IP Library Granted Patent US 8,324,209
Granted Patent B2
US 8,324,209 · App. 12/547,049 · Granted Dec 4, 2012

Pesticidal compositions

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Quick Facts
Patent No.
US 8,324,209
App. No.
12/547,049
Granted
Dec 4, 2012
Kind
B2
Abstract

Pesticide compositions and their use in controlling pests are provided.

Claims (33)

1. A composition comprising a compound having the following general formula:

wherein

R1 is

(a) an unsubstituted pyrimidinyl, pyridazinyl, or pyrazinyl, or

(b) a substituted pyrimidinyl, pyridazinyl or pyrazinyl, wherein each substituted pyrimidinyl, pyridazinyl, or pyrazinyl, has one or more substituents independently selected from (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, halo, halo(C 1 -C 6 )alkyl, or heterocyclyl;

R2 is H, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, halo, halo(C 1 -C 6 )alkyl, or heterocyclyl;

R3 is H, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, halo, halo(C 1 -C 6 )alkyl, or heterocyclyl;

Optionally, R2 and R3 may form a ring wherein the ring contains 3 or more ring atoms optionally containing an O, S, or N atom;

R4 is H, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, halo, halo(C 1 -C 6 )alkyl, or heterocyclyl;

Optionally, R4 and R2 are joined together to form a 4-, 5-, or 6-membered ring with —(CH 2 )—;

R5 is NO 2 , CN, CO 2 R 6 , unsubstituted heterocyclyl, substituted heterocyclyl, C(═(O or S))J(J1)(J2),

wherein the substituted heterocyclyl has one or more substitutents that are independently selected from (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, aryl, aryl(C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, halo, halo(C 1 -C 6 )alkyl, heterocyclyl, and

wherein J is N or C(J3), and

wherein J1, J2, and J3, are independently selected from (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 2 -C 6 )alkenylthio, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylthio, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, (C 2 -C 6 )alkynylthio, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkenylthio, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, (C 3 -C 6 )cycloalkylthio, H, heterocyclyl, or (C 0 -C 6 )alkyl-C(═O)O(J4), wherein each of which may be independently substituted (except for H) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkoxy, halo(C 1 -C 6 )alkylthio, S(═O) n1 (C1-C 6 )alkyl (where n1=0-2), S(═O) n2 halo(C 1 -C 6 )alkyl (where n2=0-2), OSO 2 halo(C 1 -C 6 )alkyl, C(═O)O(C 1 -C 6 )alkyl, C(═O)(C 1 -C 6 )alkyl, C(═O)halo(C 1 -C 6 )alkyl, aryl, hydroxy(C 1 -C 6 )alkyl, N(J5)(J6), and heterocyclyl, and

wherein J1 and J2 may also form a 4-, 5-, or 6-membered ring, and

wherein J4, J5, and J6 are independently selected from (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyloxy, (C 2 -C 6 )alkenylthio, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylthio, (C 2 -C 6 )alkynyl, (C 2 -C 6 )alkynyloxy, (C 2 -C 6 )alkynylthio, aryl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, (C 3 -C 6 )cycloalkenylthio, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, (C 3 -C 6 )cycloalkylthio, H, or heterocyclyl, and

wherein R6=(C 1 -C 3 )alkyl; and

n is 0, 1, 2, or 3.

2. A composition according to claim 1 wherein R1 is

3. A composition according to claim 1 , wherein R1 is a substituted pyrimidinyl, pyridazinyl, or pyrazinyl, wherein each substituted pyrimidinyl, pyridazinyl, or pyrazinyl, has one or more substituents independently selected from halo and halo(C 1 -C 6 )alkyl.

4. A composition according to claim 1 , wherein R2 is H or (C 1 -C 6 )alkyl.

5. A composition according to claim 1 , wherein R3 is H or (C 1 -C 6 )alkyl.

6. A composition according to claim 1 , wherein R4 is H or (C 1 -C 6 )alkyl.

7. A composition according to claim 1 , wherein R5 is NO 2 or CN.

8. A composition according to claim 1 , wherein R1 is a substituted pyrimidinyl, pyridazinyl, or pyrazinyl, wherein each substituted pyrimidinyl, pyridazinyl, or pyrazinyl, has one or more substituents independently selected from halo and halo(C 1 -C 6 )alkyl;

R2 is H or (C 1 -C 6 )alkyl;

R3 is H or (C 1 -C 6 )alkyl;

R4 is H or (C 1 -C 6 )alkyl;

R5 is NO 2 or CN; and

N is 0, 1, 2, or 3.

9. A composition comprising a compound having the following formula

10. A composition comprising a compound having the following formula

11. A composition comprising a compound having the following formula

Assignments (2)
CHANGE OF NAME Recorded Nov 8, 2021
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 058044/0184 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 5, 2009
From: NUGENT, BENJAMIN M.; BENKO, ZOLTAN L.; RENGA, JAMES M.; LOSO, MICHAEL R.; MARTIN, TIMOTHY P.
To: DOW AGROSCIENCES LLC
Reel/Frame 023325/0895 →