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Isoindole compounds and uses thereof

A compound, the technology of isoindole, which is applied in the field of isoindole compounds and their applications, can solve problems not involved in the preparation and application of isoindole compounds

Active Publication Date: 2009-04-15
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The prior art does not relate to the preparation and application of isoindole compounds containing 2-substituted acetic acid unsaturated esters as shown in the present invention

Method used

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  • Isoindole compounds and uses thereof
  • Isoindole compounds and uses thereof
  • Isoindole compounds and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Embodiment 1: the synthesis of compound 1

[0107]

[0108] Add 2.0 g (21 mmol) of chloroacetic acid, 20 ml N,N-dimethylformamide, 2.8 g (20 mmol) of potassium carbonate and 3.0 g (20 mmol) of propargyl bromide in sequence in a 100 ml reaction flask. mol), stirred at room temperature for 3 hours. The reaction solution was poured into 20 ml of water, extracted with 150 ml of ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the organic solution was concentrated under reduced pressure to obtain 1.8 g of propargyl chloroacetate, a yellow liquid, and the yield : 69%.

[0109]

[0110] Add successively 0.36 grams of substituted benzoic acid (1 mmol, made with reference to the operating method provided by EP68822), 5 milliliters of N,N-dimethylformamide, 0.17 grams of potassium carbonate (1.2 mmol) in a 100 ml reaction flask, 0.40 g (3 mmol) of propargyl chloroacetate was stirred at room temperature for 1 hou...

Embodiment 2

[0111] Embodiment 2: the synthesis of compound 16

[0112]

[0113] Add 1.06 g (10.0 mmol) of lactic acid, 10 ml of N, N-dimethylformamide, 1.46 g (11.0 mmol) of potassium carbonate, and 0.8 g (11.0 mmol) of allyl chloride in a 100 ml reaction flask. . Stir at room temperature for 4 hours. The reaction solution was poured into 20 ml of water, extracted with 100 ml of ethyl acetate, the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.95 g of allyl lactate, a yellow oil , yield 73%.

[0114]

[0115] Add 0.62 g (2.0 mmol) of substituted benzoic acid, 10 ml of dichloromethane, 0.38 g (3.0 mmol) of oxalyl chloride and 1 drop of N, N-dimethylformamide successively in a 100 ml reaction flask, and stir at room temperature 1 hour. The reaction solution was concentrated under reduced pressure to obtain 0.67 g of substituted benzoyl chloride (hereinafter referred to as ...

Embodiment 3

[0118] Embodiment 3: the synthesis of compound 23

[0119]

[0120] Add 25 grams (0.2 moles) of S-lactic acid, 59 grams (1 mole) of propylene alcohol, and 50 milliliters of benzene in a 500 milliliter reaction flask in sequence, then add 1 milliliter of concentrated sulfuric acid, heat to reflux, and use a water separator to separate the generated water, heated to reflux for 12 hours and the reaction was basically complete. The solvent was removed under reduced pressure to obtain a black oil. Distilled under reduced pressure, collecting 50-55 ° C fraction (2mmHg). 15 g of S-allyl lactate was obtained as a colorless liquid, yield: 56%. [α] D 20 =-9.8° (c=0.2, CHCl 3 ).

[0121]

[0122] Add 0.40 g (3.0 mmol) of S-allyl lactate, 10 ml of dichloromethane and 0.32 g (3.2 mmol) of triethylamine successively in a 100 ml reaction flask, and add 0.65 g (2.0 mmol) of acid chloride dropwise A solution of dichloromethane (10 ml) was added dropwise and stirred at room tempera...

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Abstract

The invention discloses an isonindole compound containing 2-substituent acetic acid unsaturated ester with novel structure as shown in general formula (I), in the formula: X is chosen from H or F; R1 is chosen from H or C1-C6 alkyl; R2 is chosen from H or C1-C6 alkyl; Q is chosen from substitutional alkenyl or alkynyl; and a stereoisomer thereof. The compound with the general formula (I) has postemergence herbicide activity and is safe to corn, wheat, and rice.

Description

technical field [0001] The invention belongs to the field of herbicides, and in particular relates to an isoindole compound and its application. Background technique [0002] Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides, people's awareness of ecological environment protection has been continuously strengthened. The emphasis on the issue of whereabouts continues to increase. With the gradual reduction of the world's arable land, the continuous growth of the population and the increase in the demand for food, people are forced to rapidly develop agricultural production technology, improve and improve the farming system, and need to continuously invent new and improved herbicidal compounds and compositions. [0003] JP 60109563 discloses that the following isoindoles have herbicidal activity: [0004] [0005] Among them, R=Cl, Br; R 1 = H, F, Cl; R 2 = alkyl. [0006] WO 8801265 disclo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48A01N43/38A01P13/00
CPCC07D209/48A01N37/46
Inventor 李斌张勇崔东亮于海波袁静白丽萍
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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