US 5,187,185 A · Pesticidal 1-arylpyrroles

Abstract

Substituted-1-arylpyrrole compounds of general formula (I) below, are useful as pesticides, in particular for the control of insects, arachnids, and nematodes. Processes to make the compounds and intermediates used for their preparation are described. Additionally, compositions containing the compounds and methods of use therefore are provided. Preferred compounds are the compounds of general formula (I) ##STR1## wherein typically preferred substituents are: X is halogen or a group R.sup.5 S(O).sub.n, in which n is 0, 1, or 2 and R.sup.5 is CH.sub.3, CF.sub.3, CCl.sub.3, CF.sub.2 Cl, CFCl.sub.2, CF.sub.2 Br, CHF.sub.2, CHCl.sub.2 or CHClF; R.sup.1 is H, F, Cl, Br, OCH.sub.3, SCH.sub.3, or CH.sub.3 optionally substituted; R.sup.2 is CN; R.sup.3 is H, F, Cl, Br, OCH.sub.3, or CH.sub.3 optionally substituted; Y is CF.sub.3, CF.sub.3 O, H, F, Cl or Br; X.sup.1 and X.sup.4 are individually H, F, Cl, Br, CH.sub.3, OCH.sub.3 or SCH.sub.3 ; and X.sup.2 and X.sup.3 are each H.

A pesticidal composition, which is employed as an insecticidal, acaricidal or nematicidal agent, which comprises one or more compatible components selected from the group consisting of a pesticidally acceptable carrier and a pesticidally acceptable surface-active agent and a pesticidally effective amount of a compound of formula (Ia), as active ingredient, ##STR49## wherein:

X is selected from the group consisting of:
halogen, cyano, cyanato, thiocyanato, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkylcarbonyl, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, haloalkenylthio, haloalkenylsulfinyl, haloalkenylsulfonyl, haloalkylthiocarbonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;
and wherein the phenyl groups are optionally substituted with halogen, cyano or haloalkyl groups;
and wherein the alkyl, haloalkyl, alkenyl, haloalkenyl, alkoxy and haloalkoxy groups herein are linear or branched chains, having less than 10 carbon atoms, and the halosubstitution in all these groups consists of one or more halogen atoms, which are the same or different, from mono substitution up to complete poly substitution;
R.sup.1, R.sup.2, and R.sup.3 are individually selected from the group consisting of:
one of the same set of substituents as described for X;
a hydrogen atom;
an alkyl group;
and a substituent of which no more than one of R.sup.1, R.sup.2, and R.sup.3 is selected from the group consisting of formyl, hydroxyiminoalkylidenyl, alkoxyiminoalkylidenyl, azido, amino, alkylamino, dialkylamino, aralkylamino, aminocarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, alkylaminocarbonylamino, arylaminocarbonylamino, benzylideneimino, alkylideneimino, alkoxyalkylideneimino, dialkylaminoalkylideneimino, bis(alkylthio)methyl, bis(arylthio)methyl, alkylthioalkylideneimino, alkoxycarbonylamino, haloalkoxycarbonylamino, and a phenyl optionally substituted with halogen, cyano or haloalkyl;
and wherein the alkyl, haloalkyl, alkenyl, haloalkenyl, haloalkoxy, and alkoxy groups herein are linear or branched chains, having less than 10 carbon atoms, and the halosubstitution in all these groups herein consists of one or more halogen atoms, which are the same of different, from mono substitution up to complete poly substitution;
or R.sup.1, R.sup.2, and R.sup.3 are as defined above and R.sup.1 is furthermore selected from the group consisting of alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenylamino, alkynylamino, cyanoalkyl, aralkylthio, aralkylsulfinyl, aralkylsulfonyl, alkenyloxy, alkynyloxy, alkoxyalkyl, and alkylthioalkyl, and R.sup.3 is furthermore selected from the group consisting of alkenyloxy, alkynyloxy, and alkoxyalkyl;
and no more than one of R.sup.1, R.sup.2, and R.sup.3 is selected from the group consisting of formyl, hydroxyiminoalkylidenyl, alkoxyiminoalkylidenyl, azido, amino, alkylamino, dialkylamino, aralkylamino, alkenylamino, alkynylamino, aminocarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, haloalkysulfonylamino, alkylaminocarbonylamino, arylaminocarbonylamino, benzylideneimino, alkylideneimino, alkoxyalkylideneimino, dialkylaminoalkylideneimino, bis(alkylthio)-methyl, bis(arylthio)methyl, alkylthioalkylideneimino, alkoxy-carbonylamino, haloalkoxycarbonylamino, and a phenyl optionally substituted with halogen, cyano or haloalkyl;
and wherein the alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, haloalkoxy, alkoxy, alkenyloxy, and alkynyloxy groups herein are linear or branched chains, having less than 10 carbon atoms, and the halosubstitution in all these groups herein consists of one or more halogen atoms, which are the same or different, from mono substitution up to complete poly substitution;
and wherein for the aralkyl portion in the above mentioned groups and the phenyl portion are optionally substituted as defined above;
Y is selected from the group consisting of;
halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfinyl, alkylsulfonyl, alkylthio, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkenyl, haloalkenyl, haloalkynyl, and alkynyl;
and wherein the alkyl, alkoxy, haloalkyl, haloalkoxy, alkenyl, haloalkenyl, alkynyl and haloalkynyl groups herein are linear or branched chains, having less than 10 carbon atoms, and the halo substitution in all these groups herein consists of one or more halogen atoms, which are the same or different, from mono substitution up to as much as complete poly substitution;
or Y optionally is a hydrogen atom when:
X is a halogen atom or a group R.sup.5 S(O).sub.n, in which n is 0, 1, or 2 and R.sup.5 is alkyl, haloalkyl, alkenyl or haloalkenyl;
and the alkyl and alkenyl carbon chains and the halo-substitution are as defined above;
R.sup.1 and R.sup.3 are each a hydrogen atom;
and
R.sup.2 is cyano;
X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are individually selected from the same set of substituents as described for Y or a hydrogen atom;
and provided:
that at least one of R.sup.1, R.sup.2, and R.sup.3 is selected from the same set of substituents as described for X;
that if X.sup.4 and X.sup.1 are H, and X is halogen or cyano, then R.sup.2 is different from X;
and
that if X.sup.4 and X.sup.1 are H, and Y is methyl, then X is different from bromo.

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Pesticidal 1-arylpyrroles

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Pesticidal 1-arylpyrroles

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Abstract

Claims64