Nitrogen-containing heterocyclic compound with pesticidal activity, preparation and application thereof
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A compound and six-membered heterocycle technology, applied in the field of new insecticides, can solve problems such as narrow insecticidal spectrum and limited drug selectivity
Inactive Publication Date: 2010-07-07
EAST CHINA UNIV OF SCI & TECH
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[0003] However, due to the serious resistance problem caused by the excessive and frequent use of imidacloprid and the cross-resistance between neonicotinoid insecticides due to structural similarity, the application of this type of compound is limited to a certain extent, and it has become a constraint on this field. Neonicotinoid insecticides are mainly effective against Homoptera and Coleoptera pests, and their relatively narrow insecticidal spectrum also limits the selectivity of insecticides in pest control
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[0081] The preparation method of the compound of the present invention
[0082] The synthetic method of general formula (A) compound is as follows:
[0083]
Embodiment 1-22
[0086] Example 1-22: Preparation of 1,4-dihydropyridine nitromethylene compounds
[0087]
[0088] Dissolve aromatic aldehyde (4.5mmol, 150mol%) in absolute ethanol (30mL) solution at room temperature, then add malononitrile (4.5mmol, 150mol%) to continue stirring, drop piperidine (10mol%) and stir After 2-4 hours, nitromethylene compound (3mmol, 150mol%) was added and the mixture was heated and refluxed for 3-24 hours. After cooling, it was filtered and washed 3 times with dichloromethane to obtain a solid compound.
[0089]
Embodiment 1
[0091] Example 1: A yellow solid was obtained after filtration with a yield of 82% and a melting point of 223.2-223.7°C. 1 H NMR (400MHz, DMSO-d 6 )δ3.93-4.01(m, 3H), 4.08-4.17(m, 1H), 4.72(s, 1H), 4.74(s, 2H), 6.54(s, 2H, NH 2 ), 6.98(dd, J=1.4, 7.8Hz, 1H), 7.15-7.23(m, 3H), 7.28(d, J=8.0Hz, 1H), 7.64(dd, J=2.6, 8.2Hz, 1H) , 8.28 (d, J=2.0Hz, 1H). 13 C NMR (100MHz, DMSO-d 6 )δ 41.52, 43.90, 51.05, 51.46, 60.12, 106.17, 121.21, 124.39, 126.69, 126.96, 128.73, 131.40, 139.48, 144.78, 149.51, 149.61, 149.90, 152.90. MS (ESI) m / z 409 (M+H). C 20 h 17 ClN 6 o 2 Calculated: C, 58.75; H, 4.19; N, 20.56. Found: C, 58.77; H, 3.89; N, 20.40.
[0092]
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Abstract
The invention relates to a compound with a general formula (A) or an optical isomer, cis-trans isomer or pesticide science-acceptable salt of the compound and a preparation method thereof. The invention also relates to an agricultural composition containing the compound or the optical isomer, cis-trans isomer or pesticide science-acceptable salt of the compound and the application of the agricultural composition. The compound and derivatives thereof have high pesticidal activity on homoptera, lepidoptera and other agricultural and forest pests, such as aphids, plant hoppers, whiteflies, leafhoppers, thrips, cotton bollworms, cabbage caterpillars, diamond back moths, prodenia lituras and armyworms.
Description
technical field [0001] The invention relates to a novel neonicotinoid-like insecticide, its preparation method and application. technical background [0002] In the mid-1980s, Bayer developed the first neonicotinoid insecticide, imidacloprid, and became one of the most successful new insecticides. High activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties, appropriate field stability and environmental friendliness have become an important hotspot for the creation of new pesticides. Later, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran were developed successively (European patents 247477, 296453, 685477, 235725, 235725 , 315826, 192060, 244777, 0386565, 580553, and 1031566, Japanese patents 62292765, 8259568, 8291171, and 7242633). [0003] However, due to the serious resistance problem caused by the excessive and frequent use of imidacloprid...
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