CA1163109A - Selective herbicidal agents based on a triazinedione - Google Patents
Selective herbicidal agents based on a triazinedioneInfo
- Publication number
- CA1163109A CA1163109A CA000390558A CA390558A CA1163109A CA 1163109 A CA1163109 A CA 1163109A CA 000390558 A CA000390558 A CA 000390558A CA 390558 A CA390558 A CA 390558A CA 1163109 A CA1163109 A CA 1163109A
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- Prior art keywords
- methyl
- chloro
- dimethylurea
- composition
- herbicidal composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- 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
A herbicidal composition comprising (I) 1-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4(1H,3H)-dione of the formula
A herbicidal composition comprising (I) 1-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4(1H,3H)-dione of the formula
Description
1 3 ~3~9 ~ he invention relates to new herbicidal synergistic combinations which consist of a certain triazinedione and of certain cereal herbicides.
It has already been disclosed that l-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4-(lH,3H)-dione can be used as a herbicide (see, for example, Danish Patent Specification 136,067).
It is also knc~n tha-t the active compounds mentioned belcw can be used as cereal herbicides (see, for example Chemie der Pflanzenschutz- und Schadlings-bekampfungsmittel (Chemistry of Plant Protection Agents and Agents for Combating Pests), volume 5 "Herbizide" ("Herbicides"), Springer-~erlag (1977): certain ureas (such as chlorotoluron, isoproturon, linuron, methabenzthiazuron and metoxuron), certain thiolcarbama-tes (such as dialla-te and triallate), certain carboxylic acid esters (such as benzoylprop-ethyl, chlorfenprop-me-thyl, diclofop-methyl, flamprop-methyl and flamprop-isopropyl), certain benzoic acids (such as dicamba), certain benzonitriles (such as bronoxynil and ioxynil), certain phenol derivatives (such as DNOC, dinoterb and dinoseb acetate), oe rtain dinitroanilines (such as pendimethalin and trifluralin), certain diphenyl ethers (such as nitrofen), certain phenoxyalkanecarboxylic acids (such as 2,4-D, 2,4-DP, MCPA and MCPP), certain s-triazines (such as cyanazine, simazine and terbutryn), certain as-triazin-5-ones ~such as isomethiozin and metribuzin) and oe rtain other hetero-cyclic active compounds, in particular bentazon and difenzoguat.e abovementioned active compounds (which are called by their common names) indeed exhibit a good tolerance in cereal crops, for example in wheat and barley, but they display certain weaknesses when used against important weeds and grasses.
According to the present invention there is now provided a new herbicidal composition containing as active ingredients (I) l-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4(1H,3~)-dione of the formula ~, :
~3:LOg (CH3)3C-CH2-N N N 2 (I) o N SC2H5 and (II) one of the active oompounds mentioned kelcw from the cereal herbicide ; group, that is to sa~ either (1) one of the follcwing ureas: (a) N'-(3-chloro-4-methylphenyl)-N,N-dimethyl-~ urea (chlorotoluron) ("la"), (b) N'-(4-isopropylphenyl)-N,N-dimethylurea (iso-: proturon) ("lb"), (c) N'-~3,4-dichlorophenyl)-N-methoxy-N-methylurea (linuron) ("lc"), (d) N-benzothiazol-2-yl-N-methyl-N'-methylurea (methabenzthiazuron) ("ld") or (e) N'-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea (metoxuron1 ("le") or
It has already been disclosed that l-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4-(lH,3H)-dione can be used as a herbicide (see, for example, Danish Patent Specification 136,067).
It is also knc~n tha-t the active compounds mentioned belcw can be used as cereal herbicides (see, for example Chemie der Pflanzenschutz- und Schadlings-bekampfungsmittel (Chemistry of Plant Protection Agents and Agents for Combating Pests), volume 5 "Herbizide" ("Herbicides"), Springer-~erlag (1977): certain ureas (such as chlorotoluron, isoproturon, linuron, methabenzthiazuron and metoxuron), certain thiolcarbama-tes (such as dialla-te and triallate), certain carboxylic acid esters (such as benzoylprop-ethyl, chlorfenprop-me-thyl, diclofop-methyl, flamprop-methyl and flamprop-isopropyl), certain benzoic acids (such as dicamba), certain benzonitriles (such as bronoxynil and ioxynil), certain phenol derivatives (such as DNOC, dinoterb and dinoseb acetate), oe rtain dinitroanilines (such as pendimethalin and trifluralin), certain diphenyl ethers (such as nitrofen), certain phenoxyalkanecarboxylic acids (such as 2,4-D, 2,4-DP, MCPA and MCPP), certain s-triazines (such as cyanazine, simazine and terbutryn), certain as-triazin-5-ones ~such as isomethiozin and metribuzin) and oe rtain other hetero-cyclic active compounds, in particular bentazon and difenzoguat.e abovementioned active compounds (which are called by their common names) indeed exhibit a good tolerance in cereal crops, for example in wheat and barley, but they display certain weaknesses when used against important weeds and grasses.
According to the present invention there is now provided a new herbicidal composition containing as active ingredients (I) l-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4(1H,3~)-dione of the formula ~, :
~3:LOg (CH3)3C-CH2-N N N 2 (I) o N SC2H5 and (II) one of the active oompounds mentioned kelcw from the cereal herbicide ; group, that is to sa~ either (1) one of the follcwing ureas: (a) N'-(3-chloro-4-methylphenyl)-N,N-dimethyl-~ urea (chlorotoluron) ("la"), (b) N'-(4-isopropylphenyl)-N,N-dimethylurea (iso-: proturon) ("lb"), (c) N'-~3,4-dichlorophenyl)-N-methoxy-N-methylurea (linuron) ("lc"), (d) N-benzothiazol-2-yl-N-methyl-N'-methylurea (methabenzthiazuron) ("ld") or (e) N'-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea (metoxuron1 ("le") or
(2) one of the follcwing thiolcarbamates: (a) S-2,3-dichloroallyl diisopropyl-thiolcarbamate (diallate) ("2a") or (b) S-2,3,3-trichloroallyl diisopropylthiol-carbamate (triallate) ("2b"); or
(3) one of the following carboxylic acid esters: (a) ethyl N-benzoyl-N-(3,4-di-:chlorophenyl)-2-aminopropionate (benzoylprop-ethyl) ("3a"), (b) methyl 2-chloro-: 3-(4-chlcrophenyl) propionate (chlorfenprop-methyl) ("3b"~, (c) 2-[4-(2,4-dichlorcphenoxy)-phenoxy~-propionic acid methyl ester (diclofop-methyl) ("3c"), (d) methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate (flamprop-~: methyl) ("3d") or (e) isopropyl N-benzoyl-N-(3-chloro-4 fluoro-phenyl)-2-amino-propionate (flamprcp-isopropyl) ("3e"); or
(4) the follcwing benzoic acid derivative: (a) 2-methoxy-3,6-dichloro-benzoic acid (dica~ba) ("4a"); or
(5) one of the following benzonitriles: (a) 3,5-diiodo-4-hydrnxy-benzonitrile ~: (ioxynil) ("Sa") or (b) 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil) ("5b");
or ~,...
`~-lt ~ .
, : :
I 1 63 lOg
or ~,...
`~-lt ~ .
, : :
I 1 63 lOg
(6) one of the follcwing phenol deriv~tives: (a) 2-methyl-4,6-dinitrophenol (DNOC) ("6a"), (b) 2,4-dinitro-6-tert.-butylphenol (dinoterb) ("6b") or (c) 2-sec.-butyl-4,6-dinitrophenyl aoe tate (dinoseb acetate) ("6c"); or
(7) one of the following dinitroanilines: (a) N-(l-ethylpropyl)-3,4-dim~thyl-2,6-dinitroaniline (pendimethalin) ("7a") or (b) N,N-di-(n-propyl)-2,6-dinitro-4-trifluoramethyl-aniline (trifluralin) ("7b"); or
(8) the following diphenyl ether: (a) 2,4-dichlorophenyl 4-nitrophenyl ether (nitrofen) ("8a"); or
(9) one of the fol~owing phenoxyaIkanecarbaxylic acids: ~a) 2,4-dichloropheno~y-acetic acid (2,4-D) ("9a"), (b) 2,4-dichlorophenox~propionic acid (2,4-DP~ ("9b"), (c) 4-chloro-2-methylphenoxyaoetic acid (~CPA) ("9c") or (d) 2-(2-methyl-4-chloro-phenoxy)-propionic ad d (MCPP, mecoprop) ("9d"); or
(10) one of the following s-triazines; (a) 2-chloro-4-ethylamino-6-(1-me-thyl-1-cyanoethylamino)-s-triazine (cyanazine) ("lOa"), (b) 2-chloro-4,6-bi~-(ethylamino)-s-triazine (simazine) ("lOb") or (c) 2-ethylamino-4-methyl-thio-6-tert.-butylamino-s-triazine (terbutryn) ("lOc"); or
(11) ane of the following as-triazin-5-anes: (a) 4-N,N-isobutylimino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (isomethiozin) ("lla") or (b) 4-amino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (me-tribuzin) ("llb"); or
(12) one of the following heterocyclic active campounds: (a) 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (bentazon) ("12a") or (b) 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl-sulphate (difenzoquat) ("12b"), in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier cantain-ing a surface active agent.
The new active compound comhinations of the present invention have a particularly broad herbicidal activity in various crops, in particular in cereal crops.
~"
~3~3:10~
Surprisingly, the activity of the active compcund combinations accord-ing to the invention is considerably more powerful than the sum of the actions of the individua] active compounds. A true synergistic effect which could not be predicted is present, and not only a supplementary action~ The new active com-p~und combinations thus represent a valuable enrichment of selective herbicides, in particular of cereal herbicides.
Examples which may be mentioned of weeds which in general occur as a contaminant in cereal crops and which can reliably be co~bated by the acti~e com~
pound combinations according to the in~ention are:
dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ip2moea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Solanum; and monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachi æ ia, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, AloFecurus and Apera.
EIowever, the use of the active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same ~anner to other plants.
The new active cc~pound combinations are particularly suitable for cGm~
bating weeds in the wheat and barley varieties of cereal.
The synergistic effect of the active compound combinations according to the invention is particularly highly pronounced at oe rtain concentration ratios.
~Iowever, the weight ratios of the active compounds in the active compound combina-`3 1 ~ 0 ~
tions can be varied within relatively wide limits. In general, 0.5 to 10 parts by weight, preferably 0.5 to 5 parts by weight, of active co~pound from the active compound group (II) are present per part by weight of active co~pound of the formula (I).
rrhe active compound ccmbinations accord mg to the invention can be con-verted to the customary formulations, such as solutions, emulsions, -~ettable powders, sus~ensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations may be produced in known manner, for example by mix-ing the active cQmpounds with extenders, that is to say liquid or solid diluents or carriers, optionally with the use of surfaoe -active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as rm extender, organic solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, especially sol~ents, there are suitable in the main, aromatic hydrocæbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chloro-benzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydro-carbons, such as cyclohexane or p æ æ fins, for exa~ple mineral oil fractions,alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as aoetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polæ solvents, such as dime-thylformamide and dimethylsulphoxide, as well as water.
As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartæ, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic ninerals, such as highly-dispersed silicic acid, : ~3~3~09 .
alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pu~ice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, COCQnUt shells, maize cobs and tobacco stalks.
As enmlsifying and/or foam~forming agents there may be used non i onic and anionic emulsifiers, such as polyoxyethylene~fatty acid esters, polyoxy-ethylene-fatty aloohol ethers, for example alkyla~yl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sul~honates as well as albumin hydrolysis pro-ducts. Dispersing agents include, for example, lignin sulphite waste liquors andmethylcellulose.
Adhesives such as carboxymethyl oe llulose and natural and synthetic polymers in the form of pcwders, granules or lati oe s, such as gum æ abic, poly-vinyl alcohol and polyvinyl acetate, can be used in the formulations.
It is possible to u æ colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and tra oe nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
m e for~ulations in general contain from 0.1 to 95 per cent by weight of total active compounds, preferably from 0.5 to 90 per cent by weight.
e active ccmpound ccmbinations according to the invention are in general used in the form of finished formLlations. However, it is also possible for the active cc~lpounds contained in the active compound ccmbinations to be mixed as m dividual form~lations when used, that is to say to be used in the form d tank mixtures.
The new active compound ccmbinations, as such or in their foxmulations, .
ean also be used as mixtures with other knawn cereal herbieides, finished formula-tions or tank mixtures again being possible. Mixtures with other knawn active eompounds, such as fungieides, insectieides, acarieides, nemati d des, bird repel-lants, growth faetorsr plant nutrients and agents whieh improve soil strueture, are also possible.
m e ne~ active compound combinations ean be used as sueh, in the form of their formulations or in the use forms prepared therefram by further dilutian, sueh as ready-to-use solutions, suspensions, em~lsions, powders, pastes and granules. They are used in the eustomary m~nner, for example by watering, spray-ing, atamising, dusting or seattering.
The amounts of aetive eompound eambination aeeording to the inventianapplied ean be varied within a oe rtain range; they depend, inter alia, on the weather and on soil faetors. In general, the amounts applied are between 0.2 and 8 kg of aetive eompound eambination per ha, preferably between 0.5 and 5 kg/ha.
m e aetive eompound eambinations aeeording to the invention ean be applied either before or after emergen oe of the plants. m ey can also be ineor-porated into the soil before sawing.
The present invention also provides herbieidal eamposition cantaining as active ingredient an active ingredient ccmbinatian of the present invention in admixture with a solid diluent or earrier or in admixture with a liquid diluant or earriar containing a surfaae-activa agent.
The present invention also provides a method of combating weed which camprises applying to the waeds, or to a habitat thereof, a aetive compound camr bination of tha present invention alone or in tha form of a camposition cantain-ing as active ingredient an active compound combination of the present invention in admixture with a diluent or carrier.
The present invantion further provides crops, espaeially cereal crop, protected from damage by weeds by being grown in areas in which immediately prior to and/or during the time of the growing an active compound combination of the present invention was applied alone or in adm~xture with a diluent or carrier.
It will be seen that the usual methods of provid~ng a harvested crop may be improved by the present invention.
The good herbicidal action of the novel active compcund co~binatio~s can be seen from the Examples which follow. Whilst the individual active com-pounds have weaknesses in herbicidal action, the combinations show a very broad action against weeds which goes beyond a simple additive action.
A synergistic effect exists with herbicides whenever the herbicidal action of the active compound combination is greater than that of the individu-ally applied active compounds.
m e action to ke expected for a given combination of two herbicides can be calculated as follows (see OOLBY, S.R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20 - 22, 1967):
If X = ~ damage by herbicide A used in an amount of p kg/ha and Y = ~ damage by herbicide B used in an amount of q kg/ha and E = the expected damage by herbicides A and B used in amounts of p ; and q kg/ha then E = X ~ Y - X . Y.
' ~ 100 If the actual damage is greater than calculated~ the action of the CO~r bination is superadditive, that is to say it exhibits a synergistic effect.
he examples which ~ollow show that the found herbicidal action of the active compound oombinations according to the invention on weeds is greater than ~ the caIculated action, that is to say a genuine synergistic effect exists.
:
~ - 8 -3 :1 ~ 9 Example A
Pre-emergence test Solvent: 5 parts by ~eight of acetone Emulsifier: 1 part by weight of aIkylaryl polyglycol ether To produce a suitable preparation of active compounds, 1 part by weight of the active ccmpound combination was mixed with the stated amount of solvent, the stated D unt of emulsifier was added and the concentrate was diluted with water to the desired concentration.
Seeds of the test plants were sown in normal soil and, after 24 hours, watered with the preparation of the active compounds. It was expedient to keep constant the am~unt of water per unit area. m e total concentration of the active compounds in the preparation was of no importance, only the amount of active compounds applied per unit area being decisive. After three weeks, the degree of damage to the plants was rated in % damage in comparison to the develop-ment of the untreated control. The figures denoted:
0% = no action (like untreated control) 100~ = total destruction The active co~lpounds, amounts applied and results can be seen from the table which follows:
:
_ g _ : .
1~3~
o o o o o o o $
o~ln 'no~l O
.~ ~
~, ~ , 11 ,, ~ ¦ ;~ I . 1 N _~ N ~ ;j N O
: a : ~ - N
b ~ ~ '' ~ H ,~ ~ ~ _ r~
:
~; ';
- '' ' , ' ..
~ ~63109 .Example B
-Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound ccmbinatio~ was mixed with the stated amount of solvent, the stated amount of emulsifier was added and the concentrate was diluted with water to the desired concentration.
Test plants which had a heig~lt of 5 to 15 cm were sprayed with the pre-p æ ation of the active co~,pounds in such a way as to apply the amounts of active compounds per unit area which were indicated in the table.
m e amount of water applied was 2,000 l/ha. After 3 weeks, the degree of damage to the plants was rated in ~ damage in comp æison to the develcpm~nt of the untreated control.
m e figures denoted:
0% = no action (like untreated control) 100~ = total destruction The acti.ve ccmpcunds, amounts applied and results can be seen from the : table which follows:
l~u I h ~ o u) o o\o ~ h o o o LO o o o !~i ~ o LO o ~ ~ ' ¦ O ~ ~ ¦ o o 4~ o o ~ ~ ~
~ *. ~ ~
~ ~ Lr~ In ~ ~
~ ~ co ~ ~ ~ ~
~¦ --~ ~ '' ~ ^ ' 9 9 ~ u ~ 1~ I
;~ ~ ~ I ~I N
:: _ ~ ~ ~ ~ Z
~ O ~ H ~
.
'
The new active compound comhinations of the present invention have a particularly broad herbicidal activity in various crops, in particular in cereal crops.
~"
~3~3:10~
Surprisingly, the activity of the active compcund combinations accord-ing to the invention is considerably more powerful than the sum of the actions of the individua] active compounds. A true synergistic effect which could not be predicted is present, and not only a supplementary action~ The new active com-p~und combinations thus represent a valuable enrichment of selective herbicides, in particular of cereal herbicides.
Examples which may be mentioned of weeds which in general occur as a contaminant in cereal crops and which can reliably be co~bated by the acti~e com~
pound combinations according to the in~ention are:
dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ip2moea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Solanum; and monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachi æ ia, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, AloFecurus and Apera.
EIowever, the use of the active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same ~anner to other plants.
The new active cc~pound combinations are particularly suitable for cGm~
bating weeds in the wheat and barley varieties of cereal.
The synergistic effect of the active compound combinations according to the invention is particularly highly pronounced at oe rtain concentration ratios.
~Iowever, the weight ratios of the active compounds in the active compound combina-`3 1 ~ 0 ~
tions can be varied within relatively wide limits. In general, 0.5 to 10 parts by weight, preferably 0.5 to 5 parts by weight, of active co~pound from the active compound group (II) are present per part by weight of active co~pound of the formula (I).
rrhe active compound ccmbinations accord mg to the invention can be con-verted to the customary formulations, such as solutions, emulsions, -~ettable powders, sus~ensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations may be produced in known manner, for example by mix-ing the active cQmpounds with extenders, that is to say liquid or solid diluents or carriers, optionally with the use of surfaoe -active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as rm extender, organic solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, especially sol~ents, there are suitable in the main, aromatic hydrocæbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chloro-benzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydro-carbons, such as cyclohexane or p æ æ fins, for exa~ple mineral oil fractions,alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as aoetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polæ solvents, such as dime-thylformamide and dimethylsulphoxide, as well as water.
As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartæ, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic ninerals, such as highly-dispersed silicic acid, : ~3~3~09 .
alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pu~ice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, COCQnUt shells, maize cobs and tobacco stalks.
As enmlsifying and/or foam~forming agents there may be used non i onic and anionic emulsifiers, such as polyoxyethylene~fatty acid esters, polyoxy-ethylene-fatty aloohol ethers, for example alkyla~yl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sul~honates as well as albumin hydrolysis pro-ducts. Dispersing agents include, for example, lignin sulphite waste liquors andmethylcellulose.
Adhesives such as carboxymethyl oe llulose and natural and synthetic polymers in the form of pcwders, granules or lati oe s, such as gum æ abic, poly-vinyl alcohol and polyvinyl acetate, can be used in the formulations.
It is possible to u æ colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and tra oe nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
m e for~ulations in general contain from 0.1 to 95 per cent by weight of total active compounds, preferably from 0.5 to 90 per cent by weight.
e active ccmpound ccmbinations according to the invention are in general used in the form of finished formLlations. However, it is also possible for the active cc~lpounds contained in the active compound ccmbinations to be mixed as m dividual form~lations when used, that is to say to be used in the form d tank mixtures.
The new active compound ccmbinations, as such or in their foxmulations, .
ean also be used as mixtures with other knawn cereal herbieides, finished formula-tions or tank mixtures again being possible. Mixtures with other knawn active eompounds, such as fungieides, insectieides, acarieides, nemati d des, bird repel-lants, growth faetorsr plant nutrients and agents whieh improve soil strueture, are also possible.
m e ne~ active compound combinations ean be used as sueh, in the form of their formulations or in the use forms prepared therefram by further dilutian, sueh as ready-to-use solutions, suspensions, em~lsions, powders, pastes and granules. They are used in the eustomary m~nner, for example by watering, spray-ing, atamising, dusting or seattering.
The amounts of aetive eompound eambination aeeording to the inventianapplied ean be varied within a oe rtain range; they depend, inter alia, on the weather and on soil faetors. In general, the amounts applied are between 0.2 and 8 kg of aetive eompound eambination per ha, preferably between 0.5 and 5 kg/ha.
m e aetive eompound eambinations aeeording to the invention ean be applied either before or after emergen oe of the plants. m ey can also be ineor-porated into the soil before sawing.
The present invention also provides herbieidal eamposition cantaining as active ingredient an active ingredient ccmbinatian of the present invention in admixture with a solid diluent or earrier or in admixture with a liquid diluant or earriar containing a surfaae-activa agent.
The present invention also provides a method of combating weed which camprises applying to the waeds, or to a habitat thereof, a aetive compound camr bination of tha present invention alone or in tha form of a camposition cantain-ing as active ingredient an active compound combination of the present invention in admixture with a diluent or carrier.
The present invantion further provides crops, espaeially cereal crop, protected from damage by weeds by being grown in areas in which immediately prior to and/or during the time of the growing an active compound combination of the present invention was applied alone or in adm~xture with a diluent or carrier.
It will be seen that the usual methods of provid~ng a harvested crop may be improved by the present invention.
The good herbicidal action of the novel active compcund co~binatio~s can be seen from the Examples which follow. Whilst the individual active com-pounds have weaknesses in herbicidal action, the combinations show a very broad action against weeds which goes beyond a simple additive action.
A synergistic effect exists with herbicides whenever the herbicidal action of the active compound combination is greater than that of the individu-ally applied active compounds.
m e action to ke expected for a given combination of two herbicides can be calculated as follows (see OOLBY, S.R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20 - 22, 1967):
If X = ~ damage by herbicide A used in an amount of p kg/ha and Y = ~ damage by herbicide B used in an amount of q kg/ha and E = the expected damage by herbicides A and B used in amounts of p ; and q kg/ha then E = X ~ Y - X . Y.
' ~ 100 If the actual damage is greater than calculated~ the action of the CO~r bination is superadditive, that is to say it exhibits a synergistic effect.
he examples which ~ollow show that the found herbicidal action of the active compound oombinations according to the invention on weeds is greater than ~ the caIculated action, that is to say a genuine synergistic effect exists.
:
~ - 8 -3 :1 ~ 9 Example A
Pre-emergence test Solvent: 5 parts by ~eight of acetone Emulsifier: 1 part by weight of aIkylaryl polyglycol ether To produce a suitable preparation of active compounds, 1 part by weight of the active ccmpound combination was mixed with the stated amount of solvent, the stated D unt of emulsifier was added and the concentrate was diluted with water to the desired concentration.
Seeds of the test plants were sown in normal soil and, after 24 hours, watered with the preparation of the active compounds. It was expedient to keep constant the am~unt of water per unit area. m e total concentration of the active compounds in the preparation was of no importance, only the amount of active compounds applied per unit area being decisive. After three weeks, the degree of damage to the plants was rated in % damage in comparison to the develop-ment of the untreated control. The figures denoted:
0% = no action (like untreated control) 100~ = total destruction The active co~lpounds, amounts applied and results can be seen from the table which follows:
:
_ g _ : .
1~3~
o o o o o o o $
o~ln 'no~l O
.~ ~
~, ~ , 11 ,, ~ ¦ ;~ I . 1 N _~ N ~ ;j N O
: a : ~ - N
b ~ ~ '' ~ H ,~ ~ ~ _ r~
:
~; ';
- '' ' , ' ..
~ ~63109 .Example B
-Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of the active compound ccmbinatio~ was mixed with the stated amount of solvent, the stated amount of emulsifier was added and the concentrate was diluted with water to the desired concentration.
Test plants which had a heig~lt of 5 to 15 cm were sprayed with the pre-p æ ation of the active co~,pounds in such a way as to apply the amounts of active compounds per unit area which were indicated in the table.
m e amount of water applied was 2,000 l/ha. After 3 weeks, the degree of damage to the plants was rated in ~ damage in comp æison to the develcpm~nt of the untreated control.
m e figures denoted:
0% = no action (like untreated control) 100~ = total destruction The acti.ve ccmpcunds, amounts applied and results can be seen from the : table which follows:
l~u I h ~ o u) o o\o ~ h o o o LO o o o !~i ~ o LO o ~ ~ ' ¦ O ~ ~ ¦ o o 4~ o o ~ ~ ~
~ *. ~ ~
~ ~ Lr~ In ~ ~
~ ~ co ~ ~ ~ ~
~¦ --~ ~ '' ~ ^ ' 9 9 ~ u ~ 1~ I
;~ ~ ~ I ~I N
:: _ ~ ~ ~ ~ Z
~ O ~ H ~
.
'
Claims (15)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A herbicidal composition comprising, (I) 1-amino-3-(2,2-dimethylpropyl)-6-ethylthio-1,3,5-triazine-2,4(1H,3H)-dione of the formula and (II) at least one cereal herbicide selected from the group consisting of (1) (a) N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea (chlorotoluron), (b) N'-(4-isopropylphenyl)-N,N-dimethylurea (isoproturon), (c) N'-(3,4-dichlorophenyl)-N-methoxy-N-methylurea (linuron), (d) N-benzothiazol-2-yl-N-methyl-N'-methyl-urea (methabenzthiazuron) and (e) N'-(3-chloro-4-methoxyphenyl)-N,N-dimethyl-urea (metoxuron); (2) (a) S-2,3-dichloroallyl diisopropylthiolcarbamate (diallate) and (b) S-2,3,3-trichloroallyl diisopropylthiolcarbamate (triallate);
(3) (a) ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate (benzoylprop-ethyl), (b) methyl 2-chloro-3-(4 chlorophenyl)-propionate (chlorfenprop-methyl), (c) 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid methyl ester (diclo-fopmethyl), (d) methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate (flamprop-methyl) and (e) isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate (flamprop-isopropyl); (41 (a) 2-methoxy-3,6-dichlorobenzoic acid (dicamba); (5) (a) 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and (b) 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil); or (6) (a) 2-methyl-4,6-dinitrophenol (DNOC), (b) 2,4-dinitro-6-tert.-butyl-phenol (dinoterb) and (c) 2-sec.-butyl-4,6-dinitrophenyl acetate (dinoseb acetate); (7) (a) N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitroaniline (pendimathalin) and (b) N,N-di-(n-propyl)-2,6-dinitro-4-trifluoromethylaniline (trifluralin); (8) (a) 2,4-dichlorophenyl 4-nitrophenyl ether (nitrofen); (9) (a) 2,4-dichlorophenoxy-actic acid (2,4-D), (b) 2,4-dichlorophenoxypropionic acid (2,4-DP), (c) 4-chloro-2-methylphenoxyacetic acid (MCPA) and (d) 2-(2-methyl-4-chlorophenoxy)-propionic acid (MCPP, mecoprop); (10) (a) 2-chloro-4-ethylamino-6-(1-methyl-1-cyanoethyl-amino)-s-triazine (cyanazine), (b) 2-chloro-4,6-bis-(ethylamino)-s-triazine (simazine) and (c) 2-ethylamino-4-methylthio-6-tert.-butylamino-s-triazine (terbutryn); (11) (a) 4-N,N-isobutylimino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (isomethiozin) and (b) 4-amino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (metribuzin); and (12) (a) 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (bentazon) and (b) 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl-sulphate (defenzoquat), the weight ratio of (I) to (II) being from about 1:0.5 to 1:10.
(3) (a) ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate (benzoylprop-ethyl), (b) methyl 2-chloro-3-(4 chlorophenyl)-propionate (chlorfenprop-methyl), (c) 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid methyl ester (diclo-fopmethyl), (d) methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate (flamprop-methyl) and (e) isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate (flamprop-isopropyl); (41 (a) 2-methoxy-3,6-dichlorobenzoic acid (dicamba); (5) (a) 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and (b) 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil); or (6) (a) 2-methyl-4,6-dinitrophenol (DNOC), (b) 2,4-dinitro-6-tert.-butyl-phenol (dinoterb) and (c) 2-sec.-butyl-4,6-dinitrophenyl acetate (dinoseb acetate); (7) (a) N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitroaniline (pendimathalin) and (b) N,N-di-(n-propyl)-2,6-dinitro-4-trifluoromethylaniline (trifluralin); (8) (a) 2,4-dichlorophenyl 4-nitrophenyl ether (nitrofen); (9) (a) 2,4-dichlorophenoxy-actic acid (2,4-D), (b) 2,4-dichlorophenoxypropionic acid (2,4-DP), (c) 4-chloro-2-methylphenoxyacetic acid (MCPA) and (d) 2-(2-methyl-4-chlorophenoxy)-propionic acid (MCPP, mecoprop); (10) (a) 2-chloro-4-ethylamino-6-(1-methyl-1-cyanoethyl-amino)-s-triazine (cyanazine), (b) 2-chloro-4,6-bis-(ethylamino)-s-triazine (simazine) and (c) 2-ethylamino-4-methylthio-6-tert.-butylamino-s-triazine (terbutryn); (11) (a) 4-N,N-isobutylimino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (isomethiozin) and (b) 4-amino-6-tert.-butyl-3-(methylthio)-as-triazin-5(4H)-one (metribuzin); and (12) (a) 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (bentazon) and (b) 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl-sulphate (defenzoquat), the weight ratio of (I) to (II) being from about 1:0.5 to 1:10.
2. A herbicidal composition according to claim 1, in admixture with diluent.
3. A herbicidal composition according to claim 2, which contains from 0.1 to 95% by weight of the total active compounds.
4. A herbicidal composition according to claim 1 or 2, wherein the weight ratio of (I) to (II) is from about 1:0.5 to 1:5.
5, A herbicidal composition according to claim 1 or 2, wherein II is (1a) N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea (chlorotoluron).
6. A herbicidal composition according to claim 1 or 2, wherein II is (1b) N'-(4-isopropylphenyl)-N,N-dimethylurea (isoproturon).
7. A herbicidal composition according to claim 1 or 2, wherein II is (1d) N-benzothiazol-2-yl-N-methyl-N'-methylurea (methabenzthiazuron).
8. A method of combating weeds comprising applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition according to claim 1 or 2.
9. A method according to claim 8 wherein the composition is applied as a pre-emergent herbicide to a field wherein a cereal crop is grown.
10. A method according to claim 8 wherein the composition is applied as a post-emergent herbicide to a field wherein a cereal crop is grown.
11. A method according to claim 8, 9 or 10 wherein component II in the composition is (1a) N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea (chlorotoluron).
12. A method according to claim 8, 9 or 10 wherein component II in the composition is (1b) N'-(4-isopropylphenyl)-N,N-dimethylurea (isoproturon).
13. A method according to claim 8, 9 or 10 wherein component II in the composition is (1d) N-benzothiazol-2-yl-N-methyl-N'-methylurea (metha-benzthiazuron).
14. A method according to claim 8, 9 or 10 wherein the composition is applied to an area of agriculture in an amount of 0.2 to 8 kg per hectare.
15. A method according to claim 8, 9 or 10 wherein the composition is applied to an area of agriculture in an amount of 0.5 to 5 kg per hectare.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803043977 DE3043977A1 (en) | 1980-11-21 | 1980-11-21 | Synergistic selective herbicidal compsn. for cereal crops - contg. 1-amino -triazin-di:one deriv. and second herbicide |
| DEP3043977.1 | 1980-11-21 | ||
| DEP3127861.2 | 1981-07-15 | ||
| DE19813127861 DE3127861A1 (en) | 1981-07-15 | 1981-07-15 | Selective herbicides based on triazinedione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163109A true CA1163109A (en) | 1984-03-06 |
Family
ID=25789239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000390558A Expired CA1163109A (en) | 1980-11-21 | 1981-11-20 | Selective herbicidal agents based on a triazinedione |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0052825B1 (en) |
| AR (1) | AR229108A1 (en) |
| AU (1) | AU7715981A (en) |
| BR (1) | BR8107549A (en) |
| CA (1) | CA1163109A (en) |
| DE (1) | DE3162391D1 (en) |
| DK (1) | DK516681A (en) |
| GR (1) | GR78223B (en) |
| IL (1) | IL64305A0 (en) |
| PT (1) | PT73961B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5173104A (en) * | 1989-11-10 | 1992-12-22 | Bayer Aktiengesellschaft | Selectively herbicidal metribuzin plus bromoxynil |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2120355B1 (en) * | 1996-03-07 | 1999-07-01 | Aragonesas Agro S A | HERBICIDAL, STABLE AND CONCENTRATED SUSPENSION OF TERBUTRINE AND PROMETRINE, AND PREPARATION PROCEDURE. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254200C2 (en) * | 1972-11-06 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Tetrahydro-1,3,5-triazine-2,6-diones, process for their preparation and their use as herbicides |
-
1981
- 1981-11-06 AU AU77159/81A patent/AU7715981A/en not_active Abandoned
- 1981-11-07 DE DE8181109564T patent/DE3162391D1/en not_active Expired
- 1981-11-07 EP EP81109564A patent/EP0052825B1/en not_active Expired
- 1981-11-11 PT PT73961A patent/PT73961B/en unknown
- 1981-11-17 AR AR287478A patent/AR229108A1/en active
- 1981-11-18 IL IL64305A patent/IL64305A0/en unknown
- 1981-11-19 GR GR66568A patent/GR78223B/el unknown
- 1981-11-20 CA CA000390558A patent/CA1163109A/en not_active Expired
- 1981-11-20 DK DK516681A patent/DK516681A/en not_active Application Discontinuation
- 1981-11-20 BR BR8107549A patent/BR8107549A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5173104A (en) * | 1989-11-10 | 1992-12-22 | Bayer Aktiengesellschaft | Selectively herbicidal metribuzin plus bromoxynil |
Also Published As
| Publication number | Publication date |
|---|---|
| GR78223B (en) | 1984-09-26 |
| EP0052825A1 (en) | 1982-06-02 |
| AU7715981A (en) | 1982-05-27 |
| PT73961A (en) | 1981-12-01 |
| IL64305A0 (en) | 1982-02-28 |
| DE3162391D1 (en) | 1984-03-29 |
| PT73961B (en) | 1983-04-18 |
| AR229108A1 (en) | 1983-06-15 |
| EP0052825B1 (en) | 1984-02-22 |
| BR8107549A (en) | 1982-08-17 |
| DK516681A (en) | 1982-05-22 |
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