US 2026/0293899 A1Published application

Imidazo[1,2-a]pyridine derivative

AssigneeSyngenta Crop Protection AG

InventorsMartin POULIOT, Stephane Andre Marie JEANMART, Nicolas GERMAIN, Damien BONVALOT

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Abstract

The current invention relates to compounds of the formula (I), wherein the substituents are as defined in claim 1, to processes and methods for preparing compounds of formula (I), to agrochemical compositions comprising compounds of formula (I) as defined in claim 1, to preparation of these compositions and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

Claims16

Dependent claims

A compound of formula (I)

wherein Z is O or S, and preferably Z is O;
A1 is CH or N, and preferably A1 is N;
R1, R1b and R1c are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C3-6cycloalkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl-C1-4alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxy, amino, and —NHC(O)C1-6alkyl;
A2 are independently CR2 or N, with the proviso that no more than three A2 are N, preferably no more than two A2 are N, preferably no more than one A2 is N, and more preferably the four A2 are CR2;
R2 are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
A3 is CR3 or N;
R3 is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
R4 is selected from heteroaryl-C1-4alkyl, and aryl-C1-4alkyl;
wherein the heteroaryl or the aryl is optionally substituted with one to three substituents independently selected from halogen, CN, C1-4alkyl, C1-4alkoxy, C3-6cycloalkyl, C1-4haloalkyl, C1-4cyanoalkyl, C1-4alkoxy-C1-4alkyl, C3-6halocycloalkyl, C3-6cyanocycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-4alkoxy-C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl is optionally substituted with halogen, CN, C1-4alkyl, C1-4alkoxy, and C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl, and A3 taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle;
and
R5 is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1-6alkylamino, diC1-6alkylamino, C1-6alkoxyamino, and C1-6alkylC1-6alkoxyamino, wherein each of the C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1-6alkylamino, diC1-6alkylamino, C1-6alkoxyamino, and C1-6alkylC1-6alkoxyamino groups is optionally substituted with one to three substituents independently selected from halogen and CN;
or a salt or N-oxide thereof.

11 more elements

A compound of formula (II)

wherein Z is O or S, and preferably Z is O;
R1a, R1b and R1c are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C3-6cycloalkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl-C1-4alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxy, amino, and —NHC(O)C1-6alkyl;
preferably R1a and R1c are hydrogen;
A2 are independently CR2 or N, with the proviso that no more than three A2 are N, preferably no more than two A2 are N, preferably no more than one A2 is N, and more preferably the four A2 are CR2;
R2 are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
and preferably R2 are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one substituent selected from halogen, hydroxy, and CN;
A3 is CR3 or N;
R3 is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
and preferably R3 is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino groups is optionally substituted with one substituent selected from halogen, hydroxy, and CN;
and more preferably R3 is hydrogen;
R4 is selected from heteroaryl-C1-4alkyl, and aryl-C1-4alkyl;
wherein the heteroaryl or the aryl is optionally substituted with one to three substituents independently selected from halogen, CN, C1-4alkyl, C1-4alkoxy, C3-6cycloalkyl, C1-4haloalkyl, C1-4cyanoalkyl, C1-4alkoxy-C1-4alkyl, C3-6halocycloalkyl, C3-6cyanocycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-4alkoxy-C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl is optionally substituted with halogen, CN, C1-4alkyl, C1-4alkoxy, and C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl, and A3 taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle;
and
X is Cl, Br or I;
or a salt or N-oxide thereof.

14 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound of formula (I)

wherein Z is O or S, and preferably Z is O;
A1 is CH or N, and preferably A1 is N;
R1, R1b and R1c are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C3-6cycloalkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl-C1-4alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxy, amino, and —NHC(O)C1-6alkyl;
A2 are independently CR2 or N, with the proviso that no more than three A2 are N, preferably no more than two A2 are N, preferably no more than one A2 is N, and more preferably the four A2 are CR2;
R2 are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
A3 is CR3 or N;
R3 is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;
R4 is selected from heteroaryl-C1-4alkyl, and aryl-C1-4alkyl;
wherein the heteroaryl or the aryl is optionally substituted with one to three substituents independently selected from halogen, CN, C1-4alkyl, C1-4alkoxy, C3-6cycloalkyl, C1-4haloalkyl, C1-4cyanoalkyl, C1-4alkoxy-C1-4alkyl, C3-6halocycloalkyl, C3-6cyanocycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-4alkoxy-C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl is optionally substituted with halogen, CN, C1-4alkyl, C1-4alkoxy, and C3-6cycloalkyl;
wherein the C1-4alkyl of said heteroaryl-C1-4alkyl or the C1-4alkyl of said aryl-C1-4alkyl, and A3 taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle;
and
R5 is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1-6alkylamino, diC1-6alkylamino, C1-6alkoxyamino, and C1-6alkylC1-6alkoxyamino, wherein each of the C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1-6alkylamino, diC1-6alkylamino, C1-6alkoxyamino, and C1-6alkylC1-6alkoxyamino groups is optionally substituted with one to three substituents independently selected from halogen and CN;
or a salt or N-oxide thereof.

11 more elements