Synthesis and Biological Activity of 3-Alkylphosphonate Substituted Isoindolinone Derivatives†

doi:10.7503/cjcu20180215

Abstract

Abstract:

A simple and convenient one-pot synthesis of 3-alkylphosphonate substituted isoindolinone derivatives via the reaction of o-lithiated aromatic imines with carbon monoxide under one atmospheric pressure followed with bromoalkyl phosphonate was developed. These newly synthesized 3-alkylphosphonate isoindolinones were characterized by ¹H NMR, ¹³C NMR and ³¹P NMR as well as HRMS. Preliminary in vitro tests for fungicidal activity of these isoindolinone derivatives indicated that most of them exhibit good fungicidal activity.

Key words: Isoindolinone, Phosphate, Aromatic imine, Fungicidal activity

CLC Number:

O626.1

TrendMD:

LIU Xiaoyu, XU Yi, TANG Liangfu. Synthesis and Biological Activity of 3-Alkylphosphonate Substituted Isoindolinone Derivatives^†[J]. Chem. J. Chinese Universities, 2018, 39(11): 2433.

Figures/Tables 4

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Compd.	Yield(%)	HRMS, m/z[M+H]⁺(calcd.)	Compd.	Yield(%)	HRMS, m/z[M+H]⁺(calcd.)
1	62	326.1518(326.1521)	7	90	368.1992(368.1991)
2	48	340.1667(340.1678)	8	74	394.2141(394.2147)
3	65	354.1831(354.1834)	9	85	416.1986(416.1991)
4	39	380.1982(380.1991)	10	65	352.1669(352.1678)
5	95	340.1671(340.1678)	11	36	366.1831(366.1834)
6	94	354.1831(354.1834)	12	57	380.1991(380.1991)

Compd.	Yield(%)	HRMS, m/z[M+H]⁺(calcd.)	Compd.	Yield(%)	HRMS, m/z[M+H]⁺(calcd.)
1	62	326.1518(326.1521)	7	90	368.1992(368.1991)
2	48	340.1667(340.1678)	8	74	394.2141(394.2147)
3	65	354.1831(354.1834)	9	85	416.1986(416.1991)
4	39	380.1982(380.1991)	10	65	352.1669(352.1678)
5	95	340.1671(340.1678)	11	36	366.1831(366.1834)
6	94	354.1831(354.1834)	12	57	380.1991(380.1991)

Compd.	¹H NMR(400 MHz), δ	¹³C NMR(101 MHz), δ	³¹P NMR (162 MHz), δ
1	0.96—1.08(m, 1H), 1.24—1.31(m, 9H), 1.33—1.39(m, 1H), 2.30—2.37(m, 2H), 3.16—3.25(m, 1H), 3.99—4.08(m, 5H), 4.75—4.77(m, 1H), 7.42(d, J=7.5 Hz, 1H), 7.47(t, J=7.4 Hz, 1H), 7.56(dt, J=7.4, 0.9 Hz, 1H), 7.84(d, J=7.5 Hz, 1H)	13.6, 16.4, 16.5, 18.1(d, J=144.2 Hz), 23.1(d, J=3.0 Hz), 34.6, 58.0(d, J=18.9 Hz), 61.7(d, J=6.5 Hz, 2C), 121.9, 123.7, 128.5, 131.7, 133.0, 143.5, 168.3	31.5
2	0.87—1.00(m, 1H), 1.20—1.30(m, 7H), 1.37(d, J=6.9 Hz, 3H), 1.40(d, J=7.0 Hz, 3H), 2.26—2.39(m, 2H), 3.92—4.01(m, 4H), 4.24—4.35(m, 1H), 4.75—4.77(m, 1H), 7.33(d, J=7.5 Hz, 1H), 7.40(t, J=7.4 Hz, 1H), 7.49(dt, J=7.5, 1.1 Hz, 1H), 7.75(d, J=7.5 Hz, 1H)	16.3, 16.4, 18.1(d, J=144.1 Hz), 20.2, 21.2, 25.1(d, J=2.6 Hz), 44.8, 58.5(d, J=19.3 Hz), 61.5(d, J=6.0 Hz), 61.6(d, J=6.0 Hz), 121.6, 123.5, 128.4, 131.6, 133.2, 143.4, 168.7	31.6
Compd.	¹H NMR(400 MHz), δ	¹³C NMR(101 MHz), δ	³¹P NMR (162 MHz), δ
3	0.83—0.94(m, 1H), 1.24—1.30(m, 6H), 1.42—1.53(m, 1H), 1.61(s, 9H), 2.25—2.32(m, 1H), 2.40—2.49(m, 1H), 3.96—4.05(m, 4H), 4.95—4.97(m, 1H), 7.34(d, J=7.5 Hz, 1H), 7.43(t, J=7.3 Hz, 1H), 7.52(dt, J=7.4, 1.1 Hz, 1H), 7.76(d, J=7.5 Hz, 1H)	16.3, 16.4, 17.9(d, J=144.0 Hz), 25.7(d, J=2.3 Hz), 28.6, 55.3, 59.2(d, J=19.0 Hz), 61.5(d, J=6.3 Hz), 61.6(d, J=6.3 Hz), 121.3, 123.2, 128.2, 131.5, 133.8, 144.1, 169.5	31.8
4	0.91—0.99(m, 1H), 1.23—1.29(m, 6H), 1.36—1.46(m, 2H), 1.69—1.93(m, 8H), 2.26—2.44(m, 3H), 3.93—4.04(m, 5H), 4.80—4.82(m, 1H), 7.35(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.52(dt, J=7.4, 1.0 Hz, 1H), 7.79(d, J=7.5 Hz, 1H)	16.37, 16.43, 18.0(d, J=144.0 Hz), 25.2(d, J=2.6 Hz), 25.5, 26.0, 26.2, 30.8, 31.5, 53.1, 58.5(d, J=19.2 Hz), 61.5(d, J=6.6 Hz), 61.6(d, J=7.0 Hz), 121.6, 123.6, 128.4, 131.6, 133.2, 143.9, 168.8	31.7
5	1.06—1.16(m, 1H), 1.23—1.29(m, 9H), 1.32—1.39(m, 1H), 1.60—1.69(m, 2H), 2.10—2.19(m, 2H), 3.17—3.25(m, 1H), 3.97—4.08(m, 5H), 4.65—4.67(m, 1H), 7.43(d, J=7.3 Hz, 1H), 7.46(t, J=7.4 Hz, 1H), 7.54(t, J=7.4 Hz, 1H), 7.83(d, J=7.5 Hz, 1H)	13.7, 15.6(d, J=5.1 Hz), 16.4(d, J=1.2 Hz), 16.5(d, J=1.4 Hz), 25.3(d, J=141.5 Hz), 30.9(d, J=13.5 Hz), 34.6, 58.3, 61.46(d, J=0.8 Hz), 61.53(d, J=0.8 Hz), 122.0, 123.6, 128.2, 131.3, 132.9, 144.5, 168.2	31.0
6	1.03—1.12(m, 1H), 1.22—1.28(m, 6H), 1.41(d, J=6.8 Hz, 3H), 1.46(d, J=7.0 Hz, 3H), 1.59—1.58(m, 2H), 2.09—2.24(m, 3H), 3.98—4.05(m, 4H), 4.28—4.35(m, 1H), 4.67—4.76(m, 1H), 7.39(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.52(t, J=7.3 Hz, 1H), 7.80(d, J=7.4 Hz, 1H)	15.4(d, J=4.9 Hz), 16.37(d, J=5.9 Hz), 16.42(d, J=5.5 Hz), 20.3, 21.2, 25.4(d, J=141.4 Hz), 32.8(d, J=13.8 Hz), 44.8, 59.0, 61.4(d, J=5.9 Hz), 61.5(d, J=5.4 Hz), 121.7, 123.4, 128.1, 131.3, 133.1, 144.7, 168.6	31.0
7	0.92—1.03(m, 1H), 1.20—1.27(m, 6H), 1.43—1.63(m, 12H), 2.13—2.18(m, 2H), 3.96—4.03(m, 4H), 4.80—4.83(m, 1H), 7.34(d, J=7.4 Hz, 1H), 7.40(t, J=7.2 Hz, 1H), 7.48(dt, J=7.4, 1.0 Hz, 1H), 7.74(d, J=7.5 Hz, 1H)	15.5(d, J=4.9 Hz), 16.37, 16.43, 25.3(d, J=141.6 Hz), 28.6, 35.6(d, J=12.7 Hz), 55.2, 59.7, 61.4(d, J=6.9 Hz), 61.5(d, J=6.8 Hz), 121.4, 123.1, 127.9, 131.2, 133.7, 145.2, 169.4	31.1
8	0.99—1.07(m, 1H), 1.21—1.28(m, 6H), 1.38—1.45(m, 2H), 1.70—1.98(m, 10H), 2.11—2.21(m, 3H), 3.97—4.04(m, 5H), 4.68—4.73(m, 1H), 7.37(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.51(dt, J=7.4, 1.1 Hz, 1H), 7.80(d, J=7.5 Hz, 1H)	15.4(d, J=5.1 Hz), 16.39, 16.44, 25.5(d, J=141.6 Hz), 25.6, 26.1, 26.2, 30.7, 31.5, 33.0(d, J=13.9 Hz), 53.2, 59.0, 61.4(d, J=5.9 Hz), 61.5(d, J=6.3 Hz), 121.7, 123.5, 128.1, 131.3, 133.1, 144.8, 168.7	31.0
9	0.81—0.91(m, 1H), 1.24—1.27(m, 6H), 1.62—1.87(m, 5H), 2.13(s, 3H), 2.27(s, 3H), 3.99—4.02(m, 4H), 4.80—4.83(m, 1H), 7.12—7.22(m, 3H), 7.50—7.55(m, 2H), 7.58—7.62(m, 1H), 7.94(d, J=7.3 Hz, 1H)	16.4, 16.5, 18.4, 18.8, 19.4(d, J=4.7 Hz), 25.7(d, J=141.7 Hz), 34.0(d, J=15.9 Hz), 53.5, 61.5(d, J=6.2 Hz), 61.9, 122.7, 124.4, 128.3, 128.4, 128.7, 129.0, 131.7, 131.8, 134.7, 136.1, 138.0, 145.9, 167.0	30.8
10	1.23—1.30(m, 9H), 2.38—2.47(m, 2H), 2.60—2.68(m, 1H), 2.78—2.83(m, 1H), 3.20—3.27(m, 1H), 3.98—4.06(m, 5H), 4.57—4.68(m, 1H), 5.15—5.25(m, 1H), 5.43—5.52(m, 1H), 7.43—7.48(m, 2H), 7.51—7.55(m, 1H), 7.82(d, J=7.4 Hz, 1H)	13.6, 16.4, 16.5, 30.4(d, J=139.5 Hz), 34.1, 34.7, 58.1, 61.8, 61.9, 122.4, 123.4, 123.6(d, J=11.1 Hz), 128.1(d, J=14.4 Hz), 128.2, 131.2, 132.7, 144.6, 168.1	27.0
11	1.25(t, J= 5.5 Hz, 3H), 1.28(t, J=5.5 Hz, 3H), 1.43(t, J=6.8 Hz, 3H), 1.48(t, J=6.9 Hz, 3H), 2.40(t, J=7.2 Hz, 1H), 2.46(t, J=7.1 Hz, 1H), 2.66—2.70(m, 1H), 2.85—2.88(m, 1H), 3.95—4.06(m, 4H), 4.23—4.30(m, 1H), 4.64—4.66(m, 1H), 5.20—5.29(m, 1H), 5.41—5.50(m, 1H), 7.39—7.45(m, 2H), 7.49—7.53(m, 1H), 7.78(d, J=7.4 Hz, 1H)	16.3, 16.4, 20.3, 21.2, 30.3(d, J=139.7 Hz), 35.7, 45.0, 59.1(d, J=3.5 Hz), 61.67(d, J=6.7 Hz), 61.74(d, J=6.7 Hz), 122.3, 123.1, 123.5(d, J=11.1 Hz), 128.0, 128.2(d, J=14.6 Hz), 131.1, 132.9, 144.7, 168.5	27.0
12	1.11(t, J=5.4 Hz, 3H), 1.14(t, J=5.4 Hz, 3H), 1.46(s, 9H), 2.18—2.34(m, 2H), 2.48—2.55(m, 1H), 2.71—2.76(m, 1H), 3.81—3.93(m, 4H), 4.63—4.65(m, 1H), 5.00—5.09(m, 1H), 5.20—5.29(m, 1H), 7.23(d, J=7.4 Hz, 1H), 7.26(d, J=7.4 Hz, 1H), 7.33(t, J=7.4 Hz, 1H), 7.59(d, J=7.4 Hz, 1H)	16.4, 16.5, 28.7, 30.4(d, J=139.6 Hz), 38.6, 55.1, 59.7(d, J=3.5 Hz), 61.75(d, J=6.3 Hz), 61.82(d, J=6.3 Hz), 121.9, 123.0, 123.6(d, J=11.1 Hz), 127.9, 128.2(d, J=14.5 Hz), 131.0, 133.6, 145.2, 169.3	27.1

Compd.	¹H NMR(400 MHz), δ	¹³C NMR(101 MHz), δ	³¹P NMR (162 MHz), δ
1	0.96—1.08(m, 1H), 1.24—1.31(m, 9H), 1.33—1.39(m, 1H), 2.30—2.37(m, 2H), 3.16—3.25(m, 1H), 3.99—4.08(m, 5H), 4.75—4.77(m, 1H), 7.42(d, J=7.5 Hz, 1H), 7.47(t, J=7.4 Hz, 1H), 7.56(dt, J=7.4, 0.9 Hz, 1H), 7.84(d, J=7.5 Hz, 1H)	13.6, 16.4, 16.5, 18.1(d, J=144.2 Hz), 23.1(d, J=3.0 Hz), 34.6, 58.0(d, J=18.9 Hz), 61.7(d, J=6.5 Hz, 2C), 121.9, 123.7, 128.5, 131.7, 133.0, 143.5, 168.3	31.5
2	0.87—1.00(m, 1H), 1.20—1.30(m, 7H), 1.37(d, J=6.9 Hz, 3H), 1.40(d, J=7.0 Hz, 3H), 2.26—2.39(m, 2H), 3.92—4.01(m, 4H), 4.24—4.35(m, 1H), 4.75—4.77(m, 1H), 7.33(d, J=7.5 Hz, 1H), 7.40(t, J=7.4 Hz, 1H), 7.49(dt, J=7.5, 1.1 Hz, 1H), 7.75(d, J=7.5 Hz, 1H)	16.3, 16.4, 18.1(d, J=144.1 Hz), 20.2, 21.2, 25.1(d, J=2.6 Hz), 44.8, 58.5(d, J=19.3 Hz), 61.5(d, J=6.0 Hz), 61.6(d, J=6.0 Hz), 121.6, 123.5, 128.4, 131.6, 133.2, 143.4, 168.7	31.6
Compd.	¹H NMR(400 MHz), δ	¹³C NMR(101 MHz), δ	³¹P NMR (162 MHz), δ
3	0.83—0.94(m, 1H), 1.24—1.30(m, 6H), 1.42—1.53(m, 1H), 1.61(s, 9H), 2.25—2.32(m, 1H), 2.40—2.49(m, 1H), 3.96—4.05(m, 4H), 4.95—4.97(m, 1H), 7.34(d, J=7.5 Hz, 1H), 7.43(t, J=7.3 Hz, 1H), 7.52(dt, J=7.4, 1.1 Hz, 1H), 7.76(d, J=7.5 Hz, 1H)	16.3, 16.4, 17.9(d, J=144.0 Hz), 25.7(d, J=2.3 Hz), 28.6, 55.3, 59.2(d, J=19.0 Hz), 61.5(d, J=6.3 Hz), 61.6(d, J=6.3 Hz), 121.3, 123.2, 128.2, 131.5, 133.8, 144.1, 169.5	31.8
4	0.91—0.99(m, 1H), 1.23—1.29(m, 6H), 1.36—1.46(m, 2H), 1.69—1.93(m, 8H), 2.26—2.44(m, 3H), 3.93—4.04(m, 5H), 4.80—4.82(m, 1H), 7.35(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.52(dt, J=7.4, 1.0 Hz, 1H), 7.79(d, J=7.5 Hz, 1H)	16.37, 16.43, 18.0(d, J=144.0 Hz), 25.2(d, J=2.6 Hz), 25.5, 26.0, 26.2, 30.8, 31.5, 53.1, 58.5(d, J=19.2 Hz), 61.5(d, J=6.6 Hz), 61.6(d, J=7.0 Hz), 121.6, 123.6, 128.4, 131.6, 133.2, 143.9, 168.8	31.7
5	1.06—1.16(m, 1H), 1.23—1.29(m, 9H), 1.32—1.39(m, 1H), 1.60—1.69(m, 2H), 2.10—2.19(m, 2H), 3.17—3.25(m, 1H), 3.97—4.08(m, 5H), 4.65—4.67(m, 1H), 7.43(d, J=7.3 Hz, 1H), 7.46(t, J=7.4 Hz, 1H), 7.54(t, J=7.4 Hz, 1H), 7.83(d, J=7.5 Hz, 1H)	13.7, 15.6(d, J=5.1 Hz), 16.4(d, J=1.2 Hz), 16.5(d, J=1.4 Hz), 25.3(d, J=141.5 Hz), 30.9(d, J=13.5 Hz), 34.6, 58.3, 61.46(d, J=0.8 Hz), 61.53(d, J=0.8 Hz), 122.0, 123.6, 128.2, 131.3, 132.9, 144.5, 168.2	31.0
6	1.03—1.12(m, 1H), 1.22—1.28(m, 6H), 1.41(d, J=6.8 Hz, 3H), 1.46(d, J=7.0 Hz, 3H), 1.59—1.58(m, 2H), 2.09—2.24(m, 3H), 3.98—4.05(m, 4H), 4.28—4.35(m, 1H), 4.67—4.76(m, 1H), 7.39(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.52(t, J=7.3 Hz, 1H), 7.80(d, J=7.4 Hz, 1H)	15.4(d, J=4.9 Hz), 16.37(d, J=5.9 Hz), 16.42(d, J=5.5 Hz), 20.3, 21.2, 25.4(d, J=141.4 Hz), 32.8(d, J=13.8 Hz), 44.8, 59.0, 61.4(d, J=5.9 Hz), 61.5(d, J=5.4 Hz), 121.7, 123.4, 128.1, 131.3, 133.1, 144.7, 168.6	31.0
7	0.92—1.03(m, 1H), 1.20—1.27(m, 6H), 1.43—1.63(m, 12H), 2.13—2.18(m, 2H), 3.96—4.03(m, 4H), 4.80—4.83(m, 1H), 7.34(d, J=7.4 Hz, 1H), 7.40(t, J=7.2 Hz, 1H), 7.48(dt, J=7.4, 1.0 Hz, 1H), 7.74(d, J=7.5 Hz, 1H)	15.5(d, J=4.9 Hz), 16.37, 16.43, 25.3(d, J=141.6 Hz), 28.6, 35.6(d, J=12.7 Hz), 55.2, 59.7, 61.4(d, J=6.9 Hz), 61.5(d, J=6.8 Hz), 121.4, 123.1, 127.9, 131.2, 133.7, 145.2, 169.4	31.1
8	0.99—1.07(m, 1H), 1.21—1.28(m, 6H), 1.38—1.45(m, 2H), 1.70—1.98(m, 10H), 2.11—2.21(m, 3H), 3.97—4.04(m, 5H), 4.68—4.73(m, 1H), 7.37(d, J=7.5 Hz, 1H), 7.43(t, J=7.4 Hz, 1H), 7.51(dt, J=7.4, 1.1 Hz, 1H), 7.80(d, J=7.5 Hz, 1H)	15.4(d, J=5.1 Hz), 16.39, 16.44, 25.5(d, J=141.6 Hz), 25.6, 26.1, 26.2, 30.7, 31.5, 33.0(d, J=13.9 Hz), 53.2, 59.0, 61.4(d, J=5.9 Hz), 61.5(d, J=6.3 Hz), 121.7, 123.5, 128.1, 131.3, 133.1, 144.8, 168.7	31.0
9	0.81—0.91(m, 1H), 1.24—1.27(m, 6H), 1.62—1.87(m, 5H), 2.13(s, 3H), 2.27(s, 3H), 3.99—4.02(m, 4H), 4.80—4.83(m, 1H), 7.12—7.22(m, 3H), 7.50—7.55(m, 2H), 7.58—7.62(m, 1H), 7.94(d, J=7.3 Hz, 1H)	16.4, 16.5, 18.4, 18.8, 19.4(d, J=4.7 Hz), 25.7(d, J=141.7 Hz), 34.0(d, J=15.9 Hz), 53.5, 61.5(d, J=6.2 Hz), 61.9, 122.7, 124.4, 128.3, 128.4, 128.7, 129.0, 131.7, 131.8, 134.7, 136.1, 138.0, 145.9, 167.0	30.8
10	1.23—1.30(m, 9H), 2.38—2.47(m, 2H), 2.60—2.68(m, 1H), 2.78—2.83(m, 1H), 3.20—3.27(m, 1H), 3.98—4.06(m, 5H), 4.57—4.68(m, 1H), 5.15—5.25(m, 1H), 5.43—5.52(m, 1H), 7.43—7.48(m, 2H), 7.51—7.55(m, 1H), 7.82(d, J=7.4 Hz, 1H)	13.6, 16.4, 16.5, 30.4(d, J=139.5 Hz), 34.1, 34.7, 58.1, 61.8, 61.9, 122.4, 123.4, 123.6(d, J=11.1 Hz), 128.1(d, J=14.4 Hz), 128.2, 131.2, 132.7, 144.6, 168.1	27.0
11	1.25(t, J= 5.5 Hz, 3H), 1.28(t, J=5.5 Hz, 3H), 1.43(t, J=6.8 Hz, 3H), 1.48(t, J=6.9 Hz, 3H), 2.40(t, J=7.2 Hz, 1H), 2.46(t, J=7.1 Hz, 1H), 2.66—2.70(m, 1H), 2.85—2.88(m, 1H), 3.95—4.06(m, 4H), 4.23—4.30(m, 1H), 4.64—4.66(m, 1H), 5.20—5.29(m, 1H), 5.41—5.50(m, 1H), 7.39—7.45(m, 2H), 7.49—7.53(m, 1H), 7.78(d, J=7.4 Hz, 1H)	16.3, 16.4, 20.3, 21.2, 30.3(d, J=139.7 Hz), 35.7, 45.0, 59.1(d, J=3.5 Hz), 61.67(d, J=6.7 Hz), 61.74(d, J=6.7 Hz), 122.3, 123.1, 123.5(d, J=11.1 Hz), 128.0, 128.2(d, J=14.6 Hz), 131.1, 132.9, 144.7, 168.5	27.0
12	1.11(t, J=5.4 Hz, 3H), 1.14(t, J=5.4 Hz, 3H), 1.46(s, 9H), 2.18—2.34(m, 2H), 2.48—2.55(m, 1H), 2.71—2.76(m, 1H), 3.81—3.93(m, 4H), 4.63—4.65(m, 1H), 5.00—5.09(m, 1H), 5.20—5.29(m, 1H), 7.23(d, J=7.4 Hz, 1H), 7.26(d, J=7.4 Hz, 1H), 7.33(t, J=7.4 Hz, 1H), 7.59(d, J=7.4 Hz, 1H)	16.4, 16.5, 28.7, 30.4(d, J=139.6 Hz), 38.6, 55.1, 59.7(d, J=3.5 Hz), 61.75(d, J=6.3 Hz), 61.82(d, J=6.3 Hz), 121.9, 123.0, 123.6(d, J=11.1 Hz), 127.9, 128.2(d, J=14.5 Hz), 131.0, 133.6, 145.2, 169.3	27.1

Compd.	PI	CA	AS	BC	GZ	PP	SS	RC	PS
1	2.4	2.3	0	0	0	13.9	44.4	21.0	15.4
2	0	0	0	0	0	15.4	33.3	16.1	18.0
3	0	2.3	0	0	0	9.2	50.0	12.4	25.6
4	2.4	4.7	0	0	0	3.1	50.0	16.1	21.8
5	33.3	60.5	50.0	29.5	36.4	26.2	55.6	19.8	11.5
6	7.1	4.7	0	4.9	0	10.8	0	19.8	16.7
7	7.1	20.9	0	0	0	10.8	44.4	17.3	24.4
8	48.8	76.7	47.9	75.4	54.6	12.3	66.7	7.4	3.9
9	13.1	37.2	0	8.2	30.9	18.5	55.6	17.3	3.9
10	26.2	51.2	27.1	34.4	40.0	15.4	0	17.3	11.5
11	28.6	39.5	8.3	26.2	27.3	3.1	55.6	9.9	9.0
12	35.7	60.5	18.8	11.5	43.6	9.2	55.6	22.2	3.9