|
|
char = E;code = 69
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = q;code = 113
char = u;code = 117
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = g;code = 103
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = .;code = 46
result sql = Enantioselectivity in fipronil aquatic toxicity and degradation.
Enantioselectivity in fipronil aquatic toxicity and degradation.char = F;code = 70
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = c;code = 99
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = s;code = 115
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = t;code = 116
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = q;code = 113
char = u;code = 117
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = e;code = 101
char = c;code = 99
char = o;code = 111
char = s;code = 115
char = y;code = 121
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = m;code = 109
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = d;code = 100
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = e;code = 101
char = .;code = 46
char = ;code = 32
char = F;code = 70
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = i;code = 105
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = y;code = 121
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = m;code = 109
char = p;code = 112
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = i;code = 105
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = v;code = 118
char = i;code = 105
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = f;code = 102
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = e;code = 101
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = c;code = 99
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char = s;code = 115
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = ;code = 32
char = t;code = 116
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char = e;code = 101
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char = r;code = 114
char = e;code = 101
char = s;code = 115
char = e;code = 101
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char = ;code = 32
char = s;code = 115
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char = d;code = 100
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char = ;code = 32
char = f;code = 102
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char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = e;code = 101
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char = a;code = 97
char = n;code = 110
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char = i;code = 105
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = v;code = 118
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = g;code = 103
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = i;code = 105
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = c;code = 99
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char = t;code = 116
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = J;code = 74
char = a;code = 97
char = p;code = 112
char = a;code = 97
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = a;code = 97
char = k;code = 107
char = a;code = 97
char = ;code = 32
char = (;code = 40
char = O;code = 79
char = r;code = 114
char = y;code = 121
char = z;code = 122
char = i;code = 105
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = p;code = 112
char = e;code = 101
char = s;code = 115
char = );code = 41
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = h;code = 104
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = b;code = 98
char = o;code = 111
char = w;code = 119
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = (;code = 40
char = O;code = 79
char = n;code = 110
char = c;code = 99
char = o;code = 111
char = r;code = 114
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char = y;code = 121
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char = h;code = 104
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = m;code = 109
char = y;code = 121
char = k;code = 107
char = i;code = 105
char = s;code = 115
char = s;code = 115
char = );code = 41
char = .;code = 46
char = ;code = 32
char = E;code = 69
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
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char = i;code = 105
char = t;code = 116
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char = w;code = 119
char = a;code = 97
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char = ;code = 32
char = f;code = 102
char = u;code = 117
char = r;code = 114
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = e;code = 101
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char = a;code = 97
char = l;code = 108
char = u;code = 117
char = a;code = 97
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char = e;code = 101
char = d;code = 100
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char = i;code = 105
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char = e;code = 101
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char = m;code = 109
char = s;code = 115
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char = f;code = 102
char = ;code = 32
char = f;code = 102
char = i;code = 105
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char = i;code = 105
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char = e;code = 101
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char = u;code = 117
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char = d;code = 100
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = e;code = 101
char = r;code = 114
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char = c;code = 99
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char = a;code = 97
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char = c;code = 99
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char = e;code = 101
char = d;code = 100
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char = r;code = 114
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char = o;code = 111
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char = f;code = 102
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char = f;code = 102
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char = r;code = 114
char = b;code = 98
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = t;code = 116
char = e;code = 101
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char = e;code = 101
char = d;code = 100
char = s;code = 115
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char = ;code = 32
char = T;code = 84
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char = e;code = 101
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char = a;code = 97
char = l;code = 108
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char = c;code = 99
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char = n;code = 110
char = c;code = 99
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char = a;code = 97
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char = i;code = 105
char = o;code = 111
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char = t;code = 116
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char = J;code = 74
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char = p;code = 112
char = a;code = 97
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char = m;code = 109
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char = c;code = 99
char = r;code = 114
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char = /;code = 47
char = L;code = 76
char = ;code = 32
char = f;code = 102
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char = r;code = 114
char = ;code = 32
char = t;code = 116
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char = e;code = 101
char = m;code = 109
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char = c;code = 99
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char = R;code = 82
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char = -;code = 45
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char = -;code = 45
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = S;code = 83
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char = (;code = 40
char = +;code = 43
char = );code = 41
char = -;code = 45
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
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char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ,;code = 44
char = ;code = 32
char = r;code = 114
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char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = g;code = 103
char = g;code = 103
char = e;code = 101
char = s;code = 115
char = t;code = 116
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char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = s;code = 115
char = e;code = 101
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char = c;code = 99
char = e;code = 101
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
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char = 2;code = 50
char = 4;code = 52
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char = m;code = 109
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char = d;code = 100
char = i;code = 105
char = a;code = 97
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char = e;code = 101
char = f;code = 102
char = f;code = 102
char = e;code = 101
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char = t;code = 116
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = c;code = 99
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char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = b;code = 98
char = o;code = 111
char = w;code = 119
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = t;code = 116
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char = h;code = 104
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = 2;code = 50
char = 6;code = 54
char = .;code = 46
char = 7;code = 55
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = 5;code = 53
char = %;code = 37
char = ;code = 32
char = C;code = 67
char = I;code = 73
char = ,;code = 44
char = ;code = 32
char = 2;code = 50
char = 5;code = 53
char = .;code = 46
char = 6;code = 54
char = -;code = 45
char = 2;code = 50
char = 7;code = 55
char = .;code = 46
char = 9;code = 57
char = );code = 41
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = l;code = 108
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = s;code = 115
char = t;code = 116
char = ,;code = 44
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = S;code = 83
char = -;code = 45
char = (;code = 40
char = +;code = 43
char = );code = 41
char = -;code = 45
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = R;code = 82
char = -;code = 45
char = (;code = 40
char = -;code = 45
char = );code = 41
char = -;code = 45
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = e;code = 101
char = d;code = 100
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char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = 1;code = 49
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char = .;code = 46
char = 7;code = 55
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char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 7;code = 55
char = .;code = 46
char = 8;code = 56
char = %;code = 37
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
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char = v;code = 118
char = i;code = 105
char = a;code = 97
char = b;code = 98
char = i;code = 105
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = r;code = 114
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char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
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char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
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char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = e;code = 101
char = s;code = 115
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char = t;code = 116
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char = e;code = 101
char = a;code = 97
char = t;code = 116
char = m;code = 109
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char = n;code = 110
char = t;code = 116
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char = c;code = 99
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char = e;code = 101
char = n;code = 110
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char = r;code = 114
char = a;code = 97
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char = i;code = 105
char = o;code = 111
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char = s;code = 115
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char = 1;code = 49
char = 0;code = 48
char = 0;code = 48
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char = c;code = 99
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char = g;code = 103
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char = m;code = 109
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char = );code = 41
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = o;code = 111
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char = t;code = 116
char = i;code = 105
char = a;code = 97
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char = l;code = 108
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char = i;code = 105
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char = a;code = 97
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char = g;code = 103
char = r;code = 114
char = e;code = 101
char = a;code = 97
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char = e;code = 101
char = r;code = 114
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char = t;code = 116
char = h;code = 104
char = a;code = 97
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char = i;code = 105
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char = e;code = 101
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char = a;code = 97
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char = b;code = 98
char = e;code = 101
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char = w;code = 119
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char = e;code = 101
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char = a;code = 97
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char = m;code = 109
char = e;code = 101
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char = .;code = 46
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char = U;code = 85
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char = e;code = 101
char = r;code = 114
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char = a;code = 97
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char = r;code = 114
char = o;code = 111
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char = i;code = 105
char = c;code = 99
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char = s;code = 115
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char = a;code = 97
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char = i;code = 105
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
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char = i;code = 105
char = l;code = 108
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char = i;code = 105
char = n;code = 110
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char = s;code = 115
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char = m;code = 109
char = e;code = 101
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char = s;code = 115
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char = w;code = 119
char = a;code = 97
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char = e;code = 101
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char = s;code = 115
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char = n;code = 110
char = t;code = 116
char = i;code = 105
char = a;code = 97
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char = l;code = 108
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char = e;code = 101
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char = e;code = 101
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char = t;code = 116
char = h;code = 104
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char = i;code = 105
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char = E;code = 69
char = F;code = 70
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char = F;code = 70
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char = H;code = 72
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char = v;code = 118
char = e;code = 101
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char = F;code = 70
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char = d;code = 100
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char = a;code = 97
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char = t;code = 116
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char = p;code = 112
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char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = S;code = 83
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char = (;code = 40
char = +;code = 43
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char = -;code = 45
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char = i;code = 105
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char = o;code = 111
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char = d;code = 100
char = i;code = 105
char = m;code = 109
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result sql = Fipronil and its transformation products are being increasingly detected in aquatic ecosystems as a result of widespread use. Fipronil is a chiral compound, and enantioselectivity may greatly impact its environmental fate and effects. In the present study, fipronil enantiomers were isolated and used to investigate the possibility of enantioselectivity in their acute toxicity to Japanese medaka (Oryzias latipes) and cytotoxicity to primary hepatocytes from rainbow trout (Oncorhynchus mykiss). Enantioselectivity was further evaluated in terms of fipronil degradation in sediments under aerobic and anaerobic conditions and in field-contaminated runoff water from urban watersheds. The 96-h median lethal concentrations to Japanese medaka were 94.2 (95% confidence interval [CI], 82.9-107.1), 98.3 (95% CI, 85.6-113.0), and 95.4 (95% CI, 74.7-121.9) microg/L for the racemic, R-(-)-, and S-(+)-fipronil, respectively, suggesting absence of enantioselectivity. The 24-h median effect concentration of racemic fipronil to primary rainbow trout hepatocytes was 26.7 (95% CI, 25.6-27.9) microg/ml. In contrast, exposure of the cells to the S-(+)- and R-(-)-enantiomers resulted in a 19.7 and 7.8% reduction in cell viability, respectively, at the highest treatment concentrations (100 microg/ml), potentially indicating a greater-than-additive interaction between enantiomers. Under aerobic or slightly reduced conditions, biodegradation of fipronil in sediments was essentially nonstereoselective, with the enantiomeric fraction (EF) similar to racemic (EF = 0.5) after 168 d of incubation. However, EF decreased to as low as less than 0.1 following short incubations under anaerobic conditions, suggesting preferential degradation of S-(+)-fipronil in strongly reduced sediments. A survey of urban runoff samples consistently showed near-racemic EF, indicating fipronil degradation that was not enantioselective. Results suggest that site-specific characteristics are critical in accurately predicting fipronil fate and toxicity in the environment.
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result sql = Enantioselectivity in fipronil aquatic toxicity and degradation.
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char = r;code = 114
char = ;code = 32
char = e;code = 101
char = v;code = 118
char = a;code = 97
char = l;code = 108
char = u;code = 117
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = g;code = 103
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = e;code = 101
char = r;code = 114
char = o;code = 111
char = b;code = 98
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = e;code = 101
char = r;code = 114
char = o;code = 111
char = b;code = 98
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = e;code = 101
char = l;code = 108
char = d;code = 100
char = -;code = 45
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = r;code = 114
char = u;code = 117
char = n;code = 110
char = o;code = 111
char = f;code = 102
char = f;code = 102
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = u;code = 117
char = r;code = 114
char = b;code = 98
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = h;code = 104
char = e;code = 101
char = d;code = 100
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = 9;code = 57
char = 6;code = 54
char = -;code = 45
char = h;code = 104
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = l;code = 108
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = J;code = 74
char = a;code = 97
char = p;code = 112
char = a;code = 97
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = a;code = 97
char = k;code = 107
char = a;code = 97
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = 9;code = 57
char = 4;code = 52
char = .;code = 46
char = 2;code = 50
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = 5;code = 53
char = %;code = 37
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = f;code = 102
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = v;code = 118
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = [;code = 91
char = C;code = 67
char = I;code = 73
char = ];code = 93
char = ,;code = 44
char = ;code = 32
char = 8;code = 56
char = 2;code = 50
char = .;code = 46
char = 9;code = 57
char = -;code = 45
char = 1;code = 49
char = 0;code = 48
char = 7;code = 55
char = .;code = 46
char = 1;code = 49
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = 9;code = 57
char = 8;code = 56
char = .;code = 46
char = 3;code = 51
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = 5;code = 53
char = %;code = 37
char = ;code = 32
char = C;code = 67
char = I;code = 73
char = ,;code = 44
char = ;code = 32
char = 8;code = 56
char = 5;code = 53
char = .;code = 46
char = 6;code = 54
char = -;code = 45
char = 1;code = 49
char = 1;code = 49
char = 3;code = 51
char = .;code = 46
char = 0;code = 48
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 9;code = 57
char = 5;code = 53
char = .;code = 46
char = 4;code = 52
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = 5;code = 53
char = %;code = 37
char = ;code = 32
char = C;code = 67
char = I;code = 73
char = ,;code = 44
char = ;code = 32
char = 7;code = 55
char = 4;code = 52
char = .;code = 46
char = 7;code = 55
char = -;code = 45
char = 1;code = 49
char = 2;code = 50
char = 1;code = 49
char = .;code = 46
char = 9;code = 57
char = );code = 41
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = L;code = 76
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = ,;code = 44
char = ;code = 32
char = R;code = 82
char = -;code = 45
char = (;code = 40
char = -;code = 45
char = );code = 41
char = -;code = 45
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = S;code = 83
char = -;code = 45
char = (;code = 40
char = +;code = 43
char = );code = 41
char = -;code = 45
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = g;code = 103
char = g;code = 103
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = s;code = 115
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = 2;code = 50
char = 4;code = 52
char = -;code = 45
char = h;code = 104
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = e;code = 101
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = i;code = 105
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = b;code = 98
char = o;code = 111
char = w;code = 119
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = h;code = 104
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = 2;code = 50
char = 6;code = 54
char = .;code = 46
char = 7;code = 55
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = 5;code = 53
char = %;code = 37
char = ;code = 32
char = C;code = 67
char = I;code = 73
char = ,;code = 44
char = ;code = 32
char = 2;code = 50
char = 5;code = 53
char = .;code = 46
char = 6;code = 54
char = -;code = 45
char = 2;code = 50
char = 7;code = 55
char = .;code = 46
char = 9;code = 57
char = );code = 41
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = l;code = 108
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = s;code = 115
char = t;code = 116
char = ,;code = 44
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = S;code = 83
char = -;code = 45
char = (;code = 40
char = +;code = 43
char = );code = 41
char = -;code = 45
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = R;code = 82
char = -;code = 45
char = (;code = 40
char = -;code = 45
char = );code = 41
char = -;code = 45
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = 1;code = 49
char = 9;code = 57
char = .;code = 46
char = 7;code = 55
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 7;code = 55
char = .;code = 46
char = 8;code = 56
char = %;code = 37
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = v;code = 118
char = i;code = 105
char = a;code = 97
char = b;code = 98
char = i;code = 105
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = 0;code = 48
char = 0;code = 48
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = l;code = 108
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = t;code = 116
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = -;code = 45
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = n;code = 110
char = -;code = 45
char = a;code = 97
char = d;code = 100
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = w;code = 119
char = e;code = 101
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = U;code = 85
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = e;code = 101
char = r;code = 114
char = o;code = 111
char = b;code = 98
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = s;code = 115
char = l;code = 108
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = t;code = 116
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = g;code = 103
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
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result sql = Fipronil and its transformation products are being increasingly detected in aquatic ecosystems as a result of widespread use. Fipronil is a chiral compound, and enantioselectivity may greatly impact its environmental fate and effects. In the present study, fipronil enantiomers were isolated and used to investigate the possibility of enantioselectivity in their acute toxicity to Japanese medaka (Oryzias latipes) and cytotoxicity to primary hepatocytes from rainbow trout (Oncorhynchus mykiss). Enantioselectivity was further evaluated in terms of fipronil degradation in sediments under aerobic and anaerobic conditions and in field-contaminated runoff water from urban watersheds. The 96-h median lethal concentrations to Japanese medaka were 94.2 (95% confidence interval [CI], 82.9-107.1), 98.3 (95% CI, 85.6-113.0), and 95.4 (95% CI, 74.7-121.9) microg/L for the racemic, R-(-)-, and S-(+)-fipronil, respectively, suggesting absence of enantioselectivity. The 24-h median effect concentration of racemic fipronil to primary rainbow trout hepatocytes was 26.7 (95% CI, 25.6-27.9) microg/ml. In contrast, exposure of the cells to the S-(+)- and R-(-)-enantiomers resulted in a 19.7 and 7.8% reduction in cell viability, respectively, at the highest treatment concentrations (100 microg/ml), potentially indicating a greater-than-additive interaction between enantiomers. Under aerobic or slightly reduced conditions, biodegradation of fipronil in sediments was essentially nonstereoselective, with the enantiomeric fraction (EF) similar to racemic (EF = 0.5) after 168 d of incubation. However, EF decreased to as low as less than 0.1 following short incubations under anaerobic conditions, suggesting preferential degradation of S-(+)-fipronil in strongly reduced sediments. A survey of urban runoff samples consistently showed near-racemic EF, indicating fipronil degradation that was not enantioselective. Results suggest that site-specific characteristics are critical in accurately predicting fipronil fate and toxicity in the environment.
Publication: Environ. Toxicol. Chem. 2009 Sep ;28(9)::1825-33. :doi: 10.1897/08-658.1.
Publication Date: 2009 Sep
Study Author(s): Nillos, Mae G;Lin, Kunde;Gan, Jay;Bondarenko, Svetlana;Schlenk, Daniel;
Institution: Department of Environmental Sciences, University of California, Riverside, California 92521, USA.
Shortcut link to this study:
Publication Date: 2009 Sep
Study Author(s): Nillos, Mae G;Lin, Kunde;Gan, Jay;Bondarenko, Svetlana;Schlenk, Daniel;
Institution: Department of Environmental Sciences, University of California, Riverside, California 92521, USA.
Shortcut link to this study:
Fipronil and its transformation products are being increasingly detected in aquatic ecosystems as a result of widespread use. Fipronil is a chiral compound, and enantioselectivity may greatly impact its environmental fate and effects. In the present study, fipronil enantiomers were isolated and used to investigate the possibility of enantioselectivity in their acute toxicity to Japanese medaka (Oryzias latipes) and cytotoxicity to primary hepatocytes from rainbow trout (Oncorhynchus mykiss). Enantioselectivity was further evaluated in terms of fipronil degradation in sediments under aerobic and anaerobic conditions and in field-contaminated runoff water from urban watersheds. The 96-h median lethal concentrations to Japanese medaka were 94.2 (95% confidence interval [CI], 82.9-107.1), 98.3 (95% CI, 85.6-113.0), and 95.4 (95% CI, 74.7-121.9) microg/L for the racemic, R-(-)-, and S-(+)-fipronil, respectively, suggesting absence of enantioselectivity. The 24-h median effect concentration of racemic fipronil to primary rainbow trout hepatocytes was 26.7 (95% CI, 25.6-27.9) microg/ml. In contrast, exposure of the cells to the S-(+)- and R-(-)-enantiomers resulted in a 19.7 and 7.8% reduction in cell viability, respectively, at the highest treatment concentrations (100 microg/ml), potentially indicating a greater-than-additive interaction between enantiomers. Under aerobic or slightly reduced conditions, biodegradation of fipronil in sediments was essentially nonstereoselective, with the enantiomeric fraction (EF) similar to racemic (EF = 0.5) after 168 d of incubation. However, EF decreased to as low as less than 0.1 following short incubations under anaerobic conditions, suggesting preferential degradation of S-(+)-fipronil in strongly reduced sediments. A survey of urban runoff samples consistently showed near-racemic EF, indicating fipronil degradation that was not enantioselective. Results suggest that site-specific characteristics are critical in accurately predicting fipronil fate and toxicity in the environment.
PMID: 19355792
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