Insecticidal arylpyrrolines
View Patent ↗The invention relates to novel arylpyrroline compounds of formula (I) which have excellent insecticidal activity and which can thus be used as an insecticide.
1. A arylpyrroline compound of formula (I)
wherein
Q stands for a 2-pyridyl group, a 3-pyridyl group, or a 4-pyridyl group, each group may be substituted with at least one substituent X or X 1 ;
X and X 1 each independently stand for fluorine, chlorine, bromine, iodine, C 1-12 haloalkyl, nitro, C 1-12 alkyl, or C 1-12 alkoxyl, cyano, C 1-12 haloalkoxyl, C 1-12 alkylsulfenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylsulfenyl, C 1-12 haloalkylsulfinyl, or C 1-12 haloalkylsulfonyl, hydroxyl, thiol, amino, C 1-12 acylamino, C 1-12 alkoxy-carbonylamiho, C 1-12 haloalkoxycarbonylamino, C 1-12 alkoxyimino, C 1-12 haloalkoxyimino, or C 1-12 alkylsulfonylamino, or sulfur pentafluoride;
A 1 , A 2 , A 3 and A 4 each independently stand for a carbon atom which may be substituted by a substituent Y, and whereas two adjacent substituents Y together with the carbon atoms to which they are attached may form a 5- or 6-membered aromatic ring, or
A 1 A 2 A 3 and A 4 each independently stand for a nitrogen atom, under the proviso that only 2 of the chemical groups A 1 , A 2 , A 3 and A 4 stand at the same time for nitrogen;
Y stands for fluorine, chlorine, bromine, iodine, C 1-12 haloalkyl, nitro, C 1-12 alkyl, C 3-8 cycloalkyl, C 3-8 cyclohaloalkyl, C 1-12 alkoxyl, cyano, C 1-12 haloalkoxyl, C 1-12 alkylsulfenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylsulfenyl, C 1-12 haloalkylsulfinyl, C 1-12 haloalkylsulfonyl, C 1-12 alkylsulfonyloxy, C 1-12 haloalkylsulfonyloxy, C 1-12 alkylaminosulfonyl, C 1-12 haloalkylaminosulfonyl, di(C 1-12 )alkylaminosulfonyl, or di((C 1-12 )haloalkyl)aminosulfonyl, hydroxyl, thiol, amino, C 1-12 alkylamino, di(C 1-12 )alkylamino, C 1-12 acylamino, C 1-12 alkoxycarbonylamino, C 1-12 haloalkoxycarbonylamino, C 1-12 alkylsulfonylamino, C 1-12 haloalkylsulfonylamino, C 1-12 trialkylsilyl, C 1-12 alkoxyimino, C 1-12 haloalkoxyimino, C 1-12 alkoxyiminoalkyl, C 1-12 haloalkoxyimino(C 1-12 )alkyl, C 1-12 alkylsulfinylimino, C 1-12 alkylsulfinylimino(C 1-12 )alkyl, C 1-12 alkylsulfinylimino(C 1-12 )alkylcarbonyl, C 1-12 alkylsulfoxyimino, C 1-12 alkylsulfoxyimino(C 1-12 )alkyl, C 1-12 alkoxycarbonyl, C 1-12 alkylcarbonyl, aminocarbonyl, C 1-12 alkylaminocarbonyl, aminothiocarbonyl, C 1-12 alkylaminothiocarbonyl, di(C 1-12 )alkylaminocarbonyl, or di(C 1-12 )alkylaminothiocarbonyl;
G stands for a heterocyclic group G1 to G9 having the following formula
which may be substituted by a substituent Z which is selected from the group consisting of fluorine, chlorine, bromine, iodine, C 1-6 haloalkyl, nitro, C 1-6 alkoxy, cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, hydroxyl and thiol,
or represents a chemical group G10 characterized by the following formula:
wherein R 1 and R 2 each independently stand for hydrogen, C 1-12 alkyl, C 3-8 cycloalkyl, C 1-12 haloalkyl, C 3-8 cyclohaloalkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 2-12 haloalkenyl, cyano, C 1-12 alkoxycarbonyl, or C 1-12 , alkoxythiocarbonyl, or R 1 and R 2 , together with the carbon atom to which they are attached, form a 3 to 6-membered carbocyclic ring;
R 3 represents hydrogen, amino, hydroxyl, C 1-12 alkoxy, C 1-12 alkylcarbonylamino, C 1-12 alkylimino, C 1-12 alkyl, C 3-8 cycloalkyl, C 1-12 haloalkyl, cyano, C 2-12 alkenyl, C 2-12 alkynyl, or C 1-12 alkylcarbonyl, or is selected from the group consisting of CH 2 —R 5 ,C(═O)R 5 , C(═S)R 5 ,
R 4 represents a chemical group selected from the group consisting of hydrogen, cyano, carbonyl, thiocarbonyl, C 1-12 alkylcarbonyl, C 1-12 alkylthiocarbonyl, C 1-12 haloalkylcarbony , C 1-12 haloalkylthiocarbonyl, C 1-12 alkylaminocarbonyl, C 1-12 alkylaminothiocarbonyl, di(C 1-12 )alkylaminocarbonyl, di(C 1-12 )alkylanrinothiocarbonyl, C 1-12 alkoxyaminocarbonyl, C 1-12 alkoxyaminothiocarbonyl, C 1-12 alkoxycarbonyl, C 1-12 alkoxythiocarbonyl, C 1-12 thioalkoxycarbonyl, C 1-12 thioalkoxythiocarbonyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylsulfonyl, C 3-8 cycloalkylcarbonyl, C 2-12 alkenylcarbonyl, C 2-12 alkynylcarbonyl, C 3-8 cycloalkyl-(C 1-12 )alkylcarbonyl, C 1-12 alkylsulfenyl(C 1-12 )alkylcarbonyl, C 1-12 alkylsulfinyl(C 1-12 )alkylcarbonyl, C 1-12 alkylsulfonyl(C 1-12 )alkylcarbonyl, C 1-12 alkylcarbonyl(C 1-12 )alkylcarbonyl, C 3-8 cyclalkylaminocarbonyl, C 2-12 alkenylaminocarbonyl, C 2-12 alkynylaminocarbonyl, and C 1-12 alkoxy(C 1-12 )alkyl, or is selected from the group consisting of C(═O)R 5 and C(═S)R 5 , or
R 3 and R 4 , together with the nitrogen atom to which they are bound, form a 3- to 6-membered heterocyclic ring which may be substituted with a substituent X or X 1 , or may be substituted with a keto, thioketo or nitroimino group; and
R 5 represents optionally substituted phenyl, or an optionally substituted heterocyclic ring.
2. The arylprroline compound of claim 1 , wherein in formula (I) the grouping
stands for a grouping P1 to P4
wherein Y is as defined in claim, and k stands for 0, 1, 2, 3 or 4.
3. A composition comprising at least one compound of claim 1 for controlling animal pests.
4. A method for controlling animal pests comprising applying at least one compound of claim 1 to animal pests, their habitat, or both.
5. A method for treating a seed against insects comprising applying at least one compound of claim 1 to the seed.
6. The method of claim 5 , wherein the seed is a seed of a conventional plant.
7. The method of claim 5 , wherein the seed is a seed of a transgenic plant.
8. The compound of claim 1 , wherein the G stands for any one of G1 to G9 as defined in claim 1 .