IP Library Granted Patent US 8,058,279
Granted Patent B2
US 8,058,279 · App. 12/238,998 · Granted Nov 15, 2011

Insecticidal pyrimidinyl aryl hyrdrazones

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Quick Facts
Patent No.
US 8,058,279
App. No.
12/238,998
Granted
Nov 15, 2011
Kind
B2
Abstract

Pyrimidinyl aryl hydrazones are effective at controlling insects.

Claims (27)

1. A compound of formula (I)

wherein

X 1 and Y 1 independently represent H, halogen, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 halothioalkyl, or C 1 -C 6 haloalkyl substituted with hydroxy or C 1 -C 6 acyloxy, with the proviso that at least one of X 1 or Y 1 is not H;

X 2 and Y 2 independently represent H, halogen, CN, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 halothioalkyl, 1-pyrrolidinyl, 1-piperidinyl, or C 1 -C 6 haloalkyl substituted with a substituent selected from the group consisting of hydroxy and C 1 -C 6 acyloxy, with the proviso that at least one of X 2 or Y 2 is not H;

Z represents CH or N;

L represents H, halogen or C 1 -C 3 haloalkyl;

Q represents H, halogen, OR 3 , C 1 -C 3 -haloalkyl, SR 3 or NR 4 R 5 ;

R 1 and R 2 independently represents H or CH 3 ;

R 3 represents C 1 -C 4 alkyl which may be unsubstituted or substituted with from one to the maximum number of chloro or fluoro substituents;

R 4 represents H or C 1 -C 4 alkyl; and

R 5 represents

C 1 -C 4 alkyl, which may be unsubstituted, or substituted with from one to the maximum number of chloro or fluoro substituents, or with a substituent selected from the group consisting of C 1 -C 4 alkoxy, C 1 -C 4 alkylamino, and a pyridin-3-yl substituted in the 6-position of the pyridine ring with halogen,

C 1 -C 4 alkoxy, or

C 1 -C 4 haloalkyl.

2. A compound according to claim 1 in which Z is CH.

3. A compound according to claim 1 in which one of X 1 and Y 1 is F, Cl, Br, CN, CF 3 , OCF 3 , OCF 2 CHF 2 or CH(CF 3 )OH.

4. A compound according to claim 3 in which X 1 and Y 1 are meta- or para-substituents relative to the —NR 1 — substituent.

5. A compound according to claim 1 in which one of X 2 and Y 2 is F, Cl, Br, CN, CF 3 , OCF 3 , 1-pyrollidinyl, 1-piperidinyl, OCF 2 CHF 2 or C(CF 3 ) 2 OH.

6. A compound according to claim 5 in which X 2 and Y 2 are meta- or para-substituents relative to the —CH═N—N—R 2 — substituent.

7. A compound according to claim 1 in which Q is H, Cl, F, CF 3 , CH 3 OCH 2 CH 2 NH, EtNHCH 2 CH 2 NH, CF 3 CH 2 O, or

8. A compound according to claim 1 in which L is H, Cl, F or CF 3 .

9. A compound according to claim 1 having the structure

10. A compound according to claim 1 having the structure

11. A compound according to claim 1 having the structure

12. A composition for controlling insects which comprises a compound of claim 1 in combination with a phytologically-acceptable carrier.

13. A method of controlling insects which comprises applying to a locus where control is desired an insect-inactivating amount of a compound of claim 1 .

14. A compound according to claim 1 having the following structure

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 8, 2008
From: GUENTHENSPBERGER, KATHERINE A.; JOHNSON, TIMOTHY C.; NIYAZ, NOORMOHAMED M.; HUNTER, RICKY; BROWN, ANNETTE V.; TRULLINGER, TONY K.
To: DOW AGROSCIENCES LLC
Reel/Frame 021647/0043 →