Substituted herbicide tetrazolinonecarboxylic acid amides

Details Substituted herbicide tetrazolinonecarboxylic acid amides Substituted herbicide tetrazolinonecarboxylic acid amides

2000-02-01

2001-08-21

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S261000, C504S269000, C504S271000, C546S268400, C548S245000, C548S214000, C548S251000

Reexamination Certificate

active

06277790

ABSTRACT:

The present invention relates to novel substituted tetrazolinonecarboxamides of the formula I
where the variables have the following meaning:
Het is oxetan-3-yl, thietan-3-yl, tetrahydrofuran-3-yl, furan-3-yl, tetrahydrothiophen-3-yl, thiophen-3-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-thiopyran-3-yl, tetrahydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4-yl,
where the abovementioned heterocycles may carry one or two substituents selected from a group consisting of halogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
1
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, cyano-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C-C
4
-alkyl, C
1
-C
4
-haloalkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, C
1
C
4
-haloalkylsulfonyl-C
1
-C
4
-alkyl, C
2
-C
6
-alkenyl, cyano-C
3
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, C
5
-C
8
-cycloalkenyl, C
5
-C
8
-cycloalkenyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C
1
-C
4
-alkyl, which may contain a carbonyl or thiocarbonyl ring member;
where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C
1
-C
4
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-haloalkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy and C
1
-C
4
-haloalkylcarbonyloxy; heterocyclyl- C
1
-C
4
-alkyl which may contain a carbonyl or thiocarbonyl ring member,
the cycloalkyl rings, phenyl rings or heterocyclyl rings being with or without substitution, and herbicidal compositions comprising the tetrazolinonecarboxamides I.
R
2
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C
1
-C
4
-alkyl, which may contain a carbonyl or thiocarbonyl ring member,
where the cycloalkyl rings, phenyl rings or heterocyclyl rings are in each case unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-haloalkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy and C
1
-C
4
-haloalkylcarbonyloxy.
Furthermore, the invention relates to processes for preparing substituted tetrazolinonecarboxamides of the formula I, to their use as herbicides, to herbicidal compositions comprising the substituted tetrazolinonecarboxamides of the formula I as active substances, to processes for preparing these herbicidal compositions and to methods for controlling undesirable vegetation.
Herbicidally active tetrazolinonecarboxamides are described, for example, in EP-A-146 279. Tetrazolinonecarboxamides which are cycloalkyl- substituted at the amide nitrogen and have herbicidal activity are disclosed, for example, in EP-A-692 482, EP-A-672 663, EP-A-612 735, EP-A-732 326, EP-A-202 929, EP-A-712 850, EP-A-711 761, EP-A-708 097, EP-A-728 750, EP-A-695 748, EP-A-733 625, EP-A-733 624.
However, the herbicidal properties of the known herbicides with respect to harmful plants are not entirely satisfactory.
It is an object of the present invention to provide novel herbicidally active compounds which allow better control of undesirable plants.
We have found that this object is achieved by the present substituted tetrazolinonecarboxamides of the formula I and their herbicidal activity.
Furthermore, we have found herbicidal compositions comprising the compounds I and having very good herbicidal activity. Furthermore, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. This invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The organic moieties mentioned for the substituents Het, R
1
, R
2
or as radicals on cycloalkyl, phenyl or heterocyclyl rings are collective terms for the individual listings of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, cyanoalkyl, phenylalkyl, heterocyclylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, alkoxycarbonyl, alkenyl, haloalkenyl, cyanoalkenyl and alkynyl groups can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.
The term halogen represents in each case fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
C
1
-C
4
-alkyl: CH
3
, C
2
H
5
, n-propyl, CH(CH
3
)
2
, n-butyl, 1-methylpropyl, 2-methylpropyl or C(CH
3
)
3
; in particular CH
3
or C
2
H
5
;
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl as mentioned above, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; in particular CH
3
, C
2
H
5
, n-propyl, CH(CH
3
)
2
, n-butyl, C(CH
3
)
3
, n-pentyl or n-hexyl;
C
1
-C
4
-haloalkyl: a C
1
-C
4
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example CH
2
Cl, CH(Cl)
2
, C(Cl)
3
, CH
2
F, CHF
2
, CF
3
, CHFCl, CF(Cl)
2
, CF
2
Cl, CF
2
Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl; in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 1,2-dichloroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl;
C
1
-C
6
-haloalkyl: C
1
-C
6
-alkyl as mentioned above, which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e. for example one of the abovementioned C
1
-C
4
-haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, 6,6,6-trichlorohexyl or dodecafluorohexyl; in particular fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
C
3
-C
8
-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; in parti

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