Phenylacetylene derivatives

Details Phenylacetylene derivatives Phenylacetylene derivatives

1999-02-23

2001-01-16

Qazi, Sabiha N. (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S261000, C548S251000

Reexamination Certificate

active

06174839

ABSTRACT:

The present invention relates to novel phenylacetylene derivatives, to processes for their preparation and to their use as herbicides.
It has already been known that certain heterocyclic compounds comprising a substituted phenyl moiety have herbicidal activity (see e.g. Japanese Patent Official Announcement (kohyo) Hei 2-501309; Japanese Patent Kokai Publications Sho 60-172967, Sho61-2659, Sho 61-43188, Sho 61-212558, Sho 62-181283, Sho 63-152366, Sho63-230678, Sho 63-313779, Hei 1-56674, Hei 1-199978, Hei 4-117355, Hei4-217968, Hei 6-321941, Hei 7-89313, Hei 7-89941, Hei 7-187919, Hei 7-188220, Hei 7-188221, Hei 8-253476, Hei 8-259546; EP-A 361114; DE-A 1695840, DE-A 2612731; FR-A 2660308, U.S. Pat. No. 5,136,868, U.S. Pat. No. 5,310,723, WO90/06748, WO94/04511, WO94/13652, WO95/33718, WO95/33719).
There have now been found novel phenylacetylene derivatives of formula (I).
wherein
X represents hydrogen, halogen, C
1-6
alkyl or C
1-6
haloalkyl,
Y represents hydrogen, hydroxy, halogen, cyano, nitro, C
1-6
alkyl, C
1-6
haloalkyl, C
1-6
alkoxy, C
3-8
cycloalkoxy, C
1-6
haloalkoxy, C
1-3
alkoxy-C
1-3
alkoxy, C
1-6
alkylthio, C
3-8
cycloalkylthio, C
1-6
haloalkylthio, C
1-6
alkylsulfinyl, C
1-6
alkylsulfonyl, C
3-8
cycloalkylsulfonyl, C
1-6
haloalkylsulfonyl, C
1-6
alkylsulfonyloxy, C
3-6
alkenyloxy, C
3-6
alkynyloxy, a group SO
2
NR
a
R
b
, a group COOR
c
, a group CONR
d
R
e
, optionally substituted amino, a group A
1
—(CH
2
)n—CHR
f
—COOR
g
, C
1-3
alkoxycarbonyl-C
1-3
alkyl or C
1-3
alkoxycarbonyl-C
1-3
haloalkyl, or
Y may form a 5- or 6-membered ring together with Z which is vicinal to the carbon atom of Y,
R
a
and R
b
each represent independently hydrogen or C
1-6
alkyl, or
R
a
and R
b
may form together with the N atom to which they are bonded a 5- or 6-membered heterocyclic group,
R
c
represents hydrogen, an alkali metal, an alkaline earth metal, C
1-6
alkyl or C
1-4
alkoxy-carbonyl-C
1-4
alkyl,
R
d
represents hydrogen or C
1-6
alkyl,
R
e
represents hydrogen or C
1-6
alkyl,
R
f
represents hydrogen, halogen or C
1-6
alkyl,
R
g
represents hydrogen, an alkali metal, an alkaline earth metal or C
1-6
alkyl,
A
1
represents oxygen or sulfur,
n is 0 or 1,
Z represents hydrogen or halogen,
m is 1 or 2,
R represents hydrogen, halogen, C
1-6
alkyl, hydroxy-C
1-6
alkyl, tri(C
1-6
alkyl)silyl, a group COOR
c
or a group CONR
d
R
e
,
 R
2
represents hydrogen or C
1-6
haloalkyl,
R
3
represents hydrogen, cyano, halogen or C
1-6
alkyl,
R
4
represents hydrogen, amino or C
1-6
alkyl,
R
5
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
3-8
cycloalkyl or C
3-8
alkynyl,
R
6
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl or C
1-3
alkoxy-C
1-3
alkyl,
R
7
represents hydrogen, halogen, amino, cyano, C
1-6
alkyl or C
1-6
haloalkyl,
R
8
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
1-6
alkoxy, C
1-6
alkylthio, C
1-6
haloalkoxy, C
1-6
haloalkylthio or C
3-8
cycloalkyl,
R
9
represents hydrogen, C
1-6
alkyl or C
1-6
haloalkyl,
R
10
represents hydrogen or C
1-6
alkyl,
R
11
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
3-8
alkynyl or C
3-8
cycloalkyl,
R
12
represents hydrogen, halogen, cyano or amino,
R
13
represents halogen, a group A
1
—CHR
10
R
14
or a group NR
10
R
14
,
R
14
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
3-8
cycloalkyl, optionally substituted phenyl or an optionally substituted 5- or 6-membered heterocyclic group,
R
15
represents halogen or OR
16
,
R
16
represents hydrogen or acyl,
R
17
and R
18
each represent independently hydrogen or C
1-6
alkyl,
R
19
and R
20
each represent independently represent hydrogen, C
1-6
alkyl, C
1-6
haloalkyl or C
3-8
cycloalkyl,
R
21
represents hydrogen or C
1-6
alkyl,
R
22
represents hydrogen, C
1-6
alkyl or C
1-6
haloalkyl,
R
23
hydrogen, halogen, cyano, optionally substituted phenyl or a radical CONR
d
R
e
,
R
24
represents C
1-6
alkyl, C
1-6
haloalkyl, optionally substituted phenyl or C
3-8
cycloalkyl,
R
25
represents cyano or a radical CONR
d
R
e
,
R
26
represents C
1-6
alkyl, C
1-6
haloalkyl, C
3-6
cycloalkyl, C
1-3
alkyl-C
3-6
cycloalkyl, 1-cyano-C
3-6
cycloalkyl, 1-amino-C
3-6
cycloalkyl, 1-ethynyl-C
3-6
cycloalkyl, 1-cyano-C
3-5
alkyl or 1-ethynyl-C
3-5
alkyl,
R
27
represents hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
3-6
cycloalkyl, C
1-6
alkoxy, C
1-6
haloalkoxy or C
3-6
cycloalkyl-C
1-4
alkoxy,
R
28
represents hydrogen or halogen,
A
2
represents oxygen or sulfur, and
A
3
represents oxygen, sulfur or CH
2
.
The phenylacetylene derivatives of formula (I) according to the invention can be obtained by the following processes:
(a) In the case where R is a group other than hydrogen:
compounds of formula (II)
 wherein X, Y, Z, m and Q are defined as above, and hal is bromine or iodine, are reacted with compounds of formula (III)
R′—C≡CH  (III)
 wherein R′ represents a group as defined for the above R with the exception of hydrogen, if appropriate, in the presence of inert solvents, a catalyst, a promoter and an acid binder, or
(b) in the case where R is hydrogen:
compounds of formula (Ia)
 wherein X, Y, Z, m and Q are defined as above are reacted with a desilylating agent in the presence of appropriate diluents.
The phenylacetylene derivatives of formula (I) according to the invention, exhibit powerful herbicidal effects.
Surprisingly, the phenylacetylene derivatives of formula (I) provided by the invention exhibit substantially superior herbicidal effects in comparison with the previously known compounds described in the above prior art literature.
In this specification, the “halogen” and the halogen atoms in the “haloalkyl”, “haloalkoxy”, “haloalkylthio” and “haloalkylsulfonyl” radicals represent fluorine, chlorine, bromine or iodine, preferably being fluorine, chlorine or bromine.
When these “haloalkyl”, “haloalkoxy”, “haloalkylthio” and “haloalkylsulfonyl” radicals contain two or more halogen atoms, these halogen atoms may be same or different.
The “alkyl” may be straight-chain or branched and includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, 2-ethylhexyl, and the like.
The “haloalkyl” may be straight-chain or branched and includes, for example, chloromethyl, trichloro-methyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, 2,2,2-trifluoroethyl, 3-fluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3-tetrafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, 2-chloro-1,1-dimethylethyl, 2-fluoro-1,1-dimethylethyl, and the like.
The “alkoxy” may be straight-chain or branched and includes, for example, methoxy, ethoxy, isopropoxy, propoxy, butoxy, isobutoxy, tert-butoxy, pentoxy, and the like.
The “cycloalkyl” includes, for example, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
The “cycloalkoxy” includes, for example, cyclopropyloxy, 1-methylcyclopropyloxy, 2-methylcyclo-propyloxy, cyclobutyloxy, cyclopentyloxy, 2-methylcyclopentyloxy, 3-methylcyclopentyloxy, cyclohexyloxy, 2-methylcyclohexyloxy, 3-methylcyclohexyloxy, 4-methylcyclohexyloxy, cycloheptyloxy, cyclooctyloxy, and the like.
The “haloalkoxy” may be straight-chain or branched and includes, for example, difluoromethoxy, trifluoromethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, and the like.
The “alkylthio” may be straight-chain or branched and includes, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, neopentylthio, hexylthio, 2-ethylhexylthio, and the like.
The “cycloalkylthio” includes, for example, cyclopropylthio, 1-methylcyclopropylthio, cyclopentylthio, 1-methylcyclopentylthio, cyclohexylthio, 1-methylcyclohexylthio, 2-methylcyclohexylthio, 3-methyl-cyclohexylthio, cycloheptylthio, cyclooctylthio, and the like.
The “haloalkylthio” may be st

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