Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
~W093/056~5 21 19 6 ~ ~ PCT/EP92/02l85
.~
~ .
This invention relates to a new herbicidal composition
S having synergis~ic activity comprising a mixture of
6-~6,6-di~ethyl-3,5,6,7-tetrahydropyrrolo-
~2~l-c][l~2~4]thiadiazol-3 ylidenimino)-7-fluor
4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
-and another selective herbicide and its use for co~bating
weeds in crops.
T~e herbicidal acti~ity of 6-(6,6-dimethyl-
3,5,6,7-tetrahydropyrrolot2,1-c]tl,2,4]thiadiazol-
3-ylid2ni~ino)-7-fluoro-4-(2-prop~nyl)-2~-1,4-benzoxazin~
3(4H)-one is already known (EP 311 135). This compound has
the following chemical s~ructure (I)
O~N~N15 (I)
Selective herbicides which inhibit directly or in~irectly
photosynthesis, demonstrate inhibition o~ cell division or
possess hormone type activity are generally known. The
known substances however are not always satisfactoxy in
their activity in all areas o~ use.
It has now been found that a herbicidal composition which
comprises, as active ~omponents, a mix*ure of
6-(6,6-dimeth~1-3,5,6,7 tetrahydropyrrolo-
t2,1-C]tl,2,4~thiadiazol-3-ylideniminc:)-7-fluoro-
4-(2-propynyl~-2H-1,4-benzoxazin-3(4~)-one and anothex
~W093/0~655 2119 ~ ~ ~ PCT/EP92/02185
selective herbicide shows especially high activity without
losing the selectivity properties in agricultural crops.
Surprisingly the herbicidal activity of the combination o~
the active ingredients of the invention is essentially
higher than the indi~idual components and also of khe sum
of the individual components. A synergistic ef~ect is al~v
se~n.
Especially suitable are mixtures which contain as a
mixture component the selective herbicides cyanazine,
ioxynil, isoproturon, methabenzthiazuron, bifenox,
chlorsulfuron, metsulfuron-me~hyl, pendimethalin,
benfuresate, thifensulfuron-methyl, isoxaben,
imazamethabenz, triasulfuron, amidosulfuron, etho~um s~te,
diflufenican, tribenuron-methyl, ~ecoprop, 2,4-D,
benazolin-ethyl, fluroxypyx or quinmerac.
Cyanazine is the common name for 2-chloro-4-(1-cyano- ~ :
20 1-methylethylamino)-6-ethylamino-1,3,5-triazine;
ioxynil is the co~mon name ~or 4-hydroxy-3,5-diiodo~
benzonitrile;
i~oproturon i5 the co~mon name for 3-t4-isopropylphenyl)-
1,l-dimethylurea;
methabenzthiazuron is.the common name for l-(benzothiazol-
2-yl)-1,3-dimethyluxea;
bi~enox is the co~mon name for methyl 5-(2,4-dichlo~o-
phenoxy)-2-benzoate;
chlorsulfuron is the common na~e for 1-(2 chlornphenyl-
30 sul~onyl)-3~(4-methoxy-3-methyl-1,3,5-triazin-2-yl~urea;
metsulfuron~methyl is the co~mon name for methyl
2-~(4-methoxy-6-methyl-1,3,5-triazin 2-yl)amino-
carbonylaminosulfonyl]benzoate;
pendimethalin is ~he common name for N-(1-ethylpropyl)--
3,4-dimethyl-2,6-dinitroaniline;
x~
?~
;~W093/0565~ PCT/EP92/02185
:~19~S
benfuresate is the common name for 2,3-dihydro-
3,3-dimethyl 5-benzofuranyl ethanesulfonate;
thifensulfuron-~ethyl is the common name for methyl
3-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-
carbonylaminosulfonyl~-2-thiophenecarboxylate;
isoxaben is the co~mon name for N-t3-(1 ethyl-l-methyl-
propyl)isoxazol-5-yl]-2,6-dim~thoxybenzamid~;
imazamethabenz is the common name for 2-t4-isopropyl-
4 methyl-5-oxo-2-imidazolin-2-yl~-4(5)-methylbenzoate;
triasulfuron is the common name ~or 1-(2-chlorethoxy)
N-t(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- :
benzenesul~onamide;
amidosulfuron is the common name for 1-~4,6 dimethoxy-
pyrimidin-2-yl~-3-(N-methyl-N-methylsulfonylsul~a~oyl)-
urea;
etho~umesate is the common name for 2-ethoxy-2,3-dihydro-
3,3-dimethyl-5-benzofuranyl methanesulfonate;
diflu~enican is the common name for 2'~'-difluoro-
2-(~ -tri~luoro~m-tolyloxy)nicotinanilide;
tribenuron-methyl is the common name for methyl
2-~4-~ethoxy-6-methyl-1,3,5-triazin-2-yl(methyl)-
caxbamoylsulfamoyl~benzoate;
mecoprop is the common name for (RS1-2-(~-chloro-
2-methylphenoxy)propionic acid;
2,4-D is the com~on name for 2-(4-chloro-2-methyl~
phenoxy)acetic acid;
benazolin-ethyl is the common name ~or ethyl (4 chloro-
2,3-dihydro-2-oxo-1,3-benzothiazol-3~yl)acetate;
dicamba is the common name for 3,6 diohloro-2-methoxy-
benzoic acid
fluroxypyr is the common name for (4-amino-3,5-dichloro-
6-fluoro-2-pyridyloxy)acetic acid; and
guinmerac is the co~mon name for 7-chloro-3 methyl-
8-quinol~neca~boxylate.
- W093/OS6~5 2 .t ~ 9 6 ~i ~ PCT/EP92/02185
It
The combination of active ingredients ~f the invention can
used ~or example against the following plant species:
Dicotyledonous weeds of the species sinapis, Lepidium,
Galium, Stellaria, Matricaria, Anthemis, Galinsoga,
Chenopodium, Brassica, Urtica, Senecio, Amaranthus,
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,
Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,
Rorippa, Lamium, Veronica, Abutilon, Datura, Viola,
Galeopsis, Papaver, Centaurea and ChrysanthemumO
~onocotyledonous weeds of ~he species Avena, Alopecurus,
Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine,
Brachiaria, Lolium, Bromus, Cyperus, Agropyron,
Sagittaria, Monocharia, Fimbristylis, Eleocharis,
Ischaemum and Apera.
~he combinations can be applied pr~ or post-emergently,
but gener~lly pre-emergently. Selectivity is seen in range
of crops such as maize, cereals and sunflowers. The rate
of use lies between 0.001 and 5 kg/ha of the mixture,
depending on the use. By using the ~ixtures for control of
weeds the amount o~ herbicide needed can ~e generally
reduced.
The weight ratio of component a) to b) is generally
between 1:50 and 50:1.
The mixtures of the invention can also be used in
admixture with other active agents for example other
plant-protection agents or pesticides.
An improvement in the intensity and speed of action can be
obtained, for example, by addition of suitable adjuvants,
such as organic solvents, wetting agents and oils. Such
:,~.. : ~ ::.... : , . . ,, . . :, ~ , , .
; :. :., : ~ : , . , ;
-W093/0565S 2 1 ~ 9 6 ~ ~ PCT/EP92/02185
additives may allow a decrease in the dose.
The designated active ingredients or their mixtures can
suitably be used, for exa~ple, as powders, dusts,
granules, solutions, emulsion~ or suspensions, with the
addition o~ liquid and/or solid carriers and/or diluents
and, optionally, binding, w~tting, am~lsifying and/or
dispersing adjuvants.
Suitable li~uid carriers are, for example aliphatic and
aromatic hydrocarbons, such as benzene, toluene, xylene,
cyclohexanone, isophorone, dimethyl sulfoxide,
dimethylformamide and other mineral oil fractions and
plant oîls~
: -
Suitable solid car.~iers include mineral earths, e.g.
bentonite, silica gel, talc, kaolin, attapulgite,
limestone, silicic acid and plant products, e.gO flours. ~.
:
As surface-active agents there can be used ~or example
calcium lignosulfonate, polyoxyethylenealkylphenyl ethers,
naphthalenesulfonic acids and their salts, phenolsulfonic
acids and their salts, formaldehyde condensates, fatty
alcohol sul~ates, as well as substituted ~enzenesiulfonic
acids and their salts;
The percentage of the active ingredient(s) in the various
preparations can vary within wide limits. For example, the
compositions can contain about 10 to 90 percent by weight
acti~e ingredients, and about 90 to 10 percent by weight
liquid or solid carriers, as well as, optionally up to 20
percent by weight o~ surfactant.
The agents can be applied in customary ~ashion, for
example with water as t~e carrier in spray mixture v~lumes
W093/OS655 2 ~ PCT/EP92/0218~
b
of approximately 100 to 1,000 l/ha. The agents can be
applied using low-volume or ultra-low-volume techniques or
in the form of so-called microgranules.
The preparation of these formulations can be carried out
in known manner, for example by milling or mixing
processes. Opt~onally, individual components can be mixed
just before use for example by the so-called commonly used
tar;k-mixing method.
The following Examples illustrate the use of compositions
of the invention.
The calc~lation o~ synergistic effect is carried out
according to S R Colby "Calculating Synergistic and
Antagonistic Response to Herbicide Combinations" , Weeds,
15/1, 1967 pages 20 to 22. I~ this the following formula
S was used:
XY
E = X + Y ~
100
in which X = the herbicidal activity (%1 of substance A
at a rate of p g/ha.
Y = the herbicidal activity (%) of substance B
at a rate of q glha., and
E = the expected additive activity of the
herbicide (%) of the substances A ~ B at 2
rate of p + g g/ha.
If the observed value is greater than the value of E
calculated according to Colby, the combination shows
synergistic activity.
~ - ~093/0~6~5 PCT/EP92/02185
.. ; .
ExPeriments
In a greenhouse the plant species shown in the tables were
treated pre-emergently with the components at the stated
rates. The compositions were diluted with 500 litres of
water and sprayed over the soil. Two weeks a~ter treatment
the herbicidal effert was evaluated~ In the examples
compQnent I is 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo-
[2~l-c]tl~2~4]thiadiazol-3-ylidenimino)-7-fluor
4-~2-propynyl)-2H-1,4-benzoxazin-3(4H~-one
T~ble ~
~ixtures of I with mecoprop (II)
Component Rate ~erbicidal E (according
(g/ha) activity (%) to Colby)
lS Wheat
I 12.5 0
0
o
II 900 9
1800 17
I + II 12.5 ~ 900 10 (9)
12.5 + 1800 22 (17)
+ 900 10 (g)
+ lS00 22 (17)
S0 + ~00 14 (~)
+ 1800 14 (17)
~WO 93/05655 PCI/EP92/02185
21196~
Component Rate Herbicidal E ( according
(g/ha)activity (%) to Colby)
AloPecurus m~osu:~oides
I 25 0
0
II 900 16
1800 22
I + II 25 +900 24 (16)
0 25 + 1800 ~5 (22)
~ 900 26 ~16)
+ 1800 5~ (2~)
' ``W093/0565~ 9 2 ~ 19 6 ~ ~ P~/EP92/02185
Tæble B
MixtlLres of I with bif enox ( III )
Component Rate Herbicidal E ( according
(g/ha) activity (%) to Colby)
~ _ __ _ ._ _
Wheat
2 o
4 0
8 0
16 lO
III lO o
` 20
0
0
I ~ III 2 + lO 0 ( o )
` . 2 + 20 0 (
2 + 40 0 (0~
+ 80 0 (0)
4 + lO 0 (0)
4 + 20 0 (o)
4 + 40 0 (0)
4 + 80 ()
I + III 8 + lO o (o)
8 + 20 ~0 (0)
8 + 40 o (o)
8 ~ 80 0 (0)
16 + lO o (lO)
16 + 20 lO (lO)
16 + 40 o (lO)
16 ~ 80 o (lO)
- ....
W0 93/056~5 PCl~/EP92/02185
" 5
..
Co~por~entRate Herbicidal E (according
(g/ha) activity (%) to Colby~
BarLes~
~ 2 0
4 0
8 U
16 0
III 10 o
lo 20 o
0
0
+ III2 + lO o ( o )
2 ~ 20
2 + 40 o (o)
2 + ~0 0 (0)
4 + 10 0 (0)
J~ t 20 ~ ()
4 + ~0 0 (0)
4 + 80 o ~o
+ 10 o ( O
8 + 20 10 to)
8 + 40 10 (o)
~ t 8~ 0 (0)
16 + 10 10 (o)
16 + 20 10 (~ :
16 ~ 40 10
16 + 80 10
~"~,,,, ,; ~"-,~
~W093/~655 2119 6 ~ ~ PCT/EP92/02l85
~/1
Component Rate Herbicidal ~ (according
(g/ha)~ctivity (S) to Colby)
Galium aParine
I 8 30
16 50
III 10 o
~0 10
~0 20
I + III8 ~ 10 60 (30)
~ ~ 20 50 (37)
8 ~ 40 50 (37)
8 + 80 70 (44)
16 + 10 80 (50)
16 + 20 80 (55)
16 + 40 85 (55)
16 + 80 85 (60)
~iola sPp.
I 2 20
4 ~0
8 80
16 80
III 10 10
2~ 20 30
.. -
, . . . .
-~W093/05655 2 ~PCT/~P92/0218S
~I ~, .L :3 i ,J
Component Rate Herbi~idalE (according
(g/ha) activity (%) to Colby)
~_ _ _ _
I + III 2 ~ 10 50 (28)
2 + 40 60 (44)
4 ~ 10 80 (46)
4 + 20 70 (58)
4 + 40 ~0 (58)
8 + 10 85 (72)
16 + 10 95 (82)
Veronica ~ersica
I 4 20
. 8 60
III 10 10
I + III4 + 10 70 (28)
4 + ~0 60 (36)
~0 4 + 40 80 (68)
8 + 10 95 (64)
8 + 20 95 t68)
8 + 40 98 (~4)
8 + 80 98 (88)
~WO 93/056~ 21~ ~ 6 v l ~ PCI/EP92/02185
Component Rate Herbicidal E ( according
(g/ha) activity (%) to t~olby)
Matris:aria chamomilla
I 2 20
4 30
8 6~
16 70
III lO 0
2~ 0
o
0
I + III 2 ~40 40 (20)
2 +80 30 (~o)
4 ~lO 40 (30)
4 +20 40 (30)
4 +40 70 (3~)
4 ~80 40 (30)
~ +~0 80 (60)
8 +80 70 (60)
16 tlO 80 (70)
16 ~20 80 (70)
16 +40
16 + 80 90
25PolYaonum la~athifolium
2 20
4 50
8 70
16 80
~WO 93t056~5 2119 6 .~3 ^~; PCI/EP92/021B5
Co~ponent Rate! Herbicidal E (according
(g/ha) activity (%) ~o C:olby)
III lO lO
I + III 2 + lO 40 (2~)
4 +40 90 (75)
8 +40 95 (~5)
16 +lO 95 (~2)
,
10Sina~is arvensis
2 lO
4 20
16 60
III 20 lO
I + III 2 +40 30 (19)
4 ~ 40 40 (28)
16 + 20 90 (64)
':
`~W093/~65~ ~5 ?~ 1 96~ ~ PCT/EP~2/02185
Table_C
Mixtures of I with benazolin-ethyl (IV)
Co~ponent Rate Hexbicidal E (according
(5/ha) acti~ity (S) to Colby)
Wheat
I 2 0
4 0
8 0
16 0
IV 25 0
0
10~ 0
200 lO
I + IY2 + 25 0 (0)
2 1 50 0 (0~
2 + lO0 o (~)
2 + 200 o (lO)
4 + 25 0 (~)
` 4 + 50 ()
4 + lO0 o (0)
4 ~ 200 0 (lO)
I ~ IV8 + 25 0 (o)
8 ~ 50 0 (0)
8 + lO0 lO (o)
8 + 200 l~ (lO)
~',.
WO 93~0~65~ 21 1 9 6 5 ~PCI~/EP92/OZ185
CoDlponent Rate Herbicidal }: (according
(g/ha) activity (%)ko Colby)
16 ~ 25 10 (O)
16 + 50 io (o)
16 +1~0 10 ( O)
16 ~200 1~ (10)
Barley
2 0
lG 4 0
8 0
16 0
IV 25 0
0
100 0
200
+ IV 2 + 25 0 (O)
2 + 50 10 (O)
2 + 100 0 (O)
2 ~ 200 0 ~0)
4 + 25 0 (O)
~ ~ 50 10 ()
4 1 100 10 (O)
4 + 200 0 (O) ::
8 ~ 25 0 (o)
8 ~ 50 10 (o)
8 ~ lOO 10 (O) ;~
8 1 2~0 lO (O)
.
,
W093/~65~ 2 ~ ~ ~ PCT/EPg2/02185
. Component Rate Herbicidal E (according
(g/ha) activity (%) to Colby)
1~ + 25 10 (0)
16 + 50 20 (0)
16 + 100 20 (0)
16 + 200 10 (0)
~atricaria chamomilla
I 2 20
4 30
. 8 60
i
IV 25 o
0
100 0
200 10
I ~ IV2 + 100 30 (30)
2 -~ 200 50 S28)
4 ~ 25 040 (30)
4 + 50 40 (30)
4 + 100 70 (30)
4 + 200 60 (37)
.
~8 + 100 8~ (6
8 + 200 75 ~64)
WO 93/OSfi55 2119 ~ 5 5 P~/EP92/02185
~Ig
Component Rate Herbicidal E (according
(g/ha) activity ( %) to Colby)
Galium a~arine
I 2 0
4 10
8 20
16 50
IV 25 40
100 80
200 85
I~IV 41 25 60 t36)
4~ 50 75 (55)
154 + 100 95 (~2)
4 + 200 97 (~6)
8 + 25 70 (52)
8 + 50 90 (60)
8 + 100 97 (84)
208 + 200 99 ~88)
16 + 25 80 (70)
16 + 50 90 (75)
16 ~ 100 98 (go)
16 + 200 99
WO 93/05655 PCI/EP92/0~185
Component Rate Herbicidal E ( according
( g/ha ) acti vity ( % ~ tc~ Co lby )
Stellaria ~nedia
I 2
4 10
8 20
16 50
IV 2~ lO
100 70
200 90
I+IV 2+ 25 30 (10)
~+ 50 60 (30~
.2 ~ 100 80 (70)
2 ~ 200 97 (90
4 ~ 25 50 (19) :~
4 ~ 50 6~ (37) ~;
4 + 100 95 (73
~ + 200 98 (91)
8 ~ 25 fiO (28) : ~ :~
8 + ~0 70 (44~ :~
8 -~ 100 95 (76)
8 + 200 9~ (9~
16 1 25 60 (55)
~6 + 50 90 (65)
16 + 100 97 ~s)
16 + 200 99 (95)
WO 93/056~ 21 179 ~ F~ 5 Pcr/EP92/o2l85
:~ 2.o P-~
~'~ Co~Qponent Rate Herbicidal E (according
(g/ha) activity (%) to Colby)
___ _ _ _ .
Veronica ~ersica
5 I 2 10
8 60
IV 25 10
lOû 40
200 50
I+IV 2 1 50 40 ~19)
2 + lO0 70 (~5)
2 ~ 200 70 (55)
154 + 25 60 (28)
4 + 50 70 (28)
4 + 100 80 (S2)
4 ~ 200 80 (60
~.
8 + 50 80 (64) ;:
8 + 100 90 (76) `~
8 + 200 95 (80) ::
.:
,.. . . .
WO 93/056~5 . 2 1 ~ 9 6 ~ ~ PCI/EP92/021B5
~12
~ixtures of I with isoproturon (V)
Component Rate HerbicidalE ( according
(~/ha) activity (%) to Colby)
S _ . _ _ __ _
~heat
2 o
4 0
8 0
16 0
V 100 5
200 20
I ~ V 2 +100
4 ~100 10 (~)
8 ~100 10 (5)
16 + 100 10 (5)
2 + 200 20 (20)
~ + 200 20 (~0)
8 + 200 20 (20)
16 +200 20 (20)
Veronica ~ersica
2 30
4 70
V 200 10
I + V 2 +200 7û (37)
4 +200 85 (73)
W0 93/0~6~ 2,.2 21 1 9 6 ~ ~ PCI/EP92/02185
Component Rate ~Ier3~icidal E ( according
(g/ha~ activity (96) to Colby)
Setaria viridis
I 2 0
4 10
16 30
V 100 50
200 75
I + V 8 +100 70 (60
16 + 100 75 (65)
2 + 200 80 (75)
4 + 200 go (78) :~
15 8 t 200 90 (80)
16 +200 9o (83) :
~WO 93/056~ 23 2 1 ~ 9 6 ~ 5 PCI/EP92tO2185
~able E
Mix1:ures of I with ioxynil (VI )
Compon~nt Rate Herbicidal E ( according
(g/ha) ackivity (%) to Colby)
_ _ _ _
~heat
4 O
8 o
16 o
10 VI 50 O
100 ' O
I + VI 4 ~ 50 O (o)
8 + 5~ O ( o)
16 + so o (O)
4 t lOO o (o)
8 + lOO O (O)
16 ~ lO~ o (o)
.
Galium al~arine
8 10
16 80
VI 100 10
I + VI 8 ~100 10 t73)
Og3~05655 21 1 9 6 ~ 5 PCT/EP92~02185
Component Rate HerbicidalE (according
(g/ha) activity (%)to Colby)
Yiola_ 5~ .
I 4 50
16 80
VI 50 10
100 10
I + VI 4 1 50 70 (55)
4 + 100 85 (55)
16 ~ 50 B5 (82) ::~
~6 ~ lO0 gO (82) -~
~able F
Mixtures of I with metsulfuron-methyl (VII)
15 Component Rate HerbicidalE (according
~/h~) activity t$)t~ Colby~
Wheat
I 2 0
8 0
VII O.S o
1' 0
2 o
4 lO
-~ WO 93J05655 2~ 21~ 9 6 ~ 5 PCI/EP92/0218~
Component Rate HerbicidalE ( according
(gtha) activity (g6) to Colby)
I + VII 2 + 0.5 o ()
~ + l 0 (~)
2 + 2 o (o)
2 ~ 4 ~ (lO)
8 + 0.5 0 (0)
B ~ l 0 ()
~0 Q ~ 2 0 (0)
8 + 4 0 (lO)
Lolium Perenne
8 0
VII . l 20
2 60
I + VII B + l 70 (2~)
8 ~ 2 70 (S0)
W093/0~655 211 9~ ~ PCT/EP92/02185
~able G-
~ixtures with I with chlorsuI~uron (VIII)
Component Rate Herbicidal E (according
(g/ha~ activity (~) to Colby)
_ _ _ _ _ . _
Wheat
I 4 0
VIII 0.5 0
I + VIII 4 1 0.5 0 ()
10 Viola arvensis
I 4 80
VIII 0.5 0
I + VIII 4 ~ 0.5 90 (80)
Veronica persica
I 4 70
. VIII 0~5 20
I + VIII 4 + 0.5 80 (76)
Stellaria media
I 4 20
VIII 0.5 70
Component Rate HerbicidalE (according
(glha) activity (%~to Colby)
I + VIII 4 + 0.5 9S (76)
- WO 93/0565~ 21 19 6 a ~ P~/EP92tO~185
Tabl~ R
Mixtures of I with fluroxypyr (IX)
CoDIponent R te Herbicidal E ( according
(~/ha) activity (%) to Colby)
_
Wheat
o
2 o
IX 12.5
~o 25 o
0
I + IX 1 + ï2.5 o (o)
l ~ 25 o (o)
1 + 50 o (O)
2 ~ 12.5 o (o)
2 + 25 o (o)
2 ~ 50 0 (O)
9~ha~Q~
` 2 ~o
IX 25 60
I + IX 1 + 50 95 (87)
2 ~ 25 85 (76)
~-- W093/056~5 28 2.119~
~, .
Component Rate Herbicidal E (according
(g/ha~ activity (~) to Colby)
Matricaria chamomilla
I 1 70
IX 12.5 20
25 30
, .,
I + IX 1 ~ 12.5 95 (76)
1 + 25
Viola sp~.
I 1 80
IX 2S 20
I + IX 1 * 2S 95 (8~)
Stellari~ media
I . 1 50
IX 12.5 75
I + IX 1 + 12.5 95 ~88)
.
:
, :
~i: . ` `
.
-~W093/0~655 2g2 L3l9~ PCr/~:Yg2/02185
T~ble I
Mixtu~es of I with pendimethalin (X)
ComponentRate ~Ierbicid~ 1 E ( according
(g/ha) activity (%) to Colby)
_ _ _ _
~heat
o
2 0
X 400 o
800 0
I + X~ ~ 400 0 ()
1 + 800 0 to)
2 + 400 5 ~0)
2 + ~00 5 (0)
Galium a~arine
3 0
X 400 40
I + X 1 ~ 800 75 ~58)
Viola sP~.
8 0
X 400 3~
I + X 1 + 400 98 (86)
--~W093/056~ PCT/EP92/02185
- 30
....
Compone~t Rate Herbicidal E ~according
tg/ha) activity (%) to Colby)
Veronica ~ersica
I 2 60
X 800 40
I + X 2 ~ 800 90 (76)
. .
Setaria ~iridis
I 2 lO
X 800 50
I + X2 ~ 800 70 t~4)
2 1 ~ 5
WO 93/0565~ PCr/EP92/02185
3/1
..
Table J
~ixtures of I with isoxaben (XI)
Component Rate Her~icidalE ( according
(g/ha3 ~ctivity (%)to Colby1
Wheat
o
2 0
XI 125 o
250 o
500 o
I + XI 1 +125 0 (o3
1 ~250 o (0)
1 +500 0 (0)
2 +125 o t~
2 1250 5 (o)
2 ^t500 5 t )
Galium a~arirle
2 40
4 60
XI 250 o
500 10 . :
XI 2 ~5 0 0 7 0 ( 4 6 ) ~:
~ + 2S0 70 (60) ;
4 1500 80 (64) :
`WO 93/05655 2 1 19 6 ~ 5 PCI/EP92/02185
.. ~
,.
Coloiponent Rate Herbicidal E ( ac:cording
(g/ha) activity (%) to Colby)
Viola _s~.
I 1 70
XI 125 20
I + XI 1 + 125 95 (76)
able ~t
Mixtures o~ I with cyanazine (XII)
Component Rate Herbicidal E ( accordiny
(g/ha) activity (~) to C~lby~
~Saize
2 0
4 :
XII 12.5 0 ~ -
0 : ~
100 0 ~ `
.
I + XII 2 + 12.5 0 (o)
2 ~ 25 0 ()
2 + 5 0 o ( 0 )
2 + 100 0 ( 0 )
4 + 12.5 ()
4 + 25 0 (o)
4 + 50 0 ( 0)
4 + 100 ()
-^WO 93/05655 21~ 9 ~ ~ ~ PCI/EP92/02185
33
Component Rat~ Herbicidal E ( according
(g/ha) activity (%) t~ Col~y)
Galium ap_rire
I 4. 40
XII 50 40
.
I + XII 4 + 50 70 (64)
Viola sPP.'
I 4 50
XII 25 40
I + XII 4 + 25 95 (70)
e~onica ~e~sica
4 50
XII 12 . 5 50
I t~ XII 4 +12 . 5 90 (70)
Setaria viridis
2 lO
XII lO0 85
I + XII 2 + 100 98 (87)
- 21196~
~W093/~655 PCT/EP92/02185
~a~ .
Mixtur~s of I with dicamba (XIII)
Component Rate Her~icidalE (according
(g/ha) activity (~) to Colby)
__ _ _ _ ,
aize and Wheat
I l 0
2 0
XIII 12.5 0
0
I + XIII 1 + 12.5 0(0)
1 ~ 25
2 ~ 12.5 0
2 + 25 0(0) ~ ~
~atricaXia chamomilla ~ :-
I 1 70
2 80
XIII 12.5 20
I + XIII 1 ~ 12.5 90(76) ~:
1 + 25 96(79)
2 ~ 12.5 99(84) :
2 + 25 99(B6)
::
Viola sp~
I 2 80
XIII 12.5 30
I + XIII 2 t 12.5 98(86)
-~W093/~655 2 ~ 3~ PCT/EP92/02185
Component Rate ~erbicidal E (according
(g/ha) activity (S) to Colby)
~tellaria media
I l lO
XIII 25 60
I + XIIIl ~ 25 80 (6~)
~able
Mixtures of I with ethofumesate (XI~
lO Component Rate Herbicidal E (according
(g/ha) activity (%) to Colby)
_ _ _ _ _ ~
Maize
I l 0
2 .
XIV 50 0
I + XIV l ~ 50 5 (oj
2 + 50 5 (o)
Galium aParine
I 2 30
XIV 50 50
I ~ XIV.2 + 50 70 (65)
- ~WO 93/0565i5 PCr/EP92/02185
3 ~2 ~
Component Rate Herbicidal E ( according
(g/ha)activity (~c) to Colby~
.
M3i~ricaria chamomil~
S I l 20
XIV 5~ ~0
I ~ XIV 1 ~50 70 (36)
Viola sPP .
7 0 :
':
XIV 50 o
XIV 1 +50 80 (70
~able N
ISixtures of I with 2, 4-D- tNa) (XV)
Component Rate ~Ier~icidal E (according
(g/ha) activity (%) to Colby)
BarleY
4 0
8 0 ~:
XV 250 ~ :
500 0
1~00 0
~: :
211~6~
WO 93/056~5 PCI/EP92/02185
3~
Component Rate Herbicidal E (~ce:ording
(g/ha) activity (%~ to Colby)
_
I ~ XV 4 1250 o (o)
4 ~500 o (0)
4 + 1000 o (o
8 ~ 250 o
8 1 500 o (0)
8 + 10~0
8 ~ 1000 o
Galium _a~2arine
4 6 0
XV 500 0
+ XV 4 + 500 85 ( 60)
Stellaria media
4 50
8 50
'
XV 250 10
100~ 40
I + XV 4t 250 75 (55)
8 + 1000
21~6 ~
WOs3/05655 PCT/EP92/02185
~g
Mixtures of I with thifensulfuron-met~yl (XVI)
Compon~nt Rate ~erbicidal E (according
(g/ha) ~ctivity (%) to Colby)
_. _ _ _
S . WhQat and Barley
I l . 0
2 o
XVI 1 0
2 0
I + XVI 1 + 1 o (0)
l + 2 0 (0)
2 ~ l 0 (0)
2 + 2 0 (D)
Matricaria chamgmilla
lS I 2 50
XVI 1 60
::
I + XVI 2 + 1 90 (80)
Viola s~.
I l 50
XVI 2 20
I + XVI .1 + 2 80 (6~)
.. , . . ... .,.. ",,, ., . ... . .,.. , ... - i ; .. , - ,, .-; ., , ~ ~, ;
211~6;~r3
. WO 93/0565~ PCI/EP9~/02185
3~
Component Rate ~lerbicidal E ( according
(g/ha) activity (~6) to Colby)
,
Stellaria medj,a
I 1 20
XVI 2 6 0
I ~ XVI 1 + 2 80 (68)
Mixtures of I with imazamethabenz (XVII)
Component Rate }Ierbicidal E ( according
(ç~/ha) activity (9~) to Colby~ -
Wheat and BarleY
I 2
4 ~ :
8 0
XVII 100 0
400 o
I ~ XVII 2 + lO0 o ~o)
4 * 100 0 (o)
8 + 100 0 (~)
2 ~ 400 0 (o3
4 ~ 400 0 (0)
8 + 400 0 (0)
6 5 ~
` `WO 93/05655 PCI~/EP92/02185
~lLo
Component Rate Her~icidal E ( according
(g/ha) ac:ti~ity (%) to Colby)
Ga1aum a~arine
S I 2 30
XVII 400 60
I + XVII 2 +400 80 (72)
Matr caria c:hamomilla
4 6 0
XVII 100 o -~
I + XVII 4 ~100 75 (60)
Viola s~P.
4 80
XVII 100 10
I ~ XVII4 + lO0 go (82)
Veronica Persi~a
2 40
XVII 400 80
I + XVII 2 +400 75 (58)
W093/0565~ PCT/EP92J02l85
... .
Component Rate Herbicidal E (according
(g/ha) activity (%) to Colby)
Stellaria media
I 8 40
XVII 400 0
I + XVII 8 + 400 80 (40)
able Q
Mixtures of I with di~lufenican (XVIII)
10 Component Rate Herbicidal E (according
(g/ha) ~ctivity (%) to Col~y)
~ _ , , ._ _
Wheat
I 1 0
8 0
XVIII 12.5 0
100 0
I + XVIII 1 + 12.5 0 (O)
I -~ 100 0 (0~
8 + 12.5 0 (o)
8 + 100 0 (0)
Galium aparine
I 1 5
XYIII 100 60
I + XVIII1 ~ 100 85 (62)
. ~
~ W093/0565~ PCT/EP92~02185
4~
Component Rate Herbicidal E (according
(g/ha) activity (%) to Colby)
Viola 50.
I 1 30
XVIII 12.5 50
I + XVIII1 + 12.5 80 (72)
Setaria viridis
I 8 20
XVIII 100 40
I + XVIII 8 + 100 70 (52)
~able R
Nixtures of I with methab~nzthiazuron (XIX)
Component Rate Herbicidal E (according
(g/h~) activity (%) to Colby)
.
Wheat
I 2 0
XIX 100 0
I + XIX 2 + 100 20
.
Veronica ~ersica
I 2 20
XIX 100 70
I + XIX 2 ~ 100 90 (76)
PCI /EP92/021 8
: ~`WO 93/05655
113
Mixtures of I with benfuresate (XX)
4 0
XX 50 o
I + XX 4 + 50 10 (o)
PolYqonum la~athifolium
4 90
XX 50 10
I + XX 4 + Sû 97 (91)
-- W093/05655 2 ~ ~ 9 ~ ~ ~ PCT/EP92/02185
abIQ T
Mixtures of I with amidosulfuron (XXI)
Component Rate ~erbicidalE (according
(g/ha) acti~ity (%) t~ Colby~
_ .
~heat
I l o
8 0
XXI 1 0
2 o
I + XXI1 ~ 1 o ~o)
l + 2
~ + 1 ~ (O)
8 ~ 2 0 ()
Galium aParine
I 8 70
XXI 1 lO
I + XXI8 + l 85 (73)
Polvqonum laPathifolium
I 1 55
XXI 1 0
2 0
I + XXIl + l 9o (S5)
l ~ 2 93 (55)
- WO 93/05655 ~ 1 ~ 9 ~ ~ ~ PCI/EP92/02185
lt5
... .
Component Rate Herbicidal E ( according
(g/ha) activity (~) to Colby)
Veronica ~ersica
I l 30
XXI 1 0
2 0
I + XXI 1 ~ 1 50 (30)
l + 2 70 (30)
