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Aryl amidine structure-containing compound, preparation method and application thereof

A technology for aryl amidines and compounds is applied in the field of compounds containing aryl amidine structures, and can solve the problems of not showing advantages and the like

Pending Publication Date: 2021-05-11
ZHEJIANG RES INST OF CHEM IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The compounds containing (heterocyclic) substituted arylamidine structures shown in the above R-1 and R-2 have certain fungicidal activity, but do not show obvious advantages

Method used

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  • Aryl amidine structure-containing compound, preparation method and application thereof
  • Aryl amidine structure-containing compound, preparation method and application thereof
  • Aryl amidine structure-containing compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Embodiment 1: compound 2 is synthesized

[0103] synthetic route:

[0104]

[0105] Synthetic steps:

[0106] (1) Preparation of intermediate A3:

[0107] Add 13.7g (0.1mol) m-chlorobenzonitrile A1 and 12.2g (0.1mol) 2,5-dimethylphenol A2 to 250mL dry DMF, add 39g (0.12mol) cesium carbonate and 0.75g (0.005mol) ) sodium iodide, dry protection, warming up to reflux, TLC tracking to the end of the reaction. After the reaction was completed, it was cooled, and the reaction liquid was poured into ice water, extracted with ethyl acetate, washed with water, dried, and concentrated to obtain 20.5 g (0.092 mol) of light black liquid intermediate A3 with a yield of 92.1%.

[0108] After testing, the prepared compound is A3, and its performance data are as follows:

[0109] 1 H NMR (600MHz, CDCl 3 )δ:2.13(s,3H,CH3),2.31(s,3H,CH3),6.76(s,1H,Ar-H),6.96-6.97(d,1H,Ar-H),7.07(m,1H ,Ar-H),7.12-7.14(dd,1H,Ar-H),7.15-7.17(d,1H,Ar-H),7.29-7.31(d,1H,Ar-H),7.37-7.39(t ,1H,Ar-H); ...

Embodiment 2

[0130] Embodiment 2: Compound 8 is synthesized

[0131] Compound 8 was prepared by the same method as in Example 1. The performance data of the obtained compound 8 are as follows:

[0132] 1 H NMR (600MHz, CDCl 3 )δ:2.11(s,3H,CH3),2.22(s,3H,CH3),3.03(s,6H,(CH3)2),6.65(s,1H,Ar-H),6.79(s,1H, Ar-H),7.04-7.06(dd,1H,Ar-H),7.38-7.41(t,1H,Ar-H),7.45(s,1H,CH),7.57-7.58(m,1H,Ar- H),7.72-7.73(d,1H,Ar-H); ESI-MS m / z:405[M+H] + .

Embodiment 3

[0133] Embodiment 3: the synthesis of compound 10

[0134] Compound 10 was prepared by the same method as in Example 1. The performance data of the obtained compound 10 are as follows:

[0135] 1 H NMR (600MHz, CDCl 3 )δ:0.93-0.95(t,3H,J=7.2Hz,CH3),1.65(m,2H,CH2),2.11(s,3H,CH3),2.20(s,3H,CH3),3.01(s, 3H, CH3), 3.23(m, 2H, CH2), 6.65(s, 1H, Ar-H), 6.79(s, 1H, Ar-H), 7.04-7.06(d, 1H, J=8.3Hz, Ar -H), 7.38-7.41(t, 1H, J=8.1Hz, Ar-H), 7.45(s, 1H, CH), 7.56-7.58(m, 1H, Ar-H), 7.72-7.73(d, 1H, J=7.7Hz, Ar-H); ESI-MS m / z: 405[M+H] + ..

[0136] (2) preparation preparation

[0137] The following examples are prepared according to the mass ratio.

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PUM

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Abstract

The invention discloses an aryl amidine structure-containing compound with the following general formula F-1, wherein the definition of each substituent group is shown as the specification. The aryl amidine structure-containing compound provided by the invention is suitable for preventing and treating fungal diseases.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, in particular to a class of compounds containing aryl amidine structures. Background technique [0002] The long-term use of existing fungicide varieties has led to disease resistance to existing fungicide varieties, so it is required to continuously discover new fungicide varieties with different mechanisms of action. The excessive use of existing fungicides has brought greater pressure to the environment, so it is required to develop new varieties of fungicides with higher efficiency. [0003] PCT专利申请WO0046184、WO2007031508、WO2008110313、WO2008110314、WO2008110278、WO2008110279、WO2008110280、WO2008110281、WO2007061966、WO2008128639、WO2009083105、WO2009156098、WO2009088103、WO2012025450和WO2012090969公开了脒类化合物在防治作物病害上有一定效果。 [0004] For example: WO2008110313 discloses a compound with an amidine structure as shown in R-1, which has a control effect of more than 70% on barley powdery mildew at a concent...

Claims

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Application Information

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IPC IPC(8): C07D271/06A01N43/82A01P3/00
CPCC07D271/06A01N43/82
Inventor 钟良坤许天明王晓阳胡伟群黄红英魏优昌
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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