CA2119655A1 - Synergistic herbicidal compositions - Google Patents
Synergistic herbicidal compositionsInfo
- Publication number
- CA2119655A1 CA2119655A1 CA002119655A CA2119655A CA2119655A1 CA 2119655 A1 CA2119655 A1 CA 2119655A1 CA 002119655 A CA002119655 A CA 002119655A CA 2119655 A CA2119655 A CA 2119655A CA 2119655 A1 CA2119655 A1 CA 2119655A1
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- activity
- colby
- methyl
- herbicidal
- component rate
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The invention relates to a new herbicidal composition with synergistic activity which comprises, as active components, a mixture of 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one and another selective herbicide.
The invention relates to a new herbicidal composition with synergistic activity which comprises, as active components, a mixture of 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one and another selective herbicide.
Description
~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 ~
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 o 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 + 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 16 lO
III lO o ` 20 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 III 10 o lo 20 o + 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 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.
4 ~0 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 . 8 60 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 8 6~
III lO 0 2~ 0 o 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 ~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
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 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 lG 4 0 + 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 . 8 60 i IV 25 o 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~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 5 PCI/EP92/0~185 Component Rate Herbicidal E ( according ( g/ha ) acti vity ( % ~ tc~ Co lby ) Stellaria ~nedia IV 2~ lO
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) 6~ 21 179 ~ F~ 5 Pcr/EP92/o2l85 :~ 2.o P-~
~'~ Co~Qponent Rate Herbicidal E (according (g/ha) activity (%) to Colby) ___ _ _ _ .
Veronica ~ersica lOû 40 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 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 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 + 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 8 o 16 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 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 + 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 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 VII . l 20 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 VIII 0.5 0 I + VIII 4 1 0.5 0 () 10 Viola arvensis VIII 0.5 0 I + VIII 4 ~ 0.5 90 (80) Veronica persica . VIII 0~5 20 I + VIII 4 + 0.5 80 (76) Stellaria media 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 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 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 IX 12.5 20 , ., I + IX 1 ~ 12.5 95 (76) 1 + 25 Viola sp~.
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 X 400 o I + X~ ~ 400 0 () 1 + 800 0 to) 2 + 400 5 ~0) 2 + ~00 5 (0) Galium a~arine I + X 1 ~ 800 75 ~58) Viola sP~.
X 400 3~
I + X 1 + 400 98 (86) --~W093/056~ PCT/EP92/02185 ....
Compone~t Rate Herbicidal E ~according tg/ha) activity (%) to Colby) Veronica ~ersica I + X 2 ~ 800 90 (76) . .
Setaria ~iridis I 2 lO
I + X2 ~ 800 70 t~4) 2 1 ~ 5 WO 93/0565~ PCr/EP92/02185 ..
Table J
~ixtures of I with isoxaben (XI) Component Rate Her~icidalE ( according (g/ha3 ~ctivity (%)to Colby1 Wheat o 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 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 + 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 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 Component Rat~ Herbicidal E ( according (g/ha) activity (%) t~ Col~y) Galium ap_rire I 4. 40 .
I + XII 4 + 50 70 (64) Viola sPP.' I + XII 4 + 25 95 (70) e~onica ~e~sica 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 XIII 12.5 0 I + XIII 1 + 12.5 0(0) 1 ~ 25 2 ~ 12.5 0 2 + 25 0(0) ~ ~
~atricaXia chamomilla ~ :-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~
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
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 .
I + XIV l ~ 50 5 (oj 2 + 50 5 (o) Galium aParine 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 .
~ .
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 ~
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 o 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 + 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 16 lO
III lO o ` 20 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 III 10 o lo 20 o + 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 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.
4 ~0 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 . 8 60 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 8 6~
III lO 0 2~ 0 o 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 ~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
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 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 lG 4 0 + 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 . 8 60 i IV 25 o 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~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 5 PCI/EP92/0~185 Component Rate Herbicidal E ( according ( g/ha ) acti vity ( % ~ tc~ Co lby ) Stellaria ~nedia IV 2~ lO
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) 6~ 21 179 ~ F~ 5 Pcr/EP92/o2l85 :~ 2.o P-~
~'~ Co~Qponent Rate Herbicidal E (according (g/ha) activity (%) to Colby) ___ _ _ _ .
Veronica ~ersica lOû 40 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 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 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 + 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 8 o 16 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 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 + 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 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 VII . l 20 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 VIII 0.5 0 I + VIII 4 1 0.5 0 () 10 Viola arvensis VIII 0.5 0 I + VIII 4 ~ 0.5 90 (80) Veronica persica . VIII 0~5 20 I + VIII 4 + 0.5 80 (76) Stellaria media 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 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 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 IX 12.5 20 , ., I + IX 1 ~ 12.5 95 (76) 1 + 25 Viola sp~.
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 X 400 o I + X~ ~ 400 0 () 1 + 800 0 to) 2 + 400 5 ~0) 2 + ~00 5 (0) Galium a~arine I + X 1 ~ 800 75 ~58) Viola sP~.
X 400 3~
I + X 1 + 400 98 (86) --~W093/056~ PCT/EP92/02185 ....
Compone~t Rate Herbicidal E ~according tg/ha) activity (%) to Colby) Veronica ~ersica I + X 2 ~ 800 90 (76) . .
Setaria ~iridis I 2 lO
I + X2 ~ 800 70 t~4) 2 1 ~ 5 WO 93/0565~ PCr/EP92/02185 ..
Table J
~ixtures of I with isoxaben (XI) Component Rate Her~icidalE ( according (g/ha3 ~ctivity (%)to Colby1 Wheat o 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 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 + 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 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 Component Rat~ Herbicidal E ( according (g/ha) activity (%) t~ Col~y) Galium ap_rire I 4. 40 .
I + XII 4 + 50 70 (64) Viola sPP.' I + XII 4 + 25 95 (70) e~onica ~e~sica 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 XIII 12.5 0 I + XIII 1 + 12.5 0(0) 1 ~ 25 2 ~ 12.5 0 2 + 25 0(0) ~ ~
~atricaXia chamomilla ~ :-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~
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
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 .
I + XIV l ~ 50 5 (oj 2 + 50 5 (o) Galium aParine 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
':
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
8 0 ~:
XV 250 ~ :
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 + XV 4 + 500 85 ( 60) Stellaria media ' 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 I + XVI 1 + 1 o (0) l + 2 0 (0) 2 ~ l 0 (0) 2 + 2 0 (D) Matricaria chamgmilla lS I 2 50 ::
I + XVI 2 + 1 90 (80) Viola s~.
I l 50 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 ~ 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
4 ~ :
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 I + XVII 2 +400 80 (72) Matr caria c:hamomilla XVII 100 o -~
I + XVII 4 ~100 75 (60) Viola s~P.
I ~ XVII4 + lO0 go (82) Veronica Persi~a I + XVII 2 +400 75 (58) W093/0565~ PCT/EP92J02l85 ... .
Component Rate Herbicidal E (according (g/ha) activity (%) to Colby) Stellaria media 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 XVIII 12.5 0 I + XVIII 1 + 12.5 0 (O) I -~ 100 0 (0~
8 + 12.5 0 (o) 8 + 100 0 (0) Galium aparine I + XVIII1 ~ 100 85 (62) . ~
~ W093/0565~ PCT/EP92~02185 4~
Component Rate Herbicidal E (according (g/ha) activity (%) to Colby) Viola 50.
XVIII 12.5 50 I + XVIII1 + 12.5 80 (72) Setaria viridis 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 + XIX 2 + 100 20 .
Veronica ~ersica I + XIX 2 ~ 100 90 (76) : ~`WO 93/05655 Mixtures of I with benfuresate (XX) XX 50 o I + XX 4 + 50 10 (o) PolYqonum la~athifolium 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 2 o I + XXI1 ~ 1 o ~o) l + 2 ~ + 1 ~ (O) 8 ~ 2 0 () Galium aParine XXI 1 lO
I + XXI8 + l 85 (73) Polvqonum laPathifolium 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 I + XXI 1 ~ 1 50 (30) l + 2 70 (30)
XV 250 ~ :
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 + XV 4 + 500 85 ( 60) Stellaria media ' 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 I + XVI 1 + 1 o (0) l + 2 0 (0) 2 ~ l 0 (0) 2 + 2 0 (D) Matricaria chamgmilla lS I 2 50 ::
I + XVI 2 + 1 90 (80) Viola s~.
I l 50 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 ~ 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
4 ~ :
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 I + XVII 2 +400 80 (72) Matr caria c:hamomilla XVII 100 o -~
I + XVII 4 ~100 75 (60) Viola s~P.
I ~ XVII4 + lO0 go (82) Veronica Persi~a I + XVII 2 +400 75 (58) W093/0565~ PCT/EP92J02l85 ... .
Component Rate Herbicidal E (according (g/ha) activity (%) to Colby) Stellaria media 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 XVIII 12.5 0 I + XVIII 1 + 12.5 0 (O) I -~ 100 0 (0~
8 + 12.5 0 (o) 8 + 100 0 (0) Galium aparine I + XVIII1 ~ 100 85 (62) . ~
~ W093/0565~ PCT/EP92~02185 4~
Component Rate Herbicidal E (according (g/ha) activity (%) to Colby) Viola 50.
XVIII 12.5 50 I + XVIII1 + 12.5 80 (72) Setaria viridis 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 + XIX 2 + 100 20 .
Veronica ~ersica I + XIX 2 ~ 100 90 (76) : ~`WO 93/05655 Mixtures of I with benfuresate (XX) XX 50 o I + XX 4 + 50 10 (o) PolYqonum la~athifolium 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 2 o I + XXI1 ~ 1 o ~o) l + 2 ~ + 1 ~ (O) 8 ~ 2 0 () Galium aParine XXI 1 lO
I + XXI8 + l 85 (73) Polvqonum laPathifolium 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 I + XXI 1 ~ 1 50 (30) l + 2 70 (30)
Claims (3)
1. A herbicidal composition which comprises, as active components, a mixture of 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol-3-yliderlimino)-7-fluoro-4-(2-propynyl) 2H-1,4-benzoxazin-3(4H)-one and another selective herbicide of the group cyanazine, ioxynil, isoproturon, methabenzthiazuron, bifenox, chlorsulfuron, metsulfuron-methyl, pendimethalin, thifensulfuron-methyl, isoxaben, imazamethabenz, triasulfuron, amidosulfuron, ethofumesate, diflufenican, tribenuron-methyl, mecoprop, 2,4-D, benzolin-ethyl, dicamba or fluroxypyr.
2. A composition according to claims 1 in which the weight ratio of the mixture components is between 1: 50 and 50: 1.
3. ~ method of combating weed which comprises applying post emergently a composition as claimed in any one of the preceding claims.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4132089A DE4132089A1 (en) | 1991-09-23 | 1991-09-23 | HERBICIDES WITH SYNERGISTIC EFFECT |
| DEP4132089.1 | 1991-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2119655A1 true CA2119655A1 (en) | 1993-04-01 |
Family
ID=6441577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002119655A Abandoned CA2119655A1 (en) | 1991-09-23 | 1992-09-21 | Synergistic herbicidal compositions |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0605533A1 (en) |
| JP (1) | JPH06510775A (en) |
| CN (1) | CN1071048A (en) |
| AU (1) | AU652481B2 (en) |
| BG (1) | BG98672A (en) |
| BR (1) | BR9206527A (en) |
| CA (1) | CA2119655A1 (en) |
| CZ (1) | CZ68094A3 (en) |
| DE (1) | DE4132089A1 (en) |
| FI (1) | FI941330A0 (en) |
| HU (1) | HUT67942A (en) |
| IL (1) | IL102870A0 (en) |
| MA (1) | MA22653A1 (en) |
| MX (1) | MX9205362A (en) |
| PT (1) | PT100886A (en) |
| SK (1) | SK33694A3 (en) |
| TR (1) | TR26286A (en) |
| WO (1) | WO1993005655A1 (en) |
| YU (1) | YU86292A (en) |
| ZA (1) | ZA927278B (en) |
| ZW (1) | ZW14892A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994018836A1 (en) * | 1993-02-17 | 1994-09-01 | Schering Aktiengesellschaft | Synergistic herbicidal composition on the basis of thidiazimin |
| US5748396A (en) * | 1995-11-13 | 1998-05-05 | Seagate Technology, Inc. | Arrangement and method for optimizing the recorded signal to noise ratio in contact recording systems |
| WO2003055310A1 (en) * | 2001-12-25 | 2003-07-10 | Nihon Nohyaku Co., Ltd. | Herbicidal compositions and method of using the same |
| CN106386813B (en) * | 2016-08-31 | 2018-10-16 | 四川利尔作物科学有限公司 | Herbicidal combinations and its application |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812161A (en) * | 1984-08-08 | 1989-03-14 | Nippon Soda Co., Ltd. | Thia (oxa) diazole derivatives |
| DE3734745A1 (en) * | 1987-10-09 | 1989-04-20 | Schering Ag | TETRAHYDROPYRROLO (2,1-C) (1,2,4) -THIADIAZOL-3-YLIDENIMINOBENZOXAZINONE AND OTHER HETEROCYCLICALLY SUBSTITUTED AZOLES AND AZINES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS AGENTS WITH HERBICIDES |
-
1991
- 1991-09-23 DE DE4132089A patent/DE4132089A1/en not_active Withdrawn
-
1992
- 1992-08-19 IL IL102870A patent/IL102870A0/en unknown
- 1992-09-10 TR TR92/0863A patent/TR26286A/en unknown
- 1992-09-21 WO PCT/EP1992/002185 patent/WO1993005655A1/en not_active Application Discontinuation
- 1992-09-21 SK SK336-94A patent/SK33694A3/en unknown
- 1992-09-21 CZ CS94680A patent/CZ68094A3/en unknown
- 1992-09-21 HU HU9400825A patent/HUT67942A/en unknown
- 1992-09-21 EP EP92919951A patent/EP0605533A1/en not_active Withdrawn
- 1992-09-21 CA CA002119655A patent/CA2119655A1/en not_active Abandoned
- 1992-09-21 AU AU25891/92A patent/AU652481B2/en not_active Ceased
- 1992-09-21 BR BR9206527A patent/BR9206527A/en not_active Application Discontinuation
- 1992-09-21 MA MA22944A patent/MA22653A1/en unknown
- 1992-09-21 JP JP5505798A patent/JPH06510775A/en active Pending
- 1992-09-22 ZW ZW148/92A patent/ZW14892A1/en unknown
- 1992-09-22 PT PT100886A patent/PT100886A/en not_active Application Discontinuation
- 1992-09-22 MX MX9205362A patent/MX9205362A/en unknown
- 1992-09-22 YU YU86292A patent/YU86292A/en unknown
- 1992-09-23 CN CN92111158A patent/CN1071048A/en active Pending
- 1992-09-23 ZA ZA927278A patent/ZA927278B/en unknown
-
1994
- 1994-03-21 BG BG98672A patent/BG98672A/en unknown
- 1994-03-22 FI FI941330A patent/FI941330A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT100886A (en) | 1994-01-31 |
| CN1071048A (en) | 1993-04-21 |
| FI941330A (en) | 1994-03-22 |
| DE4132089A1 (en) | 1993-03-25 |
| AU2589192A (en) | 1993-04-27 |
| BG98672A (en) | 1995-05-31 |
| AU652481B2 (en) | 1994-08-25 |
| MX9205362A (en) | 1993-05-01 |
| ZW14892A1 (en) | 1993-05-12 |
| JPH06510775A (en) | 1994-12-01 |
| HU9400825D0 (en) | 1994-06-28 |
| HUT67942A (en) | 1995-05-29 |
| WO1993005655A1 (en) | 1993-04-01 |
| YU86292A (en) | 1995-10-03 |
| ZA927278B (en) | 1993-03-22 |
| SK33694A3 (en) | 1994-08-10 |
| BR9206527A (en) | 1995-11-07 |
| TR26286A (en) | 1995-02-15 |
| CZ68094A3 (en) | 1994-12-15 |
| IL102870A0 (en) | 1993-01-31 |
| MA22653A1 (en) | 1993-04-01 |
| FI941330A0 (en) | 1994-03-22 |
| EP0605533A1 (en) | 1994-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |