US 2006/0069132 A1 · Azolecarboxamide herbicides

Abstract

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation and R1a, R1b, R1c, R2a, R2b, R3, R4, R5, T, U, W, Y and Z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I. Also disclosed are mixtures and compositions comprising a herbicidally effective amount of a compound of Formula Iz wherein J, R1a, R1b, R1c, R2a, R2b, R3, R4, R5, T, U, W, Y and Z are as defined in the disclosure; and an effective amount of another herbicide or herbicide safener. Also disclosed is a method for selectively controlling undesired vegetation in a crop that involves contacting the locus of a crop with an effective amount of a compound of Formula Iz and a effective amount of a safener.

A compound selected from Formula I, an N-oxide or an agriculturally suitable salt thereof,

T is CR6 or N;
U is CR7 or N;
Y is CR8 or N;
Z is CR9 or N;
R1a is H, C1-C4 alkyl, C1-C4 fluoroalkyl, C2-C4 alkenyl, C2-C4 fluoroalkenyl, C2-C4 alkynyl or C2-C4 fluoroalkynyl;
R1b is halogen, C1-C4 alkyl, C1-C4 fluoroalkyl, C2-4 alkenyl, C2-C4 fluoroalkenyl, C2-C4 alkynyl or C2-C4 fluoroalkynyl;
R1c is H;
R2a is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C4-C6 alkylcycloalkyl, C3-C6 halocycloalkyl, C4-C6 cycloalkylalkyl, C5-C6 alkylcycloalkylalkyl, —CR20(OR21)(OR22) or SiR23R24R25;
R2b is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C4-C6 alkylcycloalkyl, C3-C6 halocycloalkyl, C4-C6 cycloalkylalkyl or C5-C6 alkylcycloalkylalkyl;
R3 is H, F or C1-C2 alkyl;
or
R2a or R2b is taken together with R3 as —C(R26a)(R26b)—(Y1)s—(CH2)t—(Y2)u— or —C(R26a)(R26b)—(Y1)n—CH═CH—(Y2)n— wherein the left end of the radical is connected as R2a or R2b, and the right end of the radical is connected as R3;
R4 is H, C1-C2 alkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkoxyalkyl or C2-C6 alkylthioalkyl;
R5 is C(W1)NR10R11 C(O)OR12, COR13, C(NOR14)R15, —CN, OR16, S(O)mR17 S(O)2NR18R19, OS(O)2R27 or OP(O)R28aR28b;
R6 is H, F, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, C1-C2 alkylthio or C1-C2 fluoroalkylthio;
or
R5 and R6 are taken together as a radical selected from —C(W1)N(R11)(CH2)n— and —C(NOR14)CH2(CH2)n— wherein the right end of the radical is connected to the ring at T;
R7 is H, F, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, C1-C2 alkylthio or C1-C2 fluoroalkylthio;
R8 and R9 are independently selected from H, F, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, C1-C2 alkylthio and C1-C2 fluoroalkylthio;
R10 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C2-C4 alkoxymethyl or C2-C4 alkylthiomethyl;
R11 is H, C1-C5 alkyl, C1-C5 haloalkyl, C2-C5 alkenyl, C3-C5 haloalkenyl, C3-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C3 alkoxy, C2-C5 alkoxyalkyl, C2-C5 alkylthioalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
or
R10 and R11 are taken together as —(CH2)4—, —(CH2)5—, —CH2CH═CHCH2— or —(CH2)2O(CH2)2—, each optionally substituted with 1-2 C1-C2 alkyl;
each R12 is independently C1-C5 alkyl, C1-C5 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-C5 alkenyl, C3-C5 haloalkenyl, C3-C5 alkynyl, C3-C5 cycloalkyl or C4-C5 cycloalkylalkyl;
R13 is C1-C3 alkyl, C1-C3 haloalkyl or cyclopropyl;
R14 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
R15 is C1-C3 alkyl, C1-C3 haloalkyl or cyclopropyl;
R16 is C1-C4 alkyl, C1-C4 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 alkylthioalkyl, C2-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C5 cycloalkyl or cyclopropylmethyl;
R17 is C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C3-4 haloalkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl or cyclopropylmethyl;
each R18 is independently H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C2-C4 alkoxymethyl or C2-C4 alkylthiomethyl;
each R19 is independently H, C1-C5 alkyl, C1-C5 haloalkyl, C2-C5 alkenyl, C3-C5 haloalkenyl, C3-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-c3 alkoxy, C2-C5 alkoxyalkyl or C2-C5 alkylthioalkyl;
R20 is C1-C4 alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl;
R21 is C1-C3 alkyl;
R22 is C1-C3 alkyl;
or
R21 and R22 are taken together as —CH2CH2— or —CH2CH2CH2—, each optionally substituted with 1-2 methyl;
R23 is C1-C2 alkyl or C1-C2 haloalkyl;
R24 is C1-C2 alkyl or C1-C2 haloalkyl;
R25 is C1-C2 alkyl or C1-C2 haloalkyl;
R26a and R26b are independently H or C1-C2 alkyl;
R27 is C1-C3 alkyl, C1-C3 haloalkyl or cyclopropyl;
R28a and R28b are independently C1-C2 alkyl or C1-C2 alkoxy;
W is O or S;
W1 is O or S;
Y1 and Y2 are independently CH2, O, S, NH or NCH3;
m is 0, 1 or 2;
n is 1 or 2;
s is 0 or 1;
t is 1 or 2;
and u is 0 or 1;
provided that the sum of s, t and u is 2 or 3;
and
v is 0 or 1;
w is 0 or 1;
provided that the sum of v and w is 0 or 1;
provided that
(a) when J is J-1, R1a is CH3 and R5 is C(W1)NR10R11, C(O)OR12, COR13, OR16 or S(O)mR17, then at least one of T, U, Y and Z is N or C—F;
(b) when J is J-1, R1a is CH3, R5 is C(W1)NR10R11, C(O)OR12, COR13, OR16 or S(O)mR17 and T is N, then at least one of U, Y and Z is N or C—F;
(c) when J is J-1 and R2a is CF3, then R5 is C(W1)NR10R11 or C(NOR14)R15, or R5 and R6 are taken together as a radical selected from —C(W1)N(R11)(CH2)n— and —C(NOR14)CH2(CH2)n— wherein the right end of the radical is connected to the ring at T;
(d) when J is J-3 and R1b is CF3, then R5 is C(W1)NR10R11 or C(NOR14)R15, or R5 and R6 are taken together as a radical selected from —C(W1)N(R11)(CH2)n— and —C(NOR14)CH2(CH2)n— wherein the right end of the radical is connected to the ring at T;
(e) when J is J-1 or J-4 and R5 is OR16, then R2a is other than CH3;
(f) when J is J-3 and R5 is OR16 then R2b is other than CH3;
(g) when R5 is C(W1)NR10R11 or C(NOR14)R15, then R9 is other than alkoxy or alkylthio;
(h) when R5 is C(W)NR10R11;
then R6 is other than alkyl or alkoxy;
(i) when R5 is COR13, then R1a or R1b is selected from the radicals of the group consisting of C1-C3-alkyl, C1-C3 fluoroalkyl, C2-C3-alkenyl, C2-C3 fluoroalkenyl, C2-C3 alkynyl or C2-C3 fluoroalkynyl, each radical unbranched and connected through a terminal end carbon atom to the azole ring;
(j) when R5 and R6 are taken together as —C(W1)N(R11)(CH2)n— and n is 1, then R10 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C2-C4 alkoxymethyl or C2-C4 alkylthiomethyl;
(k) when at least one of R10 and R11 is haloalkyl, then R1a or R1b is CH2CH3 or CH2CF3 and R2a or R2b is tert-butyl, isopropyl or cyclopropyl;
(l) when J is J-2 or J-6, then R7 and R9 are H;
(m) when J is J-2 or J-6, and R2b is C1-C2 alkyl, then R1b is halogen, C2-C4 alkyl, C1-C4 fluoroalkyl, C2-C4 alkenyl, C2-C4 fluoroalkenyl, C2-C4 alkynyl or C2-C4 fluoroalkynyl;
(n) when R1a is CH3 and R5 is C(NOR14)R15, then R7 is other than alkyl;
(o) when T is N, then Z is CR9;
(p) when T is N and R7 is alkoxy, then R11 is H;
(q) when R7 and R9 are F, and one of R10 and R11 is H, then the other of R10 and R1 is other than H;
(r) when Z is N and one of R10 and R11 is H, then the other of R10 and R11 is other than trifluoroethyl;
(s) when J is J-8 and R2b is C5-C6 cycloalkyl, then R5 is C(O)NR10R11;
(t) when J is J-8 and R7 is other than H, then R2b is tert-butyl and R5 is C(O)NR10R11;
and
(u) when J is J-8, then R11 is other than 1-ethylpropyl.

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Azolecarboxamide herbicides

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Azolecarboxamide herbicides

Life of this patent

Abstract

Claims21