Arylalkyltriazole derivatives and their use as herbicides

Details Arylalkyltriazole derivatives and their use as herbicides Arylalkyltriazole derivatives and their use as herbicides

1999-07-16

2001-03-13

Morris, Patricia L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S263400, C548S263600

Reexamination Certificate

active

06200935

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel arylalkyl compounds, to processes for their preparation, to novel intermediates and to their use as herbicides.
BACKGROUND OF THE INVENTION
Some arylalkyl compounds have already been disclosed in the (patent) literature as potential herbicides (cf. DE 2526358, U.S. Pat. No. 4,249,934, U.S. Pat. No. 5,262,390, WO 9621647). However, these compounds have not attained any practical importance worth mentioning.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel arylalkyl compounds of the general formula (I)
in which
m represents the numbers 0 to 5,
n represents the numbers 0 to 4,
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen or optionally substituted alkyl,
R
2
represents hydrogen or optionally substituted alkyl,
X represents hydroxyl, mercapto, amino, hydroxyamino, nitro, formyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, halogen, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl,
Y represents nitro, carboxyl, cyano, carbamoyl, thiocarbamoyl, halogen, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, and
Z represents one of the groupings below
 in which
R
3
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkinyl,
R
4
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkinyl,
R
5
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkinyl,
R
6
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkinyl,
R
7
represents hydrogen, amino, cyano, formyl, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkinyl or cycloalkyl, and
R
8
represents hydrogen, halogen, or represents an in each case optionally cyano-, halogen- or alkoxy-substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl amino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkinyl, alkinyloxy, alkinylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino, or together with R
7
represents alkanediyl (alkylene).
The novel arylalkyl compounds of the general formula (I) are obtained when
(a) 4-aryl-semicarbazides of the general formula (II)
 in which
m, n, Q, R
1
, R
2
, R
3
, R
4
, X and Y are each as defined above and
R represents alkyl
are cyclocondensed, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, subsequently electrophilic or nucleophilic substitution reactions within the scope of the definition of the substituents are carried out in a customary manner on the product,
 or when
(b) 1-aryl-semicarbazides of the general formula (III)
 in which
m, n, Q, R
1
, R
2
, R
5
, R
6
, X and Y are each as defined above
are reacted with phosgene, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, subsequently electrophilic or nucleophilic substitution reactions within the scope of the definition of the substituents are carried out in a customary manner on the product,
 or when
(c) halogenoarenes of the general formula (IV)
 in which
m, n, Q, R
1
, R
2
, X and Y are each as defined above and
X
1
represents halogen
are reacted with heterocyclic compounds of the general formula (V)
Z—H (V)
 in which
Z is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, subsequently electrophilic or nucleophilic substitution reactions within the scope of the definition of the substituents are carried out in a customary manner on the product,
 or when
(d) arylalkyl halides of the general formula (VI)
 in which
m, R
1
, R
2
and X are each as defined above and
X
2
represents halogen
are reacted with are each of the general formula (VII)
 in which
n, Y and Z are each as defined above and
Q
1
represents oxygen or sulphur,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, subsequently electrophilic or nucleophilic substitution reactions within the scope of the definition of the substituents are carried out in a customary manner on the product.
The compounds of the general formula (I) can also be converted by other customary methods into other compounds of the general formula (I) according to the above definition, for example by customary conversions of carboxylic acid groupings or their derivatives (for example X: COOH→COOCH
3
, COOCH
3
→CONH
2
, CONH
2
→CN, CN→CSNH
2
), by alkylation reactions (for example R
3
, R
4
, R
5
, R
6
: H→CH
3
or CHF
2
) or by oxidation (for example Q: S→SO or SO
2
)—cf. also the Preparation Examples.
The novel substituted arylalkyl compounds of the general formula (I) have strong herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, in particular represents fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
m represents the numbers 0 to 4,
n represents the numbers 0 to 3,
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen or represents optionally halogen-substituted alkyl having 1 to 6 carbon atoms,
R
2
represents hydrogen or represents optionally halogen-substituted alkyl having 1 to 6 carbon atoms,
X represents hydroxyl, mercapto, amino, hydroxyamino, nitro, formyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, halogen, or represents an in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
Y represents nitro, carboxyl, cyano, carbamoyl, thiocarbamoyl, halogen, or represents an in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, and
Z represents one of the groupings below
 in which
R
3
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted radical from the series alkyl, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms,
R
4
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted radical from the series alkyl, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms,
R
5
represents hydrogen, cyano, formyl, or represents an in each case optionally cyano-, halogen- or C
1
-C
4
-al

Affiliated with

Also associated with

Rating

Arylalkyltriazole derivatives and their use as herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Arylalkyltriazole derivatives and their use as herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Arylalkyltriazole derivatives and their use as herbicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2494341