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2001 4 26 2003 5 22 2004 7 12 2004 7 15 54 2004 7 21 14 2004 9 16 62

IUPAC4--2--N,N --5-p --1-2 17.07 mg/kg / 100 0.17 mg/kg /ADI

cyazofamidiso IUPAC 4--2--N,N- -5-p --1-4-chloro-2-cyano-N,N -dimethyl-5-p -tolylimidazole-1-sulfonamide CAS (No.188425-85-6) 4--2--N,N --5-(4-)-1H --1-4-chloro-2-cyano-N,N -dimethyl-5-(4-methylphenyl)-1h -imidazole-1-sulfonamide C13H13ClN4O2S 324.8 1987 2001 4 14 100 1 Qi 2003 5 2283259 2 1

14 C Bz- 14 C- 4 14 C Im- 14 C- Bz- 14 C- Im- 14 C- 0.5 mg/kg 1000 mg/kg SD Bz- 14 C- Im- 14 C- 0.5 0.25 Cmax 243354 g/g48.175.6 g/g 4.45.8 7.611.6 Tmax 0.2 g/g 10 g/g 168 Bz- 14 C- 0.5 g/g 0.2 g/g 24 (TAR) 90% 168 0.5% TAR 168 49.068.2 TAR 168 94.297.6% TAR CCBA 1 23.159.3% TARCH3SO-CCIM 0.48.3% TARCH3SO2-CCIM 0.25.8% TAR 13.5 20.8% TAR CCBA 1.141.93% TARCH3SO-CCIM 0.010.14% TARCH3SO2-CCIM 0.010.08% TAR 78.492.9% TAR CCBA CCIMCCBA 35 0.5 mg/kg / 1 1 14 Bz- 14 C- SD 1 2

168 62.872.8 TAR 20.831.6 TAR 6 Bz- 14 C- Im- 14 C- 0.5mg/kg 1000mg/kg SD 72 12.238.8 TAR 0.8 1.4 TAR 40.561.6 TAR 2.735.16 TAR 9.842.3 TAR 94.796.0 TAR CCBA 2.86.4% TAR 25.467.7 TAR CCIMCCBA CHCN 7.425.2 TAR 1.12.9 TAR 2.734.7 TAR 7 CD 6 in vitro Bz- 14 C- Bz- 14 C-CCIM 0.4 g/ml Bz- 14 C- Bz- 14 C-CCIM 52.3 g 60 30% CCIM CCIM 60 CCIM 60 CCBA CCIM 8 SD 5 Bz- 14 C- Bz- 14 C-CCIM 0.5 mg/kg CCIM CCIM CCIM CCIMCCBA 6.1% TAR24.2% TAR41.9% TAR CCIMCCBACHCN 61.7% TAR34.4% TAR4.0% TAR 97.2% TAR CCIM 2.8% TAR CCIM CCIM CCIMCCBACHCN 76.5 TAR18.2 TAR3.8% TAR CCIMCCBACHCN 67.9% TAR26.6% TAR5.6% TAR CCIM CCIM CCBA 9 3

Bz- 14 C- Im- 14 C- Bush Beefsteak 1 1 100 g ai/ha 400 g ai/ha4 1 TRR 0.08010.290 mg/kg 17.4%45.8%TRR 7187% 1329% 76.479.9%TRR CCIMCCTS 77.679.1%TRRCCIM 1.125.36TRR SO2N(CH3)2 (CCTS)(CCIH) 10 Bz- 14 C- Im- 14 C- 1 100 g ai/ha1 4 1 22 4 cm (TAR) 0.2%0.0040.005 mg/kg 0.20.3% 0.0100.014 mg/kg(0-4cm) 66.074.9%TAR 3%TAR 11 Bz- 14 C- Im- 14 C-(125127 g/ml) 40 67 4 3 7 87.1114.8 TAR 0.30.5 TAR 12 Bz- 14 C- Im- 14 C- 4

Kennebecsuperior 1 100g ai/ha 400g ai/ha1 23 3 5 1 TRR 0.00080.0019 mg/kg 0.0165 0.0217 mg/kg 2 g/kg 19.755.6% TRR 16.560.9 TRR 95.0495.19% TRR CCIM 1.76 2.26 TRR 13 Bz- 14 C- Im- 14 C- pinot noir 1 100g ai/ha 2125 5 44 0.440.50 mg/kg TRR 0.0730.077 mg/kg15.416.4% TRR 0.360.41 mg/kg81.681.7% TRR 0.0090.0015 mg/kg2.02.9% TRR 56.857.9% TRR 10%TRR CCIM 4.56.6% TRR 5-CGTCCCIM CCTSCCIM-AMCCBAHTID 5-CGTCCCIM 5.47.2% TRR17.923.6% TRR4.97.5% TRR28.4% TRR CCIM5-CGTCCCIM 10.210.9 TRR 14.318.9% TRR30.431.1% TRR2.55.6% TRR1.53.7% TRR 1.11.3% TRR CCIM 34.241.1% TRR5.58.9% TRR2.63.1% TRR 14 Bz- 14 C- Im- 14 C- 100 g ai/ha 20 59 5

59 11.914.1%TAR 1520 59 47.650.4 TAR CCIMCCIM-AMCTCA CCIM 5 (14.916.3% TAR)CCIM-AM Bz- 14 C- 26 11.0% TARIm- 14 C- 15 13.2% TAR CTCA 44 9.29.8% TAR 59 3.94.7 TAR5.98.9% TAR7.38.4% TAR 90%5 3344 CCIMCTCA 15 Bz- 14 C- Im- 14 C- 100 g ai/ha 20 360 360 2.93.4% TAR 360 8083 TAR CCIMCCIM-AMCTCA CCIM 7 2127% TAR CCIM-AM 7 10.314.1% TAR CTCA 56 18.921.3% TAR 360 0.51.0 TAR1.62.1% TAR10.812.1% TAR 90% 4.756.8 28.037.6 CCIMCTCA 16 4 Kd =4.9215.4 K OC=375615 17 4 (ph7.6) ph6.9 Kd =4.1487.0 K OC=6.5710 2 2.90 10 3 18 Bz- 14 C- Im- 14 C- 50L 1g 6

10g 3mm 203 12 250750nm 12 12 12 30 CCIMCCBA CCIM CCBA 93104 95113 90% 310345 315376 19 Bz- 14 C- Im- 14 C- ph 4pH 5pH 7pH 9 70 g/l 25 30 25 ph4ph5ph7 CCIM ph 9 CCIM CCIM-AM 30 CCIMCCIM-AM(pH9 ) 1421% TAR7483% TAR910% TAR 10.613.3 20 Bz- 14 C- Im- 14 C- 70g/L 213 12 290800nm646 W/m 2 ( 300800nm) 12 1 90 1 3.75.0 35 2433 CCIMCCTSCDTSHTID CCTS 1030 40% TAR 24 23% TAR CCIM 2060 40 45% TAR 24 225% TAR CDTSHTID 24 3.914.9% TAR11.518.3% TAR 24 Bz- 14 C- 5561% TAR Im- 14 C- 2842% TAR Im- 14 C- 21 Bz- 14 C- Im- 14 C- ph 5 70g/L 252 Bz- 14 C- 36 Im- 14 C- 7

30 290 nm 12.0W/m 2 ( 290398nm) Bz- 14 C- 28 34 35 4352 CCIMCCTS HTID 20.725.6 2.12.3 41.646.1 22 Bz- 14 C- Im- 14 C- 100 g ai/ha 90 30 cm 48 200 mm 181 ml/2 0.01 M 0.8%TAR 05 cm 86.690.3TAR 4TAR 05 cm CCIMCCIM-AM 39.8 43.2%TAR22.328.4%TAR10.812.0%TAR 23 Bz- 14 C- Im- 14 C-4 100 g ai/ha 30 cm 48 200 mm 181 ml/2 0.01 M 84.795.0 0.10.4% 05 cm 81.993.5 6TAR 05 cm CCIM CCIM-AM 45.9 72.3%11.041.3%nd8.5% 24 CCIM 1 121.8 mg/kg37 16.3 mg/kg12.7 mg/kgccim1 2%2528 8

(g ai/ha) () PHI () (mg/kg) CCIM 1998 2 188 4 1 3 7 0.23 0.20 0.07 0.15 0.10 0.04* 1998 2 188 4 1 3 7 1998 2 188 4 1 3 7 0.53 0.48 0.43 0.34 0.31 0.26 0.01 0.01 0.01 0.01* 0.01* 0.01* 1998 2 188 4 7 14 21 1998 2 282 3 14 21 28 1.27 1.13 1.19 0.82 0.78 0.65 0.01 0.01 0.01 0.01* 0.01* 0.01* 1998 2 282 3 14 21 28 6.28 6.49 5.97 3.46 3.66 3.03 0.07 0.08 0.07 0.04 0.03 0.03 2000 2 0.00293 g ai/ 141 g ai/ha 5 14 21 28 0.25 0.09 0.08 0.12* 0.05* 0.04* 2000 2 188 4 7 14 21 2001 2002 4 94106 3 117 187 239 244 2001 2 94 4 1 3 7 0.34 0.23 0.14 0.26 0.19 0.11 0.01 0.01 0.01* 0.01* 9

2001 2001 2002 2002 2 2 188 205 0.0293 g ai/ 4 1 2 4771 3 2 6471 3 1 3 7 75 97 1 3 7 1 3 7 12.3 9.26 7.64 21.8 16.3 12.7 7.73 6.04 4.33 12.9 9.74 9.18 0.14 0.15 0.18 0.50 0.46 0.40 0.07 0.06* 0.06* 0.21 0.17 0.15 aiphi 0.01 * < CCIM CCIM1.49 2 16 65 (mg/kg ff ff ff ff 0.15 16.3 2.4 8.2 1.2 10.1 1.5 16.6 2.5 0.34 24.3 8.3 16.9 5.7 24.5 8.3 18.9 6.4 3.46 5.8 20.1 4.4 15.2 1.6 5.5 3.8 13.1 0.12 29.4 3.5 10.3 1.2 21.9 2.6 29.9 3.6 0.26 4.4 1.1 2.0 0.5 1.9 0.5 3.7 1.0 6.04 4.3 26.0 2.0 12.1 1.6 9.7 4.3 26.0 9.74 18.7 182.1 10.1 98.4 17.4 169.5 21.7 211.4 243.5 134.3 197.6 264.0 1 ff 10 12 2931 10

3 3 58 36 826 714 32 * 5 8 0.2 mg/kg 8 26 6 14 752 g ai/ha 3 7 CCIMCCIM-AMCTCA SD CD-1 SD SD LD50 >5000mg/kg LD50 >2000mg/kg LC50 >5.5mg/L CCIMCCIM-AM CTCA SD LD50 324mg/kg 443 mg/kg >3000 mg/kg 2947 mg/kg 1863 mg/kg 3339 SD 10 80, 400, 2000 mg/kg 400 mg/kg 11

2000 mg/kg 40 41 42 Maximization 43 Fischer 12 0, 10, 50, 500, 5000 ppm 0, 50, 500, 5000, 20000 ppm 90 20000 ppm 5000 ppm 5000 ppm 500ppm29.51 mg/kg /33.32 mg/kg / 44 4 0, 40, 200, 1000 mg/kg / 90 1000 mg/kg / 45 6 0, 4, 200, 1000 mg/kg / 1 1000 mg/kg 1000 mg/kg / 46 47 Fischer 85 50 35 10 0, 10, 50, 500, 5000 ppm 12

0, 50, 500, 5000, 20000 ppm 24 / 20000 ppm 5000 ppm 5000 ppm 10ppm 500ppm17.07 mg/kg /20.24 mg/kg / 48 ICR 60 0, 70, 700, 7000ppm 18 7000 ppm 7000ppm984.9 mg/kg /1203.4 mg/kg / 49 2 SD 30 0, 200, 2000, 20000 ppm 2 20000 ppm PF1 20000 ppm 20000 ppmp 958.4 mg/kg /F1 936.0 mg/kg / 2000 ppmp 133.9 mg/kg /F1 138.0 mg/kg / 2000 ppmf1 94.2 mg/kg /F1 133.9 mg/kg / F2 89.2 mg/kg /F2 138.0 mg/kg / 50 SD 25 019 0, 30, 100, 1000mg/kg / 1000mg/kg / 51 13

24 428 0, 30, 100, 1000mg/kg / 1000 mg/kg / 415 1000 mg/kg / 4952 DNA 4 5356 mg/kg in vitro DNA B. subtilis H17, M45 S9 S9 S.typhimurium TA98, TA100, TA1535, TA1537, E.coli WP2uvrA/pKM101 S9 in vivo CD-1 5 0, 500, 1000, 200024 2 S9 CCIMCCIM-AMCTCA 5 5759 14

CCIM S.typhimurium TA98, S9 TA100, TA1535, TA1537, E.coli WP2uvrA CCIM-AM S.typhimurium TA98, S9 TA100, TA1535, TA1537, E.coli WP2uvrA CTCA S.typhimurium TA98, S9 TA100, TA1535, TA1537, E.coli WP2uvrA S9 15

14 C 4 14 C 0.250.5 4.411.6 168 24 CCBACH3SO-CCIMCH3SO2-CCIM CCBA CCIMCCBA 5 4.756.8 93104 K OC 3756150 CCIMCCIM-AMCTCA CCIM 1 21.8 mg/kg 3 7 16.3 mg/kg 12.7 mg/kg CCIM 12% 58 36 LD50 >5,000 mg/kg LD50 >2,000 mg/kg LC50 >5.5 mg/l CCIM CCIM-AMCTCA LD50 324 mg/kg 443 mg/kg >3000 mg/kg 2947 mg/kg 1963 mg/kg 29.51 mg/kg / 1000 mg/kg / 984.9 mg/kg / 17.07 mg/kg / 1000 mg/kg / 2 89.2 mg/kg / 16

1000 mg/kg / 1000 mg/kg / DNA CCIMCCIM-AMCTCA 6 17

18 984.9 mg/kg / 1203.4 mg/kg / 90 29.51 mg/kg / 33.32 mg/kg / 24 / 17.07 mg/kg / 20.24 mg/kg / 2 P 958.4 mg/kg / P 133.9 mg/kg / F1 936.0 mg/kg / F1 138.0 mg/kg / F1 94.2 mg/kg / F1 133.9 mg/kg / F2 89.2 mg/kg / F2 138.0 mg/kg / 1000 mg/kg / 1000 mg/kg / 90 1000 mg/kg / 1000 mg/kg / 12 1000 mg/kg / 1000 mg/kg / ADI ADI 0.17 mg/kg / ADI / 24 17.07 mg/kg / 100 18

/ CCBA CCIM CCIM-AM CCTS CDTS 5-CGTC CHCN CH3SO-CCIM CH3SO2-CCIM CTCA HTID 4-(4-chloro-2-cyanoimidazole-5-yl)benzoic acid 4-chloro-5-p-tolylimidazole-2-carbonitrile 4-chloro-5-p-tolylimidazole-2-carboxamide 6-(4-chloro-2-cyanoimidazol-5-yl)-N,N-dimethyl-m-toluenesulfonamide 2-cyano-N,N-dimethyl-5-p-tolylimidazole-4-sulfonamide 5-chloro-1--D-glucopyranosyl-4-p-tolylimidazole-2-carbonitrile 4-chloro-5-(4-hydroxymethylphenyl)imidazole-2-carbonitrile 4-chloro-5-[-(methylsulfinyl)-p-tolyl]imidazole-2-carbonitrile 4-chloro-5-[-(methylsulfonyl)-p-tolyl]imidazole-2-carbonitrile 4-chloro-5-p-tolylimidazole-2-carboxylic acid 5-hydroxy-5-p-tolyl-2,4-imidazolidinedion 19

2003 20

10 2000 11 2001 12 2002 21

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