Triketone derivatives

Details Triketone derivatives Triketone derivatives

2000-06-23

2001-11-13

Lambkin, Deborah C. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C549S023000

Reexamination Certificate

active

06316390

ABSTRACT:

TECHNICAL FIELD
The present invention relates to triketone derivatives including their salts and herbicidal compositions containing the derivatives. More particularly, the present invention relates to triketone derivatives having specific structure and their salts, and herbicidal compositions containing the derivatives as effective component which show a broad spectrum of controlling growth of cropland weeds even in small application rates without causing injury to field crops such as corn, etc.
BACKGROUND ART
Since herbicides are chemicals important for saving weed control working and achieving high crop yield, research and development of new herbicides have been extensively conducted for a long time and numerous types of chemicals have been practically used. However, the need still continues for new chemicals having more effective weed control activity, particularly, new chemicals which can selectively control the growth of objective weeds in small application rates without causing injury to agronomic crops.
In croplands of corn, etc., triazine herbicides such as atrazine and acid anilide herbicides such as alachlor and metolachlor have been used. However, atrazine is not sufficient for controlling Graminaceous weeds, although effective for controlling broad-leaved weeds. Alachlor and metolachlor in turn exhibit a low controlling activity against active broad-leaved weeds, although effective for controlling Graminaceous weeds. No herbicide is found at present, which can control the growth of gramineous weeds and broad-leaved weeds simultaneously by sole application. Moreover, the above herbicides must be used in larger amounts and not environmentally suitable.
Under the above circumstances, the inventors developed and proposed novel triketone derivatives having thiochroman ring (WO97/03064), which is represented by the following compound.
WO97/08164 discloses structurally specific triketone derivatives having thiochroman ring, which are represented by the following compounds.
However, the proposed compounds are still insufficient in herbicidal activity particularly in foliage treatment of Graminaceous weeds.
MEANS FOR SOLVING THE PROBLEMS
Therefore, objects of the present invention are to provide novel triketone derivatives having a broad spectrum of controlling the growth of cropland weeds in small application rates without causing injury to crops such as corn, and herbicidal compositions containing them.
As the result of extensive studies to achieve the above objects, the inventors have found that novel triketone derivatives represented by the formula (I) or their salts prevent growth of various cropland weeds in small application rates without causing injury to crops such as corn. The present invention has been accomplished based on this finding.
Thus, a first object of the present invention is achieved by a triketone derivative represented by the following formula (I) or a salt thereof:
wherein
Y
1
represents C
1
-C
4
alkyl, halogen or C
1
-C
4
haloalkyl;
Y
2
represents hydrogen, C
1
-C
4
alkyl or halogen;
Y
3
represents hydrogen or C
1
-C
6
alkyl;
n represents 0, 1 or 2;
p represents 0 or 1;
R
1
, R
2
, R
3
and R
4
each independently represents hydrogen, C
1
-C
4
alkyl or phenyl, R
1
or R
2
being optionally bonded to R
3
or R
4
to form a double bond in the molecule when p is 1; and
X represents oxygen group atom or group represented by the following formula:
wherein R
5
and R
6
each independently represents hydrogen, C
1
-C
4
alkyl or phenyl. Hereinafter, the triketone derivatives and salts thereof may be collectively referred to as “triketone derivatives”.
A second object of the present invention is achieved by herbicidal composition containing the tiiketone derivatives represented by the formula (I) and/or salts thereof as effective components.
PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
The triketone derivatives of the present invention will be described first.
The triketone derivatives of the present invention are represented by the formula (I).
In the formula (I), Y
1
represents C
1
-C
4
alkyl, halogen or C
1
-C
4
haloalkyl. Examples of C
1
-C
4
alkyl include methyl, ethyl, propyls such as n-propyl and i-propyl and butyls such as n-butyl and i-butyl. Examples of halogen include fluorine, chlorine, bromine and iodine. Examples of C
1
-C
4
haloalkyl include the above alkyls substituted with 1 to 9 halogen atoms such as —CH
2
Cl, —CHCl
2
, —CCl
3
, —CH
2
F, —CHF
2
, —CF
3
, —CCl
2
CH
3
, —CF
2
CH
3
, —CH
2
CH
2
F, —CH
2
CH
2
CHF
2
, —CF
2
CF
3
, —CH
2
CH
2
CHCl
2
, —CH
2
CH
2
CH
2
CH
2
Cl, —CH
2
CH
2
CH
2
CH
2
F, —CH(CH
3
)CH
2
Cl, —CH(CH
3
)CH
2
F and —CH(C
2
H
5
)CH
2
F. Among these substituents, methyl, chlorine and —CF
3
are preferable, and methyl is more preferable as Y
1
.
Y
2
represents hydrogen, C
1
-C
4
alkyl or halogen. Examples of C
1
-C
4
alkyl and halogen are the same as those for Y
1
. Y
2
is preferably hydrogen, methyl or fluorine and more preferably hydrogen or methyl. Y
2
representing C
1
-C
4
alkyl or halogen may be bonded to either 7-position or 8-position, preferably 8-position of the thiochroman ring.
Y
3
represents hydrogen or C
1
-C
6
alkyl. Examples of C
1
-C
6
alkyl include methyl, ethyl, propyls such as n-propyl and i-propyl, butyls such as n-butyl and i-butyl, pentyls such as n-pentyl and hexyls such as n-hexyl. Hydrogen, methyl or ethyl is preferable as Y
3
.
Subscript “n” represents the number of oxygen bonded to sulfur atom, and is 0, 1 or 2. Sulfur constitutes sulfide when n is 0, sulfoxide when n is 1, and sulfone when n is 2. The subscript n is preferably 2, i.e., sulfone is preferable.
Subscript “p” represents 0 or 1. (Hetero)cyclic diketone ring bonded to the thiochroman ring is a five-membered ring when p is 0 and a six-membered ring when p is 1. The subscript p is preferably 1, i.e., the (hetero)cyclic diketone ring bonded to the thiochroman ring is preferably six-membered ring.
R
1
, R
2
, R
3
and R
4
each independently represents hydrogen, C
1
-C
4
alkyl or phenyl. Examples of C
1
-C
4
alkyl are the same as those for Y
1
. When p is 1, R
1
or R
2
may be bonded to R
3
or R
4
to form a double bond in the molecule. R
1
, R
2
, R
3
and R
4
each is preferably hydrogen or methyl and more preferably hydrogen.
X represents oxygen group atom or group represented by the following formula:
Examples of oxygen group atom include oxygen and sulfur. R
5
and R
6
in the alkylidene group represented by the above formula each independently represents hydrogen, C
1
-C
4
alkyl or phenyl. Examples of C
1
-C
4
alkyl are the same as those for Y
1
. X is preferably oxygen or a group represented by the following formula:
wherein R
5
and R
6
each independently represents hydrogen or methyl.
The triketone derivatives represented by the formula (I) may be tautomerized as shown below. The following tautomers are included in the ketone derivatives of the present invention.
In the above formulae, Y
1
, Y
2
, Y
3
, n, p, R
1
, R
2
, R
3
, R
4
and X are as defined in the formula (I).
The triketone derivatives represented by the formula (I) are acidic substances and can be easily made into salts by treating with a base. The salts thus formed are also included in the present invention.
Known bases can be used without specific restriction. Examples of the base include organic bases such as amines and anilines and inorganic bases such as sodium compounds and potassium compounds. Examples of the amines include monoalkylamines, dialkylamines and trialkylamines. Alkyl in the alkylamines is generally C
1
-C
4
alkyl. Examples of the anilines include aniline, monoalkylanilines and dialkylanilines. Alkyl in the alkylanilines is generally C
1
-C
4
alkyl. Examples of the sodium compounds include sodium hydroxide and sodium carbonate. Examples of the potassium compounds include potassium hydroxide and potassium carbonate. Of the above bases, sodium compounds, potassium compounds and trialkylamines are preferable.
The triketone derivatives of the present invention can be produced, for example, by the following proc

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