Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-09-05
2004-06-01
Desai, R (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S229000, C548S230000
Reexamination Certificate
active
06743814
ABSTRACT:
The present invention relates to novel trifluorobutenes, processes for their preparation and their use as a nematicidal agent.
Japanese Laid-open Patent Publication No. 85267/1990 describes substituted azolethioethers which have insecticidal activity. U.S. Pat. No. 3,513,172 describes that some kinds of trifluorobutenyl compounds have nematicidal activity and Japanese Laid-open Patent Publication (PCT) No. 500037/1988 describes that some kinds of polyhaloalkene compounds have nematicidal activities. Further, WO 95/24403 describes that 4,4-difluorobutenyl compounds have nematicidal activity.
There have now been found novel trifluorobutenes of formula (I)
wherein
R
1
represents hydrogen, halogen, or alkyl which may be unsubstituted or substituted with halogen, hydroxy, alkoxy, alkylthio, alkylcarbonyloxy, haloalkylcarbonyloxy or cyano, or represents alkylsulfonyloxy or represents phenyl which may be unsubstituted or substituted with halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl, haloalkoxy, haloalkylthio, phenyl, phenoxy, cyano or nitro.
R
2
represents hydrogen, halogen, or alkyl which may be unsubstituted or substituted with alkoxy or halogen, or represents alkoxycarbonyl, and
n represents 0, 1 or 2.
provided that if R
1
represents alkyl, R
2
does not represent halogen.
In the definitions, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branched. Substituents may be identical or different.
Preferred substituents or preferred ranges of the radicals present in the formulae listed above and below are defined below.
R
1
preferably represents hydrogen or halogen, or represents C
1-6
alkyl which may be unsubstituted or substituted with halogen, hydroxy, C
1-3
alkoxy, C
1-3
alkylthio, C
1-3
alkylcarbonyloxy, trifluoromethylcarbonyloxy or cyano, or represents C
1-4
alkylsulfonyloxy or represents phenyl which may be unsubstituted or substituted with halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy, cyano or nitro.
R
2
preferably represents hydrogen or halogen or represents C
1-6
alkyl which may be unsubstituted or substituted with C
1-3
alkoxy or halogen, or represents C
1-4
alkoxycarbonyl.
n preferably represents 0 or 2.
R
1
particularly preferably represents hydrogen, fluoro, chloro or bromo, or represents C
1-4
alkyl which may be unsubstituted or substituted with fluoro, chloro, bromo, hydroxy, C
1-3
alkoxy, C
1-3
alkoxy, C
1-3
alkylthio, C
1-3
alkylcarbonyloxy, trifluoromethylcarbonyloxy or cyano, or represents methylsulfonyloxy or ethylsulfonyloxy or represents phenyl which may be unsubstituted or substituted with fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy, cyano or nitro.
R
2
particularly preferably represents hydrogen, fluoro, chloro or bromo or represents C
1-4
alkyl which may be unsubstituted or substituted with C
1-3
alkoxy or bromo or represents C
1-3
alkoxycarbonyl.
n particularly preferably represents 0.
The novel compounds of the above-mentioned formula (I) are obtained, for example, by the following preparation processes a), b), c), d), e), f), g) or h).
Preparation Process a)
Compounds of the formula (I)
wherein
R
1
represents hydrogen, represents alkyl which may be substituted with halogen, hydroxy, alkoxy, alkylthio, alkylcarbonyloxy, haloalkylcarbonyloxy or cyano or represents phenyl which may be substituted with halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl, haloalkoxy, haloalkylthio, phenyl, phenoxy, cyano or nitro,
R
2
represents hydrogen or represents alkyl which may be substituted with alkoxy or halogen and
n represents 0
are obtained when compounds of the formula (II)
wherein
R
1a
represents hydrogen, represents alkyl which may be substituted with halogen, hydroxy, alkoxy, alkylthio, alkylcarbonyloxy, haloalkylcarbonyloxy or cyano or represents phenyl which may be substituted with halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl, haloalkoxy, haloalkylthio, phenyl, phenoxy, cyano or nitro,
R
2a
represents hydrogen or represents alkyl which may be substituted with alkoxy or halogen and
n represents 0
are reacted with 4-bromo-1,1,2-trifluoro-1-butene in the presence of inert solvents and if appropriate, in the presence of an acid binder.
Preparation Process b)
Compounds of the formula (I)
wherein
R
1
and R
2
are as defined above, and
n represents 1 or 2
are obtained when compounds of the formula (Ia)
wherein
R
1
and R
2
are as defined above
are oxidized in the presence of inert solvents.
Preparation Process c)
Compounds of the formula (I)
wherein
R
1
represents hydrogen or haloalkyl,
R
2
represents halogen, and
n represents 0
are obtained when compounds of the formula (Ib)
wherein
R
1b
represents hydrogen or alkyl, and
R
2b
represents hydrogen
are reacted with a halogenating agent in the presence of inert solvents.
Preparation Process d)
Compounds of the formula (I)
wherein
R
1
represents haloalkyl,
R
2
represents hydrogen or haloalkyl and
n represents 0
are obtained when compounds of the formula (Ic)
wherein
R
1c
represents alkyl, and
R
2c
represents hydrogen or alkyl,
are reacted with a halogenating agent in the presence of inert solvents.
Preparation Process e)
Compounds of the formula (I)
wherein
R
1
represents halogen,
R
2
represents hydrogen or alkyl and
n represents 0,
are obtained when compounds of the formula (III)
wherein
R
2d
represents hydrogen or alkyl,
are reacted with a halogenating agent in the presence of inert solvents, and, if appropriate, in the presence of an organic base.
Preparation Process f)
Compounds of the formula (I)
wherein
R
1
represents alkylsulfonyloxy,
R
2
represents hydrogen or alkyl and
n represents 0
are obtained when compounds of the aforementioned formula (III) are reacted with compounds of the formula
R
1d
SO
2
Cl (IV)
wherein
R
1d
represents alkyl
in the presence of inert solvents, and if appropriate, in the presence of an inorganic or organic base.
Preparation Process g)
Compounds of the formula (I)
wherein
R
1
represents alkyl,
R
2
represents alkoxycarbonyl and
n represents 0
are obtained when compounds of the formula (IV)
wherein
R
1c
is as defined above, and
R
3
represents alkyl,
are reacted with thiourea and the products are then reacted with 4-bromo-1,1,2-trifluoro-1-butene in the presence of inert solvents.
Preparation Process h)
Compounds of the formula (I)
wherein
R
1
represents hydrogen,
R
2
represents alkoxyalkyl and
n represents 0
are obtained when compounds of the formula (Id)
wherein
R
1e
represents hydrogen,
are reacted with compounds of the formula (VI)
R
4
—Br (VI)
wherein
R
4
represents alkoxyalkyl,
in the presence of inert solvents.
The compounds of the formula (I) of the present invention exhibit strong nematicidal activity and show good compatibility with various crops.
The compounds of the formula (I) according to the present invention surprisingly show a very outstanding nematicidal activity compared with the compounds described in the aforementioned literature which are similar to the compounds of the present invention.
In the present specification “halogen” represents fluoro, chloro, bromo or iodo, preferably represents fluoro, chloro or bromo, and particularly preferably represents chloro or bromo.
“Alkyl” and each alkyl part of “alkoxy”, “alkylthio”, “alkylcarbonyloxy”, “alkylsulfonyloxy” and “alkoxycarbonyl” represents a straight-chain or branched-chain alkyl such as methyl, ethyl, n- or i-propyl, n-, i-, s- or -t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, n-pentyl or n-hexyl and particularly preferably represents methyl, ethyl, n- or i-propyl or n-, i-, s-, or t-butyl.
“Haloalkyl” and each haloalkyl part of “haloalkylcarbonyloxy”, “haloalkoxy” and “haloalkylthio” represents alkyl substituted with at least one halogen, preferably represents C
1-4
alkyl substituted with one or a plurality of halogen,
Gomibuchi Takuya
Ishikawa Koichi
Narabu Shin-ichi
Otsu Yuichi
Shibuya Katsuhiko
Desai R
Henderson Richard E. L.
Nihon Bayer Agrochem K.K.
Shiao Robert
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