IP Library › Granted Patent US 8,822,689
Granted Patent B2
US 8,822,689 · App. 13/622,664 · Granted Sep 2, 2014

Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof

Inventors: Loic Patrick Le Hir de Fallois (Chapel Hill, NC); Scot Kevin Huber (Raleigh, NC); Hyoung Ik Lee (Cary, NC); Robert Toms Jacobs (Wake Forest, NC)
Assignees: Merial Limited; Aventis Agriculture
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Quick Facts
Patent No.
US 8,822,689
App. No.
13/622,664
Granted
Sep 2, 2014
Kind
B2
Abstract

The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I): wherein R 3 , R 4 , R 5 , R 6 , R 7 , P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.

Claims (114)

1. An aryloazol-2-yl-cyanoethylamine compound of the formula (I):

P is N;

Q is C—R 2 or N;

V is C—R 8 ;

W is N, X is C—R 10 or N and Y is C—R 11 ; or W is N, X is C—R 10 and Y is C—R 11 or N; or

X is N, W is C—R 9 or N and Y is C—R 11 ; or X is N, W is C—R 9 and Y is C—R 11 or N; or

Y is N, W is C—R 9 or N and X is C—R 10 ; or Y is N, W is C—R 9 and X is C—R 10 or N;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO 2 C—, alkyl-O 2 C—, 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, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl;

R 3 , R 4 and R 5 each, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl; unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl; or unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino; or

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

R 6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino and di(alkyl)amino;

R 7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or 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, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino and di(alkyl)amino; unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino;

or

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, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino and di(alkyl)amino;

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

a is 1, 2 or 3;

p is 0, 1 or 2; or

salts thereof.

2. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, hydroxy-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, phenoxy, C 1 -C 6 -alkoxy-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, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, formyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C—, 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 and halo-C 1 -C 6 -alkylsulfonyl;

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

R 4 and R 5 together with the carbon to which they are attached form a cycloalkyl ring;

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 unsubstituted or substituted benzyl, 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, 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 or 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, phenyl, phenoxy, 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 C 1 -C 6 -alkylamino and di(C 1 -C 6 -alkyl)amino; unsubstituted or substituted hetaryl, 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;

or

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 ;

a is 1, 2 or 3; and

p is 0, 1 or 2.

3. The aryloazol-2-yl-cyanoethylamine of claim 2 , wherein

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, hydroxy-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, phenoxy, C 1 -C 6 -alkoxy-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, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, formyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C—, 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 and halo-C 1 -C 6 -alkylsulfonyl;

R 3 , R 4 and R 6 are H;

R 5 is methyl;

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, C 1 -C 6 -alkylamino and di(C 1 -C 6 -alkyl)amino; unsubstituted or substituted hetaryl, 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 C(O); and

a is 1.

4. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

R 3 , R 4 and R 6 are hydrogen;

R 5 is hydrogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy-C 1 -C 6 -alkyl, or C 1 -C 6 -alkylsulfonyloxy-C 1 -C 6 -alkyl;

R 7 is unsubstituted phenyl or phenyl substituted by one or more substituents selected from the group consisting of C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, phenyl, phenyloxy, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylthio, halo-C 1 -C 6 -alkylsulfinyl and halo-C 1 -C 6 -alkylsulfonyl;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, cyano, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylamino, hydroxy-C 1 -C 6 -alkyl, formyl, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, HO 2 C—, C 1 -C 6 -alkyl-O 2 C— or unsubstituted or substituted phenyl wherein the substituents are C 1 -C 6 -alkyl or halo-C 1 -C 6 -alkyl;

Z is C(O); and

a is 1.

5. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl, ethyl, butyl, CH 2 OH, CH 2 OCH 3 , CH 2 SCH 3 or CH 2 OSO 2 CH 3 ;

R 7 is a phenyl substituted with butyl, CF 3 , phenyl, phenoxy, OCF 3 , SCF 3 , SOCF 3 or SO 2 CF 3 ;

R 2 , R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, methyl, CH 2 NH 2 , CH 2 N(CH 3 ) 2 , vinyl, CH 2 OH, CH(OH)CH 2 OH, CO 2 H, CO 2 CH 3 , Ph-CF 3 , F, Cl, Br, CF 3 , OCF 3 or CN;

Z is C(O); and

a is 1.

6. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

R 2 is hydrogen, Cl, methyl, methoxy, ethoxy, propoxy, butoxy, O(CH 2 ) 2 OCH 3 , or O(CH 2 ) 2 N(CH 3 ) 2 ;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 , phenoxy or SCF 3 ;

R 8 , R 9 and R 10 each, independently of one another, is hydrogen, Cl, Br, C 1 -C 6 -alkyl, CF 3 , nitro, amino, amido, CO 2 CH 3 or NHCOCH 3 ;

Z is C(O); and

a is 1.

7. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

R 2 is hydrogen, Cl, Br or methoxy;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 or SCF 3 ;

R 8 , R 9 , R 10 and R 11 each, independently of one another, is hydrogen, Cl, Br or methyl;

Z is C(O); and

a is 1.

8. A pesticidal composition comprising a compound of claim 1 and a pesticidally or veterinarily acceptable carrier.

9. The pesticidal composition of claim 8 which further comprises an additional pesticidal compound.

10. The aryloazol-2-yl-cyanoethylamine of claim 4 , wherein

W is C—R 9 ;

X is C—R 10 ;

Y is N;

R 2 is hydrogen, Cl, Br or methoxy;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 or SCF 3 ;

R 8 , R 9 and R 10 are independently hydrogen, Cl, Br or methyl;

Z is C(O); and

a is 1.

11. The aryloazol-2-yl-cyanoethylamine of claim 1 , wherein

V is C—R 8 ;

W is N;

X is C—R 10 ;

Y is C—R 11 ;

R 2 is hydrogen, Cl, Br or methoxy;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 or SCF 3 ;

R 8 , R 10 and R 11 are independently hydrogen, Cl, Br or methyl;

Z is C(O); and

a is 1.

12. The aryloazol-2-yl-cyanoethylamine of claim 4 , wherein

W is C—R 9 ;

X is N;

Y is C—R 11 ;

R 2 is hydrogen, Cl, Br or methoxy;

R 3 , R 4 and R 6 are hydrogen;

R 5 is methyl;

R 7 is phenyl substituted by OCF 3 or SCF 3 ;

R 8 , R 9 and R 10 are independently hydrogen, Cl, Br or methyl;

Z is C(O); and

a is 1.

13. The aryloazol-2-yl-cyanoethylamine of claim 3 , wherein

W is N;

X is C—R 10 ; and

Y is C—R 11 .

14. The aryloazol-2-yl-cyanoethylamine of claim 3 , wherein

W is C—R 9 ;

X is N; and

Y is C—R 11 .

15. The aryloazol-2-yl-cyanoethylamine of claim 3 , wherein

W is C—R 9 ;

X is C—R 10 ; and

Y is N.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2015
From: MERIAL LIMITED
To: MERIAL, INC.
Reel/Frame 035576/0042 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2013
From: SOLL, MARK DAVID; LE HIR DE FALLOIS, LOIC PATRICK; HUBER, SCOT KEVIN; LEE, HYOUNG IK; WILKINSON, DOUGLAS EDWARD; JACOBS, ROBERT TOMS
To: MERIAL LIMITED; AVENTIS AGRICULTURE
Reel/Frame 030143/0457 →
Continuity (1)
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