2-pyridylmethylamine derivatives useful as fungicides

• US 6,503,933 B1
• Filed: 09/21/2000
• Issued: 01/07/2003
• Est. Priority Date: 02/19/1998
• Status: Expired due to Term

• Current Assignee: Aventis Cropscience NV (Bayer AG)
• Original Assignee: Aventis Cropscience NV (Bayer AG)
• Inventors: Hardy, David, Moloney, Brian Anthony, Saville-Stones, Elizabeth Anne
• Primary Examiner(s): Rotman, Alan L.
• Assistant Examiner(s): ROBINSON, BINTA M
• Application Number:
  US09/622,651
• Time in Patent Office: 838 Days
• Field of Search: 546/336, 546/331, 546/337, 546/287, 546/291, 546/307, 546/330, 514/357, 514/345, 514/353
• US Class Current: 514/357
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: C07D 213/26 Radicals substituted by halogen atoms or nitro radicals
• CPC Class Codes: C07D 213/61 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 213/65 attached in position 3 or 5
• CPC Class Codes: C07D 213/85 in position 3
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

Compounds of formula (I) and salts thereof as phytopathogenic fungicides wherein A¹ is substituted 2-pyridyl; A² is optionally substituted phenyl; L is —(C═O)—, —SO₂— or —(C═S)—; R¹ is hydrogen, optionally substituted alkyl or acyl; and R² is hydrogen or optionally substituted alkyl are useful phytopathogenic fungicides.

Claims

1. A compound of formula I or a salt thereof

wherein A¹ is a 2-pyridyl group having substituents at the three or five position, or both, and at no other position, R¹ and R² are hydrogen, L is —

(C═

O)—

, —

SO₂—

or —

(C═

S)— and

A² is substituted phenyl,

wherein any A¹ substituent is selected from the group consisting of halogen, hydroxy, cyano, nitro, SF₅, trialkylsilyl, optionally substituted amino, E, OE or SE, where E is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, each of which is optionally substituted, or —

C(E)═

N—

Q, where Q is E, OE, SE or optionally substituted amino, and

wherein the optional substituent

when present on any alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or cycloalkynyl moiety is selected from the group consisting of halogen, cyano, alkoxy, alkylthio, mercapto, hydroxy, nitro, amino, acyl, acyloxy, acylthio, phenyl, phenylthio, phenoxy,

when present on any cycloalkyl, cycloalkenyl or cycloalkynyl is an alkyl, alkenyl or alkynyl,

when present on any phenyl group are selected from the same group as the A¹ substituents, and

when present on any amino group is E or acyl.

2. A compound according to claim 1 in which A² is phenyl substituted with halogen.

3. A compound according to claim 1 in which L is —

(C═

O)—

.

4. A compound according to claim 3 in which A¹ is 2-pyridyl substituted by at least one member of the group consisting of fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro and methoxy and A² is phenyl substituted with halogen.

5. A method of combating phytopathogenic fungi, at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I or a salt thereof

wherein

A¹ is substituted 2-pyridyl;

A² is substituted phenyl;

L is —

(C═

O)—

, —

SO₂—

or —

(C═

S)—

;

R¹ is hydrogen, optionally substituted alkyl or acyl; and

R² is hydrogen or optionally substituted alky.

6. The method of claim 5, in which A¹ is a 2-pyridyl group having substituents at the 3 or 5 positions, or both, and at no other position, and R¹ and R² are hydrogen.

7. A method according to claim 6 in which A² is phenyl substituted with halogen.

8. A method according to claim 6 in which L is —

(C═

O)—

.

9. A method according to claim 8 in which A¹ is 2-pyridyl substituted by at least one member of the group consisting of fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro and methoxy and A² is phenyl substituted with halogen.