Tricyclic carboxamides for controlling arthropods

Patent metadata

Field	Value
Publication number	US-11825838-B2
Application number	US-201816498674-A
Country	US
Kind code	B2
Filing date	Mar 26, 2018
Priority date	Mar 31, 2017
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

The invention relates, inter alia, to compounds of general formula (I). The invention also relates to methods for synthesizing the compounds of formula (I). The compounds according to the invention are in particular suitable for controlling insects, arachnids and nematodes in agricultural applications and for controlling ectoparasites in veterinary medicine.

First claim

The invention claimed is:

1. A compound of formula (I)

in which
R 1 is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 6 -,C 10 -,C 14 -aryl(C1-C3)-alkyl, 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl or 3, 4, 5, 6, 7, 8, 9 or 10-membered-heterocyclyl(C 1 -C 3 )-alkyl, optionally in each case mutually independently substituted by one or more substituents, selected from the group consisting of amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C 4 -carboxyl, carbonamide, SF 5 , aminosulfonyl, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 2 -C 4 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkylamino, N,N-di-C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkanoylamino, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkoxy, C 5 -C 6 -cycloalkenyloxy, C 1 -C 4 -alkoxycarbonyl, C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 -alkynyloxycarbonyl, C 6 -,C 10 -,C 14 -aryloxycarbonyl, C 1 -C 4 -alkanoyl, C 2 -C 4 -alkenylcarbonyl, C 2 -C 4 -alkynylcarbonyl, C 6 -,C 10 -,C 14 -arylcarbonyl, C 1 -C 4 -alkylsulfanyl, C 3 -C 4 -cycloalkylsulfanyl, C 1 -C 4 -alkylthio, C 2 -C 4 -alkenylthio, C 5 -C 6 -cycloalkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 4 -alkylsulfenyl and C 1 -C 4 -alkylsulfinyl, wherein both enantiomers of the C 1 -C 4 -alkylsulfinyl group are included, C 1 -C 4 -alkylsulfonyl, N-mono-C 1 -C 4 -alkylaminosulfonyl, N,N-di-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylphosphinyl, C 1 -C 4 -alkylphosphonyl, wherein for C 1 -C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl both enantiomers are included, N—C 1 -C 4 -alkylaminocarbonyl, N,N-di-C 1 -C 4 -alkylaminocarbonyl, N—C 1 -C 4 -alkanoylaminocarbonyl, N—C 1 -C 4 -alkanoyl-N—C 1 -C 4 -alkylaminocarbonyl, C 6 -,C 10 -,C 14 -aryl, C 6 -,C 10 -,C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C 6 -,C 10 -,C 14 -arylthio, C 6 -,C 10 -,C 14 -arylamino, benzylamino, heterocyclyl and trialkylsilyl;
R 2 is H or C 1 -C 6 -alkyl, optionally substituted by one or more substituents mutually independently selected from the group consisting of amino, hydroxyl, halogen, nitro, cyano, mercapto, C 1 -C 4 -carboxyl, carbonamide, aminosulfonyl, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 2 -C 4 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkylamino, N,N-di-C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkanoylamino, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkoxy, C 5 -C 6 -cycloalkenyloxy, C 1 -C 4 -alkoxycarbonyl, C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 -alkynyloxycarbonyl, C 6 -,C 10 -,C 14 -aryloxycarbonyl, C 1 -C 4 -alkanoyl, C 2 -C 4 -alkenylcarbonyl, C 2 -C 4 -alkynylcarbonyl, C 6 -,C 10 -,C 14 -arylcarbonyl, C 1 -C 4 -alkylsulfanyl, C 3 -C 4 -cycloalkylsulfanyl, C 1 -C 4 -alkylthio, C 2 -C 4 -alkenylthio, C 5 -C 6 -cycloalkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 4 -alkylsulfenyl and C 1 -C 4 -alkylsulfinyl, wherein both enantiomers of the C 1 -C 4 -alkylsulfinyl group are included, C 1 -C 4 -alkylsulfonyl, N-mono-C 1 -C 4 -alkylaminosulfonyl, N,N-di-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylphosphinyl, C 1 -C 4 -alkylphosphonyl, wherein both enantiomers are included for C 1 -C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl, N—C 1 -C 4 -alkylaminocarbonyl, N,N-di-C 1 -C 4 -alkylaminocarbonyl, N—C 1 -C 4 -alkanoylaminocarbonyl, N—C 1 -C 4 -alkanoyl-N—C 1 -C 4 -alkylaminocarbonyl, C 6 -,C 10 -,C 14 -aryl, C 6 -,C 10 -,C 14 -aryloxy, benzyloxy, benzylthio, C 6 -,C 10 -,C 14 -arylthio, C 6 -,C 10 -,C 14 -arylamino, benzylamino, heterocyclyl and trialkylsilyl;
the moieties
A 1 , A 2 and A 3 are each independently N, O, CR 3 , S or N—R 4 , wherein A 1 , A 2 , A 3 , Z and the carbon atom of the ring form an aromatic system;
R 3 is each independently H, Cl, F, I, Br or optionally halogenated C 1 -C 4 -alkyl;
R 4 is each independently H or optionally halogenated C 1 -C 4 -alkyl;
Q is O or S;
Z is C or N;
B 1 , B 2 , B 4 , and B 5 are each independently C—R 5 and
wherein
R 5 is each independently H, halogen, cyano, nitro, SF 5 , C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, N—C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 -alkylamino, in each case optionally substituted by one or more substituents selected from the group consisting of amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C 4 -carboxyl, carbonamide, SF 5 , aminosulfonyl, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 2 -C 4 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkylamino, N,N-di-C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkanoylamino, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkoxy, C 5 -C 6 -cycloalkenyloxy, C 1 -C 4 -alkoxycarbonyl, C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 -alkynyloxycarbonyl, C 6 -,C 10 -,C 14 -aryloxycarbonyl, C 1 -C 4 -alkanoyl, C 2 -C 4 -alkenylcarbonyl, C 2 -C 4 -alkynylcarbonyl, C 6 -,C 10 -,C 14 -arylcarbonyl, C 1 -C 4 -alkylsulfanyl, C 3 -C 4 -cycloalkylsulfanyl, C 1 -C 4 -alkylthio, C 2 -C 4 -alkenylthio, C 5 -C 6 -cycloalkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 4 -alkylsulfenyl and C 1 -C 4 -alkylsulfinyl, wherein both enantiomers of the C 1 -C 4 -alkylsulfinyl group are included, C 1 -C 4 -alkylsulfonyl, N-mono-C 1 -C 4 -alkylaminosulfonyl, N,N-di-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylphosphinyl, C 1 -C 4 -alkylphosphonyl, wherein both enantiomers are included for C 1 -C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl, N—C 1 -C 4 -alkylaminocarbonyl, N,N-di-C 1 -C 4 -alkylaminocarbonyl, N—C 1 -C 4 -alkanoylaminocarbonyl, N—C 1 -C 4 -alkanoyl-N—C 1 -C 4 -alkylaminocarbonyl, C 6 -,C 10 -,C 14 -aryl, C 6 -,C 10 -,C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C 6 -,C 10 -,C 14 -arylthio, C 6 -,C 10 -,C 14 -arylamino, benzylamino, heterocyclyl and trialkylsilyl;
B 3 is CR 5 , wherein R 5 is perhalogenated C 1 -C 4 -alkyl;
T is one of the following listed 5-membered heteroaromatics T1-T4 and T6,
wherein the bond to

is marked with a hash #,

and/or a salt, N-oxide and/or tautomeric form of a compound of formula (I).

2. The compound as claimed in claim 1 , wherein R 2 is H or methyl.

3. The compound as claimed in claim 1 , wherein T is T1, T2 or T4.

4. The compound as claimed in claim 1 , wherein R 1 is benzyl, cyclopropyl or 1-CN-cyclopropyl.

5. The compound as claimed in claim 1 , wherein the compound is a compound according to one of formulae of formula (Ia), (Ib), (1j), or (1k)

wherein V is N(R 1 R 2 ).

6. The compound as claimed in claim 1 , wherein the compound is a compound of formula (I′a)

7. The compound as claimed in claim 1 , wherein the compound is a compound of formula (I′b)

8. The compound as claimed in claim 1 , wherein the compound is a compound of formula (I′c)

Assignees

• Bayer Cropscience Ag

Inventors

• Harschneck Tobias
• Arlt Alexander
• Velten Robert
• Maue Michael
• Ilg Kerstin
• Hallenbach Werner
• Goergens Ulrich
• Horstmann Sebastian
• Loesel Peter
• Turberg Andreas

Classifications

• A01N33/26 Primary

  containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title