Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-03-05
2004-05-11
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S182000, C548S186000
Reexamination Certificate
active
06734198
ABSTRACT:
The present invention relates to novel trifiluorobutenes and their use as nematicides.
U.S. Pat. No. 3,518,172 describes trifluorobutenyl compounds which have nematicidal activity. Japanese Laid-open Patent Publication (PCT) No. 500037/1988(=WO 86/07590) also describes that some kinds of polyhaloalkene compounds have nematicidal activity. Further, WO 95/24403 describes that 4,4-difluorobutenyl compounds have nematicidal activity. Japanese Laid-open Patent Application No. 176141/1997 mentions thiazole derivatives having insecticidal and araricidal activity.
There have now been found novel trifluorobutenes of the formula (I)
in which
X represents halogen and
n represents 0, 1 or 2.
The compounds of the formula (I) in which n represents 0 can be obtained when trifluorobutenes of the formula (Ia)
are reacted with a halogenating agent, optionally in the presence of one or more inert diluents (process (A)).
The compounds of the formula (I) in which
n represents 1 or 2
can be obtained when compounds of the formula (Ib)
in which
X is the same as defined above
are reacted with an oxidizing agent, optionally in the presence of one or more inert diluents (process (B)).
The compounds of the formula (I) of the present invention have strong nematicidal activity and show good compatibility with various crops. According to the present invention the compounds of the formula (I) have surprisingly strong nematicidal activity compared with the known compounds described in the aforementioned literature.
In the present specification X preferably represents fluoro, chloro or bromo. X particularly preferably represents fluoro or chloro. X very particularly preferably represents chloro.
In the present specification n preferably represents 0 or 2. n particulary preferably represents 2.
Process (A) for preparing compounds of the formula (I) of the present invention can be represented by the following reaction scheme in which N-chlorosuccinimide is exemplaryly used as halogenating agent:
Process (B) for preparing compounds of the formula (I) of the present invention can be represented by the following reaction in which 5-chloro2-(3,4,4-trifluoro-3-butenylthio)thiazole is used as a starting material and m-chloroperoxybenzoic acid is exemplaryly used as oxidizing agent.
2-(3,4,4-trifluoro-3-butenylthio)thiazole is a known compound described in Japanese Laid-open Patent Publication (PCT) No. 500037/1988 (=WO 86/07590). Compounds of formula (Ib), which are used as starting material in process (B), correspond to the compounds of the formula (I) of the present invention in which n represents 0 and can be synthesized according to the aforementioned process (A).
Halogenating agents used in Process (A) can be agents usually used for this purpose in organic chemistry and which are known to a person skilled in the art, including for example sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, trichloro-isocyanuric acid, potassium fluoride, sodium chlorate, phosphorus pentachloride, titanium (IV) chloride, chlorine gas, bromine, iodine etc.
Oxidizing agents used for the oxidation of the above-mentioned compounds of the formula (Ib) in process (B) can be agents usually used for this purpose in organic chemistry and which are known to a person skilled in the art including for example hydrogen peroxide water, m-chloroperoxybenzoic acid, peroxyacetic acid, peroxy-benzoic acid, magnesium monoperoxyphthalate, potassium peroxymonosulfate, etc.
The reaction of the above-mentioned process (A) is preferably conducted in the presence of an adequate diluent. Diluents which can be used in this process can for example be water, aliphatic, alicyclic and aromatic hydrocarbons (which can be optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroine, benzene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene etc.; ethers, such as diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran etc.; nitrites, such as acetonitrile, propionitrile, acrylonitrile etc.; acid amides, such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone etc.; sulfones and sulfoxides, such as dimethyl sulfoxide, sulfolane etc.
The reaction temperatures of process (A) according to the invention can be varied over a relatively wide range. In general, temperatures in a range of between 0 and 200° C., preferably between 20 and 150° C. are employed. The process (A) according to the invention is generally carried out under normal pressure. However, it is possible to carry out the process (A) under elevated pressure or under reduced pressure, in general between 0.1 bar and 10 bar.
To carry out the process (A) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use one of the components in a relatively large excess. Work-up is carried out according to customary methods (cf. the preparation examples).
For example, the compound of the formula (I) in which n represents 0 and X represents chloro can be obtained by reacting 1-1.2 moles of N-chlorosuccinimide with 1 mole of 2-(3,4,4-trifluoro-3-butenylthio)thiazole in carbon tetrachloride under reflux by heating.
The reaction of the above-mentioned process (B) is preferably conducted in the presence of an adequate diluent. Diluents which can be used in this process can for example be water, aliphatic, alicyclic and aromatic hydrocarbons (which can be optionally chlorinated), such as hexane, cyclohexane, petroleum, ether, ligroine, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene etc.; ethers, such as diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran etc.; nitriles, such as acetonitrile, propionitrile, acrylonitrile etc.; alcohols, for example methanol, ethanol, isopropanol, butanol, ethylene glycol etc.; esters, for example ethyl acetate, amyl acetate etc.; acid amides, for example dimethyl-formamide, dimethylacetamide, N-methylpyrrolidone etc.; sulfones and sulfoxides, for example dimethyl sulfoxide, sulfolane etc.; carboxylic acids, for example formic acid, acetic acid etc.
The reaction temperatures of process (B) according to the invention can be varied over a relatively wide range: In general, temperatures in a range of between 0 and 150° C., preferably between 0 and 120° C. are employed. The process (B) according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process (B) under elevated pressure or under reduced pressure, in general between 0.1 bar and 10 bar.
To carry out the process (B) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use one of the components in a relatively large excess. Work-up is carried out according to customary methods (cf. the preparation examples).
For example, compounds of the formula (I) in which n represents 1 can be obtained by reacting, 1-2 moles of m-chloroperoxybenzoic acid with 1 mole of the compound of the formula (Ib) in methylene chloride under cooling with ice.
The compounds of the formula (I) according to the present invention show strong controlling activity against nematodes. They can, therefore, be efficiently used as nematicidal agents. The compounds of the formula (I) of the present invention do not exhibit phytotoxicity against crops and can be used for controlling harmful nematodes.
The compounds according to the invention can be used, for example, against nematodes such as Pratylenchus spp., Globodera spp., such as
Globodera rostochiensis wollenweber
, Heterodera spp., such as
Hetemodera glycines ichinohe
, Meloidogyne spp., Aphelenchoides spp., such as
Aphelenchoides basseyi christie, Radopholus similis, Ditylenchus dipsaci, Tyleachulus semipenetrans
, Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp., such as
Bursaphelenchus xylophilis
Abe Takahisa
Ishikawa Koichi
Otsu Yuichi
Shibuya Katsuhiko
Watanabe Yukiyoshi
Harmuth Raymon J.
Henderson Richard E. L.
Nihon Bayer Agrochem K.K.
Ramsuer Robert W.
Saeed Kamal
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