Herbicidal isoxazolo[5,4-B]pyridines

An isoxazolo[5,4-b]pyridine compound of formula I

• or the agriculturally useful salts of isoxazolo[5,4-b]pyridine compounds of formula I, wherein in formula I, the variables are as defined below:
• R1 is selected from the group consisting of hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl, and phenyl-C1-C6-alkyl;
• R2 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkyl-C3-C6-cycloalkyl, phenyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, amino, C1-C6-alkylamino, N,N-di-(C1-C6-alkyl)amino, and heterocyclyl, phenyl;
• wherein the heterocyclyl and phenyl moieties of R2 can be unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, and heterocyclyl, phenyl;
• or R1 and R2 together form an C3-C5-alkanediyl;
• R3 is selected from the group consisting of C3-C6-cycloalkyloxy-C1-C6-alkyl-, C3-C6-halocycloalkyloxy-C1-C6-alkyl-, phenoxy-C1-C6-alkyl-, heterocyclyloxy-C1-C6-alkyl-, phenyl-C1-C6-alkoxyl-C1-C6-alkyl, C1-C6-alkyl-carbonyloxy-C1-C6-alkyl-, amino-C1-C6-alkyl-, (C1-C6-alkyl)amino-C1-C6-alkyl-, N,N-di-(C1-C6-alkyl)amino-C1-C6-alkyl-, (C3-C6-cycloalkyl)amino-C1-C6-alkyl-, N,N-di-(C3-C6-cycloalkyl)amino-C1-C6-alkyl-, [N—(C1-C6-alkyl),N—(C3-C6-cycloalkyl)]amino-C1-C6-alkyl-, C1-C6-alkyl-carbonyl-C1-C6-alkyl-, C1-C6-alkoxy-C1-C6-haloalkyl-, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl-, formyl-, formyl-C1-C6-alkyl-, C1-C6-alkyl-carbonyl-, C3-C6-cycloalkyloxy-, C3-C6-halocycloalkyloxy-, C1-C6-alkyl-C3-C6-cycloalkyloxy-, C1-C6-alkyl-C3-C6-halocycloalkyloxy-, C1-C6-haloalkyl-C3-C6-cycloalkyloxy-, C1-C6-haloalkyl-C3-C6-halocycloalkyloxy-, C3-C6-cycloalkyl-C1-C6-alkoxy-, C3-C6-halocycloalkyl-C1-C6-alkoxy-, C3-C6-cycloalkyl-C1-C6-haloalkoxy-, C3-C6-halocycloalkyl-C1-C6-haloalkoxy-, C3-C6-alkenyloxy-, C3-C6-haloalkenyloxy-, C3-C6-alkynyloxy-, C3-C6-haloalkynyloxy-, C1-C6-alkoxy-C1-C6-alkoxy-, phenyl-C1-C6-alkoxy-, phenyl-C1-C6-haloalkoxy-, heterocyclyl-C1-C6-alkoxy-, heterocyclyl-C1-C6-haloalkoxy, phenoxy-, heterocyclyloxy-, phenylcarbonyloxy-, heterocyclylcarbonyloxy-, C3-C6-cycloalkylthio-, C3-C6-halocycloalkylthio-, C3-C6-cycloalkyl-C1-C6-alkylthio-, C3-C6-halocycloalkyl-C1-C6-alkylthio-, C3-C6-cycloalkyl-C1-C6-haloalkylthio-, C3-C6-halocycloalkyl-C1-C6-haloalkylthio-, heterocyclylthio-, phenylthio-, phenyl-C1-C6-alkylthio-, heterocyclyl-C1-C6-alkylthio-, C1-C6-alkylsulfonyl-, C1-C6-haloalkylsulfonyl-, C3-C6-cycloalkylsulfonyl-, C3-C6-halocycloalkylsulfonyl-, heterocyclylsulfonyl-, phenylsulfonyl-, phenyl-C1-C6-alkylsulfonyl-, heterocyclyl-, C1-C6-alkylsulfonyl-, C1-C6-alkylsulfinyl-, C1-C6-haloalkylsulfinyl-, C3-C6-cycloalkylsulfinyl-, C3-C6-halocycloalkylsulfinyl-, heterocyclylsulfinyl-, phenylsulfinyl-, phenyl-C1-C6-alkylsulfinyl-, heterocyclyl-C1-C6-alkylsulfinyl-, phenylamino-, heterocyclylamino-, [N—(C1-C6-alkyl), N-phenyl]amino-, [N—(C1-C6-alkyl),N—(C3-C6-cycloalkyl)]amino-, N—(C3-C6-cycloalkyl)amino-, N,N-di-(C3-C6-cycloalkyl)amino-, [N—(C1-C6-alkyl),N—(C3-C6-halocycloalkyl)]amino-, [N—(C1-C6-alkyl),N—(C1-C6-haloalkyl)]amino-, (C3-C6-halocycloalkyl)amino-, N,N-di-(C3-C6-halocycloalkyl)amino, [N—(C1-C6-alkyl),N-(phenyl-C1-C6-alkyl)]amino-, (phenyl-C1-C6-alkyl)amino-, (heterocyclyl-C1-C6-alkyl)amino-, N—[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, N,N-di-[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, N—[(C3-C6-halocycloalkyl)-(C1-C6-alkyl)]amino-, and N—(C1-C6-alkyl)-N—[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, wherein the heterocyclyl and phenyl moieties of R3 can be unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, hydroxy, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl-, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy-, C1-C6-alkoxycarbonyl-, C1-C6-alkylthio, C1-C6-alkylsulfinyl-, C1-C6-alkylsulfonyl, amino, C1-C6-alkylamino, N,N-di-(C1-C6-alkyl)amino, heterocyclyl, phenyl, and the moiety of formula II,
• wherein
• Q is hydrogen or C1-C6-alkyl;
• Y is a direct bond or C1-C6-alkanediyl;
• Re is selected from the group consisting of amino, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, C1-C6-alkyl-[(aminocarbonyl)amino]-, and C1-C6-haloalkyl-[(aminocarbonyl)amino];
• X is selected from the group consisting of OR4, SR5;
• NR6R7;
• R4, R5 are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy-C1-C6-alkyl-, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl-, C1-C6-haloalkoxy-C1-C6-alkyl-, C2-C6-alkenyloxy-C1-C6-alkyl-, C2-C6-haloalkenyloxy-C1-C6-alkyl-, C1-C6-alkoxycarbonyl-C1-C6-alkyl-, aminocarbonyl-C1-C6-alkyl-, C1-C6-alkyl-aminocarbonyl-C1-C6-alkyl-, N,N-di-(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkyl-, [N—(C3-C6-cycloalkyl-C1-C6-alkyl), N—(C1-C6-ALKYL)]-AMINOCARBONYL-C1-C6-ALKYL, C1-C6-ALKOXY-AMINOCARBONYL-C1-C6-ALKYL-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl-C2-C6-alkenyl-, C3-C6-alkynyl, C3-C6-haloalkynyl, heterocyclyl, phenyl, heterocyclylcarbonyl-, phenylcarbonyl-, heterocyclylcarbonyl-C1-C6-alkyl-, phenylcarbonyl-C1-C6-alkyl-, heterocyclyl-C1-C6-alkyl-, and phenyl-C1-C6-alkyl-;
• wherein the phenyl and heterocyclyl moieties of R4 and R5 can be unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, heterocyclyl, phenyl;
• R6, R7 is selected from the group consisting of hydrogen, C1-C6-alkyl, and C1-C6-haloalkyl.