Pyrazole derivatives
The present invention relates to nitro-vinyl-pyrazole compounds of formula (B) wherein ring A, R B2 and R B3 are as defined in claim 1 , as well as the manufacture of such compounds and their subsequent use in the production of agrochemicals and/or pharmaceuticals.
1. A compound of formula (B)
wherein:
ring A is A1, A2, A3, or A5,
where the jagged line denotes attachment to the nitrovinyl moiety, R B2 is C 1 -C 3 alkyl or C 1 -C 3 fluoroalkyl, and R B3 and R B3SN are halogen, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, or C 1 -C 3 alkyl; or
ring A is A 4
where the jagged line denotes attachment to the nitrovinyl moiety, R B2 is C 1 -C 3 alkyl or C 1 -C 3 fluoroalkyl, and R B3 is fluoro, bromo, iodo, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, or C 1 -C 3 alkyl, or
ring A is A 4
where the jagged line denotes attachment to the nitrovinyl moiety, R B2 is ethyl, n-propyl, cyclopropyl, isopropyl, or C 1 -C 3 fluoroalkyl, and R B3 is halogen, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, or C 1 -C 3 alkyl.
2. The compound of claim 1 , wherein ring A is A1, A2, A3, or A5.
3. The compound of claim 2 , wherein R B2 is selected from the group consisting of methyl, ethyl, n-propyl, fluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl and trifluoroethyl.
4. The compound of claim 2 , wherein R B3 and R B3SN are selected from the group consisting of chloro, fluoro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl C 1 -C 3 haloalkoxy, and C 1 -C 3 alkoxy.
5. The compound of claim 1 , wherein said compound is selected from the group consisting of B.001, B.002, B.003, B.004, B.005 and B.006 as shown in the table below
Cmpd.
No.
Name
Structure
B.001
(E)-N,N-dihydroxy-2-[1-methyl-5- (trifluoromethyl)pyrazol-3-yl]ethenamine
B.002
(E)-N,N-dihydroxy-2-[1-methyl-5- (trifluoromethyl)pyrazol-4-yl]ethenamine
B.003
(E)-2-(5-chloro-1-methyl-pyrazol-3-yl)-N,N- dihydroxy-ethenamine
B.004
(E)-2-(5-chloro-1-methyl-pyrazol-4-yl)-N,N- dihydroxy-ethenamine
B.005
(E)-2-(5-fluoro-1-methyl-pyrazol-3-yl)-N,N- dihydroxy-ethenamine
B.006
(E)-2-(5-fluoro-1-methyl-pyrazol-4-yl)-N,N- dihydroxy-ethenamine
6. The compound of claim 1 , wherein the compound is
7. The compound of claim 1 , wherein the compound is
8. The compound of claim 1 , wherein the compound is
9. The compound of claim 1 , wherein the compound is
10. The compound of claim 1 , wherein the compound is
11. The compound of claim 1 , wherein the compound is
12. The compound of claim 4 , wherein R B3 and R B3SN are selected from the group consisting of chloro, fluoro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl C 1 -C 3 haloalkoxy, and C 1 -C 3 alkoxy.
13. The compound of claim 2 , wherein R B2 is methyl.
14. The compound of claim 2 , wherein R B3 and R B3SN are selected from the group consisting fluoro, chloro, and trifluoromethyl.
15. The compound of claim 14 , wherein R B2 is methyl.
16. The compound of claim 2 , wherein R B2 is C 1 -C 3 fluoroalkyl, and R B3 and R B3SN are C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, or C 1 -C 3 alkyl.
17. The compound of claim 2 , wherein R B3 and R B3SN are C 1 -C 3 fluoroalkyl.