Substituted carbamoyl triazoles and their use as herbicides

Details Substituted carbamoyl triazoles and their use as herbicides Substituted carbamoyl triazoles and their use as herbicides

1999-03-17

2001-07-24

Oswecki, Jane C. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S271000, C504S273000, C504S274000, C504S288000, C504S294000, C548S215000, C548S240000, C548S263200, C548S264200, C548S266600, C548S266800

Reexamination Certificate

active

06265352

ABSTRACT:

DESCRIPTION
The present invention relates to novel substituted carbamoyltriazoles of the formula I
where:
R
1
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
2
is C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy or a radical listed under R
1
; or
R
1
and R
2
together form a C
2
-C
5
-alkanediyl radical which may carry one to three substituents selected from the group consisting of halogen and C
1
-C
6
-alkyl and, in the case of a C
4
-C
5
-alkanediyl radical, a CH
2
group may be replaced by oxygen or a group NH or N-C
1
-C
6
-alkyl;
R
3
,R
4
and R
5
are each hydrogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, phenyl or benzyl, where the last two substituents may be partially or fully halogenated and may carry one to three of the following groups:
nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkoxycarbonyl;
A is an unsubstituted or substituted saturated or partially unsaturated five or six-membered heterocycle containing one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen;
n is 0, 1 or 2;
with the proviso that A is not 1,3-dioxolan-2-yl or 1,3-dioxan-2-yl;
and the agriculturally useful salts of I.
Furthermore, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to their use for controlling harmful plants.
Carbamoyltriazoles are known from the literature, for example from EP-A 140 194, EP-A 422 369, U.S. Pat. No. 5,308,830, JP-A 07 053 529 and JP-A 61 178 930.
However, the herbicidal properties of the prior art compounds and the compatibility with crop plants are not fully satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties and also novel intermediates, the triazoles of the formula II.
We have found that this object is achieved by the substituted carbamoyltriazoles of the formula I and their herbicidal activity and also by intermediates and processes for preparing the compounds I.
This invention further provides herbicidal compositions which comprise the compounds I and which have a very good herbicidal activity. It additionally provides processes for the preparation of 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 the pure enantiomers or diastereomers as well as their mixtures.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt as a rule not being important. The salts of those cations or the acid addition salts of those acids are generally suitable whose cations or anions, respectively, do not interfere with the herbicidal activity of the compounds I. Suitable cations are in particular ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium which, if desired, may carry one to four C
1
-C
4
-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri (C
1
-C
4
-alkyl)sulfonium, and sulfoxonium ions, preferably tri (C
1
-C
4
-alkyl) sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Preference is given to substituted carbamoyltriazoles of the formula I
where:
R
1
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
2
is C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy, and the radicals mentioned under R
1
; or
R
1
and R
2
together form a C
2
-C
5
-alkanediyl radical which may carry one to three substituents selected from the group consisting of halogen and C
1
-C
6
-alkyl and, in the case of a C
4
-C
5
-alkanediyl radical, a CH
2
group may be replaced by oxygen or a group NH or N-C
1
-C
6
-alkyl;
R
3
,R
4
and R
5
are each hydrogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, phenyl or benzyl where the last two substituents may be partially or fully halogenated and may carry one to three of the following groups:
nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkoxycarbonyl;
A is a five-membered saturated or partially unsaturated heterocycle which contains one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen and which may carry, attached to carbon, one to three radicals selected from the group consisting of R
6
, R
7
and R
8
, and where any ring nitrogen may, independently of any other(s), carry a radical R
10
; or
is a six-membered saturated or partially unsaturated heterocycle which contains one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen and which may carry, attached to carbon, one to four radicals selected from the group consisting of R
6
, R
7
, R
8
and R
9
, and where any ring nitrogen may, independently of any other(s), carry a radical R
10
;
R
6
,R
7
,R
8
and R
9
are each cyano, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, phenyl or benzyl where the last two substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkoxycarbonyl;
R
10
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, phenyl or benzyl where the last two substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkoxycarbonyl;
n is 0, 1 or 2;
with the proviso that A is not 1,3-dioxolan-2-yl or 1,3-dioxan-2-yl;
and the agriculturally useful salts of I.
The organic moieties mentioned for the substituents R
1
-R
10
or as radicals at phenyl rings are collective terms for individual listings of the individual group members. All hydrocarbon chains, ie. all the alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, cycloalkyl, alkanediyl, alkenyl and alkynyl moieties can be straight-chain or branched. If not stated otherwise, halogenated substituents preferably carry one to five identical or different halogens. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Other examples of meanings are:
C
1
-C
4
-alkyl and the alkyl moieties of C
1
-C
4
-alkylcarbonyl: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl, and the alkyl moieties of C
1
-C
6
-alky

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