Compounds of formula: ##STR1## in which: n=0, 1, 2 PA0 f=0, 1 PA0 Ar is an optionally substituted phenyl or pyridyl group PA0 U a chlorine or bromine atom PA0 V a bromine or chlorine or iodine atom PA0 B is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, which are optionally substituted by 1 to 6 halogen atoms, phenyl or pyridyl or oxidized pyridyl, which are optionally substituted. Use of these compounds as herbicides which are selective but especially antigraminaceous at preemergence.

The invention relates to new compounds, to their use as herbicides 
especially in the form of a herbicidal composition, and to a process for 
controlling weeds with the aid of these compounds or of these 
compositions. 
An objective of the present invention is therefore to propose compounds 
which can be used as herbicides in pre- or postemergence 
Another objective of the present invention is to propose compounds which 
can be used as antigraminaceous herbicides in pre- or postemergence. 
Another objective of the present invention is to propose compounds which 
can be used in pre- or postemergence as selective herbicides for corn and 
many dicotyledon crops (especially soya, rape, sunflower, cotton) and 
other monocotyledon crops (wheat, rice). 
GENERAL DEFINITION OF THE INVENTION 
Compounds of formula 
##STR2## 
in which: n=0, 1, 2 
f=0, 1. Ar is chosen from the groups 
##STR3## 
U being a bromine or chlorine atom, V being a bromine, chlorine or iodine 
atom, 
R.sub.1 being a halogen atom (especially Cl or Br or F), a C.sub.1 -C.sub.4 
alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 
-C.sub.4 haloalkoxy, nitro or cyano group, C.sub.6 -C.sub.10 aryl 
(especially phenyl or naphthyl), C.sub.7 -C.sub.11 aralkyl (especially 
benzyl), C.sub.6 -C.sub.10 aryloxy (especially phenoxy or naphlhoxy) 
optionally substituted by 1 or 2 halogen atoms or C.sub.7 -C.sub.11 
aralkyloxy (especially benzyloxy) optionally substituted by 1 or 2 halogen 
atoms, 
m=0, 1, 2, 3, 4, 5, p =0, 1, 2, 3, 4, the various radicals R.sub.1 being 
identical or different when m or p is greater than or equal to 2, 
B is chosen from C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.10 cycloalkyl 
groups, these groups being optionally substituted by 1 to 6 halogen atoms 
or chosen from the groups 
##STR4## 
R.sub.3 having one of the meanings shown for R.sub.1 or NR.sub.4 R.sub.5, 
S(O).sub.h R.sub.6, (C.dbd.O)R.sub.7, 
R.sub.4 and R.sub.5, which are identical or different, are H, C.sub.1 
-C.sub.4 alkyl or C.sub.6 -C.sub.10 aryl, R.sub.6 is C.sub.1 -C.sub.4 
alkyl, 
R.sub.7 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 
-C.sub.4 haloalkoxy or 
NR.sub.9 R.sub.10, R.sub.9 and R.sub.10 which are identical or different, 
are 
H or C.sub.1 -C.sub.4 alkyl, 
the varius radicals R.sub.3 being identical or different when 
k or g is greater than or equal to 2, 
k=0, 1, 2, 3, 4, 5, g=0, 1, 2, 3, 4, 
h=0, 1, 2, 
n=0, 1. 
The aliphatic groups may be linear or branched. 
PREFERRED ALTERNATIVE FORMS 
Depending on the preferred embodiments, the following alternative forms 
will be chosen, taken in combination or otherwise: n=2, U and V=Br, m 
smaller than or equal to 3, p smaller than or equal to 2, k smaller than 
or equal to 2, g smaller than or equal to 1, R.sub.1 is halogen, nitro, 
trifluoromethyl, methoxy or methyl. 
The compounds of formula (I) and the compounds which may be employed as 
intermediates in the processes of preparation, and which will be defined 
when these processes are described, can exist in one or more isomeric 
forms, depending on the number of asymmetric centres in the molecule. The 
invention consequently relates both to all the optical isomers and to 
their racemic mixtures and the corresponding diastereoisomers. The 
separation of the diastereoisomers and/or of the optical isomers can be 
carried out according to methods which are known per se. 
PROCESSES FOR THE PREATION OF THE COMPOUND OF FORMULA (I) 
The compounds of formula (I) in which n=0, 1, 2, the other substituents 
having the same definition as that shown in the general definition of the 
invention, may be prepared by bringing a compound of formula: 
##STR5## 
in which Ar, n, f and B have the same meaning as in the general definition 
of the invention, into contact with halides UV like chlorine (U=Cl, V=Cl), 
bromine (U=Br, V=Br), chlorine iodide (U=Cl, V=I), bromine iodide (U=Br, 
V=I) or chlorine bromide (U=Cl, V=Br), in an aprotic inert solvent such as 
chloroform, carbon tetrachloride, tetrahydrofuran, dimethoxyethane or 
acetonitrile, in the presence or otherwise of an acid such as acetic acid 
or hydrochloric acid at a temperature of -78.degree. C. to 60.degree. C. 
(preferably 0.degree. C. to 20.degree. C.) and in a molar ratio IA:UV of 
between 1 and 5 (preferably 1 and 2). This reaction is known especially 
from J. March, "Advanced Organic Chemistry", publ. McGraw-Hill (1985), p. 
724-726, S. Akiyoshi and K. Okuno, J. Amer. Chem Soc. (1952), 74, 5759 and 
F. G. Weber, Tetrahedron (1969), 25, 4283. 
These same compounds of formula (I) in which n=0, 1 or 2, the other 
substituents having the same definition as that shown in the general 
definition of the invention, can also be prepared by the action on a 
compound of formula (IA) where the substituents have the same meaning as 
in the general definition of the invention, of a halogenating agent ZV, V 
being the chlorine or bromine atom and Z an acetamido radical, such as 
N-haloacetamide or N-halosuccinimide in the presence of a donor of a 
halide anion U, U being the chlorine or bromine atom, such as the hydrogen 
halide acids HU, ammonium halides (R).sub.4 NU, R being an alkyl radical, 
or the salts MU, M being an atom of an alkali or alkaline-earth metal or a 
silver atom in an inert solvent such as methylene chloride, chloroform, 
acetonitrile, dimethoxyethane or acetic acid at a temperature of 
-78.degree. C. to 60.degree. C. (preferably 0.degree. C. to 20.degree. C.) 
and in a molar ratio IA:ZV:U of between 1:1:1 and 1:5:100 (preferably 
1:2:5). 
This reaction is known especially from J. March, ibid. p. 725, R. E. 
Buckles and J. W. Long, J. Amer. Chem. Soc (1959), 81, 2191, A. Marquet 
and J. Jacques, Tetrahedron Letters (1959), 9, 24 and C. H. Robinson et 
al., J. Amer. Chem. Soc. (1959), 81, 2191. 
The compounds of formula (I) in which n=0 or 1, the other substituents 
having the same definition as that shown in the general definition of the 
invention, can be oxidized to a sulphoxide (n=1) by one equivalent of 
oxidizing agent at a temperature of -70.degree. C. to 5.degree. C. 
(generally 0.degree. C.) or can be oxidized to a sulphone (n=2) by two or 
more equivalents of oxidizing agent at a tempera ture of 0.degree. C. to 
60.degree. C. (generally 10.degree. C. to 30.degree. C.) by many oxidizing 
agents, such as KMnO.sub.4, H.sub.2 O.sub.2, CH.sub.3 CO.sub.3 H, 
perbenzoic acids, KHSO.sub.5, and others, by following very many known 
methods, J. March, ibid. p. 1089-1090 and B. M. Trost and R. Braslau, J. 
Org. Chem. (1988), 53, 532. 
PROCESS FOR THE PREATION OF THE COMPOUND OF FORMULA IA 
Method A 
The compounds of formula (IA) in which n=2, the other substituents having 
the same definition as that shown in the general definition of the 
invention, can be obtained by bringing a compound of formula 
##STR6## 
in which Ar, R.sub.1 and m or p have the same meaning as in the general 
definition of the invention, and T is a chlorine or bromine atom, into 
contact with a compound of formula: 
EQU MSO.sub.2 (CH.sub.2).sub.f -B (III) 
f and B having the same definition as that shown in the definition of the 
invention, 
M being an atom of an alkali or alkaline-earth metal (expecially Li, K, 
Na). 
The reaction is generally performed in a dipolar aprotic solvent, 
especially dimethylformamide or N-methylpyrrolidone, or in water in a 
mixture in the proportions of 5/95 to 90/10 (preferably 10/90 to 50/50) 
with a water-soluble solvent such as alcohols, acetone, acetonitrile or 
dimethoxy-ethane, in the presence or otherwise of a catalytic or other 
quantity of alkali metal iodide, in the presence or absence of a catalytic 
quantity of a phase transfer agent such as tetrabutylammonium halides, at 
a temperature of between 25.degree. C. and 150.degree. C. (preferably 
60.degree. C. to 120.degree. C.) and in a molar ratio II:III of between 1 
and 10 (preferably 1 and 2). 
This reaction is known especially from J. March, ibid. p. 363. The 
compounds of formula (II) where T is chlorine and Ar is 1-Ar (phenyl 
nucleus) are prepared by chlorination of a 2-phenyl-1-propene compound of 
formula: 
##STR7## 
in which Ar is 1-Ar (phenyl nucleus), R.sub.1 and m having the same 
meaning as in the definition of the general fcrmula, by means of the 
reactant Ca(OCl).sub.2 /CO.sub.2. This reaction is described by S. G. 
Hegde and J. Wolinsky, Tetrahedron Letters (1981), 22, 5019. 
These same compounds of formula (II) where T is chlorine and Ar is 1-Ar 
(phenyl nucleus) can be prepared by chlorination of the compounds of 
formula (IV) by means of the SO.sub.2 Cl.sub.2 /Na.sub.2 CO.sub.3 reactant 
according to M. Bulliard et al., Tetrahedron Letters (1989), 30, 5767. 
The compounds of formula (II) where T is chlorine, Ar having the same 
definition as that shown in the general definition of the invention, can 
also be prepared by chlorination of the abovementioned compounds of 
formula (IV) using N-chlorosuccinimide in the presence of bisaryl 
diselenide according to the process of K. B. Sharpless and T. Hori, J. 
Org. Chem. (1979), 44, 4204. 
The compounds of formula (II) where T is chlorine or bromine, Ar having the 
same definition as that shown in the general definition of the invention, 
can also be prepared by thermal or photochemical radical halogenation of 
the compound of formula (IV) using N-halosuccinimide in an aprotic solvent 
such as carbon tetrachloride or in the absence of solvent, with or without 
a free-radical initiator, at a temperature of 20.degree. C. to 170.degree. 
C. (preferably 80.degree. C. to 100.degree. C.), according to S. F. Reed, 
J. Org. Chem. (1965), 30, 3258. They can also be prepared by halogenation 
of the compounds of formula (II) where T is OH, Ar having the same 
definition as that shown in the general definition of the invention, with 
a halogenating agent such as SOCl.sub.2, POCl.sub.3, PBr.sub.3, J. March, 
ibid. p. 382-384, or with the LiCl/CH.sub.3 SO.sub.2 Cl/collidine reactant 
according to E. W. Collington and A. I. Meyers, J. Org. Chem. (1971), 36, 
3044. 
The compounds of formula (II) where T is OH, Ar having the same definition 
as that shown in the general definition of the invention, can be prepared 
by allylic oxidation of the compound of formula (IV) using selenium oxide, 
catalytic or otherwise, in the presence of an oxidizing agent such as 
tert-butyl hydroperoxide, in an inert solvent such as halogenated solvents 
(preferably methylene chloride) or tert-butanol, in the presence of 
inorganic or organic acid, according to M. A. Umbreit and K. B. Sharpless, 
J. Amer. Chem. Soc. (1977), 99, 5526. 
The compounds of formula (IV) can be obtained by dehydration of a 
2-aryl-2-propanol compound of formula: 
##STR8## 
in which Ar, R.sub.1 and m or p have the same meaning as in the general 
definition of the invention, using dehydrating agents such as P.sub.2 
O.sub.5, KHSO.sub.4, POCl.sub.3 /pyridine and others, according to J. 
March, ibid. p. 901-903. 
The compounds of formula (V) can be prepared by bringing acetophenone or 
acetylpyridine or an acid derivative of formula: 
##STR9## 
in which Ar, R.sub.1 and m or p have the same meaning as in the general 
definition of the invention and W is methyl, alkoxy (corresponding benzoic 
ester) or chlorine, into contact with one or two equivalents of 
methylmagnesium halide according to J. March, ibid. p. 816-822. 
The compounds of formula (VI) are obtained in a manner which is known per 
se. The compounds of formula (III) can be prepared by reduction of the 
corresponding sulphonyl halides (generally a chloride) with zinc, with 
sodium or potassium iodide and with sodium sulphite, accordinq to J. 
March, ibid. p. 445-446 and W. E. Truce and A. H. Murphy, Chem Rev. 
(1951), 48, 69. The sulphonyl halides can be prepared according to J. 
March, ibid. p. 1172. 
The compounds of formula (III) can also be prepared by reaction of an 
organometallic (usually lithium) compound of formula: 
EQU M(CH.sub.2).sub.f -B (IIIA) 
f and B having the same meaning as that shown in the definition of the 
invention, M being especially lithium, with sulphur dioxide SO.sub.2, at a 
temperature of between -78.degree. C. and 20.degree. C. (preferably 
-78.degree. C. to -40.degree. C.) in the absence or in the presence of an 
aprotic solvent such as ethyl ether or tetrahydrofuran, according to H. W. 
Pinnick and M. A. Reynolds, J. Org. Chem. (1979), 44, 160 and J. March, 
ibid. p. 550. 
The compounds of formula (IIIA) are obtained in a manner which is known per 
se. 
Method B 
The compounds of formula (IA) in which n=0, 1 or 2 can be prepared by 
reaction of the alkali metal salt of an aryl or alkyl thiolate of formula: 
EQU M'S(CH.sub.2).sub.f -B (VII) 
in which M' is an alkali metal or alkaline-earth metal atom, especially 
sodium or potassium, f and B having the same definition as that shown in 
the definition of the invention, with a compound of formula (II) where T 
is halogen, described above, in a protic or aprotic inert solvent such as 
ketones, alcohols, tetrahydrofuran, acetonitrile or aprotic dipolar 
solvents such as dimethylformamide, at a temperature of 0.degree. C. to 
80.degree. C., (generally 25.degree. C. to 60.degree. C.) in a molar ratio 
II:VII which is generally between 1 and 10 (preferably 1 and 2). 
The sulphide thus obtained (n=0) can be oxidized to sulphoxide (n=1) using 
one equivalent of oxidizing agent at a temperature of -70.degree. C. to 
5.degree. C. (generally 0.degree. C.) or can be oxidized to sulphone (n=2) 
using two or more equivalents of oxidizing agent at a temperature of 
0.degree. C. to 60.degree. C. (generally 10.degree. C. to 30.degree. C.) 
using numerous oxidizing agents such as KMnO.sub.4, H.sub.2 O.sub.2, 
CH.sub.3 CO.sub.3 H, perbenzoic acids, KHSO.sub.5, and others, using very 
numerous known methods: J. March, ibid. p. 1089-1090 and B. M. Trost and 
R. Braslau, J. Org. Chem (1988), 53, 532. 
Another subject of the invention is the new products (II) to (VII) which 
can be used for making use of the process just described.

The following examples illustrate the invention. 
EXAMPLE 1 
2-Phenyl-1-phenylsulphonyl-2-propene (10.3 g, 0.04 moles) is dissolved in 
chloroform (100 cc). Bromine (6.8 g, 0.042 moles) is then added dropwise 
until the colour persists. The organic phase is washed with a 5% solution 
of sodium thiosulphate (50 cc), water (50 cc) and is dried over 
MgSO.sub.4. After evaporation, a colourless oil (18.8 g) is obtained. This 
oil is dissolved in a mixture of chloroform (20 cc) and ether (40 cc) and 
is stored overnight at -18.degree. C. White crystals of 
1,2-dibromo-2-phenyl-3-phenylsulphonylpropane (14.3 g, 86%) are filtered 
off. Mp=74.degree. C. 
EXAMPLE 2 
2-Phenyl-1-phenylsulphonyl-2-propene (2.6 g, 0.01 mole) is dissolved in 
chloroform (20 cc). The solution is cooled to 5.degree. C. and chlorine 
iodide (1.8 g, 0.011 moles) in solution in chloroform (5 cc) is added 
dropwise. The mixture is stirred at 5.degree. C. for two hours and is then 
treated in the same way as in Example 1. Evaporation leaves a yellow oil 
(5.3 g). This oil is dissolved in ether (7.5 cc) and is stored overnight 
at -18.degree. C. Off-white crystals of 
2-chloro-1-iodo-2-phenyl-3-phenylsulphonylpropane (3.3 g, 78%) are 
filtered off. Mp=75.5.degree. C. (dec.). 
EXAMPLE 3 
2-Phenyl-1-phenylsulphonyl-2-propene (2.6 g, 0.01 mole) is suspended in a 
mixture of acetic acid (50 cc) and 35% hydrochloric acid (10 cc). Chlorine 
is then introduced into the reaction mixture until the allyl sulphone has 
completely dissolved (5 min). The mixture is poured into ice and water 
(250 g) and is stirred vigorously until a resin forms. 
The resin is filtered off and dissolved in methylene chloride (100 cc) and 
the organic phase is washed with a 10% sodium carbonate solution (100 cc), 
water (2.times.100 cc) and is dried over MgSO.sub.4. Evaporation leaves a 
yellow oil (4.8 g). This oil is dissolved in ether (20 cc) and is stored 
overnight at -18.degree. C. After filtration and recrystallization from 
ethanol, pale yellow crystals of 
1,2-dichloro-2-phenyl-3-phenylsulphonylpropane (1.2 g, 36%) are obtained. 
Mp=95.degree. C. 
EXAMPLE 4 
2-Phenyl-1-phenylsulphonyl-2-propene (2.6 g, 0.01 mole) is suspended in 
acetic acid (50 cc). Lithium chloride (2 g, 0.05 moles) and 35% 
hydrochloric acid (5 cc) are then added and, finally, N-bromosuccinimide 
(1.8 g, 0.01 mole). The mixture is stirred until dissolved (15 min) and is 
then treated in the same way as in Example 3. Evaporation leaves a yellow 
oil (3.6 g) which is redissolved in ether (10 cc) and stored overnight at 
-18.degree. C. White crystals of 
1-bromo-2-chloro-2-phenyl-3-phenylsulphonylpropane (1.5 g, 40%) are 
filtered off. Mp=91.degree. C. 
EXAMPLE 5 
Using the same method as in Example 1, 
2-(6-chloro-2-pyridyl)-1-phenylsulphonyl-2-propene (1.0 g, 0.0035 moles) 
is treated with bromine (0.6 g, 0.0038 moles) in chloroform. After 
treatment, evaporation leaves an oil (1.6 g) which is crystallized from 
ether (40 cc) overnight at -18.degree. C. White crystals of 
1,2-dibromo-2-(6-chloro-2-pyridyl)-3-phenylsulphonylpropane (1.2 g, 75%) 
are filtered off. Mp=119.degree. C. 
EXAMPLE 6 
Using the same method as in Example 1, 
2-(6-chloro-2-pyridyl)-1-cyclopropylsulphonyl-2-propene (1.4 g, 0.0054 
moles) is treated with bromine (0.87 g, 0.0054 moles) in chloroform. After 
treatment, evaporation leaves an oil (2.1 g), which is chromatographed on 
silica (eluent: 80/20 heptane/chloroform) to give crystals of 
1,2-dibromo-2-(6-chloro-2-pyridyl)-3-cyclopropylsulphonylpropane (0.7 g, 
31%). Mp=75.degree. C. The compounds brought together in the table below 
were prepared according to the method of Example 1. 
______________________________________ 
##STR10## 
Mp (solvent) 
Example 
R1 f B n.sub.D (temperature) 
______________________________________ 
7 2-F 0 phenyl 123.degree. C. 
(CHCl.sub.3 /pentane) 
8 4-Me 0 phenyl 101.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
9 4-F 0 phenyl 103.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
10 3,5-diCl 0 phenyl 135.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
11 H 1 phenyl 93.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
12 H 0 4-F phenyl 103.degree. C. 
(CHCl.sub.3 /pentane) 
13 H 0 2-Cl phenyl 
120.degree. C. 
(CHCl.sub.3 /pentane) 
14 H 0 2-F phenyl 82.degree. C. (Et.sub.2 O) 
15 H 0 2-Me phenyl 
74.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
16 H 0 3-Me phenyl 
95.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
17 H 0 2-Cl 4-F phenyl 
110.degree. C. 
(Et.sub.2 O/pentane) 
18 3-Cl 0 2-Cl phenyl 
87.degree. C. 
(CH.sub.2 Cl.sub.2 /iPr.sub.2 O) 
19 3-F 0 2-Cl phenyl 
97.degree. C. 
(Et.sub.2 O/pentane) 
20 3-CF.sub.3 
0 2-Me phenyl 
92.degree. C. (Et.sub.2 O) 
21 3,5-diCl 0 4-F phenyl 133.5.degree. C. 
(CHCl.sub.3 /Et.sub.2 O) 
22 3,5-diCl 0 2-Me phenyl 
117.degree. C. 
(chromatography) 
23 H 0 (CH.sub.2).sub.3 CH.sub.3 
1.5768 (25.degree. C.) 
24 H 0 cyclopropyl 
95.degree. C. (Et.sub.2 O) 
25 3-Cl 0 CH(CH.sub.3).sub.2 
1.5717 (24.degree. C.) 
______________________________________ 
Preparation of 2-phenyl-1-phenylsulphonyl-2-propene 
2-Phenyl-1-propene (130 cc, 1 mole) is dissolved in methylene chloride 
(1,500 cc). Water (300 cc) and calcium hypochlorite (101.5 g, 0.5 moles) 
containing 70% of active chlorine are added. Solid carbon dioxide is added 
for 2 hours with very energetic stirring. The two phases are separated and 
the organic phase is dried over MgSO.sub.4. 
After evaporation, a yellow oil (145 g) is obtained. NMR analysis (60 MHz) 
shows the presence of 45% of 1-chloro-2-phenyl-2-propene, 45% of 
1-chloro-2-phenyl-1-propene and 10% of 1-chloro-2-phenyl-2-propanol. 
This mixture (17 g, 0.05 moles as 1-chloro-2-phenyl-2-propene) is dissolved 
in dimethylformamide (100 cc). Sodium benzenesulphinate (8.2 g, 0.05 
moles) is added and the mixture is heated to 70.degree. C. for 2 h. The 
reaction mixture is poured into ice and water (350 g). It is stirred 
vigorously with pentane (150 cc) to extract the unreacted 
1-chloro-2-phenyl-1-propene and 1-chloro-2-phenyl-2-propanol for 15 to 30 
min until crystallization is complete. The crystals formed are filtered 
off, are washed with pentane (50 cc) and diisopropyl ether (50 cc), are 
drained thoroughly and are dried. 2-Phenyl-1-phenylsulphonyl-2-propene 
(9.8 g, 76%) is obtained. Mp=105.degree. C. 
The following compounds were prepared in the same way: 
2-(2-fluorophenyl)-1-phenylsulphonyl-2-propene, mp=95.degree. C., 
2-(4-methylphenyl)-1-phenylsulphonyl-2-propene, mp=92.degree. C., 
2-(4-fluorophenyl)-1-phenylsulphonyl-2-propene, mp=85.degree. C., 
2-(3-chlorophenyl)-1-(2-chlorophenylsulphonyl)-2-propene, mp=87.degree. C., 
1-(2-chlorophenylsulphonyl)-2-phenyl-2-propene, n.sup.22 =1.6090, 
2-(3,5-dichlorophenyl)-1-phenylsulphonyl-2-propene, mp=98.degree. C., 
1-(2-chlorophenylsulphonyl)-2-(3-fluorophenyl)-2-propene, n.sub.D.sup.24 
=1.5860, 
1-(2-fluorophenylsulphonyl)-2-phenyl-2-propene, mp=84.degree. C., 
1-butylsulphonyl-2-phenyl-2-propene, mp=25.degree. C., 
1-cyclopropylsulphonyl-2-phenyl-2-propene, mp=76.degree. C. 
Preparation of 1-benzylsulphonyl-2-phenyl-2-propene 
Potassium carbonate (27 g, 0.19 moles) is suspended in acetone (600 cc). 
The mixture is heated to 60.degree. C. and is degassed with nitrogen. A 
mixture of benzyl mercaptan (21.7 g, 0.17 moles) and the allyl chloride 
(59 g, 0.17 moles as 1-chloro-2-phenyl-2-propene) prepared according to 
the preceding example, in solution in acetone (175 cc) is added dropwise 
at 60.degree. C. The mixture is stirred at 60.degree. C. for two hours. 
The reaction mixture is poured into ice and water (2,000 g) and is 
reextracted with ether (3.times.500 cc). The organic phase is washed with 
water until neutral and is dried over MgSO.sub.4. Evaporation leaves a 
yellow oil (82.5 g), which is chromatographed on silica (eluent heptane, 
then 99/1 heptane/chloroform) to give 1-benzylthio-2-phenyl-2-propene 
(19.5 g, 46%). Colourless oil. n.sub.D.sup.25 =1.6041. 
1-Benzylthio-2-phenyl-2-propene (13.2 g, 0.055 moles) is dissolved in 
methanol (300 cc) and water (300 cc). Oxone (36.9 g, 0.12 moles as 
HKSO.sub.5) is added portionwise and the mixture is stirred at ambient 
temperature for three hours. The reaction mixture is diluted with water 
(1,000 cc), pentane (100 cc) is added, and the mixture is stirred 
vigorously until crystallization takes place. White crystals of 
1-benzylsulphonyl-2-phenyl-2-propene (10.7 g, 72%) are obtained by 
filtration followed by drying. Mp=118.degree. C. 
The following compounds were prepared in the same way: 
2-(3-chlorophenyl)-1-isopropylsulphonyl-2-propene, n.sub.D.sup.25 =1.5715, 
1-(4-fluorophenylsulphonyl)-2-phenyl-2-propene, mp=83.degree. C., 
1-(3-methylphenylsulphonyl)-2-phenyl-2-propene, mp=61.degree. C. 
1-(2-methylphenylsulphonyl)-2-phenyl-2-propene, mp=62.degree. C., 
1-(2-chloro-4-fluorophenylsulphonyl)-2-phenyl-2-propene, mp=64.degree. C., 
2-(3,5-dichlorophenyl)-1-(4-fluorophenylsulphonyl)-2-propene, 
mp=105.degree. C., 
2-(3,5-dichlorophenyl)-1-(2-methylphenylsulphonyl)-2-propene, mp=72.degree. 
C., 1-(2-methylphenylsulphonyl)-2-(3-trifluoromethylphenyl)-2-propene, 
mp=51.degree. C. 
Preparation of 2-(6-chloro-2-pyridyl)-1-phenyl-sulphonyl-2-propene 
2-(6-Chloro-2-pyridyl)-1-propene (15.3 g, 0.1 mole) is dissolved in 
1,2-dichloroethane (200 cc). Bis(4-chlorophenyl) diselenide (0.5 g, 
catalytic) and N-chlorosuccinimide (14.7 g, 0.11 moles) are added and 
heated to 60.degree. C. for 24 hours. The reaction mixture is concentrated 
down to one third, the succinimide is filtered off and the organic phase 
is washed with water (2.times.200 cc), with a 15% solution of sodium 
bicarbonate (1.times.200 cc) and water (2.times.200 cc) and is dried over 
MgSO.sub.4. Crude: 13.9 g. 
NMR analysis (60 MHz) shows the presence of 55% of 
1-chloro-2-(6-chloro-2-pyridyl)-2-propene and 45% of 
1-chloro-2-(6-chloro-2-pyridyl)-1-propene. 
In a similar manner to the preparation of 
2-phenyl-1-phenylsulphonyl-2-propene, this mixture (7 g, 0.02 moles as 
1-chloro-2-(6-chloro-2-pyridyl)-2-propene) is treated with sodium 
benzenesulphinate to obtain, after treatment, 
2-(6-chloro-2-pyridyl)-1-phenylsulphonyl-2-propene (4.3 g, 73%). 
Mp=135.degree. C. 
The following compound was prepared in the same way: 
2-(6-chloro-2-pyridyl)-1-cyclopropylsulphonyl-2-propene, n.sub.D.sup.24 
=1.5730. 
The invention also relates to the use of the compounds of formula (I) as a 
herbicide. As weeds which can be controlled or destroyed using the 
compounds of formula (I) there may be mentioned: 
______________________________________ 
Graminaceae/Cyperaceae 
Abbreviation 
Latin name English name 
______________________________________ 
AVE Avena fatua Wild oat 
ECH Echinochloa crusgalli 
Panic grass 
LOL Lolium multiflorum 
Italian ryegrass 
CYP Cyperus esculentus 
Chufa flat sedge 
DIG Digitaria sanguinalis 
Hairy fingergrass 
ALO Alopercurus myosuroides 
Slender foxtail 
______________________________________ 
Most of the time, the compounds of formula (I) are employed in the form of 
a herbicidal composition comprising one or more agriculturally acceptable 
carriers. 
In fact, for their practical use, the compounds according to the invention 
are rarely employed by themselves. In most cases these compounds form part 
of compositions. These compositions, which can be employed as herbicidal 
agents, contain as active substance a compound according to the invention 
such as described above mixed with agriculturally acceptable solid or 
liquid carriers and surface-active agents which are also agriculturally 
acceptable. In particular, the usual inert carriers and the usual 
surface-active agents can be employed. These compositions also form part 
of the invention. 
These compositions may also contain all kinds of other ingredients such as, 
for example, protective colloids, adhesives, thickeners, thixotropic 
agents, penetrating agents, stabilizers, sequestrants and the like. More 
generally, the compounds employed in the invention may be used in 
combination with any of the solid or liquid additives corresponding to the 
usual formulation techniques. 
As a general rule, the compositions according to the invention usually 
contain approximately from 0.05 to 95% (by weight) of a compound according 
to the invention, one or more solid or liquid carriers and, optionally, 
one or more surface-active agents. 
In the present description the term "carrier" denotes a natural or 
synthetic, organic or inorganic substance with which the compound is 
combined to facilitate its application to the plant, to seed or to the 
soil. This carrier is therefore generally inert and it must be 
agriculturally acceptable, especially on the treated plant. The carrier 
may be solid (clays, natural or synthetic silicates, silica, resins, 
waxes, solid fertilizers, and the like) or liquid (water, alcohols, 
especially butanol, and the like). 
The surface-active agent may be an emulsifying, dispersing or wetting agent 
of an ionic or nonionic type or a mixture of such surface-active agents. 
There may be mentioned, for example, salts of polyacrylic acids, salts of 
lignosulphonic acids, salts of phenolsulphonic or naphthalenesulphonic 
acids, polycondensates of ethylene oxide with fatty alcohols or with fatty 
acids or with fatty amines, substituted phenols (especially alkylphenols 
or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives 
(especially alkyl taurates), phosphoric esters of polycondensates of 
ethylene oxide with alcohols or phenols, esters of fatty acids and of 
polyols, and sulphate, sulphonate and phosphate functional derivatives of 
the above compounds. 
The presence of at least one surface-active agent is generally 
indispensible when the compound and/or the inert carrier are not 
water-soluble and the vector agent of the application is water. 
Thus, therefore, the compositions for agricultural use according to the 
invention may contain the active substances according to the invention 
within very wide limits, ranging from 5.times.10.sup.-5 % to 95% (by 
weight). Their content of surface-active agent is advantageously between 
5% and 40% by weight. 
These compositions according to the invention are themselves in fairly 
diverse solid or liquid forms. 
As solid forms of compositions, there may be mentioned dusting powders 
(with a compound content which can go up to 100%) and granulates, 
especially those obtained by extrusion, by compacting, by impregnation of 
a granulated carrier or by granulation starting with a powder (the content 
of compound in these granulates being between 0.5 and 80% in these latter 
cases). 
The wettable powders (or spraying powder) are usually prepared so that they 
contain 20 to 95% of active substance, and they usually contain, in 
addition to the solid carrier, from 0 to 30% of a wetting agent, from 3 to 
20% of a dispersing agent and, when necessary, from 0 to 10% of one or 
more stabilizers and/or other additives, such as penetrating agents, 
adhesives or anticaking agents, colorants, and the like. 
To obtain the spraying powders or wettable powders, the active substances 
are mixed intimately with the additional substances in suitable mixers and 
are ground up using mills or other suitable grinders. This yields spraying 
powders whose wettability and suspendability are advantageous; they can be 
made into a suspension with water at any desired concentration, and these 
suspensions can be employed very advantageously, in particular for 
application to plant foliage. 
Pastes can be produced instead of the wettable powders. The conditions and 
methods of production and of use cf these pastes are similar to those of 
the wettable powders or spraying powders. 
By way of example, here are various compositions of wettable powders (or 
spraying powders): 
EXAMPLE F 1 
______________________________________ 
active substance (compound No. 1) 
50% 
fatty alcohol/ethylene oxide condensate 
2.5% 
(wetting agent) 
phenylethylphenol/ethylene oxide condensate 
5% 
(dispersing agent) 
chalk (inert carrier) 42.5% 
______________________________________ 
EXAMPLE F 2 
______________________________________ 
active substance (compound No. 1) 
10% 
syntheic oxo C.sub.13 alcohol of branched 
0.75% 
type, condensed with 8 to 10 ethylene 
oxides (wetting agent) 
neutral calcium lignosulphonate 
12% 
(dispersing agent) 
calcium carbonate (inert filler) 
q.s. 100% 
______________________________________ 
EXAMPLE F 3 
This wettable powder contains the same ingredients as in the preceding 
example, in the following proportions: 
______________________________________ 
active substance 75% 
wetting agent 1.50% 
dispersing agent 8% 
calcium carbonate (inert filler) 
q.s. 100% 
______________________________________ 
EXAMPLE F 4 
______________________________________ 
active substance (compound No. 1) 
90% 
fatty alcohol/ethylene oxide condensate 
4% 
(wetting agent) 
phenylethylphenol/ethylene oxide condensate 
6% 
(dispersing agent) 
______________________________________ 
EXAMPLE F 5 
______________________________________ 
active substance (compound No. 1) 
50% 
mixture of anionic and nonionic 
2.5% 
surfactants (wetting agent) 
sodium lignosulphonate (dispersing agent) 
5% 
kaolin clay (inert carrier) 
42.5% 
______________________________________ 
The compounds according to the invention can be formulated in the form of 
water-dispersible granulates which are also included within the scope of 
the invention. 
These dispersible granulates, with an apparent density which is generally 
between approximately 0.3 and 0.6, have a particle size which is generally 
between approximately 150 and 2,000 and preferably between 300 and 1,500 
microns. 
The content of active substance in these granulates is generally between 
approximately 1% and 90%, and preferably between 25% and 90%. 
The remainder of the granulate is essentially made up of a solid filler and 
optionally of surface-active adjuvants endowing the granulate with 
properties of dispersibility in water. These granulates can be essentially 
of two distinct types, depending on whether the filler contained is or is 
not water-soluble. When the filler is water-soluble, it may be inorganic 
or, preferably, organic. Excellent results have been obtained with urea. 
In the case of an insouble filler, the latter is preferably inorganic, 
such as, for example, kaolin or bentonite. It is then advantageously 
accompanied by surface-active agents (in a proportion of 2 to 20% by 
weight of the granulate) more than half of which consists, for example, of 
at least one essentially anionic dispersing agent such as an alkali metal 
or alkaline-earth metal polynaphthalenesulphonate or an alkali metal or 
alkaline-earth metal lignosulphonate, the remainder consisting of nonionic 
or anionic wetting agents, such as an alkali metal or alkaline-earth metal 
alkylnaphthalenesulphonate. 
Furthermore other adjuvants, such as antifoaming agents, may be added, 
although this is not essential. 
The granulate according to the invention may be prepared by mixing the 
necessary ingredients, followed by granulation according to a number of 
techniques which are known per se (pelletizer, fluid bed, sprayer, 
extrusion, and the like). The finishing step is generally crushing 
followed by screening to the chosen particle size within the limits noted 
above. 
It is preferably obtained by extrusion, the operation being carried out as 
indicated in the examples below. 
EXAMPLE F 6 
Dispersible Granulates 
90% by weight of active substance (compound No. 1) and 10% of urea pearls 
are mixed in a blender. The mixture is then ground in a pin mill. A powder 
is obtained, which is moistened with approximately 8% by weight of water. 
The moist powder is extruded in an extruder with a perforated roller. A 
granulate is obtained, which is dried and then crushed and screened, so as 
to retain only granules of a size between 150 and 2,000 microns 
respectively. 
EXAMPLE F 7 
Dispersible Granulates 
The following constituents are mixed in a blender: 
______________________________________ 
active substance (compound No. 1) 
75% 
wetting agent (sodium alkylnaphthalene- 
2% 
sulphonate) 
dispersing agent (sodium polynaphthalene- 
8% 
sulphonate) 
water-insoluble inert filler (kaolin) 
15% 
______________________________________ 
This mixture is granulated in a fluid bed, in the presence of water, and is 
then dried, crushed and screened so as to obtain granules of size between 
0.15 and 0.80 mm. 
These granulates can then be employed by themselves, in solution or in 
dispersion in water, so as to obtain the required dose. They can also be 
employed to prepare combinations with other active substances, especially 
fungicides, the latter being in the form of wettable powders or of 
granulates or aqueous suspensions. 
The compounds of formula (I) can, furthermore, be employed in the form of 
dusting powders; it is also possible to employ a composition comprising 50 
g of active substance and 950 g of talc; it is also possible to employ a 
composition comprising 20 g of active substance, 10 g of finely divided 
silica and 970 g of talc; these constituents are mixed and ground and the 
mixture is applied by dusting. 
As forms of compositions which are liquid or intended to constitute liquid 
compositions when applied, there may be mentioned solutions, in particular 
water-soluble concentrates, emulsifiable concentrates, emulsions, 
concentrated suspensions, aerosols, wettable powders (or spraying powder) 
and pastes. 
Emulsifiable or soluble concentrates in most cases contain 10 to 80% of 
active substance, while emulsions or solutions which are ready for use 
contain 0.001 to 20% of active substance. 
In addition to the solvent, the emulsifiable concentrates may, when 
necessary, contain 2 to 20% of suitable additives such as stabilizers, 
surface-active agents, penetrating agents, corrosion inhibitors, colorants 
or the adhesives referred to above. 
From these concentrates it is possible, by dilution with water, to obtain 
emulsions of any desired concentration, which are particularly suitable 
for application to crops. 
By way of example, here is the composition of some emulsifiable 
concentrates: 
EXAMPLE F 8 
______________________________________ 
active substance 400 g/l 
alkali metal dodecylbenzenesulphonate 
24 g/l 
nonylphenol condensate with 10 molecules 
16 g/l 
of ethylene oxide 
cyclohexanone 200 g/l 
aromatic solvent q.s. 1 liter 
______________________________________ 
According to another emulsifiable concentrate formulation, the following 
are employed: 
EXAMPLE F 9 
______________________________________ 
active substance 250 g 
epoxidized vegetable oil 
25 g 
mixture of alkylarylsulphonate and of 
100 g 
polyglycol ether and of fatty alcohols 
dimethylformamide 50 g 
xylene 575 g 
______________________________________ 
Flowables, which can also be applied by dusting, are prepared so as to 
obtain a stable fluid product which does not settle and usually contain 
from 10 to 75% of active substance, 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 antifoams, corrosion inhibitors, stabilizers, 
penetrating agents and adhesives and, as carrier, water or an organic 
liquid in which the active substance is poorly soluble or insoluble: 
certain organic solid substances or inorganic salts can be dissolved in 
the carrier to help prevent settling or as antifreezes for the water. 
By way of example, here is a flowable composition: 
EXAMPLE F 10 
______________________________________ 
compound 500 g 
polycondensate of ethylene oxide with 
50 g 
tristyrylphenol phosphate 
alkylphenol/ethylene oxide polycondensate 
50 g 
sodium polycarboxylate 20 g 
ethylene glycol 50 g 
organopolysiloxane oil (antifoam) 
1 g 
polysaccharide 0.5 g 
water 316.5 g 
______________________________________ 
Aqueous dispersions and emulsions, for example the compositions obtained by 
diluting a wettable powder or an emulsifiable concentrate according to the 
invention with water, are included within the general scope of the present 
invention. The emulsions may be of the water-in-oil or oil-in-water type 
and may have a thick consistency like that of a mayonnaise. 
As for compositions which are adapted to storage and to transport, these 
more advantageously contain from 0.5 to 95% (by weight) of active 
substance. 
The present invention also relates to a weeding method (especially of 
monocotyledon crop areas (wheat, corn, rice)), which consists in applying 
an effective quantity of a compound of formula (I) to the plants which are 
to be destroyed. 
During the application to a cultivated area, the application dosage should 
be sufficient to control the generation of adventitious plants without 
occasioning permanent substantial damage to the said crops. In this 
context, then, an effective dosage means the dosage which enables this 
result to be obtained. 
The products and compositions according to the invention are preferably 
applied to areas or terrains where it is desired to prevent the growth or 
the development of plants which have not yet grown (preemergence 
application). Nevertheless it will also be possible to employ a weeding 
method which consists in applying an effective quantity of a compound of 
formula (I) to the weeds to be removed when the latter have a green 
foliage, advantageously the monocotyledons. 
It is possible to operate so that the crop is sown before or after the 
treatment. 
The application dosage of active substance is generally between 1 and 8,000 
g/ha. 
The following examples illustrate the invention: 
EXAMPLE A 
Herbicidal Application During Preemergence of Plant Species 
A number of seeds, determined depending on the plant species and the seed 
size, are sown in 7.times.7.times.8 cm pots filled with light agricultural 
soil. 
The pots are treated by spraying with a spraying mixture in a quantity 
corresponding to a volume application rate of 500 l/ha and containing the 
active ingredient at the desired concentration. 
The treatment with the spraying mixture is therefore applied to seeds which 
are not covered with earth (the term spraying mixture is employed to 
denote generally water-diluted compositions, as applied to the plants). 
The spraying mixture employed for the treatment is a solution or suspension 
of the active ingredient in a water/acetone mixture in proportions of 
50/50, in the presence of 0.05% by weight of Cemulsol NP 10 
(surface-active agent, consisting of a polycondensate of ethylene oxide 
and alkylphenol, especially of a polycondensate of ethylene oxide and 
nonylphenol) and 0.04% by weight of Tween 20 (surface-active agent 
consisting of an oleate of a polycondensate of ethylene oxide derived from 
sorbitol). 
In the case of a suspension, the latter is obtained by mixing and milling 
the ingredients in a micronizer so as to obtain a mean particle size of 
less than 40 microns. 
After treatment, the seeds are covered with a layer of earth approximately 
3 mm in depth. 
The pots are then placed in troughs intended to receive the moistening 
water by subirrigation, and are maintained for 24 days at room temperature 
under 70% relative humidity. 
Scoring of the Herbicidal Activity 
The recording is carried out as follows: at the end of 24 days, a 
percentage (D) of destruction of the number of shoots in the treated pots 
is measured in relation to the number of plants in the untreated (control) 
pots. The remaining treated plants are used to measure the percentage of 
reduction in size (RS) relative to the control plants. 
The percentage of foliage volume not destroyed by the product is therefore 
given by the formula: 
##EQU1## 
This value A is converted into a score from 0 to 5 according to the 
following scale: 
______________________________________ 
Score 
______________________________________ 
0 to 10 5 (complete destruction) 
10 to 30 4 
30 to 50 3 
50 to 70 2 
70 to 90 1 
90 to 100 0 (no effect) 
______________________________________ 
The results obtained are shown after Example B for application rates of 
4,000 g/ha. 
EXAMPLE B 
Herbicidal Application During Postemergence of Plant Species 
A number of seeds, determined depending on the plant species and the seed 
size, are sown in 7.times.7.times.8 cm pots filled with light agricultural 
soil. 
The seeds are then covered with a layer of soil approximately 3 mm in depth 
and the seed is left to germinate until it gives rise to a plantlet at the 
appropriate stage. The treatment stage for graminaceous plants is the 
"second leaf being formed" stage. The treatment stage for dicotyledon 
plants is the "cotyledons open, first true leaf being developed" stage. 
The pots are then treated by spraying with a spraying mixture in a quantity 
corresponding to a volume application rate of 500 l/ha and containing the 
active ingredient at the desired concentration. 
The spraying mixture has been prepared in the same way as in Example A. 
The treated pots are next placed in troughs intended to receive the 
moistening water by subirrigation, and are maintained for 24 days at room 
temperature under 70% relative humidity. 
Scoring of the Herbicidal Activity 
The recording is carried out as follows: at the end of 24 days, a 
percentage (D) of destruction of the number of shoots in the treated pot 
is measured in relation to the number of plants in the untreated (control) 
pots. The remaining treated plants are used to measure the percentage of 
reduction in size (RS) relative to the control plants. 
The percentage of foliage volume not destroyed by the product is therefore 
given by the formula: 
##EQU2## 
This value A is converted into a score from 0 to 5 according to the 
following scale: 
______________________________________ 
Score 
______________________________________ 
0 to 10 5 (complete destruction) 
10 to 30 4 
30 to 50 3 
50 to 70 2 
70 to 90 1 
90 to 100 0 (no effect) 
______________________________________ 
The results obtained are shown after Table A for application rates of 4,000 
g/ha 
The plant species employed in these Examples A and B are: 
______________________________________ 
ENGLISH 
ABBREVIATIONS 
LATIN NAME NAME 
______________________________________ 
AVE Avena fatua Wild oat 
ALO Alopercurus myosuroides 
Slender foxtail 
ECH Echinochloa crusgalli 
Panic grass 
CYP Cyperus esculentus 
Chufa flat sedge 
DIG Digitaria sanguinalis 
Hairy fingergrass 
______________________________________ 
HERBICIDAL ACTIVITY AT PREEMERGENCE 
COMPOUNDS NO. 
AVE ECH DIG CYP ALO 
______________________________________ 
1 5 5 5 3 -- 
2 1 4 4 0 -- 
4 5 5 5 3 5 
8 2 4 5 1 2 
9 5 5 5 3 4 
11 1 5 5 3 5 
12 5 5 5 3 5 
13 5 5 5 2 5 
14 4 5 5 4 5 
15 5 5 5 3 5 
16 3 5 5 3 5 
17 3 5 5 3 5 
23 0 5 5 1 5 
24 5 5 5 2 5 
25 5 5 5 3 5 
______________________________________ 
HERBICIDAL ACTIVITY AT POSTEMERGENCE 
COMPOUNDS NO. 
ECH DIG ALO 
______________________________________ 
11 0 3 3 
13 4 3 2 
15 5 3 3 
16 3 0 3 
17 3 0 3 
24 3 1 3 
______________________________________ 
EXAMPLE C 
Test for Selectivity in Major Crops with Herbicidal Application During 
Preemergence of the Plant Species 
A number of seeds, determined depending on the plant species and the seed 
size, are sown in 7.times.7.times.8 cm pots filled with light agricultural 
soil. 
The seeds are then covered with a layer of soil approximately 3 mm in 
depth. 
The pots are then treated by spraying with a spraying mixture in a quantity 
corresponding to a volume application rate of 500 l/ha and containing the 
active ingredient at the desired concentration. 
The spraying mixture has been prepared in the same way as in Example A. 
The treated pots are then placed in troughs intended to receive the 
moistening water by subirrigation and are maintained for 24 days at room 
temperature under 70% relative humidity. 
Scoring of the Herbicidal Activity 
The recording is carried out as follows: at the end of 24 days, a 
percentage (D) of destruction of the number of shoots in the treated pot 
is measured in relation to he number of plants in the untreated (control) 
pots. The remaining treated plants are used to measure the percentage of 
reduction in size (RS) relative to the control plants. 
The percentage of foliage volume not destroyed by the product is therefore 
given by the formula: 
##EQU3## 
This value A is converted into a score from 0 to 5 according to the 
following scale: 
______________________________________ 
Score 
______________________________________ 
0 to 10 5 (complete destruction) 
10 to 30 4 
30 to 50 3 
50 to 70 2 
70 to 90 1 
90 to 100 0 (no effect) 
______________________________________ 
Thus, a product is judged to be selective in respect of the crop when the 
scored value A is 0 or 1. 
The results obtained are shown in Example C for application rates of 1 or 2 
or 4 kg of active ingredient per hectare, depending on the products. 
The plant species employed in this example are: 
(1) In the case of the adventitious plants 
______________________________________ 
ENGLISH 
ABBREVIATIONS 
LATIN NAME NAME 
______________________________________ 
ECH Echinochloa crus-galli 
Panic grass 
DIG Digitaria snaguinalis 
Hairy fingergrass 
SOR Sorghum halepense 
Johnson grass 
SET Setaria faberii Giant foxtail 
______________________________________ 
(2) In the case of the crops 
__________________________________________________________________________ 
ABBREVIATIONS 
LATIN NAME 
ENGLISH NAME 
__________________________________________________________________________ 
TRZ Triticum aestivum 
Spring wheat 
ZEA Zea mays Maize 
ORY Oryza sativa 
Rice 
GLX Glycine maximum 
Soybean 
__________________________________________________________________________ 
TEST FOR SELECTIVITY IN 
DOSE MAJOR CROPS HERBICIDAL 
COMPOUNDS 
APPLIED 
ACTIVITY AT PREEMERGENCE 
NO. (kg/ha) 
ECH 
DIG 
SOR 
SET 
TRZ 
ZEA 
ORY 
GLY 
__________________________________________________________________________ 
1 2 3 5 5 2 0 0 0 1 
4 2 5 5 1 5 0 0 1 0 
9 2 5 5 2 2 0 0 3 0 
13 2 4 5 2 4 0 1 2 0 
14 2 3 5 3 4 0 2 0 0 
15 2 5 5 5 5 1 0 3 0 
__________________________________________________________________________ 
As can be seen from the table of results of this Example C, many products 
exhibit an excellent antigraminaceous activity at preemergence while 
showing an excellent selectivity for 1 or 2 or 3 or 4 of the 4 tested 
crops=wheat, maize, rice, soybean.