Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
85~1
Case 5-12947/=
Synergistic composition and method of selectively
controlling weeds, especially in crops of sugar
beet and fodder beet
._
The present invention relates to a synergistic
composition comprising a combination of herbicides and
which is most suitable for selec~ively controlling weeds,
especially in crops of sugar beet and fodder beet. The
invention also relates to a method of controlling weeds
which comprises the use of the novel composition, especially
in crops of sugar beet and fodder beet.
The most frequently encountered and most important
weeds in crops of sugar beet and fodder beet at the present
time are species of the genera Amaranthus (foxtail),
Chenopodium (goosefoot), Sinapis (mustard), Panicum (panic
grass) and certain Avena species (wild oats).
Excellent postemergence selective herbicides
against monocot weeds are 4-(3',5'-dichloropyridyl-2'-oxy)-
~-phenoxypropionic acid propargyl esters of the formula I
~Cl ca3
Cl~ --o~ O-CH-CO-Z-CH2-C-
.. ...
wherein 7 is oxygen or sulfur.
~ 3 7~85
-- 2 --
The two compounds of formula I, viz. 4-(3',5'-
dichloropyridyl-2'-oxy)-~-phenoxypropionic acid propargyl
ester (Ia) and 4-(3',5'-dichloropyridyl-2'-oxy)-~-phenoxy-
thiopropionic acid propargyl ester (Ib), processes for the
production thereof and the use thereof as selective
herbicides, are described in European patent publication
3114.
Dicot weeds are often successfully controlled
postemergence with 4-amino-3-methyl-6-phenyl[4H]-1,2,4-
triazin-5-one (Metamitron) of the formula IIa
~ ~ -C~ (IIa)
or with methyl-3-m-tolylcarbamoyloxyphenylcarbamate
(Phenmedipham) of the formula IIb
-O~C~N~~t~ il-o-C-NH~ CH3 (IIb)
Metamitron and its herbicidal activity were
described e.g. at the 3rd Int. Meeting of Selective Weed
Control in Beet Crops, Paris, 1975. Phenmedipham and its
herbicidal properties are reported on e.g. in Abstr. 6th
Int. Congr. Pl. Prot., Vienna, 1967, page 433.
Surprisingly, it has now been found that a
combination of the two compounds of the formulae I and II,
in a ratio varying within specific limits, exerts a
synergistic action which is able to control the majority
of all important weeds in crops of sugar beet and fodder
beet without damaging these crops. The principal weeds in
i ~ 7~85'1
these crops, such as species of the dicot Amaranthus, Chenopodium
and Sinapis varieties, as well as the monocot Panicum and Avena
varieties, are selectively destroyed in the emergent beet crops.
Accordingly, the invention provides a synergistic
composition for selectively controlling weeds, which composition
comprises, on the one hand, a 4-(3',5'-dichloropyridyl-2'-oxy)-~-
phenoxypropionic acid propargyl ester of the formula I
Cl CH3 (I)
Cl~ o ~ O-CH-CO-Z-CH2-C -CH ,
wherein Z is oxygen or sulfur, and, on the other, 4-amino-3-
methyl-6-phenyl~[4H]-1,2,4-triazin-5-one (IIa) or methyl-3-m-
tolylcarbamoyloxyphenylcarbamate (IIb), together with carriers
and/or other adjuvants, the amount of component (II) being
approximately ecIual to, or in excess of, component (I~.
It is surprising that the combination of a compound of
the formula I with a compound of the formula II not only brings
about an expected aclditive enhancement of the activity spectrum
against the customary weeds associated with sugar beet and fodder
beet, but gives rise to a synergistic effect which potentiates
the action of both components from two points of view.
On the one hand, the rates of application of the single
compounds I and II are distinctly reduced while the same good
action is retained. On the other hand, the combination also
achieves a high degree of weed control where both single compounds
.~ r~
~3--
117~
have become totally ineffective at too low rates of application.
The consequence is a substantial broadening of the activity spectrum
against weeds and an additional increase in the safety margin on
application to crops of sugar beet, as is necessary and desirable
in the event of unintentional overapplication.
The composition of this invention can also be used for
selectively controlling weeds in crops of other dicot plants having
similar sensitivity to herbicides and similar weed in~estation.
The herbicidal combination employed in the practice of
this invention will preferably contain a compound of the formula
(I~ and a compound of the formula (II) in a ratio of 1:1 to 1:4,
most preferably 1:1 to 1:2.
~,_
-3a-
~7~85'
-- 4 --
The herbicidal combination has an excellent action
against weeds without having any noticeable effects in
crops of sugar beet and fodder beet when used in the
conventional rates of application o 0.2 to 4 kg/ha,
preferably 0.5 to 3 kg/ha.
The present invention also relates to the use of
the composition, i.e. to a method of selectively controlling
grasses and weeds postemergence in beet crops.
In addition to the novel combination of active
ingredients, the composition of this invention also contains
suitable carriers and/or other adjuvants. These can be solid
or liquid and correspond to the substances conventionally
employed in the art of formulation, e.g. natural or
regenerated mineral substances, solvents, dispersants a
wetting agents, tackifiers, thickerners, binders or
fertilisers. Suitable formulations are therefore e.g.
emulsifiable concentrates, directly sprayable or dilutable
solutions, dilute emulsions, wettable powders, soluble
powders, dusts, granula~es, and also encapsulations in e.g.
polymer substances. The methods of application, such as
spraying, atomising, dusting, scattering or pouring, are
chosen in accordance with the intended objectives and the
prevailing circumstances, just like the nature of the
compositions.
The formulations, i.e. the compositions or
preparations containing the herbicidal combination
of the invention and, where appropriate, a solid or liquid
adjuvant~ are prepared ~n known manner, eOg. by homogeneously
mixing and/or grinding the active ingredients wi~h
ex~enders, e.g. solven~s, solid carriers and, where
appropriate, surface-active compounds (surfactants).
i97~5
-- 5 --
Suitable solvents are: aromatic hydrocarbons,
pre~erably ~he fractions containing 8 to 12 car~on
atoms, e~g. xylene mixtures or substituted naphthalenes,
phthalates such as dibutyl phthalate or dioctyl phthalate,
aliphatic hydrocarbons such as cyclohexane or paraffins,
alcohols and glycols and their ethers and esters, such as
ethanol, Pthylene glycol, ethylene glycol monomethyl or
monoethyl ether, ketcnes such as cyclohexanone, strongly
polar solvents such as N-m~thyl-2-pyrrolidone, dimethyl
sulfoxide or dime~hyl formamide, as well as epoxidised
vegetable oils such as epoxidised coconut oil or soybean
oil; or water.
The solid carriers used e.g. for dusts and
dispersible powders are normally natural mineral fillers
such as calcite, talcum, kaolin, montmorillonite or
attapulgite. In order to improve the physical properties
it is also possible to add highly dispersed silicic acid
or highly dispersed absorbent polymers. Suitable granulated
adsorptive carriers are po~ous types, for example pumice,
broken brick, sepiolite or bentonite; and suitable
nonsorbent carriers are materials such as calcite or sand.
In addition, a great number of pregranulated materials of
inorgar.ic or organlc nature can be used, e.g. especially
dolimite or pulverised plant residues.
Suitable surface-active compounds are
nonionic, cationic and/or anionic surfactants having good
emulsifying, disper~ing and wetting properties. The term
llsurfactants" will also be understood as comprising
mixtures of surfactants.
i~7~8
-- 6 --
Suitable anionic surfactants can be both water-
soluble soaps and water-soluble syn~he~ic surface-active
compounds .
Suitable soaps are the alkali metal salts, alkaline
earth metal salts or unsubstituted or substituted ammonium
salts of higher fatty acids (C10-C2z), e.g. the sodium or
potassium salts of oLeic or stearic acid, or of natural
fatty acid mixtures which can be obtained e.g. from coconut
oil or tallow oil. Mention may also be made of fatty acid
methyltaurin salts.
More frequently, however~ so-called synthetic
surfactants are u~ed, especially fatty sulfonates, fatty
sulfates, sulfonated benzimidazole derivatives or alkyl-
arylsulfonates.
The fatty sulfonates or sulfates are usually in the
form of alkali metal salts, alkaline earth metal salts or
unsubstituted or substituted ammonium salts and contain a
C~-C22alkyl radical which also includes the alkyl moiety of
acyl radicals, e.g. the sodium or calcium salt of ligno-
sulfonic acid, of dodecylsulfate or of a mixture of fa~ty
alcohol sulfates obtained ~rom natural fatty acid~. These
compounds also comprise the salts of sulfuric acid e~ters
and sulfonic acids of adducts of fatty alcohols and ethylene
oxide. The ~ulfonated benzimids~Qle derivatives preferably
contain 2 sulfonic acid groups and one fatty acid radical
containing 8 to 22 carbon atoms. Examples of alkylarylsulf-
onates are the sodium, calcium or triethanolamlne salts of
docecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid,
or of a naphthalenesulfonic acid/formaldehyde condensation
product. Also suitable are corresponding phosphates, e.g.
I ~ 7~8S'l
-- 7 --
salts of the phosphoric acid ester of an adduct of
p-nonylphenol with 4 to 14 moles of ethylene oxide.
~ on-ionic surfactants are preferably polyglycol
ether deriva~ives of aliphatic or cycloaliphatic alcohols,
or saturated or unsat~rated fatty acids and alkylphenols,
said derivati~es containing 3 to 30 glycol ether groups
and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon
moiety and 6 to 18 carbon atoms in the alkyl moiety of the
alkylphenols.
Further suitable non-ionic surfactants are the
water-soluble adducts of polyethylene oxide with poly-
propylene glycol, ethylenediaminepolypropylene glycol and
alkylpolypropylene glycol containing 1 to 10 carbon atoms
in the alkyl chain, which adducts contain 20 to 250 ethylene
glycol ether group~ and 10 to 100 propylene glycol ether
groups. These compounds usually co~tain 1 to 5 ethylene
glycol units per propylene glycol unit.
Representative examples of non-ionic surfactants
are nonylphenol-polyethoxyethanol~, castor oil polyglycol
ethers, polypropylene/polyethylene oxide adducts, tributyl-
phenoxypolyethoxyethanol, polyethylene glycol and octyl-
phenoxypolyethoxyethanol. Patty acid esters of polyoxy-
ethylene sorbitan and polyoxyethylene sorbitan trioleate
are also suitable non-ionic surfactants.
Cationic surfactants are preferably quaternary
ammonium salts which contain, as N-substituent, at least
one polyglycol ether or C8-C22alkyl radical and, as further
substituents, lower unsubstituted or halogenated alkyl,
benzyl or lower hydroxyalkyl radicals. The salts are
preferably in the form of halides, methylsulfates or
7~85.,i
- 8
ethylsulfates, e.g. stearyltrimethylammonium chloride or
benzyldi(2-chloroethyl)ethylammonium bromide.
The surfactants customarily employed in the art
of formulation are described e.g. in the following
publications: "McCutcheon's Detergents and Emulsifiers
Annual", MC Publishing Corp., Ringwood, New Jersey, 1979;
Sisely and Wood, "Encyclopedia of Surface Active Agents",
Chemical Publishing Co. Inc., New York~ 1964.
The concentration of active ingredient in commercial
composi~ions is from 0.1 to 95% by weight, preferably from
1 to 80% by weight.
Preferred formulations are composed in particular
of the following constituents (% = percentage by weight):
Solutions
active ingredient: 5 to 95%, preferably 10 to 80%
solvent: 95 to 5%, preferably 90 to 0%
surfactant: 1 to 30%, preferably 2 to 20%
Emulsifiable concentrates
.
active ingredient:10% to 50%, preferably 10 to 40%
solvent:5% to 30%, preferably 10 to 20%
liquid carrier:20% to 95%, preferably 40 to 80%
Dusts
active ingredient:0,5 to 10%, preferably ? to 8%
solid carrier:99.5 to 90%, preferably 98 to 2%
1 3 ~8~.1
SusPension concentrates
active ingredient: 5 to 75~, preferably 10 to 50%
water: 94 to 25%, preferably 90 to 30%
surfactant: 1 to 40%, preferably 2 to 30%
Wettable powders
active ingredient: 5 to 90%, preferably 10 to 80% and,
most preferably, 20 to 60%
surfactant: 0.~ to 20%, preferably 1 ~o 15%
solid carrier: 5 to 90%, preferably 30 to 70%
Granula~es
.
active ingredient: 0.5 to 30%, preferably 3 to 15%
solid carrier: 99.5 ~o 70%, preferably 97 ~o 85%.
Whereas commercial products will be preferably
formulated as concentrates, the end user will normally
employ dilute formNlatîons. The formNlations can be diluted
to a concentration as low as 0.001%.
The compositions of the invention can be mi~ed
with other biocidal compounds or composi~ions. Accordingly,
in addition to containing the compounds of the general
formula I and of the formula II, the compositions of the
invention can also contain e.g. insecticides, fungicides,
bactericidesg fungistats, bacteriostats, or nematocides,
in order to broaden the activity spectrum.
Herbicide~ always have a synergistic effect if the
herbicidal action of the combination o I + II is greater
than the sum o the action of the individual ac~ive
i~gredients.
)37~85~
- 10 -
The expected plant growth E for a given combination
of two herbicides can be calculated as follows ~c. COLBY,
S.R., "Calcuïating synergistic and antagonistic responses
of herbicide composition~'i, Weeds 15, pages 20-22 1967):
Y
. _
100
wherein
X - the percentage growth (compared with untreated plants)
after treatment with a herbicide I a~ a rate of
application of p kg per hectare,
Y ~ the percentage growth after treatment with a her~icide
II at a rate of application of q kg per hectare, and
E - the expected percentage growth (compared with the
control plants) after treatment with the herbicidal
mixture of I + II at a rate of application of p ~ q kg
of active ingredient per hectare.
If the actually observed value i9 lower than the
expected vaLue E" then there i8 gynergism.
The synergistic effect of the combination of
compounds I and II is demonstrated in the first of the
following Examples.
~7~85~1
- 11 -
Example 1:
The test plants are sown, in a greenhouse, in plastic
containers filled with 30 litres of sterilised garden soil.
The p;ants are then sprayed postemergence in the 2- to
3-leaf stage with an aqueous dispersion of the combination
of herbicides. The rate of application of the dispersion
is 50 ml/m2. Evaluation is made after 15 days at 17-23C
and a relative humidity of 60-70%, and daily watering of
the containers. The degree of damage to the plants is
assessed linearly in accordance with the following rating:
1 - plants withered
5 - medium damage
9 - normal state.
The following results are obtained with different mixture
ratios and total amounts of active ingredient:
) Table 1: Tolerance and activity of 4-(3',5'-dichloro-
pyridyl-2'-oxy)-~-phenoxypropionic acid
propargyl ester (compound Ia) and Metamitron
(compound IIa), and mixtures thereof, when
applied post-emergence:
. ~
Metamitron (compound IIa)
kg a.i./ha 1.0 0.5 0.25 0
~ ., . u~ ~ _ u~ ~
compound Ia kg a.i./ha - o o o o o o o o ~ o
. . __ . _
sugar beet 'Kawemono' 9 9 9 9 9 9 9 9 9 9
fodder beet 'Corona' 9 9 9 9 9 9 9 9 9 9
Panicum crus-galli 9 1 1 9 1 1 9 1 1
Avena fatua 2 1 1 9 1 1 9 1 1
Amaranthus retroflexus 2 1 1 6 1 1 9 3 9 9
Chenopodium album 6 1 1 9 2 2 9 3 9 9
Sinapis arve~sis 9 4 3 _ 9 9 . .
l~7~85
- 12 -
If the values relating to the additive action calculated
by the method of Colby are compared with the results
reported in Table l, then it is evident that the observed
growth figures given for Amaranthus retr., Chenopodium
alb. and Sinapis arvenis are lower than those calculated.
The synergistic effect of the combination of 4-(3',5'-
dichloropyridyl-2'-oxy)-~-phenoxy)-~-phenoxypropionic acid
propargyl ester and Metamitron is thus demonstrated
(cf. Table 2).
able 2: Values calculated by the method of Colby for
demonstrating the synergism of 4-~3',5'-
dichloropyridyl-2'-oxy)-~-phenoxypropionic
acid propargyl ester (compound Ia) and
Metamitron (compound IIa).
, ... . . . .
P~ a ~ /ha l.o 0.5 0.25
~ -~ ..... _. .~ .. ____
compound Ia o. 5 0.25 0.5 0.25 0.25
~ . . / _ . _ _ _
.,~ ~ .,~ a~ .,1 a) ,-~ aJ .,
~ J~ e J e
~ a) u ~ ~ a) u ~ ~ U a1 ~ ~ U ~ ~ C~ U
aJ ~ ~ ~ ~ ~ ~ a
~1 ~_I J- ~ ~4~ JJ ~ p~ ~ ~ p~
a) ~ ~ a) ~ X ~ a) ~ a~
. . _ ... ... . . __ .
sugar beet
'~a~emono' 100 100 100 100 100 100 100 100 100 100
fodder beet
'Corona' 100 100 100 100 100 100 100 100 100 100
Panicum c.g. 1 1 1 1 1 1 1 1
Avena fatua 1 1 1 1 1 1 1 1
A~aranthus retr. 1 12 1 12 1 62 1 62 25 100
Chenopodium alb. 1 62 1 62 12 100 12 100 25 100
Sinapis arvensis37 100 25 100 100 100 100 100 100 100
_ . . .~
0~5'
- 13 -
) Table 3: Tolerance and activity of 4-(3',5'-dichloro-
pyridyl-2'-oxy)-~-phenoxypropionic acid propargyl
ester (compound Ia) and Phenmedipham (compound
IIb) and mixtures thereof, when applied post-
emergence:
Phenmediph~ ~c~pound Ilb)
kg a.i./ha `` l.0 0.5 0.25 o
. ~ . ~ _ .
compound Ia kg a.i./ha -o o o o o o o o o o
. . _
sugar beet 'Kawemono' 9 9 9 9 9 9 9 9 9 9
fodder beet 'Corona' 9 ~ 9 9 9 9 9 9 9 9
Panicum crus-galli 2 1 1 3 1 1 8 1 1 1
Avena fatua 9 l l 9 l l 9 l l l
Amara~thu~ retrofle~us 9 6 6 9 7 3 9 9 9 9
Che~opodium album 3 3 ~ 4 ~ 3 9 3 9 9
Sinapi8 arven~i~ 2 2 1 7 2 4 9 7 9 9
If the values relating to the additive action calculated
by the method of Colby are compared with the results
reported in Table 3, then it is evident that the observed
growth figures given for Amaranthus retr., Chenopodium
alb. and Sinapis arvensis are lower than those calculated.
The synergistic effect of the combination of 4-(3',5'-
dichloropyridyl-2'-oxy)-~-phenoxypropionic acid
propargyl ester and Phenmedipham is thus demonstrated
(cf. Table 4).
able 4: Values calculated by the method of Colby for
demonstrating the synergism of 4-(3',5'-
dichloropyridyl-2'-oxy)-~-phenoxypropionic acid
propargyl ester (compound Ia~ and Phenmedipham
(compound IIb).
Ig~85'~
- 14 -
.. . _ .. . . _ . . ,
Cok~poaui~/hlb ¦ l.o 0.5 0.2;
compound Ia 1 0.5 0.25 0.5 0.25 0.25
k~ a.i./ha
. . . .
.~ ~ .~ ~ ,~ ~ .5 ~ .
E~ ~ ~ ~ ~ u
u ~ ~ a) ~ a~ u ~ s~ a~ U a
~ ~ ~ ~ ~ ~ ~ ~ 3
J ~ Q~ J ~ ~ ~ ~1 P~
a) ~ ~ ~ ~ ~ ~ * ~ ~ a~ cd X
;~
. . , . ..
sugar beet
'Kaweno' 100 100 100100 100 lOolOo 100 100 100
fodder beet
'Corona' 100100100 100 100100 100 100 100 100
Panicu~ c.g. 1 1 1 1 1 1 1 1
Avena fatua 1 1 1 1 1 1 1 1
~maranthus retr. 62100 62 100 75 100 100 100 100 100
Chenopodium alb. 2S 25 12. 25 25 37 25 37 25 100
Sinapi~ ar~7ensis 12-~12 1 12 12 75 37. 75 t5 100
) TabLe 5: Tolerance and activity of 4-(3',5'-dichloro-
pyridyl-2'-oxy)-~-phenoxythiopropionic acid
propargyl ester (compound Ib) and Metamitron
(compound IIa) and mixtures thereo~, when
applied postemergence.
~etam~n (comp.~a~kg a.iiha _ 0.5 0.25 O
.... _~ u~ ~ . ~ ~ ~
compound Ib kg a.i./ha o o o o o o o o o o
_ ._ _ ~
sugar beet 'Kawemono' 9 9 9 9 9 9 9 9 9 g
fodder beet 'Corona' 9 9 9 9 9 9 9 9 9 9
Panicum crus-galli 9 1 1 9 1 1 9 1 1
AYena fatua . 2 1 1 9 1 1 9 1 1
AmR~anthus retroflexus 2 1 1 6 1 2 9 2 9 9
Chenopotium album 6 1 1 9 1 2 9 2 9 9
~ ~ 4 8 9 8 7 9 9 9 9 .
~ ~ 7~8 5
- 15 -
If the values relating to the additive action calculated
by the method of Colby are compared with the results
reported in Table 5, then it is evident that the observed
growth figures given for Amaranthus retr., Chenopodium alb.
and Sinapis arvensis are lower than those calculated. The
synergistic effect of the combination of 4-(3',5'-dichloro-
pyridyl-2l-oxy)--phenoxythiopropionic acid
propargyl ester and Metamitron is thus demonstrated (cf.
Table 6).
able 6: Values calculated by the method of Colby for
demonstrating the synergism of 4-(3',5'-
dichloropyridyl-2'-oxy)-~-pheno~ythiopropionic
acid propargyl ester (compound Ib) and
Metamitron (compound IIa).
.. _ .
compound IIa l.o 0.5 0.25
kg a.i./ha_ 0.5 0.25 o 5 0.2s 0.2
~ ":1 D ~I D ~ D = D ~ ~
sugar beet
'Kawemono' 100 100 100 100 100 100 100 100 100 100
fodder beet
'Corona' 100 100 100 100 100 100 100 100 100 100
Panicum c.g. 1 1 1 1 1 1 1 1
Avena ~atua 1 1 1 1 1 1 1 1
Amaranthus retr.1 12 1 12 1 62 12 62 12 100
Chenopodium al~.1 62 1 62 1 100 12 109 12 100
Sinapis arvensis37 100 87 100 87 100 75 100 100 100
l~7~85
- 16 -
) Table 7: Tolerance and activity of 4-(3',5'-dichloro-
pyridyl-2'-oxy)-a-phenoxythiopropionic acid
propargyl ester (compound Ib) and Phenmedipham
(compound IIb) and mixtures thereof, when
applied postemergence.
Phenmedipham (comp. IIb) ¦
kg a~i./ha l.o 0.5 O.Z5 O
._ . ., . ._ , __
compound Ib kg a.i./ha -o -o o o o o o o o o
, ... _ . _ ~ . _.
sugar beet 'Kawemono' 9 9 9 9 9 9 9 9 9 9
fodder beet 'Corona' 9 9 9 9 9 9 9 9 9 9
P~nicum crus-galli 2 1 1 3 1 1 8 1 1
Ava~a fatua g 1 1 g l l 9 1 1 1
ra~thu~ retroflexus 9 7 8 9 7 9 9 9 9
Chenopotiu~ album 3 2 2 4 2 2 9 9 9
SiDapi arv~n-~is 2 2 2 7 3 4 9 9 9
If the values relating to the additive action calculated
by the method of Colby are compared with the results
reported in Table 7, then it is evidént that the observed
growth figures given for Amaranthus retr., Chenopodium
alb. and Sinapis arvensis are lower than those calculated.
The synergistic effect of the combination of 4 (3',5'-
dichloropyridyl-2'-oxy)-a-phenoxythiopropionic acid propargyl
ester and Phenmedipham is thus demonstrated (cf. Table 8).
able 8: Tolerance and activity of 4-(3',5'-dichloro-
pyridyl-2l-oxy)-a-phenoxythiopropionic acid
propargyl ester (compound Ib) and Phenmedipham
(compcund IIb).
~ ~ 7~5~i
- 17 -
compkund Iib/ha ¦ 1.0 0.5 0.25
comp~und Ib/h ¦ 0 5 0.25 0.5 0.25 0.25
~ a~ a~ aJ Q~
.,1 ~ .~ a~ .,~ ~ .,~ ~ .,~ v
e ~ ~ ~ e ~ E ~ ~i ~
aJ ~ ~ u ~ ~ a~ u a~ 5
a~ a) ~ c~
J~ 1
a) ~ d ~ d a~ ~d X ~ ~ ~ ~C td a) ~ X
~ ~ ~ ~ ~ ~ '13 ~ ~ ~ ~ ~
.. - _ . . . _ .
sugar beet
'Kaweno' 100 loO loO lOo 100 lOo loo loo loo loo
fodder beet
'Corona' 100 100 100 100 100 loO lOo loo lOo loo
Pa~ic~m c.g. 1 1 1 1 1 1 1 1
Avena f atua l 1 1 1 1 1 1 1
kmaranthu~ retr.7,5lOo 87 lOo 75 100 100 100 lOo 100
Che~opodium alb.12 25 12 25 12 37 25 37 37 100
51~apl~ ar~ens~512 1~ 12 12 25 75 37 75 100 100
.
Formulation Examples
Example 2
Formulation examples for syner~istic mixtures of com~ounds
of the formulae I and II (throughout, percentages are by we~t)
a) Wettable powders a) b) c) d)
compound Ia or Ib 10% 20% 5% 30%
compound IIa or IIb 10% 40% 15% 30%
sodium lignosulfonate 5% 5% 5% 5%
sodium laurylsulfate 3% - 3%
sodium diisobutylnaphthalene-
sulfonate - 6% - 6%
octylphenol polyethylene
glycol ether (7-8 moles of
ethylene oxide) - 2% - 2%
highly dispersed silicic acid 5% 27% 5% 27%
kaolin 67% - 67%
8 5
- 18 ~
The active ingredient mixture is thoroughly mixed with the
adjuvants and tha mixture is thoroughly ground in a
suitable mill, affording wettable powders which can be
diluted with water to give suspensions of the desired
concentration.
b) Emulsifiable concentrates a) b) c)
compound Ia or Ib 5% 5% 12%
compound IIa or IIb 5% 20% 13%
octylphenol polyethylene
glycol ether ~4-5 moles of
ethylene oxide) 3% 3% 3%
calcium dodecylbenzene-
sulfonate 3% 3% 3%
castor oil polyglycol ether
(36 moles of ethylene oxide) 4% 4% 4%
cyclohexanone 30% 30% 30%
~ylene mixture 50% 35% 35%
Emulsions of any required concentration can be obtained
from these concentratesby dilution wi~h water.
c) Dusts a) b) c) d)
compound Ia or Ib 2% 4% 2% 4%
compound IIa or IIb 3% 4% 4% 8%
talcum 95% - 94%
kaolin - 92% - 88%
Dusts which are ready for use are obtained by mixing the
active ingredient mixture with the ~arriers, and grinding
the mixture in a suitable mill.
1 J ~&5~i
- 19 -
d) xtruder ~ranulates a) b) c)
compound Ia or Ib 5% 3% 5%
compound IIa or IIb 5% 7% 15%
sodium lignosulfonate 2% 2% 2%
carboxymethylcellulose 1% 1% 1%
kaolin 87% 87% 77%
The active ingredient mixture is mixed and ground with the
adjuvants, and the mixture is subsequently moistened with
water. The mixture is extruded and then dried in a stream
of air.
e) Coated granulates a) b)
compound Ia or Ib 1.5% 3%
compound IIa or IIb 1.5% 5%
polyethylene glycol 200 3.0% 3%
kaolin 94.0% 89%
The finely ground active ingredient mixture îs uniformly
applied, in a mixer, to the kaolin moistened with poly-
ethylene glycol Non-dusty coated granulates are obtained
in this manner.
f) Suspension concentrates a) b)
compound Ia or Ib 20% 20%
compound IIa or IIb 20% 40%
ethylene glycol 10% 10%
nonylphenol polyethylene
glycol ether (15 moles of
ethylene oxide) 6% 5%
" i 1 7~8~1
20 ~
sodium lignosulfonate10% 10.0%
carboxymethylcellulose1% 1.0%
37% aqueous formaldehyde
solution 0.2 % 0.2%
silicone oil in the form of
a 75% aqueous emulsion0.8% 0.8%
water 32.0% 12.0%
The finely ground active ingredient mixture is intimately
mixed with the adjuvants, giving a suspension concentrate
from which suspensions of any desired concentration can be
obtained by dilution with water.
