Benzoic acid intermediates to 4-benzoylisoxazole herbicides

Details Benzoic acid intermediates to 4-benzoylisoxazole herbicides Benzoic acid intermediates to 4-benzoylisoxazole herbicides

1999-10-19

2002-04-09

Killos, Paul J. (Department: 1623)

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

Organic compounds

Carboxylic acids and salts thereof

C560S029000

Reexamination Certificate

active

06369270

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel 4-benzoylisoxazole derivatives, compositions containing them, processes for their preparation, intermediates in their preparation and their use as herbicides.
BACKGROUND ART
Herbicidal 4-benzoylisoxazoles are described in European Patent Publication Numbers 0418175, 0487357, 0527036, 0527037, 0560482, and 0560483.
DESCRIPTION OF THE INVENTION
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 halogen atoms; or
a cycloalkyl 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 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 one or more groups —OR
5
; or
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
2
R
7
, —OR
5
, —OSO
2
R
7
, —(CR
9
R
10
)
t
SO
q
R
7
and —CONR
5
R
6
;
R
3
represents a group —C(Z)═Y;
in which Y═O or S (preferably Y represents O);
Z represents a group R
63
, —NR
60
R
61
, —N(R
60
)—NR
61
R
62
, —SR
63
, —OR
63
; wherein R
60
, R
61
and R
62
which may be the same or different each represents:
a 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; or a group —(CH
2
)
w
— [phenyl optionally substituted by one to five groups R
21
];
R
63
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 group —(CH
2
)
w
—[phenyl optionally substituted by one to five groups R
21
];
X represents a group —N(R
8
′)—; in which,
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;
—(CH
2
)
w
—[phenyl optionally substituted by from one to five groups R
21
]; or
a group —OR
11
;
and the groups R
3
and R
8
′ in the grouping of formula —N(R
8
′)—R
3
may, together with the nitrogen atom to which they are attached, form a 4 to 6 membered ring of formula (AA), (AB), (AC) or (AD):
wherein
E represents an alkylene or alkylidene chain of 1 or 3 carbon atoms optionally substituted by a group R
64
and E
1
represents alkyl of 1 or 2 carbon atoms optionally substituted by a group R
64
, wherein R
64
represents an optionally halogenated straight- or branched-chain alkyl group containing up to 6 carbon atoms and R
65
represents the hydrogen atom or an optionally halogenated straight- or branched-chain alkyl group containing up to 6 carbon atoms; in formula (AB) the groups Y may be the same or different;
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
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;
R
6
′ is as hereinbefore defined for R
6
but excluding the hydrogen atom;
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;
a group —(CH
2
)
w
—[phenyl optionally substituted by from one to five groups R
21
];
R
8
is as hereinbefore defined for R
8
′;
R
9
and R
10
represent a group selected from:
the hydrogen atom;
a straight- or branched-chain alkyl group containing up to six (preferably up to 3) carbon atoms optionally substituted by one or more halogen atoms;
R
11
represents a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen 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
;
wherein R
5
′ is as hereinbefore defined for R
5
but excluding the hydrogen atom;
m represents one, two or three;
p represents zero, one or two;
q represents zero, one or two;
t represents one, two, three or four (preferably one); and
w represents zero or one;
and agriculturally acceptable salts thereof, which possess valuable herbicidal properties.
Furthermore in certain cases the groups R, R
1
, R
2
and others 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, Alopecurus myosuroides
and
Avena fatua
(especially
Galium aparine
), and in their selectivity in important cereal crops, e.g. wheat and maize, show advantages over known compounds.
DETAILED DESCRIPTION OF THE INVENTION
The compounds are of particular interest against monocotyledonous weeds by post-emergence application.
Preferably the 2-position of the benzoyl ring is substituted, most preferably by the group —XR
3
.
Preferably the 5- and 6-positions of the benzoyl ring are unsubstituted.
Preferred compounds of formula (I) are those wherein:
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 methyl groups or one or more halogen atoms;
R
2
represents:
a halogen 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;
a straight- or branched-chain alkyl group containing up to six carbon atoms which is substituted by a group —OR
5
; or
a group selected from nitro, cyano, —CO
2
R
5
, —S(O)
p
R
6
′, —O(CH
2
)
m
OR
5
, —COR
5
, —NR
8
SO
2
R
7
, —OR
5
, —CH
2
SO
q
R
7
;
X represents a group —N(R
8
′)—; or the groups R
3
and R
8
′ in the grouping of formula —N(R
8
′)—R
3
, together with the nitrogen atom to which they are attached, form a ring of formula (AB) above;
Z represents a group R
63
, —NR
60
R
61
, —SR
63
or —OR
63
; and
n represents zero, one, two or three.
A further preferred class of compounds of formula (I) are those wherein:
R
1
represents:
methyl ethyl i-propyl, cyclopropyl or 1-methylcyclopropyl;
R
2
represents:
a halogen atom;
a straight- or branched-chain alkyl or alkenyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms; or
a group selected from —COR
5
, —CO
2
R
5
, —S(O)
p
R
6
′, —CH
2
SO
q
R
7
, —O(CH
2
)
m
OR
5
, —OR
5
and —NR
8
SO
2
R
7
;
R
5
and R
6
′, which may be the same or different, each represents:
a straight- or branched-chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms;
R
7
represents:
a straight- or branched-chain alkyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms;
R
8
represents:

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