US 5,202,356 AGranted

Pesticidal cyclopropyl-2,4-dieneamides

AssigneeThe Wellcome Foundation Limited

InventorsRobert J. Blade, George S. Cockerill, John E. Robinston

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Abstract

The present Application discloses pesticidally active compounds of the formula (I): Q Q.sup.1 CR.sup.2 =CR.sup.3 CR.sup.4 =CR.sup.5 C (.dbd.X) NHR.sup.1 or a salt thereof, wherein Q is an monocyclic aromatic ring. or fused 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 optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, 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; R.sup.2,R.sup.3, R.sup.4 and R.sup.5 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 is oxygen or sulphur; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy. their preparation, pesticidal compositions containing them and their use against pests.

Claims15

Dependent claims

A compound of the formula (I):

QQ.sup.1 CR.sup.2 .dbd.CR.sup.3 CR.sup.4 .dbd.CR.sup.5 C (.dbd.X) NHR.sup.1
or a salt thereof, wherein Q is a substituted monocyclic aromatic ring, or fused 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 or the bicyclic ring system is substituted by one to four groups selected from C.sub.1-6 hydrocarbyl, C.sub.1-6 alkoxy or methylenedioxy, or C.sub.1-6 hydrocarbyl, C.sub.1-6 alkoxy or methylenedioxy substituted by one to three halos, or from halo, cyano or nitro,
or the substituent on the Q ring is a group S(O).sub.n R.sup.7 wherein n is 0, 1 or 2 and R.sup.7 is C.sub.1-6 alkyl or C.sub.1-6 alkyl substituted by one or more halos or R.sup.7 is amino or amino substituted by one or two C.sub.1-6 alkyl groups or the substituent is a group NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 are independently selected from hydrogen, C.sub.1-6 alkyl or a group COR.sup.10 where R.sup.10 is C.sub.1-6 alkyl,
or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen;
Q.sup.1 is a 1,2-cyclopropyl ring or a 1,2-cyclopropyl ring substituted by one or more groups selected from C.sub.1-3 alkyl, halo, C.sub.1-3 haloalkyl, alkynyl, or cyano;
R.sup.2, R.sup.3, R.sup.4 and R.sup.5 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 is oxygen or sulfur;
and
R.sup.1 is selected from hydrogen, C.sub.1-8 hydrocarbyl and C.sub.1-8 hydrocarbyl substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy,
provided that the compound of formula (I) is not
(.+-.)-2E,4E)-N-Isobutyl-5-[trans-2-(2,6-dichloro-4-pyridyl) cyclo-propyl]-3-methylpenta-2,4-dienamide
(.+-.)-2E,4E)-N-(1,2-Dimethylpropyl)-5-[trans-2-(3,4-dichloropheny)cyclopro pyl]penta-2,4-dienamide
(.+-.)-2e,4E)-N-(1,2-Dimethylpropyl)-5-[trans-2-(4-methoxyphenyl)cyclopropy l]penta-2,4-dienamide.

10 more elements

A compound selected from:

(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(4-bromophenyl)cyclopropyl]penta-2,4-die namide
(.+-.)-(2E/Z,4E) N-Isobutyl-3-methyl-5-(trans-2-(3,5-bistrifluoro methylphenyl) cyclopropyl)-2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-(trans-2-(3,5-bistrifluoro methylphenyl)cyclopropyl)-2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-(trans2-(3,4-dichlorophenyl) cyclopropyl) 2,4-dienamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-(trans-2-(3,4-dichlorophenyl cyclopropyl)-2,4-dienamide.
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-(trans-2-(4-chlorophenyl) cyclopropyl)-2,4-dienamide.
(.+-.)-(2E,e4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(3,4-dibromophenyl)cyclopropyl]penta-2,4 -dienamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-[trans-2-(3,4-dibromophenyl)cyclopropyl]penta-2,4-di enamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-methyl-5-[trans-2-(4-chlorophenyl) cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E,4E) -(2-Methylprop-2-enyl)-3-methyl-5-[trans-2-(3,4-dibromophenyl)cyclopropyl ]penta-2,4-dienamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-[trans-2-(3-trifluoromethyl-4-chlorophenyl)cycloprop yl ]penta-2,4-dienamide
(.+-.)-2E,4E) N-Isobutyl-3-methyl-5-[trans-2-(3,5-dichloro-4-bromophenyl) cyclopropyl]penta-2,4-dienamide.
(.+-.)-2E,4E) N-Isobutyl-3-methyl-5-[trans-2-(3,4,5-trichlorophenyl)cyclopropyl]penta-2, 4-dienamide
(.+-.)-(2E,4Z) N-Isobutyl-3-methyl-4-fluoro-5-[trans-2-(3,4-dichlorophenyl)cyclopropyl]pe nta-2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(3-chloro-4-bromophenyl) cyclopropyl]penta-2,4-dienamide.
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-[trans-2-(3-chloro-4-bromophenyl)cyclopropyl]penta-2 , 4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(3-bromo-4-chlorophenyl)cyclopropyl]pent a-2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl-5-[r-1-fluoro-c-2-(3,4,5-trichlorophenyl)cyclopropyl ]penta-2,4-dienamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-[r-1-fluoro-c-2-(3,4,5-trichlorophenyl)cyclopropyl]p enta-2,4-dienamide
(.+-.)-(2Z,4E) N-Isobutyl-2-fluoro-3-methyl-5-[trans-2-(3,4-dichlorophenyl)cyclopropyl]pe nta-2,4-dienamide
(.+-.)-(2Z,4E) N-(2-Methylprop-2-enyl)-2-fluoro-3-methyl-5-(trans-2-(3,4-dichlorophenyl) cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E,4E) N-(sec-Butyl)-5-[trans-2-(3,4-dichlorophenyl)cyclopropyl]penta-2,4-dienami de
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[r-1-fluoro-c-2-(3,4-dichlorophenyl)cyclopropyl]p enta=2,4-dienamide
(.+-.)-(2E/Z,4E) N-(2-Methylprop-2-enyl)-3-methyl-5-[r-1-fluoro-c-2-(3,4-dibromophe nyl)cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E/Z,4E) N-Isobutyl-3-methyl-5-[r-1-fluoro-c-2-(3,4-dibromophenyl)cyclopropyl]penta -2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[r-1-fluoro-c-2-(3,4-dibromophenyl)cyclopropyl]pe nta-2,4-dienamide
(.+-.)-(2E/Z,4E) N-Isobutyl-3-methyl-5-[r-1-fluoro-c-2-(3,4-dichlorophenyl)cyclopropyl]pent a-2,4-dienamide
(.+-.)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[r-1-chloro-c-2-(3,4-dichlorophenyl)cyclopropyl]p enta=2,4-dienamide
(.+-.)-(2E,4Z) N-(2-Methylprop-2-enyl)-3-methyl-4-fluoro-5-[trans-2-(3,4-dichlorophenyl) cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E,4E) N-Isobutyl-3-methyl-5-[r-1-chloro-2-c-(3,4-dichlorophenyl)cyclopropyl]pent a--2,4-dienamide
(.+-.)-(2E/Z,4E) N-(2-Methylprop-2-enyl)-3-methyl-5-[r-1-fluoro-2-c-(3,4-dichlorophenyl) cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E/Z,4E) N-(2-Methylprop-2-enyl)-3-methyl-5-[r-1-fluoro-2-c-(3,4-5-triclorophenyl) cyclopropyl]penta-2,4-dienamide
(.+-.)-(2E,4E) N-(2-Methylprop-2-enyl)-3-methyl-5-[trans-2-(3,4-dibromophenyl)cyclopropyl ]penta-2,4-dienamide.

30 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/729,847Filed 12 Jul 1991 · continuation
Priority: GB 882676016 Nov 1988
Granted: 13 Apr 1993
Term ends: Not estimatedThe source records don’t support an estimate.

Classification29 codes

C07F 9/247
The amide moiety containing a substituent or a structure which is considered as characteristic: of aromatic amines
A01N 37/18
Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to…:…
A01N 49/00
Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing
C07C 45/00
Preparation of compounds having >c = o groups bound only to carbon