Note: Descriptions are shown in the official language in which they were submitted.
i73~
The subject of the invention is herbicidal compounds and their use
in preventing, eradicating or reducing the presence of grasses from a tract
of land by applying to the tract of land or said grasses a herbicidally
effective amount of a compound of the general formula
X ~ ~ Y-C-Z
(R)n (Rl)n
wherein
R represents the same or different substituents from the group consisting of
halogen, CF3, (Cl-C6)-alkYl,
Rl represents halogen, CF3
R2 represents (Cl-C4)-alkyl;
n represents 1 or 2;
nl represents 0 or 1;
X and Y represent 0 or S and
Z represents -CN, -CHO,
R3~
~ \ R ~ wherein R3 represents hydrogen, (Cl-C6)
S 4~' alkyl, methoxy, (C5-C6)cycloalkyl, benzyl,
or phenyl, and R4 represents hydrogen,
(Cl-C6)alkyl, (C5-C6)cycloalkyl or benzyl,
or wherein R3 and R4 together represent
pyrrolidine and morpholine
~t~ 73~
C ~ N IN-R6 C~5 N INI
\ N _ - N \ N - N
R6
wherein R6 represents hydrogen or (Cl-C4) alkyl;
X-Rll wherein Rlo represents (Cl-C6)alkyl,
-C-R (C3-C6) alkenyl, (C5-CG cycloalkyl, phenyl.,
X-R12 halophenyl, trifluoromethylphenyl or hydrogen
Rll and R12 each represent ~Cl-C4) alkyl or
together represent an alkylene chain having
2 - 3 carbon atoms;
OH
-CH-SO (~)cat ~+) wherein cat( )is the cation of an inorganic
or organic base,
-CH-N-W-Rlo/ wherein W represents a direct bond or an
oxygen atom.
The alkyl or alkenyl groups mentioned may be straight-chained or
branched.
t~
.
73~
Of the radicals mentioned, the ones that are preferred
are those in which (R) represents up to 2 Cl, Br, CF3; in
particular 4-Cl, 2,4-Cl, 2-Cl-4-Br, 4-CF3 and
2-Cl-4-CF3;
R2: CH3;
nl: 0 or ~Rl)nl=Cl in the 2 position to the radical Y
X, Y, : oxygen;
Z; CN, C(S)-NH2
,~N-NH
-C/\ I
N=N
OH ~ NH ~ NH2- +
-f-H -C or -C A
SO3 cat NH2 NH2_
and cat : Na , K or NH4 and A : Cl , HSO4 , Br .
A further subject of the invention is the compounds
of formula I provided that Z does not represent
-C-NH2 , -C-NH2 or -CHO if
S NH
(R)n stands for 4-CF3.
The compounds of formula I can be prepared, for
example starting from parent substances of the formula
X ~ Y -H II
n (Rl)nl
~9573~
according to numerous processes known for similar compounds.
Thus, compounds of formula II can be reacted in a manner known
per se with those of the formula
12
B-C-Z III
H
wherein B represents halogen, preferably chlorine, bromine or a
sulfo ester group, for example with ~-Cl- or ~-Br-acetonitrile or
-propionitrile, optionally in the presence of acid-binding agents,
and they can then be converted into other compounds of formula
I by reactions customary in organic chemistry.
Some processes suitable for the production of
compounds of formula I are to be described in the following
and in the examples.
::
l~g~73~
Process 1
_
Nitriles of formula I are obtained by reacting
compounds of formula II with the corresponding halogen nitriles
~III, Z = CN) or, preparatively, by splitting off water from
the corresponding acid amides of formula I (Z = C~0)-NH2), e.g.
by means of phosphorus pentachloride, phosphorus pentoxide
or thionyl chloride.
Process 2
Unsubstituted thioamides of formula I ~Z = -C~S)-NH2)
are obtained, e.g. by reacting the corresponding nitriles of
formula I with hydrogen sulfide or also by reacting the corres-
ponding acid amides with halogenating agents such as phosphorus
halides and then reacting with hydrogen sulfide in the presence
of acid binders. Substituted thioamides ~Z = -C~S)-NR3R4) with
R3 and R4 = H result if the above reaction is effected in the
presence of an amine of the formula HNR3R4 or if a reaction is
subsequently effected with such an amine.
Process 3
/,N - ~-H
Tetrazole derivatives of formula I ~Z = -C I )
`~N - N
are obtained by reacting the corresponding nitriles of formula I
with alkali metal azides and/or ammonium azides.
Process 4
Amidines of formula I or derivatives thereof with
573~
H ~ R7 +
ZC~ 7 ~N-R A or ~N~ A
\N\R3 \ N~R3 _ \~ ~R3
R4 R4 R4
are obtained, for example~ by reacting the corresponding acid
amides of formula I (Z = -C~O) -NR3R4) with halogenating agents
and then reacting with amines of the formula H2NR7 or 1~R7R8,
optionally in the presence of acid bindersJ or by reacting the
said acid amides with dimethyl sulfate and then reacting with
the said amines, or by reacting the corresponding imino esters
~N-R7
(Z = -C
\0- (Cl-C6) alkyl
with amines of the formula HNR3R4.
Process 5
Imino esters or imino-thioesters of formula I or the
acid addition salts thereof
~1l i
~N - R3
~Z = -C A
X - Rg l
are obtained by reacting the corresponding acid amides (Z = -C(O)NHR3)
with halogenating agents to form the imide halide and by further
reaction with alcohols or mercaptans of the formula HXRg,
optionally in the presence of acid binders.
Process 6
Ketals or acetals of formula I
73~
X-Rll
(H = -C-Rlo
X-R12
are obtained by reacting compounds of formula II with corresponding
compounds of formula III, or from compounds of formula I (Z = C~
Rlo
by reaction with alcohols of the formula HORll or HOR12 or mercaptans
of the formula HSRll or HSR12 under conditions used for the
formation of thioacetals or thioketals, e.g. in the presence of
acid or (where X = 0) in the presence of ortho-esters.
Process 7
a) Aldehydes of formula I (Z = -CH0) are obtained, e.g. in a
manner known per se by gentle selective oxidation of the
corresponding alcohols (Z = -CH20H) - cf. e.g. J. org. Chem. ~9,
(1974), page 3304 - for example by oxidizing with dimethyl
sulfoxide and dicyclohexylcarbodiimide in the presence of
phosphoric acid as the acid catalyst, or by the reduction of the
corresponding acid chlorides (Z = -C(O)Cl) under Rosenmund-
reduction conditions in ~he presence of contaminated noble metal
catalysts, or by the reduction of corresponding acid derivatives
(esters) with metal hydrides, e.g. LiAlH4 or by the reduction
of the corresponding imide-chlorides
~ NH
(Z = -C ) with inorganic reducing agents such as, for example,
tin (II)chloride, or by the reduction of the nitriles according to
the invention of formula I (Z - CN) in ether with tin(II)chloride in
the presence of hydrogen chloride
or by the acid cleavage of the acetals obtainable according to
573S
process 6.
b) Bisulfite adducts of formula I ~ Z = -C-OH cat( ) )
SO3(-)
are obtained in a manner known ~ se by reacting aldehydes of
formula ~ (Z = -CHO) with bisulfites (hydrogen sulfites~.
Process 8 H,
Compounds of formula I, in which Z = -C=N-W-Rlo and
which are to be understood as oximes or Schiff's bases of aldehydes
of formula I (Z = -CHO), are obtained by reacting these aldehydes
with amines or hydroxylamines of the formula H2N-W-Rlo (IV)
under conditions known for the production of Schiff's bases and
oximes. When W = oxygen, compounds of formula I with
Z = -HC=N-OH can also be reacted with compounds of the formula
B-Rlo (B = halogen, preferably chlorine or bromine) to form the
desired compounds.
Processes known ~ se can be used for the production
of the acid amides and acid chlorides that are in some cases
used as starting substances.
The compounds according to the invention of the
general formula I have herbicidal action against a wide range
of harmful grasses, these compounds being at the same time
very compatible with useful dicotyledons as well as, to an extent,
with various types of cereal. Thus, the compounds of the
general formula I are suitable for the selective combating of
harmful grasses in crop plants.
The active substances according to the general
5~3~i
formula I constitute 2-95% of the content of the active agents,
according to the invention. These agents can be applied in the
normal forms of preparation as emulsifiable concentrates,
wettable powders, sprayable solutions, dusts or granulates.
Wettable powders are preparations that can be evenly
dispersed in water and that contain, apart from a diluent or
~nert substance, also wetting agents in addition to the active
substance, e.g. polyoxyethylated alkylphenols, polyoxyethylated
oleylamines or stearylamines, alkyl sulfonates or alkyl-phenyl
sulfonates and dispersing agents, e.g. sodium lignin-sulfonate
sodium 212'-dinaphthylmethane-6,6'-disulfonate or also sodium
oleylmethyl tauride.
Emulsifiable concentrates are obtained by dissolving
the active substance in an organic solvent, e.g. butanol,
cyclohexanone, dimethylformamide, xylene or also high-boiling
aromatic substances.
Dusts are obtained by grinding the active substance
with finely divided, solid substances, e.g. talcum, natural
clays, such as kaolin, bentonite, pyrophillite or diatomaceous
earth.
Sprayable solutions, as widely marketed in spray-cans,
contain the active substance dissolved in an organic solvent and
in addition, as a propellant, e.g. a mixture of fluorochloro-
hydrocarbons.
Granulates may be produced either by spraying the active
substance onto adsorptive, granulated inert material or by applying
- 10 -
1~''9573~
active substance concentrates, by means of adhesives, e.g.
polyvinyl alcohol, sodium polyacrylate or also mineral oils,
i to the surface of carrier substances, such as sand, kaolinite,
or of granulated inert material. Also suitable active substances
can be produced in the manner usual for the production of
granulated fertilizer materials - optionally in admixture with
fertilizers.
In the case of herbicidal agents, the concentrations
of the active substances in commercial formulations may vary.
In wettable powders the active substance concentration varies
e.g. between approximately 10% and 95% and the rest consists of
the formulation additives indicated above. In emulsifiable
concentrates the active substance concentration is approximately
10% to 80%. Dust formulations in most cases consist of 5-20%
of active substance, and sprayable solutions of about 2-20%.
In the case of granulates, the active substance content depends
partly upon whether the active compound is liquid or solid and
upon what granulation auxiliaries, fillers etc. are used.
In order to apply them, the commercial concentrates
are optionally diluted in the normal manner, e.g. by water in
the case of wettable powders and emulsifiable concentrates.
Dusts and granulated preparations as well as sprayable solutions
are not diluted with other inert substances before application.
The amount which must be applied varies with external conditions
such as temperature, moisture int. al. It can vary within a
wide range, e.g. between 0.1 kg/ha and 10 kg/ha of active
substance, but is preferably between 0.3 and 3 kg/ha.
1~9573~
The active s~lbstances according to the invention may
be combined with other herbicides and soil insecticides.
- 12 -
~ss~3~
Examples of formulation
Example A
An emulsifiable concentrate is obtained from:
15 parts by weight of active substance
" " " " cyclohexanone as the solvent
" " " " oxyethylated nonylphenol (10 EO)
as the emulsifier.
Example B
A wettable powder that is readily dispersable in water is
obtained by mixing
25 parts by weight of active substance
64 " " " " kaoline-containing quartz as the
inert substance
" " " " potassium lignin sulfonate and
1 " " " " sodium oleylmethyl tauride as
the wetting and dispersing agent
and grinding the whole in a pin mill.
Example C
A dust is obtained by mixing
10 parts by weight of active substance
go " " " " talcum as the inert substanc0
and pulverizing the whole in a cross beater mill.
Example D
A granulate consists, e.g. of approximately
2 - 15 parts by weight of active substance
98 - 85 " " " " inert granulate carrier materials
such as~ for example, atapulgite,
pumice and quartz sand.
- 13 -
~9~73~i
Examples of preparation
Example 1
2- [4'-(4"chlorophenoxy)-phenoxy] -propionitrile 125 g (0.429 mol) of 2- [4'-
~4"chlorophenoxy)-phenoxy] -propionic acid amide are heated for 10 hours
under reflux in 500 ml of dry toluene with 66.3 g (0.55 mol) of thionyl chloride.
Excess thionyl chloride and toluene are distilled off under reduced pressure.
The viscous residue remaining is distilled. After distillation 111 g (94.6%
of theory) of Z- ¦4'-(4"-chlorophenoxy)-phenoxy] -propionitrile with b.p.
0 05 : 173C are obtained. The distillate solidifies in the receiver and has
a melting point of 79C. r~ CH3
Cl- ~ 0- ~ -0-C-C_N
Prepared in a similar manner were:
Example [
No. Compound of Formula I b.p. [ C] m.p. C
__
2 F C- ~ 0- ~ 0-C-CN 0.05:160 58 - 69
3 F3C- CO ~ ~ ~ 0-C-CN 0.1 :175
4 Cl- ~ 0- ~ 0-C-CN 0.o5:l87 65 - 66
H C- ~ - ~ -0-C-CN 0.05:159
6 H3C- ~ ~ CH3 0.02:178
7 ~ ~ H 73 - 74
- 14 _
~q~9S73~
Example 8
2- [4'-~4"-chlorophenoxy)-phenoxy] -propionic acid thioamide 150 g (0.55 mol)
of the nitrile obtained in Example (1) are reacted in 150 ml of fluid hydro-
gen sulfide with 6.7 g (0.091 mol) of diethylamine for 6 hours at 70C under
its own pressure. The solid residue is recrystallized from ethanol. 150 g
(88% of theory) of 2- ¦4'-(4"-chlorophenoxy~-phenoxy~ -propionic acid thio-
amide with a melting point of 127 - 128C are obtained.
Cl- ~ -0- ~ o_CclH3 C-NH2
Prepared in a similar manner were: [o ]
Example No. Compound of Formula I m.p. _ C
9 ~ F C- ~ 0- ~ CH3 ~ S
IO l Cl- ~ -0- ~ 0-C- ¦155 - 156 (Ethanol)
~ r__~ CH3
11 Br- ~ -O- ~ O-C-C \
Cl CH3~5
12 F C- ~ 0- ~ o_¦_c
13 ~ ~ CH3 ~ 5
14 H C- ~ 0- ~ -0-C-C ~
5~3~i
Example 15
2- [4'-(4"-trifluoromethylphenoxy)-phenox~ -thiopropionic acid N-butylamide.
17.1 g (0.05 mol) of the thioamide obtained in Example 8 are reacted for 3
hours at 80C with ll g (0.15 mol) of n-butylamine. After cooling, approxi-
mately 50 ml of water are added. The precipitate formed is sucked off and
washed neutral with water. Recrystallization from cyclohexane yields 18.2 g
(91.3~ of theory) of 2- [4'-(4"-trifluoromethylphenoxy)-phenoxy] -thiopro-
pionic acid N-butylamide with a melting point of 88C.
F C- ~ 0_ ~ CH3 ~ S
H NH-CH2-CH2-CH2-CH3
Prepared in a similar manner were:
Example No. Compound of Formula I m.p. [ C]
16 ~ ~ H ill-CH2- ~ 119 - 120
17 Cl- ~ -0- ~ 0-C-C-NH-(C4Hg)ll 72.5 (Hexane~
18 Cl- ~ 0- ~ -0-C-C-N ~ 0
19 Cl- ~ ~ -0- -N~C2H5)2
Cl- ~ -0- ~ 0-CH~lsl-N 107.5
- 16 -
35735
Example No. Compound of Formula I m.p. [ C
CH3 S
21 F C- ~ O- ~ -O-C-C
H NH-
Example 22
l- ~4'-(4"-trifluoromethylphenoxy)-phenoxy] -l-(tetrazol-5'-yl)-ethane 39.9 g
(0.13 mol) of the nitrile obtained in Example 2 are added to a suspension of
9.3 g (0.143 mol) of sodium azide and 7.65 g (0,143 mol) of ammonium chlGride
in 200 ml of dimethylformamide and heated, while stirring, ~o 105-110C.
The reaction is complete after 7 hours. Dimethylformamide is distilled off
under reduced pressure. The residue remaining is taken up in 200 ml of tolu-
ene and washed with water. Toluene is distilled off under reduced pressure.
After drying in vacuo 34.6 g (76% of theory) of l- [4'-(4"-trifluoromethyl-
phenoxy)-phenoxy] -l-(tetrazol-5'-yl) ethane with a melting point of 122-
123C are obtained.
~ ~ ~H3 N - N-H
Prepared in a similar manner were:
Example [o
No. _Compound of Formula I m.p. C
23 Cl- ~ -O- ~ -O-C-C ~ ¦ 133.5-135 (EtOH/
24 ~ ~ Ul3 N - N H 115
~ ~ H N - N
- 17 -
~9~3~
Example 26
2- [4'-(2",4"-dichlorophenoxy)-phenoxy~ -propionaldehyde as a bisulfite
adduct
a) 2- C4'-(2",4"-dichlorophenoxy)-phenoxy~ -propionaldehyde
103.6 g (0.3 mol) of 2- [4'-(2",4"-dichlorophenoxy)-phenoxy] -pro-
pionic acid chloride are dissolved in 5 times this amount of absolute xylene,
regulated with the addition of Pd/BaS04 catalyst, reduced with quinoline S
at 135C for 2-4 hours in a hydrogen atmosphere. The catalyst is filtered
off Cl CH3 0
Cl-~_o_ ~O-C-C~
b) Bisulfite adduct of 2- ~4'-(2",4"-dichlorophenoxy)-phenoxy] -propio _
aldehyde.
The solution of the aldehyde in xylene obtained in Example 28a is
reacted with 100 ml of saturated sodium bisulfite solution while stirring
thoroughly until the precipitation of the bisulfite adduct is quantitative.
The precipitate is removed by suction and then washed with xylene and diethyl
ether. 87.3 g (70% of theory~ of bisulfite adduct, calculated on the acid
chloride used, are obtained. Cl 1 3/
Cl- ~ 0- ~ 0-C-C-II
S3 (~)Na(+)
20Analysis Calculated: C 43.4 H 3.15 S 7.7
found: C 42.1 H 3.5 S 7.3
prepared in a similar manner were:
- 18 -
lq~ 73S
Example
No.Compound of Formula I m.p.[ C]
27 F3C- ~ o_ ~ -O-C-C-H with
H SO ~ a~3 decomp-
3 osition
28 ~ ~ CH3 OH 170 - 172
29 ~ 3
Example 30
2- [4'-(2",4"-dichlorophenoxy)-phenoxy] -propanal-diethylacetal 30 g ~0.072
mol) of the bisulfite adduct obtained in Example 28 are stirred at 60C in
a mixture of 100 ml of ethyl acetate and 80 ml of 1 N sul~uric acid under
nitrogen until the development of sulfur dioxide is completed. The organic
phase is neutralized with bicarbona~e solution and dried. Most of the ethyl
acetate is distilled off under reduced pressure. The aldehyde thus obtained
is added, under nitrogen, to a solution of 30 ml of absolute ethanol, 0.6 g
of ammonium nitrate and 30 g of triethyl orthoformate. The reaction mixture
is left to stand until the end of the reaction (approximately 8-10 hours).
The salt is separated and the alkalinity of the remaining solution is adjust-
ed with morpholine. The solvent is distilled off. The remaining oil is
distilled. The distillation yields 22.5 g (81% of theory) of 2- ~4'-(2",4"-
dichlorophenoxy)-phenoxy] -propanal-diethylacetal with b.p. o 06:185 C.
Cl- ~ -O ~ O 1 3/ 2 S
-- 19 -- ...
l~R~'73
Obtained in a similar manner are:
Example Compound of Formula I B.p.[ C]
No.
CH3 0C2H5
31 F3C~-O ~ C,-C-H
32 Cl-- ~ O ~~)-- 0-C-C-H 185 / 0.1 Torr
H 0C2H5
33 Br ~Cl 0-r-C-H
Cl H 0C2H5
34 Cl--~ 0 -~--0-C-C-H 180-181/0.07 Torr
H OCH3
35F3C-- ~ 0 -~- C-H 158 / O.O5 Torr
36Cl ~ 0 ~ 0-C-C-ÉI
l-l 0CE-13
37~ 3r --~ O--~>--0-C- -H
El OCE13
Example 38
2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propanal-N-propylamine 15 g (0.036 mol)
of the bisulfite adduct obtained in Example 28 are stirred at 60C in a mixture
of 100 ml of ethyl acetate and 50 ml of 1 N sulfuric acid under nitrogen until
the development o:E sulfur dioxide is completed. The organic phase is
neutralized with
- 20 -
~: :
573~
bicarbonate solution. The solution of the aldehyde in ethyl acetate thus
obtained is added dropwise under nitrogen to a solution of 2.95 g (0.05 mol)
of propylamine in 50 ml of ethyl acetate with external cooling. The reaction
mixture is left to stand for 12 hours at room temperature. Ethyl acetate
is distilled off under reduced pressure. The residue remaining is freed of
adhering impurities by means of column chromatography. 9.6 g (76% of theory)
of 2- [4'-(2",4"-dichlorophenoxy)-phenoxy~ -propanal-N-propylimine are
obtained.
Cl- ~ -0- ~ 0-C-CH=N-C3H7
Analysis caluculated: C 61.3 H 5.45 Cl 20.1 N 3.95
found: C 60.4 H 5.4 Cl 20.2 N 4.3
- 21 -
` ~
~g5735
Biological Examples
Example I
Seeds of various grasses were sown in pots and the preparations
according to the invention formulated as dusting powders are sprayed in dif-
ferent quantities onto the surface of the soil. The pots were then placed in
a greenhouse for 4 weeks. The result of treatment (also in the case of the
following examples) was determined by assessment according to Bolle's scheme
~Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 16, 1964, 92-94):
-
~armful effect in %
_Number _ Weeds on Crop plants
100 0
2 97.5 to < 100 > O to 2.5
3 95 to ' 97.5 ' 2.5 to 5
4 90 to < 95 > 5 to 10
85 to < 90 ~10 to 15
6 75 to < 85 >15 to 25
7 65 to < 75 '25 to 35
8 32.5 t~ ' 65 ~ 35 to 67.5
9 0 to ~ 32.5 ~ 67.5 to 100
The procedure was the same with the herbicidal comparison agents used, Fluro-
difen (4-nitrophenyl-~2'-nitro-4'-trifluoromethylphenyl)-ether) and Mecoprop
(2-(4'-chloro-2'-methylphenoxy)-propionic acid. The results collated in
Table I show that the claimed compounds are, on average, more effective against
grasses than the two herbicides used for comparison. Further, the claimed com-
pounds from Examples 1, 10, 23, 24, 26 and 27 had a similar effect against
grasses.
Example II
Grass seeds were sown in pots and grown in a greenhouse.
- 22 -
5735
3 weeks after sowing the preparations according to the invention formulated
as dusting powders were sprayed in different quantities onto the plants and
after 4 weeks' standing in the greenhouse the effect of the preparations
was assessed. In this case, too, Flurodifen and Mecoprop were used as the
herbicidal comparison agents. Although with this application process the
claimed compounds were not quite as effective as in the preemergence process
described in Example I they were more effective against grasses than the two
comparison agents (Tab. II). Further, the claimed compounds from Examples
1, 109 23, 26 and 27 had a similar effect against grasses.
Example III
In another experiment substances according to the invention were
applied to numerous crop plants before emergence. Evaluation showed (cf.
Table III) that all types of useful dicotyledon tested toerated treatment with
2.5 kg/ha 4, 2, 9 and 8. The same also applies to onions.
In addition, wheat and barley are not harmed either when the com-
pounds according to Examples 4 and 9 are applied.
.,
73~
Table I
Weed assessment figures in the case of pre-emergence treatment
Example Quantity P l a n t t y p e s
No. (kg/ha AS) L SA L0 EC
9 2.5 2 2
0.6 3 3 2
8 2.5
0.6 2
4 2.5 4 1 1 2
0.6 6 2 2 3
2 2.5
0.6 2
22 2.5 4 2 3 3
0.6 6 4 6 5
1 2.5 2
0.6 3 3 - 1
3 2.5 2 1 - 2
0.6 3 2 - 3
7 2.5 2
0.6 3 1 - 2
2.5 - 1 - 3
0.6 - 2 - 4
2.5
0.6 2
16 2.5 - 1 - 1
0.6
17 2.5 2 2 - 3
23 2.5 - ~ - 2
0.6 - 4 - 4
- 24 -
`
16'9573~
Example Quantity P 1 a n t t y p e s
No. (kg/ha AS) AL ~A L0 EC
24 2.5 4 3 ~ 4
26 b) 2.5 2 1 - 1
0.6 3
27 2.5
0.6
28 2.5 2 2
0.6 4 2 - 2
2.5 - 2 - 3
32 2.5 4 3 - 3
34 2.5 3 1 - 1
0.6 5 3 - 2
2.5
0.6
38 2.5 4 2 - 2
______________________.~_______
Fluorodifen 2.5 7 1 1 4
0.6 8 5 8 8
Mecoprop 2.5 4 3 5 3
0.6 7 6 8 7
._,
AL = Alopecurus myosuroides
SA = Setaria lutesceus
L0 = Lolium multiflorum
EC = Echinochloa crus-galli
- 25 -
i7~
~able II
Weed-assessment figures in the case of post-emergence application
Example Quantity P 1 a n t t y p e s
No. (kg/ha AS) AV AL SA L0 EC
9 2.5 9 2 1 6
0.6 9 6 8 8 2
8 2.5
0.6 3 4 1 2
4 2.5 9 g 3 3
0.6 9 9 7 7 5
2 2.5
0.6 8 5 2 2
24 2.5 9 2 4 8
0.6 9 7 9 9 3
22 2.5 2 3 2 5
0.6 9 6 7 7 5
1 2.5 - 2 5 - 1
0.6 - 7 7
3 2.5 - 1 4
0.6 - 4 7 - 4
7 2.5 - - - - 4
0.6 - - - - 8
2.5 - - - - 2
0.6 - - - - 7
23 2.5 - - 3 - 3
0.6 - - 8 - 7
26 b) 2.5 - 3
0.6 - 6
i'735
Example Quantity P 1 a n t t y p e s
No. (k~!ha AS) _ AV AL SA L0 EC
27 2.5 - 1 1 - 1
0.6
34 2.5
0.6 - 6 6 - 2
2.5
0.6 - - - - 2
___________________ ______________________________________________________
10Fluorodifen 2.5 8 8 2 6 4
0.6 8 8 3 8 6
Mecoprop 2.5 8 8 7 8 8
0.6 9 9 8 9 9
AV = Avena fatua
- 27 -
,
:
5735
Table III
Effect on crop plants~ pre-emergence process.
Quantity: 2.5 kg/ha
Example No.
Plant types 4 2 9 8
Dwarf bean
Sugar beet 1 2
Spinach
Sunflower
Rape
Alfalfa
Pea 1 2
Field bean
Lettuce
Cabbage
Flax
Onion 3 3 1 2
Tomato 2 2
Carrot
Celery
Cucumber 1 3
Soya bean
Cotton 3
Tobacco
Wheat 1 -- 1 -
Barley 1 - 1 -
- 28 -
