IP Library › Granted Patent US 8,486,934

Granted Patent B2

US 8,486,934 · App. 13/292,517 · Granted Jul 16, 2013

Oxadiazine-substituted arylamides

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Patent No.: US 8,486,934
App. No.: 13/292,517
Granted: Jul 16, 2013
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 (130)

1. A compound of formula (I)

wherein

A 1 is oxygen or sulphur,

A 2 is amino, aminoformyl or aminoacetyl,

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 -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

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,

or a N-oxide or salt thereof.

2. The compound of claim 1 , where

A 1 is oxygen or sulphur,

A 2 is amino,

R 1 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano(C 1 -C 6 -alkyl), C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 4 -alkyl or C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkyl,

R 2 independently of one another is C 1 -C 4 -alkyl 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 -haloalkoxy, C 1 C 4 alkylthio, C 1 C 4 alkylsulphinyl and C 1 -C 4 -alkylsulphonyl,

n is 0 or 1,

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 -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,

R 5 is a 5-membered heterocyclic ring R 5 -1 or R 5 -2,

R 6 is 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 or

where m =0 to 3,

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 -haloalkylsulphonyl or (C 1 -C 4 -alkyl)-C 1 -C 4 -alkoxyimino,

R 8 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,

R 9 is hydrogen, C 1 -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,

Q 1 is O, S, N, NR 6 , NR 7 or NR 8 ,

W 1 , Y 1 , Z 1 independently of one another are N, CR 6 , CR 7 or CR 8 ,

X 1 is N, CH, CF, CCl, CBr or CI, and

X 2 is N or CR 9 ,

or a N-oxide or salt thereof.

3. The compound of claim 2 , where

m is 0 or 1.

4. The compound of claim 2 , where

m is 0.

5. The compound of claim 1 , where

A 1 is oxygen,

R 1 is hydrogen, methyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthio methyl, methylsulphinyl methyl or methylsulphonyl methyl,

R 2 independently of one another is C 1 -C 4 -alkyl, 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,-C 4 -alkoxy and C 1 -C 4 -haloalkoxy,

n is 0,

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

R 5 is a pyrazole or pyrrole ring of the group R 5 -3 to R 5 -8, where each R 5 is substituted by R 6 and is optionally substituted by R 7 or R 8 or both R 7 and R 8 ,

R 6 is

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

R 8 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl.

6. A compound of formula (II)

where

A 2 is amino, aminoformyl or aminoacetyl,

n is 0 to 4,

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,

or a N-oxide or salt thereof.

7. A compound of formula (VII)

where

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 -alkyl-sulphinyl, 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,

or a N-oxide or salt thereof.

8. An agrochemical composition comprising at least one compound of claim 1 and extenders or surfactants, or both.

9. A method for applying compounds of claim 1 to act on insects, arachnids, helminths, nematodes and molluscs, or their habitat, or both.

10. A method of preparing an agrochemical composition, comprising mixing a compound of claim 1 with extenders or surfactants, or both.

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

12. A method for treating transgenic plants as obtained by genetic engineering methods, comprising contacting said transgenic plants with a compound of claim 1 .

13. A method for treating seed of transgenic plants as obtained by genetic engineering methods, comprising contacting said seed of said transgenic plants with a compound of claim 1 .

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

15. A method of preparing a compound of claim 1 , where

A 1 is oxygen,

comprising reacting a compound of formula (II)

where

A 2 is amino, aminoformyl or aminoacetyl,

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 -alkyl-sulphinyl, 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 4 -haloalkyl)(C 1 -C 4r alkoxy)imino or C 3 -C 6 -trialkylsilyl, and

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,

with an acid chloride of formula (III)

where

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 -alkyl sulphonyl, 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.

16. A method of preparing a compound of claim 1 , where

A 1 is sulphur,

comprising reacting a compound of formula (I-a)

where

A 2 is amino, aminoformyl or aminoacetyl,

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 -alkyl-sulphinyl, 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 -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,

with a sulphurizing agent.

17. A method of preparing a compound of claim 6 ,

where

R 1 is not hydrogen,

comprising reacting a compound of formula (II)

where

A 2 is amino, aminoformyl or aminoacetyl,

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 -alkyl-sulphinyl, 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 -cycloalkyl amino, (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, 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.

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

where

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 -alkyl-sulphinyl, 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,

comprising reacting a compound of claim 8 with a reducing agent in the presence of a diluent.

19. A method of preparing a compound of claim 7 , comprising reacting a compound of formula (VIII)

where

R 2 independently of one another is C 1 -C 6 -alkyl, C 1 -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 -alkythio, C 1 -C 4 -alkyl-sulphinyl, 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 -haloalkylsulphony, 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,

Z is chlorine, bromine, iodine, methylsulphonyl or tolylsulphonyl, or a N-oxide or salt thereof,

with a base in the presence of a solvent.

20. A method of preparing a compound of claim 18

where

R 3 is 4-chloro, 4-bromo or 4-iodo,

comprising reacting a compound of formula (II-b′)

where

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 -alkyl-sulphinyl, 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, and

with a halogenating agent in the presence of a diluent.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035005/0367 →