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3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines

A technology of dihydroisoquinoline and compounds, applied in organic chemistry, animal repellent, plant growth regulator, etc. 1-ylquinoline compound, no record, etc.

Active Publication Date: 2007-02-07
MITSUI CHEM AGRO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] In International Publication Pamphlet No. 00 / 42019 and International Publication Pamphlet No. 02 / 06270, 6-arylphenanthridine that forms a cyclohexane ring between the 3-position and 4-position of the dihydroisoquinoline ring is described The compound is used as a PDE4 inhibitor. In addition, in Japanese Patent Application Laid-Open No. 2003 / 171381, it is described that 6-arylfuran isoquinoline in which a dihydrofuran ring is formed between the 7-position and 8-position of the dihydroisoquinoline ring compound as an entry inhibitor, however, there is no description of a 3-dihydroisoquinolin-1-ylquinoline compound in which the isoquinoline ring is not condensed with other rings, and there is no description of a fungicide for agriculture and gardening
In addition, in Indian Journal of Chemistry 1969, 7 (10), 1010-1016, with literature 1970, 8 (6), 505-508, with literature 1985, 24B (7), 737-746 and with literature 1986, 25B ( 10), 1072-1078, the synthesis of 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinoline compounds is described, but the 3-position of the isoquinoline ring is substituted by two substituents 3-(Dihydro(tetrahydro)isoquinolin-1-yl)quinoline compounds, and there is no record about fungicides for agriculture and horticulture

Method used

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  • 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines

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Embodiment 1

[0294] 6'-Methyl-1'-quinolin-3-yl-4'H-spiro[cyclohexane-1,3'-isoquinoline] (Compound No. 1-772) (Process A)

[0295] Under ice-cooling, to quinoline-3-carbonitrile (154 mg, 1.0 mmol) in benzene (1.0 mL) was added sulfuric acid (0.4 mL) and 1-(3-methylbenzyl) cyclohexanol (204 mg, 1.0 mmol mol), stirred at 80°C for 1 hour, added water, extracted with ethyl acetate, and chromatographically separated the obtained residue to obtain 180 mg of the target compound (yield 73%).

[0296] Physical properties: oily substance.

[0297] 1 H-NMR (270MHz, CDCl 3 )δppm: 1.51-1.85 (10H, m), 2.40 (3H, s), 2.81 (2H, s), 7.02-7.14 (3H, m), 7.57 (1H, t, J=8.4Hz), 7.75 (1H , t, J = 8.4Hz), 7.86 (1H, d, J = 8.4Hz), 8.15 (1H, d, J = 8.4Hz), 8.36 (1H, s), 9.16 (1H, s). MS m / z: 340 (M + ), 325, 311, 297, 284, 244, 142, 128.

Embodiment 2

[0299] 3-(5-Fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (Compound No. 1-32) (Process A)

[0300] Under ice cooling, add 1-fluoro-(2-methylpropen-1-yl)benzene and 1-fluoro-(2-methylpropen-2-yl)benzene to a mixture of about 4 to 7 (87.3 mg, 0.58 mg mol) and quinoline-3-carbonitrile (89.6mg, 0.58mmol) in dichloroethane (0.58mL), add trifluoromethanesulfonic acid (0.52mL), stir at room temperature for 18 hours, add water, It was extracted with ethyl acetate, and the obtained residue was chromatographed to obtain 82.2 mg of the target compound (yield 47%).

[0301] Melting point: 97~100℃.

[0302] 1 H-NMR (500MHz, CDCl 3 )δppm: 1.36 (6H, s), 2.89 (2H, s), 7.03 (1H, dd, J = 1.4, 6.9Hz) 7.18-7.24 (2H, m), 7.60 (1H, t, J = 8.2Hz) , 7.77 (1H, ddd, J = 1.3, 6.9, 8.2Hz), 7.88 (1H, d, J = 8.2Hz), 8.16 (1H, d, J = 8.2Hz), 8.36 (1H, d, J = 2.1 Hz), 9.09 (1H, d, J=2.1Hz).

[0303] MS m / z: 304 (M + ), 303, 289, 248, 156.

Embodiment 3

[0305] 3-(5-Acetyl-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (Compound No. 1-114) (Step B)

[0306] To a solution of 3-(5-bromo-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (806 mg, 2.2 mmol) in toluene (0.9 mL), tris Butyl(1-ethoxyvinyl)tin (0.85mL, 2.4mmol) and dichlorobis(triphenylphosphine)coordinated palladium (15.8mg, 0.022mmol), after stirring at 100°C for 3 hours, Add dilute hydrochloric acid to temporarily make it acidic, then make it alkaline with ammonia water, filter, concentrate the filtrate, and chromatographically separate the obtained residue to obtain 647 mg of the target compound (yield 89%).

[0307] Physical properties: oily substance.

[0308] 1 H-NMR (500MHz, CDCl 3 )δppm: 1.31 (6H, s), 2.67 (3H, s), 3.13 (2H, s), 7.32 (1H, t, J = 7.6Hz), 7.37 (1H, dd, J = 1.4, 7.6Hz), 7.60 (1H, ddd, J=1.4, 6.9, 8.2Hz), 7.78 (1H, ddd, J=1.4, 6.9, 8.2Hz), 7.82 (1H, ddd, J=1.4, 7.6Hz), 7.87 (1H, d, J=8.2Hz), 8.16(1H, d, J=8.2Hz), 8.35(1H, d, J=2.1Hz), 9....

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Abstract

The invention provides compounds which exert excellent fungicidal activities against various plant diseases and are useful as active ingredients of pesticides permitting the control of rice blast and so on even in low dosages. Compounds represented by the general formula wherein R<1> and R<2> are each C1-6 alkyl or the like; R<3> and R<4> are each hydrogen, halogeno, or the like; R<5> is hydrogen, C1-6 alkyl, or the like; X is halogeno, C1-6 alkyl, or the like; Y is halogeno, C1-6 alkyl, or the like; n is an integer of 0 to 4; and m is an integer of 0 to 6.

Description

technical field [0001] The present invention relates to 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinoline compounds or salts thereof and agricultural chemicals containing them as active ingredients. Background technique [0002] In International Publication Pamphlet No. 00 / 42019 and International Publication Pamphlet No. 02 / 06270, 6-arylphenanthridine that forms a cyclohexane ring between the 3-position and 4-position of the dihydroisoquinoline ring is described The compound is used as a PDE4 inhibitor. In addition, in Japanese Patent Laid-Open No. 2003 / 171381, it is described that 6-arylfuran isoquinoline in which a dihydrofuran ring is formed between the 7-position and 8-position of the dihydroisoquinoline ring compound as an entry inhibitor, however, there is no description of a 3-dihydroisoquinolin-1-ylquinoline compound in which the isoquinoline ring is not condensed with other rings, and there is no description of an agricultural and horticultural fungicide either. In ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/42A01N43/90C07D401/14C07D409/14C07D413/14C07D498/04C07D215/04
CPCC07D498/04C07D413/14C07D409/14C07D215/04A01N43/90C07D401/04C07D405/14A01N43/42C07D405/04C07D491/04
Inventor 伊藤宽之藤原宏太森本宗嗣田中治一玉川靖驹井浩之
Owner MITSUI CHEM AGRO INC
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