Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-09
2001-11-06
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S357000, C546S290000, C546S304000
Reexamination Certificate
active
06313150
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel &agr;-substituted phenylacetic acid derivative, a process for producing it, and an agricultural fungicide containing it as an active ingredient.
BACKGROUND OF THE INVENTION
Certain kinds of &agr;-substituted phenyl acetic acid ester derivatives have been disclosed in JP-A 60-54949 and DE2742065. However, each of these compounds has a substituent at the 3-position of the phenyl group, and no compounds having a substituent at the 2-position have been disclosed. JP-A 3-17052 and JP-A 3-157350 also disclose &agr;-substituted phenylacetic acid ester derivatives. However, they only disclose 2-hydroxy-2-phenylacetic acid or its acetic acid ester as an intermediate or insecticide, and do not disclose its fungicidal activity at all.
JP-A 4-288045, JP-A 4-261147, WO93/15046, EP-A-498396, JP-A 3-169842, EP-A-532022, JP-A 7-17930, and EP-A-619301 also disclose related compounds.
The present invention is to provide a novel compound having potent fungicidal activity, a process for producing it, and an agricultural fungicide containing it as an active ingredient.
DISCLOSURE OF THE INVENTION
Under these circumstances, the present inventors have intensively studied to obtain compounds having potent fungicidal activity. As a result, it has been found that a novel &agr;-substituted phenylacetic acid derivative having a substituent at the 2-position in the phenyl group has potent fungicidal activity. Thus, the present invention has been completed.
The present invention provides:
1. A compound of the formula (I):
wherein R
1
is a halogen atom, optionally substituted alkyl, optionally substituted hydroxyl, alkylthio, alkylsulfinyl, alkylsulfonyl, optionally substituted amino or nitro; Q is optionally substituted aryl, an optionally substituted heterocyclic group, mono- or di-substituted methyleneamino, optionally substituted (substituted imino)methyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted carbonyl or substituted sulfonyl; X is a hydrogen atom, halogen atom, optionally substituted alkyl or optionally substituted hydroxyl; Y is optionally substituted hydroxyl, alkylthio or optionally substituted amino, provided that, when R
1
is hydroxyl, Y is not alkoxy; Z is an oxygen atom or sulfur atom; M is an oxygen atom, S(O)
i
(in which i is 0, 1 or 2), NR
2
(in which R
2
is a hydrogen atom, alkyl or acyl) or a single bond; and n is 0, 1 or 2; or a salt thereof;
2. A compound according to the above item 1, wherein R
1
is a halogen atom, alkyl, haloalkyl, alkoxyalkyl, hydroxyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, (alkylthio)carbonyloxy, alkylsulfonyloxy, arylsulfonyloxy, mono-or di-alkyl-substituted carbamoyloxy, aryloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, amino optionally substituted by alkyl, nitro or tetrahydropyranyloxy, or a salt thereof;
3. A compound according to the above item 1, wherein R
1
is alkoxy, or a salt thereof;
4. A compound according to the above item 1, wherein R
1
is methoxy, or a salt thereof;
5. A compound according to the above item 1, wherein Q is a group of the formula (XX):
wherein U, V and W are the same or different and are a hydrogen atom, halogen atom, optionally substituted alkyl, optionally substituted hydroxyl, alkylthio or optionally substituted amino, or a salt thereof;
6. A compound according to the above item 5, wherein U, V and W are the same or different and are a hydrogen, chlorine atom, methyl, trifluoromethyl or methoxy, or a salt thereof;
7. A compound according to the above item 1, wherein Q is pyridyl, pyrimidinyl, quinolyl, quinazolinyl, benzothiazolyl or pyrazolyl, each of which may be substituted, or a salt thereof;
8. A compound according to the above item 1, wherein Q is optionally substituted pyridyl, or a salt thereof;
9. A compound according to the above item 1, wherein Q is a group of the formula (a):
wherein R
12
and R
13
are the same or different and are a hydrogen atom, optionally substituted alkyl, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, optionally substituted amino, cycloalkyl, optionally substituted aryl or an optionally substituted heterocyclic group, or R
12
and R
13
are linked together to form a monocyclic or polycyclic ring which may contain a heteroatom, or a salt thereof;
10. A compound according to the above item 9, wherein R
12
and R
13
are the same or different and are a hydrogen atom, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted phenyl, optionally substituted naphthyl or an optionally substituted heterocyclic group, or R
12
and R
13
are linked together to form a cyclopentane ring or cyclohexane ring each of which may form a condensed ring with another ring, or a salt thereof;
11. A compound according to the above item 9, wherein R
12
is alkyl, or a salt thereof;
12. A compound according to the above item 9, wherein R
12
is methyl or ethyl, or a salt thereof;
13. A compound according to the above item 9, wherein R
13
is phenyl optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom, optionally substituted alkyl, optionally substituted hydroxyl, alkylthio, optionally substituted amino, nitro, phenyl and cyano, or a salt thereof;
14. A compound according to the above item 9, wherein R
13
is phenyl optionally substituted by 1 to 3 substituents selected from the group consisting of a chlorine atom, methyl, trifluoromethyl and methoxy, or a salt thereof;
15. A compound according to the above item 9, wherein R13 is pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, benzothiazolyl, quinolyl, quinazolinyl, pyrazinyl, morpholino or piperazinyl, each of which may substituted, or a salt thereof;
16. A compound according to the above item 1, wherein X is a hydrogen atom, or a salt thereof;
17. A compound according to the above item 1, wherein Y is alkoxy, or a salt thereof;
18. A compound according to the above item 1, wherein Y is methoxy, or a salt thereof;
19. A compound according to the above item 1, wherein Y is monoalkylamino, or a salt thereof;
20. A compound according to the above item 1, wherein Y is monomethylamino, or a salt thereof;
21. A compound according to the above item 1, wherein Z is an oxygen atom, or a salt thereof;
22. A compound according to the above item 1, wherein M is an oxygen atom, sulfur atom or optionally substituted amino, or a salt thereof;
23. A compound according to the above item 1, wherein n is 0, or a salt thereof;
24. A compound according to the above item 1, wherein n is 1, or a salt thereof;
25. An agricultural fungicidal composition comprising a compound according to the above item 1 as an active ingredient;
26. A process for producing a compound of the formula (I-1):
wherein each symbol is as defined in the above item 1, which comprises reducing a compound of the formula (II):
wherein each symbol is as defined in the above 1;
27. A process for producing a compound of the formula (I-2):
wherein R
3
is alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, (alkylthio)carbonyl, alkylsulfonyl, arylsulfonyl, or mono- or di-alkyl-substituted carbamoyl, and the other symbols are as defined in the above item 1, which comprises reacting a compound of the formula (I-1):
wherein each symbol is as defined in the above item 1, with a compound of the formula (XXII):
R
3
—L (XXII)
wherein L is a leaving group, and the other symbols are as defined above;
28. A process for producing a compound of the formula (IV-2):
wherein R
4
is alkyl, alkenyl, alkynyl, haloalkyl or alkoxyalkyl, R
5
is a hydrogen atom or alkyl, R
6
is a hydrogen atom, alkyl or hydroxylalkyl, and the other symbols are as defined in the above item 1, which comprises reacting a compound of the formula (IV-1):
wherein Y
1
is alkoxy or alkylthio and the other symbols are as defined above, with an amine;
29. A process for producing a compound of the formula (I
Masuko Michio
Murashi Takami
Ohtsuka Toshikazu
Suzuki Shinji
Takenaka Hideyuki
Balasubramanian Venkataraman
Foley & Lardner
Shah Mukund J.
Shionogi & Co. Ltd.
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