Pesticidal arylpyrrolidines
View Patent ↗The invention is directed to arylpyrrolidines compounds which exhibit excellent insecticidal efficacy and which may be used as in the agrochemical field or in the field of veterinary medicine. The compounds are represented by formula (I): wherein the respective substituents are defined in the specification.
1. An arylpyrrolidine compound having the formula
or a salt thereof,
wherein
A 1 represents C—Y 2-4 or nitrogen
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen or C 1-4 haloalkyl;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -haloalkoxy, C 3-6 -cycloalkyl, C 1-4 -haloalkyl, C 1-4 -alkylsulfanyl, or C 1-4 -haloalkylsulfanyl;
R 3 and R 4 each independently represents hydrogen or methyl;
R 5-1 represents hydrogen or methyl; and
R 6-1 represents C 2-5 alkylcarbonyl, (total carbon atom number) C 2-3 haloalkylcarbonyl, (total carbon atom number) C 2-3 alkylaminocarbonyl, (total carbon atom number) C 4-5 cycloalkylcarbonyl, C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, (total carbon atom number) C 4-7 cycloalkylaminocarbonyl, cyclobutylcarbamoyl, C 1-4 alkoxy(C 1-4 )alkylcarbonyl, 3-methoxypropanoyl, C 1-2 alkyl-S(C 1-2 )alkylcarbonyl, C 1-2 alkyl-SO(C 1-2 )alkylcarbonyl, or C 1-2 alkyl-SO 2 (C 1-2 )alkylcarbonyl.
2. The compound of claim 1 , wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen, CF 3 , CF 2 H, CFH 2 , CH 2 CF 3 , or CF 2 CF 3 ;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, OCF 3 , CF 3 , CF 2 H, CFH 2 , CH 2 CF 3 , or CF 2 CF 3 ;
R 3 and R 4 each independently represents hydrogen;
R 5-1 represents hydrogen or methyl; and
R 6-1 represents acetyl, propionyl, n-propylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, difluoroacetyl, 3,3,3-trifluoropropanoyl, ethylcarbamoyl, propylcarbamoyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopropylacetyl, cyclopropylcarbamoyl,
3. The compound of claim 1 , wherein the compound is selected from the group consisting of Compound Nos. 1-88, 1-258, 1-304, 1-307, 1-448, 1-488, 1-496, 1-589, 1-677, 1-687, 1-1279, 1-1472, 8-102, and 8-118.
4. The compound of claim 3 , wherein the compound is selected from the group consisting of Compound Nos. 1-88, 1-258, 1-304, 1-307, 1-448, 1-488, 1-496, 1-589, 1-677, 1-687, 1-1279, and 1-1472.
5. The compound of claim 3 , wherein the compound is selected from the group consisting of Compound Nos. 1-258, 1-307, 1-448, 1-677, 1-687, and 1-1279.
6. The compound of claim 3 , wherein the compound is Compound No. 1-677 or 1-687.
7. The compound of claim 3 , wherein the compound is Compound No. 8-102 or 8-118.
8. The compound of claim 7 , wherein the compound is Compound No. 8-102.
9. An arylpyrrolidine compound having the formula
or a salt thereof,
wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen or C 1-4 haloalkyl;
Y 2-3 and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -haloalkoxy, C 3-6 -cycloalkyl, C 1-4 -haloalkyl, C 114 -alkylsulfanyl, or C 1-4 -haloalkylsulfanyl;
R 3 and R 4 independently of each other represents hydrogen or methyl;
R 5-1 represents hydrogen or methyl; and
R 6-1 represents C 2-5 alkylcarbonyl, (total carbon atom number) C 2-3 haloalkylcarbonyl, (total carbon atom number) C 2-3 alkylaminocarbonyl, (total carbon atom number) C 4-5 cycloalkylcarbonyl, C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, (total carbon atom number) C 4-7 cycloalkylaminocarbonyl, cyclobutylcarbamoyl, C 1-4 alkoxy(C 1-4 )alkylcarbonyl, 3-methoxypropanoyl, C 1-2 alkyl-S(C 1-2 )alkylcarbonyl, C 1-2 alkyl-SO(C 1-2 )alkylcarbonyl, or C 1-2 alkyl-SO 2 (C 1-2 )alkylcarbonyl.
10. The arylpyrrolidine compound of claim 9 , wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen, CF 3 , CF 2 H, CFH 2 , CH 2 CF 3 , or CF 2 CF 3 ;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, OCF 3 , CF 3 , CF 2 H, CFH 2 , CH 2 CF 3 , or CF 2 CF 3 ;
R 3 and R 4 each independently represents hydrogen;
R 5-1 represents hydrogen or methyl; and
R 6-1 represents acetyl, propionyl, n-propylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, difluoroacetyl, 3,3,3-trifluoropropanoyl, ethylcarbamoyl, propylcarbamoyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopropylacetyl, cyclopropylcarbamoyl,