N-substituted dioxazine compound as well as preparation method and application thereof

A technology for oxadiazines and compounds, which is applied in the field of N-substituted oxadiazines and can solve the problems of long residual time and the like

Inactive Publication Date: 2012-03-28
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Through research, it is found that compound 14 has a good control effect on lepidopteran pests at a certain dosage, but the residual time is too long

Method used

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  • N-substituted dioxazine compound as well as preparation method and application thereof
  • N-substituted dioxazine compound as well as preparation method and application thereof
  • N-substituted dioxazine compound as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0100] The preparation method of the compound of general structural formula (I) of the present invention comprises following two reactions and carries out, and reaction formula is as follows:

[0101]

Embodiment 1

[0103] (S)-7-Chloro-3,5-dihydro-2-[[methoxycarbonyl(pyridine)amino]formyl]indeno[1,2-e][1,3,4-]oxadi Preparation of Ozine-4a(3H)-Carboxylic Acid Methyl Ester (SIOC-Y-001)

[0104] Add methyl acetate (20ml), 10% Pd / C (50mg) and 2-(benzyl)-7-chloroindeno[1,2-e][1,3,4]oxadioxane in a 50ml reaction flask Oxyzine-2,4a(3H,5H)-dicarboxylic acid 4a-methyl ester (A) (200mg, 0.5mmol), react under hydrogen protection for 30 minutes; add (chlorocarbonyl)(2-pyridine)carbamate methyl ester (130mg, 0.6mmol) in methyl acetate solution (10ml), add N,N-diisopropylethylamine (200mg, 1.5mmol) and remove the hydrogen protection at the same time, replace the nitrogen protection, react for 12-18 hours; remove Protected under nitrogen, washed with water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, concentrated, and separated by silica gel column chromatography to obtain 161.1 mg of a light yellow solid with a yield of 69.5% and a melting point of 150-152°C.

[0105] Simi...

Embodiment 2

[0106] Example 2. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (naphthalene)amino]formyl]indeno[1,2-e][1,3,4 -] Preparation of oxadiazine-4a(3H)-methyl carboxylate (SIOC-Y-002).

[0107]

[0108] Melting point: 81-83°C.

[0109] 1 H NMR (300MHz, CDCl 3 )δ: 8.14(d, J=7.5Hz, 1H), 7.96-7.83(m, 2H), 7.66-7.44(m, 4H), 7.36-7.25(m, 3H), 5.70(d, J=9.0Hz , 1H), 5.26(d, J=9.6Hz, 1H), 3.76-3.64(m, 6H), 3.48(d, J=16.5Hz, 1H), 3.27(d, J=16.8Hz, 1H).

[0110] 3. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl[2-(4-methylpyridine)]amino]formyl]indeno[1,2-e] [1,3,4-]oxadiazine-4a(3H)-methyl carboxylate (SIOC-Y-003)

[0111]

[0112] Melting point: 169-171°C.

[0113] 1 H NMR (300MHz, CDCl 3 )δ: 8.17(d, J=4.8Hz, 1H), 7.43(s, 1H), 7.38(d, J=8.7Hz, 1H), 7.30-7.22(m, 2H), 6.89(d, J=5.1 Hz, 1H), 5.82(d, J=9.9Hz, 1H), 5.24(d, J=9.6Hz, 1H), 3.74(s, 3H), 3.70(s, 3H), 3.45(d, J=16.5 Hz, 1H), 3.22 (d, J = 16.2 Hz, 1H), 2.36 (s, 3H).

[0114] 4. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbony...

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Abstract

The invention relates to an N-substituted dioxazine compound as well as a preparation method and application thereof. The N-substituted dioxazine compound has the following chemical structure general formula (I), wherein Ar in the chemical structure general formula (I) is a benzene ring, a naphthalene ring, and a pyridine or pyrimidine ring system. The compound is prepared with the following two steps: (1) taking 2-(benzyl)-7-benzindene[1,2-e][1,3-4] dioxazine-2,4a(3H,5H)-dicarboxylic acid-4a-methoxycarbonyl group and hydrogen as raw materials, taking Pd/C in solvent a as catalyst a, and carrying out hydrogenation, thus obtaining an intermediate B after reaction is finished; (2) taking (carbonylchloride) (aryl) methyl carhamate as the intermediate C, and carrying out (carbonylchloride) (aryl) methyl carhamate with the intermediate B obtained in the step (1) in the presence of a catalyst b in the solvent b; and obtaining the product N-substituted dioxazine compound. Compared with the prior art, the insecticidalactivity on the armyworm by the N-substituted dioxazine compound is 80-100%.

Description

technical field [0001] The invention relates to an insecticide, in particular to an N-substituted oxadiazine compound with insecticidal activity, its preparation method and application. Background technique [0002] The oxadiazine (oxadiazine) insecticide indoxacarb (indoxacarb) is a sodium channel inhibitory broad-spectrum insecticide (W09211249) developed by Dupont (Dupont) in the United States in 1992. It is based on a new mechanism of insecticidal action, namely Blocking the sodium ion channels of nerve cells reduces the possibility of cross-resistance to commonly used insecticides (such as pyrethrins, organophosphates, and carbamate insecticides). Indoxacarb itself is a precursor insecticide, which removes the methoxycarbonyl group (-COOCH) on the amide nitrogen atom through metabolism in insects. 3 ) into active compounds, which have high insecticidal activity in a broad-spectrum range and incorporate the advantages of good environmental compatibility, low toxicity to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D273/04A01N47/38A01P7/04A01P7/02
Inventor 徐德锋吕龙李绍顺唐庆红付群梅
Owner SHANGHAI JIAO TONG UNIV
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