Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-07-24
2001-11-13
Solola, T. A. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S145000, C424S409000, CD16S233000
Reexamination Certificate
active
06316477
ABSTRACT:
TECHNICAL FIELD
The present invention relates to new 1-arylpyrazole derivatives or their salts, their productions and agrochemical compositions containing the same.
BACKGROUND ART
Although various synthesized compounds having inhibitory actions against harmful pests have hitherto been used as insecticides, almost all of them belong to organic phosphate esters, carbamic esters, organic chlorine-containing compounds or pyrethroid compounds.
On the other hand, it has been reported that 1-arylpyrazole derivatives, wherein the 3-position of a pyrazole ring is a hydrogen atom, an alkyl group, a cycloalkyl group, a halogenoalkyl group, a cyano group, a nitro group, a halogen atom, a carbamoyl group or a thiocarbamoyl group have an insecticidal activity (U.S. Pat. No. 5,232,940 corresponding to JP-A 228065/1987, U.S. Pat. No. 4,771,066 corresponding to JP-A 207259/1987, U.S. Pat. No. 5,236,938 corresponding to JP-A 148240/1993, EP-A 385809, U.S. Pat. No. 5,306,694 and WO93/06089).
These pyrazole derivatives have insecticidal actions, however, they have high toxicities to human beings, domestic animals and fish. Sometimes, the pyrazole derivatives exhibit toxicity to natural enemies of pests, and a high residual property in soil or the like. Therefore, a satisfactory effect is not actually obtained at present.
In order to solve the above problems, the present inventors have intensively studied for a long time so as to find out an insecticide having a structure which is quite different from that of an insecticide which has hitherto been used. As a result, it has been unexpectedly found that a novel pyrazole derivative or a salt thereof has a very strong insecticidal activity. It has also been found that the pyrazole derivative or a salt thereof is safe because it causes little chemical damage to plants and it's toxicity to human being, domestic animals, fish, natural enemies of pests, etc. is low. Furthermore, the present inventors have intensively studied based on these findings and completed the present invention.
DISCLOSURE OF INVENTION
The present invention relates to:
(1) a compound of the formula:
wherein Ar is an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group, R is H, a halogen or a group bonded through C, N, O, S or P, W is a halogen or a group bonded through C, N, O, S or P, X is H or a group bonded through C, N, O or S, Y is H or a group bonded through C, N, O, S or P, or X and Y being combined, a group of the formula
is an optionally substituted nitrogen-containing heterocyclic group which may further have N, O, S and/or P as a ring-constituting atom, or a salt thereof,
(2) a process for producing the compound as defined in (1) or a salt thereof which comprises
(i) reacting a compound of the formula:
wherein the symbols are as defined above, or a salt thereof with a compound of the formula:
Q—NH
2
wherein Q is a group bonded through C, N, O, S or P, to produce a compound of the formula:
wherein the symbols are as defined above, or a salt thereof, or
(ii) reacting a compound of the formula:
wherein Ar and W are as defined above, J is O or —NR
16
(R
16
is H or a group bonded through C), or a salt thereof with a compound of the formula:
R
17
C(OR
18
)
3
wherein R
17
is H or a C
1-6
alkyl group, R
18
is a C
1-6
alkyl group, to produce a compound of the formula:
wherein the symbols are as defined above, or a salt thereof, or
(iii) oxdizing a compound of the formula:
wherein Ar, R and Q are as defined above, R
6
is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, or a salt thereof, to produce a compound of the formula:
wherein n′ is 1 or 2, the other symbols are as defined above, or a salt thereof, or
(iv) reacting a compound of the formula:
wherein the symbols are as defined above, or a salt thereof with a compound of the formula:
Y—NH
2
wherein Y is as defined above, or a salt thereof, to produce a compound of (1) or a salt thereof. (3) an agrochemical composition which comprises an effective amount of the compound as defined in (1) or a salt thereof, and (4) use of the compound of (1) or a salt thereof in the preparation of an insecticidal composition, etc.
The compound of the above formula [I] or a salt thereof of the present invention sometimes have geometrical isomers and/or stereoisomers, and the present invention includes all of these isomers.
In the above formulae, Ar is an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group.
Examples of the aromatic hydrocarbon group in the optionally substituted aromatic hydrocarbon group for Ar include a C
6-14
aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, anthryl, phenanthryl and the like.
Examples of the substituent on the aromatic hydrocarbon group include a C
1-6
alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, n-hexyl), which may optionally be substituted with 1 to 4 substituents selected from the group consisting of, for example, hydroxy, C
1-6
alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, etc.), halogen (e.g. fluorine, chlorine, bromine, iodine, etc.) and amino which may optionally be mono- or di-substituted with C
1-6
alkyl (e.g. methylamino, ethylamino, propylamino, dimethylamino, diethylamino, etc.); an amino group which may optionally be mono- or di-substituted with C
1-6
alkyl or C
1-6
alkanoyl (e.g. methylamino, ethylamino, propylamino, dimethylamino, diethylamino, acetylamino, propionylamino, etc.); a hydroxyl group; a carboxyl group; a nitro group; SF
5
; a C
1-6
alkoxy group (the same as defined above); a C
1-6
alkanoyloxy group (e.g. formyloxy, acetyloxy, propionyloxy, n-butyryloxy, iso-butyryloxy, etc.); a cyano group; and a halogen atom (the same as defined above).
The number of substituents is from 1 to 6, preferably from 1 to 4, most preferably from 1 to 3, within the substitutable range. When the substituent is halogen atom, substitution may be performed within the maximum substitutable range.
As the aromatic heterocyclic group in the optionally substituted aromatic heterocyclic group for Ar, for example, 5- to 8-membered aromatic heterocyclic groups having 1 to 4 hetero atoms selected from O, S, N, etc., in addition to carbon atom(s), which may be condensed with a C
5-10
cyclic hydrocarbon ring (e.g. cyclopentane, cyclohexane, benzene, naphthalene, etc.) or 5- or 6-membered heterocyclic ring having 1 to 4 hetero atoms selected from N, O and S may be used.
Specifically, 5-membered aromatic heterocyclic group having 1 to 4 hetero atoms selected from O, S, N, etc., in addition to carbon atom(s), (e.g. 2- or 3-thienyl, 2- or 3-furyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl, 3-, 4- or 5-isoxazolyl, 3-, 4- or 5-isothiazolyl, 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, etc.); 6-membered aromatic heterocyclic group having 1 to 4 hetero atoms selected from O, S, N, etc., in addition to carbon atom(s), (e.g. 2-, 3- or 4-pyridyl or N-oxide thereof, 2-, 4- or 5-pyrimidinyl or N-oxide thereof, 3 or 4-pyridazinyl or N-oxide thereof, pyrazinyl, etc.); and dicyclic or tricyclic condensed aromatic heterocyclic group having 1 to 4 hetero atoms selected from O, S, N, etc., in addition to carbon atom(s), (e.g. benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo[1,5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, imidazo[1,2-a]pyridinyl, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolidinyl, quinolidinyl, 1,8-naphthylidinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc.) are used.
As the substituent on the aromatic heterocyclic group, for example, the same substituent as that of the aromatic hydrocarbon group for Ar are used. The number
Akayama Atsuo
Kando Yasuyuki
Kiji Toshiyuki
Noguchi Makoto
Solola T. A.
Takeda Chemical Industries Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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