US 6,310,049 B1 · Nematicidal pyrazoles

Abstract

Novel pyrazoles of formula (1) wherein R1 represents halogen, C1-6 alkyl, C1-5 haloalkyl, C2-6 alkoxy, C1-4 alkylthio, C2-5 alkenyloxy, C3-5 alkynyloxy, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C1-5 haloalkoxy, C2-6 (total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl, R2 represents hydrogen, halogen, C1-5 alkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C2-6 (total carbon number) alkylsulfinylalkyl, C2-6 (total carbon number alkylsulfonylalkyl or C1-5 haloalkyl, R3 represents hydrogen, C1-5 alkyl, —COR4, COOR5, CH(OR6)2 or CH2Si(R7)3, R4 represents C1-10 alkyl, C1-6 haloalkyl, C2-6 alkenyl, optionally substituted C3-6 cycloalkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number alkylthioalkyl, optionally substituted phenyl, C1-6 haloalkyl, alkylamino, di-(C1-6 alkyl)amino or optionally substituted phenylamino, R5 represents C1-7 alkyl, R6 and R7 represent C1-6 alkyl, and n is 1, 2 or 3, and when n is 2 or 3, the corresponding number (n) of R1 radicals may be the same or different, processes for preparing these compounds and their use as nematicides and anthelmintics.

Claims14

Dependent claims

A compound of the formula (I)

wherein
R1 represents halogen, C1-6 alkyl, C1-5 haloalkyl, C2-6 alkoxy, C1-4 alkylthio, C2-5 alkenyloxy, C3-5 alkenyloxy, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C1-5 haloalkoxy, C2-6 (total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl,
R2 represents hydrogen, halogen, C1-5 alkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C2-6 (total carbon number) alkylsulfinylalkyl, C2-6 (total carbon number) alkylsulfonylalkyl or C1-5 haloalkyl,
R3 represents hydrogen, C1-5 alkyl, —COR4,COOR5, CH(OR6)2 or CH2Si(R7)3,
R4 represents C1-10 alkyl, C1-6 haloalkyl, C2-6 alkenyl, optionally substituted C3-6 cycloalkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, optionally substituted phenyl, C1-5 alkylamino, di-(C1-6 alkyl)amino or optionally substituted phenylamino,
R5 represents C1-7 alkyl,
R6 and R7 represent C1-6 alkyl, and
n is 1, 2 or 3, and when n is 2 or 3, the corresponding number (n) of R1 radicals may be the same or different
with the proviso that 2-[5-(2-thienyl)-1H-pyrzaol-3-yl]-phenol is excluded.

6 more elements

A process for the preparation of the compounds of the formula (I)

wherein
R1 represents halogen, C1-6 alkyl, C1-5 haloalkyl, C2-6 alkoxy, C1-4 alkylthio, C2-5 alkenyloxy, C3-5, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C1-5 haloalkoxy, C2-6 (total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl,
R2 represents hydrogen, halogen, C1-5 alkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C2-6 (total carbon number) alkylsulfinylalkyl, C2-6 (total carbon number) alkylsulfonylalkyl or C1-5 haloalkyl,
R3 represents hydrogen, C1-5 alkyl, —COR4,COOR5, CH(OR6)2 or CH2Si(R7)3,
R4 represents C1-10 alkyl, C1-6 haloalkyl, C2-6 alkenyl, optionally substituted C3-6 cycloalkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, optionally substituted phenyl, C1-5 alkylamino, di-(C1-6 alkyl)amino or optionally substituted phenylamino,
R5 represents C1-7 alkyl,
R6 and R7 represent C1-6 alkyl, and
n is 1, 2 or 3, and when n is 2 or 3, the corresponding number (n) of R1 radicals may be the same or different,
wherein,
a) when R3 is hydrogen:
compounds of the formula
wherein R1 and n are as defined above, are reacted with a compound of the formula
NH2—NH2 (III)
in the presence of suitable diluent, or
b) when R3 is hydrogen:
compounds of the formula
wherein R1, R2 and n are as defined above, are reacted with the aforementioned compound of the formula (Ill) in the presence of suitable diluent, or
c) when R3 is a radical as defined above but other than hydrogen
compounds of formula
wherein R1, R2 and n are as defined above, are reacted with the compounds of the formula
R3—X (VI)
wherein R3 is a radical as defined above but other than hydrogen, and X is halogen,
in the presence of suitable diluent, and or
d) compounds of the formula
wherein R1, R2, R3 and n are as defined above, are oxidized, or
e) when R2 is alkylsulfinylalkyl or alkylsulfonylalkyl
compounds of the formula
wherein R1, R3 and n are as defined above, p is 1, 2 or 3, q is 1, 2, 3, 4 or 5, and 2≦p+q≦6, are oxidized.

25 more elements

Dependencies are inferred from the claim text.

Nematicidal pyrazoles

Life of this patent

Nematicidal pyrazoles

Life of this patent

Abstract

Claims14