Sulfonylaminobenzamide compounds
View Patent ↗The present invention relates to a new compound of formula (I) wherein the variables have the meaning as indicated in the claims; or an enantiomer or salt thereof. The compounds of formula (I) are useful in the control of parasites, in particular endoparasites, in and on vertebrates.
1. A compound of formula
or a salt or an enantiomer thereof, wherein
X is O, S, NH, C(O), C(CN) or CH═CH;
R 0 is H, C 1 -C 4 -alkyl or hydroxyl;
n is 0 or 1;
each R is independently halogen; C 1 -C 6 -alkyl; C 1 -C 6 -haloalkyl; C 3 -C 6 -cycloalkyl; C 3 -C 6 -halocycloalkyl; amino; N-mono- or N,N-di-C 1 -C 4 -alkylamino; hydroxy; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy; C 1 -C 6 -alkylthio; C 1 -C 6 -haloalkylthio; C 1 -C 6 -alkyl-sulfinyl; C 1 -C 6 -haloalkylsulfinyl; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl; SF 5 ; tri-C 1 -C 4 -alkylsilyl; C 1 -C 6 -alkoxycarbonyl; aminocarbonyl; N-mono- or N,N-di-C 1 -C 6 -alkylaminocarbonyl; aminosulfonyl; N-mono- or N,N-di-C 1 -C 6 -alkylaminosulfonyl; N—C 1 -C 6 -alkylsulfonylamino; C 1 -C 6 -alkoxycarbonylamino; N-C 1 -C 4 -alkyl-N-C 1 -C 6 -alkoxycarbonylamino; cyano; nitro; or C 3 -C 6 -heterocyclyl which is unsubstituted or substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cyclolalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, cyano or nitro;
m is an integer from 0 to 4;
each R 1 is independently halogen; C 1 -C 6 -alkyl; C 1 -C 6 -haloalkyl; C 3 -C 6 -cycloalkyl; C 3 -C 6 -halocycloalkyl; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy; C 1 -C 6 -alkylthio; C 1 -C 6 -haloalkylthio; C 1 -C 6 -alkyl-sulfinyl; C 1 -C 6 -haloalkylsulfinyl; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl; SF 5 ; amino; N-mono- or N,N-di-C 1 -C 6 -alkylamino; tri-C 1 -C 4 -alkylsilyl; C 1 -C 6 -alkoxycarbonyl; aminocarbonyl; N-mono- or N,N-di-C 1 -C 6 -alkylaminocarbonyl; N,N-di-C 1 -C 4 -alkylamino-C 1 -C 4 -alkylaminocarbonyl; aminosulfonyl; N-mono- or N,N-di-C 1 -C 6 -alkylaminosulfonyl; N—C 1 -C 6 -alkylsulfonylamino; C 1 -C 6 -alkoxycarbonylamino; N—C 1 -C 4 -alkyl-N—C 1 -C 6 -alkoxycarbonylamino; cyano; nitro; hydroxy; B(OH) 2 ; or phenyl, benzoyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -heterocyclyloxy or C 6 -C 8 -benzoheterocyclyl, which is each unsubstituted or substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, cyano or nitro; and
r is an integer of from 1 to 4.
2. A compound of formula (I) according to claim 1 , wherein each R is independently halogen; C 1 -C 4 -alkyl; C 1 -C 4 -haloalkyl; amino; C 1 -C 4 -alkoxy; C 1 -C 4 -haloalkoxy; C 1 -C 4 -haloalkylthio; C 1 -C 4 -alkylsulfonyl; C 1 -C 4 -haloalkylsulfonyl; tri-C 1 -C 2 -alkylsilyl; C 1 -C 4 -alkoxycarbonyl; N-mono- or N,N-di-C 1 -C 4 -alkylaminocarbonyl; aminosulfonyl; N-mono- or N,N-di-C 1 -C 4 -alkylaminosulfonyl; N—C 1 -C 2 -alkyl-N—C 1 -C 4 -alkoxycarbonylamino; cyano; nitro; or 5- or 6-membered heterocycloalkyl comprising 1 or 2 same or different heteroatoms selected from O, S and N, which is unsubstituted or substituted by halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -alkoxy.
3. A compound of formula (I) according to claim 1 , wherein each R is halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy or cyano.
4. A compound of formula (I) according to claim 3 , wherein m is an integer 1, 2 or 3.
5. A compound of formula (I) according to claim 4 , wherein each R 1 is independently halogen; C 1 -C 4 -alkyl; C 1 -C 4 -haloalkyl; C 3 -C 6 -cycloalkyl; C 1 -C 4 -alkoxy; C 1 -C 4 -haloalkoxy; C 1 -C 4 -haloalkylthio; SF 5 ; N,N-di-C 1 -C 4 -alkylamino-C 1 -C 4 -alkylaminocarbonyl; N—C 1 -C 4 -alkylsulfonylamino; cyano; nitro; hydroxy; B(OH) 2 ; morpholino; or phenyl, benzoyl, pyridyloxy, pyrimidinyloxy or benzothiazloyl, which is each unsubstituted or substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl or C 1 -C 4 -alkoxy.
6. A compound of formula (I) according to claim 4 , wherein each R 1 is independently halogen; C 1 -C 2 -alkyl; C 1 -C 3 -haloalkyl; C 1 -C 2 -alkoxy; C 1 -C 3 -haloalkoxy; C 1 -C 2 -haloalkylthio; SF 5 ; nitro; or hydroxy.
7. A compound of formula (I) according to claim 6 , wherein r is an integer of 1, 2 or 3.
8. A compound of formula (I) according to claim 1 , wherein R 0 is H, m is 0 or 1 and X is O.
9. A compound according to claim 1 of formula
wherein R and m are each as defined in claim 1 .
10. A compound according to claim 1 of formula
wherein R, R 1 , m and r are each as defined in claim 1 .
11. A compound of formula (Ib) according to claim 10 , wherein m is an integer 1 or 2, r is an integer 2 or 3, each R is independently halogen or CF 3 , and each R 1 is independently halogen or CF 3 .
12. A composition for the control of parasites, which contains as active ingredient at least one compound of formula (I) according to claim 1 , in addition to carriers and/or dispersants.
13. A method of controlling endoparasites, on warm-blooded animals, which comprises administering to the warm-blooded animals a veterinary effective amount of at least one compound of formula (I) according to claim 1 .