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Hexahydrotriazine compounds and insecticides

a technology of hexahydrotriazine and compounds, applied in the field of hexahydrotriazine compounds and insecticides, can solve the problems of not producing phytotoxicity and compound not producing phytotoxicity, and achieve the effects of effective control of harmful insects, low toxicity, and reduced amoun

Inactive Publication Date: 2001-11-29
KANESHO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0019] In the preparation process (a), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting, in a solvent, a compound represented by the general formula (II); with a compound represented by the general formula (III), such as bis(chloromethyl)methylamine, bis(chloromethyl)ethylamine and bis(chloromethyl)propylamine, in the presence of a basic material.
[0026] In the preparation process (c), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (V) with a compound represented by the general formula (VI) in the presence of a basic material in an inert solvent.
[0030] The compounds of this invention, which are represented by the general formula (I) set forth above, have strong insecticidal activity against various harmful insects, including Hemiptera, Lepidoptera, Coleoptera, Diptera, Orthoptera and Isoptera, and yet are low in toxicity to human beings and animals and do not produce phytotoxicity in various plants, and thus can be practically used as superior insecticides.

Problems solved by technology

Lastly, such novel compounds do not produce phytotoxicity in various plants.
Lastly, such improved insecticides do not produce phytotoxicity in various plants.

Method used

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  • Hexahydrotriazine compounds and insecticides
  • Hexahydrotriazine compounds and insecticides
  • Hexahydrotriazine compounds and insecticides

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1-,3,5-triazine

[0035] 0.6 g of 1-(2-chloro-5-pyridylmethyl)-3-nitroguanidine and 0.4 g of bis(chloromethyl)methylamine were suspended in dried THF. To the suspension, a solution of 0.52 g of triethylamine in THF was added dropwise with cooling. The reaction mixture was stirred for 1 hour, and then poured into ice water. The mixture was extracted with dichloromethane. After the extract was dried over anhydrous magnesium sulfate, dichloromethane was distilled off. The residue was recrystallized from methanol to obtain 0.78 g of the title compound. This compound is No. 1 in Table 1. m.p.: 150-154.degree. C.

synthesis example 2

Synthesis of 1-(2-chloro-5-pyridylmethyl)-5-ethyl-2-nitroiminohexahydro-1,-3,5-triazine

[0036] To a stirring mixture of 1 g of 1-(2-chloro-5-pyridylmethyl)-3-nitr-oguanidine, 0.28 g of 70% ethylamine in water and 20 ml of ethanol, 0.71 g of 37% formalin solution was added dropwise with heating. The reaction mixture was heated under reflux for two hours. After being allowed to cool to room temperature, the crystals formed, which were filtrated off and recrystallized from methanol to obtain 1.15 g of the title compound. This compound is No. 2 in Table 1. m.p.: 124-125.degree. C.

synthesis example 3

Synthesis of 1-(2-chloro-5-pyridylmethyl)-3,5-dimethyl-2-nitroiminohexahyd-ro-1,3,5-triazine

[0037] 1 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine was dissolved in 20 ml of dried DMF. To the solution, 0.27 g of 60% sodium hydride was added with cooling. The mixture was stirred for 1 hour at room temperature until evolution of hydrogen was ceased and then the mixture was heated with stirring further for 1 hour at 50.degree. C. To the mixture, a solution of 0.9 g of 2-chloro-5-pyridylmethylchloride in 8 ml of dried DMF was added dropwise at 40-50.degree. C. After this addition, the reaction mixture was heated with stirring it for two hours at 70-80.degree. C. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain 1.3 g of the title compound. This compound is No.5 in Table 1. m.p.: 116-117.degree. C.

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Abstract

Hexahydrotriazine compounds of the formula: are prepared by reacting a compound of the formula: with a di(monohalomethyl)amine compound or a primary amine compound in combination with formalin or paraformaldehyde, or by reacting a hexahydrotriazine derivative with a compound of the formula: R2CH2-Y-.

Description

[0001] 1. Field of the Invention[0002] The present invention relates to hexahydrotriazine compounds, a process for preparing the same and insecticides containing the same as active ingredients. The hexahydrotriazine compounds provided by this invention are represented by the following general formula (I): 3[0003] wherein R stands for lower alkyl or lower alkenyl; R.sub.1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by 4[0004] and R.sub.2 stands for a group indicated by 5[0005] 2. Prior Art[0006] A variety of chemicals have been developed and used as insecticides for controlling harmful insects. Representative examples of such chemicals are organic phosphorous compounds, carbamate compounds and synthetic pyrethroids. However, by the repeated use of these insecticides, many harmful insects have acquired resistance to these chemicals, thus making it difficult to control such insects. On the other hand, although some conventional insecticides have ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N51/00C07D401/06C07D401/14C07D417/06
CPCA01N51/00C07D401/06C07D401/14C07D417/06
Inventor WU, FRANKKARIYA, AKINORIKATSUYAMA, NORIYOSHITSUJI, ATSUSHITAKASUKA, KIYOSHISEGAMI, SHIGENORINANJO, KATSUMISATO, JUNKO
Owner KANESHO
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