4-benzoyl isoxazoles derivatives and their use as herbicides

Details 4-benzoyl isoxazoles derivatives and their use as herbicides 4-benzoyl isoxazoles derivatives and their use as herbicides

1995-11-01

2001-11-27

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S248000

Reexamination Certificate

active

06323155

ABSTRACT:

This invention relates to novel 4-benzoylisoxazole derivatives, compositions containing them, processes for their preparation, intermediates in their preparation and their use as herbicides.
Herbicidal 4-benzoylisoxazoles are described in European Patent Publication Number 0418175.
The present invention provides 4-benzoylisoxazole derivatives of formula (I):
wherein:
R represents the hydrogen atom or a group —CO
2
R
4
;
R
1
represents:
a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; or
a cycloalky group containing from three to six carbon atoms optionally substituted by one or more R
5
groups or one or more halogen atoms;
R
2
represents:
a halogen atom;
a straight- or branched-chain allyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a straight- or branched-chain alkyl group containing up to six carbon atoms which is substituted by one or more groups —OR
5
;
a group selected from nitro, cyano, —CO
2
R
5
, —S(O)
p
R
6
, —O(CH
2
)
m
OR
5
, —COR
5
, —NR
5
R
6
, —N(R
8
)SO
q
R
7
, —CONR
9
R
10
and —OR
51
;
phenyl optionally substituted by from one to three groups R
21
which may be the same or different;
R
3
represents —S(O)
q
R
7
;
X represents a group —N(R
8
)—;
n represents zero or an integer from one to four; where n is greater than one the groups R
2
may be the same or different;
R
4
represents a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
R
5
, R
51
and R
6
, which may be the same or different, each represents:
the hydrogen atom;
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
phenyl optionally substituted by from one to five groups R
2
which may be the same or different; or
a cycloalkyl group containing from three to six carbon atoms;
R
7
represents:
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
phenyl or benzyl optionally substituted by from one to five groups R
21
which may be the same or different;
or —NR
9
R
10
;
R
8
represents:
the hydrogen atom;
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to ten carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
phenyl optionally substituted by from one to five groups which may be the same or different selected from halogen, nitro, cyano, R
5
, S(O)
p
R
5
and —OR
5
; or
a group —OR
11
;
R
9
represents:
the hydrogen atom;
a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
or phenyl optionally substituted by from one to five groups R
2
which may be the same or different;
R
10
represents a group selected from R
5
and —OR
11
;
or R
9
and R
10
, together with the nitrogen to which they are attached, may form a 5 or 6 membered ring optionally containing an oxygen or nitrogen atom in the ring (e.g. pyrrolidine, morpholine, pyrrole, piperidine and piperazine), wherein the ring is optionally substituted by one or more alkyl groups containing up to 3 carbon atoms;
R
11
represents a straight- or branched-chain alkyl group containing up to six carbon atoms;
R
21
represents:
a halogen atom;
a straight- or branched-chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms;
or a group selected from nitro, cyano, —S(O)
p
R
5
and —OR
5
;
m represents one, two or three; and
p represents zero, one or two;
q represents zero or two;
and agriculturally acceptable salts thereof, which possess valuable herbicidal properties.
Furthermore in certain cases the groups R, R
1
, R
2
, and R
3
may give rise to geometric and/or optical isomers. All such forms are embraced by the present invention.
By the term “agriculturally acceptable salts” is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble.
The compounds of the invention, in some aspects of their activity, for example in their control of important weeds found in cereal crops, e.g.
Galium aparine
and
Avena fatua,
and in their selectivity in important cereal crops, e.g. wheat, show advantages over known compounds.
It will be understood that in the above definition R
2
does not include substituents containing two or more phenyl rings linked through a bridging group.
In one embodiment the invention provides compounds of formula I above wherein:
R represents the hydrogen atom or a group —CO
2
R
4
;
R
1
represents:
a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; or
a cycloalkyl group containing from three to six carbon atoms optionally substituted by one or more R
5
groups;
R
2
represents:
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a straight- or branched-chain alkyl group containing up to six carbon atoms which is substituted by a group —OR
5
;
a halogen atom;
phenyl optionally substituted by from one to three groups R
21
which may be the same or different;
a group selected from —COR
5
, nitro, cyano, —CO
2
R
5
, —S(O)
p
R
6
, —O(CH
2
)
m
OR
5
, —N(R
8
)SO
2
R
7
, —CONR
9
R
10
and —OR
51
;
R
3
represents —S(O)
q
R
7
;
X represents a group —N(R
8
)—;
n represents zero or an integer from one to four; where n is greater than one the groups R
2
may be the same or different;
R
4
represents a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
R
5
represents:
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or
a cycloalkyl group containing from three to six carbon atoms;
R
51
represents:
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
or phenyl optionally substituted by from one to five groups which may be the same or different selected from a halogen atom, a straight- or branched-chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; nitro, cyano, —S(O)
p
R
5
and —OR
5
;
R
6
represents:
a straight- or branched-chain akyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
or phenyl optionally substituted by from one to five groups which may be the same or different selected from a halogen atom, a straight- or branched-chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; nitro, cyano, —S(O)
p
R
5
and —OR
5
;
R
7
represents:
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
phenyl optionally substituted by from one to five groups R
21
which may be the same or different;
or —NR
9
R
10
;
R
8
represents:
the hydrogen atom; or
a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms;
a cycloalkyl group containing from three to six carbon atoms;
phenyl optionally substituted by from one to five groups which may be the same or different selected from a halogen atom, a straight- or branched-chain alkyl group containing up to three car

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