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1 2002 8 1 2003 11 1 152 2003 11 2 21 53 2003 12 24 4 54 2004 3 22 55 2004 4 9 56 2004 4 15 41 2004 4 15 2004 5 12 2004 5 19 2004 5 20 5 2004 12 16 58 2 2005 1 25 2005 8 23 5962 2005 8 26 2005 9 1 109 63 2005 11 29 64 2005 12 14 39 65 2006 18 66 2006 20 153 6 2006 8 28 2 68 2006 9 158 2006 9 2006 10 6 2006 10 23 2006 10 26 165 2006 30 2006 3

2006 3 31 2006 4 1 200510 4

IUPAC2--N-(4 - -2-) 2 4.4mg/kg / 100 0.044mg/kg /ADI 5

boscalidiso IUPAC 2--N-(4 --2-) 2-chloro-N-(4 -chlorobiphenyl-2-yl)nicotinamide CAS (No.188425-85-6) 2--N-(4'-[1,1'-]-2-)-3-2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl)-3-pyridinecarboxamide C18H12Cl2N2O 343.21 1992 BASF 2005 1 151 2005 1 25 BASF 5961 6

14 C Bip- 14 C- 3-14 C Pyr- 14 C- / 1 2 Bip- 14 C- 50mg/kg Bip- 14 C- 500mg/kg Bip- 14 C-Pyr- 14 C- 500mg/kg Pyr- 14 C- Wistar 168 Bip- 14 C- 15.16.4%TAR 9.384.9%TAR Bip- 14 C- Pyr- 14 C- 2.35.21%TAR 89.6 9.4%TAR 48 Bip- 14 C- 39.339.9%TARBip- 14 C- 10.11.9%TAR Bip- 14 C- Pyr- 14 C- 15.16.4 2.32.88 3.805.21 9.384.9 90.9.4 89.692.2 39.339.9 10.11.9 - * 168 48 Bip- 14 C- 8 Bip- 14 C- 1.541.58g/gBip- 14 C- 3.4.46g/g Bip- 14 C- 30.141. Bip- 14 C- 20.22.4 Bip- 14 C- g/g 1.541.58 3.4.46 30.141. 20.22.4 * 8

168 Bip- 14 C- 0.200.23g/g 0.100.13g /gbip- 14 C- Pyr- 14 C- 1.21 3.03g /g0.662.09g /g0.300.90g/g0.20.50g/g 0.200.3 g/g 168 g /g Bip- 14 C- Pyr- 14 C- 0.200.23 1.213.03 1.481.65 0.100.13 0.300.45 0.40.90 0.06 0.922.09 0.660.83 0.060.0 0.20.36 0.410.50 0.03 0.200.3 0.28 48 0.16%TAR F01 4 F02F20S- F48S-Bip- 14 C- 9.5815.8%TAR2.954.33%TAR0.460.5%TAR 1.102.28%TAR Bip- 14 C- Pyr- 14 C- 0.94 2.93%TAR0.082.41%TAR0.050.26%TAR 0.030.26%TAR Bip- 14 C- 30.5 41.0%TAR Bip- 14 C- Pyr- 14 C- 68.3 80.4%TAR F01F06SH F20S- F48 Bip- 14 C- 19.021.8%TAR4.88.5%TAR3.96.21%TAR 2.84%TAR Bip- 14 C- Pyr- 14 C-F01 4.105.5%TARF06 3.00.59%TAR F048 0.420.63%TAR F20 F02 F05Bip- 14 C- 19.3%TAR 14.2%TAR Bip- 14 C- 4.8%TAR 3.59%TAR 48 % Bip- 14 C- Pyr- 14 C- N.D.0.06 0.040.16 0.020.0 F01 9.5815.8 1.041.52 0.942.93 F02 2.954.33 0.692.41 0.081.64 8

F20 0.460.5 0.050.10 0.060.26 F48 1.102.28 0.030.18 0.040.26 30.541.0 68.380.4 0.22.9 F01 19.021.8 4.10~5.50 4.354.84 F06 4.88.5 3.00.00 3.81.59 F20 3.96.21 N.D. N.D. F48 N.D.2.84 0.420.63 N.D. N.D. N.D. N.D. F02 19.3 4.8 N.D. F05 14.2 3.59 N.D. 8 0.010.03%TAR F02F43 F46 0.200.38%TAR0.140.26%TAR 0.030.24%TAR 0.06%TAR F1 F46 F43 23 500mg/kg / 1 1 14 28 Bip- 14 C- Wistar 48 8.6114.8TAR 6.5.TAR F01 0.2.89TARF02 4.2910.8TAR 29.438.0TAR F01 12.924.5TAR 4 Bip- 14 C- Pyr- 14 C- Nadine 1 00g ai/ha 1 8 14 2 3 18 1.51.6 mg/kg 5 9

Bip- 14 C- Pyr- 14 C- Mueller-Thurgau 1 800g ai/ha 3 45 TRR 1.182.0 mg/kg12.419.6 mg/kg 43.63.4 mg/kg 92.292.%TRR96.4 9.6%TRR 95.696.1%TRR 6 Bip- 14 C- Pyr- 14 C-1 500 g ai/ha Hild s Maxi 1 810 2 1415 5153 TRR 0.060.198 mg/kg 0.1080.903 mg/kg 1.066.2 mg/kg 0.1260.205 mg/kg 1.36.12 mg/kg 93.8 12 mg/kg 64.9 8.5%TRR8.096.%TRR 98.498.6%TRR 36.92.0%TRR 9.94.5%TRR 93.695.1%TRR Pyr- 14 C- F4 9.9%TRR 2.15%TRR 1.2%TRR 1.11%TRRBip- 14 C- F62 0.50%TRR Bip- 14 C- Pyr- 14 C- 0.993 mg/kg1.022 mg/kg 20 364 Bip- 14 C- 266 62.%TAR 364 60.0% 15.5%TAR Pyr- 14 C- 364 50.1%TAR 25.4% ERR364 1.818.4%TAR 16.1.3%TAR F49 F50 0.1 10

0.2%TAR0.1%TAR 90% 108 360 F50F49 8 Bip- 14 C- 1mg/kg 30mg/kg Pyr- 14 C- 1mg/kg 20 120 1mg/kg ERR 120 3.984.2%TAR 3.6.0%TARPyr- 14 C- F4 6.%TARBip- 14 C- 30mg/kg F08 F49F50 120 0.1 0.4%TAR 261345 F50F08 F49 910 Pyr- 14 C- 40% 4.6g/g 221 15 290nm 3mW/cm 2 15 90.6%TAR 15 0.2%TAR 135 11 4 K ads =15.53.2 K ads OC=6.210 2 1.6 10 3 12 Bip- 14 C - ph 4pH ph 9 3mg/L 50 5 25 30 11

50 5 25 30 100 101%TAR 99.499.5%TAR 13 Pyr- 14 C- ph 5 3 g/ml 2.33g/mL 221 15 8 315400nm 3mW/cm 2 15 94.4%TAR 8 94.4%TAR 1415 1 mg/l 24.6 24.8 24.926.6 120 290800 nm 609 612 W/m 2 120 0.996 mg/l 0.944 mg/l 16 Bip- 14 C - 00g ai/ha 460 g ai./2l 120 120 22.0%TAR 103 80.3TAR 120 51.2%TAR 120 26.8% TAR CO2 120 19.2% TAR 26.5%TAR F64 9.42% TAR 1 6 160285 30110 18 12

20 1.40mg/kg 10 285 2.80mg/kg 160 DF 30 1410g ai./ha 110 DF 31.39 mg/kg3.00 mg/kg4.46 mg/kg19206061 5 g (16 ) (65 ) (:53.3 kg) (:15.8 kg) (:55.6 kg) (:54.2 kg) (ppm ff ff ff ff 0.123 0.36 1.4 0.50 0.5 0.18 0.1 0.04 2. 0.9 0.64 22.8 14.59 9.8 6.2 22.9 14.66 19.9 12.4 0.91 6.1 5.55 2.5 2.28 6.4 5.82 4.2 3.82 0.02 30.3 0.61 18.5 0.3 33.1 0.66 22.6 0.45 0.84 2.15 24.3 52.2 16.9 36.3 24.5 52. 18.9 40.6 2.54 4.4 11.18 2.0 5.08 1.9 4.83 3. 9.40 0.69 4.0 2.6 0.9 0.62 3.3 2.28 5. 3.93 1.25 16.3 20.38 8.2 10.25 10.1 12.63 16.6 20.5 0.02 0.1 0.00 0.1 0.00 0.1 0.00 0.1 0.00 0.01 0.4 0.00 0.3 0.00 0.1 0.00 0.3 0.00 0.14 41.6 5.82 35.4 4.96 45.8 6.41 42.6 5.96 2.81 0.1 0.28 0.1 0.28 0.1 0.28 0.1 0.28 13

2.52 0.4 1.01 0.1 0.25 0.1 0.25 0.6 1.51 0.40 35.3 14.12 36.2 14.48 30.0 12.00 35.6 14.24 0.45 5.1 2.30 4.4 1.98 5.3 2.39 5.1 2.30 0.02 0.5 0.01 0. 0.01 4.0 0.08 0.1 0.00 0.58 0.1 0.06 0.1 0.06 0.1 0.06 0.1 0.06 0.84 0.1 0.08 0.1 0.08 0.1 0.08 0.1 0.08 4.28 0.3 1.28 0.4 1.1 0.1 0.4 0.3 1.28 3.86 5.8 22.39 4.4 16.98 1.6 6.18 3.8 14.6 155.12 102.14 121.5 133.04 ff 10 12 691 6 21 / mg/kg mg/kg mg/kg 0,320,800, 800 mg/kg 3 2000,5000 320 800 5 0,2000,5000 5000-0,128,320, 320 mg/kg 8 800,2000, 5000 128 320 5 0,2000,5000 5000-14

/ 5 5 5 mg/kg 0,2000,5000 0,2000,5000 0,128,320, 800,2000, 5000 mg/kg mg/kg 5000-5000 - 5000-5 0,2000,5000 5000 - ph 5 0,2000,5000 5000 - Wistar ICR Wistar Wistar LD50 5,000 mg/kg LD50 2,000 mg/kg LC50 6. mg/l 22 25 F49 Wistar LD50 2000 mg/kg 26 Wistar 10 0, 500, 1000, 2000 15

mg/kg 2000 mg/kg 2000 mg/kg 1000 mg/kg 2000 mg/kg 2 2829 Maximization 30 Wistar 10 0, 100, 500, 2000, 5000, 15000 ppm(0,, 34, 13, 34, 10600, 8, 40, 159, 395, 1230 mg/kg /) 90 15000 ppm 5000 ppm -GTP 2000 ppm -GTP 2000 ppm 5000 ppm -GTP 500 ppm34 mg/kg / 2000 ppm 159 mg/kg / 31 C5BL/6 10 0, 150, 1000, 4000, 8000 ppm(0, 29, 19, 88, 15200, 42, 2, 1180, 2210 mg/kg /) 90 8000 ppm 4000 ppm ALT 1000 ppm 1000 ppm 1000 ppm 150 ppm 29 mg/kg /42 mg/kg / 32 16

5 0, 250, 2500, 25000 ppm( 0,.6, 8.1, 290, 8.1, 81., 825 mg/kg /) 90 25000 ppm ALP 2500 ppm ALP 2500 ppm 250 ppm.6 mg/kg /8.1 mg/kg / 33 Wistar 10 0, 150, 1500, 15000 ppm( 0, 10.5, 103, 10500, 12., 125, 120 mg/kg /) 90 15000 ppm1050 mg/kg /120 mg/kg / 34 5 0, 200, 800, 2000, 20000 ppm( 0, 5.5, 21.8, 5.4, 5440, 5.8, 22.1, 58.3, 593 mg/kg /) 12 20000 ppm ALP ALT 2000 ppm ALP 2000 ppm 800 ppm21.8 mg/kg /22.1 mg/kg / 35 Wistar 20 0, 100, 500, 2500, 15000 ppm 0, 4.4, 21.9, 1100, 5.9, 30.0, 150 mg/kg /15000 ppm 1 24 1

2500ppm Ht MCV MCH -GTP 500ppm -GTP 2500ppm 500 ppm -GTP 100 ppm4.4 mg/kg / 5.9 mg/kg / 3655 Wistar 50 0, 100, 500, 2500, 15000 ppm 0, 4.6, 23.0, 1166.0, 29., 156 mg/kg /15000 ppm 1 24 2500ppm 2500ppm 500ppm 2500ppm 50 10 50 2 13 T4 T4 TSH TSH 500 ppm 2500 ppm 100 ppm4.6 mg/kg / 500 ppm29. mg/kg / 3 55 18

C5BL/6 50 0, 80, 400, 2000, 8000 ppm(0, 13, 65, 331, 135018, 90, 443, 1800 mg/kg /) 18 8000 ppm 2000 ppm 400 ppm 80 ppm 80 ppm 8000 ppm 10 400 ppm 400 ppm 2000 ppm 80 ppm13 mg/kg / 400 ppm90 mg/kg / 3855 Wistar 25 0, 100, 1000, 10000 ppm 2 (mg/kg /) 100 ppm 1000 ppm 10000ppm 10.1 101 1040 P 10. 10 1060 F1 12.3 124 1300 12.5 125 1300 * 10000 ppm P F1F1PF1 F11000 ppm P PF1 10000 ppm F1F2 F1 F2F2F1F2 19

1000 ppm F2F2100 ppm F2 F2100 ppm P F1 F1 1000 ppm 100 ppm 13 1000 ppm 1000 ppm 10000 ppm 100 ppmp 10.1 mg/kg / F1 12.3 mg/kg / 1000 ppmp 10 mg/kg /F1 125 mg/kg / 39 Wistar 25 619 14 0, 100, 300, 1000 mg/kg / 1000 mg/kg 300 mg/kg 1000 mg/kg / 40 25 28 22 0, 100, 300, 1000 mg/kg / 1000 mg/kg /300 mg/kg 1000 mg/kg 300 mg/kg / 100 mg/kg / 1000 mg/kg / 41 20

in vitro DNA 9 4246 in vitro S. typhimurium TA100, TA98, TA1535, TA153, E. coli WP2uvrA DNA V9 CHO 20~5500 g/ +/S9 150g/mL 20~500g/mL+/S9 3500g/mLS9 101000g/mL+S9 in vivo NMRI 5 500, 1000, 200024 2 +/S9 F49 10 4 10 F49 S. typhimurium 4~5000 g/ TA100, TA98, +/S9 TA1535, TA153 E. coli WP2uvrA +/S9 Wistar 8 14 0, 15000ppm 15000ppm P450 21

EROD PROD P450 48 Wistar 5 28 0, 15000ppm 15000ppm T3 TSH pnp-gtmuf-gthobi-gt T4 49 Wistar 10 28 0, 500, 2000, 5000ppm 5000ppm 2000ppm ERODPRODBROD T4 TSH 500ppm pnp-gtmuf-gthobi-gt 50 Wistar 16 4 0, 100, 1000, 10000ppm M 51 22

14 C Bip- 14 C- 3-14 C Pyr- 14 C- 8 20.241. 168 48 0.16% F01F02 F48 30.541.0Bip- 14 C- 68.380.4Bip- 14 C- Pyr- 14 C- F01F06F20 F48 F02 F05 F4 F62 108 261345 135 K OC 60160 ph5 / 120 22 F64 1.39 mg/kg 3.00 mg/kg4.46 mg/kg 160 285 30110 LD50 5,000 mg/kg LD50 2,000 mg/kg LC50 6. mg/l F49 LD50 2000 mg/kg 23

/ T4 T4 TSH TSH TSH 29 mg/kg / 34 mg/kg /.6 mg/kg / 13 mg/kg / 4.4 mg/kg / 21.8 mg/kg / 2 10.1 mg/kg / 1000 mg/kg / 100 mg/kg / 1000 mg/kg / in vitro DNA F49 11 24

mg/kg / 90 29 42 18 13 90 90 34 159 90 1050 120 24 4.4 5.9 24 4.6 29. P 10.1 P 10. F1 12.3 F1 12.5 1000 1000 100 1000 90.6 8.1 12 21.8 22.1 11 1 mg/kg / 19 2 65 443 13 -GTP 395 21.9 -GTP 30.0 23.0 156 P 101 P 10 F1 124 F1 125 1000 8.1 81. 5.4 58.3 4.4 mg/kg / 100 0.044 mg/kg /ADI ADI 0.044mg/kg / ADI 24 4.4mg/kg / 100 1 25

1/ F01 2--N-(4 --5---2-) F02 4 --6-[[(2--3-)]]-3- F05 [3-[[(4 --2-)]]-2-] F06 N-(4 --2-)-2- F08 N-(4 --2-) F20 2--N-(4 --?--?--2- ) F43 N-(4 --2-)-2- N 5 -(2-[()]-1-[[(5-(4-)-4-[[(2- F46-3-)]]-6--2,4--1- )]]-2-) F4 2- F48 3-[[(4 ---2-)-]]-2--1- F49 N-(4 --2-)-2- F50 2--N-(4 --2-)-?- F62 4 --2- F64 4 - -?- 26

2 ai ALP ALT BROD - O - EROD - O - ERR -GTP - HOBI-GT 4-- Ht MCH MCV MUF-GT 4-- PHI pnp-gt p -- PROD - O - T3 T4 TAR TRR TSH 2

g ai./ha () PHI (mg/kg) 2000 2 DF 05 3 14 20 0.138 0.08 0.064 0.123 0.02 0.056 2000-2002 2 DF 05 2 3 21 28 35 45 14 21 0.446 0.455 0.288 0.138 0.402 0.551 0.685 0.36 0.36 0.23 0.10 0.19 0.32 0.41 2003 2 DF 666 2 1 14 2.16 0.95 0.85 1.24 0.64 0.29 2003 2 DF 1000 1 14 21 28 0.91 2.35 0.20 0.6 0.91* 0.12* 2000 2 DF 05 3 1 14 0.00 0.036 0.00 0.02 0.01 0.01 2000 2 DF 940 3 1 3 1.09 0.561 0.656 0.84 0.50 0.52 2004 2 DF 50-1500 3 1 3 2.94 2.2 1.4 2.15 1.2 1.02 2000 2 DF 1000 3 1 3 3.61 2.53 2.19 2.54 1.88 1.16 2000 2 DF 860.1940 3 1 3 0.940 0.64 0.363 0.69 0.46 0.22 2000 2 DF 940115 3 1 3 2.13 1.06 0.53 1.25 0.3 0.35 2003 2 DF 1250-1500 3 1 3 0.039 0.043 0.038 0.02 0.02 0.02 2003 2 DF 1250-1500 3 1 3-4 0.034 0.022 0.024 0.01* 0.03* 0.01* 28

14 0.39 0.14 3 DF 1333-3333 3 21 0.3 0.15 2003 28 0.25 0.11 14 29.5 14.5 3 DF 1333-3333 3 21 22.6 13.5 2003 28 18.4 10. 2 DF 1333-1595 3 14 28 3.59 3.42 2.81 2.2 2000-2002 42 2.56 2.26 2000 2 DF 1333 3 14 28 42 2.80 1.95 1.52 2.52 1.29 0.99 2000 2 SE 408425 3 1 14 0.59 0.530 0.409 0.40 0.41 0.30 2000 2 SE 20422 3 1 14 0.569 0.403 0.459 0.45 0.32 0.34 2002 2 SE 23 2 1 14 21 0.033 0.038 0.34 0.028 0.02 0.02* 0.02* 0.02* 2002 2 SE 23 2 1 14 21.45 9.48 2.8 2.9 4.24 4.81 1.50 1.40 2004 2 WDG 22-340 2 1 14 0.85 0.83 0.51 0.58 0.53 0.44 2000 2 SE 340 3 1 3 1.32 1.31 0.83 0.84 0.80 0.61 2000 2 DF 35.6115 3 1 3.39.00 4.46 4.22 3.6 2.21 2000 2 DF 14101880 3 14 21 5.20 4.19 3.85 3.83 3.31 2.96 DFSESE <0.01 0.01 * 29

1. 2004 3 10 BASF 2004 URL: http://www.acis.go.jp/syouroku/boscalid/index.htm 2. 14C-GLP BASF 2000 3. 14C-GLP BASF 2001 4. 14C-GLP BASF 2003 5. 14C-GLP BASF 1999 6. 14C-GLP BASF 2001. 14C-GLP BASF 2001 8. 14C-GLP BASF 1999 9. - 14 C-GLP BASF 2000 10. - 14 C-GLP BASF 2000 11. 14 C-GLP BASF 2000 12. GLP 2002 13. 14 C-GLP BASF 1999 14. 14 C-GLP BASF 1999 15. 14 C-GLP BASF 2002 16. GLP 2001 1. 14 C-/GLP SLFA BASF 2001 18. BASF 2001 19. BASF 20012002 20. BASF 2001 21. GLP 2000 22. BASF 1998 23. GLP 2000 24. GLP BASF 1998 30

25. GLP BASF 199 26. F49BASF 2001 2. Wistar GLP BASF 2000 28. GLP BASF 1998 29. GLP BASF 1998 30. GLP BASF 1998 31. 3 GLP BASF 2000 32. 3 GLP BASF 2000 33. 3 GLP BASF 2000 34. Wistar 90 GLP BASF 2001 35. GLP BASF 2000 36. Wistar 24 GLP BASF 2001 3. Wistar 24 GLP BASF 2001 38. 18 GLP BASF 2001 39. GLP BASF 2001 40. GLP BASF 2000 41. GLP BASF 2000 42. GLP BASF 1998 43. V9 in vitro GLP BASF 1999 44. GLP BASF 1999 45. in vitro DNA UDSGLP BASF 2000 46. CHO in vitro HPRT GLP BASF 2000 4. F49 BASF 2000 31

48. 2 GLP BASF 1999 49. 4 GLP BASF 2001 50. 4 GLP BASF 2003 51. 4 GLP 2003 52. 21 1URLhttp://www.fsc.go. jp/iinkai/i-dai21/dai21kai-siryou1.pdf 53. 22 233 21 2-1(URLhttp://www.fsc.go.jp /iinkai/i-dai21/dai21kai-siryou2-1.pdf) 54. 4 URLhttp://www.fsc.go.jp/senmon/nouyaku/ n-dai4/index.html 55. 16 2 18 BASF 2004 56. 9 URLhttp://www.fsc.go.jp/senmon/nouyaku/ n-dai9/index.html 5. 16 5 20 55 URLhttp://www.fsc.go.jp/hyouka/hy/hy-tuuchi-bunsyo-34.pdf 58. 34 30 16 12 16 16 426 59. 200 1 BASF 200 URL: http://www.fsc.go.jp/hyoukaiken.html#02 60. BASF 2005 61. BASF 2003 62. 109 1-1URLhttp://www. fsc.go.jp/iinkai/i-dai109/dai109kai-siryou1-1.pdf 63. 22 233 11 109 1-2(URLhttp://www.fsc.go.jp/iinkai/i-dai109/dai99kai-siryou1-2.pdf 64. 34 30 1 11 29 1 499 65. 39 URLhttp://www.fsc.go.jp/senmon/nouyaku/ n-dai39/index.html 66. 153 1-1-b URL http://www.fsc.go.jp/iinkai/i-dai153/dai153kai-siryou1-1-b.pdf 6. 24 2 32

153 1-4 URL http://www.fsc.go.jp/iinkai/i-dai153/dai153kai-siryou1-4.pdf 68. 2 URL http://www.fsc.go.jp/senmon/nouyaku/kanjikai_dai1/index.html 69. 10 2000 0. 11 2001 1. 12 2002 33