Trifluoromethylpicolinamide derivative containing chiral thioether structure and application thereof

Abstract

The invention discloses a trifluoromethylpicolinamide compound containing a chiral thioether structure and an application thereof. The general formula of the structure of the trifluoromethylpicolinamide compound is shown as I in the specification. The range of substituents in the formula is as defined in the claims. The compound (I) has good insecticidal activity and plant virus resisting activity, can be used for preventing and treating plutella xylostella, armyworm, ostrinia nubilalis and other pests, and can also be used for preventing and treating TMV and other plant virus diseases.

Description

technical field

[0001] The invention relates to the field of agricultural chemicals, in particular to a trifluoromethylpicolinamide derivative containing a chiral thioether structure and its application in insecticide and antivirus. Background technique

[0002] In the creation of new green pesticides, fluorine-containing pesticides have been a hot research area. Fluorine atoms have unique properties such as electronic effects, hydrogen-like analog effects, barrier effects, and fat-soluble osmotic effects, and are more and more widely used in the fields of medicinal chemistry, natural product chemistry, pesticide chemistry, and fine chemicals (Yang Jichun, et al. . Pesticides, 2011, 4, 289-295). According to incomplete statistics, the fluorine-containing compounds in the new varieties of pesticides developed in the past 10 years are as high as 50%, and fluorine-containing pesticides have become the main direction of development and application in the pesticide industry (Yan...

Examples

Embodiment 1

[0036] Embodiment 1: Preparation of 1701S

[0037] first step:

[0038] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition, 2-amino-3-methyl-5-chlorobenzoic acid (1.3mmol) was added in one go, then slowly added pyridine (4mmol) with a constant pressure dropping funnel, 5ml of acetonitrile was added, and the dropwise addition was completed Finally, slowly add methanesulfonyl chloride (2mmol) with a constant pressure dropping funnel. After the dropwise addition is complete, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0039] Step two:

[0040] Add trifluoromethylpyridoxazinone (1mmol) and 10ml of acetonitrile to start...

Embodiment 2

[0042] Embodiment 2: Preparation of 1701R

[0043] first step:

[0044] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition, 2-amino-3-methyl-5-chlorobenzoic acid (1.3mmol) was added in one go, then slowly added pyridine (4mmol) with a constant pressure dropping funnel, 5ml of acetonitrile was added, and the dropwise addition was completed Finally, slowly add methanesulfonyl chloride (2mmol) with a constant pressure dropping funnel. After the dropwise addition is complete, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0045] Step two:

[0046] Add trifluoromethylpyridine oxazinone (1mmol) and 10ml of acetonitrile to s...

Embodiment 3

[0049] Embodiment 3: Preparation of 1702S

[0050] first step:

[0051] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition was completed, 2-amino-3-methylbenzoic acid (1.3mmol) was added in one go, then pyridine (4mmol) was slowly added into the constant pressure dropping funnel, 5ml of acetonitrile was added, after the dropwise addition was completed, the Slowly add methanesulfonyl chloride (2mmol) into the dropping funnel. After the dropwise addition, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0052] Step two:

[0053] Add trifluoromethylpyridoxazinone (1mmol) and 10ml of acetonitrile to start stirring, and slow...

technical field

[0001] The invention relates to the field of agricultural chemicals, in particular to a trifluoromethylpicolinamide derivative containing a chiral thioether structure and its application in insecticide and antivirus. Background technique

[0002] In the creation of new green pesticides, fluorine-containing pesticides have been a hot research area. Fluorine atoms have unique properties such as electronic effects, hydrogen-like analog effects, barrier effects, and fat-soluble osmotic effects, and are more and more widely used in the fields of medicinal chemistry, natural product chemistry, pesticide chemistry, and fine chemicals (Yang Jichun, et al. . Pesticides, 2011, 4, 289-295). According to incomplete statistics, the fluorine-containing compounds in the new varieties of pesticides developed in the past 10 years are as high as 50%, and fluorine-containing pesticides have become the main direction of development and application in the pesticide industry (Yan...

Examples

Embodiment 1

[0036] Embodiment 1: Preparation of 1701S

[0037] first step:

[0038] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition, 2-amino-3-methyl-5-chlorobenzoic acid (1.3mmol) was added in one go, then slowly added pyridine (4mmol) with a constant pressure dropping funnel, 5ml of acetonitrile was added, and the dropwise addition was completed Finally, slowly add methanesulfonyl chloride (2mmol) with a constant pressure dropping funnel. After the dropwise addition is complete, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0039] Step two:

[0040] Add trifluoromethylpyridoxazinone (1mmol) and 10ml of acetonitrile to start...

Embodiment 2

[0042] Embodiment 2: Preparation of 1701R

[0043] first step:

[0044] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition, 2-amino-3-methyl-5-chlorobenzoic acid (1.3mmol) was added in one go, then slowly added pyridine (4mmol) with a constant pressure dropping funnel, 5ml of acetonitrile was added, and the dropwise addition was completed Finally, slowly add methanesulfonyl chloride (2mmol) with a constant pressure dropping funnel. After the dropwise addition is complete, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0045] Step two:

[0046] Add trifluoromethylpyridine oxazinone (1mmol) and 10ml of acetonitrile to s...

Embodiment 3

[0049] Embodiment 3: Preparation of 1702S

[0050] first step:

[0051] 3-Chloro-5-trifluoromethylpicolinic acid (1mmol), pyridine (4mmol) and 10ml of acetonitrile were added to a 50ml three-neck flask, stirred under an ice-salt bath, and methanesulfonyl chloride ( 2mmol), after the dropwise addition was completed, 2-amino-3-methylbenzoic acid (1.3mmol) was added in one go, then pyridine (4mmol) was slowly added into the constant pressure dropping funnel, 5ml of acetonitrile was added, after the dropwise addition was completed, the Slowly add methanesulfonyl chloride (2mmol) into the dropping funnel. After the dropwise addition, remove the ice bath. After the reaction is complete, extract the reaction solution with dichloromethane and water, mix the organic layer, and use V 石油醚 :V 乙酸乙酯 =10:1 crosses column and obtains trifluoromethylpyridine oxazinone;

[0052] Step two:

[0053] Add trifluoromethylpyridoxazinone (1mmol) and 10ml of acetonitrile to start stirring, and slow...

Images