BACKGROUND OF THE INVENTION 
The present invention relates generally to new benzylcarbamoylpyridine 
derivatives and to processes for their preparation, and their use and 
application in herbicidal compositions and methods for the crop selective 
destruction of weeds in crops, in particular, cotton, sunflower and soya 
crops. 
Substituted related carbamoyl pyridines having various substituents thereon 
have heretofore been prepared and proposed for use in a number of 
different ultimate applications. 
For example, German Patent Application No. B-1,116,669 describes the 
preparation of 3-(alpha-alkylbenzyl-carbamoylpyridines, which can be used 
as medicaments, by reaction of nicotinic acid (or pyridine-3-carboxylic 
acid) with a benzylamine or the formula: 
##STR2## 
in which Z represents a hydrogen or halogen atom or a lower alkyl or 
alkoxy radical and "alkyl" represents an alkyl radical containing at least 
two carbon atoms. 
European Patent Application No. A-0,044,262 describes various aniline 
derivatives, including several 3-N-(phenyl)-carbamoyl-2,6-dimethylpyridine 
derivatives, as herbicides. 
The compounds according to the present invention are different from those 
described in these two patent applications. Most particularly, in addition 
to their structural differences, the herbicidal activity of the present 
compounds is very substantially superior to that of the analogous 
3-N-(phenyl)-carbamoyl-2,6-dimethylpyridines described, for example, in 
European Patent Application No. 0,004,263. 
SUMMARY OF THE INVENTION 
It is, therefore, a primary object of the present invention to afford novel 
substituted benzylcarbamoylpyridines which possess outstanding herbicidal 
activity. 
It is a further object of the present invention to provide novel processes 
for obtaining the new herbicidally active compounds of the invention. 
A still further object of the present invention is to provide compositions 
and formulations and methods for using the compounds and formulated 
compositions comprising benzylcarbamoylpyridines as pre- and post-emergent 
crop selective herbicides. 
DESCRIPTION OF THE PREFERRED EMBODIMENTS 
The herbicidally effective compounds of the present invention correspond to 
the general formula (I) 
##STR3## 
in which: R.sub.1, independently, represents a halogen atom, an alkyl 
radical containing from 1 to 6 carbon atoms, which is optionally 
substituted by one or more halogen atoms (e.g. the trifluoromethyl), or an 
alkoxy radical containing from 1 to 4 carbon atoms; 
R.sub.2 and R.sub.3, which are identical or different, represent an alkyl 
radical containing from 1 to 3 carbon atoms, an alkoxy radical containing 
from 1 to 4 carbon atoms or an alkoxyalkyl radical containing from 2 to 8 
carbon atoms; 
R.sub.4 represents a radical selected from the group consisting of: acyl 
radicals (preferably alkanoyl radicals containing from 1 to 6 carbon atoms 
or benzoyl radicals optionally substituted e.g. by one or more halogen 
atoms), azidomethyl radicals, alkoxycarbonylmethyl radicals containing 
from 3 to 8 carbon atoms, hydroxyalkyl radicals containing from 2 to 5 
carbon atoms; halogenoalkyl radicals containing from 2 to 5 carbon atoms, 
alkyl radicals containing from 1 to 4 carbon atoms, which may be straight 
or branched and which are optionally substituted by a heterocyclic radical 
containing from 5 to 6 ring members and from 1 to 3 heteroatoms selected 
from oxygen, sulfur and nitrogen atoms, alkynyloxyalkyl radicals 
containing from 4 to 8 carbon atoms or a vinyl radical; and wherein n is 
an interger from 0 to 5 inclusive, it being understood that, where several 
R.sub.1 substituents are present, these substituents can be either 
identical or different. 
The compounds corresponding to the formula (I) can form salts with suitable 
acids, which can be either mineral acids such as e.g. hydrochloric acid, 
sulfuric acid and phosphoric acid, or organic acids such as e.g. succinic 
acid, fumaric acid, oxalic acid, benzoic acid and tartaric acid. These 
various salts are also included within the scope of the present invention 
and are referred to herein as "agriculturally acceptable" salts. 
Among the preferred compounds according to the formula (I), having 
especially outstanding herbicidal properties are those wherein: 
n is equal to 0, 1, 2 or 3, 
R.sub.1 represents a halogen atom or a methyl radical, 
R.sub.2 represents a methyl radical, 
R.sub.3 represents a methyl or methoxymethyl radical, and 
R.sub.4 represents an alkanoyl radical containing from 1 to 6 carbon atoms, 
an azidomethyl radical, a halogenoalkyl radical containing from 2 to 5 
carbon atoms or an alkyl radical containing from 1 to 3 carbon atoms, 
and the agriculturally acceptable salts of these compounds. 
Another preferred subgroup of the compounds are those according to the 
formula (I) in which: 
n is equal to 0, 
R.sub.2 and R.sub.3 represent a methyl radical, and 
R.sub.4 represents an alkanoyl radical containing from 1 to 3 carbon atoms, 
an azidomethyl radical, a halogenoalkyl radical containing from 2 to 4 
carbon atoms or an alkyl radical containing from 1 to 3 carbon atoms, 
and the agriculturally acceptable salts of these compounds. 
The compounds of the formula (I) have an asymmetrically substituted carbon 
atom in the alpha position to the phenyl nucleus and can therefore be in 
different racemic forms or in the form of optical antipodes. These 
different optically active or racemic isomeric forms are included within 
the scope of the invention. 
Among these different forms, the optical isomers having the same optical 
configuration as (S)-alpha-methylbenzylamine are generally preferred for 
their herbicidal properties. 
The compounds according to the formula (I) can be prepared by the processes 
a-i described below and analogous processes which will be apparent to 
those skilled in the art. 
In the description which follows, for greater convenience, the letter R 
will represent the radical of the formula (II) 
##STR4## 
R.sub.1, R.sub.2, R.sub.3 and n having the same meanings as in formula (I) 
before. 
PROCESS a 
The compounds according to the formula (I) in which R.sub.4 represents an 
acyl radical and which therefore correspond to the formula (III) 
EQU R--CO--R.sub.5 (III) 
in which R.sub.5 represents an organic radical (preferably an optionally 
substituted alkyl or phenyl radical) and R has the same meaning as in the 
formula (II), can be obtained by reacting an organomagnesium compound of 
the formula (IV) 
EQU R.sub.5 MgX (IV) 
in which R.sub.5 has the same meaning as in the formula (III) and X 
represents a halogen atom (preferably bromine or iodine), with an 
alkoxycarbonylpyridine of the formula (V) 
EQU R--COO--R.sub.6 (V) 
in which R has the same meaning as above and R.sub.6 represents an alkyl 
radical containing from 1 to 6 carbon atoms (preferably methyl or ethyl), 
and then by hydrolysing the halogenomagnesium alcoholate formed as an 
intermediate. 
The reaction of (IV) with (V) is advantageously carried out in an anhydrous 
medium, in an ether such as diethyl or isopropyl ether, tetrahydrofuran or 
a mixture of these ethers. 
The hydrolysis of the halogenomagnesium alcoholate is advantageously 
carried out by treating the reaction mixture with an aqueous solution of 
ammonium chloride or a dilute mineral acid such as hydrochloric acid or 
sulfuric acid. 
The alkoxycarbonylpyridine (V) can be obtained by dehydrogenating the 
3-benzylcarbamoyl-5-alkoxycarbonyl-1,4-dihydropyridine of the formula (VI) 
##STR5## 
in which R.sub.1, R.sub.2, R.sub.3 and n have the same meanings as in the 
formula (I) and R.sub.6 has the same meaning as in the formula (V). 
This dehydrogenation can be carried out by reacting an oxidizing agent, 
such as KMnO.sub.4, with the compound (VI). This compound (VI) is itself 
obtained by a method analogous to that described in European Patent 
Application No. 81/420,106.7 for the preparation of 
1,4-dihydro-3-N-(2,6-diethylphenyl)-carbamoyl-5-ethoxycarbonyl-2,6-lutidin 
e. 
PROCESS b 
The compounds according to the formula (I) in which R.sub.4 represents an 
azidomethyl radical and which therefore correspond to the formula (VII) 
EQU R--CH.sub.2 --N.sub.3 (VII) 
in which R has the same meaning as in the formula (II), can be obtained by 
reacting an alkali metal azide, such as sodium azide, NaN.sub.3, with a 
chloromethylpyridine of the formula (VIII) 
EQU R--CH.sub.2 --Cl (VIII) 
in which R has the same meaning as above. 
The reaction is advantageously carried out in an inert organic solvent 
medium at a temperature of the order of 10.degree. to 40.degree. C. 
It is preferably carried out in a solvent mixture capable of dissolving 
both the reactants, e.g. water/lower alkanol mixtures or a DMSO/water 
mixture, above ordinary temperature. 
The chloromethylpyridine (VIII) can be obtained from the ester of the 
formula (XVII) 
EQU R--COO--R.sub.6 (XVII) 
in which R has the same meaning as above and R.sub.6 has the same meaning 
as in the formula (V), by reducing this ester to an alcohol of the formula 
EQU R--CH.sub.2 --OH 
and, finally, chlorinating this alcohol to give the chloromethylpyridine 
(VIII). 
The ester of the formula (XVII) can be prepared by the method described in 
process (a) described above. 
PROCESS c 
The compounds according to the formula (I) in which R.sub.4 represents a 
methyl radical substituted by a heterocyclic radical (e.g. the triazolyl 
radical) can be obtained by reacting the chloromethylpyridine of the 
formula (VIII), in which R has the same meaning as in the formula (II), 
with the heterocyclic compound of the formula AH, in which A represents a 
heterocyclic radical such as the triazolyl radical. 
The reaction is advantageously carried out in a polar aprotic solvent such 
as dimethylformamide, dimethyl sulfoxide or dimethylacetamide, in the 
presence of an anion-forming agent of sufficiently high basicity to form 
the heterocyclic anion, at a temperature generally of between 10.degree. 
and 50.degree. C., preferably of about 25.degree. C. Sodium hydride or 
potassium hydride is preferably used as the anion-forming agent. 
The chloromethylpyridine can be prepared by the method described in process 
b. 
PROCESS d 
The compounds according to the formula (I) in which R4 represents an 
alkoxycarbonylmethyl radical containing from 3 to 8 carbon atoms and which 
correspond to the formula (X) 
EQU R--CH.sub.2 --COOR.sub.6 (X) 
in which R has the same meaning as in the formula (II) and R.sub.6 
represents an alkyl radical containing from 1 to 6 carbon atoms, can be 
obtained by reacting a lower alkanol with the cyanomethylpyridine of the 
formula (XI) 
EQU R--CH.sub.2 --CN (XI) 
in which R has the same meaning as above. 
The reaction is advantageously carried out in the presence of a mineral 
acid, in solvent mixtures capable of dissolving the reactants present, 
such as e.g. lower alcohols, at a temperature generally of the order of 
ambient temperature. The cyanomethylpyridine (XI) can be obtained by 
reacting sodium cyanide with the chloromethylpyridine corresponding to the 
formula (VIII). This reaction is advantageously carried out in an 
aqueous-alcoholic medium at or above ordinary temperature. The 
chloromethylpyridine (VIII) can be prepared by the method described above 
in process b. 
PROCESS e 
The compounds according to the formula (I) in which R.sub.4 represents a 
hydroxyalkyl radical can be prepared by one or other of the processes 
described below: 
The compounds according to the formula (I) in which R.sub.4 represents a 
beta-hydroxyethyl radical and which therefore correspond to the formula 
(XII) 
EQU R--CH.sub.2 --CH.sub.2 --OH (XII) 
in which R has the same meaning as in the formula (II), can be obtained 
from the alkoxycarbonylmethylpyridine (X)--the preparation of which is 
described in process d--by reducing this compound to give the 
corresponding primary alcohol. 
This conversion can be carried out by the usual methods which make it 
possible to reduce carboxylic acid esters to alcohols, e.g. by catalytic 
hydrogenation, generally at elevated temperature or under high pressure, 
or by using a reducing agent such as lithium aluminium hydride. 
This reduction is advantageously carried out by means of lithium aluminium 
hydride, the reaction being carried out in an anhydrous medium, in an 
inert organic solvent such as ethers, at a temperature generally of 
between 0.degree. and 30.degree. C., preferably of the order of 15.degree. 
C. 
The compounds according to the formula (I) in which R represents an 
alpha-hydroxyalkyl radical and which therefore corresponds to the formula 
(IX): 
##STR6## 
in which R has the same meaning as in the formula (II) and R.sub.8 
represents an alkyl radical containing from 1 to 4 carbon atoms, can be 
obtained by reducing an alkanoylpyridine corresponding to the formula 
(XVIII): 
EQU R--CO--R.sub.8 (XVIII) 
in which R and R.sub.8 have the same meanings as above. 
This reduction is carried out under the same conditions as the reduction of 
the alkoxycarbonylmethylpyridine (X) to give the compound (XII). 
The starting alkanoylpyridine can be prepared by the method described in 
process a. 
Other hydroxyalkyl derivatives may also be prepared using, as the starting 
material, the beta-hydroxyethyl derivative (XII) or the 
alpha-hydroxylalkyl derivative (IX) and converting the hydroxyl group to a 
hydroxymethyl group using the following sequence of reactions: (1) 
replacing the hydroxyl group with a chlorine atom using the method of 
process f; (2) replacing the chlorine atom with an alkoxycarbonyl group 
using the two step method of process D and (3) reducing the alkoxy 
carbonyl group to a hydromethyl group using the method of process e. 
PROCESS f 
The compounds according to the formula (I) in which R represents a 
halogenoalkyl radical containing from 2 to 5 carbon atoms can be obtained 
by halogenating hydroxyalkylpyridines, the preparation of which has been 
described in process e. 
When the hydroxyalkylpyridine corresponds to the formula (XII) or to the 
formula (IX), the halogenoalkylpyridine obtained corresponds to the one or 
other of the formulae (XIII) and (XIX) below: 
##STR7## 
in which R has the same meaning as in the formula (II), R.sub.8 has the 
same meaning as in the formula (XVIII) and X represents a halogen atom, 
preferably the chlorine atom. 
This conversion can be carried out by the usual methods which make it 
possible to replace the hydroxyl group by a halogen atom, e.g. by means of 
inorganic oxoacid chlorides such as SOCl.sub.2 or POCl.sub.3. 
This halogenation is advantageously carried out by means of SOCl.sub.2, the 
reaction being carried out in an organic solvent such as methylene 
chloride, at a temperature of the order of about 10.degree. to 40.degree. 
C. 
PROCESS g 
The compounds according to the formula (I) in which R.sub.4 represents a 
straight or branched chain alkyl radical containing from 1 to 4 carbon 
atoms and which therefore correspond to the formula (XIV) 
##STR8## 
in which R has the same meaning as in the formula (II) and p is equal to 
an integer from 1 to 4, can be obtained by reducing the 
chloroalkylpyridine corresponding to the formula (XVI): 
##STR9## 
in which R and p have the same meanings as above, by means of a reducing 
agent which makes it possible to replace the chlorine atom by a hydrogen 
atom. 
This conversion is advantageously carried out using sodium borohydride as 
the reducing agent, the reaction being carried out in a polar aprotic 
inert solvent such as dimethylformamide or dimethylacetamide, at a 
temperature of the order of 20.degree. to 50.degree. C. The 
chloroalkylpyridine of the formula XVI can be prepared by the method 
described above in process b, or by process f. 
PROCESS h 
The compounds according to the formula (I) in which R.sub.4 represents the 
vinyl radical can be obtained by dehydrochlorinating the 
chloroethylpyridine (XIII), the preparation of which is described in 
process f. 
This removal of HCl is advantageously carried out by reaction with sodium 
hydride, in the presence of the anion of 1,2,4-triazole acting as a 
removing agent, in a polar aprotic solvent such as dimethylformamide, at 
ambient temperature. 
PROCESS i 
The compounds according to the formula (I) in which R.sub.4 represents an 
alkynyloxyalkyl radical and which therefore correspond to the formula 
(XV): 
##STR10## 
in which R has the same meaning as in the formula (II), R.sub.7 represents 
an alkynyl radical containing from 3 to 5 carbon atoms and p has the same 
meaning as in the formula (XIV), can be obtained by reacting an alkali 
metal salt of the alcohol R.sub.7 --OH, the said salt being formed in situ 
if appropriate, with the chloroalkylpyridine of the formula (XVI), the 
preparation of which is described above in process g. The reaction is 
advantageously carried out in anhydrous tetrahydrofuran at about 
20.degree. C.

The examples below, which are given without implying a limitation, further 
illustrate the invention and methods of using same consistent with the 
objectives described above. 
The structures of the compounds were confirmed by infra-red spectrometry 
and/or by nuclear magnetic resonance spectrometry (NMR); the NMR spectra 
were run at 60 megahertz in dimethylformamide, with hexamethyldisiloxane 
as the reference standard. 
The term "2,6-lutidine" used in these examples is synonymous with 
"2,6-dimethylpyridine". 
EXAMPLE 1 
Preparation of (S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-acetyl-2,6-lutidine 
(compound number 1), of the formula 
##STR11## 
Magnesium (480 mg; 20 millimoles) is introduced into a 100 ml three-necked 
round-bottomed flask fitted with a central mechanical stirrer, a dropping 
funnel, a condenser and a thermometer. Methyl iodide (3 g; 21 millimoles) 
in anhydrous ethyl ether (25 ml) is run in and the mixture is stirred 
until the magnesium has disappeared. After cooling to 25.degree. C., 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-methoxycarbonyl-2,6-lutidine (2.2 
g; 7 millimoles) in anhydrous tetrahydrofuran (25 ml) is run in. The 
reaction is exothermic. The temperature of the medium rises to 45.degree. 
C. After stirring for one hour, the medium is treated with a 5% strength 
aqueous solution of ammonium chloride (50 ml). 
The organic phase is decanted, washed with water, dried over sodium sulfate 
and concentrated. After chromatography on silica (200 g) eluted with a 
mixture of equal proportions of ethyl acetate and hexane, the expected 
product (compound No. 1) (1.25 g) is obtained in the form of a white 
powder. 
Yield: 60%. 
M.p.: 128.degree. C. 
IR spectrum: frequency of the carbonyl group: 1693 cm.sup.-1. 
The (S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-methoxycarbonyl-2,6-lutidine 
used as the starting material was obtained by reacting KMnO.sub.4 with 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-methoxycarbonyl-2,6-dimethyl-1,4- 
dihydropyridine, itself obtained by reacting formaldehyde with an 
appropriate aminoethylene derivative and an appropriate N-acetylamide, by 
a process analogous to that described in European Pat. No. 0,044,262 for 
3-phenylcarbamoyl-5-methoxycarbonyl-1,4-dihydro-2,6-lutidine. 
EXAMPLE 2 
(S)-3-N-(alpha-Methylbenzyl)-carbamoyl-5-propionyl-2,6-lutidine (compound 
No. 2), of the formula 
##STR12## 
was prepared starting from 
(S)-3-N-(alpha-methylbenzyl-carbamoyl-5-methoxycarbonyl-2,6-lutidine and 
ethylmagnesium iodide, the reaction being carried out under the conditions 
indicated in the previous example. 
Yield: 47%. 
M.p.: 120.degree. C. 
IR spectrum: frequency of the carbonyl group: 1695 cm.sup.-1. 
EXAMPLE 3 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-azidomethyl-2,6-lutidine 
(compound No. 3), of the formula 
##STR13## 
Anhydrous tetrahydrofuran (500 ml) is introduced into a 2 liter 
three-necked round-bottomed flask fitted with a dropping funnel, a central 
mechanical stirrer, a condenser surmounted by a CaCl.sub.2 drying tube, 
and a thermometer. Lithium aluminium hydride (14 g) is added in small 
portions. The reaction medium is cooled to 0.degree. C. A solution of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-methoxycarbonyl-2,6-lutidine (50 
g; 160 millimoles) in anhydrous tetrahydrofuran (300 ml) is run in slowly 
at between 0.degree. and 10.degree. C. After the addition has ended, the 
reaction medium is heated to 30.degree. C. and stirred for 45 minutes at 
this temperature. 
After hydrolysis and extraction, a yellow product (45 g) is obtained, which 
is purified by recrystallization from ethyl acetate (300 ml). This gives 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-hydroxymethyl-2,6-lutidine (42 g) 
of the formula: 
##STR14## 
Yield: 90%. 
M.p.: 143.degree. C. 
IR spectrum: 3400 cm.sup.-1, 3250 cm.sup.-1 and 3150 cm.sup.-1 (OH group). 
NMR spectrum: Chemical shift of the methyl groups: 2.40 ppm and 2.70 ppm. 
Methylene chloride (1,800 ml) is run into a 4 liter three-necked 
round-bottomed flask fitted with a dropping funnel, a central mechanical 
stirrer, a condenser and a thermometer. The compound obtained in the 
previous step, i.e. 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-hydroxymethyl-2,6-lutidine (90 g; 
317 millimoles), is added. After dissolution, thionyl chloride (73 g; 613 
millimoles) is run in slowly. The reaction is slightly exothermic and the 
reaction medium is kept under reflux for 30 minutes after the evolution of 
gas has ended. 
After cooling, the medium is neutralized with 2N sodium hydroxide solution 
(380 ml). The organic phase is decanted, washed with water and dried over 
sodium sulfate. After concentration, this gives 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine (90 g) 
of the formula 
##STR15## 
M.p.: 165.degree. C. 
Yield: 94%. 
NMR spectrum: Chemical shifts of the methyl groups: 2.50 and 2.75 ppm. 
The compound obtained in the previous step, i.e. 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine (3.7 g; 
12 millimoles), and ethyl alcohol (120 ml) are introduced into a 250 ml 
conical flask. After dissolution, a solution of sodium azide (1 g; 15 
millimoles) in water (20 ml) is added. After 8 hours, the reaction medium 
is poured into water (150 ml) and extracted with methylene chloride 
(2.times.100 ml). The organic phase is washed with water, dried over 
sodium sulfate and concentrated. This gives a crude product (3.2 g). 
After filtration on silica (100 g) with a mixture of equivalent proportions 
of methylene chloride and acetone, the expected product (compound No. 3) 
(3 g) is obtained in the form of a white powder melting at 
124.degree.-125.degree. C. 
Yield: 80%. 
IR spectrum: 2075, 2095 and 2112 cm.sup.-1 (azido substituent). 
EXAMPLE 4 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-(1,2,4-triazolyl)-methyl-2,6-luti 
dine (compound No. 4), of the formula: 
##STR16## 
DMF (20 ml) and 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine (2 g; 
6.6 millimoles), the preparation of which has been described in Example 3, 
are introduced into 250 ml three-necked round-bottomed flask fitted with a 
dropping funnel, a central mechanical stirrer and a condenser surmounted 
by a calcium chloride drying tube. 
After dissolution, 1,2,4-triazole (480 mg) and 80% strength sodium hydride 
(500 mg; 16.6 millimoles) are added. 
When the reaction is complete, the reaction medium is poured into water 
(200 ml) and extracted with methylene chloride (2.times.50 ml). After the 
organic phase has been washed with water, dried over sodium sulfate and 
concentrated, the expected product (compound No. 4) (1.8 g) is obtained. 
M.p.: 145.degree. C. 
Yield: 81%. 
NMR spectrum: Chemical shifts of the methyl groups: 2.42 and 2.64 ppm. 
EXAMPLE 5 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-ethoxycarbonylmethyl-2,6-lutidine 
(compound No. 5), of the formula: 
##STR17## 
Absolute ethanol (100 ml) is run into a 500 ml one-necked round-bottomed 
flask fitted with a magnetic stirrer. It is cooled in ice, and sulfuric 
acid (80 ml) is run in slowly, followed by water (5 ml) and 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-cyanomethyl-2,6-lutidine (6.4 g; 
22 millimoles). 
After 90 minutes under reflux, the reaction medium is cooled and treated 
and sodium bicarbonate (110 g; 1.3 moles) in water (one liter). Extraction 
is carried out with methylene chloride (3.times.100 ml). After washing 
with water, the organic phase is dried and concentrated. The product 
obtained is chromatographed on silica (150 g). The expected product 
(compound No. 5) (4 g) is eluted with a mixture of equivalent proportions 
of acetone and hexane. 
Yield: 54%. 
M.p.: 135.degree. C. 
The (S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-cyanomethyl-2,6-lutidine was 
obtained by reacting sodium cyanide with 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine. 
EXAMPLE 6 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-beta-hydroxyethyl-2,6-lutidine 
(compound No. 6), of the formula: 
##STR18## 
Anhydrous tetrahydrofuran (250 ml) is run into a 1 liter three-necked 
round-bottomed flask fitted with a central mechanical stirrer, a dropping 
funnel and a reflux condenser surmounted by a calcium chloride drying 
tube. Lithium aluminium hydride (4.6 g; 0.12 mole) is then introduced, 
with stirring. A solution of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-ethoxycarbonylmethyl-2,6-lutidine 
(compound No. 5) (21 g; 62 millimoles) in anhydrous tetrahydrofuran (150 
ml) is then run in at between 5.degree. and 10.degree. C. The addition 
takes 2 hours. After the addition has ended, the mixture is stirred for a 
further 30 minutes at 30.degree. C. 
After cooling and hydrolysis, the organic phase is dried and concentrated. 
The product obtained is dissolved in toluene (500 ml) at boiling 
temperature. After cooling and filtration, the expected product (compound 
No. 6) (16.3 g) is obtained. 
M.p.: 116.degree. C. 
Yield: 88%. 
EXAMPLE 7 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-beta-chloroethyl-2,6-lutidine 
(compound No. 7), of the formula: 
##STR19## 
Methylene chloride (500 ml) is run into a 1 liter three-necked 
round-bottomed flask fitted with a central mechanical stirrer, a condenser 
and a thermometer, and 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-beta-hydroxyethyl-2,6-lutidine 
(compound No. 6) (15.2 g; 51 millimoles), the preparation of which is 
described in Example 6, is introduced. 
The mixture is heated under reflux until dissolution is complete, and 
cooled to about 30.degree. C., and thionyl chloride (10.3 g; 76 
millimoles) is added. After stirring for 2 hours at this temperature, the 
mixture is neutralized by slowly running in a saturated aqueous solution 
of sodium bicarbonate (300 ml). The organic phase is decanted, washed with 
water and dried over sodium sulfate. After concentration, the crude 
product is recrystallized from toluene. This gives the expected product 
(compound No. 7) (7.5 g). 
Yield: 46%. 
M.p.: 125.degree. C. 
NMR spectrum: Chemical shifts of the two methyls: 2.36 and 2.68 ppm. 
EXAMPLE 8 
Preparation of (S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-ethyl-2,6-lutidine 
(compound No. 8), of the formula: 
##STR20## 
In a 250 ml one-necked round-bottomed flask, 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-beta-chloroethyl-2,6-lutidine 
(compound No. 7) (3.4 g; 11 millimoles) is dissolved in dimethylformamide 
(20 ml). Sodium borohydride (1 g; 26 millimoles) is then added. After 
stirring for 4 hours at 50.degree. C., the mixture is cooled to 20.degree. 
C. and a solution of ammonium chloride (5 g) in water (100 ml) is added. 
Extraction is carried out with methylene chloride. After the usual 
treatment, the product obtained is chromatographed on silica (100 g). The 
expected product (compound No. 8) (1.7 g) is eluted with ethyl acetate. 
M.p.: 123.degree. C. 
Yield: 61%. 
NMR spectrum: Chemical shift of the three methyls: 0.76-2.35 and 2.70 ppm. 
EXAMPLE 9 
(S)-3-N-(alpha-Methylbenzyl)-carbamoyl-2,5,6-trimethylpyridine (compound 
No. 9), of the formula: 
##STR21## 
was prepared from 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine, the 
preparation of which is described in Example No. 3, the reaction being 
carried out by the method described in Example No. 8. 
M.p.: 136.degree. C. 
Yield: 87%. 
NMR spectrum: Chemical shifts of the three methyls: 1.83-2.26 and 2.69 ppm. 
EXAMPLE 10 
Preparation of (S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-vinyl-2,6-lutidine 
(compound No. 10), of the formula: 
##STR22## 
Dimethylformamide (25 ml) and 1,2,4-triazole (1.2 g; 17 millimoles) are 
introduced into a 100 ml one-necked round-bottomed flask. 80% strength 
sodium hydride (700 mg; 23 millimoles) and 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-beta-chloroethyl-2,6-lutidine 
(compound No. 7) (2 g; 6 millimoles) are added. 
After stirring for 8 hours at ambient temperature, the reaction medium is 
poured into water (200 ml and extracted with methylene chloride 
(2.times.100 ml). After decantation, the organic phase is washed with 
water and dried over sodium sulfate. The product obtained after 
concentration is chromatographed on silica (100 g). The expected product 
(compound No. 10) (1 g) is eluted with a mixture of equivalent proportions 
of ethyl acetate and hexane. 
M.p.: 121.degree. C. 
Yield: 56%. 
NMR spectrum: Chemical shifts of the two methyls: 2.36 ppm and 2.89 ppm. 
EXAMPLE 11 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-propargyloxymethyl-2,6-lutidine 
(compound No. 11), of the formula 
##STR23## 
Propargyl alcohol (8 g; 143 millimoles) and anhydrous tetrahydrofuran (130 
ml) are introduced into a 500 ml one-necked round-bottomed flask. 80% 
strength sodium hydride (4 g; 133 millimoles) is added slowly, with 
cooling at 20.degree. C. A solution of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-chloromethyl-2,6-lutidine (6 g; 
20 millimoles) in tetrahydrofuran (50 ml) is then run in. After stirring 
for 24 hours at ambient temperature, the reaction mixture is poured into 
water (500 ml) and neutralized with 4N hydrochloric acid (30 ml). 
Extraction is carried out with methylene chloride (2.times.100 ml). The 
organic phase is washed with water, dried and concentrated. This gives an 
oil (4 g), which is chromatographed on silica (200 g). The extracted 
product (compound No. 11) (2.1 g) is eluted with an 8/2 mixture of 
methylene chloride/acetone. 
M.p.: 105.degree. C. 
Yield: 33%. 
NMR spectrum: Chemical shift of the two methyls: 2.39 and 2.71 ppm. 
EXAMPLE 12 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-(1-chloropropyl)-2,6-lutidine 
(compound No. 12), of the formula: 
##STR24## 
(S)-3-N-(alpha-Methylbenzyl)-carbamoyl-5-(1-hydroxypropyl)-2,6-lutidine 
(5.2 g) is obtained from 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-ethylcarbonyl-2,6-lutidine 
(compound No. 2) (6.2 g) and lithium aluminum hydride (1.6 g), the 
reaction being carried out by the method described in Example 6. 
Yield: 83%. 
The expected product (compound No. 12) (2.7 g) is obtained from this 
compound (5.2 g) and thionyl chloride (2.7 g), the reaction being carried 
out by the method described in Example 7. 
Yield: 48%. 
EXAMPLE NO. 13 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-azidomethyl-2,6-lutidine 
hydrochloride (compound No. 13--hydrochloride of compound No. 3) 
A suspension of compound No. 3 (22 g) in 0.7N hydrochloric acid (102 ml) is 
stirred until dissolution is complete. After dissolution, the solvent is 
evaporated off under reduced pressure. This gives a crystalline product 
(2.4 g) melting at 165.degree. C. 
Yield: 97%. 
EXAMPLE NO. 14 
Preparation of 
(S)-3-N-(alpha-methylbenzyl)-carbamoyl-5-propionyl-2,6-lutidine sulfate 
(compound No. 14--sulfate of compound No. 2) 
Compound No. 2 (3.1 g) is dissolved in acetone (200 ml), and a 2N solution 
of sulfuric acid in ethyl ether (110 ml) is added. After 30 minutes, the 
precipitate is filtered off to give the expected product (3.1 g). 
Yield: 76%. 
M.p.: 155.degree. C. 
EXAMPLE 15 
Herbicidal application in the pre-emergence treatment of plant species 
A number of seeds are sown in 9.times.9.times.9 cm pots filled with light 
agricultural soil, this number being determined as a function of the plant 
species and the size of the seed. 
The seeds are then covered with an approximately 3 mm thick layer of soil. 
After the soil has been moistened, the pots are treated by spraying with an 
amount of spraying mixture which corresponds to an application rate of 500 
liters/ha (hectare) and contains the active ingredient at the relevant 
concentration. 
The spraying mixture was prepared by diluting, with an equal volume of an 
aqueous solution containing 1 g/liter of Cemulsol NP10, a solution 
containing the desired concentration of the product to be tested in the 
following mixture: 
Soprophor FL: 15 g/liter 
Sapogenat TO 80: 3 g/liter 
Dimethylformamide q.s.: 1,000 ml 
Cemulsol NP10 is a non-ionic surface-active agent consisting of ethylene 
oxide/alkylphenol condensates, mainly of an ethylene oxide/nonylphenol 
condensate. Soprophor FL is an anionic surface-active agent consisting of 
phosphoric acid esters of condensates of ethylene oxide with alcohols or 
phenols. 
Sapogenat TO 80 is a non-ionic surface-active agent consisting of 
trialkylphenols. 
Depending on the concentration of active ingredient in the spraying 
mixture, the dose of active ingredient applied was 1 kg/ha to 8 kg/ha. 
The treated pots are then placed in troughs which are intended to receive 
moistening water, by subirrigation, and are kept for 28 days at ambient 
temperature under 70% relative humidity. 
After 28 days, the number of living plants in the pots treated with the 
spraying mixture containing the active ingredient to be tested, and the 
number of living plants in a control pot treated under the same 
conditions, but with a spraying mixture not containing active ingredient, 
are counted. The percentage destruction of the treated plants is thus 
determined relative to the untreated control. A percentage destruction 
equal to 100% indicates that there has been complete destruction of the 
plant species in question, and a percentage of 0% indicates that the 
number of living plants in the treated pot is identical to that in the 
control pot. 
The plant species used for the tests in this example were as follows: 
______________________________________ 
Abbreviation used 
______________________________________ 
Monocotyledon adventitious plants: 
Wild oat (Avena fatua) 
WO 
Panic grass (Echinochloa crus-galli) 
PA 
Italian rye-grass (Lolium multiflorum) 
RY 
Dicotyledon adventitious plants: 
Goosefoot (Chenopodium sp) 
GO 
Wild mustard (Sinapis arvensis) 
WM 
Dicotyledon crops: 
Bean (Phaseolus vulgaris) 
BE 
______________________________________ 
The results observed are indicated in Table I below. 
The comparison product is N-(phenyl)-carbamoyl-pyridine, unsubstituted on 
the phenyl, which is described as compound No. 25 in European Patent 
Application No. 0,044,262, and the chemical name of which is: 
3-N-(phenyl)-carbamoyl-5-ethoxycarbonyl-2,6-lutidine. 
EXAMPLE 16 
Herbicidal application in the post-emergence treatment of plant species 
A number of seeds are sown in 9.times.9.times.9 cm pots filled with light 
agricultural soil, this number being determined as a function of the plant 
species and the size of the seed. 
The seeds are then covered with an approximately 3 mm thick layer of soil 
and the seed is left to germinate until it produces a plantlet of 5 to 10 
cm in height. 
The pots are then treated by spraying with an amount of spraying mixture 
which corresponds to an application soil of 500 liters/ha and contains the 
active ingredient at the relevant concentration. 
The spraying mixture was prepared in the same manner as in Example 15. 
Depending on the concentration of active ingredient in the spraying 
mixture, the dose of active ingredient applied was 1 to 8 kg/ha. 
The treated pots are then placed in troughs which are intended to receive 
moistening water, by subirrigation, and are kept for 28 days at ambient 
temperature under 70% relative humidity. 
After 28 days, the number of living plants in the pots treated with the 
spraying mixture containing the active ingredient to be tested, and the 
number of living plants in a control pot treated under the same 
conditions, but with a spraying mixture not containing active ingredient, 
are counted. The percentage destruction of the treated plants is thus 
determined relative to the untreated control. A percentage destruction 
equal to 100% indicates that there has been complete destruction of the 
plant species in question, and a percentage of 0% indicates that the 
number of living plants in the treated pot is identical to that in the 
control pot. 
The names and abbreviations of the plant species used are as indicated 
above. 
The results observed are indicated in Table (II). 
EXAMPLE 17 
Selectivity with respect to crops, in the pre-emergence treatment of plant 
species 
The method described in Example 15 is followed, the plant species being 
replaced by the following crops: 
cotton (Gossipium barbadense) 
sunflower (Helianthus annuus) 
soya (Glycine max) 
and the treatment being carried out with a dose of 1 kg/ha. 
Under these conditions and with this dose, it was observed that: 
compounds Nos. 1, 8, 9 and 11 are well tolerated by cotton, and 
compounds Nos. 1, 3, 7, 8 and 11 are well tolerated by soya. 
The results described in these Examples 5 to 17 show the excellent 
herbicidal activity of the compounds according to the invention on the 
majority of the adventitious plants treated, both graminaceous or other 
mono-cotyledonous and dicotyledonous plants. 
For their use in practice, the compounds according to the invention are 
rarely employed by themselves. Most frequently, they form part of 
compositions. These compositions, which can be used as selective 
herbicides, contain, as the active ingredient, a compound according to the 
invention, as described above, in combination with agriculturally 
acceptable, solid or liquid carriers and with surface-active agents, also 
agriculturally acceptable. The customary inert carriers and the customary 
surface-active agents can be used in particular. 
These compositions can also contain numerous other ingredients such as e.g. 
protective colloids, adhesives, thickeners, thixotropic agents, 
penetrating agents, stabilizers, sequestering agents and the like, as well 
as other known active ingredients having pesticidal properties (in 
particular insecticides, fungicides or herbicides), properties for 
promoting plant growth (in particular fertilizers) or properties for 
regulating plant growth. More generally, the compounds according to the 
invention can be used in combination with any of the solid or liquid 
additives corresponding to the usual formulation techniques. 
The application rates and concentration of the compounds according to the 
invention can vary within wide limits, in particular according to the 
nature of the adventitious plants to be removed and the usual degree of 
infestation of the crops by these adventitious plants. 
In general, the compositions according to the invention usually contain 
from about 0.05 to 95% (by weight) of one or more compounds according to 
the invention, from about 1% to 94.5% of one or more solid or liquid 
carriers and, if appropriate, from about 0.1 to 20% of one or more 
surface-active agents. 
As has already been stated, the compounds according to the invention are 
generally used in combination with carriers and, if appropriate, 
surface-active agents. 
As used herein, the term "carrier" defines an organic or inorganic, natural 
or synthetic material with which the active ingredient is combined in 
order to facilitate its application to the plant, to seeds, to the soil or 
plant situs in general. Such carriers are therefore generally inert and 
must be agriculturally acceptable, in particular on the plant treated. The 
carrier can be solid (clays, natural or synthetic silicates, silica, 
resins, waxes, solid fertilizers or the like) or liquid (water, alcohols, 
ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, 
chlorohydrocarbons, liquefied gases or the like). 
The surface-active agent can be an emulsifying, dispersing or wetting agent 
of ionic or non-ionic type. Examples which may be mentioned are 
polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic or 
naphthalene-sulfonic acid salts, polycondensates of ethylene oxide with 
fatty alcohols, fatty acids or fatty amines, substituted phenols (in 
particular alkylphenols or arylphenols), salts of sulfosuccinic acid 
esters, taurine derivatives (in particular alkyltaurates) and phosphoric 
acid esters of condensates of ethylene oxide with alcohols or phenols. The 
presence of at least one surface-active agent is generally essential if 
the active ingredient and/or the inert carrier are not soluble in water 
and if the vehicle of application is water. 
For their application, the compounds of the formula (I) are, therefore 
generally in the form of compositions; such compositions according to the 
invention are formulated in a fairly wide variety of solid or liquid 
forms. 
Forms of solid compositions which may be mentioned are dusting powders or 
sprinkling powders (which can contain up to 100% of the compound of the 
formula (I)) and granules, in particular those obtained by extrusion, by 
compaction, by the impregnation of a granular carrier or by the formation 
of granules from a powder (the content of compound of the formula (I) in 
these granules being between 0.5 and 80%.) 
As forms of liquid compositions or compositions which are to be made up 
into liquid compositions for application, there may be mentioned 
solutions, in particular water-soluble concentrates and emulsifiable 
concentrates, emulsions, suspension concentrates (or flowables), wettable 
powders (or sprayable powders) and pastes. 
The emulsifiable concentrates contain the active ingredient dissolved in a 
solvent, which is usually an aromatic hydrocarbon, if appropriate using a 
co-solvent, which can be e.g. a ketone, an ester, an ether or the like. 
They usually contain from 10 to 60% by weight volume of active ingredient 
and from 2 to b 20% by weight/volume of emulsifying agent. If necessary, 
they can also contain various suitable additives such as surface-active 
agents, stabilizers, penetrating agents, corrosion inhibitors, colorants, 
adhesives and the like. 
The suspension concentrates (or flowables), which can be applied by 
spraying, are prepared so as to give a stable fluid product which does not 
form a deposit, and they usually contain from 10 to 75% of active 
ingredient, from 0.5 to 15% of surface-active agents, from 0.1 to 10% of 
thixotropic agents, from 0 to 10% of suitable additives such as anti-foam 
agents, corrosion inhibitors, stabilizers, penetrating agents and 
adhesives, and, as the carrier, water or an organic liquid in which the 
active ingredient is sparingly soluble or insoluble; certain organic 
solids, or inorganic salts, can be dissolved in the carrier in order to 
assist in preventing sedimentation or to act as anti-freeze agents for the 
water. 
The composition of a suspension concentrate is now given as an example: 
active ingredient: 250 g 
10:1 ethylene oxide/alkylphenol condensate (wetting agent): 10 g 
ethoxylated and salified polyaryl phosphate (dispersant): 10 g 
propylene glycol (anti-foam agent): 50 g 
polysaccharide (thickener): 2 g 
water q.s.: 1 liter 
The wettable (or sprayable powders) are usually prepared so as to contain 
20 to 95% of active ingredient, and they usually contain, in addition to 
the solid carrier, from 0 to 5% of a wetting agent, from 3 to 10% of a 
dispersing agent and, where necessary, from 0 to 10% of one or more 
stabilizers and/or other additives such as penetrating agents, adhesives, 
anti-caking agents, colorants and the like. 
Various compositions of wettable powders are now given as examples: 
active ingredient: 50% 
calcium lignosulfonate (deflocculant): 5% 
isopropylnaphthalenesulfonate (anionic) 
wetting agent): 1% 
anti-caking silica: 5% 
kaolin (filler): 39% 
Another example of a wettable powder, this time of 80% strength, is given 
below: 
active ingredient: 80% 
sodium alkylnaphthalenesulfonate: 2% 
sodium lignosulfonate: 2% 
anti-caking silica: 3% 
kaolin: 13% 
Another example of a wettable powder is given below: 
active ingredient: 50% 
sodium alkylnaphthalenesulfonate: 2% 
low-viscosity methylcellulose: 2% 
diatomaceous earth: 46% 
Another example of a wettable powder is given below: 
active ingredient: 90% 
sodium dioctyl-sulfosuccinate: 0.2% 
synthetic silica: 9.8% 
To obtain these sprayable powders or wettable powders, the active 
ingredients are intimately mixed with the additional substances in 
suitable mixers, and the mixture is ground in mills or other suitable 
grinders. This gives sprayable powders of advantageous wettability and 
suspendability; they can be suspended in water at any desired 
concentration and this suspension can be used very advantageously, in 
particular for application to the leaves of the plants. 
In place of the wettable powders, it is possible to produce pastes. The 
conditions and methods of preparation and use of these pastes are similar 
to those of the wettable powders or powders suitable for spraying. 
As already stated, the dispersions, e.g. the compositions obtained by 
diluting a wettable powder according to the invention with water, are 
included within the general scope of the present invention. The term 
"spraying mixture" is used to denote the compositions diluted in water, as 
they are applied to the crops. 
All these aqueous emulsions or dispersions, or spraying mixtures, can be 
applied by any suitable means to the crops in which weeds are to be 
destroyed, mainly by spraying, at doses which are generally of the order 
of 100 to 1,200 liters of spraying mixture per hectare. 
The granules, which are intended to be placed on the soil, are usually 
prepared so as to have dimensions of between 0.1 and 2 mm, and they can be 
manufactured by agglomeration or impregnation. Preferably, the granules 
contain 1 to 25% of active ingredient and 0 to 10% of additives such as 
stabilizers, slow release modifiers, binders and solvents. 
One example of the composition of granules uses the following constituents: 
active ingredient: 50 g 
cetyl polyglycol ether: 2.5 g 
polyethylene glycol: 35 g 
kaolin (particle size: 0.3 to 0.8 mm): 910 g 
In this particular case, the active ingredient is mixed with 
epichlorohydrin and the mixture is dispersed in acetone (60 g); the 
polyethylene glycol and the cetyl polyglycol ether are then added. The 
kaolin is wetted with the dispersion obtained and the acetone is then 
evaporated off in vacuo. 
As indicated above, the invention also relates to a process for destroying 
weeds in crops, in particular cotton, sunflower and soya crops, wherein an 
effective amount of at least one of the compounds according to the 
invention is applied to the plants and/or to the soil in the region in 
which weeds are to be destroyed. In practice, the compounds are used in 
the form of the herbicidal compositions according to the invention, which 
have been described above. In general, amounts of active ingredients 
ranging from 0.1 to 3 kg/ha give good results, it being understood that 
the choice of the amount of active ingredients to be used depends on the 
severity of the problem to be solved, the climatic conditions and the crop 
in question. The treatment is generally carried out as a pre-emergence 
treatment of the crops and adventitious plants, or as a pre-sowing 
treatment of the crops with incorporation into the soil (this 
incorporation is therefore an additional treatment method of the 
invention), although in certain cases, depending on the compound used, 
good results can also be obtained by post-emergence treatments as 
demonstrated in Example 16. Other methods of carrying out the treatment 
process according to the invention can also be used: thus, it is possible 
to apply the active ingredient to the soil, with or without incorporation, 
before planting the crop. 
The treatment process of the invention is equally applicable in the case of 
annual crops as in the case of perennial crops; in the latter case, it is 
preferred to apply the active ingredients of the invention in a localized 
manner, e.g. between the rows of the said crops. 
TABLE I 
______________________________________ 
Herbicidal activity in a greenhouse, in the 
pre-emergence treatment of plant species 
% destruction relative to the control 
Plant species 
Compound Dose 
No. kg/ha WO PA RY BE GO WM 
______________________________________ 
1 1 100 95 100 0 100 80 
8 100 100 100 30 100 100 
2 1 100 100 100 80 100 100 
8 100 100 100 100 100 100 
3 1 80 100 100 0 100 100 
8 100 100 100 0 100 100 
4 1 0 20 30 100 100 100 
8 20 80 80 100 100 100 
7 1 100 100 100 0 100 100 
8 100 100 100 100 100 100 
8 1 100 100 100 0 100 100 
8 100 100 100 100 100 100 
9 1 95 100 100 0 100 20 
8 100 100 100 100 100 100 
10 1 90 100 100 0 100 80 
8 100 100 100 0 100 100 
11 1 30 100 100 0 100 100 
6 100 100 100 40 100 100 
12 1 90 100 100 50 100 30 
Comparison 
2 0 0 0 0 30 0 
8 10 60 5 30 100 30 
______________________________________ 
Comparison = European Patent A0,044,262 Compound No. 25. 
TABLE II 
______________________________________ 
Herbicidal activity in a greenhouse, in the 
post-emergence treatment of plant species 
% destruction relative to the control 
Plant species 
Compound Dose 
No. kg/ha WO PA RY BE GO WM 
______________________________________ 
1 1 100 100 100 0 30 0 
8 100 100 100 100 20 70 
2 1 100 100 100 100 40 60 
8 100 100 100 100 100 100 
3 1 30 100 100 100 30 30 
8 100 100 100 100 100 
4 1 0 0 20 100 0 30 
8 20 50 30 100 20 100 
7 1 100 100 100 100 0 0 
8 100 100 100 100 60 100 
8 1 95 100 80 100 80 20 
8 100 100 100 100 100 100 
9 1 60 20 30 100 30 20 
8 100 100 100 100 100 100 
10 1 90 40 60 0 40 30 
8 100 100 100 100 100 95 
11 1 20 40 90 100 20 80 
6 100 100 100 100 50 100 
12 1 90 100 90 100 20 20 
Comparison 
8 0 20 0 0 30 20 
______________________________________ 
Comparison = European Patent A0,044,262 Compound No. 25.