Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Statutory Invention Registration
1998-11-20
2001-10-02
Morris, Patricia (Department: 3641)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S192000, C546S194000, C546S210000, C514S317000, C514S318000, C514S326000
Statutory Invention Registration
active
H0001996
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates generally to insecticidal compounds for use in controlling insects. In particular, it pertains to certain agriculturally acceptable organic and inorganic acid salt derivatives of N-benzyl-4-benzhydrolpiperidines and their corresponding N-oxides having improved photostability while providing insecticidal activity generally equivalent to the parent compound. This invention also pertains to the insecticidal compositions of these salt derivatives, and a method of controlling insects at a locus which comprises applying to that locus a compound of the invention or an insecticidal composition containing the compound.
There is a continuing demand for new insecticides that are safer, more effective, and less costly. Insecticides are useful for controlling insects which may otherwise cause significant damage to crops such as wheat, corn, soybeans, potatoes, and cotton to name a few. For crop protection, insecticides are desired which can control the insect pests without damaging the crops, and which have no deleterious effects to mammals and other living organisms. Photostable insecticides are advantageous in that they promote residual insecticidal activity which increases the effectiveness of the insecticidally active material.
U.S. Pat. No. 5,569,664 and U.S. Pat. No. 5,639,763 disclose a class of piperidine derivatives, the corresponding N-oxides and agriculturally acceptable salts for use as insecticides:
in which, among others,
U is —(CH
2
)
n
— where n is 1, 2, or 3;
Q is hydroxy;
R is selected from a heterocycle having 5 or 6 ring atoms, optionally fused to a benzene ring, and
where
V, W, Y, and Z are hydrogen; and,
X is hydrogen, hydroxy, halogen, alkyl, alkoxyalkyl, alkoxy, cycloalkylalkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, alkylsilyloxy, alkylthio, haloalkylthio, cyano, cyanoalkoxy, nitro, amino, monoalkylamino, dialkylamino, alkylaminoalkoxy, alkylcarbonylamino, alkylcarbonyl, alkoxycarbonylamino, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyloxy, phenyl, phenylalkoxy, phenoxy, phenoxyalkyl, or a five- or six-membered heterocycl; each cycloalkyl moiety, heterocycle, or phenyl ring is optionally substituted with halogen, alkoxy, or haloalkoxy;
W and X taken together may be —OCH
2
CH
2
O—, —CH
2
C(CH
3
)
2
O—, —OC(CH
3
)
2
O—, —N═C(C
2
H
5
)O—, or —CH═CHCH═C—;
R
1
and R
2
are independently selected from phenyl substituted with one or more haloalkyl or haloalkoxy.
The '664 and '763 patents do not disclose improved photostablility of agriculturally acceptable salts of piperidines or piperidine N-oxides.
SUMMARY OF THE INVENTION
It has now been found that certain novel agriculturally acceptable organic and inorganic acid salts of N-benzyl-4-benzhydrolpiperidines and their corresponding N-oxides have improved photostablility, and are useful as insecticides. These compounds are represented by formula I:
wherein R, R
1
, and n are as defined below. Preferred compounds include those where R is 2-alkyl-2H-tetrazol-5-yl; R
1
is trifluoromethyl, or trifluoromethoxy; n is 1; and said salts are derived from hydrochloric acid, or a sulfonic acid.
REFERENCES:
patent: 5077301 (1991-12-01), Pein et al.
patent: 5569664 (1996-10-01), Silverman et al.
patent: 5639763 (1997-06-01), Silverman et al.
patent: 5795901 (1998-08-01), Szcepanski
patent: WO 96/36228 (1996-11-01), None
patent: WO 97/22583 (1997-06-01), None
Cullen Thomas G.
Dybas Jane A.
Henrie II Robert N.
Peake Clinton J.
Baker Aileen J.
Fair Paul A.
FMC Corporation
Goodell James D.
Morris Patricia
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