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US 6,271,392 B1Granted
Intermediates useful for the synthesis of 1-arylpyrrole pesticides
AssigneeRhone-Poulenc Inc.
InventorsAlain Chene, Scot Kevin Huber
Life of this patent
Estimating the term…
Abstract
The present invention pertains to novel 3-substituted-4-thiopyrrole intermediates for the preparation of 1-arylpyrrole compounds that are useful for the control of insects, acarids and nematodes. The compounds, including their isomers, e.g., diastereomers and optical isomers, are compounds of a general formula (I) wherein the structural variables are as defined in the description.
Claims16
A compound of the formula:
- wherein:
- W is cyano, —CO2H, —CO2R3, —CONH2, —CONHR3, —CON(R3)2, —CSNH2, —CSNHR3, —CSN(R3)2, —COSH, —COSR3, —CHO, —CH═NOH, —CH═NOR3, or nitro;
- R is alkyl, haloalkyl, cyano, —C(NH2)(═NH) or an acid addition salt thereof, hydrogen, or
- R1 and R2 independently represent hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, cyano, nitro, NR11R12, formyl, alkylcarbonyl, haloalkylcarbonyl, hydroxyalkylcarbonyl, —CO2H, —CO2R3, alkylthiocarbonyl, —CONH2, —CONHR3, —CON(R3)2, bis(alkoxy)methyl, bis(alkylthio)methyl, (alkoxy)(cyano)methyl, (acyloxy)(cyano)methyl, (phenoxy)(cyano)methyl, (alkoxy)(alkylthio)methyl, (alkylamino)(alkoxy)methyl, (alkoxy)(dialkylamino)methyl, (alkylamino)(alkylamino)methyl, (dialkylamino)(dialkylamino)methyl, (alkoxy)(alkoxycarbonyl)methyl, (alkoxy)(aminocarbonyl)methyl, (alkoxy)(alkylaiinocarbonyl)methyl, (alkoxy)(dialkylaminocarbonyl)methyl, alkoxyalkyl, hydroxyalkyl, (haloalkoxy)alkyl, (alkoxy)(haloalkyl)alkyl, cyanoalkyl, halogenated cyanoalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, monoalkylaminocarbonylalkyl, formylalkyl, dialkylaminocarbonylalkyl, alkoxyalkylcarbonyl, alkylsulfenylalkylcarbonyl, alkylsulfmylalkylcarbonyl, alkylsulfonylalkylcarbonyl, cyanoalkylcarbonyl, alkoxycarbonylalkylcarbonyl, aminocarbonylalkylcarbonyl, monalkylaminocarbonylalkylcarbonyl, dialkylaminocarbonylalkylcarbonyl, —CH═N—O—R11, amino(thio)carbonyl, monoalkylamino(thio)carbonyl, dialkylamino(thio)carbonyl, or a radical of the formula
- wherein:
- R13 is hydrogen, alkyl, or haloalkyl;
- Y and Z are O, S, SO, SO2, NH, N-alkyl, or N-acyl;
- Q is ethylene or propylene optionally substituted with alkyl, haloalkyl, alkoxy, alkoxyalkyl, cyano, hydroxyalkyl, amino, alkylamino, dialkylamino, alkylsulfenyl, alkylsulfmyl, alkylsulfonyl, OH, or SH;
- s is 0 to 3;
- R3 is alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl;
- R11, and R12 independently represent H, alkyl, haloalkyl, formyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfinyl, haloalkylsulfimyl, allyl, propargyl, halogen, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkoxyalkyl, haloalkylthioalkyl, haloalkylsulfmylalkyl, haloalkylsulfonylalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, or alkoxycarbonyl;
- and
- n is 0, 1 or 2,
- provided that when R1 is methyl, then R2 is not hydrogen or alkyl, W is not —CO2R3 and n is not 0;
- and
- provided that when W is —CO2C2H5, then R is not —C(NH2)(═NH) or an acid addition salt thereof.
13 more elements
A compound of the formula:
- wherein:
- W is cyano, —CO2H, —CO2R3, —CONH2, —CONHR3, —CON(R3)2, —CSNH2, —CSNHR3, —CSN(R3)2, —COSH, —COSR3, —CHO, —CH═NOH, —CH═NOR3, or nitro;
- R is alkyl, cyano, —C(NH2)(═NH) or an acid addition salt thereof, hydrogen, or
- R1 and R2 independently represent hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfmyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfmyl, haloalkylsulfonyl, cyano, nitro, NR11R12, formyl, alkylcarbonyl, haloalkylcarbonyl, hydroxyalkylcarbonyl, —CO2H, —CO2R3, aylthiocarbonyl, —CONH2, —CONHR3, —CON(R3)2, bis(alkoxy)methyl, bis(alkylthio)methyl, (alkoxy)(cyano)methyl, (acyloxy)(cyano)methyl, (phenoxy)(cyano)methyl, (alkoxy)(alkylthio)methyl, (alkylamino)(alkoxy)methyl, (alkoxy)(dialkylamino)methyl, (alkylamino)(alkylamino)methyl, (dialkylamino)(dialkylamino)methyl, (alkoxy)(alkoxycarbonyl)methyl, (alkoxy)(aminocarbonyl)methyl, (alkoxy)(alkylaminocarbonyl)methyl, (alkoxy)(dialkylaminocarbonyl)methyl, alkoxyalkyl, hydroxyalkyl, (haloalkoxy)alkyl, (alkoxy)(haloalkyl)alkyl, cyanoalkyl, halogenated cyanoalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, monoaLkylaminocarbonylalkyl, fonnylalkyl, dialkylaminocarbonylalkyl, alkoxyalkylcarbonyl, alkylsulfenylalkylcarbonyl, alkylsulfmylalkylcarbonyl, alkylsulfonylalkylcarbonyl, cyanoalkylcarbonyl, alkoxycarbonylalkylcarbonyl, aminocarbonylalkylcarbonyl, monalkylaminocarbonylalkylcarbonyl, dialkylaminocarbonylalkylcarbonyl, —CH═N—O—R11, amino(thio)carbonyl, monoalkylamino(thio)carbonyl, dialkylamino(thio)carbonyl, or a radical of the formula
- wherein:
- R13 is hydrogen, alkyl, or haloalkyl;
- Y and Z are O, S, SO, SO2, NH, N-alkyl, or N-acyl;
- Q is ethylene or propylene optionally substituted with alkyl, haloalkyl, alkoxy, alkoxyalkyl, cyano, hydroxyalkyl, amino, alkylamino, dialkylamino, alkylsulfenyl, alkylsulfmyl, alkylsulfonyl, OH, or SH;
- s is 0 to 3;
- R3 is alkyl, haloalkyl, hydroxyalkyl or alkoxyalkyl;
- R11 and R12 independently represent H, alkyl, haloalkyl, formyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfmyl, haloalkylsulfinyl, allyl, propargyl, halogen, alkoxyalkyl, alkylthioalkyl, alkylsulfmylalkyl, alkylsulfonylalkyl, haloalkoxyalkyl, haloalkylthioalkyl, haloalkylsulfmylalkyl, haloallylsulfonylalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylamninoalkyl, or alkoxycarbonyl;
- and
- n is 0, 1 or 2,
- provided that when R1 is methyl, then R2 is not hydrogen or alkyl, W is not —CO2R3 and n is not 0;
- and
- provided that when W is —CO2C2H5, then R is not —C(NH2)(═NH) or an acid addition salt thereof.
13 more elements
Dependencies are inferred from the claim text.