CN-122010935-A - Pyrido [1, 2-a ] pyrimidine mesoionic derivative containing sulfoxide structure, and preparation and application thereof

CN122010935ACN 122010935 ACN122010935 ACN 122010935ACN-122010935-A

Abstract

The invention relates to a pyrido [1,2-a ] pyrimidine mesoionic derivative containing a sulfoxide structure, a preparation method and application thereof. The compound has the following formula (I), has excellent insecticidal activity on frankliniella occidentalis, sogatella furcifera, aphid, spodoptera frugiperda, plutella xylostella, chilo suppressalis, prodenia litura, armyworm and the like, and can be used as a medicament or medicament for preventing and treating insect pests such as frankliniella occidentalis, sogatella furcifera, aphid, spodoptera frugiperda, plutella xylostella, chilo suppressalis, spodoptera litura, armyworm and the like. The structure and the preparation process are simple, and the production cost is low. (I)

Inventors

SONG BAOAN
ZHANG LUOMAN
Song Runjiang
HU DEYU
ZHANG JIAN
WANG ZHIJIA
WANG JIAN

Assignees

贵州大学

Dates

Publication Date: 20260512
Application Date: 20260107

Claims (10)

1. A pyrido [1,2-a ] pyrimidine-based mesogenic derivative containing a sulfoxide 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 the method comprises the steps of 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.
2. The pyrido [1,2-a ] pyrimidine-based mesoionic derivative having a sulfoxide 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; the substitution refers to substitution by at least one or more of alkynyl, cyano, halogen, alkyl, haloalkyl.
3. The pyrido [1,2-a ] pyrimidine-based mesoionic derivative having a sulfoxide 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-based mesogenic derivative containing a sulfoxide structure according to claim 1, characterized in that it is selected from the following specific compounds:
5. The process for preparing a pyrido [1, 2-a ] pyrimidine-based mesoionic derivative having a sulfoxide structure according to claims 1 to 4, comprising: 1) ; 2) 。
6. The method for producing a pyrido [1, 2-a ] pyrimidine-based mesoionic derivative having a sulfoxide structure according to claim 5, comprising: 。
7. A composition is characterized by comprising the pyrido [1, 2-a ] pyrimidine dielectric ion derivative containing a sulfoxide structure according to 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).
8. The pyrido [1, 2-a ] pyrimidine mesoionic derivative containing a sulfoxide structure according to any one of claims 1 to 4, or the use of the composition according to claim 7 in the preparation of a medicament for controlling agricultural diseases and insect pests, wherein the agricultural diseases and insect pests are frankliniella occidentalis, sogatella furcifera, aphid, spodoptera frugiperda, plutella xylostella, chilo suppressalis, prodenia litura and armyworm.
9. A method for preventing and controlling agricultural diseases and insect pests is characterized in that the pyrido [1, 2-a ] pyrimidine mesoionic derivative containing a sulfoxide structure or a composition according to any one of claims 1-4 acts on harmful pests or living environments thereof, wherein the agricultural diseases and insect pests are frankliniella occidentalis, white-back planthoppers, aphids, spodoptera frugiperda, plutella xylostella, chilo suppressalis, prodenia litura and armyworms.
10. 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 a sulfoxide structure according to any of claims 1 to 4, or a composition according to claim 7.

Description

Pyrido [1, 2-a ] pyrimidine mesoionic derivative containing sulfoxide structure, and preparation 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 a sulfoxide unit, a preparation method thereof and application of the pyrido [1, 2-a ] pyrimidine medium ion derivative containing the sulfoxide unit in medicines for preventing and treating pests such as frankliniella occidentalis, rice planthoppers, aphids, spodoptera frugiperda, plutella xylostella, chilo suppressalis, corn borers, armyworms and the like. Background The crop insect pest is one of main agricultural disasters in China, has the characteristics of multiple types, large influence and frequent outbreak of disasters, and has the occurrence range and severity which cause great loss to agricultural production in China. Among them, hemiptera pests, thysanoptera pests, and lepidoptera pests are several important classes of agricultural pests. The rice planthoppers are main migratory pests of rice, belong to the Hemiptera (Hemiptera) planthopper family (DELPHACIDAE) pests and mainly comprise three types of brown planthoppers (NILAPARVATA LUGENS), sogatella furcifera (Sogatella furcifera) and Laodelphax striatellus (Laodelphax striatellus). They pose serious threat to rice production by sucking rice juice, spawning and spreading rice virus diseases, and the like, and the burst nature thereof also brings great difficulty to control. The rice planthoppers have the characteristics of high propagation speed, large population quantity, strong migratory capacity and the like, and once the rice planthoppers occur, the rice is extremely easy to cause destructive damage, so that the yield of the rice is reduced and even the rice is dead. Thysanoptera (Thysanoptera) pests are commonly known as thrips, and are a class of agricultural pests with small size and huge harm, wherein frankliniella occidentalis (FRANKLINIELLA OCCIDENTALIS (Pergande)) is taken as the most damaging representative class. The original North America pests have spread to over 70 countries and regions worldwide, and the host range is remarkable, and more than 500 vegetables, flowers and economic crops including peppers, cucumbers, eggplants, roses, chrysanthemums and the like can be endangered. Besides the fact that frankliniella occidentalis directly eats tissue juice, the frankliniella occidentalis causes 30-50% of crop yield loss, and even causes sterilization in severe cases, the frankliniella occidentalis can also transmit various viruses, and the frankliniella occidentalis can cause indirect harm to plants. The virus is a high-efficiency transmission medium of high-harm plant viruses such as tomato spotted wilt virus, and the virus diseases caused by the virus can spread rapidly among crops, and can cause destructive loss of more than 80% on the yield and commodity value of crops such as tomatoes, peppers and the like. In addition, frankliniella occidentalis is extremely strong in fertility, can generate more than 15 generations each year, has obvious drug resistance to various common pesticides, and greatly increases the control difficulty and cost, so that the frankliniella occidentalis is recognized as one of the first threats of global agriculture, especially in agricultural production, which must be strictly controlled. Lepidoptera (Lepidoptera) pests include agricultural pests such as spodoptera frugiperda, plutella xylostella, and chilo suppressalis. Wherein spodoptera frugiperda (Spodoptera frugiperda) and chilo suppressalis (Chilo suppressalis) as representative pests of lepidoptera cause serious harm in the growth period of various grain crops such as rice, corn and the like. Spodoptera frugiperda belongs to Spodoptera frugiperda (Spodoptera) of the genus Spodoptera of the family lepidopteridae, is originally produced in tropical and subtropical areas of america, has wide distribution of insects and various hosts, has the characteristics of strong migratory capacity, high propagation speed, edibility, and the like, damages various crops such as corn, rice, wheat and the like, and causes serious threat to global agriculture. Plutella xylostella (Plutella xylostella), belonging to the family Plutella xylostellaceae (Plutellidae), also known as "trichomonad", is a cruciferous pest that is a worldwide outbreak hazard. The plant growth regulator has the advantages of short occurrence period, strong adaptability and fertility, wide hosts, easy generation of drug resistance and high mobility, the strong mobility aggravates the harm degree, the hazard range is enlarged, almost all provinces and cities in China have occurrence, and the control is difficult. At present, chemical agent control is still the most direct and effective means for controlling the pests, but the problem of drug resistance of the insecticide caused by long-term, large-area and