Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2000-03-24
2001-06-12
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C564S044000
Reexamination Certificate
active
06245816
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention provides novel benzoylphenylurea insecticides and novel methods of inhibiting cockroaches, ants, fleas, and termites.
A broad class of benzoylphenylurea insecticides is disclosed in U.S. Pat. No. 3,748,356. European Patent Application 263438 discloses that certain N-substituted phenyl-N′-substituted benzoyl-N-methylureas are highly safe to beneficial aquatic Crustacea while exhibiting equal or superior insecticidal activities to non-alkylated analogs. Hexaflumuron, a commercially significant benzoylphenylurea, is disclosed in U.S. Pat. No. 4,468,405. Use of hexaflumuron in methods of controlling termites is disclosed in WO 93/24011. Use of hexaflumuron to control cockroaches is disclosed in WO 94/03066. The compound N-[3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-N′-(2,6-difluorobenzoyl)urea is disclosed in DE 3827133 and European Patent Application A 243,790, but there was no disclosure of the unexpected activity of the compound against cockroaches, ants, fleas, and termites.
We have discovered that certain benzoylphenylurea compounds, some of which are novel, have substantially greater activity against cockroaches, ants, fleas, and termites than would have been expected based on comparison with the closest prior art, i.e., hexaflumuron. Another significant property of the novel compounds of the invention is their surprisingly low toxicity to Daphnia.
SUMMARY OF THE INVENTION
The invention provides a method of controlling cockroaches, ants, fleas, or termites which comprises delivering a effective amount of a compound of the formula (I):
wherein R
1
and R
2
are H, methyl, or ethyl, to a location where control of cockroaches, ants, fleas, or termites is desired.
More specifically, the invention provides:
A method of controlling cockroaches which comprises a compound of the formula (I), in an amount effective to control cockroaches, to a location where control of cockroaches is desired;
A method of controlling ants which comprises delivering a compound of the formula (I), in an amount effective to control ants, to a location where control of ants is desired;
A method of controlling fleas which comprises delivering a compound of the formula (I), in an amount effective to control fleas, to a location where control of fleas is desired; and
A method of controlling termites which comprises delivering a compound of the formula (I), in an amount effective to control termites, to a location where control of termites is desired.
The invention also provides novel compounds of the formula (II)
wherein R
1
′ and R
2
′ are H, methyl, or ethyl, provided that at least one of R
1
′ and R
2
′ is methyl or ethyl.
REFERENCES:
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patent: 2166134 (1986-04-01), None
patent: WO 94/03066 (1994-02-01), None
patent: WO 95/16354 (1995-06-01), None
patent: WO 97/40689 (1997-11-01), None
Journal of Economic Entomology (Oct. 1996), vol. 89, No. 5, pp. 1156-1160, Nan-Yao Su and Rudolf H. Scheffrahn, “Comparative Effects of Two Chitin Synthesis Inhibitors, Hexaflumuron and Lufenuron, in a Bait Matrix Against Subterranean Termites (Isoptera: Rhinotermitidae)”.
Doppelreiter et al.,Entwicklungshemmung durch Diflubenzuron bei den Bodentermiten Heterotermes indicola und Reticulitermes flavipes, Z. ang. Ent. 91, Verlan Paul Parcy, Hamburg und Berlin, (1982), 131-37.
Edwards Jeff M.
Johnson George W.
Karr Laura L.
Schneider Brian M.
Spragia Ronald J.
Corvin Carl D.
O'Sullivan Peter
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