IP Library › Granted Patent US 8,309,557

Granted Patent B2

US 8,309,557 · App. 12/724,706 · Granted Nov 13, 2012

Pyrimidin-4-ylpropanedinitrile derivatives, processes for their preparation and their use as herbicides and plant growth regulators

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Quick Facts

Patent No.: US 8,309,557
App. No.: 12/724,706
Granted: Nov 13, 2012
Kind: B2

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Abstract

The invention relates to compounds of the formula (I) and N-oxides, tautomers and agrochemically compatible salts thereof to processes for their preparation, and to their use as herbicides and plant growth regulators, in particular as herbicides for the selected control of harmful plants in useful plant crops.

Claims (100)

1. A compound of formula (I) or an N-oxide or an agrochemically suitable salt thereof,

in which the radicals have the following meaning:

R 1 is phenyl, optionally substituted with 1-3 radicals R x , which, independently of one another, are halogen, carboxyl, cyano, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 4 )hydroxyalkyl, (C 2 -C 4 )alkoxyalkyl, (C 2 -C 4 )haloalkoxyalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 4 )haloalkynyl, hydroxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )haloalkenyloxy, (C 2 -C 4 )alkynyloxy, (C 3 -C 4 )haloalkynyloxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 2 -C 4 )alkenylthio, (C 2 -C 4 )haloalkenylthio, (C 2 -C 4 )alkenylsulfinyl, (C 2 -C 4 )haloalkenylsulfinyl, (C 2 -C 4 )alkenylsulfonyl, (C 2 -C 4 )haloalkenylsulfonyl, (C 2 -C 4 )alkynylthio, (C 3 -C 4 )haloalkynylthio, (C 3 -C 4 )alkynylsulfinyl, (C 3 -C 4 )haloalkynylsulfinyl, (C 3 -C 4 )alkynylsulfonyl, (C 3 -C 4 )haloalkynylsulfonyl, (C 1 -C 6 )alkylamino, (C 2 -C 8 )dialkylamino, (C 2 -C 6 )alkylcarbonyl, (C 2 -C 6 )alkoxycarbonyl, (C 2 -C 6 )alkylaminocarbonyl, (C 3 -C 8 )dialkylaminocarbonyl, (C 3 -C 6 )trialkylsilyl, phenyl, phenoxy or a 5- or 6-membered heteroaromatic ring, each phenyl ring, phenoxy ring or 5- or 6-membered heteroaromatic ring optionally substituted with 1-3 substituents independently of one another selected from R 28 ; or two adjacent radicals R x together form a group —OCH 2 O—, —CH 2 CH 2 O—, —OCH 2 CH 2 O—, —OCH(CH 3 )O—, —OC(CH 3 ) 2 O—, —OCF 2 O—, —CF 2 CF 2 O—, —OCF 2 CF 2 O— or —CH═CH—CH═CH—; or

(C 1 -C 6 )-alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 1 -C 3 )alkoxy, (C 1 -C 2 )haloalkoxy, (C 1 -C 3 )alkylthio, (C 1 -C 2 )haloalkylthio or optionally substituted aryl; or

(C 2 -C 6 )-alkenyl, optionally substituted with 1-3 radicals R z , which, independently of one another, are halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 3 )alkoxy, (C 1 -C 2 )haloalkoxy, (C 1 -C 3 )alkylthio or (C 1 -C 2 )haloalkylthio;

R 2 is H, F, Cl, Br, I, CN, NO 2 , OR 5 , SR 6 or N(R 7 )R 8 ; in which R 5 is H, (C 1 -C 4 )alkyl or (C 1 -C 3 )haloalkyl, R 6 is H, (C 1 -C 4 )alkyl or (C 1 -C 3 )haloalkyl and R 7 and R 8 , independently of one another, are H or (C 1 -C 4 )alkyl;

R 3 is H, (C 1 -C 4 )alkyl optionally substituted with 1-2 radicals R 9 , (C 2 -C 4 )alkenyl optionally substituted with 1-2 radicals R 10 , or (C 2 -C 4 )alkynyl optionally substituted with 1-2 radicals R 11 ; or R 3 is C(═O)R 12 , NO 2 , OR 13 , S(O) 2 R 14 , N(R 15 )R 16 or N═C(R 17 )R 18 ;

R 4 is H, (C 1 -C 4 )alkyl optionally substituted with 1-2 radicals R 9 , or C(═O)R 12 ; or

R 3 and R 4 together form a group —(CH 2 ) 4 —, —(CH 2 ) 5 —, —CH 2 CH═CHCH 2 — or —(CH 2 ) 2 O(CH 2 ) 2 —, each group optionally substituted with 1-2 radicals R 19 ; or

R 3 and R 4 together form a group ═(R 20 )N(R 21 )R 22 or ═C(R 23 )OR 24 ;

here, each radical R 9 , R 10 and R 11 , independently of the others, is halogen, (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, (C 1 -C 3 )alkylthio, (C 1 -C 3 )haloalkylthio, amino, (C 1 -C 3 )alkylamino, (C 2 -C 4 )dialkylamino or (C 2 -C 4 )alkoxycarbonyl;

R 12 is in each case independently of the others H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy;

R 13 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl or CHR 25 C(O)OR 26 ;

R 14 is (C 1 -C 4 )alkyl or (C 1 -C 3 )haloalkyl;

R 15 is H, (C 1 -C 4 )alkyl or C(═O)R 27 ;

R 16 is H or (C 1 -C 4 )alkyl;

R 17 is H, (C 1 -C 4 )alkyl or phenyl optionally substituted with 1-3 radicals, which, independently of one another, are CH 3 , Cl or OCH 3 ;

R 18 is H or (C 1 -C 4 )alkyl; or R 17 and R 18 together form a group —(CH 2 ) 4 — or —(CH 2 ) 5 —;

R 19 is, in each case independently of the others, halogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, (C 1 -C 3 )alkylthio, (C 1 -C 3 )haloalkylthio, amino, (C 1 -C 3 )alkylamino, (C 2 -C 4 )dialkylamino or (C 2 -C 4 )alkoxycarbonyl;

R 20 is H or (C 1 -C 4 )alkyl;

R 21 and R 22 , independently of one another, are H or (C 1 -C 4 )alkyl; or R 21 and R 22 together form a group —(CH 2 ) 4 —, —(CH 2 ) 5 —, —CH 2 CH═CHCH 2 — or —(CH 2 ) 2 O(CH 2 ) 2 —;

R 23 is H or (C 1 -C 4 )alkyl;

R 24 is (C 1 -C 4 )alkyl;

R 25 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy;

R 26 is H, (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy;

R 27 is H, (C 1 -C 4 )alkyl or benzyl; and

R 28 is, in each case independently of the others, halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 4 )alkynyl, (C 3 -C 4 )haloalkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )alkylamino, (C 2 -C 8 )dialkylamino, (C 2 -C 4 )alkylcarbonyl, (C 2 -C 6 )alkoxycarbonyl, (C 2 -C 6 )alkylaminocarbonyl, (C 3 -C 8 )dialkylaminocarbonyl or (C 3 -C 6 )trialkylsilyl.

2. A compound of the formula (I), or N-oxide or agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning.

R 1 is phenyl, optionally substituted with 1-3 radicals R x , which, independently of one another, are halogen, carboxyl, cyano, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 2 -C 4 )alkoxyalkyl, (C 2 -C 4 )haloalkoxyalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 4 )haloalkynyl, hydroxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 6 )alkylamino, (C 2 -C 8 )dialkylamino, —OCH 2 O—, —CH 2 CH 2 O—, —OCH 2 CH 2 O—, —OCH(CH 3 )O—, —OC(CH 3 ) 2 O—, —OCF 2 O—, —CF 2 CF 2 O— or —OCF 2 CF 2 O—, where the eight last-mentioned substituents are formed in each case by two adjacent R x ; or

(C 1 -C 6 )alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 1 -C 3 )alkoxy, (C 1 -C 2 )haloalkoxy, (C 1 -C 3 )alkylthio, (C 1 -C 2 )haloalkylthio or optionally substituted phenyl; or

(C 2 -C 6 )alkenyl, optionally substituted with 1-3 radicals R z , which, independently of one another, are halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 3 )alkoxy, (C 1 -C 2 )haloalkoxy, (C 1 -C 3 )alkylthio or (C 1 -C 2 )haloalkylthio;

R 2 is H, F, Cl, Br, I, CN or NO 2 ;

R 3 is H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, C(═O)R 12 , OR 13 , N(R 15 )R 16 or N═C(R 17 )R 18 ;

R 4 is H or (C 1 -C 4 )alkyl, optionally substituted with 1-2 radicals R 9 , or C(═O)R 12 ; or

R 3 and R 4 together form a group —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 2 O(CH 2 ) 2 — or ═C(R 20 )N(R 21 )R 22 ;

R 12 is, in each case independently of the others, H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy;

R 13 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl or CHR 25 C(O)OR 26 ;

R 15 is H, (C 1 -C 4 )alkyl or C(═O)R 27 ;

R 16 is H or (C 1 -C 4 )alkyl;

R 17 is H, (C 1 -C 4 )alkyl or phenyl optionally substituted with 1-3 radicals which, independently of one another, are CH 3 , Cl or OCH 3 ;

R 18 is H or (C 1 -C 4 )alkyl; or R 17 and R 18 together form a group —(CH 2 ) 4 — or —(CH 2 ) 5 —;

R 20 is H or (C 1 -C 4 )alkyl;

R 25 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy; and

R 26 is H, (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy.

3. A compound of formula (I) or N-oxide or agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning:

—OCH 2 O—, —OCH 2 CH 2 O— or —OCH(CH 3 )O—, where the three last-mentioned substituents are in each case formed by two adjacent R x ; or

(C 1 -C 6 )alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, (C 1 -C 3 )alkoxy, (C 1 -C 2 )haloalkoxy or unsubstituted phenyl or phenyl substituted by one or more halogens; or

(C 2 -C 6 )alkenyl, optionally substituted with 1-3 radicals R z , which, independently of one another, are halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 3 )alkoxy or (C 1 -C 2 )haloalkoxy;

R 2 is F, Cl, Br, I or NO 2 ;

R 3 is H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, C(═O)R 12 , in which R 12 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy,

or OR 13 , in which R 13 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl or CHR 25 C(O)OR 26 , in which R 25 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy, and R 26 is H, (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy;

R 4 is H or (C 1 -C 4 )alkyl; or

R 3 and R 4 together form a group —(CH 2 ) 2 O(CH 2 ) 2 —.

4. A compound of formula (I) or N-oxide or agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning:

R 1 is phenyl, optionally substituted with 1-3 radicals R x , which, independently of one another, are halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 6 )alkylamino, (C 2 -C 8 )dialkylamino, —OCH 2 O—, —OCH 2 CH 2 O— or —OCH(CH 3 )O—; or

(C 1 -C 6 )alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, (C 1 -C 3 )alkoxy or (C 1 -C 2 )haloalkoxy; or

R 2 is F, Cl, Br or I;

R 3 is H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, C(═O)R 12 , in which R 12 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy, or OR 13 , in which R 13 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl or CHR 25 C(O)OR 26 , in which R 25 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, phenyl, phenoxy or benzyloxy, and R 26 is H, (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy;

R 4 is H or (C 1 -C 4 )alkyl; or

R 3 and R 4 together form a group —(CH 2 ) 2 O(CH 2 ) 2 —.

5. An agrochemical composition comprising a) at least one compound of formula (I) or N-oxide or agrochemically suitable salt thereof, as defined in claim 1 , and b) at least one auxiliary or additive customary in crop protection.

6. An agrochemical composition comprising a) at least one compound of formula (I) or N-oxide or agrochemically suitable salt thereof, as defined in claim 1 , b) at least one agrochemical active ingredient different from component a), and optionally c) at least one auxiliary or additive customary in crop protection.

7. A method for controlling an undesired plant or for regulating the growth of a plant, comprising applying an effective amount of at least one compound of formula (I) or an N-oxide or an agrochemically suitable salt thereof, as defined in claim 1 , to the plant, or to a seed material or to an area on which the plant grows.

8. A herbicide or plant growth regulator composition comprising at least one compound of the formulation (I) or an N-oxide or an agrochemically suitable salt as claimed in claim 1 .

9. A herbicide or plant growth regulator composition as claimed in claim 8 , where the compounds of the formula (I) or N-oxide or agrochemically suitable salt thereof is suitable for controlling harmful plants or for growth regulation in plant crops.

10. A herbicide or plant growth regulator as claimed in claim 9 , where the crop plants are transgenic or nontransgenic crop plants.

11. A process for the preparation of a compound of formula (I) or N-oxide or agrochemically suitable salt thereof, as defined in claim 1 comprising:

a) reacting a halogen compound of the formula (II)

with an amine of the formula (III) HNR 3 R 4 , where Hal is a halogen atom, and

b) optionally converting the compound of the formula (I) in step a) into an N-oxide or an agrochemically suitable salt.

12. A compound of the formula (II)

in which Hal is a halogen atom and

and

13. A compound of formula (I) or an N-oxide or an agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning.

R 1 is 2-F-4-Cl-Phenyl,

R 2 is Cl,

R 3 is H, and

R 4 is H.

14. A compound of formula (I) or N-oxide or agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning:

(C 1 -C 6 )alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, (C 1 -C 3 )alkoxy or (C 1 -C 2 )haloalkoxy or unsubstituted phenyl or phenyl substituted by a halogen; or

R 2 is F, Cl, Br, I, or NO 2 ;

R 3 is H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, C(═O)R 12 , in which R 12 is H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, (C 1 -C 4 )alkoxy, or OR 13 , in which R 13 is H, (C 1 -C 4 )alkyl or (C 1 -C 3 )haloalkyl; and

R 4 is H or (C 1 -C 4 )alkyl.

15. A compound of formula (I) or N-oxide or agrochemically suitable salt thereof as claimed in claim 1 , in which the radicals have the following meaning:

R 1 is phenyl, optionally substituted with 1-3 radicals R x , which, independently of one another, are halogen, carboxyl, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 4 )alkoxy; or

(C 1 -C 6 )alkyl, optionally substituted with 1-3 radicals R y , which, independently of one another, are halogen, phenyl or 4-halophenyl;

R 2 is F, Cl, Br, or NO 2 ;

R 3 is H or (C 1 -C 4 )alkyl; and

R 4 is H or (C 1 -C 4 )alkyl.

Assignments (3)

CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 034892 FRAME: 0286. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 19, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035071/0680 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 034892/0286 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 28, 2010

From: BRUENJES, MARCO; DIETRICH, HANSJOERG; AHRENS, HARTMUT; HOFFMANN, MICHAEL GERHARD; DITTGEN, JAN; FEUCHT, DIETER; ROSINGER, CHRISTOPHER HUGH; HAEUSER-HAHN, ISOLDE

To: BAYER CROPSCIENCE AG

Reel/Frame 024458/0276 →