JPS6048976A - 1-(3-aminophneyl)-3-methyl-4-difluoromethyl-delta2-1,2,4- triazolin-5-one and its preparation - Google Patents

Abstract

NEW MATERIAL:1-(3-Aminophenyl)-3-methyl-4-difluoromethyl-DELTA<2>-1,2,4-tr iazoline- 5-one shown by the formula I . USE:An intermediate for agricultural chemicals, especially herbicides. PREPARATION:1-( 3-Nitrophenyl )-3-methyl-4-difluoromethyl-DELTA<2>-1,2,4-triazoline-5- one shown by the formula II is reduced to give a compound shown by the formula I . The compound shown by the formula II, for example, can be synthesized by subjecting a compound shown by the formula VI (R is lower alkyl) and a compound shown by the formula V to ring closure in an inert solvent under heating, to give a compound shown by the formula IV, reacting this compound with a compound shown by the formula III (Z is halogen) in an inert solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to triazoline derivatives and methods for producing the same.

The triazoline derivative of the present invention is represented by the structural formula (I).

This triazoline derivative is represented by the following structural formula (■): 1-(5-nitrophenyl)-3-methyl-4-difluoromethyl-Δ-'? It is produced by reducing 214-triazolin-5-one.

The compound of the present invention is a new compound that has not been described in any literature, and is a pesticide,
It is an important intermediate for producing compounds useful as specific herbicides, and the present invention also provides a method for producing it.

For example, the production method of the present invention can be diagrammatically expressed as follows.

([)(1) That is, 1-(5-nitrophenyl)-3-methyl-4-difluoromethyl-Δ"-1 represented by the structural formula (It)
, 2,4-triazolin-5-one with a reducing agent in the presence or absence of a suitable solvent to obtain the structural formula (1
) can be obtained.

The solvent that can be used in the reaction of the present invention may be any solvent as long as it does not significantly inhibit the reaction, and examples thereof include alcohols such as methanol and ethanol, water, and the like.

These solvents can be used alone or in combination. Furthermore, the aqueous solution of the acid used as the reducing agent shown below may be used as it is as a solvent.

Examples of the reducing agent include metal-acid and sodium polysulfide. Examples of metal-acid reducing agents include metals such as iron, tin, and zinc, and acids such as hydrochloric acid, sulfuric acid, and acetic acid, and these may be used in combination.

The amount of the reducing agent added is 1-(5
-nitrophenyl)-5-methyl-4-difluoromethyl-Δ"-1,2,4-) riazolin-5-one, the metal is 1 to 1 [10 mol, the acid is 005 to 1
It may be used by appropriately selecting from the range of 0.0 mol.

The reaction temperature may be selected from the range of room temperature to 100°C.

The reaction time may be selected from the range of 1 to 10 hours.

Further, the reduction reaction may be carried out by a catalytic hydrogenation method in the presence of a catalyst, whereby the compound of the present invention (summer) can be synthesized.

After the reaction is completed, the desired product can be obtained by extraction or filtration from the reaction solution and recrystallization from inbanol.

1-(3-nitrophenyl)-3-7i thyl-a-difluoromethyl-Δ2-1.
2.4-) Riazolin-5-one can be synthesized, for example, by the following method.

(U) (However, in the formula, R represents a lower alkyl group and 2 represents a halogen atom.) That is, a compound represented by the general formula (b) and hydrazine represented by the structural formula (■) are mixed in an inert solvent. , 1- represented by the structural formula <W> by ring-closing reaction under heating.
(5-nitrophenyl)-5-methyl-Δ”-1,2,
, 4-) liazolin-5-one, and by reacting this compound (M with a compound represented by the general formula (Iff) in an inert solvent, the 1-
(3-bi)lophenyl)-3-methyl-4-difluoromethyl-Δ2-1.2.4-triazolin-5-one can be obtained.

Some examples of the present invention are shown below, but the present invention is not limited thereto.

Example 1 1-(5-nitrophenyl)-3-methyl-4-difluoromethyl-ΔZ-1, dissolved in 85 txl of concentrated hydrochloric acid.
2,4-) lyazolin-5-one a5f ((10!1
A solution of stannous chloride 3α4y (0.13M) dissolved in concentrated hydrochloric acid (85-2 mol) was gradually added at room temperature. Next, the reaction is carried out at 60 to 70°C for 1 hour. After the reaction is complete, 3
After adjusting the reaction solution to pH 1o with an aqueous solution of IJ (0% hydroxide), it is extracted with ethyl acetate, and after drying, the solvent is distilled off to obtain crystals. 7. The desired product was obtained by recrystallizing the obtained crystals from ingropanol. Get Of.

Melting point 155-154°C Yield 92.5% Example 2 l-(3-nitrophenyl)-5-methyl-4-difluoromethyl-Δ2-1.2.4-triazolin-5-one 4.9 ? (0,018 mol), iron powder 5.0 g (0
, 054 mol) and 5 Qrd of a 50% ethanol aqueous solution were refluxed and stirred, and an ethanol aqueous solution containing 0.4 ml (α005 mol) of hydrochloric acid was added dropwise over 1 hour. After completion of the dropwise addition, stirring was continued for an additional 4 hours. After the reaction is completed, the reaction solution is filtered while still warm, and the crystals precipitated from the r solution are collected and recrystallized from inglobanol to obtain the target product of #) 3.2 sF.

Melting point: 153-154°C Yield: 74. o% patent applicant
Nihon Nohyaku Co., Ltd.

Claims (2)

[Claims] (1) Structural formula (■): 1-(3-aminophenyl)-5-meth-4-difluoromethyl-Δ2-12.4-) liazolin-5-one. (2) Structural formula (U): Characterized by reducing 1-(6-nitrophenyl)-3-methyl-4-difluoromethyl-Δ2-12.4-) liazolin-5-one Structural formula (I)
: A method for producing 1-(3-aminophenyl)-3-methyl-4-difluoromethyl-Δ2-12.4-) liazolin-5-one.