Biarylalkylenecarbamic acid derivatives and bacteriocides...

Details Biarylalkylenecarbamic acid derivatives and bacteriocides... Biarylalkylenecarbamic acid derivatives and bacteriocides...

2000-02-25

2003-09-16

Killos, Paul J. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S024000, C560S030000, C560S032000, C564S056000

Reexamination Certificate

active

06620961

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel biarylalkylenecarbamic acid derivatives and agricultural and horticultural fungicides containing them as active ingredients.
BACKGROUND ART
The biarylalkylenecarbamic acid derivatives as the compounds of the present invention have not been known to have excellent fungicidal activity although a number of carbamic acid derivatives have been reported so far.
The present inventors have conducted extensive research to develop novel agricultural and horticultural fungicides and have found out that the biarylalkylenecarbamic acid derivatives of the present invention (hereinafter referred to as the compounds of the present invention) are novel compounds which have not been reported in the literature and show remarkable effects as agricultural and horticultural fungicides. The present invention is accomplished on the basis of the discovery.
DISCLOSURE OF THE INVENTION
Namely, the present invention provides biarylalkylenecarbamic acid derivatives represented by general formula (I):
{wherein X is a halogen atom, a (C
1
-C
6
) alkyl group, a (C
1
-C
6
) alkoxy group, a (C
1
-C
4
) haloalkyl group or a (C
1
-C
4
) haloalkoxy group, n is 0 or an integer of from 1 to 4, R
1
is a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group or a (C
1
-C
4
) haloalkyl group, R
2
is a hydrogen atom, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
1
-C
4
) alkoxy group, a (C
1
-C
6
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
6
) alkylthio (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
6
) alkylcarbonyl group, a phenylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group or an aryl (C
1
-C
4
) alkyl group [which may be substituted with a halogen atom, a (C
1
-C
3
) alkyl group or a (C
1
-C
3
) alkoxy group], A is a (C
1
-C
7
) alkylene group which may be branched, G is an oxygen atom, a sulfur atom or a group—NR— [wherein R
3
is a hydrogen atom or a (C
1
-C
4
) alkyl group], and Q is a group represented by general formula:
wherein Y is a halogen atom, nitro, cyano, hydroxy, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group, a (C
3
-C
6
) cycloalkyl (C
1
-C
4
) alkyl group, a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
3
-C
6
) cycloalkoxy group, a (C
1
-C
6
) alkylthio group, a (C
1
-C
6
) alkylsulfinyl group, a (C
1
-C
6
) alkylsulfonyl group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
4
) alkylthio (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
4
) haloalkoxy group, a (C
1
-C
4
) haloalkylthio group, a (C
1
-C
4
) haloalkylsulfinyl group, a (C
1
-C
4
) haloalkylsulfonyl group, a (C
1
-C
4
) alkylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group, a group —CONR
4
R
5
[wherein R
4
and R
5
which may be the same or different, are hydrogen atoms or (C
1
-C
4
) alkyl groups], an amino group, a mono(C
1
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, a (C
1
-C
4
) alkylcarbonylamino group, an aryl group [which may be substituted with a halogen atom, a (C
01
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], an aryloxy group [which may be substituted with a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], an aryl (C
1
-C
4
) alkoxy group [which may be substituted with a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], or may form a methylenedioxy group together with an adjacent Y, and m is 0 or an integer of from 1 to 5} and agricultural and horticultural fungicides containing them as active ingredients.
The symbols and terms used herein are explained below.
A halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
An expression such as (C
1
-C
6
) means that the carbon number of the preceded group is, in this case, from 1 to 6.
A (C
1
-C
6
) alkyl group is a linear or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3,3-dimethylbutyl or the like.
A (C
3
-C
6
) cycloalkyl group is, for example, cyclopropyl, cyclopentyl, cyclohexyl or the like.
A (C
1
-C
4
) haloalkyl group is a linear or branched alkyl group substituted with halogen atom(s) such as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, pentafluoroethyl or the like.
A (C
2
-C
6
) alkenyl group is a linear or branched alkenyl group such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl or the like.
A (C
2
-C
6
) alkynyl group is a linear or branched alkynyl group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl or the like.
A (C
1
-C
6
) alkoxy group is an alkyloxy group having such an alkyl moiety as mentioned above.
A (C
2
-C
6
) alkenyloxy group is an alkenyloxy group having such an alkenyl moiety as mentioned above.
A (C
2
-C
6
) alkynyloxy group is an alkynyloxy group having such an alkynyl moiety as mentioned above.
A (C
3
-C
6
) cycloalkoxy group is a cycloalkyloxy group having such a cycloalkyl moiety as mentioned above.
A (C
1
-C
4
) haloalkoxy group is a haloalkyloxy group having such a haloalkyl moiety as mentioned above.
A (C
1
-C
6
) alkylthio group is an alkylthio group having such an alkyl moiety as mentioned above.
A (C
1
-C
6
) alkylsulfinyl group is an alkylsulfinyl group having such an alkyl moiety as mentioned above.
A (C
1
-C
6
) alkylsulfonyl group is an alkylsulfonyl group having such an alkyl moiety as mentioned above.
A (C
1
-C
4
) haloalkylthio group is a haloalkylthio group having such a haloalkyl moiety as mentioned above.
A (C
1
-C
4
) haloalkylsulfinyl group is a haloalkylsulfinyl group having such a haloalkyl moiety as mentioned above.
A (C
1
-C
4
) haloalkylsulfonyl group is a haloalkylsulfonyl group having such a haloalkyl moiety as mentioned above.
A (C
1
-C
7
) alkylene group which may be branched is, for example, —CH
2
—, —CH(CH
3
)—, —C(CH
3
)
2
—, —CH
2
CH
2
—, —CH
2
CH
2
CH
2
— or the like.
An aryl group is phenyl, &agr;-naphthyl, &bgr;-naphthyl or the like.
An aryl (C
1
-C
4
) alkyl group is benzyl or the like.
An aryloxy group is phenoxy, naphthoxy or the like.
An aryl (C
1
-C
4
) alkoxy group is benzyloxy or the like.
Specific examples of the compounds of the present invention are given below in Tables 1 to 53. However, the compounds of the present invention are by no means restricted to those specific examples. The compound Nos. are referred to in the description hereinafter.
TABLE 1

Comp.
m.p.
No.
Ym
G
R
1
R
2
(° C.)
1-1
H
O
CH
3
H
49-52
1-2
2-Cl
O
CH
3
H
oily
1-3
3-Cl
O
CH
3
H
oily
1-4
4-Cl
O
CH
3
H
85-88
1-5
2-F
O
CH
3
H
1-6
3-F
O
CH
3
H
oily
1-7
4-F
O
CH
3
H
60-61
1-8
3-Hr
O
CH
3
H
1-9
4-Br
O
CH
3
H
126-129
1-10
2-CH
3
O
CH
3
H
oily
1-11
3-CH
3
O
CH
3
H
oily
1-12
4-CH
3
O
CH
3
H
64-67
1-13
3-C
2
H
5
O
CH
3
H
oily
1-14
4-C
2
H
5
O
CH
3
H
57-58
1-15
3-C
3
H
7
O
CH
3
H
1-16
4-C
3
H
7
O
CH
3
H
1-17
3-C
3
H
7
-i
O
CH
3
H
oily
1-18
4-C
3
H
7
-i
O
CH
3
H
46-48
1-19
3-C
4
H
9
-t
O
CH
3
H
1-20
4-C
4
H
9
-t
O
CH
3
H
1-21
3-C
6
H
13
O
CH
3
H
1-22
4-C
6
H
13
O
CH
3
H

1-23
O
CH
3
H

1-24
O
CH
3
H

1-25
O
CH
3
H

1-26
O
CH
3
H

1-27
O
CH
3
H

1-28
O
CH
3
H
TABLE 2
Comp.
m.p.
No.
Ym
G
R
1
R
2
(° C.)
1-29
3-CH═CH
2
O
CH
3
H
1-30
4-CH═CH
2
O
CH
3
H
1-31
3-C≡CHCH
3
O
CH
3
H
1-32
4-C≡CHCH
3
O
CH
3
H
1-33
2-CF
3
O
CH
3
H
61-64
1-34
3-CF
3
O
CH
3
H
oily
1-35
4-CF
3
O
CH
3
H
94-95

1-36
O
CH
3
H

1-37
O
CH
3
H

1-38
3-OH
O
CH
3
H
1-39
4-OH
O
CH
3
H
1-40
2-OCH
3
O
CH
3
H
oily
1-41
3-OCH
3
O
CH
3
H
oily
1-42
4-OCH
3
O
CH
3
H
93-95
1-43
3-OC
2
H
5
O
CH
3
H
1-44
4-OC
2
H
5
O
CH
3
H
1-45
3-OC
3
H
7
-i
O
CH
3
H
1-46
4-OC
3
H
7
-i
O
CH
3
H

1-47
O
CH
3
H

1-48
O
CH
3
H

1-49
O
CH
3
H

1-50
O
CH
3
H

1-51
O
CH
3
H

1-52
O
CH
3
H

1-53
O
CH
3
H

1-54
O
CH
3
H
TABLE 3
Comp.
m.p.
No.
Ym
G
R
1
R
2
(° C.)
1-55
O
CH

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