# US 9,750,256 B2 · Herbicidal isoxazolo[5,4-B]pyridines

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- Number: US 9,750,256 B2
- Document ID: US9750256B2
- Status: Granted
- Kind: B2
- Application number: 14/371,620
- Filed: 2013-01-04
- Published: 2015-02-05
- Granted: 2017-09-05
- Earliest claimed: 2012-01-12
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Anna Aleksandra Michrowska-Pianowska; Markus Kordes; Johannes Hutzler; Trevor William Newton; Richard Roger Evans; Klaus Kreuz; Klaus Grossmann; Thomas Seitz; Andree van der Kloet; Matthias Witschel; Liliana Parra Rapado; Jens Lerchl
- Web page: https://patentgrep.com/patent/US9750256B2

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 498/04: Ortho-condensed systems
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to isoxazolo[5,4-b]pyridine compounds of formula I, to the agriculturally useful salts of isoxazolo[5,4-b]pyridine compounds of formula I, and to their use as herbicides.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The compound of claim 1, wherein in formula I
R1 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, and C1-C6-haloalkyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein in formula I
R1 is hydrogen.

### Claim 4 (depends on 1)

The compound of claim 1, wherein in formula I
R2 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, and C2-C6-alkynyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein in formula I
R2 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein in formula I
R3 is selected from the group consisting of C3-C6-cycloalkyloxy-C1-C6-alkyl-, C3-C6-halocycloalkyloxy-C1-C6-alkyl-, phenoxy-C1-C6-alkyl-, heterocycyloxy-C1-C6-alkyl-, phenyl-C1-C6-alkoxy-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-, C1C-aoloyC1C-aoly_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-, C1-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-cycloakyl-C1-C6-haloalkylthio-, C3-C6-halocycloalkyl-C1-C6-haloalkylthio-, heterocyclylthio-, phenylthio-, phenyl-C1-C6-alkylthio-, heterocyclyl-C1-C6-alkylthio-, 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-alkylamino-, (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-, 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 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;
R3 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]-.

### Claim 7 (depends on 1)

The compound of claim 1, wherein in formula I
R3 is selected from the group consisting of C1-C6-alkyl-carbonyloxy-C1-C6-alkyl-, C1-C6-alkyl-carbonyl-C1-C6-alkyl-, formyl, formyl-C1-C6-alkyl-, C3-C6-cycloalkyloxy-, C3-C6-halocycloalkyloxy-, C3-C6-cycloalkyl-C1-C6-alkoxy-, C3-C6-alkenyloxy-, C3-C8-alkynyloxy-, C1-C6-alkoxy-C1-C6-alkoxy-, phenyl-C1-C6-alkoxy-, phenoxy, heterocyclyloxy-, phenylcarbonyloxy-, C3-C6-cycloalkylthio-, phenylthio-, phenyl-C1-C6-alkylthio-, phenylamino-, N—(C3-C6-cycloalkyl)amino-, N—[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, wherein the phenyl moieties of R3 can be unsubstituted or substituted with C1-C6-haloalkyl, and the moiety of formula II,
wherein
Q is hydrogen or C1-C6-alkyl;
Y is a direct bond or C1-C6-alkanediyl;
R3 is selected from the group consisting of amino, hydroxy, C1-C6-alkoxy, C1-C6-alkyl-[(aminocarbonyl)amino]-, and C1-C6-haloalkyl-[(aminocarbonyl)amino]-.

### Claim 8 (depends on 1)

The compound of claim 1, wherein in formula I
X is OR4, SR5.

### Claim 9 (depends on 1)

The compound of claim 1, wherein in formula I
X is OR4;
R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy-C1-C6-alkyl-, C1-C6-haloalkoxy-C1-C6-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, and C3-C6-alkynyl.

### Claim 10 (depends on 1)

The compound of claim 1, wherein in formula I
R4 is hydrogen.

### Claim 11 (depends on 1)

The compound of claim 1, wherein in formula I
X is SR5;
R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, phenyl-C1-C6-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, and C3-C6-alkynyl.

### Claim 12 (depends on 1)

A composition comprising a herbicidally active amount of at least one isoxazolo[5,4-b]pyridine compound of formula I or an agriculturally useful salt of formula I as defined in claim 1, and auxiliaries customary for formulating crop protection agents.

### Claim 13 (depends on 12)

A method for preparing the composition of claim 12, comprising mixing a herbicidally active amount of at least one isoxazolo[5,4-b]pyridine compound of formula I or an agriculturally useful salt of formula I and auxiliaries customary for formulating crop protection agents.

### Claim 14 (depends on 1)

A method for controlling unwanted vegetation, comprising allowing a herbicidally effective amount of at least one isoxazolo[5,4-b]pyridine compound of formula I or an agriculturally useful salt of I as defined in claim 1 to act on plants, their seeds and/or their habitat.

### Claim 15 (depends on 12)

A method for controlling unwanted vegetation, comprising allowing a herbicidally effective amount of the composition of claim 12 to act on plants, their seeds and/or their habitat.

### Claim 16 (depends on 14)

The method of claim 14, wherein in formula I
X is OR4, SR5.

### Claim 17 (depends on 14)

The method of claim 14, wherein in formula I
X is OR4;
R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy-C1-C6-alkyl-, C1-C6-haloalkoxy-C1-C6-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, and C3-C6-alkynyl.

### Claim 18 (depends on 14)

The method of claim 14, wherein in formula I
R4 is hydrogen.

### Claim 19 (depends on 14)

The method of claim 14, wherein in formula I
X is SR5;
R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, phenyl-C1-C6-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, and C3-C6-alkynyl.

### Claim 20 (depends on 14)

The method of claim 14, wherein in formula I
R2 is C3-C6-cycloalkyl, C3-C6-halocycloalkyl.

### Claim 21 (depends on 14)

The method of claim 14, wherein in formula I
R6 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-alkoxy-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-, 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-, N—(C1-C6-alkyl)-N—[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, wherein the heterocyclyl and phenyl moieties of R, can be unsubstituted or substituted with one or more radicals selected from halogen, hydroxy, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl-, C3-C6-cycloalkyl, C2-C6-alkenyl, C1-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)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;
R8 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]-.

### Claim 22 (depends on 14)

The method of claim 14, wherein in formula I
R3 is selected from the group consisting of C1-C6-alkyl-carbonyloxy-C1-C6-alkyl-, C1-C6-alkyl-carbonyl-C1-C6-alkyl-, formyl, formyl-C1-C6-alkyl-, C3-C6-cycloalkyloxy-, C3-C6-halocycloalkyloxy-, C3-C6-cycloalkyl-C1-C6-alkoxy-, C3-C6-alkenyloxy-, C3-C6-alkynyloxy-, C1-C6-alkoxy-C1-C6-alkoxy-, phenyl-C1-C6-alkoxy-, phenoxy-, heterocyclyloxy-, phenylcarbonyloxy-, C3-C6-cycloalkylthio-, phenylthio-, phenyl-C1-C6-alkylthio-, phenylamino-, N—(C3-C6-cycloalkyl)amino-, N—[(C3-C6-cycloalkyl)-(C1-C6-alkyl)]amino-, wherein the phenyl moieties of R3 can be unsubstituted or substituted with C1-C6-haloalkyl, and the moiety of formula II,
wherein
Q is hydrogen or C1-C6-alkyl;
Y is a direct bond or C1-C6-alkanediyl;
R6 is selected from the group consisting of amino, hydroxy, C1-C6-alkoxy, C1-C3-alkyl-[(aminocarbonyl)amino]-, and C1-C6-haloalkyl-[(aminocarbonyl)amino]-.