Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Silicon containing doai
Patent
1992-09-10
1994-07-05
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Silicon containing doai
514524, 514526, 514549, 514599, 556465, 558388, 558390, 560 9, 560 19, 560 21, 560 41, 560147, 560153, 560160, 560163, 560170, 564162, 564163, 564182, 564204, C07F 710, C07C23312, C07C22247, A01N 5500
Patent
active
053267559
DESCRIPTION:
BRIEF SUMMARY
This invention relates to pesticidal compounds, processes for their preparation, compositions containing them and to their use in the treatment of pests.
Unsaturated amides having a C.sub.1-10 alkylene chain optionally including oxygen atoms are known as pesticides having various terminating groups which include within their scope optionally substituted phenyl (European Application Nos. 228222, 194764, 225011, Japanese Application No 57-212150, Meisters and Wailes: Aust. J. them. 1966, 19, 1215, Vig et al : J. Ind. Chem. Soc. 1974, 51(9), 817) or pyridyl (European Application 269457) or fused bicyclic ring systems (European Application Nos. 143593, 228853), or dihalovinyl or optionally substituted ethynyl (European Application 228222) groups.
Novel unsaturated amides having a 1,2-cyclopropyl ring adjacent to the diene unit linking the latter to a terminal group selected from optionally substituted monocyclic aromatic or fused bicyclic ring system, dihalovinyl or optionally substituted ethynyl have interesting pesticidal properties and are described in European Patent Application No. 893 11815.8.
Such compounds are secondary amides in which the N substituents are generally hydrogen and an alkyl group. It has now been found that certain tertiary amides, generally having a heteroatom or a carbon bearing a heteroatom attached to the amide nitrogen, have pestictdal activity.
Accordingly, the present invention provides a compound of formula (I): NR.sup.5 R.sup.6 (I) bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.7 --C.dbd.C-- where R.sup.7 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsily, halogen or hydrogen; Q.sup.1 is a 1,2-cyclopropyl ring optionally substituted by one or more groups selected from C.sub.1-3 alkyl, halo, C.sub.1-3 haloalkyl, alkynyl, or cyano; R1, R.sup.2, R.sup.3 and R.sup.4 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; X.sup.1 is oxygen or sulphur; R.sup.5 is C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy; and R.sup.6 is selected from: phosphorus or carbon, R.sup.8 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-5 alkylcarbonyl or aryl or CO.sub.2 R.sup.9 where R.sup.9 gis an C.sub.1-4 alkyl or aryl and a is 1 or 2 aryloxy or C.sub.1-4 alkoxy, wherein the aryl ring may be substituted by one or more halo, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy groups each in turn optionally substituted by one or more halogens, or R.sup.10 is a group NR.sup.11 R.sup.12 wherein R.sup.11 is --COR.sup.13 where R.sup.13 is hydrogen, fluorine or C.sub.1-4 alkyl or R.sup.13 is a group CO.CO.sub.2 R.sup.9,SNR.sup.11a R.sup.11b or P(.fwdarw.0)R.sup.8 wherein 11.sup.a and 11.sup.b are the same or different and each is a group R.sup.11 and R.sup.8, R.sup.9 and R.sup.11 as hereinbefore defined, or R.sup.11 is C.sub.1-4 alkyl substituted by C.sub.1-4 alkyl, C.sub.1-5 alkylcarbonyl or aryl, carboalkoxy or cyano, or R.sup.11 is a group CO.sub.2 R.sup.14 where R.sup.14 is C.sub.1-4 alkyl or aryl, R.sup. 12 is C.sub.1-4 alkyl, and b.dbd.0, 1 or 2. hydrogen or C.sub.1-4 alkyl, X.sup.3 is oxygen or sulphur and R.sup.17 is C.sub.1-4 alkyl, C.sub.1-5 alkylcarbonyl or aralkylcarbonyl R.sup.17, R.sup.15 X.sup.3 may be linked to form a ring system. containing an oxygen or sulphur atom optionally substituted by C.sub.1-4 alkyl.
By the term aryl is meant a carbocyclic or heterocyclic aromatic ring containing 5-10 ring atoms, preferably phenyl or pyridyl.
When Q is a monocyclic aromatic ring, this is suitably phenyl, pyridyl or thienyl and preferably phenyl. When Q is a bicyclic ring system, this is preferably naphthyl.
When Q contains an aromatic system, suitable substituents include one to four groups selected from C.sub.1-6 hydrocarbyl, C.sub.1-6 a
REFERENCES:
Chemical Abstracts, vol. 117 (19) Abst. No. 117:19), 490-(b) Nov. 9, 1992.
Blade Robert J.
Cockerill George S.
Rotman Alan L.
Roussel Uclaf
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