CN105153037B - A kind of azoles worm sulfonylurea compound - Google Patents

Abstract

The invention discloses a fenflumezole compound, the structure of which is shown in formula I: The compound of formula I has excellent insecticidal activity and can be used for the control of agricultural or forestry pests.

Description

A kind of Fenflumezin compound

Technical field The present invention belongs to the field of agricultural insecticides, and relates to a fenflumezin compound and its application.

Background Art The resistance of pests is the main source of their difficulty in control, and the development of new control agents is an important way to control resistance. US5039693 discloses the preparation and insecticidal activity of the following compound (KC). The product name of the compound is tofenpyrad, and it has good control effects on pests such as diamondback moth, thrips and tea green leafhopper.

In the prior art, there is no disclosure of the Fenflumezin compound and its insecticidal properties as shown in the present invention.

Contents of the invention

The object of the present invention is to provide a pyraflufenuron compound with novel structure, good comprehensive performance and low control cost, which can be used for the control of major agricultural or forestry pests.

Technical scheme of the present invention is as follows:

A fenflumezole compound, the structure of which is shown in formula I:

The compounds of the present invention can be prepared by the following methods.

The above two raw materials are reacted in dichloroethane solvent at room temperature to obtain the compound of formula I, and the preparation of pyrazole acyl isocyanate in the above reaction is shown in the examples of the present invention.

Advantages and positive effects of the present invention: the compound of the present invention, Fenfenpyradim, inherits the structural characteristics of Tofenpyrad (KC) insecticides, and has the active group of urea insecticides, and has a different killing effect from Tofenpyradram. Insect mechanism, especially for pests that have developed resistance to tofenpyrad. Moreover, the compound is easy to degrade, has good environmental compatibility, and has the potential to be developed into an ultra-efficient green and environment-friendly insecticide.

When the compound of the present invention is used to control insect pests, it can be used alone or in combination with other active substances to improve the comprehensive function of the product.

The present invention also includes an insecticidal composition using Compound I as an active component, and the weight percentage of the active component in the composition is as high as 1-95%, and the insecticidal composition also includes agricultural or forestry pesticides. acceptable carrier.

detailed description

The following synthetic examples and bioassay results can be used to further illustrate the present invention, but are not meant to limit the present invention.

synthetic example

Example 1, the preparation of compound I

(1) Synthesis of 4-chloro-3-ethyl-1-methylpyrazole-5-carbonyl chloride

Add 18.85g (0.1mol) of the raw material 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid into a 250mL reaction flask, add 100g of toluene, stir for 5min, and drop in 23.8g (0.2 mol), slowly warming up to reflux. After reflux for 4 hours, toluene and excess thionyl chloride were distilled off under reduced pressure to obtain 20.70 g of a brownish-red oil, with a yield of 100%.

(2) Synthesis of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide

Add 80g of 40% ammonia water to a 250mL reaction bottle, control the temperature in an ice bath below 0°C, add 20.70g (0.1mol) of 4-chloro-3-ethyl-1-methylpyrazole-5-carbonyl chloride dropwise, and drop , reacted at room temperature for 0.5h, filtered with suction, and washed the filter cake with 20mL×2 tap water to obtain 15g of white solid with a yield of 80%.

(3) Synthesis of 4-chloro-3-ethyl-1-methylpyrazole-5-formyl isocyanate

Add 18.75g (0.1mol) of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide, 100mL of dichloroethane, and dropwise add 31.75g (0.25mol) of oxalyl chloride into a 250mL reaction flask After the drop, the temperature was raised to reflux for 10 h, and the dichloroethane and excess oxalyl chloride were distilled off under reduced pressure to obtain 21.35 g of a brown oil, with a yield of 100%.

(4) Synthesis of compound I

Add 25g of dichloroethane, 2.13g (0.01mol) of p-methoxybenzylamine to a 100mL reaction flask, and dropwise add 2.35g of 4-chloro-3-ethyl-1-methylpyrazole-5-formyl isocyanate (0.011mol), after the dropwise reaction at room temperature for 3 hours, 2.6 g of white solid was obtained by suction filtration, with a yield of 61%. Melting point: 100-103°C.

¹ H NMR of Compound I (500MHz, DMSO-d ₆ ), δ(ppm): 1.153-1.183(t, 3H), 2.283(s, 3H), 2.525-2.570(q, 2H), 3.866(s, 3H ), 4.375-4.387(d, 2H), 6.896-6.913(d, 2H), 6.935-6.952(d, 2H), 7.175-7.192(d, 2H), 7.328-7.345(d, 2H), 8.621(s , 1H), 10.601(s, 1H).

Bioactivity assay

Example 2 Determination of insecticidal activity

Determination of Plutella xylostella activity:

Use the leaf dipping method. The leaf dipping method proposed by the International Resistance Action Committee (IRAC) was used. Use the prepared drug solution to be tested, dip the cabbage leaves with straight ophthalmic tweezers for 3-5 seconds, shake off the remaining liquid, one piece at a time, a total of 3 pieces for each sample, and place them on the processing paper according to the order of sample marking superior. After the liquid medicine dries, put it into a marked 10 cm long straight tube, insert 30 2nd instar diamondback moth larvae, and cover the tube mouth with gauze. The test treatment was placed in the standard treatment room, and the result of 48h inspection was that the needle was pulled out and the insect body was lightly touched, and those who did not move were considered dead. Calculate the mortality rate. The experiment was repeated 3 times and the average value was taken. The results are shown in Table 1.

Table 1 Results of determination of activity against diamondback moth

The results in Table 2 show that the compound of the present invention, Fenflumezed, is significantly better than the comparative agent, Fenpyrad (KC), against Plutella xylostella.

Claims (3)

1. a kind of azoles worm sulfonylurea compound, structure is shown in formula I：

2. according to a kind of purposes of azoles worm sulfonylurea compound described in claim 1, it is characterised in that compound of formula I is used as desinsection Agent, prevents and treats crop pests.

3. a kind of Pesticidal combination, is that can be connect in active component and agricultural or forestry containing the compound of formula I described in claim 1 The carrier received.