US 9,809,587 B2
Pesticidally active heterocyclic derivatives with sulphur containing substituents
Andre Stoller, Stein (CH); Andre Jeanguenat, Stein (CH); Andrew Edmunds, Stein (CH); Pierre Joseph Marcel Jung, Stein (CH); Daniel Emery, Stein (CH); Michel Muehlebach, Stein (CH); and Peter Renold, Stein (CH)
Assigned to Syngenta Participations AG, Basel (CH)
Appl. No. 15/505,758
Filed by Syngenta Participations AG, Basel (CH)
PCT Filed Aug. 18, 2015, PCT No. PCT/EP2015/068953
§ 371(c)(1), (2) Date Feb. 22, 2017,
PCT Pub. No. WO2016/030229, PCT Pub. Date Mar. 3, 2016.
Claims priority of application No. 14182118 (EP), filed on Aug. 25, 2014; and application No. 15159505 (EP), filed on Mar. 17, 2015.
Prior Publication US 2017/0267672 A1, Sep. 21, 2017
Int. Cl. C07D 401/02 (2006.01); C07D 401/14 (2006.01); A61K 31/437 (2006.01); A61K 31/4353 (2006.01); C07D 417/10 (2006.01); A01N 43/90 (2006.01); C07D 471/04 (2006.01); C07D 487/02 (2006.01); C07F 5/02 (2006.01)
CPC C07D 417/10 (2013.01) [A01N 43/90 (2013.01); C07D 471/04 (2013.01); C07D 487/02 (2013.01); C07F 5/02 (2013.01)] 11 Claims
 
1. A compound of formula I,

OG Complex Work Unit Drawing
wherein
A represents CH or N;
Q is a five- to ten-membered monocyclic or fused bicyclic heterocyclic ring system which can be aromatic, partially saturated or fully saturated and which contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five- to ten-membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, oxo, OH, NH2, C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6alkylamino, C1-C6di-alkylamino, C1-C6alkoxycarbonylamino, C1-C4halo-alkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C6alkylcarbonyl, C1-C6halo-alkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C1-C6alkyl, di-C1-C4alkyl-phosphinoylmethyl-aminocarbonyl, C1-C6alkoxycarbonylamino, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylamino and C1-C6di-alkylamino;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl or C3-C6cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl; or R1 is C3-C6cycloalkyl-C1-C4alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl;
or R1 is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl;
R2 is halogen, cyano, C1-C6haloalkyl or C1-C6haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano;
or R2 is C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, O(C1-C4haloalkyl), or —C(O)C1-C4haloalkyl;
or R2 is C3-C6cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl;
X1 is O, S or NR3, wherein R3 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy-
C1-C4alkyl or C3-C6cycloalkyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.