IP Library › Granted Patent US 8,062,995

Granted Patent B2

US 8,062,995 · App. 11/992,006 · Granted Nov 22, 2011

Dioxazine-substituted arylamides

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Patent No.: US 8,062,995
App. No.: 11/992,006
Granted: Nov 22, 2011
Kind: B2

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Abstract

Novel dioxazine- and oxdiazine-substituted arylamides of the formula (I) in which A 1 , A 2 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the description, a plurality of processes for preparing these compounds and their use for controlling pests, and also novel intermediates and processes for their preparation.

Claims (91)

1. A compound of formula (I-1):

wherein:

A 2 is oxygen,

R 3 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino or C 3 -C 6 -trialkylsilyl,

R 4 is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halogen, cyano, nitro or C 3 -C 6 -trialkylsilyl, and

X 1 is N, CH, CF, CC1, CBr or CI,

X 2 is N or CR 9 ,

X 3 is N or CH,

R 7 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalklsulphonyl or (C 1 -C 4 -alkyl)C 1 -C 4 -alkoxyimino, and

R 9 is hydrogen, C 3 -C 6 -alkyl, C 3 -C 6 -cycloalkyl C 1 -C 6 -haloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -haloalkylthio,

or a N-oxide or salt thereof.

2. The compound of claim 1 , wherein:

R 3 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -haloalkylthio,

R 4 is C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloakynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halogen, cyano, nitro or C 3 -C 6 -trialkylsilyl,

or a N-oxide or salt thereof.

3. The compound of claim 1 , wherein:

A l is oxygen,

R 3 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, halogen, cyano or C 1 -C 2 -haloalkoxy,

R 4 is C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro or C 3 -C 6 -trialkylsilyl,

X 1 is CCl and X 2 is CH, or

X 1 is CF and X 2 is CCl, or

X 1 is CCl and X 2 is CCl, or

X 1 is N and X 2 is CF, or

X 1 is N and X 2 is CCl, or

X 1 is N and X 2 is CBr, or

X 1 and X 2 are N, and

R 7 is hydrogen, halogen or C 1 -C 4 -haloalkyl.

4. A compound of formula (II)

wherein:

A 2 is oxygen

R 1 is hydrogen, amino, hydroxyl or C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 4 -alkoxy)carbonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino and (C 1 -C 4 -alkyl)-C 3 -C 6 -cycloalkylamino,

R 2 independently of one another is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently, of one another are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)carbonyl and C 3 -C 6 -trialkylsilyl,

n is 0 to 4,

R 3 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkcoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino or C 3 -C 6 -trialkylsilyl, and

or a N-oxide or salt thereof.

5. A pesticide composition comprising at least one compound of claim 1 and an auxiliary.

6. A method for treating animal pests, comprising contacting a compound of claim 1 with animal pests, their habitat, or both, wherein said animal pests are selected from the group consisting of insects, arachnids, helminths, nemaatodes, and molluscs, or a combination thereof.

7. A method of preparing a pesticide composition, said method comprising admixing a compound of claim 1 with extenders or surfactants, or both.

8. A method for treating seed, comprising contacting said seed with a compound of claim 1 .

9. A method for treating transgenic plants, comprising contacting said transgenic plants with a compound of claim 1 .

10. A method for treating seed of transgenic plants, comprising contacting said seed of transgenic plants with a compound of claim 1 .

11. A seed which has been treated with a compound of claim 1 .

12. A method of preparing a compound of formula (I),

wherein:

A l is oxygen,

comprising reacting a compound of formula (II)

wherein:

A 2 is oxygen,

R 2 independently of one another is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)carbonyl and C 3 -C 6 -trialkylsilyl,

n is 0 to 4,

with an acid chloride of formula (III)

wherein:

R 5 is a 5- or 6-membered heteroaromatic ring optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, CO 2 H, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 - alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, C 3 -C 6 -trialkylsilyl, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, or is selected from the group consisting of phenyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic rings and aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, where each of the aromatic, heteroaromatic or aromatic heterobicyclic systems is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, CO 2 H, CO 2 NH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, (C 1 -C 4 -alkyl)amino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl , di(C 2 -C 8 -alkyl)aminocarbonyl, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino and C 3 -C 6 -trialkylsilyl.

13. A method of preparing a compound of formula (I),

wherein:

A 1 is sulphur,

comprising reacting a compound of formula (I-a)

wherein:

A 2 is oxygen,

R 2 independently of one another is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)carbonyl and C 3 -C 6 -trialkylsilyl,

n is 0 to 4,

R 5 is a 5- or 6-membered heteroaromatic ring optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, CO 2 H, CONH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 1 -C 4 -alkyl)aminocarbonyl, C 3 -C 6 -trialkylsilyl, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, or is selected from the group consisting of phenyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic rings and aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, where each of the aromatic, heteroaromatic or aromatic heterobicyclic systems is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, CO 2 H, CO 2 NH 2 , NO 2 , OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, (C 1 -C 4 -alkyl)amino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)aminocarbonyl, di(C 2 -C 8 -alkyl)aminocarbonyl, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino and C 3 -C 6 -trialkylsilyl,

with a sulphurizing agent.

14. A method of preparing a compound of formula (II), wherein:

R 1 is not hydrogen,

comprising reacting a compound of formula (II)

wherein:

A 2 is oxygen,

R 1 is hydrogen,

R 2 independently of one another is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)carbonyl and C 3 -C 6 -trialkylsilyl,

n is 0 to 4,

R 3 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)amino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -alkoxy)imino or C 3 -C 6 -trialkylsilyl, and

(A) with an alkylating agent in the presence of a base in the presence of a diluent, or

(B) with an alkylating agent first in a condensation reaction in the presence of a diluent and second with a reducing agent in the presence of a diluent.

15. A method of preparing a compound of formula (II-a)

wherein:

R 2 independently of one another is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, each optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)carbonyl and C 3 -C 6 -trialkylsilyl,

n is 0 to 4,

R 3 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 - haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 1 -haloalkyl)(C 1 -C 4 -alkoxy)imino or C 3 -C 6 -trialkylsilyl, and

comprising reacting a compound having formula (IV):

with an activating agent, optionally in the presence of a diluent.

16. The compound of claim 1 , selected from the group consisting of:

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035005/0367 →