N-acetonyl-substituted-amides

• US 5,196,046 A
• Filed: 09/05/1989
• Issued: 03/23/1993
• Est. Priority Date: 07/26/1984
• Status: Expired due to Fees

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Rohm and Haas Company (Dow, Inc.)
• Inventors: Sharma, Ashok K.
• Primary Examiner(s): Cintins, Marianne M.
• Assistant Examiner(s): SCALZO, CATHERINE KILBY
• Application Number:
  US07/403,212
• Time in Patent Office: 1,295 Days
• Field of Search: 546/276, 546/278, 546/279, 546/300, 546/330, 546/336, 71/94
• US Class Current: 514/354
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/08 with oxygen as the ring hetero atom
• CPC Class Codes: A01N 43/10 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: C07D 207/325 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 213/82 in position 3
• CPC Class Codes: C07D 215/54 attached in position 3
• CPC Class Codes: C07D 217/26 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/56 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 239/28 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 261/18 Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
• CPC Class Codes: C07D 263/34 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 307/68 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 333/38 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Certain N-acetonyl-substituted-amides of the formula: ##STR1## wherein A is a pyridyl, group; X is halo, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, carbamoyl, dithiocarbamoyl, hydroxy, azido, trifluoromethylcarboxy, (C₁ -C₄)alkylcarbonyloxy, phenylcarbonyloxy, phenoxy, thiophenyl, imidazolyl or triazolyl; Y and Z are each independently a hydrogen, halo, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, carbamoyl, dithiocarbamoyl, hydroxy, azido, trifluoromethylcarboxy, (C₁ -C₄)alkylcarbonyloxy, phenylcarbonyloxy, phenoxy, thiophenyl, imidazolyl or triazolyl; R¹ and R² are each independently a hydrogen atom or a (C₁ -C₆)alkyl group; and compositions containing these amides are fungicidally active, particularly against phytophthogenic fungi.

Claims

1. A compound of the structure:

##STR18## wherein A is pyridyl which may be substituted with up to three substituents independently selected from halo, trifluoromethyl, fluorosulfonyl, methyl, ethyl, methoxy or phenyl;

X is chloro, bromo, iodo, fluoro, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, carbamoyl, thiocarbamoylthio, hydroxy, azido, (C₁ -C₄)alkylcarbonyloxy, phenylcarbonyloxy, trifluoromethylcarbonyloxy, phenoxy, phenylthio, imidazolyl or triazolyl;

when X is phenylcarbonyloxy, phenoxy or phenylthio, the phenyl moiety may be substituted with up to one substituent selected from chloro, fluoro, bromo, iodo and methyl;

Y and Z are each independently hydrogen, bromo, chloro, iodo, fluoro, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio((C₁ -C₂)alkyl, (C₁ -C₂)alkoxy, carbamoyloxy, thiocarbamoylthio, hydroxy, azido or (C₁ -C₄)alkylcarbonyloxy and either Y or Z may be imidazolyl or triazolyl; and

R¹ and R² are each independently selected from hydrogen and (C₁ -C₆)alkyl.

2. The compound of claim 1 wherein

A is a pyridyl which may be substituted with up to three substituents selected from chloro, bromo, fluoro or iodo atoms;

R¹ and R² are each independently a (C₁ -C₄)alkyl group;

X is a chloro, bromo, iodo, methylsulfonyloxy, thio(C₁ -C₂)alkyl, isothiocyano or thiocyano group;

Y is a hydrogen, bromo, chloro, cyano or iodo atom; and

Z is a hydrogen, chloro or bromo atom.

3. The compound of claim 2 wherein

A is a pyridyl which may be substituted with one or two substituents each independently selected from chloro and bromo atoms;

R¹ and R² are each independently (C₁ -C₂)alkyl;

X is a bromo, iodo, methylsulfonyloxy, isothiocyano or thiocyano group;

Y is a hydrogen, bromo, chloro or iodo atom; and

Z is a hydrogen atom.

4. The compound of claim 3 wherein R¹ is a methyl group;

R² is an ethyl group;

X is a bromo atom or thiocyano;

Y is a hydrogen, bromo, iodo or chloro atom; and

Z is a hydrogen atom.

5. The compound of claim 4 wherein the compound is selected from:

N-(1'"'"'-thiocyano-3'"'"'-methylpentan-2'"'"'-on-3'"'"'-yl)-6-chloronicotinamide,

N-(1'"'"'-bromo-3'"'"'-methylpentan-2'"'"'-on-3'"'"'-yl)-5,6-dichloronicotinamide, and

N-(1'"'"',1'"'"'-dibromo-3'"'"'-methylpentan-2'"'"'-on-3'"'"'-yl)-2,6-dichloroisonicotinamide, and

N-(1'"'"'-bromo-1'"'"'-chloropentan-2'"'"'-on-3-yl)-6-chloronicotinamide

7. A fungicidal composition comprising a fungicidally effective amount of the compound of claim 1 and an agronomically acceptable carrier.

8. A fungicidal composition comprising a fungicidally effective amount of the compound of claim 2 and an agronomically acceptable carrier.

9. A method for controlling phytopathogenic fungi comprising applying to a plant, to plant seed or to plant habitat a fungicidally effective amount of the compound of claim 1.

10. The method of claim 9 wherein the compound is applied in an amount of from about 0.5 to about 20 kilograms per hectare.

11. A method for controlling phytopathogenic fungi comprising applying to a plant, to plant seed or to plant habitat a fungicidally effective amount of the compound of claim 2.

12. The method of claim 11 wherein the compound is applied in an amount of from about 1 to about 5 kilograms per hectare.

6. A compound selected from the group consisting of

N-(1'"'"',1'"'"'-dibromo-3'"'"'-methylpentan-2'"'"'-on-3'"'"'-yl)-4-fluoro-2-naphthoic amide,

N-(1'"'"'-bromo-1'"'"'-fluoro-3'"'"'-methylpentan-2'"'"'-on-3'"'"'-yl)-6-chloro-5-methylnicotinamide, and

N-(3'"'"'-bromo-3'"'"'-chloro-1'"'"',1'"'"'-dimethylacetonyl)-2,6-dimethylisonicotinamide.