Benzoyl derivatives, process for their preparation and their...

Details Benzoyl derivatives, process for their preparation and their... Benzoyl derivatives, process for their preparation and their...

1999-09-02

2001-10-02

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C564S302000, C564S315000, C564S408000, C564S219000, C564S261000, C504S243000, C504S242000, C504S251000, C504S235000, C504S288000, C504S283000, C546S208000, C549S208000, C548S325500, C548S127000

Reexamination Certificate

active

06297196

ABSTRACT:

The invention relates to the technical field of the herbicides and plant growth regulators, in particular that of the herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants.
From various publications, it is already known that certain benzoyl derivatives have herbicidal properties. Thus, EP-A 0 712 853 and EP-A 0 841 335 describe fused benzoyl derivatives which carry an alkyl radical in the &agr;-position of the fused-on ring system.
EP-A 0 629 623, EP-A 0 810 227 and EP-A 0 819 691 describe fused benzoyl derivatives which are substituted in the &agr;-position of the fused-on ring system by an alkoxy radical. WO 97/23135 discloses fused benzoyl derivatives which carry a radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy and alkoxyimino in the &agr;-position of the fused-on ring system. WO 98/29406 discloses fused benzoyl derivatives which carry one or two radicals from the group consisting of alkyl, alkoxyimino, alkoxy, alkylthio and disubstituted amino in the &agr;-position of the fused-on ring system. Here, the three last-mentioned radicals may also be present in cyclic form, so that a cycloalkoxy, cycloalkylthio or cycloalkylamino radical is present in the &agr;-position of the fused-on ring system. Additionally, WO 98129406 mentions a fused benzoyl derivative where a (2-tetrahydrofuryl)methyloxy radical is present in the abovementioned &agr;-position.
Furthermore, it is known from various publications that herbicides from the group of the benzoylcyclohexanediones as inhibitors of para-hydroxyphenylpyruvate dioxygenase are based on the same mechanism of action as those from the group of the benzoylisoxazoles, cf.
J. Pesticide Sci
. 21, 473-478 (1996),
Weed Science
45, 601-609 (1997),
Pesticide Science
50, 83-84, (1997) and
Pesticide Outlook
, 29-32, (December 1996). Additionally, from
Pesticide Science
50, 83-84, (1997), it is known that a benzoylisoxazole of the formula (A) can rearrange under certain conditions to give a benzoyl-3-oxopropionitrile of the formula (B).
However, the use of the benzoyl derivatives known from these publications is frequently associated with disadvantages in practice. Thus, the herbicidal or plant-growth-regulating activity of the known compounds is not always sufficient, or, if the herbicidal activity is sufficient, undesirable damage to the useful plants is observed.
It is an object of the present invention to provide herbicidal and plant-growth-regulating compounds which overcome the disadvantages known from the prior art.
This object is achieved by benzoyl derivatives of the formula (I)
in which
Q is a radical of the formula (II), (III) or (IV)
R
1
, R
2
, R
3
independently of one another are hydrogen, hydroxyl, thio, amino, cyano, nitro, halogen or an unsubstituted or substituted hydrocarbon radical which may or may not contain one or more additional, identical or different, heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen, fluorine, chlorine, bromine and iodine;
R
4
is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxycarbonyl, phenyl, where the six last-mentioned groups are unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy and alkylthio;
R
5
is heteroaryl, heterocylyl or aryl which is unsubstituted or mono- or polysubstituted by identical or different radicals, or is a radical selected from the group consisting of —O—N═CR
l
R
m
, —P(═O)(OR
i
)(R
j
), —P(═O)(OR
i
)(OR
k
) or
 or, if E is a bond and l is zero, R
5
can also be hydroxyl,
A is a divalent unit selected from the group consisting of O, S, SO, SO
2
, NR
a
, CHR
a
and CR
a
R
b
;
B is a chain which comprises one to four carbon atoms, which is saturated or contains one or more multiple bonds and which is unsubstituted or substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or by an unsubstituted or alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, halogen-, cyano- or nitro-substituted phenyl radical;
E is a bond, a one- to six-membered chain which is saturated or contains one or more multiple bonds and which consists of divalent units selected from the group consisting of C, CR
c
, CR
c
R
d
, N, NR
c
, S, SO, SO
2
, O and CO;
X is a divalent unit selected from the group consisting of O, S and NR
e
;
R
6
is alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, cyanato, thiocyanato, halogen or OR
f
;
Y is a divalent unit selected from the group consisting of O, S, NH, N-alkyl or CHR
7
;
R
7
is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, phenyl, where the hydrocarbon moiety of the eight last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, alkylthio and alkyloxy, or
two radicals R
7
which are attached to a joint carbon atom form a chain selected from the group consisting of OCH
2
CH
2
O, OCH
2
CH
2
CH
2
O, SCH
2
CH
2
S and SCH
2
CH
2
CH
2
S, this chain being unsubstituted or substituted by one to four methyl groups, or
two radicals R
7
which are attached to directly adjacent carbon atoms form a bond or together with the carbon atoms that carry them form an unsubstituted or substituted 3- to 6-membered ring;
Z is a bond, a divalent unit selected from the group consisting of O, S, SO, SO
2
, NH, N-alkyl or CHR
7
, where Y and Z should not simultaneously be a divalent unit which contains an oxygen, nitrogen or sulfur atom as chain member;
G
1
-G
2
is a divalent unit selected from the group consisting of OCR
9
, SCR
9
and NR
10
COR
11
, where the attachment to the ring system is to be carried out such that the carbon atom of this divalent unit is in each case attached to the carbon atom of the ring system via a double bond;
R
8
is hydrogen, alkyl or alkoxycarbonyl;
R
9
is hydrogen, alkyl, cycloalkyl, haloalkyl or halocycloalkyl;
R
10
is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, where the six last-mentioned groups are unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro and alkoxy;
R
11
is hydrogen, formyl, alkyl, haloalkyl, alkoxyalkyl or a group L-R
12
;
L is a divalent unit selected from the group consisting of SO
2
, CO, CHR
g
CO or CR
g
R
h
;
R
12
is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkyl or is phenyl which is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of cyano, nitro, alkyl, alkoxy, haloalkyl and haloalkoxy;
R
a
and R
b
independently of one another are hydrogen, halogen, cyano, nitro, formyl, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl and alkylsulfonyl, where the hydrocarbon moiety of the six last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy and alkylthio;
R
c
and R
d
independently of one another are hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, haloalkylcarbonylamino, alkylcarbonyl-N-alkylamino, alkylsulfonyl, alkylsulfinyl, alkylsulfonylamino, haloalkylsulfonyl, haloalkylsulfinyl, alkylsulfonylamino and alkylsulfonyl-N-alkylamino;
R
e
is hydrogen, formyl, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl and alkylsulfonyl, where the hydrocarbon moiety of the six last-mentioned radicals may be unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alky

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