Microbiocidal oxadiazole derivatives

Patent metadata

Field	Value
Publication number	US-10798941-B2
Application number	US-201716068638-A
Country	US
Kind code	B2
Filing date	Jan 5, 2017
Priority date	Jan 8, 2016
Publication date	Oct 13, 2020
Grant date	Oct 13, 2020

Abstract

Compounds of the formula (I) wherein the substituents are as defined in claim 1 , useful as a pesticides, especially fungicides.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein
n is 1 or 2;
A 1 represents N or CR 1 , wherein R 1 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
A 2 represents N or CR 2 , wherein R 2 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
A 3 represents N or CR 3 , wherein R 3 represents hydrogen or halogen;
A 4 represents N or CR 4 , wherein R 4 represents hydrogen or halogen; and
wherein 0 or 1 or 2 of A 1 , A 2 , A 3 and A 4 are N;
R 5 and R 6 are independently selected from hydrogen, C 1-4 alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, or
R 5 and R 6 together with the carbon atom they share form a cyclopropyl;
Z is selected from Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z 6 ; wherein
Z 1 represents a heterocyclyl linked to C(R 5 )(R 6 ) via a C—C bond, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which contains 1 nitrogen in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, NR 7 , C(O), or S(O) 2 , with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S;
Z 2 represents a heteroaryl linked to C(R 5 )(R 6 ) via a C—C bond, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which contains 1 nitrogen atom in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, or NR′;
R 7 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, formyl, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, N—C 1-4 alkylaminocarbonyl, N,N-diC 1-4 alkylaminocarbonyl, C 1-4 alkylsulfonyl, N—C 1-2 alkylaminosulfonyl, or N,N-diC 1-2 alkylaminosulfonyl; and
wherein for Z 1 and Z 2 , the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 8 ;
R 8 is cyano, halogen, hydroxy, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, C 2-4 haloalkenyl, C 1-4 alkoxy, C 1-4 haloalkoxy, C 3-4 alkenyloxy, C 3-4 alkynyloxy, N—C 1-4 alkylamino, N,N-diC 1-4 alkylamino, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, C 1-4 alkylcarbonylamino, N—C 1-4 alkylaminocarbonyl, N,N-diC 1-4 alkylaminocarbonyl or C 1-4 alkoxycarbonylamino;
Z 3 represents a heterocyclyl linked to C(R 5 )(R 6 ) via a C—N bond, wherein the heterocyclyl moiety is selected from imidazolidinyl, pyrazolidinyl, oxazolidinyl, isoxazolidinyl, 4,5-dihydrooxazolyl, thiazolidinyl, thiazolinyl and thiomorpholinyl;
Z 4 represents a heteroaryl linked to C(R 5 )(R 6 ) via a C—N bond, wherein the heteroaryl moiety is a 5-membered aromatic ring which contains 1 to 4 nitrogen atoms in the ring system; and
wherein for Z 3 and Z 4 , the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 10 ;
wherein R 10 represents:
(i) cyano, halogen, hydroxy, amino, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, C 2-4 haloalkenyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, C 1-4 haloalkoxy, C 1-4 alkylsulfanyl, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylsulfanyl, C 3-4 alkenyloxy, C 3-4 alkynyloxy, N—C 1-4 alkylamino, N,N-diC 1-4 alkylamino, formyl, hydroxycarbonyl, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, C 1-4 alkylcarbonylamino, aminocarbonyl, N—C 1-4 alkylaminocarbonyl, N—C 2-4 alkenylaminocarbonyl, N—C 2-4 alkynylaminocarbonyl, N,N-diC 1-4 alkylaminocarbonyl, N-morpholinoaminocarbonyl, 4alkoxyaminocarbonyl, N—C 1-4 alkyl-N—C 1-4 alkoxyaminocarbonyl, C 1-4 alkoxycarbonylamino, C 1-4 alkoxycarbonylaminoC 1-4 alkyl, N—C 1-4 alkoxyC 1-4 alkylaminocarbonyl, phenylcarbonyloxyC 1-4 alkyl, phenylcarbonylaminoC 1-4 alkyl, C 1-4 alkylcarbonyloxy, C 1-4 haloalkylcarbonyloxy, C 1-4 alkylcarbonyloxyC 1-4 alkyl, C 1-4 alkylcarbonylaminoC 1-4 alkyl, or (C 1-4 alkyl) 3 Si—; or
(ii) —C(O)N(R a )(R b ), wherein:
R a is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-5 alkenyl, C 3-5 alkynyl, aminoC 1-4 alkyl, N—C 1-4 alkylaminoC 1-4 alkyl, N,N-diC 1-4 alkylaminoC 1-4 alkyl, formyl, C 1-4 alkylcarbonyl, C 3-4 cycloalkylcarbonyl, C 1-4 haloalkylcarbonyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylcarbonyloxyC 1-4 alkyl, N—C 1-4 alkylaminocarbonylC 1-4 alkyl, N,N-diC 1-4 alkylaminocarbonylC 1-4 alkyl, C 1-4 alkylsulfanylC 1-4 alkyl, C 1-4 alkylsulfonyl, C 1-4 alkylsulfonylC 1-4 alkyl, C 1-4 alkylsulfonylaminoC 1-4 alkyl, C 1-4 alkoxycarbonylaminoC 1-4 alkyl, C 1-4 alkylcarbonylaminoC 1-4 alkyl, C 1-4 alkoxycarbonylaminoC 1-4 alkyl, or C 1-4 haloalkylcarbonylaminoC 1-4 alkyl, and
R b is hydrogen, hydroxyl, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 3-4 cycloalkyl, C 3-4 cycloalkylC 1-2 alkyl, C 1-4 alkoxy, C 3-4 alkenyloxy, C 3-4 haloalkenyloxy, or C 3-4 alkynyloxy; or
R a and R b together with the nitrogen atom to which they are bonded, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O) 2 , C(O) and NR c , wherein R c is hydrogen, methyl, methoxy, formyl or acyl; or
(iii) —C(O)O—R d , wherein:
R d is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 1-2 alkoxyC 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-5 alkenyl, C 3-4 haloalkenyl, C 3-4 alkenyloxyC 1-4 alkyl, C 3-5 alkynyl, C 3-4 alkynyloxyC 1-4 alkyl, N—C 1-3 alkylaminoC 1-4 alkyl, N,N-di-C 1-3 alkylaminoC 1-4 alkyl, C 1-4 alkoxycarbonylaminoC 1-4 alkyl or C 1-4 alkylcarbonylaminoC 1-4 alkyl; or
wherein for Z 4 , the heteroaryl moiety is optionally substituted by 1 substituent selected from R 11 and further optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 10 ;
wherein R 11 represents:
(i) C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-2 alkyl, N—C 3-8 cycloalkylaminocarbonyl, N—C 3-8 cycloalkylC 1-2 alkylaminocarbonyl, phenyl, phenylC 1-2 alkyl, phenoxyC 1-2 alkyl, phenylC 1-2 alkylsulfanyl, heteroaryl, heteroarylC 1-2 alkyl, heteroaryloxyC 1-2 alkyl, N-heteroarylaminocarbonyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC 1-6 alkyl, heterocyclylcarbonyl wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, benzodioxolyl, and wherein any of said cycloalkyl, phenyl, heteroaryl, heterocyclyl and benzodioxolyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 12 ; or
(ii) —C(O)N(R e )(R f ), wherein:
R e is C 3-5 cycloalkyl, C 3-5 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heterocyclyl, heterocyclylC 1-2 alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O) 2 , with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N,

Assignees

• Syngenta Participations Ag

Inventors

• Hoffman Thomas James
• Stierli Daniel
• JEANGUENAT ANDRé
• Beaudegnies Renaud
• Pouliot Martin

Classifications

• C07D473/08

  with methyl radicals in positions 1 and 3, e.g. theophylline · CPC title

• C07D417/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title