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2,4-dihalogen-6-(c2-c3-alkyl)-phenyl substituted tetramic acid derivatives

A halogenated alkyl, alkyl technology, applied in the field of 2,4-dihalogen-6-(C2-C3-alkyl) phenyl substituted tetramic acid derivatives, can solve the compatibility is not always sufficient, etc. question

Inactive Publication Date: 2006-04-19
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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, add 5.03g of the compound of formula II-1 in 10ml anhydrous dimethylformamide solution to 2.92g (0.023mol) potassium tert-butoxide in 8ml anhydrous dimethylformamide solution, and 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, the precipitate was filtered off with suction and dried. Then the product was 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 general preparation method, the following compound of formula (I-a) was obtained:

[0872]

[0873] Example

serial number

X

Y

Z

D

A

B

Fp.℃

isomer

I-a-2

Cl

Cl

C 2 H 5

H

-(CH 2 ) 2 -CHCH 3 -(CH 2 ) 2 -

＞220

β

...

Embodiment I-b-1

[0881]

[0882] 0.5ml (3.6mmol) of triethylamine was added to 1.3g of the compound of Example I-a-1 in 30ml 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. The completion of the reaction was detected 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 then the solvent was evaporated. 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 general preparation method, the following compound of formula (I-b) was obtained:

[0886]

[0887] Example

serial number

X

Y

Z

D

A

B

R 1

Fp.℃

isomer

...

Embodiment I-c-1

[0897]

[0898] At 0-10°C, a solution of 0.6ml (0.006mol) ethyl chloroformate in 50ml of dry dichloromethane was added dropwise to 2.34g of the compound of Preparation Example Ia-14 in 50ml of dry dichloromethane and 0.84ml 6mmol) in triethylamine. The mixture was stirred at room temperature until the reaction was complete (checked by thin layer chromatography).

[0899] Then the solvent was evaporated, 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 general preparation method, the following compound of formula (I-c) was obtained:

[0902]

[0903]

[0904] Example

serial number

X

Y

Z

D

A

B

M

R 2

Fp.℃

isomer

I-...

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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

Technical field [0001] 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 [0002] 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). However, the biological activities of the above compounds have not been reported yet. [0003] EP-A-0 262 399 and GB-A-2 266 888 disclose compounds with similar structures (3-...

Claims

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Application Information

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IPC IPC(8): C07D207/38C07D209/54C07D309/14C07C255/03C07D471/04C07D487/04C07D491/10C07D513/04A01N43/16A01N43/36A01N43/38A01N43/90C07C255/29C07C255/31C07D207/16C07D209/94C07D209/96C07D279/12
CPCC07C255/29C07D279/12C07D309/14C07D207/16C07D209/96C07D487/04C07D209/94C07D513/04C07C2101/02C07D207/38C07D491/10C07C255/31C07C2601/02A01N43/36
Inventor C·埃尔德伦(已死亡)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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