CA2122898A1 - Synergistic herbicidal compositions - Google Patents
Synergistic herbicidal compositionsInfo
- Publication number
- CA2122898A1 CA2122898A1 CA002122898A CA2122898A CA2122898A1 CA 2122898 A1 CA2122898 A1 CA 2122898A1 CA 002122898 A CA002122898 A CA 002122898A CA 2122898 A CA2122898 A CA 2122898A CA 2122898 A1 CA2122898 A1 CA 2122898A1
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- activity
- colby
- xxiii
- herbicidal
- 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
There is described new herbicidal compositions with synergistic activity which comprises a mixture of 2-[7-fluoro-3, 4-dihydro-3-oxo-4-(2-propynyl)-2H-1, 4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin-1, 3-one and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D (V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaquin (XXII) and imazethapyr (XXIII).
There is described new herbicidal compositions with synergistic activity which comprises a mixture of 2-[7-fluoro-3, 4-dihydro-3-oxo-4-(2-propynyl)-2H-1, 4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin-1, 3-one and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D (V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaquin (XXII) and imazethapyr (XXIII).
Description
O.~(.`H~ ?, ~_~;,,:__ ,_ ,_ ~I`J ;~u ~ U 'IJ;~ tlV ~`J ';lV~t~rl:>~
_ _ _ _ _ _ ~, . _ _ . _ _ _ _ _ _ _ _ P~T/EP 92102535 212289~
~9 ~his inv~ntion relate~ ~o ~ new herbicidal co~posltlo~
having syn~rgistic ~ctivity compr~ing ~ ~ixtur~ o~
S 2-[~-~luoro-3-oxo-4-~2-prupynyl)-3~4-dlhy~ro-2H-1,4-benzoxaZin-6-yl]p~rhydroi~idaZo~,5-a]pyrldine~
~,3-dione and anoth~r ~ela~tivu ~erbicld~ and ~ts ~ or comh~ting ueed~ in cropa.
: , The ~erbicid~l acti~ity o~ 2-t1-~luoro 3-oxo 4-(2-propynyl)-3,4-di~ydro-2H-1,4-bonzoxa3in-6-yl~perhydroi~ida~o~,5 a~pyrldi~ -d~one iB already known (~P 311 135). This compound h~s ~he ~ollowing cha~lcal ~truct~re (I) oJ~;~ N /~\ 1' ''I ( I
20 CH~-C~
O
It has now been found that hsrbic~dal co~o~itions which compri~, as active co~pnnents, ~ ~ixtu~e 2-[7-rluor~-3-oxo-~-(2-propynyl)~3~ ihy~o-2H-1,4-benzoxa2in-6-yl~perhydroimldazo~1,S-a~pyridin -1~3-dlone (I) and a herbicide ~elec~ed fro~ the g~oup ' consi~ting of glyphosate (II), sul~o~eturon-metbyl tXII), i~azapy~ (~V), 2,4-D ~Y), dic~ba ~VI), dlu~on lVII), oxyfluor~en ~VIXI), glu~osinat~am~on~u~ (IX), a~itr~le ~x) and 3ethoxydi~ ~XI) a3 w~ll as ~etribu~1~ (XII~
linuron ~XIII), acifluorfa~ ~IV), lacto~n (X~
~omesa~en ~X~I), pendimeth~lin ~XVII~, al~chlor (X~I~I3, metolachlor (XIX), tri~luralin (XX), chlorimuron-~thyl (XXI), i~azaquin .
: . ' .. ~.
-~1093/08689 X~ ~ 2 ~ ~ ~ PCTIEP92/OZ535 (XXII) and imazethapyr (XXIII), broaden the spectrum of weeds that can be controlled and show an increase in herbicidal activity in comparison with the individual components without losing the selectivity properties in agricultural crops.
Glyphoc~te is the common name for N-(phosphonomethyl)~
glycine;
sulfometuron-methyl is the common name for methyl 10 2-(4,5-dimethylpyridin-2-ylcarbamoylsulfamoyl3benzoate;
imazapyr is the common name for 2-t4-isopropyl-4 methyl-5-oxo-2-imidazolin-2-yl)-nicotinic acid;
2,4-D is the common name for 2-(4-chloro-2-methyl-phenoxy)acetic acid;
dicamba is the common name for 3,6 dichloro-2-methoxy-benzoic acid;
diuron is the common name ~or 3-(3,4~dichlorophenyl)~
dimethylurea;
oxyfluor~en is the common name for 2-chloro-a,~,~-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether;
glufosinate ammonium is the common name for ammonium 4-thydroxy(methyl)phosphinoyl]-DL-homoalaninate;
amitrole is the common name for lH-1,2,4-triazol-3-ylamine;
sethoxydim is the common name for (+)-(EZ)-2-(1-ethoxyiminobutyl)-s-~2-(ethylthio)propyl]-3-hydr cyclohex-2-enone;
metribuzin is the common name for 4-amino-6-tert.-butyl-4,5-dihydro-3 methylthio-1,2,4-triazin-5-one;
linuron is the common name for 3-(3,4-dichlorophenyl~-l-methoxy-l methylurea;
acifluorfen is the common name for 5-[2-chloro-4-(trifluoromethyl)phenoXy]-2-nitrobenzoic acid; ~ :
lactofen is the common name for (~)-2-ethoxy-1-ethyl-2-oxoethyl 5-[chloro-4-(trifluoromethyl)phenoxy~
_ _ _ _ _ _ ~, . _ _ . _ _ _ _ _ _ _ _ P~T/EP 92102535 212289~
~9 ~his inv~ntion relate~ ~o ~ new herbicidal co~posltlo~
having syn~rgistic ~ctivity compr~ing ~ ~ixtur~ o~
S 2-[~-~luoro-3-oxo-4-~2-prupynyl)-3~4-dlhy~ro-2H-1,4-benzoxaZin-6-yl]p~rhydroi~idaZo~,5-a]pyrldine~
~,3-dione and anoth~r ~ela~tivu ~erbicld~ and ~ts ~ or comh~ting ueed~ in cropa.
: , The ~erbicid~l acti~ity o~ 2-t1-~luoro 3-oxo 4-(2-propynyl)-3,4-di~ydro-2H-1,4-bonzoxa3in-6-yl~perhydroi~ida~o~,5 a~pyrldi~ -d~one iB already known (~P 311 135). This compound h~s ~he ~ollowing cha~lcal ~truct~re (I) oJ~;~ N /~\ 1' ''I ( I
20 CH~-C~
O
It has now been found that hsrbic~dal co~o~itions which compri~, as active co~pnnents, ~ ~ixtu~e 2-[7-rluor~-3-oxo-~-(2-propynyl)~3~ ihy~o-2H-1,4-benzoxa2in-6-yl~perhydroimldazo~1,S-a~pyridin -1~3-dlone (I) and a herbicide ~elec~ed fro~ the g~oup ' consi~ting of glyphosate (II), sul~o~eturon-metbyl tXII), i~azapy~ (~V), 2,4-D ~Y), dic~ba ~VI), dlu~on lVII), oxyfluor~en ~VIXI), glu~osinat~am~on~u~ (IX), a~itr~le ~x) and 3ethoxydi~ ~XI) a3 w~ll as ~etribu~1~ (XII~
linuron ~XIII), acifluorfa~ ~IV), lacto~n (X~
~omesa~en ~X~I), pendimeth~lin ~XVII~, al~chlor (X~I~I3, metolachlor (XIX), tri~luralin (XX), chlorimuron-~thyl (XXI), i~azaquin .
: . ' .. ~.
-~1093/08689 X~ ~ 2 ~ ~ ~ PCTIEP92/OZ535 (XXII) and imazethapyr (XXIII), broaden the spectrum of weeds that can be controlled and show an increase in herbicidal activity in comparison with the individual components without losing the selectivity properties in agricultural crops.
Glyphoc~te is the common name for N-(phosphonomethyl)~
glycine;
sulfometuron-methyl is the common name for methyl 10 2-(4,5-dimethylpyridin-2-ylcarbamoylsulfamoyl3benzoate;
imazapyr is the common name for 2-t4-isopropyl-4 methyl-5-oxo-2-imidazolin-2-yl)-nicotinic acid;
2,4-D is the common name for 2-(4-chloro-2-methyl-phenoxy)acetic acid;
dicamba is the common name for 3,6 dichloro-2-methoxy-benzoic acid;
diuron is the common name ~or 3-(3,4~dichlorophenyl)~
dimethylurea;
oxyfluor~en is the common name for 2-chloro-a,~,~-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether;
glufosinate ammonium is the common name for ammonium 4-thydroxy(methyl)phosphinoyl]-DL-homoalaninate;
amitrole is the common name for lH-1,2,4-triazol-3-ylamine;
sethoxydim is the common name for (+)-(EZ)-2-(1-ethoxyiminobutyl)-s-~2-(ethylthio)propyl]-3-hydr cyclohex-2-enone;
metribuzin is the common name for 4-amino-6-tert.-butyl-4,5-dihydro-3 methylthio-1,2,4-triazin-5-one;
linuron is the common name for 3-(3,4-dichlorophenyl~-l-methoxy-l methylurea;
acifluorfen is the common name for 5-[2-chloro-4-(trifluoromethyl)phenoXy]-2-nitrobenzoic acid; ~ :
lactofen is the common name for (~)-2-ethoxy-1-ethyl-2-oxoethyl 5-[chloro-4-(trifluoromethyl)phenoxy~
3~
` ~ 2~2289~
-~093/08689 PCT/EP~2/OZS35 2-nitrobenzoate;
fomesafen is the common name for 5-[2-chloro-4-(trifluoromethyl)phenoXY]~N-(methylsulfonyl)-2-nitro-benzamide;
pendimethalin is the comMon name for N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline;
alachlor is the common name for 2-chloro-2',6'-diethyl-N-methoxymethylacetanilide;
metolachlor is the common name for 2-chloro-6'~ethyl-2'-methyl-N-(2-methoxy-1-methylethyl)acetanilide;
trifluralin is the common name for 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline;
chlorimuron-ethyl is the common name for ethyl 2-(4-chloro-6-methoxyPyrimidin-2-ylcarbamoylsulfamoyl)-lS benzoate;
imazaquin is the common name for (+)-2-~4,5-dihydro-4-methyl-4~ methylethyl)-~-oXQ-lH-imidazole-2-yl]-5-ethyl-3-pyridinecarboxylic acid; and imazethapyr is the common name for (+)-2-[4,5-dihydro-20 4-methyl-4-(1-methyleth~ 5-oxo-lH-2-yl]-3-quinoline carboxylic acid.
All these herbicides axe described in the "Pesticide Manual", ninth edition, 1991, published by the British Crop Protection Council, London.
::
The combinations of the invention are suitable for the control of important annual and perennial weeds, especially in plantation and permanent crops, such as for example in fruit, wine, citrus, forests and ornamental cultivations, in arable land outside the vegetation time (for example stubble treatment), as well as in the industrial area including highways and railways. Further uses are for the control of important weeds in a range of 3S crops, such as for example soya beans.
; .
- -~Y~093J0~89 2 ~ 2 2 8 9 8 PCT/EP92/02535 The combination of active ingredients of the invention can used for 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 Chrysanthemum.
.
MonocotyledonoUs weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron (= Elymus), Sagittaria, Monocharia, Fimbristylis, Eleocharis, Ischaemum and Apera.
The combinations of I with II-XI can be applied pre-emergently, and the combinations of I with XII-XXIII can be applied post-emergently. The rate of use lies between 0.001 and 5 kg/ha of the mixture, depending on the use. By using the mixtures for control of weeds the amount of herbicide needed can be generally reduced.
The weight ratio of component I) to the other component is generally between 50:1 and 1:100.
The compositions of the invention can also be used in admixture with other active agents for example other 30 plant-protection agents or pesticides, depending on the -particular need.
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 ~093/0868g 212 2 ~ 9 8 PCT/EP92/02535 additives may allow a decrease in the dose.
The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants.
Suitable li~uid carriers are, ~or example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and other mineral-oil fractions and plant oils.
Suitable solid carriers include mineral earths, 2 Og.
bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
As surface-active agents there can be used for 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 benzenesulfonic 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 active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes V.~ X ~
~ ",. " ~ . r ' " ' "~
-~093/08689 212 ~ 8 '~ ~ PCT/EP92/02535 o~ approximately 100 to 1,O00 l/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
~he preparation of these f9rmulations can be carried out in known manner, for example by milling or mixing processes. Optionally, individual components can be mixed just before use for example by the so-called commonly used tank-mixing method.
The following Examples illustrate the use of compositions of the invention.
The calculation of 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~ In this the following formula was used:
XY
E = X ~ Y ~
in which X = the herbicidal activity (%) of substance at a rate of p g/ha.
Y = the herbicidal activity (%) of substance B
at a rate of q ylha., and E = the expected additive activity of the herbicide (%) of the substances A + B at a rate of p + q g/ha.
If the observed value is greater than the value of E
calculated according to Colby, the combination shows synergistic activity.
-~093~08689 2 12 2 8 9 8 PCT/EP~2/02535 Ex~eFiments In a greenhouse the plant species shown in tables A-K were treated post-emergently with the components at the stated rates. The compositionS were diluted with 500 litres of water and sprayed evenly over the plants. ~wo weeks after treat~ent the herbicidal effect was evaluated.
Tiab 1 e 2~
Mixtures of I with glyphosate (II) Rate Herbicidal E (according : 10(g/ha) activity (%) to Colby) _ Amaranthus retrofle~us -~
II 50 5 :
S ~ 50 85 ~81) ' Cv~erus esculentus ~ .
I ~ 40 ~ : :
II ~ao s ~3) ~ ~:
' , '~
Elvmus re~ens I ~ :
II ~00 ~0 III ~ t~00 85 l70) s.~,i ;,~,l,.,..: :."~",,-:,,"",,~",~ ",~,,,"", ~'YO93/08689 2 12 2 8 9 8 PCT/EP92/02535 .. . .
~able B
Mixtures of I with sul~ometuron-methyl (III) Rate Herbicidal E (according (g/ha) activity (~) to Colby) - -Component Rate .HerbicidalE (according ~g/ha) activity (~)to Colby) 9-achiaria mutica a lo III 2 so I ~ III 8 ~ Z 75 ~59) Ses~ania exale~
~, 20 2 75 ( 68 ) :: ~
9romu~
o I ~ III 8 ~ ~ 75 (68) :
.s ", . ~
~--~093/08689 PCT/EP92/02535 212289~
Table C
Mixtures of I with imazapyr (IV) Rate HerbicidalE (according (g/ha) activity (~to Colby) . _ _ Setaria viridis I ~ IV 1 2 go ~B6) Sor~hum haleDense I ~ IV 8 ~ 1 90 ~76) CvDerus esculentus ~, 8 0 I V ~ 1 0 I ~ IV ~ ~ ~ 98 ~82 WO 93/08689 ;~ ~ 2 2 3 ;~ ~ PCI/EP92/02535 Table D
Mixtures of I with 2, 4-D (V) ~ate Herbicidal E (according (g/ha) activity ~%) to Colby) S ~
8idens Dilosa I ~ 60 V 100 o I ~ y s ~ 100 80 ~60) .~ ~ 200 85 ~6~) Sesbania exaltata ~ 0 I ~ V 5 ~ 100 go (~0) 8 ~ 100 98 ~aO) : .
, : Amarantb~s retroflex~
200 2a I ~ V 2 ~ 50 90 l73) 2 ~ 200 90 (76) W093/08689 2 12 2 ~ 9 8 PCT/EP92/02535 Table E
~ixtures of I with dicamba (VI) Rate Herbicidal ~ (according (g/ha) activity (%) to Colby) Sesbania exalt_ta : VI 25 70 I ~ YI 1 ~ 25 90 176) B id e n s P i ~s a ~ o ~ ~
I ~ VI 1 ~ 25 05 ~76 ~2~2~9~
Table F
~ixtures of I with diuron (VII) Rate Herbicidal E (according (g/ha) activity (%) to Colby) Sesbania exaltata I 0,5 0 2 30 ~: -YII 50 s I ~ VII 0,5 ~ 100 95 l80) 4 100 95 l80) 2 4 50 75 ~3~) ~ ~ 50 95 ~ 65 I ~ VII 2 ~ 25 85 l50) ~ ~ 25 99 ~65 8 ~ 25 100 ~80) CvDerus esculentus I 8 ~o I ~ VII 8 1 100 70 l~0) 8 ~ 200 ao l~3) Setaria viridis I ~ YII 1 ~ 100 97 ~72) ~WO 93/08689 PCI/EP~2/02~3~
21228g8 Table G
Mixtures of I with oxy~luorfen (VIII) ~ate Herbicidal E ( according (g/ha) activity (%) to Colby) S ~
Sesbania exaltata VIII 2 ~o I ~ VIII 1 ~ 2 70 (~9) 2 ~ 2 90 ~65) Amaranthus retroflexus .
VIII 2 ~0 .
I ~ VIII 1 ~ 2 98 S89~
-~ W093/08689 212 2 8 9 8 PCT/EP92/02535 able E
~ixtures of I with glu~osinate-ammonium (IX) ~ate Herbicidal E (according (y/ha) activity (%) to Colby) _ __ Setaria viridis I ~ 20 I ~ IX ~ ~ 80 80 (68) 6rachiaria mutica I ~ IX 8 ~ 80 95 ~36 Sorqhum t~aleoense IX ~0 0 I ~ IX8 ~ sn so 150) Sesbania exaltata I ~ IX 2 ~80 98 ~60 .~W0~3/08689 2 -1 2 2 ~ 3~ PC~/EP92/02535 Table I
Mixtures of I with amitrole (X) Rate Her~icidal E (according (g/ha)activity (%) to Colby) ~
Setaria viridis I ~ 20 I ~ X~ ~ 200 80 (68 Bracharia mutica I ~ 0 i ~ X~ ~ 200 70 l~0]
8 ~ 200 9S (33) ~ .
I ~ 70 X ~ ~ 50 a5 l76) Sesbania exaltata I ~ X 125 785 133) ` 2 ~ 25 90 153) 2 l 50 95 (65) ,...
W093t08689 PCT/EP92/0253~
2~22~9~
Table K
Mixture~ of I with sethoxydim (XI) Rate HerbicidalE (according (g/ha) activity (%)to Colby) 5 ~ , . _ _ _ Setaria viridis I ~ XI~ ~ lO0 98 ~73) .
Brac~iaria mutica I ~ XI 8 ~ 50 95 183) ,Bromus s~
I ~ XI 2 ~ 200 85 16~1 .W093/08689 2 12 2 8 ~ ~ PCT/EP92/02535 Ex~eriments In a gre~nhouse the plant species shown in tables L-~ were treated pre-emergently with the components at the stated rates. The compositionS were diluted with 500 litres of water and sprayed evenly over the soil. Two weeks after treatment the herbicidal effect was evaluated.
Table L
Mixtures of I with metribuzin (XI~) Rate Herbicidal ~ (according (g/ha) activity (%) to Colby) Soiabohne : ~:
XII 12,5 o O
I ~ XII~ 1 12,5 5 lO~
a ~ 12,5 s 1O~
~ ~ 50 o lO~ :
a ~ so s lo~
~ ~ ~oo s 15 8 ~ 100 10 ~5 IDomoea DurDurea I ~ XII8 I S0 70 l62 Amaranthus_retroflex~s I ~ 10 . XII S0 S0 I ~ XII ~ ~ 50 98 l55j ~ ~ 50 98 l55~ i :
~ ' ` 2~2289~
.W093~08689 PCT/EP92/02535 able M
Mixtures of I with linuron (XIII) Rate Herbicidal E (according (5/ha) activity (%) to Colby) Soiabohne a o XIII 100 o 200 o I ~ XIII2 ~ 100 o tn) 2 ~ 200 o tO) B ~ lOD 0 t6) . .
8 ~ 200 S ~5) Amaranthus retroflexus a 20 XIII l I ~ XIII 8 lOo 80 t201 PolYqonum laDathiflolium I ~ Xl I I 2 , 200 80 160 Setaria virid_5 8 ~0 XIII 100 o I ~ XIII 8~ 100 75 ~, :~
W093/0~89 212 2 8 9 g PCT/EP92/0253~
~able N
~ixtures of I wi~h acifluorfen (XIV) RateHerbicidal E taccording (g/ha)activity (%) ta Colby) S , _ _ _ _ Soiabohne I 2 o ~ 20 8 ~0 ~o 10 I I XIV 2 ~ 10 o 1 2 ~ 20 10 15 2 ~ ~0 0 l10) 0 ~20) 20 20 ~2~) ~ ~ 40 10 ~27) 8 ~ 10 20 ~0) 8 ~ 20 50 ~ ~ ~o 10 1~6) Ioomoea Dur~urQa XIV 10 o I ~ XIV8 1 10 85 (70) 8 ~ 20 95 (73~
. . .
Amaranthus retroflexus XIV ~0 30 I ~ XIV ~ ~ ~0 90 (58) :
Polvqon ~ LaDathifolium XlV 10 o I ~ XIV ~ ~ 10 95 l80) .~
W093/08689 2 12 2 8 9 o PCT/EP92/02535 Rate Herbicidal E (according (g/ha) - activity t%) to Colby) Sorqhum haleDense I ~ XIV 2~ 20 90 176) ~iqitaria ischaemum 2 10 I
I ~ XIV 2 ~ 20 75 (SSI
, ~ ~
.
WO 93/08689 2 ~ 2 2 8 9 ~ PCI/EP92/02535 ..
Table o Ni~tures of I with lactof en (XV) Rate Herbicidal F ( according (g/ha) activity (%) to Colby) Soiabo~ne o XY 20 o I ~ XV 1 l 20 2 ~ 20 ~ ~ 20 0 110) Amaranthus retroflexus ~0 XV 20 ~o I ~ XV 2 ~20 ~5 ~52 ~ ~20 90 (701 Po~vqonum-laDathiflolium 2 ~o 1 ~ XV 2 ~20 go ~, ;
~iqitaria ischaemum I ~ XV 1 ~20 90 ~ 50 ~ ,;
æ~22~9~
Ta~l~ P
Mixt~res of I wi~h fomesafen (XVI) Rate Herbicidal E (according (g/h~) activity (%) to Colby) S P i a bo h n e 2 o ~0 20 I ~ XVI 2 ~10 0 ~10) 2 ~ ~ 30 ~20) 2 ~80 20 ~20) 10 10 ~28) ~0 10 ~36) ~ ~80 20 ~36) 8 ~10 20 128) 8 ~~0 20 (36) 8 ~80 20 ~36) Jmp~moea DurDurea .
XYI ~0 20 ao ~o I I XVI 8 ~~0 90 168) 8 ~80 95 ~76) :
~.
Polvqonum laDathi~lolium ~, 75 : :
XV I 10 ~ 5 I ~ XYI 2 110 80 t8) ~ ~10 98 177 ) -~VO 93/û8689 PCI/EP92/02535 2:~22~8 Rate HerbicidalE (according ~/ha) activity (%) to Colby) .
Sorallym halepense I ~ XYI ~ ~ 10 85 ~55) Diqitaria ischaemum I ~ XVI ~ ~ 10 90 (65 ~-n ~
~W093/08689 2 ~ 2 2 ~ ~ ~ PCT/~P92/02535 able Q
~ixtures of I with pendimethalin (XVII) RateHerbicidal E (according (g/ha)~ctivity (%) to Colby) S ~
Soiabohne I 2 o O
. 8 0 XVII 25 o 200 o I ~ XVII 2 ~ 2S o 10) ~ ~ 25 0 10) 8 ~ 25 0 (0) 2 o 200 o 10) ~ ~ 200 o lO) 8 ~ 2~0 o ~0 Setaria viridis I 8 o I ~ XVII 8 ~ 200 98 175) Po1vqonum laDathif1Olium XVII 25 o I ~ XVII ~ ~25 85 t50~ ~--: , ~
Amaranthus retroflexus I ~ XVII2 ~ 200 85 t20) ~ ~VO 93/08689 212 2 8 9 8PCI/EP92/02535 Table_R
Mixtures of I with alachlor (XVIII) Rate HerbicidalE ( according tg/ha)activity (%) to Colby) _ _ _ _ S oi boh n e O
XVIII 50 o I ~ XVIII~ ~ 50 o ~0 8 ~ 50 o Polvaonum laDathifolium I ~ XVIII 8 ~ 50 100 180l Dioitaria isçhaemum a ~
XV~II 50 ~o I ~ XV~ 50 97 ~5 ) .
Mixtures of I with metolachlor (XIX) Rate Herbicidal E ( according (g/ha) activity (%) to Colby) S _ _ _ _ . _ So i~bohne XIX 50 o lon o I ~ XIX ~ ~ 50 o l 0 ~
I so ~ 101 ~ ~ 100 o 10 8 ~ 100 o lO~
,Amarant~us_retrof ~xus 8 ~o XIX 100 o X I X 8 ~10 0 7 o I ~. 0 S e t a r i a v i r i d i s XIX 50 ~0 I XIX 8 ~50 85 16~ ~ :
Diqitaria ischaemum 20 XlX 50 60 I ~ XIX ~ ~ 50 go 168 8 ~50 35 ~72 ~ 093/O~X9 212 2 8 9 ~ Pcr/EP92/~2535 ~able ~
Mixtures of I with trifluralin (XX) Rate Herbicidal E (according (g/ha) activity (%) ko Colby) .
S ~
.Soiabohne 2 8 1~
XX 100 o ~00 1 0 I I xx2 ~ 100 o lo 0 0 ( 1 0 8 ~ 100 lo 2 ~ 200 o 20~ lo 8 200 to (19 2 ~ ~00 o ~oo o ~19 8 ~ ~oo 10 (19) :':
~m~ranthus ~oflexus ~00 50 X ~ ~ 200 ~ .
.
Abutilon theoohrasti XX ~00 15 I ~ XX ~ ~ ~00 90 l~3) WO 93/086~9 2 1 2 2 3 ~ ~PCr/EP92/02535 Rate Herbicidal E (according (g/ha) activity (%) to Colby~
, Polvqonum laDathi4olium xx 200 o ~00 10 I ~ XXa ~ 200 95 t So 8 ~~00 95 ~ SS ) ::
Panicum maximum ~ ;
XX 1 0 0 9 0 , I I XX 2 ~ 10 0 9 9 l 9 0 ) ~ ~100 99 ~91 ) WO 93/08689 ~ PCI /EP92/02535 Table Mixtures of I with Chlorimuron ethyl (XXI~
Rate Herbicidal E (according (g/ha) activity (%) to Colby) _ _ . _ _ Soiabohne O
XXI ~
I ~ XXI 8 ~ 4 5 (0) 8 ~ 8 5 tO) Domoea ~UrDu~ea 8 5 ~:
XXI ~ ~ ~ .
I ~ XXI 8 ~ ~ 70 (~3) Bidens uilosa I 8 o I XXI C C CC t?01 WO 93tQ8689 212 2 8 9 8 PCI~/EP92tO2535 able ~
~ixtures of I with imazaquin (XXII) Rate HerbicidalE (according (~/ha) activity (%)to Colby) .
Soiabohne Z o a o XXII ~
16 0 .
I ~ XXII2 ~ ~ o (0 2 ~ 16 o ~0 8 ~ ~ 0 ~0) :
8 ~ 16 5 ~0 : ~:
IDomoea ~ur~urea ~ 8 10 I ~ XXII a ~ 16 75 16 Amarantbus retro~Lexus I ~ xxrI 8 ~ 16 go ~60) Polvaonum laDat~ifolium I ; XXII 2 ~ ~ 80 136) . -~YO 93/08689 2 1 2 2 ~ 3 i8PCI/EP92/02535 ~ -~able W
Mixtures of I with imazethapyr (XXIII) Rate HerbicidalE ( according (~/ha) activity (%)to Colby) Soiabohne 2 o O
8 n O
a lo I ~ XXIII 1 ~ 2 0 10~
1 ~ ~ O 10) 1 ~ 8 0 110~
1 ~16 o 10) 2 ~ 2 0 lO) 2 ~ ~ 0 lO) 2 ~ 8 0 l10) 2 ~16 o . ~ 2 0 tO) . O ~O) 8 0 ~lO) ~ ~16 0 lO) 8 ~ 2 0 ~0) 8 ~ ~ 0 lO) 8 ~ 8 0 110) 8 ~16 10 lO) I Do~oea ourDurea I ~ XXIII 8 1 8 70 l~9) :~W093~08689 2 ~ 2 2 8 ~ ~ PCT~EP92/02535 Rate Herbicidal E (according (~/ha) activity (~) to Colby) Amaranthus retroflexus XXIII 2 o ~, O ~' I XXIII ~ 1 2 85 (75) ~::
~ ~ ~ 85 ~75 Polvq~num laDathifolium I ~ XX~ 2 95 173 Setaria vlridis I ~ XXIII 1 ~ 16 75 IS0~
2 ~ 16 80 l50)
` ~ 2~2289~
-~093/08689 PCT/EP~2/OZS35 2-nitrobenzoate;
fomesafen is the common name for 5-[2-chloro-4-(trifluoromethyl)phenoXY]~N-(methylsulfonyl)-2-nitro-benzamide;
pendimethalin is the comMon name for N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline;
alachlor is the common name for 2-chloro-2',6'-diethyl-N-methoxymethylacetanilide;
metolachlor is the common name for 2-chloro-6'~ethyl-2'-methyl-N-(2-methoxy-1-methylethyl)acetanilide;
trifluralin is the common name for 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline;
chlorimuron-ethyl is the common name for ethyl 2-(4-chloro-6-methoxyPyrimidin-2-ylcarbamoylsulfamoyl)-lS benzoate;
imazaquin is the common name for (+)-2-~4,5-dihydro-4-methyl-4~ methylethyl)-~-oXQ-lH-imidazole-2-yl]-5-ethyl-3-pyridinecarboxylic acid; and imazethapyr is the common name for (+)-2-[4,5-dihydro-20 4-methyl-4-(1-methyleth~ 5-oxo-lH-2-yl]-3-quinoline carboxylic acid.
All these herbicides axe described in the "Pesticide Manual", ninth edition, 1991, published by the British Crop Protection Council, London.
::
The combinations of the invention are suitable for the control of important annual and perennial weeds, especially in plantation and permanent crops, such as for example in fruit, wine, citrus, forests and ornamental cultivations, in arable land outside the vegetation time (for example stubble treatment), as well as in the industrial area including highways and railways. Further uses are for the control of important weeds in a range of 3S crops, such as for example soya beans.
; .
- -~Y~093J0~89 2 ~ 2 2 8 9 8 PCT/EP92/02535 The combination of active ingredients of the invention can used for 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 Chrysanthemum.
.
MonocotyledonoUs weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron (= Elymus), Sagittaria, Monocharia, Fimbristylis, Eleocharis, Ischaemum and Apera.
The combinations of I with II-XI can be applied pre-emergently, and the combinations of I with XII-XXIII can be applied post-emergently. The rate of use lies between 0.001 and 5 kg/ha of the mixture, depending on the use. By using the mixtures for control of weeds the amount of herbicide needed can be generally reduced.
The weight ratio of component I) to the other component is generally between 50:1 and 1:100.
The compositions of the invention can also be used in admixture with other active agents for example other 30 plant-protection agents or pesticides, depending on the -particular need.
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 ~093/0868g 212 2 ~ 9 8 PCT/EP92/02535 additives may allow a decrease in the dose.
The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants.
Suitable li~uid carriers are, ~or example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and other mineral-oil fractions and plant oils.
Suitable solid carriers include mineral earths, 2 Og.
bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
As surface-active agents there can be used for 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 benzenesulfonic 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 active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes V.~ X ~
~ ",. " ~ . r ' " ' "~
-~093/08689 212 ~ 8 '~ ~ PCT/EP92/02535 o~ approximately 100 to 1,O00 l/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
~he preparation of these f9rmulations can be carried out in known manner, for example by milling or mixing processes. Optionally, individual components can be mixed just before use for example by the so-called commonly used tank-mixing method.
The following Examples illustrate the use of compositions of the invention.
The calculation of 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~ In this the following formula was used:
XY
E = X ~ Y ~
in which X = the herbicidal activity (%) of substance at a rate of p g/ha.
Y = the herbicidal activity (%) of substance B
at a rate of q ylha., and E = the expected additive activity of the herbicide (%) of the substances A + B at a rate of p + q g/ha.
If the observed value is greater than the value of E
calculated according to Colby, the combination shows synergistic activity.
-~093~08689 2 12 2 8 9 8 PCT/EP~2/02535 Ex~eFiments In a greenhouse the plant species shown in tables A-K were treated post-emergently with the components at the stated rates. The compositionS were diluted with 500 litres of water and sprayed evenly over the plants. ~wo weeks after treat~ent the herbicidal effect was evaluated.
Tiab 1 e 2~
Mixtures of I with glyphosate (II) Rate Herbicidal E (according : 10(g/ha) activity (%) to Colby) _ Amaranthus retrofle~us -~
II 50 5 :
S ~ 50 85 ~81) ' Cv~erus esculentus ~ .
I ~ 40 ~ : :
II ~ao s ~3) ~ ~:
' , '~
Elvmus re~ens I ~ :
II ~00 ~0 III ~ t~00 85 l70) s.~,i ;,~,l,.,..: :."~",,-:,,"",,~",~ ",~,,,"", ~'YO93/08689 2 12 2 8 9 8 PCT/EP92/02535 .. . .
~able B
Mixtures of I with sul~ometuron-methyl (III) Rate Herbicidal E (according (g/ha) activity (~) to Colby) - -Component Rate .HerbicidalE (according ~g/ha) activity (~)to Colby) 9-achiaria mutica a lo III 2 so I ~ III 8 ~ Z 75 ~59) Ses~ania exale~
~, 20 2 75 ( 68 ) :: ~
9romu~
o I ~ III 8 ~ ~ 75 (68) :
.s ", . ~
~--~093/08689 PCT/EP92/02535 212289~
Table C
Mixtures of I with imazapyr (IV) Rate HerbicidalE (according (g/ha) activity (~to Colby) . _ _ Setaria viridis I ~ IV 1 2 go ~B6) Sor~hum haleDense I ~ IV 8 ~ 1 90 ~76) CvDerus esculentus ~, 8 0 I V ~ 1 0 I ~ IV ~ ~ ~ 98 ~82 WO 93/08689 ;~ ~ 2 2 3 ;~ ~ PCI/EP92/02535 Table D
Mixtures of I with 2, 4-D (V) ~ate Herbicidal E (according (g/ha) activity ~%) to Colby) S ~
8idens Dilosa I ~ 60 V 100 o I ~ y s ~ 100 80 ~60) .~ ~ 200 85 ~6~) Sesbania exaltata ~ 0 I ~ V 5 ~ 100 go (~0) 8 ~ 100 98 ~aO) : .
, : Amarantb~s retroflex~
200 2a I ~ V 2 ~ 50 90 l73) 2 ~ 200 90 (76) W093/08689 2 12 2 ~ 9 8 PCT/EP92/02535 Table E
~ixtures of I with dicamba (VI) Rate Herbicidal ~ (according (g/ha) activity (%) to Colby) Sesbania exalt_ta : VI 25 70 I ~ YI 1 ~ 25 90 176) B id e n s P i ~s a ~ o ~ ~
I ~ VI 1 ~ 25 05 ~76 ~2~2~9~
Table F
~ixtures of I with diuron (VII) Rate Herbicidal E (according (g/ha) activity (%) to Colby) Sesbania exaltata I 0,5 0 2 30 ~: -YII 50 s I ~ VII 0,5 ~ 100 95 l80) 4 100 95 l80) 2 4 50 75 ~3~) ~ ~ 50 95 ~ 65 I ~ VII 2 ~ 25 85 l50) ~ ~ 25 99 ~65 8 ~ 25 100 ~80) CvDerus esculentus I 8 ~o I ~ VII 8 1 100 70 l~0) 8 ~ 200 ao l~3) Setaria viridis I ~ YII 1 ~ 100 97 ~72) ~WO 93/08689 PCI/EP~2/02~3~
21228g8 Table G
Mixtures of I with oxy~luorfen (VIII) ~ate Herbicidal E ( according (g/ha) activity (%) to Colby) S ~
Sesbania exaltata VIII 2 ~o I ~ VIII 1 ~ 2 70 (~9) 2 ~ 2 90 ~65) Amaranthus retroflexus .
VIII 2 ~0 .
I ~ VIII 1 ~ 2 98 S89~
-~ W093/08689 212 2 8 9 8 PCT/EP92/02535 able E
~ixtures of I with glu~osinate-ammonium (IX) ~ate Herbicidal E (according (y/ha) activity (%) to Colby) _ __ Setaria viridis I ~ 20 I ~ IX ~ ~ 80 80 (68) 6rachiaria mutica I ~ IX 8 ~ 80 95 ~36 Sorqhum t~aleoense IX ~0 0 I ~ IX8 ~ sn so 150) Sesbania exaltata I ~ IX 2 ~80 98 ~60 .~W0~3/08689 2 -1 2 2 ~ 3~ PC~/EP92/02535 Table I
Mixtures of I with amitrole (X) Rate Her~icidal E (according (g/ha)activity (%) to Colby) ~
Setaria viridis I ~ 20 I ~ X~ ~ 200 80 (68 Bracharia mutica I ~ 0 i ~ X~ ~ 200 70 l~0]
8 ~ 200 9S (33) ~ .
I ~ 70 X ~ ~ 50 a5 l76) Sesbania exaltata I ~ X 125 785 133) ` 2 ~ 25 90 153) 2 l 50 95 (65) ,...
W093t08689 PCT/EP92/0253~
2~22~9~
Table K
Mixture~ of I with sethoxydim (XI) Rate HerbicidalE (according (g/ha) activity (%)to Colby) 5 ~ , . _ _ _ Setaria viridis I ~ XI~ ~ lO0 98 ~73) .
Brac~iaria mutica I ~ XI 8 ~ 50 95 183) ,Bromus s~
I ~ XI 2 ~ 200 85 16~1 .W093/08689 2 12 2 8 ~ ~ PCT/EP92/02535 Ex~eriments In a gre~nhouse the plant species shown in tables L-~ were treated pre-emergently with the components at the stated rates. The compositionS were diluted with 500 litres of water and sprayed evenly over the soil. Two weeks after treatment the herbicidal effect was evaluated.
Table L
Mixtures of I with metribuzin (XI~) Rate Herbicidal ~ (according (g/ha) activity (%) to Colby) Soiabohne : ~:
XII 12,5 o O
I ~ XII~ 1 12,5 5 lO~
a ~ 12,5 s 1O~
~ ~ 50 o lO~ :
a ~ so s lo~
~ ~ ~oo s 15 8 ~ 100 10 ~5 IDomoea DurDurea I ~ XII8 I S0 70 l62 Amaranthus_retroflex~s I ~ 10 . XII S0 S0 I ~ XII ~ ~ 50 98 l55j ~ ~ 50 98 l55~ i :
~ ' ` 2~2289~
.W093~08689 PCT/EP92/02535 able M
Mixtures of I with linuron (XIII) Rate Herbicidal E (according (5/ha) activity (%) to Colby) Soiabohne a o XIII 100 o 200 o I ~ XIII2 ~ 100 o tn) 2 ~ 200 o tO) B ~ lOD 0 t6) . .
8 ~ 200 S ~5) Amaranthus retroflexus a 20 XIII l I ~ XIII 8 lOo 80 t201 PolYqonum laDathiflolium I ~ Xl I I 2 , 200 80 160 Setaria virid_5 8 ~0 XIII 100 o I ~ XIII 8~ 100 75 ~, :~
W093/0~89 212 2 8 9 g PCT/EP92/0253~
~able N
~ixtures of I wi~h acifluorfen (XIV) RateHerbicidal E taccording (g/ha)activity (%) ta Colby) S , _ _ _ _ Soiabohne I 2 o ~ 20 8 ~0 ~o 10 I I XIV 2 ~ 10 o 1 2 ~ 20 10 15 2 ~ ~0 0 l10) 0 ~20) 20 20 ~2~) ~ ~ 40 10 ~27) 8 ~ 10 20 ~0) 8 ~ 20 50 ~ ~ ~o 10 1~6) Ioomoea Dur~urQa XIV 10 o I ~ XIV8 1 10 85 (70) 8 ~ 20 95 (73~
. . .
Amaranthus retroflexus XIV ~0 30 I ~ XIV ~ ~ ~0 90 (58) :
Polvqon ~ LaDathifolium XlV 10 o I ~ XIV ~ ~ 10 95 l80) .~
W093/08689 2 12 2 8 9 o PCT/EP92/02535 Rate Herbicidal E (according (g/ha) - activity t%) to Colby) Sorqhum haleDense I ~ XIV 2~ 20 90 176) ~iqitaria ischaemum 2 10 I
I ~ XIV 2 ~ 20 75 (SSI
, ~ ~
.
WO 93/08689 2 ~ 2 2 8 9 ~ PCI/EP92/02535 ..
Table o Ni~tures of I with lactof en (XV) Rate Herbicidal F ( according (g/ha) activity (%) to Colby) Soiabo~ne o XY 20 o I ~ XV 1 l 20 2 ~ 20 ~ ~ 20 0 110) Amaranthus retroflexus ~0 XV 20 ~o I ~ XV 2 ~20 ~5 ~52 ~ ~20 90 (701 Po~vqonum-laDathiflolium 2 ~o 1 ~ XV 2 ~20 go ~, ;
~iqitaria ischaemum I ~ XV 1 ~20 90 ~ 50 ~ ,;
æ~22~9~
Ta~l~ P
Mixt~res of I wi~h fomesafen (XVI) Rate Herbicidal E (according (g/h~) activity (%) to Colby) S P i a bo h n e 2 o ~0 20 I ~ XVI 2 ~10 0 ~10) 2 ~ ~ 30 ~20) 2 ~80 20 ~20) 10 10 ~28) ~0 10 ~36) ~ ~80 20 ~36) 8 ~10 20 128) 8 ~~0 20 (36) 8 ~80 20 ~36) Jmp~moea DurDurea .
XYI ~0 20 ao ~o I I XVI 8 ~~0 90 168) 8 ~80 95 ~76) :
~.
Polvqonum laDathi~lolium ~, 75 : :
XV I 10 ~ 5 I ~ XYI 2 110 80 t8) ~ ~10 98 177 ) -~VO 93/û8689 PCI/EP92/02535 2:~22~8 Rate HerbicidalE (according ~/ha) activity (%) to Colby) .
Sorallym halepense I ~ XYI ~ ~ 10 85 ~55) Diqitaria ischaemum I ~ XVI ~ ~ 10 90 (65 ~-n ~
~W093/08689 2 ~ 2 2 ~ ~ ~ PCT/~P92/02535 able Q
~ixtures of I with pendimethalin (XVII) RateHerbicidal E (according (g/ha)~ctivity (%) to Colby) S ~
Soiabohne I 2 o O
. 8 0 XVII 25 o 200 o I ~ XVII 2 ~ 2S o 10) ~ ~ 25 0 10) 8 ~ 25 0 (0) 2 o 200 o 10) ~ ~ 200 o lO) 8 ~ 2~0 o ~0 Setaria viridis I 8 o I ~ XVII 8 ~ 200 98 175) Po1vqonum laDathif1Olium XVII 25 o I ~ XVII ~ ~25 85 t50~ ~--: , ~
Amaranthus retroflexus I ~ XVII2 ~ 200 85 t20) ~ ~VO 93/08689 212 2 8 9 8PCI/EP92/02535 Table_R
Mixtures of I with alachlor (XVIII) Rate HerbicidalE ( according tg/ha)activity (%) to Colby) _ _ _ _ S oi boh n e O
XVIII 50 o I ~ XVIII~ ~ 50 o ~0 8 ~ 50 o Polvaonum laDathifolium I ~ XVIII 8 ~ 50 100 180l Dioitaria isçhaemum a ~
XV~II 50 ~o I ~ XV~ 50 97 ~5 ) .
Mixtures of I with metolachlor (XIX) Rate Herbicidal E ( according (g/ha) activity (%) to Colby) S _ _ _ _ . _ So i~bohne XIX 50 o lon o I ~ XIX ~ ~ 50 o l 0 ~
I so ~ 101 ~ ~ 100 o 10 8 ~ 100 o lO~
,Amarant~us_retrof ~xus 8 ~o XIX 100 o X I X 8 ~10 0 7 o I ~. 0 S e t a r i a v i r i d i s XIX 50 ~0 I XIX 8 ~50 85 16~ ~ :
Diqitaria ischaemum 20 XlX 50 60 I ~ XIX ~ ~ 50 go 168 8 ~50 35 ~72 ~ 093/O~X9 212 2 8 9 ~ Pcr/EP92/~2535 ~able ~
Mixtures of I with trifluralin (XX) Rate Herbicidal E (according (g/ha) activity (%) ko Colby) .
S ~
.Soiabohne 2 8 1~
XX 100 o ~00 1 0 I I xx2 ~ 100 o lo 0 0 ( 1 0 8 ~ 100 lo 2 ~ 200 o 20~ lo 8 200 to (19 2 ~ ~00 o ~oo o ~19 8 ~ ~oo 10 (19) :':
~m~ranthus ~oflexus ~00 50 X ~ ~ 200 ~ .
.
Abutilon theoohrasti XX ~00 15 I ~ XX ~ ~ ~00 90 l~3) WO 93/086~9 2 1 2 2 3 ~ ~PCr/EP92/02535 Rate Herbicidal E (according (g/ha) activity (%) to Colby~
, Polvqonum laDathi4olium xx 200 o ~00 10 I ~ XXa ~ 200 95 t So 8 ~~00 95 ~ SS ) ::
Panicum maximum ~ ;
XX 1 0 0 9 0 , I I XX 2 ~ 10 0 9 9 l 9 0 ) ~ ~100 99 ~91 ) WO 93/08689 ~ PCI /EP92/02535 Table Mixtures of I with Chlorimuron ethyl (XXI~
Rate Herbicidal E (according (g/ha) activity (%) to Colby) _ _ . _ _ Soiabohne O
XXI ~
I ~ XXI 8 ~ 4 5 (0) 8 ~ 8 5 tO) Domoea ~UrDu~ea 8 5 ~:
XXI ~ ~ ~ .
I ~ XXI 8 ~ ~ 70 (~3) Bidens uilosa I 8 o I XXI C C CC t?01 WO 93tQ8689 212 2 8 9 8 PCI~/EP92tO2535 able ~
~ixtures of I with imazaquin (XXII) Rate HerbicidalE (according (~/ha) activity (%)to Colby) .
Soiabohne Z o a o XXII ~
16 0 .
I ~ XXII2 ~ ~ o (0 2 ~ 16 o ~0 8 ~ ~ 0 ~0) :
8 ~ 16 5 ~0 : ~:
IDomoea ~ur~urea ~ 8 10 I ~ XXII a ~ 16 75 16 Amarantbus retro~Lexus I ~ xxrI 8 ~ 16 go ~60) Polvaonum laDat~ifolium I ; XXII 2 ~ ~ 80 136) . -~YO 93/08689 2 1 2 2 ~ 3 i8PCI/EP92/02535 ~ -~able W
Mixtures of I with imazethapyr (XXIII) Rate HerbicidalE ( according (~/ha) activity (%)to Colby) Soiabohne 2 o O
8 n O
a lo I ~ XXIII 1 ~ 2 0 10~
1 ~ ~ O 10) 1 ~ 8 0 110~
1 ~16 o 10) 2 ~ 2 0 lO) 2 ~ ~ 0 lO) 2 ~ 8 0 l10) 2 ~16 o . ~ 2 0 tO) . O ~O) 8 0 ~lO) ~ ~16 0 lO) 8 ~ 2 0 ~0) 8 ~ ~ 0 lO) 8 ~ 8 0 110) 8 ~16 10 lO) I Do~oea ourDurea I ~ XXIII 8 1 8 70 l~9) :~W093~08689 2 ~ 2 2 8 ~ ~ PCT~EP92/02535 Rate Herbicidal E (according (~/ha) activity (~) to Colby) Amaranthus retroflexus XXIII 2 o ~, O ~' I XXIII ~ 1 2 85 (75) ~::
~ ~ ~ 85 ~75 Polvq~num laDathifolium I ~ XX~ 2 95 173 Setaria vlridis I ~ XXIII 1 ~ 16 75 IS0~
2 ~ 16 80 l50)
Claims (4)
1. A herbicidal composition which comprises, a mixture of 2-[7-fluoro-3-oxo-4-(2-propynyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]perhydroimidazo-[1,5-a]pyridine-1,3-dione (I) and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D
(V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaquin (XXII) and imazethapyr (XXIII).
(V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaquin (XXII) and imazethapyr (XXIII).
2. A composition according to claim 1, in which the weight ratio of the mixture components is between 50:1 and 1:100.
3. A method of combating weeds which comprises applying post-emergently, a composition according to claim 1 or 2, which comprises component I and at least one of the components II to XI.
4. A method combating weeds which comprises applying pre-emergently, a composition according to claim 1 or 2, which comprises component I and at least one of the components XII to XXIII.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4136740A DE4136740A1 (en) | 1991-11-05 | 1991-11-05 | HERBICIDES WITH SYNERGISTIC EFFECT |
| DEP4136740.5 | 1991-11-05 | ||
| PCT/EP1992/002535 WO1993008689A1 (en) | 1991-11-05 | 1992-10-30 | Synergistic herbicidal compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2122898A1 true CA2122898A1 (en) | 1993-05-13 |
Family
ID=6444326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002122898A Abandoned CA2122898A1 (en) | 1991-11-05 | 1992-10-30 | Synergistic herbicidal compositions |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0612213A1 (en) |
| JP (1) | JPH07502498A (en) |
| CN (1) | CN1073071A (en) |
| AU (1) | AU2920492A (en) |
| BR (1) | BR9206712A (en) |
| CA (1) | CA2122898A1 (en) |
| DE (1) | DE4136740A1 (en) |
| FI (1) | FI942050A0 (en) |
| HU (1) | HUT66872A (en) |
| IL (1) | IL103626A0 (en) |
| RU (1) | RU94021656A (en) |
| TW (1) | TW224932B (en) |
| WO (1) | WO1993008689A1 (en) |
| ZA (1) | ZA928540B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995023509A1 (en) * | 1994-03-01 | 1995-09-08 | E.I. Du Pont De Nemours And Company | Herbicidal bicyclic hydantoins |
| DE10209478A1 (en) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Gmbh | Herbicide combinations with special sulfonylureas |
| KR100703303B1 (en) | 2005-04-28 | 2007-04-03 | 삼성전자주식회사 | Method of requesting allocation of uplink resources for extended real-time polling service in a wireless communication system |
| UY32345A (en) * | 2008-12-19 | 2010-06-30 | Basf Se | FLUID AQUATIC COMPOSITIONS OF CONCENTRATES OF A MICROENCAPSULATED DINITORANILINE HERBICIDE |
| JP2014159374A (en) * | 2011-05-20 | 2014-09-04 | Nippon Nohyaku Co Ltd | Perishing and defoliation agent composition for crop |
| EA019754B1 (en) * | 2011-07-13 | 2014-06-30 | Юрий Аглямович ГАРИПОВ | Synergetic herbicidal composition |
| CN103120180A (en) * | 2011-11-17 | 2013-05-29 | 浙江新安化工集团股份有限公司 | Herbicide composition prepared by glyphosate and diuron, and preparation method thereof |
| JP2016027002A (en) * | 2012-11-16 | 2016-02-18 | 日本農薬株式会社 | Herbicide composition |
| CN108782597B (en) * | 2017-04-26 | 2021-08-06 | 四川利尔作物科学有限公司 | Suspending agent containing glyphosate and flumioxazin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
- 1991-11-05 DE DE4136740A patent/DE4136740A1/en not_active Withdrawn
-
1992
- 1992-10-30 AU AU29204/92A patent/AU2920492A/en not_active Abandoned
- 1992-10-30 RU RU94021656/04A patent/RU94021656A/en unknown
- 1992-10-30 WO PCT/EP1992/002535 patent/WO1993008689A1/en not_active Application Discontinuation
- 1992-10-30 CA CA002122898A patent/CA2122898A1/en not_active Abandoned
- 1992-10-30 EP EP92923266A patent/EP0612213A1/en not_active Withdrawn
- 1992-10-30 HU HU9401307A patent/HUT66872A/en unknown
- 1992-10-30 BR BR9206712A patent/BR9206712A/en not_active Application Discontinuation
- 1992-10-30 JP JP5508170A patent/JPH07502498A/en active Pending
- 1992-11-03 IL IL103626A patent/IL103626A0/en unknown
- 1992-11-05 ZA ZA928540A patent/ZA928540B/en unknown
- 1992-11-05 CN CN92113786A patent/CN1073071A/en active Pending
- 1992-12-04 TW TW081109737A patent/TW224932B/zh active
-
1994
- 1994-05-04 FI FI942050A patent/FI942050A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI942050A (en) | 1994-05-04 |
| AU2920492A (en) | 1993-06-07 |
| WO1993008689A1 (en) | 1993-05-13 |
| BR9206712A (en) | 1995-10-24 |
| CN1073071A (en) | 1993-06-16 |
| HUT66872A (en) | 1995-01-30 |
| IL103626A0 (en) | 1993-04-04 |
| RU94021656A (en) | 1996-04-10 |
| ZA928540B (en) | 1993-05-05 |
| FI942050A0 (en) | 1994-05-04 |
| JPH07502498A (en) | 1995-03-16 |
| EP0612213A1 (en) | 1994-08-31 |
| HU9401307D0 (en) | 1994-08-29 |
| DE4136740A1 (en) | 1993-05-06 |
| TW224932B (en) | 1994-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |