2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives

A brbrn-c3h7ch3, compound technology, applied in the field of tetramic acid derivatives substituted by 2,4-dihalogen-6-(C2-C3-alkyl)phenyl, can solve the problem that the compatibility is not always enough, etc. question

Inactive Publication Date: 2008-05-07
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the activity and activity spectrum of the aforementioned compounds, especially at low applied doses and concentrations, are not always fully satisfactory
Moreover, the compatibility of the above-mentioned known compounds with crops is not always sufficient

Method used

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  • 2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives
  • 2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives
  • 2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I-a-1

[0867]

[0868] At 0 to 20° C., a solution of 5.03 g of the compound of formula II-1 in 10 ml of anhydrous dimethylformamide was added to a solution of 2.92 g (0.023 mol) of potassium tert-butoxide in 8 ml of anhydrous dimethylformamide, and in The resulting mixture was stirred at 20°C.

[0869] The reaction solution was poured into 80 ml of ice water, and then the pH of the solution was adjusted to 1 with concentrated hydrochloric acid at 0-20° C., and the precipitate was filtered off with suction and dried. The product was then triturated with MTB ether / n-hexane.

[0870] Yield: 3.79 g (80% of theory), melting point: 245°C.

[0871] Similar to Example (I-a-1) and according to its generally described preparation method, the compound of the following formula (I-a) is obtained:

[0872]

[0873] Example

Numbering

X

Y

Z

D

A

B

Fp.℃

isomer

I-a-2 ...

Embodiment I-b-1

[0881]

[0882] 0.5 ml (3.6 mmol) of triethylamine was added to 1.3 g of the compound of Example I-a-1 in 30 ml of anhydrous ethyl acetate. A solution of 0.38 ml (0.0036 mmol) of isobutyryl chloride in 5 ml of anhydrous ethyl acetate was added dropwise under reflux.

[0883]The mixture was stirred at reflux. Reaction completion was checked by thin layer chromatography. The solvent was removed with a rotary evaporator, the residue was dissolved in dichloromethane and washed twice with 50 ml of 0.5N NaOH solution, dried and the solvent was evaporated off. The product was then recrystallized from MTB ether / n-hexane.

[0884] Yield: 0.81 g (55% of theory), melting point: 155°C.

[0885] Similar to Example (I-b-1) and according to its described general preparation method, the compound of the following formula (I-b) is obtained:

[0886]

[0887] Example

Numbering

X

Y

Z

D

A

B

R 1

...

Embodiment I-c-1

[0897]

[0898] At 0-10° C., a solution of 0.6 ml (0.006 mol) ethyl chloroformate in 50 ml of anhydrous dichloromethane was added dropwise to 50 ml of anhydrous dichloromethane and 0.84 ml ( 6mmol) in triethylamine. The mixture was stirred at room temperature until the reaction was complete (checked by TLC).

[0899] The solvent was then evaporated off, the residue was dissolved in dichloromethane and washed twice with 50 ml of 0.5N NaOH solution, dried, then the solvent was evaporated and the residue was recrystallized from MTB ether / n-hexane.

[0900] Yield: 2.2 g (79% of theory), melting point: 114°C.

[0901] Similar to Example (I-c-1) and according to its described general preparation method, the compound of the following formula (I-c) is obtained:

[0902]

[0903]

[0904] table (continued)

[0905] Example

Numbering

X

Y

Z

D

A

B

M

R 2

Fp.℃

isom...

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Abstract

The invention relates to novel 2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives of formula (I), wherein A, B, D, G, X, Y and Z have the above mentioned meaning. The invention also relates to several methods and intermediate products for the production and use thereof as pesticides and / or herbicides, in addition to selective herbicidal agents which contain 2.4-dihalogen-6-(C2-C3-alkyl)-phenyl substituted tetramic acid derivatives and at least one compound which improves the compatibility of cultivated plants.

Description

[0001] This application is a divisional application of the invention patent application with application number 200480007508.9 and the filing date being January 7, 2004. Technical field [0002] The present invention relates to novel 2,4-dihalogen-6-(C 2 -C 3 -Alkyl)phenyl-substituted tetramicacid derivatives, involving various methods and intermediates for the preparation of the above-mentioned compounds and their use as pesticides and / or herbicides. The invention also relates to an aspect comprising 2,4-dihalogen-6-(C 2 -C 3 -Alkyl)phenyl substituted tetramic acid derivatives and on the other hand a selective herbicidal composition comprising at least one compound improving crop compatibility. Background technique [0003] 3-Acyl-pyrrolidine-2,4-dione is known to have pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). In addition, R.Schmierer and H.Mildenberger synthesized N-phenylpyrrolidine-2,4-dione (LiebigsAnn.Chem. 1985 , 1095). How...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/02C07C69/635C07D207/38C07D209/54C07D309/14C07C255/03C07D471/04C07D487/04C07D491/10C07D513/04A01N43/16A01N43/36A01N43/38A01N43/90A01P13/00A01P7/00A01P5/00C07C255/29C07C255/31C07D207/16C07D209/94C07D209/96C07D279/12
CPCC07C255/29C07D279/12C07D309/14C07D207/16C07D209/96C07D487/04C07D209/94C07D513/04C07C2101/02C07D207/38C07D491/10C07C255/31C07C2601/02A01N43/36
Inventor C·埃尔德伦R·菲舍尔S·莱尔U·施奈德M·多林格尔M·W·德鲁斯D·福伊希特P·勒泽尔O·马尔萨姆U·瓦亨多夫-诺伊曼I·维乔洛夫斯基G·博亚克R·A·迈尔斯T·奥勒M·希尔斯H·哈格曼H·克内C·H·罗辛格
Owner BAYER CROPSCIENCE AG
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