Synthesis and Herbicidal Activity of 2-(4-Arylxoyphenoxy)propionamide Derivatived from Benzofuranol†

doi:10.7503/cjcu20160335

Abstract

Abstract:

2-(4-Aryloxyphenoxy) propionamide derivatives were identified as one of the most important herbicides, which inhibited acetyl-CoA carboxylase(ACCase) to restrict fatty acid. Recent years, 2-(4-aryloxyphenoxy) propionamide derivative have developed resistance in varying degrees among weeds. Therefore, resear-ching novel 2-(4-aryloxyphenoxy) propionamide derivatives herbicide is of great importance. Seventeen of 2-(4-aryloxyphenoxy) propionamide derivatives were synthesized by multistep synthetic procedures with two key intermediates 2 and 9, starting from(R)-(+)2-(4-hydroxyphenoxy) propanoic acid and benzofuranol. The intermediate 9 was synthesized from o-phthalic anhydride and 2-aminoethanol via substitution reaction, bromination, etherification and amination. The synthetic reaction condition of intermediates 9 was discussed. The structures of target compounds 4 and 5 were confirmed by ¹H NMR, ¹³C NMR, HRMS and optical rotation. The bioassay results indicated that most of title compounds possessed a moderate herbicidal activity against crabgrass and barnyard grass at 1500 g/hm². The compounds 4a, 4b, 4i, 5e and 5h showed more than 96% activities against the crabgrass and barnyard grass at 375 g/hm².

Key words: 2-(4-Aryloxyphenoxy) propionamide, Benzofuranol, Herbicidal activity(Ed.: P, H, Y, K)

TrendMD:

YANG Zihui,LI Beibei,YE Jiao,HU Aixi. Synthesis and Herbicidal Activity of 2-(4-Arylxoyphenoxy)propionamide Derivatived from Benzofuranol^†[J]. Chem. J. Chinese Universities, 2016, 37(8): 1442.

Figures/Tables 6

Fig.1 Structures of compounds A—E

Scheme 1 Synthetic routes of target compounds 4 and 5

Table 1 Reaction time, appearance, yields, melting points, optical rotations and HRMS data for compounds 4 and

Compd.	t/h	Appearance	m. p./℃	Yield(%)	[α $] D 20$ /(°)(c 1,CH₂Cl₂)	HRMS(EI)(calcd.), m/z
4a	1.5	Yellow solid	146—148	71.1	+27.80	578.1424(578.1431)
4b	1.5	White solid	123—125	61.1	+39.10	592.1578(592.1588)
4c	1.5	Yellow solid	113—115	62.8	+15.00	518.1850(518.1853)
4d	1.0	White solid	125—126	78.6	+36.20	532.2005(532.2010)
4e	1.0	Yellow solid	68—70	67.9	+37.50	544.1811(544.1821)
4f	1.5	Yellow solid	130—132	73.2	+43.30	558.1965(558.1978)
4g	1.0	Yellow solid	129—131	62.8	+57.50	528.1452(528.1463)
4h	1.0	Yellow solid	66—68	70.2	+28.50	542.1600(542.1620)
4i	1.5	Yellow solid	58—60	64.7	+27.40	572.2134(572.2134)
5a	2.0	Yellow solid	49—51	59.1	+15.50	500.1502(500.1514)
5b	3.0	White solid	53—55	64.1	+27.80	516.1870(516.1872)
5c	3.0	Yellow solid	68—70	58.0	+15.05	550.1478(550.1482)
5d	2.0	Yellow solid	84—86	62.8	+20.00	533.1715(533.1717)
5e	3.0	Yellow solid	80—82	63.7	+20.30	514.1649(514.1671)
5f	3.0	Yellow solid	63—65	50.8	+20.25	530.2020(530.2029)
5g	2.0	White solid	93—95	52.4	+24.90	564.1619(564.1639)
5h	2.0	Brown solid	74—76	65.4	+15.00	547.1852(547.1874)

Table 1 Reaction time, appearance, yields, melting points, optical rotations and HRMS data for compounds 4 and

Compd.	t/h	Appearance	m. p./℃	Yield(%)	[α $] D 20$ /(°)(c 1,CH₂Cl₂)	HRMS(EI)(calcd.), m/z
4a	1.5	Yellow solid	146—148	71.1	+27.80	578.1424(578.1431)
4b	1.5	White solid	123—125	61.1	+39.10	592.1578(592.1588)
4c	1.5	Yellow solid	113—115	62.8	+15.00	518.1850(518.1853)
4d	1.0	White solid	125—126	78.6	+36.20	532.2005(532.2010)
4e	1.0	Yellow solid	68—70	67.9	+37.50	544.1811(544.1821)
4f	1.5	Yellow solid	130—132	73.2	+43.30	558.1965(558.1978)
4g	1.0	Yellow solid	129—131	62.8	+57.50	528.1452(528.1463)
4h	1.0	Yellow solid	66—68	70.2	+28.50	542.1600(542.1620)
4i	1.5	Yellow solid	58—60	64.7	+27.40	572.2134(572.2134)
5a	2.0	Yellow solid	49—51	59.1	+15.50	500.1502(500.1514)
5b	3.0	White solid	53—55	64.1	+27.80	516.1870(516.1872)
5c	3.0	Yellow solid	68—70	58.0	+15.05	550.1478(550.1482)
5d	2.0	Yellow solid	84—86	62.8	+20.00	533.1715(533.1717)
5e	3.0	Yellow solid	80—82	63.7	+20.30	514.1649(514.1671)
5f	3.0	Yellow solid	63—65	50.8	+20.25	530.2020(530.2029)
5g	2.0	White solid	93—95	52.4	+24.90	564.1619(564.1639)
5h	2.0	Brown solid	74—76	65.4	+15.00	547.1852(547.1874)

Table 2 1H NMR and 13C NMR data for compounds 4 and 5

Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
4a	1.56(s, 6H, 2×CH₃), 1.62(d, J=6.8 Hz, 3H, CH₃), 3.09(s, 2H, CH₂), 3.92(s, 3H, OCH₃), 4.63—4.69(m, 1H, CH), 4.74—4.80(m, 2H, COCH₂), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.12(d, J=8.8 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.62(t, J=4.0 Hz, 1H, NH), 7.97(s, 1H, C₅H₂N), 8.26(s, 1H, C₅H₂N)	19.0, 28.4, 42.4, 45.9, 56.1, 75.8, 89.8, 110.9, 116.7, 118.8, 119.2, 122.8, 124.2, 127.8, 128.3, 132.9, 136.5, 142.7, 144.8, 147. 1, 153.0, 154.9, 161.4, 172.3, 191.7
4b	1.46(t,J=7.0 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 4.13(q, J=7.0 Hz, 2H, OCH₂), 4.62—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH₂), 7.04(d, J=9.0 Hz, 2H, C₆H₄), 7.12(d, J=9.0 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.62(t, J=4.0 Hz, 1H, NH), 7.96(d, J=1.5 Hz, 1H, C₅H₃N), 8.25(d, J=1.5 Hz, 1H, C₅H₃N)	14.7, 19.0, 28.4, 43.0, 45.6, 64.9, 75.5, 89.8, 112.5, 114.8, 116.8, 118.7, 119.2, 122.9, 127.3, 127.7, 128.8, 134.0, 136.2, 142.4, 143.6, 147.2, 155.0, 172.3, 164.2, 191.8
4c	1.53(s, 6H, 2×CH₃), 1.63(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 3.90(s, 3H, OCH₃), 4.68—4.69(m, 1H, CH), 4.69—4.74(m, 2H, COCH₂), 7.00(d, J=9.5 Hz, 2H, C₆H₄), 7.09(d, J=9.5 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.44(s, 1H. C₆H₂), 7.47(dd, J₁=2.5 Hz, J₂=9.0 Hz, 1H, C₆H₃), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C₆H₃)	19.0, 28.1, 42.7, 45.5, 56.1, 76.2, 90.1, 106.0, 110.8, 117.3, 117.6, 118.7, 118.9, 120.6, 120.7, 121.2, 127.7, 128.3, 129.4, 144.8, 149.0, 151.2, 153.0, 153.6, 154.6, 172.2, 191.9
4d	1.41(t, J=7.0 Hz, 3H, CH₂CH₃), 1.51(s, 6H, 2×CH₃), 1.61(d, J=6.5 Hz, 3H, CH₃), 3.04(s, 2H , CH₂), 4.72(q, J=7.0 Hz, 1H, CH₂), 4.66—4.67(m, 1H, CH), 4.68—4.73(m, 2H, COCH₂), 6.86(t, J=8.5 Hz, 1H, C₆H₃), 6.98—7.01(m, 4H, C₆H₄), 7.30(d, J=8.5 Hz, 1H, C₆H₃), 7.37(s, 1H, C₆H₂), 7.41(s, 1H, C₆H₂), 7.41—7.43(m, 1H, C₆H₃), 7.59(t, J=4.5 Hz, 1H, NH)	15.0, 18.8, 28.1, 42.4, 45.5, 64.6, 75.8, 90.5, 106.1, 112.3 117.2, 118.7 120.5, 120.7, 121.3, 127.6, 128.5, 129.4, 143.9, 149.0, 150.3, 150.4, 151.1, 153.3, 154.5, 171.9, 191.9
Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
4e	1.55(s, 6H, 2×CH₃), 1.64(d, J=6.5 Hz, 3H, CH₃), 3.08(s, 2H, CH₂), 3.91(s, 3H, OCH₃), 4.63—4.68(m, 1H, CH), 4.73—4.78(m, 2H , COCH₂), 6.98(d, J=8.5 Hz, 1H, C₅H₃N), 7.03(d, J=9.0 Hz, 2H, C₆H₄), 7.09(d, J=9.0 Hz, 2H, C₆H₄), 7.41(s, 1H, C₆H₂), 7.45(s 1H, C₆H₂), 7.60(t, J=4.0 Hz, 1H, NH), 7.87(dd, J₁=8.5 Hz, J₂=2.5 Hz, 1H, C₅H₃N), 8.42(d, J=2.5 Hz, 1H, C₅H₃N)	18.7, 28.4, 42.7, 45.5, 56.1, 75.8, 90.1, 110.9, 111.5, 116.7, 118.9, 122.7, 123.1, 127.8, 128.2, 136.7, 144.9, 145.3, 147.6, 150.8, 152.9, 154.7, 166.5, 172.4, 191.8
4f	1.46(t, J=7.0 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 4.13(q, J=7.0 Hz, 2H, OCH₂), 4.63—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH₂), 6.98—7.00(m, 1H, C₅H₃N), 6.98(d, J =8.5 Hz, 1H, C₅H₃N), 7.03(d, J=9.0 Hz, 2H, C₆H₄), 7.09(d, J=9.0 Hz, 2H, C₆H₄), 7.41(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.60(t, J=4.0 Hz, 1H, NH), 7.87—7.90(m, 1H, C₅H₃N), 8.42(d, J=3.5 Hz, 1H, C₅H₃N)	14.7, 18.8, 28.1, 42.7, 45.5, 64.6 75.8, 90.1, 111.3, 112.5, 116.9, 118.9, 121.4, 122.4, 122.6, 127.7, 128.7, 136.7, 144.0, 145.4, 147.7, 153.1, 154.7, 165.9, 172.4, 191.7
4g	1.53(s, 6H, 2×CH₃), 1.62(d, J=6.5 Hz, 3H, CHCH₃), 3.07(s, 2H, CH₂), 3.90(s, 3H, OCH₃), 4.60—4.65(m, 1H, CH), 4.71—4.77(m, 2H, COCH₂), 7.00(d, J=9.5 Hz, 2H, C₆H₄), 7.09(d, J=9.5 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.47(dd, J₁=9.0 Hz, J₂=2.5 Hz, 1H, C₅H₂N), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C₅H₂N)	18.8, 28.1, 42.4, 45.5, 56.1, 75.8, 89.8, 110.8, 116.7, 118.9, 122.5, 124.9, 125.1, 127.8, 128.2, 140.2, 144.7, 145.7, 147.4, 148.3, 152.9, 154.5, 172.3, 191.8
4h	1.44(t, J=6.8 Hz, 3H, CH₂CH₃), 1.53(s, 6H, 2×CH₃), 1.62(d, J=6.4 Hz, 3H, CH₃), 3.05(s, 2H, CH₂), 4.13(q, J=6.8 Hz, 2H, OCH₂), 4.59—4.67(m, 1H, CH), 4.71—4.77(m, 2H, COCH₂), 7.00(d, J=9.2 Hz, 2H, C₆H₄), 7.09(d, J=9.2 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.42(s, 1H, C₆H₂ 6-H), 7.47(dd, J₁=9.2 Hz, J₂=2.0 Hz, 1H, C₅H₃N), 7.61(t, J=4.0 Hz, 1H, NH), 8.42(d, J=2.0 Hz, 1H, C₅H₃N)	14.7, 19.1, 28.1, 42.7, 45.5, 64.6, 75.8, 89.9, 112.3, 116.7, 118.7, 122.4, 124.9, 125.2, 127.7, 128.5, 140.3, 144.0, 147.4, 148.4, 151.4, 153.2, 154.5, 172.3, 191.7
4i	1.41(t, J=7.5 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 1.82—1.89(m, 2H, CH₂), 3.07(s, 2H, ArCH₂), 4.04(t, J=7.0 Hz, 2H, OCH₂), 4.65—4.69(m, 1H, CH), 4.74—4.79(m, 2H, COCH₂), 6.98(d, J=6.0 Hz, 1H, C₅H₃N, 6-H), 7.04(d, J=8.5 Hz, 2H, C₆H₄), 7.10(d, J=8.5 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.45(s, 1H, C₆H₂), 7.69(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, C₅H₃N), 8.43(d, J=8.5 Hz, 1H, C₅H₃N)	10.5, 18.5, 22.2, 28.4, 42.4, 45.2, 70.8, 75.6, 89.9, 105.8, 112.6, 117.0 117.5, 118.7, 120.1, 120.6, 121.2, 127.5 128.2, 129.2, 143.7, 148.7, 150.4, 151.1, 153.3, 154.2, 171.9, 191.7
5a	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.58(d, J=6.8 Hz, 3H, CH₃), 3.02(s, 2H, CH₂), 3.66—3.72(m, 2H, NHCH₂), 4.08—4.15(m, 2H, OCH₂), 4.66(q, J=6.8 Hz, 1H, CH), 6.69—6.81(m, 3H, C₆H₃), 6.94(d, J=8.8 Hz, 2H, C₆H₄), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.50(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₂N), 7.86(d, J=2.0 Hz, 1H, C₅H₂N)	18.6, 28.3, 38.9, 43.2, 68.4, 75.8, 87.6,114.4, 116.6, 118.4, 120.6, 122.2, 124.7, 125.0, 128.7, 140.1, 143.0, 145.6, 147.3, 148.1, 151.1, 151.3, 172.2
5b	1.48(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H, CH₃), 3.02(s, 2H, CH₂), 3.68—3.72(m, 2H, NHCH₂), 4.09—4.15(m, 2H, OCH₂), 4.65—4.70(m, 1H, CH), 6.71—6.81(m, 3H, C₆H₃), 6.89—6.98(m, 3H, C₆H₄, C₅H₃N), 7.04(d, J=8.8 Hz, 2H, C₆H₄), 7.87(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₂N), 8.42(s, 1H, C₅H₂N)	18.3, 27.7, 38.0, 42.6, 67.9 ,75.2 87.0, 113.8, 116.1, 118.0, 120.0, 121.9, 124.4, 124.6, 128.2, 139.5, 142.4, 145.1, 146.7, 147.5, 147.8, 150.6, 153.8, 171.7
5c	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H), 3.03(s, 2H, CH₂), 3.65—3.72(m, 2H, NHCH₂), 4.07—4.14(m, 2H, OCH₂), 4.68(q, J=6.8 Hz, 1H, CH), 6.68—6.81(m, 3H, C₆H₃), 6.96(d, J=8.8 Hz, 2H, C₆H₄), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.97(s, 1H, C₅H₂N), 8.24(s, 1H, C₅H₂N)	18,8, 28.1, 36.2, 43.0, 55.7, 74.7, 88.3, 110.1, 116.3, 116.6, 122.5, 123.1, 124.9, 125.3, 127.2, 128.0, 139.8, 144.4, 146.6, 148.2, 148.7, 154.5, 156.0, 171.8
Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
5d	1.48(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.61(d, J=6.4 Hz, 3H, CH₃), 3.01(s, 2H, CH₂), 3.68—3.72(m, 2H, NHCH₂), 4.10—4.15(m, 2H, OCH₂), 4.67—4.73(m, 1H, CH), 6.71—6.80(m, 3H, C₆H₃), 6.98(d, J=9.2 Hz, 2H, C₆H₄), 7.15(d, J=9.2 Hz, 3H, C₆H₄), 7.59(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.04(d, J=2.0 Hz, 1H, quinoxalin-H), 8.67(s, 1H, quinoxalin-H)	19.0. 28.0, 34.2, 43.2, 61.2, 75.6, 87.7, 112.7, 114.6, 116.9, 118.7, 119.5, 120.9, 121.0, 122.0, 122.6, 127.9, 128.8, 130.2, 131.1, 140.1, 144.7, 145.7, 151.9, 157.1, 170.0
5e	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.58(d, J=6.8 Hz, 3H, CH₃), 1.93—2.02(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.48—3.53(m, 2H, NHCH₂), 3.99—4.09(m, 2H, OCH₂), 4.65(q, J=6.8 Hz, 1H, CH), 6.67—6.79(m, 3H, C₆H₃), 6.90(d, J=8.8 Hz, 2H, C₆H₄), 7.06(d, J=8.8 Hz, 2H, C₆H₄), 7.50(dd, J₁=9.2 Hz, J₂=2.4 Hz, 1H, C₅H₂N), 7.85(d, J=2.4 Hz, 1H, C₅H₂N)	13.7, 23.0, 23.7, 31.5, 38.0, 62.0, 70.4, 82.1, 108.2, 111.0, 111.8, 112.8, 115.0, 117.2, 119.6, 119.8, 123.3, 134.9, 138.1, 141.8, 142.6, 143.0, 149.1, 160.3
5f	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H, CH₃), 1.95—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂, CH₂), 3.48—3.53(m, 2H, NHCH₂), 4.00—4.10(m, 2H, OCH₂), 4.63—4.68(m, 1H, CH), 6.68—6.79(m, 3H, C₆H₃), 6.92(d, J=8.4 Hz, 2H, C₆H₄), 6.99(d, J=8.8 Hz, 1H, C₅H₃N), 7.05(d, J=8.4 Hz, 2H, C₆H₄), 7.88(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₃N), 8.42(s, 1H, C₅H₃N)	18.8, 28.2, 28.8, 35.0,43.4, 65.4, 73.1, 87.3, 113.2, 115.9, 117.8, 119.1, 120.3, 122.7, 128.5, 133.0, 136.3, 142.6, 143.5, 146.8, 147.8, 149.2, 155.3, 161.4, 172.1
5g	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(s, J=6.8 Hz, 3H, CH₃), 1.94—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.48—3.53(m, 2H, NHCH₂), 4.00—4.09(m, 2H, OCH₂), 4.65—4.69(m, 1H, CH), 6.67—6.79(m, 3H, C₆H₃), 6.93(d, J=8.8 Hz, 2H, C₆H₄), 7.06(d, J=8.8 Hz, 2H, C₆H₄), 7.97(d, J=2.0 Hz, 1H, C₅H₂N), 8.24(s, 1H, C₅H₂N)	19.0, 28.3, 29.8, 36.8, 43.4, 67.4, 75.7, 87.5, 113.6, 116.4, 118.1, 119.2, 120.4, 122.8, 128.7, 136.2, 136.3, 142.6, 142.7, 143.4, 147.0, 147.9, 154.8, 161.3, 172.2
5h	1.49(s, 3H, CH₃), 1.51(s, 3H, CH₃), 1.61(d, J=6.8 Hz, 3H, CH₃), 1.97—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.50—3.55(m, 2H, NHCH₂), 4.03—4.10(m, 2H, OCH₂), 4.66—4.71(m, 1H, CH), 6.68—6.78(m, 3H, C₆H₃), 6.95(d, J=8.8 Hz, 2H, C₆H₄), 7.17(d, J=8.8 Hz, 2H, C₆H₄), 7.59(d, J₁=8.8 Hz, J₂=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.06(s, 1H, quinoxalin-H), 8.68(s, 1H, quinoxalin-H)	19.1, 28.5, 29.2, 39.0, 43.4, 66.5, 75.9, 87.4, 113.8, 114.5, 116.5, 116.6 118.1, 120.4, 121.2, 122.6, 127.9, 128.8, 129.4, 131.2, 140.2, 143.4, 146.9, 151.0, 154.5, 158.3, 172.2

Table 2 1H NMR and 13C NMR data for compounds 4 and 5

Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
4a	1.56(s, 6H, 2×CH₃), 1.62(d, J=6.8 Hz, 3H, CH₃), 3.09(s, 2H, CH₂), 3.92(s, 3H, OCH₃), 4.63—4.69(m, 1H, CH), 4.74—4.80(m, 2H, COCH₂), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.12(d, J=8.8 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.62(t, J=4.0 Hz, 1H, NH), 7.97(s, 1H, C₅H₂N), 8.26(s, 1H, C₅H₂N)	19.0, 28.4, 42.4, 45.9, 56.1, 75.8, 89.8, 110.9, 116.7, 118.8, 119.2, 122.8, 124.2, 127.8, 128.3, 132.9, 136.5, 142.7, 144.8, 147. 1, 153.0, 154.9, 161.4, 172.3, 191.7
4b	1.46(t,J=7.0 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 4.13(q, J=7.0 Hz, 2H, OCH₂), 4.62—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH₂), 7.04(d, J=9.0 Hz, 2H, C₆H₄), 7.12(d, J=9.0 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.62(t, J=4.0 Hz, 1H, NH), 7.96(d, J=1.5 Hz, 1H, C₅H₃N), 8.25(d, J=1.5 Hz, 1H, C₅H₃N)	14.7, 19.0, 28.4, 43.0, 45.6, 64.9, 75.5, 89.8, 112.5, 114.8, 116.8, 118.7, 119.2, 122.9, 127.3, 127.7, 128.8, 134.0, 136.2, 142.4, 143.6, 147.2, 155.0, 172.3, 164.2, 191.8
4c	1.53(s, 6H, 2×CH₃), 1.63(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 3.90(s, 3H, OCH₃), 4.68—4.69(m, 1H, CH), 4.69—4.74(m, 2H, COCH₂), 7.00(d, J=9.5 Hz, 2H, C₆H₄), 7.09(d, J=9.5 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.44(s, 1H. C₆H₂), 7.47(dd, J₁=2.5 Hz, J₂=9.0 Hz, 1H, C₆H₃), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C₆H₃)	19.0, 28.1, 42.7, 45.5, 56.1, 76.2, 90.1, 106.0, 110.8, 117.3, 117.6, 118.7, 118.9, 120.6, 120.7, 121.2, 127.7, 128.3, 129.4, 144.8, 149.0, 151.2, 153.0, 153.6, 154.6, 172.2, 191.9
4d	1.41(t, J=7.0 Hz, 3H, CH₂CH₃), 1.51(s, 6H, 2×CH₃), 1.61(d, J=6.5 Hz, 3H, CH₃), 3.04(s, 2H , CH₂), 4.72(q, J=7.0 Hz, 1H, CH₂), 4.66—4.67(m, 1H, CH), 4.68—4.73(m, 2H, COCH₂), 6.86(t, J=8.5 Hz, 1H, C₆H₃), 6.98—7.01(m, 4H, C₆H₄), 7.30(d, J=8.5 Hz, 1H, C₆H₃), 7.37(s, 1H, C₆H₂), 7.41(s, 1H, C₆H₂), 7.41—7.43(m, 1H, C₆H₃), 7.59(t, J=4.5 Hz, 1H, NH)	15.0, 18.8, 28.1, 42.4, 45.5, 64.6, 75.8, 90.5, 106.1, 112.3 117.2, 118.7 120.5, 120.7, 121.3, 127.6, 128.5, 129.4, 143.9, 149.0, 150.3, 150.4, 151.1, 153.3, 154.5, 171.9, 191.9
Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
4e	1.55(s, 6H, 2×CH₃), 1.64(d, J=6.5 Hz, 3H, CH₃), 3.08(s, 2H, CH₂), 3.91(s, 3H, OCH₃), 4.63—4.68(m, 1H, CH), 4.73—4.78(m, 2H , COCH₂), 6.98(d, J=8.5 Hz, 1H, C₅H₃N), 7.03(d, J=9.0 Hz, 2H, C₆H₄), 7.09(d, J=9.0 Hz, 2H, C₆H₄), 7.41(s, 1H, C₆H₂), 7.45(s 1H, C₆H₂), 7.60(t, J=4.0 Hz, 1H, NH), 7.87(dd, J₁=8.5 Hz, J₂=2.5 Hz, 1H, C₅H₃N), 8.42(d, J=2.5 Hz, 1H, C₅H₃N)	18.7, 28.4, 42.7, 45.5, 56.1, 75.8, 90.1, 110.9, 111.5, 116.7, 118.9, 122.7, 123.1, 127.8, 128.2, 136.7, 144.9, 145.3, 147.6, 150.8, 152.9, 154.7, 166.5, 172.4, 191.8
4f	1.46(t, J=7.0 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 3.07(s, 2H, CH₂), 4.13(q, J=7.0 Hz, 2H, OCH₂), 4.63—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH₂), 6.98—7.00(m, 1H, C₅H₃N), 6.98(d, J =8.5 Hz, 1H, C₅H₃N), 7.03(d, J=9.0 Hz, 2H, C₆H₄), 7.09(d, J=9.0 Hz, 2H, C₆H₄), 7.41(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.60(t, J=4.0 Hz, 1H, NH), 7.87—7.90(m, 1H, C₅H₃N), 8.42(d, J=3.5 Hz, 1H, C₅H₃N)	14.7, 18.8, 28.1, 42.7, 45.5, 64.6 75.8, 90.1, 111.3, 112.5, 116.9, 118.9, 121.4, 122.4, 122.6, 127.7, 128.7, 136.7, 144.0, 145.4, 147.7, 153.1, 154.7, 165.9, 172.4, 191.7
4g	1.53(s, 6H, 2×CH₃), 1.62(d, J=6.5 Hz, 3H, CHCH₃), 3.07(s, 2H, CH₂), 3.90(s, 3H, OCH₃), 4.60—4.65(m, 1H, CH), 4.71—4.77(m, 2H, COCH₂), 7.00(d, J=9.5 Hz, 2H, C₆H₄), 7.09(d, J=9.5 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.44(s, 1H, C₆H₂), 7.47(dd, J₁=9.0 Hz, J₂=2.5 Hz, 1H, C₅H₂N), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C₅H₂N)	18.8, 28.1, 42.4, 45.5, 56.1, 75.8, 89.8, 110.8, 116.7, 118.9, 122.5, 124.9, 125.1, 127.8, 128.2, 140.2, 144.7, 145.7, 147.4, 148.3, 152.9, 154.5, 172.3, 191.8
4h	1.44(t, J=6.8 Hz, 3H, CH₂CH₃), 1.53(s, 6H, 2×CH₃), 1.62(d, J=6.4 Hz, 3H, CH₃), 3.05(s, 2H, CH₂), 4.13(q, J=6.8 Hz, 2H, OCH₂), 4.59—4.67(m, 1H, CH), 4.71—4.77(m, 2H, COCH₂), 7.00(d, J=9.2 Hz, 2H, C₆H₄), 7.09(d, J=9.2 Hz, 2H, C₆H₄), 7.40(s, 1H, C₆H₂), 7.42(s, 1H, C₆H₂ 6-H), 7.47(dd, J₁=9.2 Hz, J₂=2.0 Hz, 1H, C₅H₃N), 7.61(t, J=4.0 Hz, 1H, NH), 8.42(d, J=2.0 Hz, 1H, C₅H₃N)	14.7, 19.1, 28.1, 42.7, 45.5, 64.6, 75.8, 89.9, 112.3, 116.7, 118.7, 122.4, 124.9, 125.2, 127.7, 128.5, 140.3, 144.0, 147.4, 148.4, 151.4, 153.2, 154.5, 172.3, 191.7
4i	1.41(t, J=7.5 Hz, 3H, CH₂CH₃), 1.55(s, 6H, 2×CH₃), 1.65(d, J=6.5 Hz, 3H, CH₃), 1.82—1.89(m, 2H, CH₂), 3.07(s, 2H, ArCH₂), 4.04(t, J=7.0 Hz, 2H, OCH₂), 4.65—4.69(m, 1H, CH), 4.74—4.79(m, 2H, COCH₂), 6.98(d, J=6.0 Hz, 1H, C₅H₃N, 6-H), 7.04(d, J=8.5 Hz, 2H, C₆H₄), 7.10(d, J=8.5 Hz, 2H, C₆H₄), 7.42(s, 1H, C₆H₂), 7.45(s, 1H, C₆H₂), 7.69(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, C₅H₃N), 8.43(d, J=8.5 Hz, 1H, C₅H₃N)	10.5, 18.5, 22.2, 28.4, 42.4, 45.2, 70.8, 75.6, 89.9, 105.8, 112.6, 117.0 117.5, 118.7, 120.1, 120.6, 121.2, 127.5 128.2, 129.2, 143.7, 148.7, 150.4, 151.1, 153.3, 154.2, 171.9, 191.7
5a	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.58(d, J=6.8 Hz, 3H, CH₃), 3.02(s, 2H, CH₂), 3.66—3.72(m, 2H, NHCH₂), 4.08—4.15(m, 2H, OCH₂), 4.66(q, J=6.8 Hz, 1H, CH), 6.69—6.81(m, 3H, C₆H₃), 6.94(d, J=8.8 Hz, 2H, C₆H₄), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.50(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₂N), 7.86(d, J=2.0 Hz, 1H, C₅H₂N)	18.6, 28.3, 38.9, 43.2, 68.4, 75.8, 87.6,114.4, 116.6, 118.4, 120.6, 122.2, 124.7, 125.0, 128.7, 140.1, 143.0, 145.6, 147.3, 148.1, 151.1, 151.3, 172.2
5b	1.48(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H, CH₃), 3.02(s, 2H, CH₂), 3.68—3.72(m, 2H, NHCH₂), 4.09—4.15(m, 2H, OCH₂), 4.65—4.70(m, 1H, CH), 6.71—6.81(m, 3H, C₆H₃), 6.89—6.98(m, 3H, C₆H₄, C₅H₃N), 7.04(d, J=8.8 Hz, 2H, C₆H₄), 7.87(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₂N), 8.42(s, 1H, C₅H₂N)	18.3, 27.7, 38.0, 42.6, 67.9 ,75.2 87.0, 113.8, 116.1, 118.0, 120.0, 121.9, 124.4, 124.6, 128.2, 139.5, 142.4, 145.1, 146.7, 147.5, 147.8, 150.6, 153.8, 171.7
5c	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H), 3.03(s, 2H, CH₂), 3.65—3.72(m, 2H, NHCH₂), 4.07—4.14(m, 2H, OCH₂), 4.68(q, J=6.8 Hz, 1H, CH), 6.68—6.81(m, 3H, C₆H₃), 6.96(d, J=8.8 Hz, 2H, C₆H₄), 7.05(d, J=8.8 Hz, 2H, C₆H₄), 7.97(s, 1H, C₅H₂N), 8.24(s, 1H, C₅H₂N)	18,8, 28.1, 36.2, 43.0, 55.7, 74.7, 88.3, 110.1, 116.3, 116.6, 122.5, 123.1, 124.9, 125.3, 127.2, 128.0, 139.8, 144.4, 146.6, 148.2, 148.7, 154.5, 156.0, 171.8
Compd.	¹H NMR( CDCl₃), δ^*	¹³C NMR(100 MHz, CDCl₃), δ
5d	1.48(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.61(d, J=6.4 Hz, 3H, CH₃), 3.01(s, 2H, CH₂), 3.68—3.72(m, 2H, NHCH₂), 4.10—4.15(m, 2H, OCH₂), 4.67—4.73(m, 1H, CH), 6.71—6.80(m, 3H, C₆H₃), 6.98(d, J=9.2 Hz, 2H, C₆H₄), 7.15(d, J=9.2 Hz, 3H, C₆H₄), 7.59(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.04(d, J=2.0 Hz, 1H, quinoxalin-H), 8.67(s, 1H, quinoxalin-H)	19.0. 28.0, 34.2, 43.2, 61.2, 75.6, 87.7, 112.7, 114.6, 116.9, 118.7, 119.5, 120.9, 121.0, 122.0, 122.6, 127.9, 128.8, 130.2, 131.1, 140.1, 144.7, 145.7, 151.9, 157.1, 170.0
5e	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.58(d, J=6.8 Hz, 3H, CH₃), 1.93—2.02(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.48—3.53(m, 2H, NHCH₂), 3.99—4.09(m, 2H, OCH₂), 4.65(q, J=6.8 Hz, 1H, CH), 6.67—6.79(m, 3H, C₆H₃), 6.90(d, J=8.8 Hz, 2H, C₆H₄), 7.06(d, J=8.8 Hz, 2H, C₆H₄), 7.50(dd, J₁=9.2 Hz, J₂=2.4 Hz, 1H, C₅H₂N), 7.85(d, J=2.4 Hz, 1H, C₅H₂N)	13.7, 23.0, 23.7, 31.5, 38.0, 62.0, 70.4, 82.1, 108.2, 111.0, 111.8, 112.8, 115.0, 117.2, 119.6, 119.8, 123.3, 134.9, 138.1, 141.8, 142.6, 143.0, 149.1, 160.3
5f	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(d, J=6.8 Hz, 3H, CH₃), 1.95—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂, CH₂), 3.48—3.53(m, 2H, NHCH₂), 4.00—4.10(m, 2H, OCH₂), 4.63—4.68(m, 1H, CH), 6.68—6.79(m, 3H, C₆H₃), 6.92(d, J=8.4 Hz, 2H, C₆H₄), 6.99(d, J=8.8 Hz, 1H, C₅H₃N), 7.05(d, J=8.4 Hz, 2H, C₆H₄), 7.88(dd, J₁=8.8 Hz, J₂=2.0 Hz, 1H, C₅H₃N), 8.42(s, 1H, C₅H₃N)	18.8, 28.2, 28.8, 35.0,43.4, 65.4, 73.1, 87.3, 113.2, 115.9, 117.8, 119.1, 120.3, 122.7, 128.5, 133.0, 136.3, 142.6, 143.5, 146.8, 147.8, 149.2, 155.3, 161.4, 172.1
5g	1.49(s, 3H, CH₃), 1.50(s, 3H, CH₃), 1.59(s, J=6.8 Hz, 3H, CH₃), 1.94—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.48—3.53(m, 2H, NHCH₂), 4.00—4.09(m, 2H, OCH₂), 4.65—4.69(m, 1H, CH), 6.67—6.79(m, 3H, C₆H₃), 6.93(d, J=8.8 Hz, 2H, C₆H₄), 7.06(d, J=8.8 Hz, 2H, C₆H₄), 7.97(d, J=2.0 Hz, 1H, C₅H₂N), 8.24(s, 1H, C₅H₂N)	19.0, 28.3, 29.8, 36.8, 43.4, 67.4, 75.7, 87.5, 113.6, 116.4, 118.1, 119.2, 120.4, 122.8, 128.7, 136.2, 136.3, 142.6, 142.7, 143.4, 147.0, 147.9, 154.8, 161.3, 172.2
5h	1.49(s, 3H, CH₃), 1.51(s, 3H, CH₃), 1.61(d, J=6.8 Hz, 3H, CH₃), 1.97—2.04(m, 2H, CCH₂C), 3.02(s, 2H, CH₂), 3.50—3.55(m, 2H, NHCH₂), 4.03—4.10(m, 2H, OCH₂), 4.66—4.71(m, 1H, CH), 6.68—6.78(m, 3H, C₆H₃), 6.95(d, J=8.8 Hz, 2H, C₆H₄), 7.17(d, J=8.8 Hz, 2H, C₆H₄), 7.59(d, J₁=8.8 Hz, J₂=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.06(s, 1H, quinoxalin-H), 8.68(s, 1H, quinoxalin-H)	19.1, 28.5, 29.2, 39.0, 43.4, 66.5, 75.9, 87.4, 113.8, 114.5, 116.5, 116.6 118.1, 120.4, 121.2, 122.6, 127.9, 128.8, 129.4, 131.2, 140.2, 143.4, 146.9, 151.0, 154.5, 158.3, 172.2

Table 3 Herbicidal activities(%) of compounds 4 and 5(1500 g/hm2)

Compd.	Pre-emergence treatment				Postemergence treatment
Compd.	Rape	Amaranth	Barnyard grass	Crabgrass	Rape	Amaranth	Barnyard grass	Crabgrass
4a	0	10.0	100	100	20.0	64.2	100	100
4b	0	30.0	100	100	15.0	0	100	100
4c	0	30.0	0	5.0	10.0	10.0	6.9	42.1
4d	15.0	62.8	16.0	15.0	10.0	0	0	42.8
4e	15.0	0	100	100	10.0	0	100	42.1
4f	20.0	0	100	100	31.1	0	85.1	74.3
4g	15.0	0	100	100	32.2	0	100	99.3
4h	10.0	15.0	100	100	31.8	0	100	95.4
4i	10.0	5.0	100	100	5.0	20.0	100	100
5a	0	0	100	100	15.0	10.0	100	87.2
5b	10.0	0	100	99.6	5.0	10.0	100	99.4
5c	0	0	99.7	100	0	15.0	100	100
5d	5.0	0	97.9	100	0	0	100	80.8
5e	0	0	100	100	0	0	100	100
5f	15.0	0	99.3	77.0	0	10.0	92.0	65.4
5g	0	5.0	78.5	100	0	15.0	100	100
5h	0	0	100	100	0	20.0	100	100
Metamifop	0	0	100	100	0	0	100	100

Table 4 Herbicidal activities(%) of compounds 4a, 4b, 4i, 5e and 5h

Compd.	Dosage/(g·hm^-2)	Pre-emergence treatment		Postemergence treatment
Compd.	Dosage/(g·hm^-2)	Barnyard grass	Crabgrass	Barnyard grass	Crabgrass
4a	750	96.1	74.5	99.5	6.3
	375	17.1	66.4	99.0	0
4b	750	74.5	100	100	59.0
	375	72.8	38.6	99.6	36.0
4i	750	100	100	100	74.3
	375	85.6	85.1	98.0	24.3
5e	750	83.0	99.8	100	0
	375	82.3	29.0	96.0	0
5h	750	29.6	52.4	100	34.8
	375	23.7	36.4	98.7	12.4

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