1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative

A technology of -2-N- and hexahydrotriazine, which is applied in the field of 1, can solve the problems of complex production process, low output and high cost, and achieve the effect of simple production process, high output and low cost

Inactive Publication Date: 2010-07-21
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But until now, neonicotinoid insecticides still have few varieties; and the production process is complicated, the output is low, and the cost is high; they cannot replace a large number of existing insecticides and pesticides that have been used for a long time in the current agricultural production in the world

Method used

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  • 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative
  • 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative
  • 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of 1-(2-furylmethyleneamino)-5-(2-chloro-5-pyridylmethyl)-1,3,5-hexahydrotriazine-2-N-nitroimine (Ia):

[0059] (1) Put 5.0 g of nitroguanidine and 70 mL of water into a 250 mL three-necked bottle. The mixture was heated to 55°C under magnetic stirring, and 3.5 g of 85% hydrazine hydrate was added dropwise from the dropping funnel. Keep the temperature at 55-60°C and continue the reaction for 20min, to an orange-yellow clear liquid, rapidly cool with an ice-water bath, adjust the pH value to 5-6, continue to cool to 0°C, hold for 1h, and filter under reduced pressure to obtain a solid. Washed with a small amount of ice water to obtain 2.5 g of pale yellow powder (1-nitro-3-aminoguanidine) with a yield of 44%.

[0060] (2) 2.0 g of 1-nitro-3-aminoguanidine, 80 mL of anhydrous ethanol and 0.2 mL of glacial acetic acid were put into a 250 mL three-necked flask. The mixture was heated to 65° C. under magnetic stirring, and a mixed solution of 1.94 g of 2-furanca...

Embodiment 2

[0067] Preparation of 1-(2-furylmethyleneamino)-5-(2-tetrahydrofuranmethyl)-1,3,5-hexahydrotriazine-2-N-nitroimine Ib:

[0068] (1) Preparation of 1-nitro-3-aminoguanidine in the same manner as in step (1) of Ia.

[0069] (2) Preparation of 1-nitro-3-(2-furamethylene) aminoguanidine in the same manner as in step (2) of Ia.

[0070] (3) 2.0 g of 1-nitro-3-(2-furamethylene) aminoguanidine and 20 mL of acetonitrile were put into a 100 mL three-necked flask, and heated to 60° C. under magnetic stirring. A mixed solution of 1.03 g of 2-aminomethyltetrahydrofuran and 1.97 g of 37% aqueous formaldehyde solution was slowly added dropwise from the funnel. After the dropwise addition was completed, the temperature was maintained for 1 h. Column chromatography (petroleum ether:ethyl acetate=2:1) ​​to obtain 1-(2-furamethyleneamino)-5-(2-tetrahydrofuranmethyl)-1,3,5-hexahydrotriazine-2 -N-Nitroimine 2.35. Yield 72%, melting point: 142°C-143°C.

[0071] Elemental analysis: Measured va...

Embodiment 3

[0076] Preparation of 1-(2-furylmethyleneamino)-5-(2-furylmethyl)-1,3,5-hexahydrotriazine-2-N-nitroimine Ic:

[0077] (1) Preparation of 1-nitro-3-aminoguanidine in the same manner as in step (1) of Ia.

[0078] (2) Preparation of 1-nitro-3-(2-furamethylene) aminoguanidine in the same manner as in step (2) of Ia.

[0079] (3) 2.0 g of 1-nitro-3-(2-furamethylene) aminoguanidine and 20 mL of acetonitrile were put into a 100 mL three-necked flask, and heated to 60° C. under magnetic stirring. A mixed solution of 0.99 g of 2-aminomethylfuran and 1.97 g of a 37% aqueous formaldehyde solution was slowly added dropwise from the funnel. After the dropwise addition was completed, the temperature was maintained for 1 h. Column chromatography (petroleum ether:ethyl acetate=2:1) ​​to obtain 1-(2-furamethyleneamino)-5-(2-furanmethyl)-1,3,5-hexahydrotriazine-2 -N-nitroimine 2.23 g. Yield 69%, melting point: 114°C-117°C.

[0080] Elemental analysis: Measured value: C% 49.06 H% 4.41 N% 2...

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Abstract

The invention discloses a 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative belonging to an anabasine pesticide analogue. The 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative is represented by a general formula shown as the specification. A preparation method of the 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivative comprises the following steps of: reacting hydrazine hydrate with nitroguanidine to prepare 1-nitro-3-aminoguanidine; reacting with aromatic aldehyde or aromatic ketone by heating for 6 hours to obtain 1-nitro-3-aromatic methylene aminoguanidine; and reacting with a mixing solution of heterocyclic methylamine and a formaldehyde water solution at 60 DEG C for 1 hour to obtain a 1-(aromatic methylene amino)-5-(heterocyclic methyl)-hexahydrotriazine-2-N- nitroimine derivative. The invention has favorable insecticidal activity and can be used as an effective active constituent of insecticide to prepare various pesticide excipients, such as emulsion, aqueous suspension, emulsion in water and the like. The invention has the advantages of good insecticidal effect, low toxicity to human and livestock, safe use, simple production process, high yield and low cost.

Description

technical field [0001] The invention belongs to neonicotinoid pesticide analogs, specifically 1,5-disubstituted hexahydrotriazine-2-N-nitroimine derivatives. Background technique [0002] Insecticides and pesticides used in agricultural production are important agricultural production materials to kill pests that harm the growth of crops and ensure increased crop yields. Chemical pesticides have played an important role in the development of agricultural production because of their good insecticidal effect and fast insecticidal speed. The long-term use of chemical pesticides has also brought some negative effects; for example, the residues of pesticides in plants, agricultural products, food, and soil exceed the specified indicators, causing harm to people's bodies and to crops. growth affects. In order to reduce soil environmental pollution, promote crop growth, ensure people's food safety, and protect human health, agronomists, chemists and pesticide experts from all ove...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D405/06C07D401/06A01N43/64A01P7/04
Inventor 薛思佳刘丽
Owner SHANGHAI NORMAL UNIVERSITY
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