IP Library › Granted Patent US 8,017,558

Granted Patent B2

US 8,017,558 · App. 12/097,457 · Granted Sep 13, 2011

Carboxamides for controlling micro-organisms in plant and material protection

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Quick Facts

Patent No.: US 8,017,558
App. No.: 12/097,457
Granted: Sep 13, 2011
Kind: B2

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Abstract

Novel carboxamides of the formula (I) The present application is further directed toward a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

Claims (134)

1. A compound of formula (I)

in which

X represents OR 1 , SR 2 , NHR 3 , NR 4 R 5 , SOR 6 , SO 2 R 6 ,

R 1 represents C 1 -C 12 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -haloalkyl, hydroxy-C 1 -C 8 -alkyl, (C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, bis(C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, (C 1 -C 4 -alkoxy)carbonyl-(C 1 -C 4 -alkyl); in each case optionally halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted phenyl-(C 1 -C 2 -alkyl) or hetaryl-(C 1 -C 2 -alkyl); in each case optionally C 1 -C 4 -alkoxy-, halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted (C 1 -C 6 -alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl, phenylcarbonyl or hetarylcarbonyl,

R 2 represents C 1 -C 12 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -haloalkyl, hydroxy-C 1 -C 8 -alkyl, (C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, bis(C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, cyano-(C 1 -C 4 -alkyl), —CH 2 S—CN, (C 1 -C 4 -alkoxy)carbonyl-(C 1 -C 4 -alkyl); in each case optionally halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted phenyl-(C 1 -C 2 -alkyl) or hetaryl-(C 1 -C 2 -alkyl); in each case optionally C 1 -C 4 -alkoxy-, halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted (C 1 -C 6 -alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl, phenylcarbonyl or hetarylcarbonyl,

R 3 , R 4 and R 5 independently of one another represent amino, hydroxyl, cyano, C 1 -C u -alkyl, C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, hydroxy-C 1 -C 8 -alkyl, (C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, bis(C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, cyano-(C 1 -C 4 -alkyl), phenoxy, phenylamino, benzyloxy or benzylamino,

R 6 represents C 1 -C 12 -alkyl or C 1 -C 8 -haloalkyl,

M represents a phenyl which is monosubstituted by R 7 ,

R 7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,

Q represents a direct bond, C 1 -C 4 -alkylene, C 2 -C 4 -alkenylene, O, S, SO, SO 2 or NR 9 ,

R 9 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl or C 3 -C 6 -cycloalkyl,

Z represents Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z 6 ,

Z 1 represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents,

Z 2 represents pyridinyl which is optionally mono- to trisubstituted by identical or different substituents,

Z 3 represents cycloalkyl or bicycloalkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, alkyl and/or —(CR 10 R 11 ) m SiR 12 R 13 R 14 substituents,

Z 4 represents unsubstituted C 2 -C 20 -alkyl or represents C 1 -C 20 -alkyl which is mono- or polysubstituted by identical or different halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkyl-sulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 12 R 13 R 14 and/or C 3 -C 6 -cycloalkyl substituents, where the cycloalkyl moiety for its part may optionally be mono- or polysubstituted by identical or different halogen and/or C 1 -C 4 -alkyl substituents,

Z 5 represents C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl, each of which is optionally mono- or polysubstituted by identical or different halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 12 R 13 R 14 and/or C 3 -C 6 -cycloalkyl substituents, where the cycloalkyl moiety for its part may optionally be mono- or polysubstituted by identical or different halogen and/or C 1 -C 4 -alkyl substituents,

Z 6 represents an optionally mono- or polysubstituted saturated or unsaturated 3- to 7-membered ring which contains a silicon atom as ring member, in which case Q represents a direct bond or C 1 -C 4 -alkylene,

R 10 represents hydrogen or C 1 -C 4 -alkyl,

R 11 represents hydrogen or C 1 -C 4 -alkyl,

m represents 0, 1, 2 or 3,

R 12 and R 13 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl,

R 14 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl,

A represents one of the radicals selected from the group consisting of A1, A2, A3, A9, A11, A12, A13, A14, A15, A18, and A19

R 15 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -halo-alkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or amino-carbonyl-C 1 -C 4 -alkyl,

R 16 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,

R 17 represents hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl having in each case 1 to 5 halogen atoms, or phenyl,

R 18 and R 19 independently of one another, represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 20 represents halogen, cyano or C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,

R 21 and R 22 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 23 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 31 and R 32 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 33 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 37 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 38 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 39 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 40 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 41 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 42 represents hydrogen or C 1 -C 4 -alkyl,

R 43 represents halogen or C 1 -C 4 -alkyl,

R 44 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 47 represents hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphonyl, di(C 1 -C 4 -alkyl)aminosulphonyl, C 1 -C 6 -alkylcarbonyl or in each case optionally substituted phenylsulphonyl or benzoyl,

R 48 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 49 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 50 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 51 represents C 1 -C 4 -alkyl.

2. A process for preparing a compound according to claim 1 , comprising

(a) if X represents OR 1 , reacting a compound of formula (II-a)

if appropriate, in the presence of a base, with an alkylating agent of the formula (III-a)

LG 1 -R 1 (III-a)

in which

LG 1 represents a leaving group

or with a Meerwein salt of the formula (III-d)

(R 1 ) 3 O + E − (III-d)

in which

E represents BF 4 , SbF 6 or SbCl 6 ,

to give a compound of formula (I-a)

(b) if X represents SR 2 , SOR 6 or SO 2 R 6 , in a first step reacting the compound of formula (II-a)

if appropriate in the presence of a diluent, with a thionating agent,

thus giving a compound of formula (II-b)

and, in a second step, if appropriate in the presence of a base, reacting with an alkylating agent of the formula (III-b) or the formula (III-c)

LG 2 -R 2 (III-b)

LG 6 -R 6 (III-c)

in which

LG 2 represents a leaving group,

LG 6 represents a leaving group,

to give a compound of formula (I-b) or the formula (I-c)

and, in a third step, reacting the compound of formula (I-c) with an oxidizing agent, if appropriate in the presence of a diluent, if appropriate in the presence of an acid binder and if appropriate in the presence of a catalyst, thus giving a compound of formula (I-d)

in which

n represents 1 or 2,

if appropriate in the presence of a base, with an amidating agent of formula (IV-a) or formula (IV-b)

in which

LG 3 represents a leaving group,

to give a compound of formula (I-e) or formula (I-f)

3. A compound of formula (I) according to claim 1 :

4. A composition for controlling unwanted microorganisms, comprising at least one compound according to claim 3 , and an extender and/or surfactant.

5. A compound according to claim 1 of the formulae (I-a), (I-b), (I-e), (I-f) or (I-d)

in which

n represents 1 or 2.

6. A composition for controlling unwanted microorganisms, comprising at least one-compound according to claim 1 , and an extender and/or surfactant.

7. A compound of the formula (I) according to claim 1 that is used for controlling unwanted microorganisms.

8. A method for controlling unwanted microorganisms, comprising applying a compound according to claim 1 to microorganisms and/or a habitat thereof.

9. A process for preparing a composition for controlling unwanted microorganisms, comprising mixing a compound according to claim 1 with an extender and/or surfactant.

10. A compound of the formula (I) according to claim 1 , wherein A represents one of the radicals selected from the group consisting of A1, A2, A3, A9, A11, A12, A13, A14, A15, and A18.

11. A composition for controlling unwanted microorganisms, comprising at least one compound of formula (I)

and an extender and/or surfactant,

wherein

X represents OR 1 , SR 2 , NHR 3 , NR 4 R 5 , SOR 6 , SO 2 R 6 ,

R 3 , R 4 and R 5 independently of one another represent amino, hydroxyl, cyano, C 1 -C 12 -alkyl, C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, hydroxy-C 1 -C 8 -alkyl, (C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, bis(C 1 -C 4 -alkoxy)-C 1 -C 8 -alkyl, cyano-(C 1 -C 4 -alkyl), phenoxy, phenylamino, benzyloxy or benzylamino,

R 6 represents C 1 -C 12 -alkyl or C 1 -C 8 -haloalkyl,

M represents a phenyl which is monosubstituted by R 7 ,

R 7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,

Q represents a direct bond, C 1 -C 4 -alkylene, C 2 -C 4 -alkenylene, 0, S, SO, SO 2 or NR 9 ,

Z represents Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z 6 ,

Z 1 represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents,

Z 2 represents pyridinyl which is optionally mono- to trisubstituted by identical or different substituents,

Z 3 represents cycloalkyl or bicycloalkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, alkyl and/or —(CR 10 R 11 ) m SiR 12 R 13 R 14 substituents,

R 10 represents hydrogen or C 1 -C 4 -alkyl,

R 11 represents hydrogen or C 1 -C 4 -alkyl,

m represents 0, 1, 2 or 3,

R 12 and R 13 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl,

A represents one of the radicals A1 to A19 below

R 16 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,

R 18 and R 19 independently of one another, represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 20 represents halogen, cyano or C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,

R 21 and R 22 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 23 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 31 and R 32 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 33 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 34 and R 35 independently of one another represent hydrogen, halogen, amino, nitro, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 36 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 37 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 38 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 39 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 40 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 41 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 42 represents hydrogen or C 1 -C 4 -alkyl,

R 43 represents halogen or C 1 -C 4 -alkyl,

R 44 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 48 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 49 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 50 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 51 represents C 1 -C 4 -alkyl.

Assignments (3)

CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED ON REEL 034891 FRAME 0140. ASSIGNOR(S) HEREBY CONFIRMS THE THE ASSIGNEE ADDRESS SHOULD BE ALFRED-NOBEL-STRASSE 10 MONHEIM AM RHEIN, GERMANY 40789. Recorded Feb 19, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035050/0156 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 034891/0128 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2009

From: DUNKEL, RALF, DR.; ELBE, HANS-LUDWIG, DR.; GREUL, JORG NICO, DR.; GAYER, HERBERT, DR.; KRUGER, BERND-WIELAND, DR.; VOERSTE, ARND, DR.; WACHENDORFF-NEUMANN, ULRIKE, DR.; DAHMEN, PETER, DR.

To: BAYER CROPSCIENCE AG

Reel/Frame 022175/0374 →