IP Library › Granted Patent US 7,067,668
Granted Patent B2
US 7,067,668 · App. 10/715,846 · Granted Jun 27, 2006

4-quinolinol derivatives and fungicides containing the same as an active ingredient used for agriculture and horticulture

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Quick Facts
Patent No.
US 7,067,668
App. No.
10/715,846
Granted
Jun 27, 2006
Kind
B2
Abstract

A new agricultural and horticultural fungicide having an excellent control effect is provided. 4-Quinolinol derivatives represented by the following formula: or agriculturally and horticulturally acceptable acid addition salts thereof.

Claims (286)

1. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein

R 1 represents

an alkali metal,

an alkaline earth metal, or

COR 4 in which R 4 is

a hydrogen atom,

an optionally substituted C1–C18 alkyl group,

an optionally substituted C2–C18 alkenyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted phenyl C1–C4 alkyl group,

an optionally substituted phenoxy C1–C4 alkyl group,

an optionally substituted aryl group,

OR 5 in which R 5 is an optionally substituted C1–C4 alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl C1–C4 alkyl group or an optionally substituted phenoxy C1–C4 alkyl group, or

NR 6 R 7 in which R 6 and R 7 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 1 and R 7 together with N may form a four- to six-membered ring containing one or two heteroatoms;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C1–C18 alkyl group; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 1 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

2. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents

an alkali metal,

an alkaline earth metal, or

COR 4 in which R 4 is

a hydrogen atom,

an optionally substituted C1–C18 alkyl group,

an optionally substituted C2–C18 alkenyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted phenyl C1–C4 alkyl group,

an optionally substituted phenoxy C1–C4 alkyl group,

an optionally substituted aryl group,

OR 5 in which R 5 is an optionally substituted C1–C4 alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl C1–C4 alkyl group or an optionally substituted phenoxy C1–C4 alkyl group, or

NR 6 R 7 in which R 6 and R 7 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 6 and R 7 together with N may form a four- to six-membered ring containing one or two heteroatoms;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C2–C4 alkenyl group; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

3. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents

an alkali metal,

an alkaline earth metal, or

COR 4 in which R 4 is

a hydrogen atom,

an optionally substituted C1–C18 alkyl group,

an optionally substituted C2–C 18 alkenyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted phenyl C1–C4 alkyl group,

an optionally substituted phenoxy C1–C4 alkyl group,

an optionally substituted aryl group,

OR 5 in which R 5 is an optionally substituted C1–C4 alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl C1–C4 alkyl group or an optionally substituted phenoxy C1–C4 alkyl group, or

NR 6 R 7 in which R 6 and R 7 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 6 and R 7 together with N may form a four- to six-membered ring containing one or two heteroatoms;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C1–C4 alkoxy group; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

a halogen atom,

an optionally substituted C1–C10 alkyl group,

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C1–C10 alkoxy group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl, C1–C4 alkoxy group and hydroxyl.

4. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents

an alkali metal,

an alkaline earth metal, or

COR 4 in which R 4 is

a hydrogen atom,

an optionally substituted C1–C18 alkyl group,

an optionally substituted C2–C 18 alkenyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted phenyl C1–C4 alkyl group,

an optionally substituted phenoxy C1–C4 alkyl group,

an optionally substituted aryl group,

OR 5 in which R 5 is an optionally substituted C1–C4 alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl C1–C4 alkyl group or an optionally substituted phenoxy C1–C4 alkyl group, or

NR 6 R 7 in which R 6 and R 7 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 6 and R 7 together with N may form a four- to six-membered ring containing one or two heteroatoms;

R 2 and R 3 together represent —(CH 2 )m- in which m is 3 or 4; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl, C1–C4 alkoxy group and hydroxyl.

5. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C1–C18 alkyl group; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

6. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C2–C4 alkenyl group; and

W represents 1 substituents on the nucleus which may be

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

7. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C2–C4 alkenyl group; and

W represents 2 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

8. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C2–C4 alkenyl group; and

W represents 3 to 4 substituents on the nucleus which may be identical or different and each of which is

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

9. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 represents an optionally substituted C1–C4 alkyl group;

R 3 represents an optionally substituted C1–C4 alkoxy group; and

W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is

a halogen atom,

an optionally substituted C1–C10 alkyl group,

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C1–C10 alkoxy group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

10. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 and R 3 together represent —(CH 2 )m- in which m is 3 or 4; and

W represents 1 substituent on the nucleus which is

a halogen atom,

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C1–C10 alkoxy group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

11. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof wherein R 1 represents a hydrogen atom;

R 2 and R 3 together represent —(CH 2 )m- in which m is 3 or 4; and

W represents 2 substituents on the nucleus which may be identical or different and each of which is

a halogen atom,

an optionally substituted C1–C10 alkyl group,

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C1–C10 alkoxy group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

12. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 represents a hydrogen atom;

R 2 and R 3 together represent —(CH 2 )m- in which m is 3 or 4; and

W represents 3 to 4 substituents on the nucleus which may be identical or different and each of which is

a halogen atom,

an optionally substituted C1–C10 alkyl group,

an optionally substituted C2–C4 alkenyl group,

an optionally substituted C2–C4 alkynyl group,

an optionally substituted C1–C10 alkoxy group,

an optionally substituted C3–C10 cycloalkyl group,

an optionally substituted aryl group,

an optionally substituted aryloxy group,

NR 8 R 9 in which R 8 and R 9 are each a hydrogen atom, an optionally substituted C1–C6 alkyl group or an optionally substituted phenyl group, or R 8 and R 9 together with N may form a four- to six-membered ring containing one or two heteroatoms,

COR 10 in which R 10 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

COOR 11 in which R 11 is a hydrogen atom, an optionally substituted C1–C4 alkyl group or an optionally substituted C2–C4 alkenyl group,

a nitro group, or

a cyano group;

wherein when optionally substituents present, the optional group is selected from the group consisting of halogen, C1–C4 alkyl group, C1–C4 alkoxy group and hydroxyl.

13. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-s-C 4 H 9 and 8-CH 2 OH.

14. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-s-C 4 H 9 and 8-CH 2 OH.

15. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-t-C 4 H 9 and 8-CH 2 OH.

16. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-t-C 4 H 9 and 8-CH 2 OH.

17. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-s-C 4 H 9 and 8-CH 2 Cl.

18. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-t-C 4 H 9 and 8-CH 2 Cl.

19. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-c-C 5 H 9 and 8-methyl.

20. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-c-C 5 H 9 and 8-methyl.

21. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-c-C 5 H 9 and 8-Cl.

22. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-c-C 5 H 9 and 8-Cl.

23. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-s-C 4 H 9 and 8-CHO.

24. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-s-C 4 H 9 and 8-CHO.

25. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-t-C 4 H 9 and 8-CHO.

26. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-t-C 4 H 9 and 8-CHO.

27. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-CH 3 CH═C(CH 3 ) and 8-methyl.

28. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-CH 3 CH═C(CH 3 ) and 8-methyl.

29. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is a hydrogen atom; R 2 and R 3 are each methyl; and W are 6-CH 3 CH═C(CH 3 ) and 8-F.

30. A 4-quinolinol compound represented by the formula (I):

or an agricultural and horticulturally acceptable acid addition salt thereof, wherein R 1 is CH 3 CO; R 2 and R 3 are each methyl; and W are 6-CH 3 CH═C(CH 3 ) and 8-F.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2011
From: MEIJI SEIKA KAISHA, LTD.
To: MEIJI SEIKA PHARMA CO., LTD.
Reel/Frame 027211/0418 →