Note: Descriptions are shown in the official language in which they were submitted.
3~ 4
IIOECHST AKTIENGESELLSCHAFT HOE 86/F 104J Dr.AU/mu
Herb;cides
. .
The present invention reLates to herbicides which contain
an active ingredient of the formula I,
~P - CH2 - CH2 - C - CI- V Y (I)
in which
A1 denotes H and AZ denotes NH2, or A1 and A2
together denote an oxygen atom,
V denotes O or NH,
Y, where V = O, denotes hydrogen or (C1-C4)alkyl, or
Y, where V = NH, denotes a radical of the formula
-CH(CH3)-CONH-CH(CH3)-COOH or -CH(CH3)-CONH-
CH[CH2CH(CH3)2]-COOH, and, irrespective of the
meaning of V,
W denotes hydrogen,
or a salt thereof,
in combination w;th a compound of the formula II
R - S02 ~ NH - C - N ~ ~ tII)
in which
: R1 denotes (C1-C4) alkyl, (C~-C6) alkenyl,
(C2-C6) alkynyl, which may in each case be halo-
genated, (C1-C4) alkylamino, d;(C1-C4-alkyl)-
amino, [N-(C1-C4-alkylsulfonyl)-N-(C1-C4-alkyl)]-
amino, where the alkyl radicals may be halogenated,
phenyl, benzyl, phenoxy, pyrazolyl or thienyl which
: 25 may all be substituted by (C1-C4) alkyl, (C2-C
alkenyl, (C2-C6) alkynyl or (C1-C4) alkoxy
which may all be substituted by halogen or (C1-C4-
alkoxy)carbonyl,
.
~l.2~13~L
furthermore by halogen, CF3, nitro or a radical
of the formula -CooR4, in which
R4 denotes H, ~C1-C4) alkyl, (C2-C6)-
alkenyl, (C2-C6) alkynyl, (C1-C4) alkoxy-
(C1-C4) alkyL or halo (C1-C4) alkyl,
furthermore by a radical of the formula -Sto)nR5,
in which
R5 denotes ~C1-C4) al.kyl, (C1-C4) alkoxy,
halo (C1-C4) alkyl, (C1-C4) alkoxy-
(C1-C4) alkyl, (C1-C4) alkoxy-carbonyl-
(C1-C4) alkyl, di(C1-C4-alkyl)-amino~
(C1-C4) alkylamino, (C1-C4) alkoxy-
(C1-C4)alkylamino, and n denotes 0, 1 or 2,
R1 denotes H, (C1-C4)alkyl or (C2-C4)alkenyl,
: 15 R2 and R3, independently of one another, denote (C1-C4)-
alkyl or (C1-C4) alkoxy wh;ch are both
opt;onally monosubstituted or polysubstituted
by halogen, (C1-C4) alkoxy or (C1-C4-
~ alkoxy)-carbonyl, (C2-C6) alkenyl,
; :: 20 (C2-C6) alkynyl, (C2-C6) alkenyloxy,
; (C2-C6) alkynyloxy or halogen,
; X denotes 0, S or NR6, where R6 =
(C1-C4) alkyl or (C1-C4) alkoxy, and
Z denotes CH or N, or a salt thereof,
or with a compound of the formula III or lll', or salts
thereof,
::
~ ~ :
: ~
~29~34~L
-- 3
R7 ~ / ~ R7 ~ ~ (III')
CH3 (III) N C~
¦ CH(CH3~ CH(C~2
in which
R7 denotes phenyl, pyridyl, ancl quinolyl which are all
optionally monosubstitutecl or polysubstituted by
~C1-C4) alkyl or (C1-C4) alkoxy, which may both be
monosubstituted or polysubstituted by halogen, are
further substituted by a radical of the formula
-CooR9, -coo CH2R9-CooR9,
-CH2R9-COO(C1~C4-alkyl) or CH2R9-CooCH2R9
CooR9,
; in which, in each case independently of one another,
R denotes~ H or ~C1-C4) alkyl,
or a radical of the formula -CH2-S(O)n-(C1-C4)-
alkyl, where n denotes 0, 1 or 2, and
R8 denot~es H or~a rad;cal of the formula -CONH(C1-C4-
alkyl), -OCO(C1-C4-alkyl) or -CO(C1-C4-alkyl)~
In the case where R8 - H, the two formulae III and IIl '
ex;st in tautomeric equilibrium. Depending on the radi-
cal R8 and the other substituents, the one or the other
-form ~III or III:' ) can therefore be present, see German
Offenlegungsschrift 3,121,636 and German Offenlegungs-
schrift 2,833,274.
The compounds of the formula I~where V = O are described
in U S. Pa~tent 4,168,936 and European Patent 30,424,
whereas the compounds of the formula I where V = NH are
~-: : known from U.S. Patent 4,309,208, S. Omura et al., The
34~
-- 4 -
Japanese Journal of Antibiotics, Volume YXXVIII-2, p. 542
(1985); and H~S. Seto et al., The Journal of Antibiotics,
Vol. XXXVI 1, pp. 96 - 98 (1983). Of the compounds of
the formula I, preferred compounds are
Ia: A1 = H, A2 = NH2; V - Y = OH, W = H, and the
salts thereof; monoammonium salt; common name:
glufosinate-ammonium~
Ib: A1 and A2 together = oxygen; V - Y = OH, W = H,
and the salts thereof.
Ic: A1 = H, A2 = NH2; V = NH; Y = -CH(CH3)-CONH-
CH(CH3)COOH, W = H, and the salts thereof; common
name: bialaphos.
Id: A1 = H, A2 = NH2; V = NH; Y = -CH(CH3)-CONH-
CH(CH2CH-(CH3)z)COOH, W = H, and the salts
thereof; common name: phosalacine (S. Omura et al.
The Japanese Journal of Antibiotics, 37 (2), p. 542
(1985)).
Preferred compounds of the formula II are:
Type 1: Alkylaminosulfonylureas of the abovement;oned
: ~ 20 formula II, ;n wh;ch
R1 denotes lN-(C1-C4-alkylsulfonyl)-N-(C1-
C4-alkyl)amino], where the alkyl radicals
may ;n each case be halogenated, and X
denotes O, see EP-A 131,258; of these, the
compound IIa in which R1 denotes ~CH3SO2~-
(CH3)N-, R2 and R3 denote OCH3, and
Z denotes CH are of particular importance.
Type 2: Pyrazolylsulfonylureas of the abovementioned
formula II in which R1 denotes a radical of the
formula
-- 5 --
R10
R9
in which
R9 has the abovementioned meaning,
R10 denotes H, (C1-C4) alkyl, (C1-C4) alkoxy, or
S a radical of the formula -CooR4 or -S(o)nR5 , in
wh;ch R5 = (C1-C4) alkyl, (C1-C4) alkoxy,
halo (C1-C4) alkyl, (C1-C4) alkylamino or
di(C1-C4-alkyllamino, and
R11 denotes H, halogen, (C1-C4) alkyl or (C1-C4)
alkoxy, which may both be halogenated, and X denotes
O, see EP-A ~7,780.
Of these compounds, the:following are particularly suit-
able according to the invention:
Compound lIb: R1 _ H, R1 = 1,3,5-t~rimethyl-pyrazol-4 yl,
X = 0, R2 = CH3, R3 = OCH3 andZ = N.
Ilc: R1 := H, R1 = 1,3,5-tr;methyl-pyrazol-
4-yl, X = O, R~ = CH3, R~ = OCH3 and
z = CH.
IId: R1 = H, R1 = 1,3,5-trimethyl-pyrazol-
: 20 4-yl, X = O, R2 = R3 = CH3~:~and Z = CH.
IIe: R1 := H, R1 = 5-chloro-1,3-dimethyl-
~ : pyrazol-4-yl, X = O, R2 = CH3, R3 =
::~ : : OCH3 and Z = N
IIf:~R1 =;H, R1 = 5-chloro-1,3-~di~ethyl-
py~razol-4-yl, X = O, R2 = CH3, R3 =
: OC~H3 and Z =~CH.
:: IIg~ R1 = H, R1 = 5-chloro-1,3-dimethyl-
pyrazol-4-yl, X = O, R2 = R3 =~CH3 and
Z = CH.
~: :
.,,
~l ~S~3~'3~4
IIh: R1 = H, R1 = 1,5-dimethyl-pyrazol-4-
yl, X = O, R2 = R3 = 0CH3 and Z = CH~
IIi: R1 = H, R1 = 1,3-dimethyl-5-difluoro-
methoxy-pyrazol-4-yl, X = O, R2 = CH3,
R3 = OCH3 and Z = H.
IIk: R1 = H, R1 = 4-ethoxycarbonyl-1-methyl-
pyrazol-5-yl, X = 0, R2 = R3 = CH3 and
z = CH.
II(~): R1 = H, R1 = 4-ethoxycarbonyl-1-methyl-
pyrazol-5-yl, X - O, R2 = R3 = OCH3 and
Z = CH.
Type 3: Thienylsulfonylureas of the abovementioned
formula II, in which
R denotes a radical of the formula
R
;n which
R1Z denotes H, halogen, tC1-C~) alkyl,
(C2-C4) alkenyl or (C1-C4) alkoxy, where all
three of the lastmentioned radicals may be halo-
genated, a radical of the formula -CooR4 where
R = H, (C1-C4) alkyl or (C2-C6)alkenyl,
~: or a radical of the formula -S(o)n-R5 , and X
denotes 0, see U.S~ Patent 4,431,029, JP-A 60/
~; ~ 197,676, JP-A 60/139,691 and JP-A 6U/193,983.
Of these compounds, examples which may be men-
: tioned are the compounds
IIm: Ri = 2-methoxycarbonyl-3-thienyl, R1
H, X = o,:R2 = 0CH3, R3 = CH3 and Z = N
: (thiameturon-methyl)
IIn: R1:= 3-(pentafluoro-1-propenyl)-2-
; thienyl, R1 =~H, X = O, R2 and R3 ~
: OCH3, Z = N or CH
IIo: R = 3-(2-chloro-1,2-difluoroethenyl)-2-
:~
3~A~
~ 7 --
thienyl, R1 = H, X - O, R2 and R3 =
OCH3 and Z = N or CH
IIp: R1 = 3-(2-chloro-1,2-difluoroethenyl)-
2-thienyl, R1 = H, X = O, R2 = CH3,
R3 = OCH3 and Z = N or CH
Ilq: R1 = 3-(pentafluoro-1-propenyl~-2-
thienyl, R1 = H, X = O, R2 = CH3,
R3 = OCH3 and Z = N or CH
Type 4: Phenyl-, phenoxy- and ben~ylsulfonylureas of the
formula II, in which
R1 denotes phenyl, phenoxy or benzyl which may
both be substituted by halogen, (C1-C4)
alkyl or (C1 C4) alkoxy which may both
be halogenated, or a radical of the formula
-CooR4 or -S(o)nR5 , and
X denotes 0, see EP-A 51,466, EP-A 113,956
EP-A 7,687 and U.S. Patent 4,514,212.
Amongst these, the following compounds may be
mentioned as examples:
IIs: R1 = H, R1 = 2-ethoxycarbonyl-phenyl,
X = 0, RZ = Cl, R3 = OCH3 and Z = CH
IIt: R1 _ H, R1 = 2-methoxycarbonyl-phenyl-
methyl, X = O, R2 = R3 = OCH3 and Z = CH.
IIu: R1 = H, R1 = 2-methoxycarbonyl-phenyl,
: :: 25 X = O, R2 and R3 = CH3 and Z = CH;
common name: sulfometuron-methyl
IIv: R1 - CH3, R1 = 2-methoxycarbonyl-
phenyl, X = O, R2 = CH3, R3 = OCH3 and
. Z = N
:. 30 IIw: R1 = H, R1 = 2-me:thoxycarbonyl-phenyl,
X = O, R~ = CH3, RJ a OCH3 and Z = N
:: (metsulfuron-methyl)
~: :
~9~34~
IIx: R1 = H, R1 = 2-(2-chloroethoxy)-phenyl~
X = O, R2 = CH3, R3 = OCH3 and Z = N
lIy: R1 = H, R1 = Z-chlorophenyL, X = 0,
R = CH3~ R3 = OCH3 and Z = N
(chlorsuLfuron)
Compounds which may be mentioned as being preferred
amongst the compounds of the formula III or IlI ' are
those in which
R7 = pyridyl which may be substituted by (C1-C4)-
alkyl, or a radical of the formula -CooR9,
-CooCH2R9 CooR9, -CH2R9-COO(C1-C4-alkyl),
-CH2(R9)-CooCH2R9-CooR9 or -CH2-S(0)n-
(C1-C4 alkyl), and
R8 has the abovementioned meaning.
(see Japanese Offenlegungsschrift 59/225,180,
EP-A 133,311 and EP-A 41,624).
; 0f these compounds III and III', compounds which may be mentioned as examples are
IIIa: R7 = 3-methoxycarbonyl-2-pyr;dyl and
R8 = methylaminocarbonyl.
IIIb: R7 = 3-methoxycarbonyl-2-pyridyl and
R8 = ethylaminocarbonyl.
: ~ IIIc: R7 = 3-methoxycarbonyl-2-pyridyl and
;~ R8 = methoxycarbonyl4
~ 25 IIId: R7 = 3-carboxy-Z~pyridyL and
; R8 = H; the isopropyLammon;um salt has the common
name: ;mazap;r.
Amongst the compounds of the formulae III and III', the
34~
following compound is furthermore of particular import-
ance:
IIIe: R7 = 2-methoxycarbonyl-5-methyl-phenyl and R8 =
The combinations according to the invent;on also cover
the salts of the compounds of the formulae I to III
which can be employed for agriculture.
Su;table as such are, for example, the conventional
alkali metal salts, alkaline~earth metal salts, substi-
tuted or unsubstituted ammonium salts, phosphonium salts
or sulfonium salts. Amongst the alkaline-earth metal
salts and alkali metal salts, the Na, K, Mg or Ca salts
are to be mentioned primar;ly.
Furthermore, the compounds of the formula I can also
form acid-addition salts with ;norganic acids, such as
HCl, H~r, HzS04 or ~3P04, or w;th organ;c acids,
such as tC1-C4) carboxylic acids, chlorinated acetic
acids, tartaric ac;d or citric acid; these are likewise
covered by the invention.
Furthermore, formula I and formula III or III' also cover
all corresponding stereoisomers and the mixtures thereof,
so that these likewise come under the combinations
according to the invention.
The present invention also relates to three-component
combinations of compounds of the general formula I with
two different active ingredients of the general formula
II or III.
The herbicidal active ingredient combinations mentianed
exhibit a surprisingly high act;vity which is greater
than could have been expected as a result of the actions
of the individual components.
The active ingredient combinations according to the
34~
- 10 -
invention cover a broad range of weeds. They are suit-
able, for example, for combating annual and perennial
weeds, such as, for example, Agropyron, Paspalum, Cynodon,
Imperata, Pennisetum, ConvolvuLus, Cirsium, Rumex and
others.
The combinations according to the invention can be
employed for selective combating of harmful plants in
pLantation crops, such as oil palm, coconut palm, rubber
tree, citrus fruit, pineapple, cotton, coffee, cocoa
inter alia, and also in fruit growing and viticulture.
Likewise, the combinations according to the invention
can be employed in arable farm;ng in the so-called "no
till" or "zero till" methods~ However, they can also be
used non-selectively on paths, squares, industrial works
etc. in order to keep these areas free of undesired
vegetat;ve growth.
The ratios of the compounds of the formula I to the com-
pounds of the formula II or III in the mixtures can vary
within broad limits, in particular between about 500:1
to 1:10. The choice of mixture ratio depends on various
parameters, such as the type of mixture partners, stage
of development of the weeds and the range of weeds.
Mixture ratios from 100:1 to 1:5 are preferably selected.
The combinations according to the invention can be pre-
sent both in the form of mixed formulations - wettable
powders, emulsion concentrates - which are then used in
a convent;onal fashion diluted with water; however, they
can also be prepared as so-called tank mixes by common
dilution of the separately formulated components with
water
The application rates of the herbicide of the formula I
in the active ingredient mixtures generally vary between
0.25 and 4.0 kg/ha, whereas the application rates of the
compounds of the formula II or III can be in the range
between 0.01 and 5.0 kg/ha, specifically for
~ ~9~344
of the formula IIJ, between 0.01 and 2.0 kg of
a.i./ha
" type 1 " 0.01 and 1.0 kg of
a.i./ha
" type 2 " 0.01 and 0.5 kg of
a.;./ha
" type 3 " 0.01 and 0.5 kg of
a.i./ha
" type ~ " 0.05 and 2.0 kg of
a~i~/ha
and
compounds of the formula III " 0.05 and 2.0 kg o~
a.i./ha
The agents according to the invention can be marketed in
the conventional formulations which are known to those
skilled in the art, for example as wettable powders,
dusting agents, granules, dispersion concentrates, emul-
s;f;able concentrates or sprayable solut;ons. In this
case, the formulated agents generally contain the active
ingredient in concentrations from 2 to 95% by weight.
Wettable powders are preparations, uniformly dispersible
in water, ~hich contain, besides the active ingredient
and in addition to a diluent or inert material, wetting
agents, for example polyoxyethylated alkylphenols, poly-
oxyethylated oleylamines or stearylamines, alkylsulfon-
ates or alkylphenyl sulfonates, and dispersing agents,
for example sodium ligninsulfonate, sodium dinaphthyl-
methanesulfonate or also sodium oleylmethyltaurinate~
Emulsifiable concentrates are obtained by dissolving the
active ;ngred;ent mixture in an organic solvent, for
example butanol, cyclohexanone, dimethylformam;de, xylene
or alternatively higher-boiling aromatics~ and adding a
nonionic wetting agent, for example a polyoxyethylated
alkylphenol or a polyoxyethylated oleylamine or stearyl-
amine.
:~
- 12 -
In wettable powders, the total concentration of act;ve
ingredient is between about 10% and 95%, and the rest
comprises the abovement;oned formulation additives. In
the case of emulsifiable concentrates, the active ingredi-
ent concentration is about 10% to 80%. Dust-like formu-
lations usually contain 5% to 20% of active ingredients,
sprayable solutions about 2% to 20%. In the case of
granules, the active ingredient content depends partly
on the form (liquid or solid) in which the active ingred;-
ents are present and on which granulation auxiliaries,fillers etc. are used.
For use, the commercially available concentrates are, if
appropriate, diluted in a conventional fashion, for
example using water in the case of wettable powders and
emulsifiable concentrates.
Dust-like and granulated formulations and sprayable solu-
tions are not d;luted with further inert substances before
use.
A. Formulation Examples
a) The dusting agent ;s obtained by m;xing 10 parts by
weight of act;ve ;ngredient mixture and 90 parts by
weight of talc as inert material, and comminuting
in a hammer mill.
b) The wettable powder which is easily dispersible in
water is obtained by mixing 25 parts by weight of
active ingredient mixture, 64 parts by weight of
kaol;n-containing quartz as inert material, 10 parts
by weight of potassium ligninsulfonate and 1 part by
weight of sodium oleoylmethyltaurinate as wetting and
dispersin~q agent, and grinding in a p;n disc mill.
c) The dispersion concentrate which is easily d;spers-
ible ;n water is prepared by mixing 20 parts by
weight of active ingredient mixture with 6 parts by
~.Z9~34~
weight of alkylphenol polyglycol ether ~ riton X
207), 3 parts by we;ght of isotridecanol polyglycol
ether (8 E0) and 71 parts by we;ght of paraff;nic
mineral oil (boiling range, for example about 255 to
above 377C), and grind;ng ;n a ball m;ll to a
fineness of below 5 microns.
d) An emulsifiable concentrate is obtained from 15 parts
by weight of active ingredient mixture, 75 parts by
weight of cyclohexanone as solvent and 10 parts by
weight o~ oxyethylated nonylphenol ~10 E0) as emul-
sifier.
B. Biological Examples
Synergism is detected in the following examples by com-
paring ~he additive degree of act;on calculated from the
actions of individual components with the experimentally
found degree of action of the active ingredient combina-
tions. The additive degree of action ;s calculated
according to the formula of S.R. Colby (cf. Calculating
synergistic and antagonistic responses of herbicide com-
binations, Weeds~ 15, 1967, pp. 20 to 22).
This formula is:
X . Y
E = X ~ r -
100
where
X denotes the ~ damage by herbicide A at an application
rate of x kg/ha,
Y denotes the % damage by herbicide B at an application
rate of y kg/ha,
E denotes the ~xpected % damage by herbicides A + B at
an appl;cation rate of x + y kg/ha.
If the actual damage is greater than that calculated, the
~'3i~3~L
- 14 -
act;on of the active ;ngredient combination is more than
additive, i.e. there ;s a synerg;st;c effect.
Example 1
. _ _
Seeds of var;ous weed grasses and weeds were sown ;n
sandy loam in plastic pots (~ 9 cm) and raised for 3 - 4
weeks ;n a greenhouse under good growth cond;t;ons. The
compounds of the formula I, formulated as aqueous solu-
t;ons, water-d;spersible powders or emulsion concentrates,
and the combinat;on partners were subsequently sprayed,
alone and in combination, ;n the form of sprayable solu-
t;ons onto the above-ground parts of the plants~ The
amount of water used in this corresponded to 400 l/ha.
After standing for about 3 weeks ;n the greenhouse under
;deal growth conditions, the herb;c;dal act;on was
assessed visually. The results are reproduced ;n Table 1
below.
Table 1:
Herb;c;dal action of the mixtures accord;ng to the ;nven-
tion under greenhouse conditions (according to E%ample 1)
20 ProductDosage, ~ act;on
kg of a.;./ha ECG PMI
Ia 0.125 10 65
0.060 o 30
IIu 0.008 30 55
25 Ia + IIu0.1Z5 ~ 0.008 90 (37) 95 ~84)
0.060 + O.Q08 75 (30) 80 (68)
Abbreviations:
ECG = Echinochloa crus-gall;
PMI = Panicum miliaceum
a.i. = active ingredient
Ia = glufosinate
~l ~9~l~349~
IIa a sulfometuron-methyl
( ) = expected value according to Colby
The results show that an unexpectedly h;gh herbic;daL
activity which is considerably better than could have
been expected as a result of the sum of the indiv;dual
actions of the active ingredients was achieved using the
active ingredient combination.
Example 2
In a field experiment under tropical conditions, the
preparations glufosinate-ammonium (Ia) and imazapyr (IIId)
were tested alone and ;n combination in a crop of the
gramineae Imperata cylindrica. At the time of applica-
tion, this species of gramineae had a growth height of
80 to 1Z0 cm; the inflorescence had already formed. The
experimental area was not shaded by trees~ A standard
knapsack sprayer was used for the treatment; the experi-
mental plots had an area of 16 m2.
Each treatment was repeated three t;mes. Evaluation was
carried out by visual estimation of the damage.
The results are shown ;n Table 2 below, the actions
having been determined as average vaLues for the damage
(in %) from three experiments in each case. The values
;n parentheses represent the values to be expected
according to the Colby formula.
It can be seen from the results that Ia on its own
achieved an average to good initial action at the dosages
tested; however, the action of Ia feLl off in the course
of 12 to 20 weeks since resprouting occurs from the
below-ground rhizomes. In contrast, herbicide IIId has
a weak initial action, and the action was not compLetely
satisfactory even 12 weeks after application.
For comb;ned use of Ia and IIld, where the low and
~C31344
- 16 -
average dosages for both products were used, ;t became
apparent that both the init;al and the long-term action
were considerably better than for the individual compon-
ents; they were markedly greater than the actions cal-
culated according to the Colby formula. Synerg;sm ;stherefore present.
Table 2:
Action on lmperata cyl;ndr;ca
_ _
Product Dosage, % action after ~. days
kg of a.i./ha 28 84 140 (d)
Ia 1.5 53 34 13
2.0 82 39 15
3.0 89 62 54
IIId 0.25 5 35 40
0.375 7 50 55
0.5 14 72 76
Ia ~ IIId 1.5 + 0.25 68 93 74
t55.35) (57.1) (47.8)
1.5 + 0.375 83 97 87
(56.29) (67.1) (60.85)
200 + O.~S 85 98 ~2
(82.9) (60035) t49.0)
2.0 ~ 0.375 88 98 ~9
t83.26) (69.5) (69.7S)
- _ .
a~;. = active ingredient
Ia = glufosinate-ammonium
IIId = imazapir
d = days
Exam
Under field condit;ons, a crop of various annual and per-
ennial weeds having a growth height of 5 to 15 cm was
divided into plots of 8 m2.
9~L34
- 17 -
These plots were then treated with the mixtures accord;ng
to the invention and with the individual components
form;ng these mixtures on their own at var;ous applica-
tion rates using the post-emergence method. The amount
of water applied here was 400 l/ha. After 30 days, the
plant damage compared to untreated experimentaL samples
was assessed visually.
The activities of the mixtures and of the ind;v;dual
components aga;nst the var;ous weeds are collated ;n
Table 3.
The experimental results shown clearly prove the syner-
g;stic actions of the m;xtures accord;ng to the ;nvent;on
compared to the act;vities of the ;nd;v;dual components.
Th;s synergism can be seen particularly clearly on per-
ennial weeds which are difficult to combat, such as, forexample, Agropyron or Cirsium.
Table 3:
. . .
Product Dosage, % action
kg of a.i./ha A6R _IA CAR
20 Ia 0.5 40
1.U 27 55 55
IIu 0.0125 23 70 0
Ia ~ IIu 0.5 + 0.0125 63 (23) 80 (70) 65 (40)
1.0 + 0.0125 68 (43) 92 (86) 85 (55)
, . . ~
Abbreviations.
AGR = Agropyron repens
SIA = Sinapis arvensis
CAR - Cirsium arvense
a.i. = active ingredient
Example 4
Plants of CommeLina communis and Amaranthus retroflexus
1 2~'-3~l34~
18 -
were ra;sed analogously to Example 1 ;n pots (~ 10 cm)
and, at a growth height of about 25 cm, treated with the
mixtures according to the ;nvent;on and the individual
components on their own with a water appl;cation rate of
1,000 l/ha.
Evaluation by means of visual assessment occurred after
about 3 weeks.
The results of this experiment are collated in TabLe 4.
As the data illustrated clearly show, the mixtures of
glufosinate-ammonium and various sulfonylurea derivatives
exhibit clearly synergistic actions, since in all cases
the degrees of action of the mixtures are considerably
greater than the values calculated according to Colby for
additive effects.
34~
- 19 -
Table 4:
Product Dosage ~ action
__ _k,~ a . i . /ha COMC0 _ AMARE
Ia 0, 4 40 5
IIu 0,1 0 5
0,05 0 5
0,1 o 5
0,5 o lO
IIy 0.0l 5
IIm 0,01 - 12
0,05 - lO
o,l _ 10
0,5 _ lO
IIw 0,01 - 5
0,05 - 5
0,1 - 5
0.5 _ 5
Ia + IIu 0,4 + 0,01 - 86 ( lO)
0,4 + 0,05 7~ (40) 92 (10)
0,4 + 0,1 63 (40) 99 (lO)
0,4 + 0,5 90 (40) 99 (15)
Ia + IIy 0,4 ~ 0,01 60 (40) 95 (10)
Ia + IIm 0,4 + 0,01 ~ _ 85 (16)
0,4 + 0,05 - 83 (l 5)
0,4 + 0~ l _ 8~ (l 5)
0,4 + 0,5 - 88 (l 5)
Ia ~ IIw 0,4 + 0,01 - 80 (l Oj
094 + 0,05 - ~0 (1 0)
o, 4 + o, 1 - 80 ( l 0)
0,4 + 0,5 - 85 (10)
Abbreviations:
COMCO = Commelina communis
AMARE = Amaranthus retroflexus
a.;. = actlve ingredient
~91~4~
- 20 ~
~ ) = expected values accord;ng to Colby
Ia = glufos;nate-ammonium
lIm = Th1ameturon-methyl
IIu = sulfometuron-methyl
S IIw = metsulfuron-methyl
IIy = chlorsulfuron
: :
