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Pyrazole compound or salt thereof, and preparation method, herbicide composition and application thereof

A compound and pyrazole technology, applied in the field of pesticides, can solve problems such as the serious problem of barnyardgrass resistance

Active Publication Date: 2016-03-16
QINGDAO KINGAGROOT CHEM COMPOUNDS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with extensive application, the resistance problem of barnyardgrass has become more and more serious. It has been reported that a large number of barnyardgrass biotypes have developed resistance to the main barnyardgrass pesticides

Method used

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  • Pyrazole compound or salt thereof, and preparation method, herbicide composition and application thereof
  • Pyrazole compound or salt thereof, and preparation method, herbicide composition and application thereof
  • Pyrazole compound or salt thereof, and preparation method, herbicide composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] This example illustrates the specific synthesis method of compound 01 in Table 1.

[0113] Step1: Synthesis of intermediate (a)

[0114]

[0115]Measure 50 mL of acetonitrile into a 250 mL three-neck flask, place in an ice-water bath, and control the temperature between 5 and 10 °C. Weigh 3.0g (0.075mol) NaH and slowly add it into a three-necked flask, control the temperature within 10°C, then weigh 3g (0.036mol) 4-methylpyrazole and dissolve it in a small amount of acetonitrile, put it in the dropping funnel, and wait When the temperature of the system drops to about 0°C, dropwise addition begins. After the dropwise addition was complete, stirring was continued under ice-water bath conditions. After the temperature of the system is stable, weigh 10g (0.030mol) of 2-chloro-3-bromomethyl-4-thiamphenicol benzoic acid and slowly add it to the system in batches. The temperature is controlled within 10°C and stirred in an ice-water bath. HPLC followed the reaction unti...

Embodiment 5

[0125] This example illustrates the specific synthesis method of compound 05 in Table 1.

[0126] Step1: Synthesis of intermediate (d)

[0127]

[0128] Measure 50 mL of acetonitrile into a 250 mL three-neck flask, place in an ice-water bath, and control the temperature between 5 and 10 °C. Weigh 4.4g (0.11mol) of NaH and slowly add it into a three-necked flask, control the temperature within 10°C, then weigh 4.6g (0.045mol) of 4-chloropyrazole and dissolve it in a small amount of acetonitrile, put it in a dropping funnel, and wait until When the temperature of the system drops to about 0°C, dropwise addition begins. After the dropwise addition was complete, stirring was continued under ice-water bath conditions. After the temperature of the system is stable, weigh 10g (0.030mol) of 2-chloro-3-bromomethyl-4-thiamphenicol benzoic acid and slowly add it to the system in batches. The temperature is controlled within 10°C and stirred in an ice-water bath. HPLC followed the r...

Embodiment 6

[0136] Example 6 illustrates the synthesis method of compound 06 in Table 1, which is similar to Example 5 and will not be described in detail here.

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PUM

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Abstract

The invention specifically relates to a pyrazole compound or salt thereof, and a preparation method, a herbicide composition and application thereof, belonging to the field of pesticide. The pyrazole compound or salt thereof has a structure as shown in a formula (I). In the formula (I), R is as defined in the specification, wherein R', R'' and R''' represent hydrogen atoms, C1-4 alkyl groups, C1-4 halogenated alkyl groups, C1-4 alkyloxy groups or halogen, and may be same or different; R1 represents a C1-3 alkyl group; R2 represents a hydrogen atom or a C1-4 alkyl group; and R3 is hydrogen atom, a C1-6 alkyl group, a substitutable phenyl group, a substitutable pyridyl group, a substitutable alkenyl group, a substitutable alkynyl group, a C1-6 alkylcarbonyl group, a C1-6 alkyloxycarbonyl group, a C1-6 alkylcarbonylmethyl group or the like. The pyrazole compound or salt thereof shows excellent herbicide effect on barnyard grass, is safe to paddy rice during application after seedling emergence, and more surprising, also exerts outstanding effect on barnyard grass with resistance to main barnyard grass herbicides like penoxsulam, quinclorac, cyhalofop butyl and propanil.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a pyrazole compound or a salt thereof, a preparation method, a herbicide composition and use. technical background [0002] Barnyardgrass is the most important weed in rice fields, especially with the development of direct seeding technology, the control of barnyardgrass has become the key to planting benefits, although a large number of barnyardgrass control agents have been developed, such as ALS inhibitors (pentafluorosulfone ACCe inhibitors (cyhalofop-methyl, fenoxaprop-methyl, fenoxaprop-p-p-1, cycloclofenone, etc.). However, with extensive application, the resistance problem of barnyardgrass is becoming more and more serious. It is reported that a large number of barnyardgrass biotypes have developed resistance to the main barnyardgrass pesticides. Therefore, there is an urgent need to develop herbicides that do not have cross-resistance to the current mainstream barn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D231/20C07D231/16A01N43/56A01P13/00A01P21/00
CPCA01N43/56C07D231/12C07D231/16C07D231/20A01N25/00C07C22/04C07C23/08C07D401/14C07D231/18C07D403/10C07D403/12C07C231/12
Inventor 连磊征玉荣何彬彭学岗金涛崔琦
Owner QINGDAO KINGAGROOT CHEM COMPOUNDS CO LTD
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