Note: Descriptions are shown in the official language in which they were submitted.
It is known that quite a number of chlorine- and tri-fluoromethyl-
substituted 4-phenoxyphenoxy~-propionic acid esters exhibit a specific effect
against economically important weed grasses, such as annual blackgrass, wild oat,
barnyard grass, large crabgrass, bristle grass, ryegrass and couch grass ~cf.
DT-OS 2,2Z3,~94 and DT-OS 2,433,067). 2-Chloro-4-bromo-substituted 4-phenoxy-
phenoxy-~-propionic acid esters have also been proposed for the same purpose
(cf. DT-OS 2,6~1,548). The compounds of this type (defined in the following as
type (1)) can be used, not only in sugar beet, leguminosae, vegetables and otherdicotyledonous crop plants, but partly also in barley, wheat and rye, preferablyby spraying after emergence of the plants.
It is also known that many herbicidal substances have a good effect
against dicotyledonous weeds, but no or only a ~eak effect against weed grasses.Compounds of this type (def~ned in the follo~ing as type (2)) comprise, inter
alia, Desmedipham and Phenmedipham Ccf. 3rd Symposium about novel herbicides,
Paris 196Y), N-~3-chloro-4-ethoxy-phenyl)-N',N'-dimethyl urea ~cf. DT-OS
2,221,795~, Methabenzthiazuron (cf. Biol. Bundesanstalt fur Land- und
Forstwirtschaft, Pflanzenschutzmittelverzeichnis 1975/76, page 105), and
Metamitron (cf. Zeitschrift fur Pflanzenkrankheiten und Pflanzenschutz, SH VII,
1975, pages 367 - 374).
It has now been found, surprisingly, that the combined application of
compounds of types (1) and t2) produces a more than additive (i.e. synergistic)
effect in the control of weed grasses.
It is therefore, the object of the present invention to provide herbi-
cidal compositions characterized by a content of
1) 2-~4-(4'-chlorophenoxy)-phenoxy]-propianic acid lower alkyl ester (I),
or
,~
2-[4-(2'J4'-dichlorophenoxy)-phenoxy]-propionlc acid lower
al~yl ester ~ or
2-[4-(2'-chloro-4'-bromophenoxy)-phenoxy]-propionic acid
lower al~yl ester ~ , or
2-[4-(4'-trifluoromethylphenoxy)-phenoxy]-propionic acid
lower alkyl ester ~IV)
in combination with
2) 3-ethoxy-carbonylaminophenyl-N-phenyl carbamate
(pesmedipham; A), or
3-methoxycarbonylaminophenyl-N-(3'-methylphenyl)-carbamate
(Phenmedipham; B), or
N-3-chloro-4-ethoxyphenyl-N',N'-dimethyl urea (C), or
N-(2-benzthiazolyl-N,N'-dimethyl urea
(Methabenzthiazuron; D), or
3-methyl-4-amino-6-phenyl-1,2,4-triazin-5(4H~-one
(Metamitron; E)
with the proviso that combinations of I or II with B or E and of IV with
C or D are not claimed.
The isobutyl ester of I and the mPthyl esters of II, III and
IV are preferred as type (1) compounds. The ratio of compounds (I - IV)
to (A - E) can vary within wide limits between about 1:0.5 and 1:17.
The preferred ratio in each case depends on the particular compounds to
be mixed, the weeds to be combated and their development stage. Combina-
tions of compounds I, II or III with A or of III with B are preferably
applied in a ratio of from 1:1 to 1:4, whereas combinations of IV with
A or IV with B are preferably used in a ratio of 1:0.5 to 1:2. Com-
~OE 76/F 315
binations of compounds I, II and III with compounds C or D arepreferably used in a ratio of from 1:2 to 1:6, and combinations
of II~ or IV with E preferably in a ratio of from l:6 to 1:14.
The herbicidal compositions according to the invention can
be used in the form of wettable powders, emulsifiable concen-
trates or dusts ana may contain the usual formulation auxilia-
ries such as wetting agents, dispersing agents, solid or li-
quid inert substance~ and grinding auxiliaries or solvents.
~ Suitable carrier materials are mineral substances such
as aluminum silicates, aluminum oxides, kaolin, chalks, sili-
ceous chalks, talc, kieselguhr, or hydrated silicic acids or
preparations of the aforesaid mineral substances with special
additives, for example chalk treated with sodium stearate. As
carrier material for liquid formulations all usual and suitable
organic solvents can be used, for example toluene, xylene,
diacetone alcohol, isophorone, gasolines, paraffin oils,
dioxane, dimethylformamide, dimethylsulfoxide, ethyl acetate,
butyl acetate, tetrahydrofurane, chlorobenzene and others.
As adhesives glue-like cellulose products or polyv1nyl
alcohols can be used.
Suitable wetting agents are appropriate emulsifiers such
as oxethylated alkylphenols, salis of aryl or alkyiaryl sulfo-
nic acids, salts of ethoxylated benzenesulfonic acids and
soaps.
As dispersing agents there may be used cellulose waste
liquors tsalts of sulfite waste liquors~, salts of naphthalene
sulfonic acid and in some cases also hydrated silicic acids
or kieselguhr.
29 Suitable grinding auxiliaries are inorganic or organic salts
~ 4 _
such as sodium sul$ate, ammonlum sulPate, sodiwn carbonate, sodium bicarbonate,
sodium thiosulfate, sodium stearate, and sodium acetate.
In general, the herbicidal compositions according to the invention are
contained in the formulations in an amount oÇ from 2 to 75 %. Optionally, the
formulations may further contain other known acti~e ingredients.
The amounts ~o be applied in practice vary within wide limits. Com-
positions of I, II or III with A and of III with B are used in a total amount offrom 0.5 to 5, preferably l to 3 kg per hectare, compositions of IV with A and
of IV with B are used in an amount of from 0.1 to 5 and preferably 1 to 3 kg
per hectare, compositions of I, II or III with C or D are used in an amount of
from 0.1 to lO, preferably 0.5 to 5 kg per hectare and compositions III or IV
with E are used in an amount of from l to 15 and preferably 5 to 10 kg per
hectare.
Formulations suitable for application can be prepared in simple manner
according to the following prescriptions.
FORMULATION EXA~PLE 1:
25.0 parts by weight of compound II (methyl ester~ are liquefied at 60C and
absorbed on
18.7 parts by weight of synthetic silicic acid ~mixture l)
Separately, a mixture of
26.2 parts by weight of compound A
8.0 parts by weight of sodium dinaphthylmethane-disulfonate
2 1 parts by weight of partially saponified polyvinyl acetate
3.0 parts by weight of sodium alkylnaphthalene-sulfonate
5.0 parts by weight of sodium b~carbonate and
9.0 parts by weight of synthetic silicic acid
~,
~ HOE 76/F 315
is prepared and finely ground on a pin mill (mixture 2). Next,
mixtures 1 and 2 are blended and ground again on a slowly run-
ning cross beater mill to obtain the ~ettahle powder ready
for use.
Ratio of A toII- 1.05:~v
FORMULATION EXAMPLE 2:
26.2 Parts by weight of compound A
19.0 parts by weight of diatomaceous earth
8.0 parts by weight of sodium dinaphthylmethane-disulfonate
2.0 parts by weight of sodium alkylnaphihalene-sulfonate
0.5 part by weight of sodium dodecylbenzenesulfonate and
6.6 parts by weight of sodium bicarbonate
are mixed and finely ground at high speed in a pin mill
(mixture 1~.
At 60 C
20.0 parts by weight of compound III(methyl ester~ are lique-
fied and adsorbed on
15.1 parts by weight of synthetic silicic acid
(mixture 2~.
Both mixtures are ground in a slowly rotating cross ~eat~r mill
to give a wettable powder.
Ratio of A to III = 1~31:1
FORMULATION EXAMPLE 3;
A mixture 1 is prepared as described in Example 2 from
26.2 parts by weight of compound B
19.0 parts by w~ight of kieselguhr
12.0 parts by weisht of sodium lignin-sulfonate
a, 0 parts by weight of sodium alkylnaphthalene-sulonate ~nd
29 1.1 parts by weight of partlally saponified polyvinyl acetate~
- 6 -
HOE_76/F _15
A mixture 2 is prepared as descrihed in Example 2 from
20.0 parts by weiyht of compound III as methyl ester and
15.1 parts by w~ight of synthetic silicic acid
and both mixtures are ground in a cross beater mill.
Ratio of B to III = 1.31:1.
FORMULATION EXAMPLE 4:
30.0 Parts by weight of compound B
8.0 parts by weight of sodium dinaphthylmethanedisulfonate
1.0 part by weight of dioctylsulfosuccinic acid ester in
the form of its sodium salt
2.0 parts by weight of sodim oleyl-N-methyltauride
0.5 part by weight of sodium palmitate
5.0 parts by weight of sodium bicarbonate
15.0 parts by weight of synthetic silicic acid and
3.5 parts by weight of diatomaceous earth
are mixed and finely ground at high speed in a pin mill
(mixture 1). 18 Parts by weight of the methyl ester of com-
pound IV are liquefied at 60 C and adsorbed in a high speed
mixer on 14 parts of synthetic silicic acid (mixture 2).
Mixtures 1 and 2 are then blended and ground in a slowly rot-
ating cross beater mill to give a wettable powdex ready for use.
Ratio of B to IV = 1.67:1.
FORMULATION EXAMPLE 5~
12.0 Parts by weight of compound T as isobutyl ester
are liquefied at 60~ C and absorbed on
~5 parts by weight of synthetic silicic acid (mix~ure 1~.
Separately, a mixture is prepared from
39.0 parts by weight of compound C
29 13.0 parts by weight of sodium--lignin-su~fonate
_ 7 --
HOE 7 _' 315
2~
3u0 parts by weight of sodium dibutylnaphthalenesulfonate
2.0 parts by weight of partially saponified polyvinyl acetate
1.0 part by weight of polypropylene glycol and
16.6 parts by weight of synthetic silicic acid
and finely ground on a pin mill (mixture 2).
Mixture 1 and mixture 2 are then blended and ground again on
a slowly rotating cross beater mill to give a wettable powder
ready for use.
Ratio of C to I = 3.25:1.
FORMULATION EXAMPI,E 6:
. .
As described in Example 5, two mixtures are prepared se-
parately and then ground together to give a wettable powder
Mixture 1
18.0 parts by weight of compound II as methyl ester
15.0 parts by weight of synthetic silicic acid
Mixture ?
35.0 parts by weight of compound C
14.0 parts by weight of sodium lignin-sulfonate
3.2 parts by weight of sodium oleyl N-methyltauride
1.0 part by weight of sodium palmitate
11.0 parts by we--ght of synthetic silicic acid.
Ratio of C to II = 1,94:1.
FORMULATION EXAMPLE 7:
In the manner described in Example 5, two mixtures are
prepared separately and then ground together to give a wettable
powder.
Mixture 1
15.7 Parts by weight of the methyl ester of compound ITI
29 12~3 parts by weight of synthetic silicic acid
~ ~ 9~ ~ HOE 76/E 315
, .
Mixture 2
36.4 Parts by weight of compouncl C
14.6 parts by weight of sodium lignin-sulfonate
2.0 parts by weight of dioctylsulfosuccinic acid ester in .
the form of its sodium salt
2.0 parts by weight of sodium oleyl-N-methyltauride
5.0 parts by weight of sodium 'bicarbonate and
10.0 parts by weight of synthetic silicic acid.
Ratio of C to III = 2.4:1.
FORMULATION ~XAMPLE 8:
8.0 Parts by weight of the isobutyl ester of compound I are
liquefied at 60 C and absorbed on
5.7 parts by weight of synthetic silici.c acid (mixture 1)~
Separately,
41.5 parts by ~eight of compound D
14.0 parts by weight of sodium lignin-sulfonate
4.0 parts by weight of sodium dibutylnaphthalenesulfonate
1.0 part by weight of sodium dodecylbenzenesulfonate and
20.8 parts by weight of di~tomaceous earth
are mixed and finely ground on a pin mill (mixture 2~.
Then, mlxtures 1 and 2 are blended and ground once on a slow-
ly rotating cross beater mill to give a wettable powder ready
for use~
Ratio of D to I = 5.19:1
FORMULATION EXAI~PLES 9 to 12:
In similar manneX formulations can be pxe~ared f~om the
constituents indicated in the following table.
,
--
.
HOE 76/F' 315
~ a) ll
H H.,
H o ~ ~r o u~ o o H
_~ Irl N ~ O 0 ~7 CD
. a N
~;;:! ~
rl
k
H 3 . Il
H H ..
H ~ O ~ Ltl O O O lil 1~H- ~n
_~ ~ ~n ~ o oo~ r ~
~- ~r ~ ~ ~ u~
r~
11
H O O O O O O O H ~r
oc~ r
~ '- ~ ~') ~ C:l ~
,i a) o u~ o o o o ~ m
I I 1 11: H N
H ~1 c0 ~01 io ~ 00
~ ~ ~ ~ ~ a ~
o~ ~
,,, a)
t,
o
. ~
~a~ ~ o
;rl ~ ~ ~ ~r~
U~ r~
~ o
.c fd .~
~a
.~ ~ o 5
O E ~ ~ .;~
a) Q,
. ,~ S E ~
~ ~ ~ I Z ~ O -i
D~ ' O ~
Q~ ~ a) E u~ u~
E3 ~ Q X ~ .~
Q) ~_ O ~ ~ ~ 1 r~ O r~ ~ C)
~ c~ ,1 ~ ~a ,~ o ~
~ ~ ~ ~ a) ~
a: .~ ~ ~ ~ o ~ o
U~ ~) ~rl ~ ~) ~1~ r~ r~ ~1 r~
~c ~ ~ x ~ a ~a ~c ~ c
o ~, ~ r~ o o o o o o o o
E~ t~ ~ ~ t~
.
HOE 76/F 315
.3L~9~
BIOLOGIC~L EX~PLES:
.
E X A M P L E 1:
Plants of annuaL blackgrass and sugar beet were grown
in pots in the greenhouse and treated, in the three to four
leaf stage with aqueous emulsions of compound I as isobutyl
ester and compound A, respectively, and with compositions of
the said components in different proportions~ The result 4
weeks after treatment is indicated in the following Table 1.
It can be seen that compound I alone had a good effect on an-
nual blackgrass, whereas compound A did not show any effec-t.
With the composition~ the effect on annual blackgrass was
surprisingly much higher, above all with doses of A + I of
1.0 ~- 0.1~ and 1.0 + 0.06 kg per hectare. Sugar beet was not
damaged.
T A B L E
Effect in post-emergence trial (greenhouse test)
treated with dose effect (~ damage1 on
kg/ha blackgrass sugar beet
.. .. _ _ _ . _ _ _ _ _
A 1.0 0 0
I (as isobutyl ester~ 0~5 100 0
0.25 97,5
0~12 85
0.06 65
A + ~ i.0 + 0~5 100 0
140 + 0.25 100
1.0 + 0.12 97.5
1~0 + 0~06 75
_OE 76/F 315
f~
E X A M P L E 2:
In a similar test, active compoundsII and A alone and
in combination were examined as to their effect on wild oat
and sugar beet.
In this case, too, the composition showed a drastical
and unexpected increase in the effect on wild oat.
T A B L E 2
Effect of herbicidal combinations in a post-emergence
trial (greenhouse test~
treated with flose effect (% damaqe) on
(kg/ha) Wild oatsugar beet
A 1~0 0 0
II (as ethyl ester~ 1.0 98.7 0
0.5 97.5
0.25 80
0.12 65~6
0.06 4.1
A + II 1.0 -~ 1,0 100 0
1.0 + 0.5 99.5
1,0 + 0.2S 95
1.0 + 0.12 92.5
1.0 + 0.06 76.2
E X A M P L E 3
In an open air trial in a field infested wi:th various
types of weeds the active compounds of the preceeding example
were spraved after emergence indlvidually and in combination,
partly as a tank mixture and part1y~as ~ormulated we1table
powder. The result, 5 weeks after the treatment, as indicated
- 12 ~
HOE 76/}_3l5
in the ollowing Ta~le 3 shows that
A alone was e,fecti~ve only agai~nst dicoty1~edonous weeds
(curled blackgrass and chickweed~
II alone was ef~ective exclusive'ly against wi;ld oat
The combinations of A + II ~lad a disti.nctly better e~fect
on wild oat than compound II alone, especially with a dose of
0.72 kg/ha of compound II.
In all trials sugar beet was left unharmed.
. T A B L E 3
- 10 Effect of herbicidal combinations in a post-emergence trial
(~ield test~
treated with dose effe~t (~ damage~ on
(kg/ha~ wild oat curled black- chickweed sugar beei
grass
A O . 9~ 0 95 100 0
II(as methyl ester~ 0.9 92. 5 0 0 0
0.72 75 0 0 0
A t- II 0.94-+ 0~9 97~5 97.5 100 0
0.94 + 0.72 95.0 95 100 0
**
A + II 0.94 l 0~9 98.75 97~5 100 0
0O75 + 0.72 96.25 92.5 100 0
*
as tank mixture
**
- . as wettable powder formulated according to Formulation
: Example 1~
E X A M P L E 4:
. . .
In a manner analogous to that described in Example 2,
compounds III, A and B alone and combinations of A + III and
B + III were sprayed on wild oat and sugar beet. In ihis case,
too, the combinations had a distinctly better effect on the wild
.
- 13 -
~ HOE 76/E~' 315
oat than the individual compounds.
T A B L E 4
~ . = = .. . .
Effect of herbicidal combinations in a pos-t-emergence
trial (greenhouse test~
treated with dose effect (% damage~ on
(kg/ha) wild oatsugar beet
A 0.94 0 0
B 0.94 0 0
III 0~72 98.7 0
0.36 90
0.18 75
0.09 32.5
A ~ III 0.94 + 0.72 100 0
0.94 + 0.36 99.2
0.94 + 0.18 90
0.g4 + 0.09 80
B + III 0~94 ~ 0.72 ~00 0
0.9~ + 0.36 9~.2
0.94 + 0.18 97.5
0.94 ~ 0.09 85
- E X A M P L E 5-
_
In a trial in pots under natural climatic conditions the
compounds as used in the preceding example were sprayed on
wild oat and annual blackgrass individually and in combination.
This test confirmed the synergistic effect of the combinations
on wild oat. The effect on annual blackgrass was likewise in-
creased distinctly as compared to the exclusive ùse of compound
III although compounds ~ and B were ineffective.
- 14 -
~ 6 HOE 76/F 315
T A B L E 5
Effect of herbicidal combina-tions in a post-emergence
trial (vegetation hall)
treated with dose effect (~ damage) on
(kg/ha) wil.d oat annual blackgrass
.. . . . _ _
A 0.94 0 0
B 0.94 0 0
III 0.72 92.5 85
0~54 67~5 65
A + III 0.94 + 0.72 99.4 92.5
0~70 ~ 0,54 87~5 85
B + III 0.94 ~ 0.72 97.5 93.7
0.70 + 0.54 90~0 92.5
as tank mixture
**
as wettable powder formulated according to Formulation
Example 3.
E X A M P L E 6-
In a greenhouse test compounds A, B and IV alone and
combinations of A ~ IV and B + IV were sprayed after emergence
on the weed grasses wild oat and annual blackgrass and the crop
plant sugar beet. The combinations were diluted in dilution
series in a constant mixing ratio of 1. 74 to 1
- The results indicated in Table 6 confirm that the combina~
tions had a distinctly better e~ect on the weed grasses than
compound IV alone although compounds A and B wnen applied in-
dividually, were ineffective on gxasSes.
~ 15 ~
IIOE 7 6 /E' 3 15
T A B L E 6
Effect of herbicidal combinations in a post-emergence
trial in the greenhouse
treated with dose effect (% damage~ on
. (kg/ha) wild annual black~ sugar beet
- oat grass
. _ _ _ . . .. . _ _ _ . _ . _ _ _
B 0.470 0 0 0
A 0.470 0 0 0
.- IV(as methyl : 0.270 100 100 0
- ester)
0.135 88.3 98~8 0
0.067 48.5 92.5 0
0.034 16.1 70 0
-B + IV 0.~70 + 0.270 100 100 0
0.235 + 0.135 100 100 0
0.117 + 0.067 80 100 0
0.059 + 0~034 77.5 97.8
A + IV 0.470 + 0.270 100 100 0
0.235 + 0.135 100 100 0
0.117 + 0.067 89.5 98.3 0
0.059 + 0.034 48.8 91.3 0
E X A M P L E 7:
In a field infested with couch grass various plots were
treated, after emergence of sugar beet, with compounds B and
IV individually and with combinations thereof according to
the invention. The results in Table 7 show that 4 weeks after
the treatment the combinations had a bet-ter effect against
couch grass than compound IV alone although compound B alone
was absolutely ineffective. 10 Weeks after the treatment, the
. - 16 - -
~ 2~ HOE 76/~ 31~
differences were still distinctly perceptible. In the plots
treated with compound IV the effect had a little ~ubsided,
while in the areas treated with combinations of B with IV the
effect was even more pronounced.
T A B L E 7
Effect of herbicidal combinations in a post-emergence
trial (field test)
treated with dose effect (% damage) on
(kg/ha) couch grass sugar beet
4* 10* 4* 10*
B 0.94 0 0 0 0
IV 1.80 90 85 0 0
1.44 87.5 77.5 0 0
B + IV0.94 + 1.80 97.5 99 0 0
0.94 ~ 1.44 95 97.5 0 0
- * weeks after treatment
E X A M P L E 8:
Seeds of barley, wheat and several weed grasses were
sown in pots and placed in the greenhouse. After the develop-
ment of about 3 leaves, the plants were sprayed with compounds
C and I, respectively, and with mixtures thereof.
The result 4 weeks after treatment is indicated in the
following Table 8. The figures show that 0.62 ~g/ha of com-
pound C alone had an unsatisfactory effect against 2 of the
three types of weeds used, but that in combination together
with 0.31 kg/ha of compound I the effect was almost complete
against all weeds although compound I was effective against
annual blackgrass only. Surprisingly, the effec-t of the
combination against bent and cleaver was better than expected.
- 17 -
~IOE 76/F 315
The combination of 1.25 kq per hectare of C ~ 0.31 kg
per hectare of I also showed an increased effect, but with the
effect of C alone being already so good, a synergism could
not be clearly ascertained.
The mixing ratio of C to I ~as 4:1 and 2:1, respectively.
T A B L E 8
Effect of herbicidal combinations in the post-emergence
trial (greenhouse test~ in % of damage with doses ~n kgJha
types of plants C I C 0.62
0.62 0.31~ I 0.31
_~
a~ weeds
bent 90 0 100
cleaver 75 0 95
blackgrass 32,S 85 95
b) crop plants
wheat 0 0 0
barley 0 0 0
E X A M P L E 9:
In a greerhouse test compounds C, II and III were sprayed
alone and in form of the combinations C + II and C + III on 4
types ol weeds and on barley and wheat. In the combinations the
ratio of the active compound was 1.91;1 and 2.44:~, respecti-
vely. The combinations exhibited an unexpectedly distinct in-
crease in the effect against all types of weeds.
- 1B -
.
.....
~ MOE 76/F 315
T A B L E 9
Effect of herbicidal combinations in a post-emergence
trial in the greenhouse in ~ of damage
compound dose wild black bent barnyard barley
(kg/ha) oat grass grass wheat
.
C0.44 38 48.5 92.5 90 0
0.22 0 8 32 51 0
II0.23 91 70 0 0 0
0.11 90 16 0 0 0
III 0.1B 92.5 90 16 0 0
0.08 82.5 82.5 0 0 0
C + II 0.44 + 0.23 99.5 100 99.5 97.5 0
0.22 -~ 0.11 97O5 75 80 75 0
C + III 0.44 + 0.18 100 99.5 97.5 98O7 0
0.22 + 0.09 95 go 9Q go 0
E X A M P L E 10:
Seeds of annual blackgrass (Alopecurus myosuroides) were
sown in pots and after emergence in the 2 to 3-leaf stage the
plants were treated in the greenhouse with compounds D and I
alone and with combinations thereof in a mixing proportion of
D to I of 5.19:1 and 3.25 1, respectively.
The result of the treatment, expressed as percentage of
damage 4 weeks after the treatment, is indicated in Table 10.
It can be seen that With the combinations, above all in low~.
doses, the effect against annual blackgrass was unexpected in-
creased as compared ~ith the effect obtained with the individual
compounds. In no case ~heat ~a~ damaged (not indicated in the
table~.
- 19 - -
HOE 76/F 315
T A B L E 10
Ratio of D:I = 5.19:1 Ratio of D:I = 3.25:1
active dose ~ffect active dose effect
compound (kg/ha) compound (kg/ha)
.. . . _ . . . .. _ ... . ... _ . _ .
I 0.270 95 I 0.270 9S
0.135 75 0.135 75
0.067 32 ~.067 32
0.034 16 0.034 16
D 1.4 80 D 0.875 70
0.7 65 0.437 48.5
0.35 32 0.219 0
0.175 0 0.109 0
I + D 0.270 -~ 1.4100 I + D 0.270 + 0.875 99
0.135 + 0.790 0.135 + 0.43795
0.067 + 0.35 85 0.067 + 0.219 70
0.034 + 0.175 65 0.024 -~ 0.109 60
E X A M P L E 11:
In a further test in the greenhouse ac-tive compounds D,
II ana III were applied alone and in combinations of D + II
and D + III after emergency of the plants. In the combina-
tions the ratios were as follows:
D + II = 1.75 + 0.9 kg/ha, corresponding to 1.94:1
D + III = 1.75 + 0.72 kg/ha, corresponding to 2.43:1~
At the ti~.e of treatment the weed grasses, annual black-
grass and bent, had approximately 3 leaves while the crop plants,
spring wheat and spring barley, had developed 3 to 4 leaves.
The results indicaied in Table 11 show that compound D
had a weak effect on annual blackgrass and a good effect on bent,
~3~ MoF 76/~l 315
while compounds II and IIII both used as methyl ester, had arelatively good effec-t on blackgrass but not on bent.
The combinations are charac-terized by an unexpectedly high
effect on blackgrass and on bent. Wheat and barley
were damaged only with the highest doses, the damage was slmi-
lar to that caused by compound D alone.
T A B L E 11
Effect of herbicidal combinations in a post emeryence
trial (greenhousel.
effect (% damagel on
active dose black- bent wheat barley
compound (kg/ha] grass
.
D 0~88 62 96 7~5 10
0~44 8 48~5 0 1 r2
0~22 0 8 0
II 0~45 87~5 0 0 0
0~ 23 70 0 0
0~11 16~2 0 0 0
III 0. 36 92 ~ 5 32 ~ 5 0 0
OJ ~8 87~5 16~2 0 0
0~ 09 75 0 0
D + II 0~88 + o~a5 95 97~5 10 12~5
~44 + 0~23 87~5 85 -2~5 2~5
0~22 ~- 0~11 48~5 32~5 0 0
D + III 0~88 + 0~36 100 97~5 7~5 10
- 0~44 + 0.18 97~5 90 n 1 ~2
0~ 22 + ~ 09 90 32 ~ 5 0 0
~ 21 ~
HOE 76/E 315
~9~6
E X A M P L ~_ 12:
In a field test in sugar beet infested with wild oat and
some types of dico-tyledonous weeds active compounds E, III and
IV alone and combina-tions of E + III and E ~ IV were sprayed
after emergence of the beet plants. E showed no effect against
wild oat and had a weak effect only on dicotyledonous weeds.
The effect of III and IV on wild oat was also relatively weak.
Surprisingly, with the combinations the effect on wild oat and
on the dicotyledonous weeds common orache, Wild mustard and
knotgrass increased beyond the expected degree.
T A B L E 12
Effect of herbicidal combinations in a post-emergence
trial (field test)
effect (% damage~ on
active - dose wild cornmon wild knot- sugar
compound (kg/ha~ oat orache mustard grass beet
-
E 4~9 0 30 57.532e5
III 0~72 62 0 0 0 0
IV 0~36 43 0 0 0 0
Q~54 60 0 16 0 0
E 1 III 4.9 + 0.72 97.5 60 75 5n 0
E + IV 4~9 + 0~36 82~5 57.5 70 45 0
+ 0.54 92.5 60 72.5 55 0
- 22 -
