Herbicidal composition

Details Herbicidal composition Herbicidal composition

1999-06-24

2001-09-25

Rotman, Alan L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S288000, C504S261000, C504S292000, C504S307000, C549S014000, C549S023000

Reexamination Certificate

active

06294504

ABSTRACT:

The present invention relates to new antidotes, their use as antidotes in herbicidal compositions, these compositions and their usage in the control of grasses and weeds in cultivations of useful plants, especially in cultivations of maize, cereals, soybeans and rice.
The objects of the present invention are compounds of formula I
wherein
R
1
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkyl substituted by C
1
-C
4
-alkyl-X- or C
1
-C
4
-halogen-alkyl-X-,
C
1
-C
4
-halogen-alkyl, nitro, cyano, -COOR
8
, —NR
11
R
12
, —SO
2
NR
11
R
12
or —CONR
13
R
14
;
R
2
is hydrogen, halogen, C
1
-C
4
-alkyl, trifluoromethyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogen-alkoxy;
R
3
is hydrogen, halogen or C
1
-C
4
-alkyl;
U, V, W and Z. independently of one another, are oxygen, sulphur, C(R
15
)R
16
, carbonyl, NR
17
or
a group
with the provisos that
a) at least one of the ring members U, V, W or Z is carbonyl, and one ring member which is adjacent to this or these ring members signifies the group
whereby this group only appears once; and
b) two adjacent ring members U and V, V and W and W and Z cannot simultaneously signify oxygen;
R
4
and R
5
, independently of one another, signify hydrogen or C
1
-C
8
-alkyl; or
R
4
and R
5
together form a C
2
-C
6
-alkylene group;
A is R
7
Y— or —NR
18
R
19
;
X is oxygen or —S(O)
p
;
Y is oxygen or sulphur;
R
7
is hydrogen, C
1
-C
8
-alkyl, C
1
-C
4
-halogen-alkyi, C
1
-C
4
-alkoxy-C
1
-C
8
-alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
8
-alkyl or phenyl-C
1
-C
8
-alkyl, whereby the phenyl ring may be substituted by halogen, C
1
-C
4
-alkyl, trifluoromethyl, methoxy or methyl-S(O)
p
-; C
3
-C
6
-alkenyl, C
3
-C
6
-halogen-alkenyl, phenyl-C
3
-C
6
-alkenyl, C
3
-C
6
-alkinyi, phenyl-C
3
-C
6
-alkinyl, oxetanyl, furfuryl or tetrahydrofurfuryl;
R
8
is hydrogen or C
1
-C
4
-alkyl;
R
9
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkylcarbonyl;
R
10
is hydrogen or C
1
-C
4
-alkyl; or
R
9
and R
10
together form a C
4
- or C
5
-alkylene group;
R
11
, R
12
, R
13
and R
14
, independently of one another, are hydrogen or C
1
-C
4
-alkyl; or R
11
together with R
12
or R
13
together with R
14
, independently of one another, are C
4
- or C
5
-alkylene, whereby one carbon atom may be replaced by oxygen or sulphur, or one or two carbon atoms may be replaced by —NR
15
-;
R
15
and R
16
, independently of one another, are hydrogen or C
1
-C
8
-alkyl; or
R
15
and R
16
together are C
2
-C
6
-alkylene;
R
17
is hydrogen, C
1
-C
8
-alkyl, optionally substituted phenyl or benzyl optionally substituted on the phenyl ring;
R
18
is hydrogen, C
1
-C
8
-alkyl, phenyl, phenyl-C
1
-C
8
-alkyl, whereby the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH
3
, C
1
-C
4
-alkyl or CH3SO
2
-; C
1
-C
4
-alkoxy-C
1
-C
8
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkinyl or C
3
-C
6
-cycloalkyl;
R
19
is hydrogen, C
1
-C
8
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkinyl; or
R
18
and R
19
together are C
4
- or C
5
alkylene, whereby one carbon atom may be replaced by oxygen or sulphur, or one or two carbon atoms may be replaced by —NR
20
-;
R
20
is hydrogen or C
1
-C
4
-alkyl;
m is 0 or 1; and
p signifies 0, 1 or 2,
as well as agronomically compatible salts and stereoisomers of these compounds.
The proviso a) denotes compounds of formula I, wherein 1, 2 or 3 of the ring members U, V, W/ and/or Z, independently of one another, are carbonyl, and one ring member which is adjacent thereto is the group
This group itself appears
only once in the compound of formula 1. Therefore, in the proviso a), “one” is the numeral.
In the above-mentioned definitions, halogen is understood to be iodine and preferably fluorine, chlorine and bromine.
The alkyl, alkenyl and alkinyl groups appearing in the definitions of the substituents may be straight-chain or branched, and the same applies also to the alkyl, alkenyl and alkinyl moiety of the alkylcarbonyl, alkoxyalkyl, alkylthio and alkylsulphonyl groups.
Alkyl groups denote for example methyl, ethyl, n-propyl, iso-propyl, n-butyt, sec.-butyl, iso-butyl, tert.-butyl, as well as the various isomeric pentyl, hexyl, heptyl and octyl radicals. Methyl, ethyl, n-propyl, iso-propyl and n-butyl are preferred.
Examples of alkenyls which may be mentioned are allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl and 2-hexenyl, preferably alkenyl radicals with a chain length of 3 to 5 carbon atoms.
Examples of alkinyls which may be mentioned are propargyl, 1-methylpropargyl, 3-butinyl, but-2-in-1-yl, 2-methylbut-3-in-2-yl, but-3-in-2-yl, 1 -pentinyl, pent-4-in-1 -yl and 2-hexinyl, preferably alkinyl radicals with a chain length of 3 to 5 carbon atoms.
The halogen-alkyl which may be considered are alkyl groups that are substituted by halogen once or many times, especially once to three times, whereby halogen signifies in detail iodine and especially fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichioroethyl, 2,2,2-trifluoroethyl and 2,2,2-trichloroethyl.
Alkylsulphonyl is for example methylsulphonyl, ethylsulphonyl, propylsulphonyl, isopropyl-sulphonyl, n-butylsulphonyl, iso-butylsulphonyl, sec.-butylsulphonyl and tert.-butylsulphonyl; preferably methylsulphonyl and ethylsulphonyl.
Halogen-alkylsulphonyl is for example fluoromethylsulphonyl, difluoromethylsulphonyl, trifluoromethylsulphonyl, chloromethylsulphonyl, trichlommethylsulphonyl, 2-fluoroethyl-sulphonyl, 2,2,2-trifluoroethylsulphonyl and 2,2,2-trichloroethylsulphonyl.
Alkylcarbonyl is especially acetyl and propionyl.
Alkoxy is for example methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec.-butoxy and tert.-butoxy.
Alkenyloxy is for example allyloxy, methallyloxy and but-2-en-1 -yloxy.
Alkinyloxy is for example propargyloxy and 1-methylpropargyloxy.
Alkoxyalkyl is for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, iso-propoxymethyl and iso-propoxyethyl.
Halogenalkoxy is for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy.
Of the alkenyl radicals that are substituted 1, 2 or 3 times by halogen, preference is given to those which have a chain length of 3 or 4 carbon atoms. The alkenyloxy groups may be substituted by halogen at saturated or unsaturated carbon atoms.
The halogen-alkenyloxy which may be considered are alkenyloxy groups that are substituted by halogen once or many times, whereby halogen signifies in detail bromine, iodine and especially fluorine and chlorine, for example 2- and 3-fluoropropenyloxy, 2- and 3-chloropropenyloxy, 2- and 3-bromopropenyloxy, 2,3,3-trifluoropropenyloxy, 2,3,3-trichioropropenyloxy, 4,4,4-trifluoro-but-2-en-1 -yloxy and 4,4,4-trichloro-but-2-en-1 -yloxy.
Alkylthio signifies for example methylthio, ethylthio, propylthio and butylthio, as well as the branched isomers thereof.
Phenyl or benzyl per se, or as part of a substituent, such as phenylalkyl or benzylamino, exist in optionally substituted form, in which case the substituents may be in ortho-, meta- or para-position. Substituents are e.g. C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen, C
1
-C
4
-halogen-alkyl or C
1
-C
4
-halogen-alkoxy.
Corresponding significances may also be assigned to the substituents in compound definitions, such as alkyl-Y, halogen-alkyl-Y, alkoxy-alkyl-Y, alkenyloxy-alkyl-Y, phenyl-alkyl-Y, alkenyl-Y, halogen-alkenyl-Y, phenyl-alkenyl-Y, phenyl-alkinyl-Y, halogen-alkyl-X-alkyl and alkyl-S(O)-alkyl.
In the definition of alkylcarbonyl, the carbonyl carbon atom is not included in the lower and upper numeric limits for carbon atoms respectively indicated.
Preference is given to compounds of formula I, wherein R
17
is hydrogen or C
1
-C
8
-alkyl, and R
18
is hydrogen, C
1
-C
8
-alkyi, phenyl, phenyl-C
1
-C
8
-alkyl, whereby the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH
3
, C
1
-CA-alkyl or CH
3
SO
2
-; C
1
-C
4
-al

Affiliated with

Also associated with

Rating

Herbicidal composition does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Herbicidal composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidal composition will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2452192