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5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method

A technology of arylaminothiazole and furan phenol ether, which is applied in the field of 5-furan phenol ether compounds, can solve the problems of high toxicity and achieve good herbicidal activity

Active Publication Date: 2012-07-25
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, the commercialized derivatives of furanol, such as carbofuran, carbosulfan, carbosulfan, furanfur, and other large-tonnage carbamate pesticides have the disadvantage of high toxicity and will be gradually eliminated. Therefore, it is necessary to develop New low-toxic and high-efficiency broad-spectrum pesticide varieties to meet the needs of modern pesticides

Method used

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  • 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method
  • 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method
  • 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation reaction formula of 4-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)-5-methyl-2-anilinothiazole is as follows:

[0024]

[0025] 1), the preparation of 1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl) acetone

[0026] Under ice-water bath, add 35.6g 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran, 19.4g propionyl chloride, 30.7g aluminum trichloride and 150mL nitrobenzene, mix and stir After 5 hours, TLC monitored the reaction to the end point, the reaction solution was poured into ice water, separated into layers, the solvent was evaporated, and recrystallized from ethanol / water to obtain 34.3 g of light yellow solid, with a yield of 73.1%. m.p.74.4~75.5°C.

[0027] 2), the preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)acetone

[0028] 11.0g of 1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)acetone and 100mL of ethanol were heated and stirred, and when the temperature rose to 60°C, the Add 22.4g copper bromide in...

Embodiment 2

[0031] Preparation of 4-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)-5-methyl-2-(2-methylanilino)thiazole

[0032] The chemical structural formula is as follows:

[0033]

[0034] The operation is the same as in Example 1, and the reaction takes 2.0h. Product R f=0.54 (developing agent: ethyl acetate:petroleum ether=1:4), dried to obtain 1.16g of light yellow solid, yield 66.3%, melting point 156-158°C. LC / MS: 381.2 (M+1). 1 HNMR (CDCl 3 , 400M) δ: 1.53(s, 6H, 2×CH 3 ), 2.30(s, 3H, thiazole ring 5-CH 3 ), 2.41 (s, 3H, CH 3 ), 3.05(s, 2H, ArCH 2 ), 3.89 (s, 3H, OCH 3 ), 6.99 (s, 2H, C 6 h 2 ), 7.05(t, 1H, J=7.6Hz, C 6 h 4 -H), 7.21(d, J=7.6Hz, 1H, C 6 h 4 6-H), 7.23(t, J=8.0Hz, 1H, C 6 h 4 5-H), 7.56(d, J=8.0Hz, 1H, C 6 h 4 3-H).

Embodiment 3

[0036] Preparation of 4-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)-5-methyl-2-(3-methylanilino)thiazole

[0037] The chemical structural formula is as follows:

[0038]

[0039] The operation is the same as in Example 1, and the reaction takes 2.0h. Product R f =0.51 (developing agent: ethyl acetate:petroleum ether=1:4), and dried to obtain 1.68g of light yellow solid, yield 96.0%, melting point 134-135°C. LC / MS: 381.2 (M+1). 1 H NMR (CDCl 3 , 400M) δ: 1.52(s, 6H, 2×CH 3 ), 2.34(s, 3H, thiazole ring 5-CH 3 ), 2.44 (s, 3H, CH 3 ), 3.03 (s, 2H, ArCH 2 ), 3.90 (s, 3H, OCH 3 ), 6.84~6.89 (m, 1H, C 6 h 4 4-H), 7.01(s, 2H, C 6 h 2 ), 7.09~7.24 (m, 3H, C 6 h 4 2-H, 5-H, C 6 h 4 6-H).

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Abstract

The invention discloses a 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity, which is shown in a formula (I) and a preparation method. The chemical structural formula of a compound shown in the formula (I) has the characteristics as follows: R is selected from H, C1-C2 alkyl groups, and C3-C4 linear alkyl groups or branched alkyl groups; Ar is selected from a phenyl group, a substituted phenyl group and a pyridyl group; and R1 is selected from the H, the C1-C2 alkyl groups, and the C3-C4 linear alkyl groups or branched alkyl groups. The preparation method of the 5-(2-aminothiazole-4-yl) benzofuranol or phenolic ether comprises the following steps of: heating 2-halogen-1-(7-hydroxyl / alkoxyl-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl) azululanone and aryl thiourea with acetone, and stirring and reacting the mixture to obtain a salt of the 5-(2-aminothiazole-4-yl) benzofuranol or phenolic ether; and neutralizing the salt of the 5-(2-aminothiazole-4-yl) benzofuranol or phenolic ether with stronger ammonia water so as to obtain the 5-(2-aminothiazole-4-yl) benzofuranol or phenolic ether. The 5-(2-aminothiazole-4-yl) benzofuranol etheric compound disclosed by the invention has good herbicidal activity and can be used as a herbicide for preventing and removing gramineae grassy weeds.

Description

technical field [0001] The invention relates to 5-(2-arylaminothiazol-4-yl)furan phenol ether compounds with herbicidal activity and a preparation method. Background technique [0002] At present, the commercialized derivatives of furanol, such as carbofuran, carbosulfan, carbosulfan, furanfur, and other large-tonnage carbamate pesticides have the disadvantage of high toxicity and will be gradually eliminated. Therefore, it is necessary to develop New low-toxic and high-efficiency broad-spectrum pesticide varieties to meet the needs of modern pesticides. [0003] Shao Ling et al. [Chemical Journal of Chinese Universities, 2007, 28(2): 270] described the introduction of 1-H-1,2,4-triazole rings to thiazole rings through the principle of active stacking and molecular splicing, and designed and A series of novel 4-aryl-5-triazolylthiazole-2-imines were synthesized. The results of biological activity tests showed that some compounds had certain antibacterial activity against P...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/78A01P13/00
Inventor 欧晓明胡艾希罗先福王宇叶姣裴晖雷满香何莲易正华白建军
Owner HUNAN CHEM RES INST
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