IP Library › Granted Patent US 7,964,621

Granted Patent B2

US 7,964,621 · App. 12/582,486 · Granted Jun 21, 2011

Thioamide compounds, method of making and method of using thereof

Assignee: Merial Limited

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Quick Facts

Patent No.: US 7,964,621
App. No.: 12/582,486
Granted: Jun 21, 2011
Kind: B2

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Abstract

The present invention relates to novel thioamide derivatives of formula (I) and formula (Ia): wherein, R 3 , R 4 , R 5 , R 6 , R 7 , P, Q, T, V, W, X, Y, Z, a, m and n are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.

Claims (196)

1. A thioamide compound of formula (I):

wherein

R 1 , R 2 , R 8 , R 9 , R 10 and R 11 , independently of one another, are hydrogen, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, halo C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo C 1 -C 6 -alkylsulfonyl, SF 5 , arylthio, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, unsubstituted or substituted aryl, or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo-C 1 -C 6 -alkylsulfonyl, SF 5 , and methylthioamino;

R 3 , R 4 and R 5 , independently of one another, are hydrogen, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl; C 3 -C 7 -cycloalkyl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of halogen and C 1 -C 6 -alkyl; and phenyl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo-C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

or R 4 and R 5 together signify C 2 -C 6 -alkylene;

R 6 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthiocarbonyl or benzyl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo-C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

R 7 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthiocarbonyl, phenyl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino; heteroaryl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino; or naphtyl or quinlyl that is either unsubstituted or substituted, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

P is C—R 1 or N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 or N;

X is C—R 10 or N;

Y is C—R 11 or N;

Z is a direct bond, C(O), C(S) or S(O) p ;

a is 1, 2 or 3; and

P is 1 or 2.

2. The compound of claim 1 , wherein:

P and Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 8 , R 9 , R 10 and R 11 , independently of one another, are cyano, nitro, halogen, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, halo C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo C 1 -C 6 -alkylsulfonyl, SF 5 , arylthio, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo-C 1 -C 6 -alkylsulfonyl, SF 5 , and methylthioamino;

R 3 , R 4 and R 6 are H;

R 5 is methyl or C 1 -C 3 -alkyl;

R 7 is unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino; unsubstituted or substituted heteroaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

Z is a direct bond, C(O), C(S) or S(O) p ; and

a is 1.

3. The compound of claim 1 , wherein:

P and Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 8 , R 9 , R 10 and R 11 , independently of one another, is cyano, nitro, halogen, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, halo C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo C 1 -C 6 -alkylsulfonyl, SF 5 , arylthio, C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyloxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, halo-C 1 -C 6 -alkylsulfonyl, SF 5 , and methylthioamino;

R 3 , R 4 and R 6 is H;

R 5 is methyl or C 1 -C 3 -alkyl;

unsubstituted or substituted heteroaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfinyl, halo-C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, SF 5 , C 1 -C 6 -alkylamino, and di(C 1 -C 6 -alkyl)amino;

Z is C(O);

a is 1.

4. The compound of claim 1 , wherein:

P and Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

Z is C(O)

a is 1;

m and n are independently 0 or 1.

5. The compound of claim 1 , wherein:

R 1 , R 2 , R 8 , R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, halogen, halomethyl or methylthioamino;

R 3 , R 4 and R 6 is H;

R 5 is methyl or C 1 -C 3 -alkyl;

P is C—R 1 or N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 or N;

Z is C(O); and

a is 1.

6. The compound of claim 1 , wherein:

R 1 , R 2 , R 8 , R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, chloro or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

P is C—R 1 or N;

Q is C—R 2 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 or N;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, arylthio, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, halo-C 1 -C 6 -alkylcarbonyl, and

a is 1.

7. The compound of claim 1 , wherein:

R 8 , R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, chloro or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

P is N;

Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halogen, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy, and halo-C 1 -C 6 -alkoxy, and

a is 1.

8. The compound of claim 1 , wherein:

R 8 , R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, chloro or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

P is N;

Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

9. The compound of claim 1 , wherein:

R 1 , R 8 , R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, chloro, triifluoromethyl or methylamino;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

P is C—R 1 or N;

V is C—R 8 or N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 or N;

Z is C(O);

a is 1.

10. The compound of claim 1 , wherein:

R 9 , R 10 and R 11 , independently of one another, are hydrogen, cyano, chloro, bromo, methyl or trifluoromethyl;

R 3 , R 4 and R 6 are H;

R 2 is H, chloro, bromo or C 1 -C 6 -alkoxy;

R 5 is methyl;

P is N;

Q is C—R 2 ;

V is N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

11. The compound of claim 1 , wherein:

R 8 , R 9 , R 10 and R 11 , independently of one another, are hydrogen, chloro, bromo, methyl or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 2 is H, chloro, bromo or C 1 -C 6 -alkoxy;

R 5 is methyl;

P is N;

Q is C—R 2 ;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

12. The compound of claim 1 , wherein:

R 9 , R 10 and R 11 , independently of one another, is hydrogen, cyano, chloro, bromo, methyl or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 5 is methyl;

P is N;

Q is N;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

13. The compound of claim 1 , wherein:

R 9 , R 10 and R 11 , independently of one another, are hydrogen, chloro, bromo or methyl;

R 3 , R 4 and R 6 are H;

R 2 is H, chloro, bromo or methoxy;

R 5 is methyl;

P is N;

Q is C—R 2 ;

V is N;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

14. The compound of claim 1 , wherein:

R 8 , R 9 , R 10 and R 11 , independently of one another, are hydrogen, chloro, bromo, methyl or trifluoromethyl;

R 3 , R 4 and R 6 is H;

R 2 is H, chloro, bromo, methoxy, ethoxy, propoxy or butoxy;

R 5 is methyl;

P is N;

Q is C—R 2 ;

V is C—R 8 ;

W is C—R 9 ;

X is C—R 10 ;

Y is C—R 11 ;

Z is C(O);

R 7 is a substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of halo-C 1 -C 6 -alkylthio and halo-C 1 -C 6 -alkoxy, and

a is 1.

15. A method of producing the compounds of claim 1 ,

wherein the compound of formula (I) are produced by a process which comprises:

reacting a compound of formula (II)

with ammonium sulfide or sodium hydrosulfide wherein R 3 , R 4 , R 5 , R 6 , R 7 , P, Q, V, W, X, Y, Z, a, are as defined above for the compounds of formula (I)

in a solvent with or without the presence of base.

16. A method of treating an animal against endoparasitic infection, wherein the endoparasitic infection is a helminth, by administering an endoparasiticidally effective amount of the compound of claim 1 to an animal in need thereof.

17. The method of claim 16 , wherein the helminth is Haemonchus contortus.

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2016

From: MERIAL LIMITED

To: MERIAL, INC.

Reel/Frame 039037/0167 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2011

From: LE HIR DE FALLOIS, LOIC PATRICK; LEE, HYOUNG IK; TIMMONS, PHILIP REID

To: MERIAL LIMITED

Reel/Frame 026658/0449 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2010

From: LE HIR DE FALLOIS, LOIC PATRICK; LEE, HYOUNG IK; TIMMONS, PHILIP REID

To: MERIAL LIMITED

Reel/Frame 023910/0374 →

Continuity (2)

Provisional Application 61107114 · Oct 21, 2008

Related Publication 20100130565A1 · May 27, 2010