoppers reaches 3.3 hundred million mu times, the practical loss of the rice yield caused by the year exceeds 100 ten thousand tons, and the loss can even reach 40-60 percent. Aphids (Aphid) are a collective term for the general class of aphids of the order hemiptera, a total of 10 families 4400 have been found, most of which are aphids, and which are one of the most productive and damaging pests in almost all cultivated crops, and can be directly or indirectly harmful to the crop. The direct pest mainly comprises that if aphid sucks leaf blade and tender ear juice to cause leaf curl, withering and the like, which seriously affect plant growth, the indirect pest mainly comprises that aphid can be used as a virus transmission medium to transmit plant virus to induce plant virus diseases to cause yield reduction, and huge loss is brought to agricultural production each year, and the serious pest is as high as 40-50%. Lepidoptera (Lepidoptera) pests include agricultural pests such as spodoptera frugiperda, plutella xylostella, and the like. The plutella xylostella (Plutella xylostella) is one of the most destructive pests to cruciferous crops in the world, belongs to the plutella xylostella (Plutellidae), has the characteristics of short occurrence period, high fertility, quick generation replacement, long growing season and the like, is particularly serious to cruciferous vegetables, can reach 70-90%, and can cause great economic loss and seriously threaten the grain safety, and the yield loss of serious victimized field vegetables can reach more than 80-90%. Spodoptera frugiperda (Spodoptera frugiperda), belonging to the genus Spodoptera of the family Spodoptera of the order lepidopteridae (nocuitae), native to tropical and subtropical areas of america, is a multi-feeding pest whose host plants are more than 350 species, has high propagation and transmission potential, and particularly prefers gramineous plants such as corn, sorghum, sugarcane, and the like. It is counted that in the serious generation area of spodoptera frugiperda, the corn pest plant rate can reach more than 90%. Due to the strong migration ability of spodoptera frugiperda adults, the trails of spodoptera frugiperda adults are found in multiple provinces after the spodoptera frugiperda adults rapidly spread worldwide and invade Yunnan of China from month 1 in 2019. In a short time after the invasion of China, the area of the crops subjected to disaster reaches millions of hectares. The spodoptera frugiperda is listed as the first of a class of crop pest and disease damage directory by agricultural rural areas in 9 months 2020, and is clearly required to be controlled and strengthened by a first file in the center in the successive 3 years 2020-2022. The reasonable use of pesticides is an important means for guaranteeing agricultural production, but most of the current pesticides for controlling agricultural pests such as hemiptera an