GB2315413A - Synergistic herbicidal compositions based on N-isopropyl-N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide - Google Patents
Synergistic herbicidal compositions based on N-isopropyl-N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide Download PDFInfo
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- GB2315413A GB2315413A GB9714993A GB9714993A GB2315413A GB 2315413 A GB2315413 A GB 2315413A GB 9714993 A GB9714993 A GB 9714993A GB 9714993 A GB9714993 A GB 9714993A GB 2315413 A GB2315413 A GB 2315413A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/13—Oxygen 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
- A01N43/72—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
- A01N43/82—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 five-membered rings with three ring hetero atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Novel synergistic herbicidal combinations of N-isopropyl-N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yl oxy)acetamide(I) with fenoxaprop-ethyl(II) and/or clodinafop-propargyl(III) are disclosed.
Description
HeXicidal compositions based on N - isopropyl- N - ( fluonsphenyl)(S nifluoromethyl- 1.3.4- thiadiazol- 2-yloxy)acetamide The invention relates to novel synergistic herbicidal combinations of a known
hetaryloxyacetamide with other known herbicides belonging to other classes
which can be used particularly advantageously for selective weed control in a
variety of crop plants.
The patents listed below describe hetaryloxyacetamides which are particularly
active against monocotyledonous weeds (= grass weeds), but additionally also
act against some dicotyledonous weeds. They are virtually exclusively soil-acting
and have little foliar activity, and some ofthem are very selective in mono- and
dicotyledonous crop plants such as cereals, maize, rice, soybeans and cotton [cf. for example EP-A 5 501 (= US 4 509 971 and US 4 833 243); EP-A 18 497
(= US 4 645 525 and US 4 756 741); EP-A 29 171 (= US 4 408 055); EP-A 94
514 (= US 585 471); EP-A 100 044 (= US 4 549 899); EP-A 100 045 (= US 4 540 430); EP-A 161 602 (= US 4 784 682); EP-A 195 237 (= US 4 788 291);
DE-A 3 724 467; EP-A 348 734 (= US 4 988 380); EP-A 348 737 (= US 4 968
342 and 5 090 991); DE-A 4 113 421 and DE-A 4 137 827; and also WO
91/06544].
In addition, DE 4 223 465 describes synergistic mixtures of hetaryloxyacetamides with Nphenylureas, Nbenzothiazo lylureas, 2,6-dinitroanilines, s-triazines, as-triazinones, sulfonylureas, imidazolinones, pyridinecarboxamides and diphenyl ethers. However, none of the mixtures described therein has as yet achieved any practical significance. A disadvantage of the mixtures described in DE 4 223 465 is that their action is not always distinct in case of strong overgrowth by a variety of weeds.
It is an object ofthe present invention to provide on the basis of N-isopropyl N -(4-uorophenyl)(5-trifluoromethyl- 1,3,4-thiadiazol-2-yloxy)acetamide of the formula (I)
novel synergistic herbicidal mixtures which are superior in their activity to prior art mixtures and additionally act against a broad spectrum of weeds.
This object is achieved by combinations of known herbicides with the active compound of the formula a) surprisingly found, in biological tests, to show pronounced synergistic effects with regard to activity against weeds and to be especially advantageously useful as effective broad range combination products for the selective control of weeds - both of monocotyledonous and of dicotyledonous weeds by the preemergence'and post-emergence method'- in monocotyledonous and dicotyledonous crop plants, such as, for example, maize, wheat, barley, rice, soybeans and sunflowers, allowing the effective control of a number of economically important (problem) weeds and grass weeds.
The present invention accordingly provides synergistic herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination of N - isopropyl-N - (4- fluorophenyl)(5- trifluoromethyl- 1,3,4 thiadiazol- 2-yloxy)acetamide of the formula (I)
and at least one herbicidally active compound of the formula (II) or (III) (a)
(II) fenoxaprop-ethyl
(III) clodinafop-propargyl The compound of the formula (I) is known from EP-A 348 737 and US 4 968 342.
Fenoxaprop-ethyl is ethyl 2-[4-(6-chlorobenzoxazol-2-yl)oxyphenoxy]pro- pionate, described in DE 2 640 730.
Clodinafop-propargyl is propinyl (R)-2- [4- [(5- chloro- 3- fluoropyridin-2-yl)- oxy]phenoxy]propionate, disclosed in EP-A 248 968.
Hetaryloxyacetamides including the active compound of the formula (I) are particularly active against monocotyledonous weeds (= grass weeds), but additionally also act against some dicotyledonous weeds.
The active compounds (II) and (III) mentioned can be used for the selective control of a broad spectrum of grass weeds in economically important crop plants such as, for example, cereals, maize, soybeans, cotton, beet and rice.
However, their activity against certain harmful monocotyledons is not always satisfactory. Important problem weeds, such as, for example, Apera spica-venti, are often not sufficiently controlled.
Surprisingly, it has now been found that the active compound combinations of the hetaryloxyacetamide of the formula (I) and the active compounds (II) and/or (III) defined above have a particularly high activity and can be used selectively in many crop plants.
Surprisingly, the herbicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds.
This means that not merely a complementation of action is present, but a true synergistic effect, which was unforeseeable. The novel active compound combinations are well tolerated by many crop plants, and even weeds which are otherwise difficult to control, such as Apera spica-venti, are controlled well by the novel active compound combinations. The novel active compound combinations are therefore a useful addition to the range of the selective herbicides.
The active compound combinations according to the invention can be used for example in connection with the following plants:
Dicotvledonous crop plants ofthe genera: Gossypium, Glycine, Beta, Daucus,
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vlcia, Nicotiana, Lycopersicon,
Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotvledonous weeds of the genera: Echinochloa, Setaria, Panicum,
Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena,
Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria,
Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium,
Agrostis, Alopecurus and Apera.
Monocotvledonous crop plants ofthe genera: Oryza, Zea, Triticum, Hordeum,
Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, 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 manner to other plants.
The synergistic effect of the active compound combinations according to the invention is especially pronounced at specific concentration ratios. However.
the weight ratios ofthe active compounds in the active compound combinations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, especially preferably 0.1 to 30 parts by weight, of active compound of the formula (II) and/or (III) are used per part by weight of active compound of the formula (I).
The active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam- formers.
If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals. and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolyzates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuff; and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
In general, the active compound combinations according to the invention are applied in the form of ready mixes. However, the active compounds in the active compound combinations can also be formulated individually and mixed upon application, that is to say applied in the form of tank mixes.
The new active compound combinations as such or in the form of their formulations can also be used as mixtures with further known herbicides, finished formulations or tank mixes again being possible. Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth promoters, plant nutrients and soil conditioners, are also possible. Furthermore, it may be advantageous for specific purposes, in particular when using the post-emergence method, to incorporate mineral or vegetable oils tolerated by plants (for example "Oleo Dupont liE', which is commercially available) or ammonium salts such as, for example, ammonium sulfate or ammonium thiocyanate, as further additives in the formulations.
The novel active compound combinations according to the invention can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, dusting or spreading.
The rates of application of the active compound combinations according to the invention can be varied within a certain range; they depend, inter alia, on the weather and on the condition of the soil. In general, the rates of application are between 0.01 and 10 kg per ha, preferably between 0.03 and 5 kg per ha, in particular between 0.05 and 3.0 kg per ha.
The active compound combinations according to the invention can be applied before and after the emergence of the plants, i.e. by the preemergence and post emergence method
The good herbicidal activity of the novel active compound combinations is evident from the examples below. While the individual active compounds show weaknesses in their herbicidal activity, the combinations all exhibit very efficient control of weeds, and this control exceeds a simple sum of the activities.
In herbicides, a synergistic effect is always present when the herbicidal activity of the active compound combination exceeds that of the active compounds applied individually.
The expected activity for a given combination of two herbicides can be calculated as follows (cf. Colby, S. R.; "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
If X= % damage by herbicide A (active compound of group 1) at
the rate of application of p kg/ha and
Y= % damage by herbicide B (active compound of group 2) at
the rate of application of q kg/ha and
E = the expected damage caused by herbicides A and B at a
rate of application of p and q kg/ha,
If the actual damage exceeds the calculated value, the combination is superadditive with regard to its activity, i.e. it shows a synergistic effect.
The examples below reveal that the herbicidal activity of the active compound combinations accordingto the invention found exceeds the calculated value, i.e.
that the novel active compound combinations have a synergistic action.
Use Examples
To prepare the active compound preparations required for the tests, suitable amounts of a water-dispersible powder formulation (WP) of the hetaryloxyacetamide of the formula (I) and a commercially available formulation ofthe compounds (II) and/or (III), respectively, are weighed out and diluted with water to the desired concentration; by mixing, various combinations of the two active compounds were prepared.
A) Post-emergence tests/greenhouse
Test plants which have a height of 5 to 15 cm are sprayed with the active
compound preparations in such a way as to apply the particular amounts
of active compound desired per unit area. The concentration ofthe spray
liquor is chosen such that the particular amounts of active compound
desired are applied in 500 1 of water per ha. After the treatment, the test
plants are kept in the greenhouse under controlled conditions
(temperature, atmospheric humidity, light) until the evaluation. After
three weeks, the degree of damage to the plants is rated in % damage in
comparison to the development of untreated control plants.
The figures denote:
0% = no action/damage (like untreated control)
100% = total destruction
Active compounds, application rates and results are listed in the tables
below.
Table 1 Herbicidal activity of (I), clodinafop-propargyl and tank mixes of
(I) and clodinafop-propargyl against Apera spica-venti by the
post-emergence method
Preparation Application rate herbicidal activity in % g of a.i./ha Apera spica-venti found caic.
(1) 60 40 (I) 30 40 (I) 15 20 Clodinafop-propargyl 30 10 Clodinafop-propargyl 15 0 (I)+ 60 80 46 Clodinafop-propargyl + 30 (I)+ 30 70 46 Clodinafop-propargyl + 30 (I) + 15 50 28 Clodinafop-propargyl + 30 (I) + 60 60 40 Clodinafop-propargyl + 15 (I)+ 30 50 40 C lod in afop- propargyl + 15 (I)+ 15 30 20 Clodinafop-propargyl + 15 Table2 Herbicidal activity of(I), fenoxaprop-ethyl and tank mixes of (I)
and fenoxaprop-ethyl against Apera spica-venti by the post
emergence method
Preparation Application rate herbicidal activity in g of a.i./ha Apera spica-venti found calc.
(I) 60 40 Fenoxaprop-ethyl 30 20 Fenoxaprop-ethyl 15 0 (I)+ 60 60 52 Fenoxaprop-ethyl + 30 (I)+ 60 50 40 Fenoxaprop-ethyl + 15 Notes to Tables 1 and 2 found = activity or damage (in percent) found; calc. = activity or damage (in percent) calculated using the COLBY
formula above a.i. = active ingredient
The compounds fenoxaprop-ethyl (II) und clodinafoppropargyl (III) have been used in form of the following commercially available formulations: (II) as (R)RALON 060 EW (emulsion-in-water) (AgrEvo); (III) as ( )TOPIC 240 EC (emulsion concentrate)(Novartis).
Claims (7)
1. Synergistic herbicidal compositions, characterized in that they comprise
an effective amount of an active compound combination ofN-isopropyl- N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-
2
yloxy)acetamide ofthe formula (I)
and at least one herbicidally active compound ofthe formula (II) or (III)
(II) Fenoxaprop-ethyl and/ or
(III) Clodinafop-propargyl 2. Synergistic herbicidal compositions according to Claim 1, characterized
in that 0.001 to 1000 parts by weight of active compound of the formula (II) and/or (III) are employed per part by weight of N-isopropyl-N-(4.
fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide (I).
3. Synergistic herbicidal compositions according to Claim 1, characterized
in that 0.01 to 100 parts by weight of active compound of the formula
(II) and/or (III) are employed per part by weight of active compound of
the formula (I).
4. Synergistic herbicidal compositions according to Claim 1, characterized
in that 0.1 to 30 parts by weight of active compound of the formula (II) and/or (III) are employed per part by weight of active compound of the
formula (I).
5. Method of controlling weeds, characterized in that an active compound
combination according to Claims 1 to 4 is allowed to act on weeds and/or their habitat.
6. Use of active compound combinations according to Claims 1 to 4 for
controlling weeds.
7. Process for preparing herbicidal compositions, characterized in that an
active compound combination according to Claims 1 to 4 is mixed with
extenders and/or surfactants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19628777 | 1996-07-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9714993D0 GB9714993D0 (en) | 1997-09-24 |
| GB2315413A true GB2315413A (en) | 1998-02-04 |
| GB2315413B GB2315413B (en) | 2000-03-08 |
Family
ID=7800045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9714993A Expired - Fee Related GB2315413B (en) | 1996-07-17 | 1997-07-16 | Herbicidal compositions based on N-isopropyl-N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN1081440C (en) |
| CA (1) | CA2210273C (en) |
| DE (1) | DE19728568B4 (en) |
| FR (1) | FR2751174B1 (en) |
| GB (1) | GB2315413B (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1209972B1 (en) * | 1999-09-07 | 2003-05-28 | Syngenta Participations AG | Herbicidal composition |
| CA2382435C (en) | 1999-09-07 | 2009-02-03 | Syngenta Participations Ag | Novel herbicidally active phenyl-substituted heterocycles |
| DE19947918A1 (en) * | 1999-10-06 | 2001-04-12 | Bayer Ag | Selective herbicides based on pyrimidine derivatives |
| HUP0301968A3 (en) * | 1999-11-17 | 2004-06-28 | Bayer Ag | Selective and synergistic herbicide compositions containing 2,6-disubstituted pyridine derivatives, preparation and use thereof |
| AU6593601A (en) * | 2000-05-22 | 2001-12-03 | Bayer Ag | Selective heteroaryloxy-acetamide-based herbicides |
| DE10041619A1 (en) * | 2000-05-22 | 2001-11-29 | Bayer Ag | Selective herbicides based on heteroaryloxyacetamides |
| AR036580A1 (en) * | 2001-09-27 | 2004-09-15 | Syngenta Participations Ag | HERBICIDE COMPOSITION |
| JP4624801B2 (en) * | 2002-11-21 | 2011-02-02 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Herbicidal composition |
| CN101700023B (en) * | 2009-10-21 | 2012-07-25 | 张志高 | Clodinafop-propargyl and fenoxaprop-p-ethyl herbicide composition |
| CN101715768B (en) * | 2009-12-08 | 2013-07-17 | 安徽丰乐农化有限责任公司 | Clodinafop-propargyl fenoxaprop compound herbicide |
| CN102239854A (en) * | 2011-05-18 | 2011-11-16 | 利尔化学股份有限公司 | Weeding pesticide composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640730C2 (en) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy and benzothiazolyloxyphenoxy compounds and herbicidal agents containing them |
| CH679396A5 (en) * | 1986-06-12 | 1992-02-14 | Ciba Geigy Ag | |
| DE4223465A1 (en) * | 1992-07-16 | 1994-01-20 | Bayer Ag | Herbicidal agents based on heteroaryloxyacetamides |
| EP0614608B1 (en) * | 1993-02-18 | 1999-01-07 | Hoechst Schering AgrEvo GmbH | Synergistic mixture for control of blackgrass |
| DE4317323A1 (en) * | 1993-05-25 | 1994-12-01 | Bayer Ag | N- (4-fluoro-phenyl) heteroaryloxyacetamide |
| DE4428982C1 (en) * | 1994-08-16 | 1996-05-15 | Hoechst Schering Agrevo Gmbh | Selective herbicide, esp. for foxtail millet control in crops |
| DE19546751B4 (en) * | 1994-12-23 | 2005-02-17 | Bayer Cropscience Ag | Selective herbicides based on heteroaryloxy-acetamides |
-
1997
- 1997-07-04 DE DE19728568A patent/DE19728568B4/en not_active Expired - Lifetime
- 1997-07-14 CA CA 2210273 patent/CA2210273C/en not_active Expired - Lifetime
- 1997-07-16 GB GB9714993A patent/GB2315413B/en not_active Expired - Fee Related
- 1997-07-16 FR FR9709008A patent/FR2751174B1/en not_active Expired - Lifetime
- 1997-07-17 CN CN97117976A patent/CN1081440C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE19728568A1 (en) | 1998-01-22 |
| CN1081440C (en) | 2002-03-27 |
| GB9714993D0 (en) | 1997-09-24 |
| FR2751174A1 (en) | 1998-01-23 |
| CN1179885A (en) | 1998-04-29 |
| CA2210273C (en) | 2007-10-02 |
| FR2751174B1 (en) | 2000-04-07 |
| GB2315413B (en) | 2000-03-08 |
| CA2210273A1 (en) | 1998-01-17 |
| DE19728568B4 (en) | 2007-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20080716 |