Methoxyimino phenylacetate compounds containing nitrohydrazinecarboximidamide structures as well as preparation method and application of methoxyimino phenylacetate compounds

A compound, phenethyl technology, applied in the field of methoxyiminophenylacetate compounds and their preparation, can solve the problems of increased drug residues, cumbersome spraying operations, and increased cost of spraying

Inactive Publication Date: 2015-04-29
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the combined use of insecticides and fungicides will lead to cumbersome spraying operations. It is necessary to measure one or more insecticides and one or more fungicides according to a specific ratio, and the cost of spraying will increase accordingly. There are many types of drugs, and the amount of drug residues on plants will increase accordingly

Method used

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  • Methoxyimino phenylacetate compounds containing nitrohydrazinecarboximidamide structures as well as preparation method and application of methoxyimino phenylacetate compounds
  • Methoxyimino phenylacetate compounds containing nitrohydrazinecarboximidamide structures as well as preparation method and application of methoxyimino phenylacetate compounds
  • Methoxyimino phenylacetate compounds containing nitrohydrazinecarboximidamide structures as well as preparation method and application of methoxyimino phenylacetate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1, 2-(2-((1-(N′-nitroamidino)-2-pentylidene)hydrazinomethyl)-phenyl)-(E)-2-methoxyimino Preparation of methyl acetate (compound 15)

[0067] (1) Preparation of 1-nitro-3-aminoguanidine

[0068] Put a 100mL three-neck bottle in an oil bath, and put in 2.0g (19.2mmol) of nitroguanidine and 25mL of water in sequence. While heating to 55° C. under magnetic stirring, 1.3 g (21.6 mmol) of 85% hydrazine hydrate was slowly added dropwise from the dropping funnel. Keep the material temperature at 55°C and continue the reaction for 15 minutes. When the nitroguanidine solid dissolves and turns into an orange-yellow clear liquid, quickly cool it in an ice-salt water bath, and slowly add concentrated hydrochloric acid dropwise to adjust the pH to 5-6, and continue to cool in an ice-salt water bath overnight. Filter under reduced pressure and dry naturally in a fume hood. Recrystallized with water to obtain 1.6 g of light yellow crystals, yield 70%, melting point 191-192°...

Embodiment 2

[0080] Example 2, 2-(2-((1-(N'-nitroamidino)-2-(4-nitrobenzylidene)hydrazinomethyl)-phenyl)-(E)-2 -Methoxyimine

[0081] Preparation of methyl glycolate (compound 5)

[0082] (1) Preparation of 1-nitro-4-(4-nitrobenzaldehyde) aminoguanidine

[0083] Into a 250mL three-neck flask, 11.9g (0.1mol) of 1-nitro-3-aminoguanidine, 100mL of anhydrous methanol and 0.6mL of glacial acetic acid were successively added. Heating to boiling under magnetic stirring, slowly added 9.5 g (0.11 mol) of p-nitrobenzaldehyde and 10 mL of anhydrous methanol solution dropwise from the dropping funnel. After the dropwise addition was completed, the mixture was heated to reflux and reacted at reflux for 3.5 hours. Cool down, pour into 150mL of ice water, solid precipitates out, let stand overnight. The obtained crude product was recrystallized from ethyl acetate to obtain a yellow solid with a yield of 95% and a melting point of 264-266°C.

[0084] The structural characterization data are as follow...

Embodiment 3

[0091]Example 3.2-(2-((1-(N′-nitroamidino)-2-(isopropylidene)hydrazinomethyl)-phenyl)-(E)-2-methoxyimino Acetic acid

[0092] Preparation of methyl ester (compound 28)

[0093] (1) Preparation of 1-nitro-4-acetone aminoguanidine

[0094] In a 250mL three-necked flask, 11.9g (0.1mol) of 1-nitro-3-aminoguanidine, 18.4g (0.4mol) of acetone, 100mL of anhydrous methanol and 2mL of concentrated hydrochloric acid were successively added. Heat to reflux for 5 hours with magnetic stirring. Stand to cool, concentrate the solution to saturation, a large number of colorless crystals precipitate out, stand overnight, filter with suction, rinse with water:alcohol=2:1 solution to obtain 11.5g of white solid, yield 80%, melting point 164-166°C .

[0095] The structural characterization data are as follows:

[0096] 1.92(s,3H,CH 3 ),1.99(s,3H,CH 3 ), 7.99 (brs, 1H, =NNH-), 8.64 (brs, 1H, -NH-NO 2 ), 10.76 (s, 1H, -C=NH).

[0097] (2) 2-(2-((1-(N′-nitroamidino)-2-(isopropylidene)hydraz...

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Abstract

The invention provides methoxyimino phenylacetate compounds containing nitrohydrazinecarboximidamide structures as well as a preparation method and an application of the methoxyimino phenylacetate compounds. The structural formula of each compound is represented as the formula I, wherein R1 is H, C1-C10 saturated or unsaturated aliphatic hydrocarbon, phenyl, substituted phenyl, pyridine-2-yl, substituted pyridine-2-yl, pyridine-3-yl, substituted pyridine-3-yl, pyridine-4-yl, substituted pyridine-4-yl, thiazole-2-yl, substituted thiazole-2-yl, furan-2-yl, substituted furan-2-yl, benzyl, substituted benzyl, phenethyl, substituted phenethyl, 2-hydroxy-1-naphthyl or 3-substituted phenyl propane-2-yl; R2 is hydrogen or C1-C10 alkyl. An insecticidal and bactericidal activity experiment proves that the compounds represented in the formula (I) have good biological activity, can effectively prevent crops from being invaded by insects and harmful bacteria and can be used as plant insecticidal and bactericidal agents.

Description

technical field [0001] The invention belongs to the technical field of agricultural chemicals, and in particular relates to a methoxyiminophenylacetate compound containing a nitroaminoguanidine structure and a preparation method and application thereof. Background technique [0002] Insecticides currently on the market only prevent and control plant pests caused by harmful insects, but have no effect on plant diseases caused by harmful bacteria; fungicides on the market only have preventive effects on plant diseases caused by harmful bacteria It has a control effect, but has no effect on plant pests caused by harmful insects. Plant diseases and insect pests often occur at the same time, which requires simultaneous killing of harmful insects and harmful bacteria on plants. The conventional method is to use one or more insecticides in conjunction with one or more fungicides to simultaneously kill Kill harmful insects and harmful germs, so as to prevent and control plant disea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C281/18C07D333/22C07D307/52C07D317/58C07D213/53A01P3/00A01P7/04
Inventor 覃兆海袁小勇马永强肖玉梅杨冬燕
Owner CHINA AGRI UNIV
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