WO2005087006A1 - Unkrautbekämpfungsverfahren - Google Patents

Unkrautbekämpfungsverfahren Download PDF

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Publication number
WO2005087006A1
WO2005087006A1 PCT/EP2005/001735 EP2005001735W WO2005087006A1 WO 2005087006 A1 WO2005087006 A1 WO 2005087006A1 EP 2005001735 W EP2005001735 W EP 2005001735W WO 2005087006 A1 WO2005087006 A1 WO 2005087006A1
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Prior art keywords
methyl
compound
formula
plants
active
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PCT/EP2005/001735
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English (en)
French (fr)
Inventor
Markus Dollinger
Frederic Top
Ernst Rudolf Gesing
Erwin Hacker
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Bayer Cropscience Ag
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Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to EA200601550A priority Critical patent/EA011162B1/ru
Priority to US10/591,673 priority patent/US20080020932A1/en
Priority to BRPI0508458-0A priority patent/BRPI0508458A/pt
Priority to CA002558322A priority patent/CA2558322A1/en
Priority to AU2005220617A priority patent/AU2005220617A1/en
Priority to EP05715411A priority patent/EP1725106A1/de
Publication of WO2005087006A1 publication Critical patent/WO2005087006A1/de

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    • 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<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the use of the known compound 4 - [[[(3-methoxy-4,5-dihydro-4-methyl-5-oxo-lH-l, 2,4-triazol-l-yl) carbonyl] -a ⁇ - ⁇ tno] -sulfonyl] -5-met yl-tMophen-3-carboxylic acid methyl ester (alias 5-methoxy-4-me1-yl-2r [(4-methoxycarbonyl-2-methyl-t-ienien-3-yl ) -sulfonyl- a ino-carbonyl] -2,4-dihydro-3H-l, 2,4-triazol-3-one; 'compound of the formula (I) ”) - and their salts, especially their sodium salt, for selective Control of problem weeds of the genus Apera in crop plants, in particular for combating these weeds in cereals and maize crops.
  • Substituted Thienylsulfonylaminoc - rbonyltriazolinone, - and salts thereof, processes for manufacturing position of these compounds and their utility as herbicides, are the subject of elderly • patent applications (see WO 01/05788, WO 03/026427, WO 03/026426.).
  • the substituted thienylsulfonylaminocarbonyltriazolinones described in these patent applications in addition to the compound of the formula (I) have a molecular structure which is very similar to the compound of the formula (I) to be used according to the invention, but have - in contrast to this - certain ' herbaceous prawns, such as. B.
  • Apera species still weaknesses or gaps in effectiveness.
  • the invention also provides the use of the compound 5-methoxy-4-methyl-2 - [(4-meth- oxyC' arbonyl-2-methyl-1hden-3-yl) sulfonyl-to ⁇ no-carbonyl] -2 , 4-dihydro-3H-l, 2,4-1riazol-3-one of the formula (I)
  • the invention further relates to a method for the selective control of weeds of the genus Apera in crops of useful plants, in particular cereal crops, in particular as in wheat crops, or corn crops, which is characterized in that the compound of the formula (I) and or salts of the compound of formula (I) is applied together with surface-active agents and / or customary extenders in crops of crops, crops of cereals or maize.
  • the compound of formula (I) is known (cf. WO 01/05788).
  • the compound of formula (I) shows broad herbicidal activity. It can also be used to control the following weeds, especially in maize and cereal crops:
  • the compound of formula (I) and its salts show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. They are suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops, especially in cereals, in particular in wheat, and also corn crops both in the pre-emergence and in the post-emergence process.
  • a safener can be added to the herbicidal compositions which comprise the compound of the formula (I) in order to increase the compatibility with crop plants.
  • the following groups of compounds are particularly suitable as safeners:
  • dichlorophenylpyrazole carboxylic acid preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S 1-2), 1- (2,4-dichlorophenyl) -5-isopropyl -pyrazole-3-carboxylic acid ethyl ester (S 1-3), l- (2,4-dichlorophenyl) -5- (l, l-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S 1-4), Ethyl l- (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylate (S 1-5) and related compounds as described in EP-A-333 131 and EP-A-269 806.
  • Preferred safeners are benoxacor, mefenpyr, fenchlorazole, isoxadifene, cloquintocet and their -CC-alkyl esters, in particular benoxacor (S 4-1), mefenpyr-diethyl (S 1-1), fenchlorazol-ethyl (S 1-6), isoxadifene -ethyl (S 1-9), Cloquintocet-mexyl (S 2-1), and (S 3-1).
  • Profluazol B.209, Prof ⁇ xydi (B.210), Prometryn (B.211), Propachlor (B .212), Propanil (B.49), Propaquizafop (B.213), Propisochlor (B.214), Propoxycarbazone-sodium (B.215), Propyzamide (B.216), Prosulfocarb (B.217), Prosulfuron ' (B.218), pyraclonil (B.219) (l- (3-chloro-4,5,6i7-tetrahydropyrazolo [l, 5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -lH-pyrazole-4-carbonitrile known from WO 94/08999), pyraflufen-ethyl (B.220), pyrazolates (B.221), pyrazosulfuron-ethyl (B.222),
  • WO-A-92/10660 N - [[(4,6-dimethoxy-2-pyrinidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino) -2 -pyridine sulfonamide (B.266), (see WO-A-92/10660), 4- (4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-1H-1, 2,4-triazole - 1 -yl) -2- (ethylsulfonylamino) -5-fluoro-benzenecarbothioide (B.
  • L-glufosinate (B.277) and bilanafos (B. 279) have the following formulas (L-phosphinothricin, L-glufosinate)
  • the combinations with the mixing partners are distinguished by the fact that the compound of the formula (I) - when used together with the known herbicidally active compounds from - different substance groups show pronounced synergistic effects with regard to the action against weeds and / or that the crop plant tolerance is significant improve and can be used particularly advantageously as a broadly effective combination preparations for the selective control of weeds in Nut ⁇ flanzenkulttiren, such as in cotton, barley, corn, potatoes, rice, soybeans, sunflowers, wheat and sugar cane, especially wheat and corn.
  • the herbicidal activity of the active compound combinations according to the invention composed of the compound of the formula (I) and the listed mixing partners is considerably higher than the sum of the effects of the individual active compounds.
  • the active ingredient combinations are well tolerated in many crops, the active ingredient combinations also combating weeds which are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • 1 part by weight of active compound of the formula (I) is preferably from 0.05 to 100 parts by weight. parts of the mixed partners.
  • the mixtures particularly preferably contain 0.1 to 10 parts by weight of the mixing partners per 1 part by weight of active compound of the formula (I).
  • a herbicide always has a synergistic effect if the herbicidal action of the active compound combination is greater than that of the individual active compounds applied.
  • X % damage by herbicide A (active ingredient of the formula I) at a rate of p kg / ha
  • Y % damage by herbicide B (active ingredient of the formula II) at q kg / ha application rate
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • the active compound combinations comprising the compound of the formula (I) and other known herbicides and / or safeners indeed have the property that the herbicidal action found is stronger than the calculated one, that is to say that the active compound combinations act synergistically.
  • a + (B.248) A + (B.249) A 4- (B.250) A 4- (B.251) A - (B.252) A + (B.253) ; A + (B.254), A + (B.255) A + (B.256) A 4- (B.257) ; A 4- (B.258) A 4- (B.259) A + (B.260) A + (B.261), A + (B.262) A 4- (B.263) A 4- ( B.264) A 4- (B.265) A - (B.266) A + (B.267), A 4- (B.268), A + (B.269), A 4- (B.250) A 4- (B.251) A - (B.252) A + (B.253) ; A + (B.254), A + (B.255) A + (B.256) A 4- (B.257) ; A 4- (B.258) A 4- (B.259) A + (B.260) A + (B.26
  • S 3-1 The following two combinations with safener (S 3-1) are particularly suitable as particularly suitable agents (compound of the formula (I) - A): A 4- (S 3-1), A 4- (Bl) 4- (S 3-1), A 4- (B.2) 4- (S 3-1), A 4- (B.3) 4- (S 3-1), A + (B.4) + (S 3-1), A + (B.5) 4- (S 3-1), A 4- (B.6) 4- (S 3-1), A 4- (Bl) + (S 3-1), A 4- (B.8) 4- (S 3-1), A 4- (B.9) 4- (S 3-1), A 4- (B.10) + ' (S 3-1), A 4- (B.ll) + (S 3-1), A + (B.12) 4- (S 3 -1), A 4- (Bl 3) 4- (S 3-1), A + (B.14) 4- (S 3-1), A 4- (B.15) 4- (S 3- 1), A 4- (B.16) 4- (S 3-1), A 4- (B.17) 4- (S 3-
  • the compound of the formula (I) can be used in all of the two combinations explicitly listed above with and without the addition of safener . can also be replaced by their salts, preferably their sodium salt of the formula (Ia).
  • a 4- Pinoxaden or A 4- Pinoxaden 4- Cloquintocet-mexyl should be most emphasized.
  • a herbicidal composition consisting of a combination of active compounds comprising the compound A and pinoxades and, if appropriate, the safener Cloquintocet-mexyl is particularly suitable in the process according to the invention and also for controlling Avena species.
  • compositions are not already specifically disclosed in WO 03/026426, all herbicidal compositions comprising the above-mentioned active ingredient combinations are also the subject of the present application.
  • active ingredients of the active ingredient combinations explicitly listed above can be combined (e.g. as a tank mix), but also sequentially in pre-sowing, pre-emergence (after sowing) -, post-emergence (1-2 sheets), post-emergence (2-4-sheets) and post-emergence (6-sheet) stage are used, this results, for example, in the following generalized application scheme:
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood as meaning plants having certain properties ( "traits") which have been obtained by conventional breeding, by mutagenesis or else by recombinant 'e DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of activity and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemical active compounds, better growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of crops against dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products, which are beyond those actually expected Effects go beyond.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and / or higher quality Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial.
  • Pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the traits that are particularly emphasized are the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b ), Cry ⁇ A (c), CryHA, CrylüA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example hnidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinothricin, e.g. rapeseed), IMI® ( Tolerance to hnidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearf ⁇ eld® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously with the compound of the general formula (I), the in addition to the good control of the weed plants.
  • above-mentioned synergistic effects with the transgenic plants or plant varieties occur.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the compound of formula (I) and the mixtures containing this compound can be converted into the usual formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients Natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic compounds such as chlorobenzenes
  • chlorinated aliphatic compounds such as chloroethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins
  • petroleum fractions mineral and vegetable oils
  • alcohols such as Butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and 'synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
  • emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates,. Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the compound of the formula (I) and its salts 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 usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the compound of formula (I) and its salts can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g (preferably 8 g) and 125 g of active ingredient of the formula (I) per hectare of soil, preferably between 2 g and 60 g per ha, particularly preferably 10 g and 30 g per ha. The most preferred according to the invention Application rate 10 g to 15 g per ha should be mentioned.
  • the particularly advantageous effect of the tolerance of crop plants of the active substance combinations which can be used in the process according to the invention, with the addition of safener is particularly pronounced at certain concentration ratios.
  • the weight ratios of the compound of the formula (I) to the safener can be varied within relatively wide ranges. 1 to 25 parts by weight of the safener and particularly preferably 3 to 6 parts by weight of safener are preferably present in 1 part by weight of active compound of the formula (I).
  • the compound of formula (I) was tested under field conditions in winter wheat in Germany and Tru against the economically important weed Apera spica-venti.
  • the small parcel experiments were set up on cultivated areas of agricultural practice, whereby the cultivation and weather conditions can be viewed as representative over the examination period. Areas with a particularly high weed population were preferred.
  • the active ingredient was applied extensively in the post-emergence (spring) spraying process with medium droplet size.
  • the active compound was formulated as 10 WP (10% w / w water-dispersible powder), mixed with the safener mefenpyr-diethyl as 15 WG (15% w / w water-dispersible granulate) and with alkyl ether sulfate as an additive, and mixed with practical water application rates applied.

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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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  • Engineering & Computer Science (AREA)
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Abstract

Die vorliegende Erfindung betrifft die neue Verwendung der Verbindung 5-Methoxy-4-methyl-2-[(4-methoxycarbonyl-2-methyl-thien-3-yl)-sulfonyl-amino-carbonyl]-2,4-dihydro-3H-1,2,4-triazol-3-on der Formel (I) und/oder an Salzen der Verbindung der Formel (I) zur selektiven Bekämpfung von Unkräutern der Gattung Apera in Nutzpflanzenkulturen sowie das entsprechende landwirtschaftliche Verfahren.

Description

ünkrautbekämpfungsverfahren
•Die Erfindung betrifft die Verwendung der bekannten Verbindung 4-[[[(3-Methoxy-4,5-dihydro-4- methyl-5-oxo-lH-l,2,4-triazol-l-yl)-carbonyl]-aι-ιtno]-sulfonyl]-5-met yl-tMophen-3-carbonsäure methylester (alias 5-Methoxy-4-me1- yl-2r[(4-methoxycarbonyl-2-methyl-t-ιien-3-yl)-sulfonyl- a ino-carbonyl]-2,4-dihydro-3H-l,2,4-triazol-3-on; 'Nerbiήdung der Formel (I)") - sowie ihrer Salze, insbesondere ihres Νatriumsalzes, zur selektiven Bekämpfung von Problemunkräutern der Gattung Apera in Νutzpflanzenkulturen, insbesondere zur Bekämpfung dieser Unkräuter in Getreide- und Maiskulturen.
Substituierte Thienylsulfonylaminoc--rbonyltriazolinone,- sowie deren Salze, Verfahren zur Her- Stellung dieser Verbindungen und ihre Verwendbarkeit als Herbizide, sind Gegenstand von älteren •Patentanmeldungen (vgl. WO 01/05788, WO 03/026427, WO 03/026426). Die in diesen Patentanmeldungen neben der Verbindung der Formel (I) beschriebenen substituierten Thienylsulfonyl- aminocarbonyltriazolinone haben eine zur erfindungsgemäß zu verwendenden Verbindung der Formel (I) sehr ähnliche Molekülstruktur, weisen jedoch - im Gegensatz zu dieser - bei bestimmten ' Urikrautpflaiizen, wie z. B. Apera-Arten noch Wirkungsschwächen oder Wirkungslücken auf.
- Überraschenderweise wurde nun gefunden, dass gerade die Verbindung der Formel (I), insbesondere bei Verwendung zusammen mit einem Safener, bei sehr guter Verträglichkeit gegenüber Getreidearten, wie insbesondere Weizen, und gegenüber Maisarten im Vergleich mit den oben genannten strukturell ähnlichen Verbindungen, erheblich stärkere Wirkung gegen einige schwer be- kämpfbare Unkräuter der Gattung Apera in Getreidekulturen oder Maiskulturen aufweist und somit zur effizienten und selektiven Bekämpfung von Unkräutern der Gattung Apera, insbesondere in Weizen und Mais, besonders gut geeignet ist. Die bei den obengenannten, mit der Verbindung der Formel (I) eng verwandten Vergleichsverbindungen beobachteten Wirkungslücken treten im Ui-lcrautspektrum der Verbindung der Formel (I) und ihrer Salze nicht auf.
' Gegenstand der Erfindung ist die Verwendung der Verbindung 5-Methoxy-4-methyl-2-[(4-meth- oxyc'arbonyl-2-methyl-1hden-3-yl)-sulfonyl-anήno-carbonyl]-2,4-dihydro-3H-l,2,4-1riazol-3-on der Formel (I)
Figure imgf000002_0001
und oder der Salze der Verbindung der Formel (I) zur selektiven Bekämpfung von Unkräutern der Gattung Apera m Nutzpflanzen- lturen, insbesondere Getreidekulturen, wie in Weizenkulturen, oder Maiskulturen.
Gegenstand der Erfindung ist weiter ein Verfahre'n zur selektiven Bekämpfung von Unkräutern der Gattung Apera in Nutzpflanzenkulturen, insbesondere Getreidekulturen, insbesondere wie in Weizenkulturen, oder Maiskulturen, welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel (I) und oder Salze der Verbindung der Formel (I) zusammen mit oberflächenaktiven Mitteln und/oder üblichen Streckmitteln in Nutzpflanzenkulturen, Getreidekulturen oder Maiskulturen appliziert.
Die Verbindung der Formel (I) ist bekannt (vgl. WO 01/05788).
Die Verbindung der Formel (I) zeigt eine breite herbizide Wirksamkeit. Sie kann ebenfalls zur Bekämpfung der folgenden Unkräuter, insbesondere in Mais- und Getreidekulturen, verwendet werden:
Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanu , Rorippa, Rotala, Lindeπiia, La ium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Monokotyle Unkräuter der Gattungen: 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, Aegüops, Phalaris.
Die Verwendung der Verbindung (I) und ihrer Salze ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.
Die Verbindung der Formel (I) sowie ihre Salze zeigen starke herbizide Wirksamkeit und ein breites Wirk-mgsspektrum bei Anwendung auf dem Boden und auf oberirdische Pflanzenteile. Sie eignen sich zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in monokotylen Kulturen, vor allem in Getreide, insbesondere in Weizen, als auch Maiskulturen sowohl im Vorauflauf- als auch im Nachauflauf- Verfahren.
Zur Erhöhung der Kulturpflanzenverträglichkeit kann den herbiziden Mitteln, die die Verbindung der Formel (I) enthalten, ein Safener zugesetzt werden. Folgende Gruppen von Verbindungen sind insbesondere als Safener geeignet:
1) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure, vorzugsweise Verbindungen wie l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl) -5-methyl-2-pyrazolin-3-carbon- säureethylester (S 1-1, Mefenpyr-diethyl, bekannt aus e-Pesticide Manual of the British Crop Protection Council, 2002-2003, 1201 edition, Editor C.D.S. Tomlin = "e-PM"), und verwandte Verbindungen, wie sie in der WO 91/07874 beschrieben sind.
2) Derivate der Dichlorphenylpyrazolcarbonsäure, vorzugsweise Verbindμngen wie l-(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S 1-2), l-(2,4-Dichlor- phenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S 1-3), l-(2,4-Dichlor- phenyl)-5-(l,l-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S 1-4), l-(2,4-Dichlor- phenyl)-5-phenyl-pyrazol-3-carbonsäureethylester (S 1-5) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind.
3) Verbindungen vom Typ der Triazolcarbonsäuren, vorzugsweise Verbindungen wie Fenchlorazol, d.h. l-(2,4-Dichlorphenyl)-5-1xichlo-τnethyl-(lH)-l,2,4-triazol-3-carbon- säureethylester (S 1-6, Fenchlorazol-ethyl, bekannt aus dem e-PM), und verwandte Verbindungen (siehe EP-A-174562 und EP-A-346 620). •
4) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5, 5 -Diphenyl-2-isoxazolin-3 -carbonsäure vorzugsweise Verbindungen wie 5-(2j4-Dichlor- . benzyl)-2-isoxazolin-3-carbonsäureethylester (S 1-7) oder 5-Phenyl-2-isoxazolin-3-carbon- säureethylester (S 1-8) und verwandte Verbindungen, wie sie in WO 91/08202 beschrieben sind, bzw. der 5,5-Diphenyl-2-isoxazolin-carbonsäureethylester (S 1-9, Isoxadifen-ethyl) oder -n-propylester (S 1-10) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbon- säureethylester (S 1-11), wie sie in der Patentanmeldung (WO-A-95/07897) beschrieben sind.
5) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2), vorzugsweise (5-Chlor-8-chinolinoxy)-essigsäure-(l-methyl-hex-l-yl)-ester (S 2-1 Cloquintocet-mexyl, bekannt aus e-PM), (5-Chlor-8-chinolinoxy)-essigsäure-(l,3-dimethyl-but-l-yl)-ester (S2-2), (5-CMor-8-chinolinoxy)-essigsäure-4-allyl-oxy-butylester (S2-3), . (5-CMor-8-c nolinoxy)-essigsäure-l-allyloxy-prop-2-ylester (S2-4), (5-Chlor-8-chinolinoxy)-essigsäureethylester (S2-5), (5-Chlor-8-chinolinoxy)-essigsäuremethylester (S2-6), (5-Chlor-8-chinolinoxy)-essigsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)-essigsäure-2-(2-propyliden-iminoxy)-l- ethylester (S2-8), ' ' • . (5-Chlor-8-chinolinoxy)-essigsäure-2-oxo-prop-l-ylester (S2-9) » und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und EP-A-191 736 5 oder EP-A-0 492 366 beschrieben sind.
6) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)-malonsäure, vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)-malonsäure-diethylester, (5-Chlor-8-chinoli- noxy)-malonsäurediallylester, (5-Chlor-8-chinolinoxy)-malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. '
1.0 7) Wirkstoffe vom Typ der Pyrimidine, wie „Fenclorim" (bekannt aus e-PM of the British Crop Protection Council, 2002-2003, 12tt edition, Editor C.D.S. Tomlin = "e-PM'-') (= 4,6- • Dichlor-2-phenylpyrimidin),
8) Wirkstoffe vom Typ der Dichloracetamide, die häufig als Vorauflaufsafener (bodenwirk- same Safener) angewendet werden, wie z.B.
15 ' „Dichlormid" (e-PM) (= N,N-Diallyl-2,2-dichlbracetamid), „R-29148" (= 3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidon von der Firma Stauffer), „Benoxacor" (e-PM) (= 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin). „PPG-1292" (= N-Allyl-N[(l,3-dioxolan-2-yl)-methyl]dichloracetamid von der Firma PPG 0 Industries), „DK-24" (= N-Allyl-N-[(allylaminocarbonyl)-methyl]-dichloracetamid von der Firma Sagro-Chem), „AD-67" oder „MON 4660" (= 3-Dichloracetyl-l-oxä-3-aza-spiro[4,5]decan von der Firma Nitrokemia bzw. Monsanto), „Dicyclonon" oder „BAS145138" oder „LAB145138" <= (= 3-Dichloracetyl-2,5,5-tri- 5 methyl-l,3-diazabiclyco[4.3.0]nonan von der Firma BASF) und „Furilazol" oder „MON 13900" (e-PM) (= (RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyl- oxazolidon)
9) Wirkstoffe vom Typ der Dichloracetonderivate, wie z.B. ■ „MG 191" (CÄS-Reg. Nr. 96420-72-3) (= 2-DicHormethyl-2-methyl-l,3-.dioxolan von der 0 Firma Nitrokemia),
10) Wirkstoffe vom Typ der Oxyimino-Verbindungen, die als Saatbeizmittel bekannt sind, wie z.B. „Oxabetrinil" (e-PM) (= (Z)-l,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril), das als Saatbeiz-Safener gegen Schäden von Metolachlor bekannt ist, „Fluxofeni " (e-PM) (= l-(4-Chlorphenyl)-2,2,2-trifluor-l-ethanon-0-(l,3-dioxolan-2- ylmethyl)-oxim, das als Saatbeiz-Safener gegen Schäden von Metolachlor bekannt ist, und- „Cyometrinil" oder „CGA-43089" (e-PM) (= (Z)-Cyanomethoxyimino (phenyl)acetonitril), das als Saatbeiz-Safener gegen Schäden von Metolachlor bekannt ist,
11) Wirkstoffe vom Typ der Thiazolcarbonsäureester, die als Saatbeizmittel bekannt sind, wie z.B. „Flurazole" (e-PM) (= 2-Chlor-4-1xifluormethyl-l,3-thiazol-5-carbonsäureben--ylester), das als Saatbeiz-Safener gegen Schäden von Alachlor und Metolachlor bekannt ist,
12) Wirkstoffe vom Typ der Napthalindicarbonsäurederivate, die als Saatbeizmittel bekannt sind, wie z.B. „Naphthalic anhydride" (e-PM) (= 1,8-Naphthalindicarbonsäureanhydrid), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, 13) Wirkstoffe vom Typ Chromanessigsäurederivate, wie z.B. „CL 304415" (CAS-Reg. Nr. 31541-57-8) (= 2-84-Carboxy-chroman-4-yl)-essigsäure von der Firma American Cyanamid),
14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen aufweisen, wie z.B. „Dimepiperate" oder „MY-93" (e-PM) (= Piperidin-l-thiocarbonsäure-S-l-methyl-1- phenylethylester), „Daimuron" oder „SK 23" (e-PM) (= l-(l-Methyl-l-phenylethyl)-3-p-tolyl-harnstoff), „Cumyluron" = „JC-940" (= 3-(2-Chlorphenylmethyl)-l-(l-methyl-l-phenyl- ethyl)-harnstoff, siehe JP-A-60087254), „Methoxyphenon" oder „NK 049" (= 3,3'-Dimethyl-4-methoxy- benzöphenon), „CSB" (= l-Brom-4-(chlormethylsulfonyl)-benzol) (CAS-Reg. Nr. 54091-06-4 von Kumiai), und Verbindungen von Typ der Acylsulfamoylbenzoesäureamide, z.B. der nachfolgenden Formel (H), die z.B. bekannt sind aus WO 99/16744.
Figure imgf000006_0001
Figure imgf000007_0001
Bevorzugte Safener sind Benoxacor, Mefenpyr, Fenchlorazol, Isoxadifen, Cloquintocet und deren Cι-Cιo-Alkylester, insbesondere Benoxacor (S 4-1), Mefenpyr-diethyl (S 1-1), Fenchlorazol-ethyl (S 1-6), Isoxadifen-ethyl (S 1-9), Cloquintocet-mexyl (S 2-1), und (S 3-1). Die nicht in der WO 03/026427 konkret vorbeschriebenen herbiziden Mittel, enthaltend eine Wirk- stoffkombination bestehend aus einer Verbindung der Formel (Ε) und einem der in dieser Anmel- ' düng genannten Safener sind ebenfalls Gegenstand der vorliegenden Anmeldung. Sie eignen sich insbesondere gut zur selektiven Bekämpfung von Unkräutern in Getreide- und Maiskulturen. •
Es ist als überraschend anzusehen, dass aus einer Vielzahl von bekannten Safenern oder Antidots, die befähigt sind, die schädigende Wirkung eines Herbizids auf die Kulturpflanzen zu antagonisieren, gerade einige der oben genannten Safener geeignet sind, die schädigende Wirkung des Wirkstoffs der Formel (I) und dessen Salzen, gegebenenfalls auch in Kombination mit einem oder mehreren der unten angeführten bekannten herbiziden Mischpartner, auf die Kulturpflanzen annähernd vollständig, aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Un- kräutern zu beeinträchtigen.
Als Mischpartner zur kombinierten Anwendung mit der Verbindung der Formel (I) seien die folgenden Verbindungen genannt, die aus dem e-Pesticide Manual of the British Crop Protectioh Council, 2002-2003, 1201 edition, Editor C.D.S. Tomlin, aus der WO 03/026426 oder den angegebenen Literaturstellen bekannt sind: , ' Acetochlor (B.l), Acifluorfen , Acifluorfen-sodium (B.2), Aclonifen (B.3), Alachlor (B.4), Alloxy- dim (B.5), Alloxydim-sodium, (B.6), Ametryn (B.7), Amicarbazone (B.8), Amidosulfuron (B.9), Amitrole (B.10), Anilofos (B.l l), Asulam (B.12) und Asulam-sodium (B.13), Atrazine (B.14), Azafenidin (B.15), Azimsulfuron (B.16), Beflubutamid (B.17), Benazolin (B.18) und Benazolin- ethyl (B.19), Benfluralin (B.20), Benfuresate (B.21), Bensulfuron-methyl (B.22), Bentazone (B.23),. Benfhiocarb (B.24), Benzfendizone (B.25), Benzobicyclon (B.26), Benzofenap (B.274), Bifenox (B.275), Bispyribac-sodium (B.27), Bromacil (B.28), Bromobutide (B.29), Bromofenoxim
. (B.30), Bromoxynil (B.31), Bromoxynyl-heptanoat (B.32), Bromoxynil-octanoat (B.33), Bromoxy- nil-potassium (B.34), Butachlor (B.35), Butafenacü (B.36), Butralin (B.37), Butroxydim (B.38), Butylate (B.39), Gafenstrole (B.40), Carbetamide (B.41), Carfentrazone-ethyl (B.42), Chlometoxyfen (B.43), Chloridazon (B.44), ehlorimuron-ethyl (B.45), Chlornitrofen (B.46), Chlorotoluron (B.47), Chlorsulfuron (B.48), Ginidon-ethyl (B.50), Cinmethylin (B.51), Cino- 5 sulfuron (B.52), Clefoxydim (B.53), Clethodym (B.54), Clodihafop-propargyl (B.55), Clomazone (B.56), Clomeprop (B.57), Clopyralid (B.58), Cloransula -methyl (B.59), Cumyluroή (B.60), Cyanazine (B.61), Cyclosulfamuron (B.62), Cycloxydim (B.63), .Cyhalofop-butyl (B.64), (2,4-D (B.65) und seine Salze (B.66), A ine (B.67) und Ester (B.68), Desmedipham (B.69), Dicamba • (B.70) und seine Salze (B.71), Dicamba-diolamine (B.72), Dichlobenil (B.73), Dichlorprop-P
10 (B.74), Diclofop-methyl (B.75), Diclosulam (B.76), Difenzoquat (B.77), Difenzoquat metilsulfate (B.78), Diflufenican (B.79), Diflufenzopyr (B.80), Dimefuron (B:81), Dimepiperate (B.82), Di- methachlor (B.83), Dimethametryn (B:84), Dimethenamid (B.85), Dimthenamid-P (B.86), Di- mexyflam (B.87), Diquat-dibro ide (B.88), Dithiopyr (B.89), Diuron (B.90), Dymron (B.91), EPTC (B.92), Esprocarb (B.93), Ethalfluralin (B.94), Ethametsulfuron-methyl (B.95), Etho-
15 fumesate (B.96), Ethoxyfen (B.97), Ethoxysulfuron (B.98) und dessen Natriumsalz (B.99), Etho- benzanid (B.100), Fenoxaprop-P-ethyl (B.101), Fentrazamide (B.102), Flamprop-M-methyl (B.l 03) und -M-isopropyl (B.l 04), Flazasulfuron (B.l 05), Florasula (B.106), Fluazofop-P-ethyl (B.107), Fluazifop-P-butyl (B.108), Flucarbazone-sodium (B.109), Fluazolate (B.l 10), Flufenacet (B.l 11), Flufenpyr (B.112), Flumetsulam (B.l 13), Flitmiclorac-pentyl (B.l 14), Flumioxazin
-0 (B.115), Flumipropyn (B.116), Fluometuron (B.117), Fluorochloridone (B.1.18), Fuoroglycofen- ethyl (B.l 19), Flupoxam (B.120), Flupropacil (B.121), Flupyrsulfuron-methyl (B.122) und dessen Natriumsalz (B.123), Flurenol (B.124), Fluroxypyr . (B.125) und seine Ester (B.126) wie Fluroxypyr-meptyl (B.127), Flurtamone (B.128), Fluthiacet-methyl (B.129), Fomesafen (B.130), Foramsulfuron (B.131), Glufosinate (B.132), Glufosinate-ammonium (B.133), L-Glufosinate (L-
15 PTC) (B.277) und dessen Salze (B.278) (vgl. GB 2011416), Bilanafos (L-PTC-L-alaninyl-alanin) (B.279), Glyphosate (B.134), Glyphosate-ammonium (B.135), Glyphosate-isopropylammonium (B.136), Glyphosate-sodium (B.137), Glyphosate-trimesium (B.138), Halosulfuron-methyl (B.139), Haloxyfop (B.140), -methyl (B.141), -P-methyl (B.142), -ethoxyethyl (B.143) oder-butyl (B.144), Hexazinone (B.145), hnazamethabenz-methyl (B.146), Imazamox (B.147), Imazapic
•0 (B.148), hnazapyr (B.149), hnazaquin (B.150), Jmazethpyr (B.151), Imazosul uron (B.152), indanofan (B.153), Iodosulfuron-methyl-sodium (B.154), Ioxynil (B.155), Ioxynil-octanoate (B.156), Ioxyniϊ-sodium (B.157), Isoproturon (B.158), Isouron (B.159), Isoxaben (B.160), Isoxa- chlortole (B.161) ([4-chlor-2-(methylsulfonyl)phenyl](5-cyclopropyl-4-isoxazolyl)-methanon bekannt aus EP 470 856), Isoxaflutole (B.162), Ketospiradox (B.163), Lactofen (B.1'64), Lenacil
5 (B.165), Linuron (B.166), MCPA (B.167), Mecoprop-P (B.168), Mefenacet (B.169), Mesosulfuron-methyl (B.170) und dessen Natriumsalz (B.171), Mesotrione (B.172), Metamitron (B.173), Metazachlor (B.l 74), Methabenzthiazuron (B.175), Metobromuron (B.176), Metolachlor (B.177), S Metolachlor (B.178), Metosula (B.179), Metoxuron (B.180), Metribuzin (B.181), Metsulfiiron '(B.l 82), Metsulfuron-methyl (B.183), Molinate (B. 184), Naproanilide (B.185), Napropamide (B.186), Neburon (B.187), Nicosulfuron (B.188), Norflurazon (B.189), Orbencarb (B.l 90), Oryzalin (B.191), Oxadiargyl (B.192), Oxadiazon (B.193), Oxasulfuron (B.194), Oxaziclo efone (BΛ9S), Oxyfluorfen (B.196), Paraquat (B.197), Pendimethalin (B.198), Pendralin (B.199), Penoxsulam (B.200), Pentoxazone (B.201), Penthoxamid (B.202), Phen- medipham (B.203), Picloram (B.204), Picolinafen (B.205), Pinoxaden (2,2-Dimethyl- 8-(2,6- diethyl-4-methylphenyl)-l ,2,4,5-tetrahydro-7-oxo-7H- pyrazolo[ 1 ,2-d] [ 1 ,4,5] oxadiazepin-9-yl- propanoate; vgl. WO 99/47525) (B.280), Piperophos (B.206), Pretilachlor (B.207), Primisulfuron- methyl (B. 208), Profluazol (B.209), Profόxydi (B.210), Prometryn (B.211), Propachlor (B.212), Propanil (B.49), Propaquizafop (B.213), Propisochlor (B.214), Propoxycarbazone-sodium (B.215), Propyzamide (B.216), Prosulfocarb (B.217), Prosulfuron '(B.218), Pyraclonil (B.219) (l-(3-chlor- 4,5,6i7-tetrahydropyrazolo[l,5-a]pyridin-2-yl)-5-(methyl-2-propinylamino)-lH-pyrazole-4- carbonitril bekannt aus WO 94/08999), Pyraflufen-ethyl (B.220), Pyrazolate (B.221), Pyrazosulfuron-ethyl (B.222), Pyrazoxyfen (B.223), Pyribenzoxym (B.224), Pyributicarb (B.225),
, Pyridafol (B.226), Pyridate (B.227), Pyridatol (B.228), Pyriftalid (B.229), Pyriminobac-methyl (B.230), Pyrithiobac-sodium (B.231), Quinchlorac (B.232), Quinmerac (B.233), Quinoclamine (B.234), Quizalofop (B.235), -ethyl (B.236), -P-ethyl (B.237) und -P-tefuryl (B.238), Rimsulforon, (B.239), Sethoxydim (B.240), Simazine (B.241), Sulcotrione (B.242); Sulfentrazone (B.243), Sulfometuron-methyl (B.244), Sulfosate (B.245), Sulfosulfuron (B.246), Tebuthiuron . (B.247), Tepraloxydim (B.248), Terbuthylazine (B,249), Terbutryn (B.250), Thenylchlor (B.251),
■ Thiazopyr (B.252), Thifensulfuron-methyl (B.253), Thiocarbazil (B.254), Tralkoxydim (B.255), Triallate (B.256), Triasulfuron (B.276), Tribenuron-methyl (B.257), Triclopyr (B.258), Tridiphane (B.259), Trifloxysulfuron (B.260), Trifluralin (B.261), Triflusulfuron-methyl (B.262), Tritosulfuron (B.263) (H-[[[4-memoxy-6-(1-rifluoπnethyl)-l,3,5-triazin-2-yl]amino]carbonyl]- 2- (trifluormethyl)-benzolsulfonamid (B. 264) bekannt aus DE 4038430), N-[[(4,6-Dimethoxy-2-pyri- rmdinyl)-a-nino]-carbonyl]-3-(N-methyl-N-me ylsulfonyl-annno])-2-pyridinsulfonamid (B.265), (vgl. WO-A-92/10660), N-[[(4,6-Dimethoxy-2-pyriιnidinyl)-amino]-carbonyl]-3-(N-methyl-N- methylsulfonyl-amino)-2-pyridinsulfonamid (B.266), (vgl. WO-A-92/10660), 4-(4,5-Dihydro-4- methyl-5-oxo-3 -trifluormethyl- 1H- 1 ,2,4-triazol- 1 -yl)-2-(ethylsulfonylamino)-5 -fluor-benzolcarbo- thioa id (B. 267, HWH4991, vgl. WO-A-95/30661), 2-Chlor-N-[l-(2,6-dichlor-4-difluormethyl- phenyl)-4-nitro-lH-pyrazol-5-yl]-propancarbonsäureamid (B. 268, SLA5599, vgl. EP-A-303153), [2-CUor-3-(4,5-cühydro-3-isoxazolyl)-4-methylsulfonyl-phenyl]-(5-hydrox-l-methyl-lH-pyrazol- 4-yl)-methanon (B.269) (vgl.WO-A-96/26206j WO-A-98/31681), [3-(4,5-Dihydro-3-isoxazolyl)-2- methyl-4-methylsulfonyl-phenyl]-(5-hydrox-l-methyl-lH-pyrazol-4-yl)-methanon (B.270) (vgl.WO-A-96/26206, WO-A-98/31681), [3-[2-Chlor-3[(2,6-dioxo-cyclohexyl)-carbonyl]-6-ethyl- sulfonyl-phenyl]-5-isoxazolyl]-acetonitril. (B.271) (vgl. WO-A-01/28341), 2-[2-Chlor-4-methyl- sulfonyl-3-[(2,2,2-trifluor-ethoxy)-methyl]-benzoyl]-l,3-cyclohexandion (B.272)(vgl. WO-A- 01/28341), 2-[[5,8-Dimethyl-l,l-dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6-yl]- carbonyl]-l,3-cyclohexandion (B.273) (vgl. WO-A-01/28341).
L-Glufosinate (B.277) und Bilanafos (B. 279) haben die folgenden Formeln (L-Phosphinothricin, L-Glufosinate)
Figure imgf000010_0001
Figure imgf000010_0002
(Bilanafos = LPhosphinothπcyl-L-aianyl-L-alanin)
Die Kombinationen mit den Mischpartnern zeichnen sich dadurch aus, dass die Verbindung der Formel (I) -bei gemeinsamer Anwendung mit den bekannten herbizid wirksamen Verbindungen aus - verschiedenen Stoffldassen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und/oder, die Kulturpflanzen- Verträglichkeit signifikant verbessern und besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in Nut-φflanzenkulttiren, wie z.B. in Baumwolle, Gerste, Mais, Kartoffeln, Reis, Soja, Sonnenblumen, Weizen und Zuckerrohr, insbesondere Weizen und Mais, verwendet werden können.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirkstoff- kombinationen aus der Verbindung der Formel (I) und den aufgelisteten Mischpartnern erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungs- ergänzung. Die Wirkstoffkombinationen sind in vielen Kulturen gut verträglich, wobei die Wirk- stoffkombinationen auch sonst schwer bekämpfbare Unkräuter gut bekämpfen. Die neuen Wirkstoffkombinationen stellen somit eine wertvolle Bereicherung der Herbizide dar.
Der synergistische . Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) bevorzugt 0,05 bis 100 Gewichts- teile der Mischpartner. Besonders bevorzugt enthalten die Mischungen auf 1 Gewichtsteil Wirkstoff der Formel (I) 0,1 bis 10 Gewichtsteile der Mischpartner.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, Wenn die herbizide Wirkung der Wirkstoffkombination größer ist als die der einzelnen applizierten Wirkstoffe.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl. COLBY, S.R.: "Caleulating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Seiten 20 - 22, 1967).
Wenn
X = % Schädigung durch Herbizid A (Wirkstoff der Formel I) bei p kg/ha Aufwandmenge
und
Y = % Schädigung durch Herbizid B (Wirkstoff der Formel II) bei q kg/ha Aufwandmenge
und
E = die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge,
dann ist
E = X + Y - (X * Y/100).
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt.
Die Wirkstoffkombinationen enthaltend die Verbindung der Formel (I) und andere bekannte Herbizide und/oder Safener weisen in der Tat die Eigenschaft auf, dass ihre gefundene herbizide Wirkung stärker ist als die berechnete, das heißt, dass die Wirkstoffkombinationen synergistisch wirken.
Als besonders geeignete Mittel seien die folgenden -Zweier-Kombinationen besonders hervorgehoben (Verbindung der Formel (I) = A):
A + (B.l), A + (B.2), A + (B.3), A + (B.4); A + (B.5), A + (B.6), A + (B.7), A + (B.8), A + (B.9), A + (B.10), A + (B.11), A + (B.12), A + (B.13), A + (B.14), A + (B.15), A + (B.16), A + (B.17), A + (B.18), A + (B.19), A + (B.20), A + (B.21), A + (B.22), A + (B.23), A + (B.24), A + (B.25), A + (B.26), A + (B.27), A + (B.28), A + (B.29), A + (B.30), A + (B.31), A + (B.32), A + (B.33), A + (B.34), A + (B-35), A + (B.36), A + (B.37), A + (B.38), A + (B.39), A + (B.40), A + (B.41), A + (B.42), A + (B.43), A + (B.44), A + (B.45), A + (B.46), A + (B.47), A + (B.48), A + (B.49) A 4- (B.50), A + (B.51), A + (B.52), A + (B.53), A + (B.54), A + (B.55), A + (B.56), A + (B.57) A 4- (B.58), A + (B.59), A + (B.60), A + (B.61), A + (B.62), A + (B.63), A + (B.64), A + (B.65) A 4- (B.66), A + (B.67), A + (B.68), A + (B.69), A + (B.70), A + (B.71), A + (B.72), A.+ (B.73) A 4- (B.74), A + (B.75), A + (B.76), A + (B.77), A + (B.78), A + (B.79), A + (B.80), A + (B.81) A 4- (B.82), A + (B.83), A + (B.84), A + (B.85), A + (B.86), A + (B.87), A + (B.88), A + (B.89) A 4- (B.90), A + (BSV), A + (B.92), A + (B.93), A + (B.94), A + (B.95), A + (B.96), A + (B.97) A 4- (B.98), A + (B.99), A + (B.100), A + (B.101), A + (B.102), A 4- (B.103), A + (B.104) A 4- (B.105), A + (B.106), A + (B.107), A + (B.108), A + (B.109), A + (B.l 10), A + (B.l 11) A 4-
(B.l 12) A + (B.113) A + (B.l 14), A + (B.l 15) A + CB.116) A + (B.117) A 4- (B.118) A 4- (B.l 19) A + (B.120) A + (B.121), A 4- (B.122) A-+ (B.123) A + (B.124) A 4- (B.125): A 4- (B.126) A +.(B.127) A + (B.l-28), A + (B.129) A + (B.l 30) A + (B.131) A 4- (B.132) A 4- (B.l 33) A + (B.134) A +,(B.135), A + (B.136) A + (B.137) A 4- (B.138) A 4- (B.l 39) A 4- (B.140) A + (B.141) A + (B.142), A + CB1.43) A + (B-144) A + (B.145) A 4- (B.146) A 4- CB-147) A + (B.148) A + (B.149), A + (B.150) A + (B:151> A 4- (B.152) A 4- (B.153) A 4- (B.154) A + (B.155) A + (B.156), A + (B.157) A + (B.158) A 4- (B.159) A 4- (B.160) A 4- (B.161) A + (B.162) A +. (B.163), A + (B.164) A + (B.165) A 4- (B.166) A - (B.167) A 4- B.168); A + (B.169) A + (B.170), A + (B.171) A + (B.172) A 4- (B.173) A 4- (B.174) A 4- (B.175) A + (B.176) A + (B.177), A + CB.178) A + (B.179) A 4- (B.180) A +' (B.181> A 4- (B.l 82) A + (B.183) A + (B.184), A + (B.185) A + (B.186) A 4- (B.l 87} A 4- (B.188) A 4- (B.189) A + (B.190) A + (B.191), A + (B.192) A + (B.193); A 4- (B.194) A 4- (B.195) A 4- (B.196) A + (B.197) A + (B.198), A + (B.199) A + (B.200) A 4- (B.201) A 4-'(B.202) A 4- (B.203): A + (B.204) A + (B.205), A + (B.206) A + (B.207) A 4- (B.208) A 4- (B.209) A 4- (B.210) A + (B.211) A + (B.212), A + (B-213) A + (B.214) A 4- (B.215) A 4- (B.216) A + (B.217) A + (B.218) A + (B.219), A + (B.220) A + (B.221) A 4- (B.222) A 4- (B.223): A - (B.224) A + (B.225) A + (B.226), A + (B.227) A + (B.228); A 4- (B.229) A 4- (B.230) A 4- (B.231) A + (B.232) A + (B.233), A + (B.234) A + (B.235) A 4- (B.236) A 4- (B.237) A 4- (B.238) A + (B.239) A + (B.240), A + (B.241) A + (B.242) A 4- (B.243) A 4- (B.244) A 4- (B.245); A + (B.246); A + (B.247), A + (B.248): A + (B.249) A 4- (B.250) A 4- (B.251) A - (B.252) A + (B.253); A + (B.254), A + (B.255) A + (B.256) A 4- (B.257); A 4- (B.258) A 4- (B.259) A + (B.260) A + (B.261), A + (B.262) A 4- (B.263) A 4- (B.264) A 4- (B.265) A - (B.266) A + (B.267), A 4- (B.268), A + (B.269), A 4- (B.270), A 4- (B.271), A 4- (B.272) und A + (B.273) A + (B'.274) A 4- (B.275), A 4- (B.276), A 4- (B.277), A 4- (B.278), A4-(B.279), A 4- (B.280).
Als besonders geeignete Mittel seien die folgenden Kombinationen mit Safener (S 4-1) besonders hervorgehoben (Verbindung der Formel (I) = A): A 4- (S 4-1), A 4- (B.l) 4- (S 4-1), A 4- (B.2) 4- (S 4-1), A 4- (B.3) 4- (S 4-1), A 4- (B.4) 4- (S 4-1), A + (B.5) 4- (S 4-1), A + (B.6) 4- (S 4-1), A 4- (B.7) + (S 4-1), A 4- (B.8) 4- (S 4-1), A 4- (B.9) 4- (S 4-1), .' A 4- (B.10) +'(S 4-1), A 4- (B.l 1) 4- (S 4-1), A 4- (B.12) 4- (S 4-1), A 4- (B.l 3) 4- (S 4-1), A 4- (B.14) 4- (S 4-1), A 4- (B.15) 4- (S 4-1), A 4- (B.16) 4- (S 4-1), A 4- (B.17) 4- (S 4-1), A + (B.18) 4- (S 4-1), A 4- (B.19) 4- (S 4-1), A 4- (B.20) +'(S 4-1), A 4- (B.21) +.(S 4-1), A 4- (B.22) 4- (S 4-1), A 4- (B.23) + (S 4-1), A 4- (B.24) 4- (S 4-1), A 4- (B.25) 4- (S 4-1), A 4- (B.26) 4- (S 4-1), A 4- (B.27) 4- (S 4-1), A + (B.28) 4- (S 4-1), A 4- (B.29) 4- (S 4-1), A + (B.30) 4- (S 4-1), A 4- (B.31) 4- (S 4-1), A 4- (B.32) 4- (S • 4-1), A 4- (B.33) 4- (S 4-1), A 4- (B.34) 4- (S 4-i A 4- (B.35) 4- (S 4-1), A 4- (B.36) + (S 4-1), A + (B.37) 4- (S 4-1), A 4- (B.38) 4- (S 4-1), A 4- (B.39) 4- (S 4-1), A 4- (B.40) 4- (S 4-1), A 4- (B.41) 4- (S 4-1), A 4- (B.42) 4- (S 4-1), A 4- (B.43) 4- (S 4-1), A 4- (B.44) 4- (S 4-1), A 4- (B.45) 4- (S 4-1), A + (B.46) 4- (S 4-1), A 4- (B.47) 4- (S 4-1), A 4- (B.48) 4- (S 4-1), A + (B.49) 4- (S 4-1), A 4- (B.50) 4- (S .4-1), A 4- (B.51) 4- (S 4-1), A 4- (B.52) 4- (S 4-1), A 4- (B.53) 4- (S 4-1), A 4- (B.54) 4- (S 4-1), A + (B.55) 4- (S 4-1), A 4- (B.56) 4- (S 4-1), A 4- (B.57) 4- (S 4-1), A 4- (B.58) 4- (S 4-1), A 4- (B.59) 4- (S 4-1), A 4- (B.60) 4- (S 4-1), A 4- (B.61) 4- (S 4^1), A 4- (B.62) 4- (S 4-1), A 4- (B.63) 4- (S 4-1), A 4- (B.64) 4- (S 4-1), A 4- (B.65) + (S 4-1), A 4- (B.66) 4- (S 4-1), A 4- (B.67) 4- (S 4-1), A 4- (B.68) 4- (S 4-1), A 4- (B.69) 4- (S 4-1), A 4- (B.70) 4- (S 4-1), A 4- (B.71) 4- (S 4-1), A 4- (B.72) 4- (S 4-1), A + (B.73) 4- (S 4-1), A + (B.74) 4- (S 4-1), A 4- (B.75) 4- (S 4-1), A 4- (B.76) 4- (S 4-1), A 4- (B.77) 4- (S 4-1), A 4- (B 8) 4- (S 4-1), A 4- (B.79) 4- (S 4-1), A +. (B.80) 4- (S 4-1), A 4- (B.81) 4- (S 4-1), A 4- (B.82) 4- (S 4-1), A 4- (B.83) 4- (S 4-1), A 4- (B.84) 4- (S 4-1), A 4- (B.85) 4- (S 4-1),- A 4- (B.86) 4- (S 4-1), A 4- (B.87) 4- (S 4-1), A 4- (B.88) 4- (S 4-1), A 4- (B.89) 4- (S 4-1), A 4- (B.90) 4- (S 4-1), A + (B.91) 4- (S 4-1), A 4- (B.92) 4- (S 4-1), A 4- (B.93) 4- (S 471), A 4- (B.94) 4- (S 4-1), A 4- (B.95) 4- (S 4-1), A 4- (B.96) 4- (S 4-1), A 4-'(B.97) 4- (S 4-1), A + (B.98) 4- (S 4-1), A 4- (B.99) 4- (S 4-1), A + (B.100) 4- (S 4-1 A 4- (B.101) 4- (S 4-1) , A 4- (B.102) 4- (S 4-1 . A 4- (B.103) + (S 4-1), (B.104) 4- (S 4-1 A 4- (B.105) 4- (S 4-1) , A 4- (B.106) 4- (S 4-1 ), A + (B.107) + (S 4-1), (B.108) 4- (S 4-1 A 4- (B.109) 4- (S 4-1) A 4- (B.llO) 4- (S 4-1 ). A 4- (B.ll l) 4- (S 4-1), (B.l 12) 4- (S 4-1 A + (B.l 13) + -(S 4-1) A 4- (B.l 14) 4- (S 4-1 ), A + (B.115) 4- (S 4-1), (B.l 16) 4- (S -1 A 4- (B.l 17) 4- (S 4-1) A + (B.118) 4- (S 4-1 ), A + (B.119) 4- (S 4-1), (B.120) + (S 4-1 A 4- (B.121) 4- (S 4-1) A 4- (B.122) 4- (S 4-1 ), A + (B.123) + (S 4-1), (B.124) 4- (S 4-1 A 4- (B.125) 4- (S 4-1) A 4- (B.126) 4- (S 4-1 ), A + (B.127) 4- (S 4-1), (B.128) 4- (S 4-1 A 4- (B.129) 4- (S 4-1) A 4- (B.l 30) 4- (S 4-1 ). A 4- (B.131) + (S 4-1), (B.132) 4- (S 4-1 A 4- (B.133) 4- (S 4-1) A 4- (B.134) + (S 4-1 ), A + (B.135) 4- (S 4-1), (B.136) 4- (S 4-1 A 4- (B.137) 4- (S 4-1) A 4- (B.138) 4- (S 4-1 ). A 4- (B.139) 4- (S 4-1), (B.140) 4- (S 4-1 A 4- (B.141) 4- (S 4-1) A 4- (B.142) 4- (S 4-1 A 4- (B1.43) + (S 4-1), (B.144) 4-' (S 4-1 A 4- (B.145) 4- (S 4-1), A 4- (B.146) 4- (S 4-1 ), A + (B.147) + (S 4-1), (B.148) 4- (S 4-1 A 4- (B.149) 4- (S 4-1), A 4- (B.l 50) + (S 4-1 ), A + (B.151) + (S 4-1), (B.152) 4- (S 4-1 A + (B.153) 4- (S 4-1), A 4- (B.154) 4- (S 4-1. ), A + (B.155) 4- (S 4-1), (B.156) 4- (S 4-: A +' (B.157) 4- (S 4-1 A 4- (B.158) 4- (S 4- , A 4- (B.159) 4- (S 4-1), A 4- (B.160) 4- (S 4-: A 4- (B.161) 4- (S 4-1 A 4- (B.162) 4- (S 4- , A 4- (B.163) 4- (S 4-1), A + (B.164) 4- (S 4-: A 4- (B.165) 4- (S 4-1 A 4- (B.166) + (S 4- , A 4- (B.167) 4- (S 4-1), A + (B.l 68) + (S 4-: A 4- (B.169) + (S 4-1 A 4- (B..170) 4- (S 4- , A 4- (B.171) 4- (S 4-1), A + (B.172) 4- (S 4-: A 4- (B.173) 4- (S 4-1 A 4- (B.174) 4- (S 4- , A 4- (B.175) 4- (S 4-1), A + (B.176) + (S 4-: A 4- (B.177) 4- (S 4-1 A 4- (B.178) 4- (S 4- , A 4- (B.179) 4- (S 4-1), A + (B.180) + (S 4-] A 4- (B.181) 4- (S 4-1 A 4- (B.182) 4- (S 4- , A 4- (B.183) 4- (S 4-1), A 4- (B.l 84) 4- (S 4-] A 4- (B.l 85) 4- (S 4-f A 4- (B.186) 4- (S 4- , A 4- (B.l 87) 4- (S 4-1), A + (B.188) 4- (S 4-1 A 4- (B.189) 4- (S 4-1 A 4- (B.190) 4- (S 4-: , A 4- (B.191) + (S 4-1), A 4- (B.192) 4- (S.4-1 A 4- (B.l 93) 4- (S 4-1 A 4- (B.194) 4- (S 4-: , A 4- (B.195) 4- (S 4-1), A 4- (B.196) 4- (S 4-] A 4- (B.197) 4- (S 4-1 A 4- (B.198) 4- (S 4-: , A 4- (B.199) 4- (S 4-1), A + (B.200) 4- (S 4-] A 4- (B.201) 4- (S 4-1 A 4- (B.202) 4- (S 4-: , A 4- (B.203) 4- (S 4-1), A + (B.204) 4- (S 4-1 A 4- (B.205) 4- (S 4-1 A 4- (B.206) 4- (S 4-: , A 4- (B.207) 4- (S 4-1), A 4- (B.208) + (S 4-1 A ■+ (B.209) 4- (S 4-1 A 4- (B.210) 4- (S 4-: , A + (B.211) + (S 4-1), A 4- (B.212) + (S 4-1 A 4- (B.213) 4- (S 4-1 A 4- (B.214) 4- (S 4-: , A 4- (B.215) 4- (S 4-1), A + (B.216) 4- (S 4-1 A 4- (B.217) 4- (S 4-1 A 4- (B.218) 4- (S 4-; , A 4- (B.219) 4- (S 4-1), A + (B.220) 4- (S 4-1 A 4- (B.221) 4- (S 4-1 A 4- (B.222) 4- (S 4-: , A 4- (B.223) 4- (S 4-1), A + (B.224) 4- (S 4-1 A 4- (B.225) 4- (S 4-1 A 4- (B.226) 4- (S 4-: , A 4- (B.227) 4- (S 4-1), A + (B.228) 4- (S 4-1 A 4- (B.229) 4- (S 4-1 A 4- (B.230) 4- (S 4-] , A 4- (B.231) + (S 4-1), A 4- (B.232) 4- (S 4-1 A + .(B.233) + (S 4-f A 4- (B.234) 4- (S 4-] , A 4- (B.235) 4- (S 4-1), A + (B.236) 4- (S 4-1 A 4- (B.237) 4- (S 4-1 A 4- (B.238) 4- (S 4-] , A 4- (B.239) 4- (S 4-1),. A 4- (B.240) 4- (S 4-1 A 4- (B.241) 4- (S 4-1 A 4- (B.242) + (S 4-1 , A 4- (B.243) 4- (S 4-1), A + (B.244) 4- (S 4-1 A 4- (B.245) 4- (S 4-1 A + .(B.246) 4- (S 4-1 , A 4- (B.247) 4- (S 4-1), A 4- (B.248) 4- (S 4-1 A 4- (B.249) 4- (S 4-1 A + (B.250) 4- (S 4-] , A 4- (B.251) 4- (S 4-1), A + (B.252) 4- (S 4-1 A 4- (B.253) 4- (S 4-1 A 4- (B.254) + (S 4- , A 4- (B.255) .+ (S 4-1), A + (B.256) 4- (S 4-1 A 4- (B.257) 4- (S 4-1 A 4- ß.258) 4- (S 4- ), A 4- (B.259) 4- (S 4-1), A 4- (B.260) 4- (S 4-1 A 4- (B.261) 4- (S 4-1 A 4- (B.262) 4- (S 4- ), A 4- (B.263) 4- (S 4-1), A + (B.264) 4- (S 4-1 A 4- (B.265) 4- (S 4-1 A 4- (B.266) 4-' (S 4- ), A 4- (B.267) 4- (S 4-1), A + (B.268) 4- (S 4-1 A 4- (B.269) 4- (S 4-1 A 4-' (B.270) 4- (S 4- ), A 4- (B.271) 4- (S 4-1), A 4- (B.272) 4- (S 4- A 4- (B.273) 4- (S 4-1 A 4- (B.274) 4- (S 4- ), A 4- (B.275) 4- (S 4-1), A + (B.276) 4- (S 4-1 A 4- (B.277) 4- (S 4-1), A 4- (B.278) 4- (S 4-1), A4-(B.279) 4- (S 4-1), A + (B 280) 4- (S 4-1).
Als besonders geeignete Mittel seien die folgenden Zweier-Kombinationen mit Safener (S 1-1) besonders hervorgehoben (Verbindung der Formel (I) = A): A + (S 1-1), A 4- (B.l) 4- (S 1-1), A 4- (B.2) 4- (S 1-1), A 4- (B.3) 4- (S 1-1), A 4- (B.4) 4- (S 1-1), A + (B.5) 4- (S 1-1), A 4- (B.6) 4- (S 1-1), A 4- (B.7) 4-' (S 1-1), A 4- (B.8) + (S 1-1), A 4- (B.9) +'(S 1-1), A 4- (B.10) +'(S 1-1), A 4- (B.l l) 4- (S 1-1), A 4- (B.12) 4- (S 1-1), A 4- (B.l 3) 4- (S 1-1), A 4- (B.14) + (S 1-1), A + (B.15) 4- (S 1-1), A 4- (B.l 6) 4- (S 1-1), A 4- (B.17) 4- (S 1-1), A + (B.18) +'(S 1-1), A 4- (B.19) 4- (S 1-1), A 4- (B.20) 4- (S 1-1), A 4- (B.21) 4- (S-l-1), A 4- (B.22) 4- (S 1-1), A + (B.23) + (S 1-1), A 4- (B.24) 4- (S 1-1), A 4- (B.25) 4- (S 1-1), A 4- (B.26) 4- (S 1-1), A 4- (B.27) 4- (S 1-1), A + (B.28) 4- (S 1-1), A 4- (B.29) + (S 1-1), A 4- (B 0) 4- (S 1-1), A 4- (B.31) 4- (S 1-1), A 4- (B.32) 4- (S 1-1), A 4- (B.33) 4- (S 1-1), A 4- (B.34) 4- (S 1-1), A 4- (B.35) 4- (S 1-1), A 4- (B.36) 4- (S 1-1), A + (B.37) 4- (S 1-1), A 4- (B.38) 4- (S 1-1), A 4- (B.39) 4- (S 1-1), A 4- (B.40) 4- (S 1-1), A 4- (B.41) 4- (S 1-1), A 4- (B.42) 4- (S 1-1), A 4- (B.43) 4- (S 1-1), A 4- (B.44) 4- (S 1-1), A 4- (B.45) 4- (S 1-1), A 4- (B.46) 4- (S 1-1), A 4- (B.47) 4- (S 1-1), A 4- (B.48) 4- (S 1-1), A + (B.49) 4- (S 1-1), A 4- (B.50) 4- (S 1-1), A 4- (B.51) + (S 1-1),'A 4- (B.52) 4- (S 1-1), A 4- (B.53) 4- (S 1-1), A 4- (B.54) 4- (S 1-1), A + (B.55) 4- (S 1-1), A 4- (B.56) + (S 1-1), A + (B.57) 4- (S 1-1), A 4- (B.58) 4- (S 1-1), A 4- (B.59) 4- (S ' 1-1), A 4- (B.60) 4- (S 1-1), A 4- (B.61) 4- (S 1-1), A + (B.62) 4- (S 1-1), A 4- (B.63) 4- (S 1-1), A 4- (B.64) 4- (S 1-1), A 4- (B.65) 4- (S 1-1), A 4- (B.66) 4- (S 1-1), A 4- (B.67) 4- (S 1-1), A 4- (B.68) 4- (S 1-1), A 4- (B.69) 4- (S 1-1), A 4- (B.70) 4- (S 1-1), A 4- (B.71) 4- (S 1-1), A 4- (B.72) 4- (S 1-1), A + (B.73) 4- (S 1-1), A 4- (B.74) 4- (S 1-1), A 4- (B.75) 4- (S 1-1), A 4- (B.76) + (S 1-1), A 4- (B.77) 4- (S 1-I), A +-(B.78) + (S 1-1), A 4- (B.79) 4- (S 1-1), A + (B.80) + (S 1-1), A 4- (B.81) 4- (S 1-1), A 4- (B.82) 4- (S 1-1), A 4- (B.83) 4- (S 1-1), A 4-' (B.84) 4- (S 1-1), A 4- (B.85) 4- (S 1-1), A 4- (B.86) 4- (S • 1-1), A 4- (B.87) 4- (S 1-1), A 4- (B.88) 4- (S 1-1), A 4- (B.89) + (S 1-1), A 4- (B.90) 4- (S 1-1), A + (B.91) 4- (S 1-1), A 4- (B.92) 4- (S 1-1), A 4- (B.93) 4- (S 1-1), A 4- (B.94) 4- (S 1-1), A 4- (B.95) 4- (S 1-1), A 4- (B.96) 4- (S 1-1), A 4- (B.97) 4- (S 1-1), A 4- (B.98) 4- (S 1-1), A 4- (B.99) 4- (S 1-1), A 4-
(B.100) 4- (S 1-1) , A 4- (B.101) + (S -1), A 4- (B.102) 4- (S 1-1), A 4- (B.103 + (s 1-1)):, A +
(B.104) 4- (S 1-1) , A 4- (B.105) 4- (S -1), A 4- (B.106) 4- (S 1-1), A 4- (B.107 + (s 1-1)):, A 4-
(B.108) 4- (S 1-1) , A + (B.109) 4- (S -1), A + (B.l lO) 4- (S 1-1), A + (B.1Ϊ1 -) + (S 1-1)), A +
(B.l 12) 4- (S i-i) , A 4- (B.l 13) 4- (S -1), A 4- (B.l 14) 4- (S 1-1), A + (B.115 »;) + (S 1-1 )):, A +
<B.116) 4- (S i-i) , A 4- (B.l 17) 4- (S -1), A 4- (B.118) 4- (S 1-1), A 4- (B.l 19 );) + (S 1-1)), A +
(B.120) 4- (S 1-1) , A 4- (B.121) 4- (S -1), A 4- (B.122) 4- (S 1-1), A.4- (B.123 + (s 1-1 U) +
(B.124) 4- (S i-i) , A 4- (B.125) 4- (S -1), A 4- (B.126) 4- (s' 1-1), A 4- (B.127; + (s ι-i));, A +
(B.128) 4- (S i-i) , A 4- (B.129) 4- (S -1), A + (B.130) 4- (S 1-1), A + (B.13i; ) + (S 1-1): +
(B.132) 4- (S 1-1): , A 4- (B.133) 4- (S -1), A + (B.134) + (S 1-1), A 4- (B.135 ;) + (s 1-1)):, A +
(B.136) 4- (S 1-1): , A 4- (B.137) 4- (S -1), A 4- (B.138) 4- (S 1-1), A 4- (B.139 ») + (s 1-D ):, A +
(B.140) 4- (S 1-1): , A 4- (B.141) 4- (S -1), A 4- (B.142) 4- (S 1-1), A 4- (B1.43 i) + (S 1-1)):, A +
(B.144) 4- (S 1-1): , A 4- (B.145) + (S -1), A + (B.146) 4- (S 1-1), A 4- (B.147 ') + (s 1-1)):, A +
(B.148) 4- (S 1-D: , A 4- (B.149) 4- (S -1), A 4- (B.150) 4- (S 1-1), A 4- (B.151 .) + (S 1-1)):, A +
(B.152) 4- (S 1-1): , A - '(B.153) 4- (S -l), A 4- (B.l 54) 4- (S 1-1), A 4- (B.155 ;) + (s 1-1)):, A + (B.156) 4- (S 1-1) A 4- (B.157) + l), A 4- (B.158) 4- (S A 4- (B.159) 4- (S 1-1), A + (B.160) 4- (S 1-1) ),, A 4- (B.161) 4- l), A 4- (B.162) 4- (S A 4- (B.163) 4- (S 1-1), A + (B.164) + (S 1-1) ),, A 4- (B.165) 4- L), A - (B.166) 4- (S A 4- (B.167) 4- (S 1-1), A + (B.168) +- (S 1-1) ),, A + (B.169) 4- 1), A 4- (B.170) 4- (S A 4- (B.171) 4- (S 1-1), A 4- (B.172) 4- (S 1-1) ),, A 4- (B.173) 4- 1), A 4- (B.174) + (S A 4- (B.175) 4- (S 1-1), A + (B.176) 4- (S 1-1) ),, A +" (B.177) 4- l), A 4- (B.178) + (S A 4- (B.179) 4- (S 1-1), A + (B.180) 4- (S 1-1) );i A 4- (B.181) + l), A 4- (B.182) 4- (S A 4- (B.183) 4- (S 1-1), A + (B.184) 4- (S 1-1) ),, A 4- (B.185) 4- l), A 4- (B.l 86) 4- (S A 4- (B.187) 4- (S 1-1), A + (B.188) 4- (S 1-1) ),, A 4- (B.189) + 1), A 4- (B.190) 4- (S A 4- (B.1'91) 4- (S 1-1), A 4- (B.192) 4- (S 1-1) ),, A 4- (B.193) 4- l), A 4- (B.194) 4- (S A 4- (B.195) 4- (S 1-1), A + (B.196) 4- (S 1-1) ),, A 4- (B.197) 4- l), A 4- (B.l-98) 4- (S A 4- (B.199) 4- (S 1-1), A + (B.200) 4- (S 1-1) ),, A 4- (B.201) + 1), A 4- (B.202) 4- (S A 4- (B.203) 4- (S 1-1), A + (B.204) 4- (S 1-1) ),, A 4- (B.205) 4- 1), A 4- (B.20'6) 4- (S A + (B.207) 4- (S 1-1), A + (B.208) 4- (S 1-1) ),, A 4- (B.209) 4- 1), A 4- (B.210) 4- (S A + (B.211) 4- (S 1-1), A 4- (B.212) 4- (S 1-1) ),, A 4- (B.213) 4- 1), A 4- (B.214) + (S A 4- (B.215) + (S 1-1), A 4- .(B.216)' + (S 1-1) ),, A 4- (B.217) 4- 1), A + (B.218) 4- (S A + (B.219) 4- (S 1-1), A 4- (B.220) 4- (S 1-1) ),, A 4- (B.221) 4- 1), A 4- (B.222) 4- (S A 4- (B.223) 4- (S 1-1), A + (B.224) 4- (S 1-1) ),, A 4- (B.225) 4- 1), A 4- (B.226) 4- (S A 4- (B.227) 4- (S 1-1), A 4- (B.228) 4- (S 1-1) ),, A 4- (B.229) 4- 1), A 4- (B.230) 4- (S A + (B.231) + (S 1-1), A 4- (B.232) 4- (S 1-1) ),, A 4- (B.233) 4- 1), A 4- (B.234) 4- (S A 4- (B.235) 4- (S 1-1), A 4-
• (B.236)' 4- (S 1-1) ),, A 4- (B.237) 4- 1), A 4- (B.238) 4- (S A 4- (B.239) 4- (S 1-1), A + (B.240) 4- (S 1-1) ),, A + (B.241) 4- 1), A 4- (B.242) + (S A 4-'(B.243) 4- (S. 1-1), A 4- (B.244) 4- (S 1-1) ),, A 4- (B.245) 4- l), A 4- (B.246) 4- (S A 4- (B.247) 4- (S 1-1), A + (B.248) 4- (S 1-1) ),, A 4- (B.249) 4- 1), A 4- (B.250) 4- (S A 4- (B.251) 4- (S 1-1), A + (B.252) 4- (S 1-1), A 4- (B.253) 4- 1), A + (B.254) 4- (S A 4- (B.255) 4- (S 1-1), A + (B.256) 4- (S 1-1) ),, A + (B.257) 4- 1), A 4- (B.258) 4- (S A 4- (B.259) 4- (S 1-1), A + (B.260) 4- (S 1-1) ),, A 4- (B.261) + 1), A 4- (B.262) 4- (S A 4- (B.263) + (S 1-1), A + (B.264) 4- (S 1-1) ),, A 4- (B.265) 4- 1), A 4- (B.266) 4- (S A 4- (B.267) 4- (S 1-1), A + (B.268) 4- (S 1-1) ),, A 4- (B.269) 4- 1), A 4- (B.270) 4- (S A + (B.271) + (S 1-1), A 4- . (B.272) 4- (S 1-1) ),, A 4- (B.273) + 1), A 4-, (B.274) 4- (S ), A 4- (B.275) 4- (S 1-1), A + (B.276) 4- (S 1-1), A + (B.277) 4- (S . + (B.278) + (S 1-1), A 4-(B.279) 4- (S 1-1), A 4- (B.280) + (S 1-1).
Als besonders geeignete Mittel seien die folgenden Zweier-Kombinationen mit Safener (S 1-6)- besonders hervorgehoben (Verbindung der Formel (T) = A): A 4- (S 1-6), A 4- (B.l) + (S 1-6), A 4- (B.2) 4- (S 1-6), A + (B.3) 4- (S 1-6), A 4- (B.4) 4- (S 1-6), A + (B.5) 4- (S 1-6), A 4- (B.6) 4- (S 1-6), A 4- (B.7) 4- (S 1-6), A 4- (B.8) 4- (S 1-6), A 4- (B.9) 4- (S 1-6), A 4- (B.10) 4- (S 1-6), A 4- (B.ll) + (S 1-6), A 4- (B.12) + (S 1-6), A 4- (B.13) + (S 1-6), A 4- (B.14) ■ 4- (S 1-6), A 4- (B.15) 4- (S 1-6), A 4- (B.16) 4- (S 1-6), A 4- (B.ll) + (S 1-6), A 4- (B.18) 4- (S 1-6), A . 4- (B.19) 4- (S 1-6), A 4- (B.20) 4- (S 1-6), A 4- (B.21) 4- (S 1-6), A 4- (B.22) 4- (S 1-6), A 4- (B.23) + (S 1-6), A 4- (B.24) 4- (S 1-6), A + (B.25) + (S 1-6), A 4- (B.26) + (S 1-6), A + (B.27) 4- (S 1-6), A + (B.28) 4- (S 1-6), A 4- (B.29) + (S 1-6), A 4- (B.30) + (S 1-6), A + (B.31) 4- (S 1-6), A 4- (B.32) 4- (S 1-6), A 4- (B.33) 4- (S 1-6), A 4- (B.34) 4- (S-l-6), A + (B.35) 4- (S 1-6), A 4- (B.36) 4- (S 1-6), A + (B.37) + (S 1-6), A 4- (B.38) + (S 1-6), A + (B.39) 4- (S .1-6), A 4- (B.40) 4- (S 1-6), A 4- (B.41) 4- (S 1-6), A + (B.42) + (S 1-6), A + (B.43) + (S 1-6), A 4- (B.44) 4- (S 1-6), A 4- (B.45) 4- (S 1-6), A + . (B.46) + (S 1-6), A 4- (B.47) 4- (S 1-6), A 4- (B.48) 4- (S 1-6), A + (B.49) 4- (S 1-6), A + (B.50) + (S 1-6), A + (B.51) 4- (S 1-6), A 4- (B.52) 4- (S 1-6), A 4- (B.53) 4- (S 1-6), A 4- (B.54) 4- (S 1-6), A + (B.55) + (S 1-6), A 4- (B.56) 4- (S 1-6), A 4- (B.57) 4- (S 1-6), A 4- (B.58) 4- (S 1-6), A 4- (B.59) 4- (S 1-6), A .4- (B.60) 4- (S 1-6), A 4- (B.61) 4- (S 1-6), A 4- (B.62) 4- (S 1-6), A 4- (B.63) 4- (S 1-6), A + (B.64) + (S 1-6), A + (B.65) 4- (S 1-6), A 4- (B.66) 4- (S 1-6), A 4- (B.67) 4- (S 1-6), A + (B.68) 4- (S 1-6), A 4- (B.69) + (S 1-6), A + (B.70) 4- (S 1-6), A 4- (B.71) + (S 1-6), A + (B.72) + (S 1-6), A + (B.73) + (S 1-6), A 4- (B.74) 4- (S 1-6), A 4- (B.75) 4- (S 1-6), A 4- (B.76) 4- (S 1-6), A 4- (B.77) 4- (S
■ 1-6), A + (B.78) + (S 1-6), A + (B.79) + (S 1-6), A 4- (B.80) + (S 1-6), A 4- (B.81) 4- (S 1-6), A + (B.82) + (S 1-6), A 4- (B.83) 4- (S 1-6), A + (B.84) 4- (S 1-6), A 4- (B.85) 4- (S 1-6), A + (B.86) 4- (S 1-6), A + (B.87) 4- (S 1-6), A + (B.88) 4- (S 1-6), A 4- (B.89) + (S 1-6), A 4- (B.90) 4- (S 1-6), A + (B.91) 4- (S 1-6), A 4- (B.92) 4- (S 1-6), A +. (B.93) + (S 1-6), A + (B.94) 4- (S 1-6), A 4- (B.95) 4- (S 1-6), A 4- (B.96) 4- (S 1-6), A 4- (B.97) 4- (S 1-6), A 4- (B.98) + (S 1-6), A 4- (B.99) 4- (S 1-6), A + (B.100) 4- (S 1-6), A 4- (B.101) 4- (S 1-6), A 4- (B.102) + (S 1-6), A 4- (B.103) 4- (S 1-6), A + (B.104) 4- (S 1-6), A 4- (B.105) +' (S 1-6), A + (B.106) 4- (S 1-6), A 4- (B.107) 4- (S 1-6), A + (B.108) 4- (S 1-6), A 4- (B.109) + (S 1-6), A 4- (B.l lO) 4- (S 1-6), A 4- (B.l 11) 4- (S 1-6), A + (B.112) + (S 1-6), A 4- (B.Ϊ 13) 4- (S 1-6), A 4- (B.l 14) 4- (S 1-6), A 4- (B.115) 4- (S 1-6), A + (B.l 16) 4- (S 1-6), A 4- (B.l 17) 4- (S 1-6), A 4- (B.l 18) 4- (S 1-6), A 4- (B.l 19) 4- (S 1-6), A + (B.120) 4- (S 1-6), A 4- (B.121) 4- (S 1-6), A 4- (B.122) 4- (S 1-6), A 4- (B.123) 4- (S 1-6), A .+ (B.124) + (S 1-6), A + (B.125) 4- (S 1-6), A 4- (B.126) 4- (S 1-6), A 4- (B.127) 4- (S 1-6), A + (B.128) 4- (S 1-6), A + (B.129) 4- (S 1-6), A 4- (B.130) 4- (S 1-6), A 4- (B.131) 4- (S 1-6), A + (B.132) 4- (S 1-6), A 4- (B.133) 4- (S' 1-6), A 4- (B.134) 4- (S 1-6), A 4- (B.135) 4- (S 1-6), A + (B.136) 4- (S 1-6), A + (B.137) + (S 1-6), A 4- (B.138) 4- (S 1-6), A 4- (B.139) 4- (S 1-6), A 4- (B.140) 4- (S 1-6), A 4- (B.141) 4- (S 1-6), A + (B.142) 4- (S 1-6), A 4- (B1.43) + (S 1-6), A + (B.144) + (S 1-6), A 4- (B.145) 4- (S 1-6), A + (B.146) 4- (S 1-6), A 4- (B.147.) 4- (S 1-6), A + (B.148) 4- (S 1-6), A 4- (B.149) 4- (S 1-6), A + (B.150) 4- (S 1-6), A 4- (B.151) 4- (S 1-6), A + (B.152) 4- (S 1-6), A + (B.153) + (S 1-6), A 4- (B.154) 4- (S 1-6), A 4- (B.155) 4- (S 1-6), A 4- (B.156) + (S 1-6) A 4- (B.157) + (S l-6): , A 4- (B.158) 4- (S 1-6), A + (B.159) 4- (S 1-6), A + (B.160) + (S 1-6) A 4- (B.161) + (S l-6); , A 4- (B.162) + (S 1-6), A 4- (B.163) 4- (S 1-6), A + (B.164) 4- (S 1-6) A 4- (B.165) 4- (S 1-6) , A 4- (B.166) 4- (S 1-6), A 4- (B.167) 4- (S 1-6), A + (B.l 68) 4- (S 1-6) A 4- (B.169) + (S 1-6) , A 4- (B.170) + (S 1-6), A + (B.171) 4- (S 1-6), A + (B.172) 4- (S 1-6) A + (B.173) + (S 1-6) ,. A 4- (B.174) 4- (S 1-6), A 4- (B.175) + (S 1-6), A + (B.176) .+' (S 1-6) A + (B.177) 4- (S 1-6) , A + (B.178) + (S 1-6), A 4- (B.179) + (S 1-6), A + (B.180) 4- (S 1-6) A 4- (B.181) 4- (S 1-6) , A + (B.182) 4- (S 1-6), A 4- (B.183) 4- (S 1-6), A 4- (B.l 84) 4- (S 1-6) A + (B.Ϊ85) 4- (S 1-6) , A 4- (B.186) + (S 1-6), A 4- (B.187) + (S 1-6), A + ' (B.188) + (S 1-6) A 4- (B.189) 4- (S 1-6} , A 4- (B.190) 4- (S 1-6), A 4- (B.191) 4- (S 1-6), A + • (B.192) + (S 1-6) A + (B.193) 4- (S 1-6) , A 4- (B.194) 4- (S 1-6), A 4- (B.195) + (S 1-6), A + (B.196) + (S 1-6) A 4- (B.197) 4- (S 1-6) , A 4- (B.198) 4- (S 1-6), A + (B.199) 4- (S 1-6), A + (B.200) + (S 1-6) A 4- (B.201) + (S 1-6) , A 4- (B.202) 4- (S 1-6), A 4- (B.203) 4- (S 1-6), A + (B.204) 4- (S 1-6) A 4- (B.205) 4- (S 1-6) , A 4- (B.206) 4- (S 1-6), A 4- (B.207) 4- (S 1-6), A + (B.208) 4- (S 1-6) A 4- (B.209) 4- (S 1-6) , A 4- (B.210) + (S 1-6), A 4- (B.211) + (S 1-6), A + (B.212) 4- (S 1-6) A 4- (B.213) 4- (S 1-6) , A 4- (B.214) + (S 1-6), A 4- (B.215) 4- (S 1-6), A + (B.216) + (S 1-6) A 4- (B.217) 4- (S- l-6) , A 4- (B.218) 4- (S 1-6), A 4- (B.219) 4- (S 1-6), A + (B.220) 4- (S 1-6) A 4- (B.221) 4- (S 1-6) , A 4- (B.222) "+ (S 1-6), A 4- (B.223) + (S 1-6), A + (B.224) 4- (S 1-6) A 4- (B.225) 4- (S 1-6) , A 4- (B.226) 4- (S 1-6), A 4- (B.227) 4- (S 1-6), A + (B.228) 4- (S 1-6) A 4- (B.229) 4- (S 1-6) , A + (B.230) 4- (S 1-6), A 4- (B.231) 4- (S 1-6), A 4- (B.232) + (S 1-6) A 4- (B.233) + (S 1-6) , A 4- (B.234) 4- (S 1-6), A 4- (B.235) 4- (S 1-6), A 4- (B.236) 4- (S 1-6) A 4- (B.237) 4- (S 1-6) , A 4- (B.238) 4- (S 1-6), A 4- (B.239) 4- (S 1-6), A + (B.240) 4- (S 1-6) A 4- (B.241) + (S 1-6) , A 4- (B.242) 4- (S 1-6), A 4- (B.243) 4- (S 1-6), A 4- (B.244) + (S 1-6) A 4- (B.245) 4- (S 1-6) , A 4- (B.246) 4- (S 1-6), A 4- (B.247) 4- (S 1-6), A + (B.248) 4- (S 1-6) A 4- (B.249) 4- (S 1-6) , A 4- (B.250) 4- (S 1-6), A 4- (B.251) 4- (S 1-6), A + (B.252) 4- (S 1-6) A 4- (B.253) 4- (S 1-6), , A 4- (B.254) + (S 1-6), A 4- (B.255) 4- (S 1-6), A 4- (B.256) 4- (S 1-6) A 4- (B.257) 4- (S 1-6) , A 4- (B.258) 4- (S 1-6), A 4- (B.259) 4- (S 1-6), A 4- (B.260) + (S 1-6) A 4- (B.261) 4- (S 1-6) , A 4- (B.262) 4- (S 1-6), A 4- (B.263) 4- (S 1-6), A + (B.264) 4- (S 1-6) A 4- (B.265) 4- (S 1-6) , A + (B.266) + (S 1-6), A 4- (B.267) 4- (S 1-6), A 4- . (B.268) 4- (S 1-6) A 4- (B.269) + (S 1-6), A 4- (B.270) + (S 1-6), A 4- (B.271) 4- (S 1-6), A + (B.272) + (S l-6): A 4- (B.273) + (S 1-6), A 4- (B.274) 4- (S 1-6), A 4- (B.275) 4- (S 1-6), A + (B.276) + (S 1-6), A 4- (B.277) + (S 1-6), A + (B.278) + (S 1- 6), A +(B.279) + (S 1-6), A 4- (B.280) 4- (S 1-6).
Als besonders geeignete Mittel seien die folgenden Zweier-Kombinationen mit Safener (S 1-9) besonders hervorgehoben (Verbindung der Formel (I) = A): A 4- (S 1-9), A 4- (B.l) + (S 1-9), A 4- (B.2) 4- (S 1-9), A + (B.3) 4- (S 1-9), A 4- (B.4) 4- (S 1-9), A + * (B.5) 4- (S 1-9), A + (B.6) 4- (S 1-9), A 4- (B.7) 4- (S 1-9), A 4- (B.8) 4- (S 1-9), A 4- (B.9) 4- (S 1-9), A 4- (B.10) 4- (S 1-9), A 4- (B.l l) 4- (S 1-9), A 4- (B.12) 4- (S 1-9), A 4- (B.l 3) 4- (S 1-9), A 4- (B.14) 4- (S 1-9), A 4- (B.15) 4- (S 1-9), A + (B.16) 4- (S 1-9), A + (B.17) 4- (S 1-9),' A + (B.18) 4- (S 1-9), A 4- (B.19) 4- (S 1-9), A 4- (B.20) 4- (S 1-9), A + (B.21) 4- (S 1-9), A 4- (B.22) 4- (S 1-9), A 4- (B.23) + • (S 1-9), A 4- (B.24) 4- (S 1-9), A 4- (B.25) 4- (S 1-9), A 4- (B.26) 4- (S 1-9), A 4- (B.27) 4- (S 1-9), A + (B.28) 4- (S 1-9), A 4- (B.29) 4- (S 1-9), A 4- (B. -30) 4- (S 1-9), A 4- (B.31) 4- (S 1-9), A 4- (B.32) + (S 1-9), A 4- (B.33) 4- (S 1-9), A + (B.34) 4- (S 1-9), A + (B.35) 4- (S 1-9), A + (B.36) 4- (S 1-9), A 4- (B.37) 4- (S 1-9), A 4- (B.38) 4- (S 1-9), A 4- (B.39) 4- (S 1-9), A 4- (B.40) 4- (S 1-9), A 4- (BAI) + (S 1-9), A 4- (B.42) 4- (S 1-9), A + (B.43) 4- (S 1-9), A 4- (B.44) 4- (S 1-9), A +'(B.45) + (S 1-9), A + (B.46) 4- (S 1-9), A 4- (ß.47) + (S 1-9), A '+ (B.48) 4- (S 1-9), A + (B.49) + (S 1-9), A 4- (B.50) 4- (S 1-9), A 4- (B.51) 4- (S 1-9), A + (B.52) 4- (S 1-9), A 4- (B.53) 4- (S 1-9), A 4- (B.54) 4- (S 1-9), A +
■ (B.55) 4- (S 1-9), A + (B.56) 4- (S 1-9), A 4- (B.57) 4- (S 1-9), A 4- (B.58) 4- (S 1-9), A 4- (B.59) 4- (S 1-9), A 4- (B.60) + (S 1-9), A 4- (B.61) 4- (S 1-9), A 4- (B:62) 4- (S 1-9), A + (B.63) 4- (S 1-9), A 4- (B.64) 4- (S 1-9), A 4- (B.65) 4- (S 1-9), A4- (B.66) 4- (S 1-9), A 4- (B.67) 4- (S 1-9), A+ (B.68)'+ (S 1-9), A 4- (B.69) + (S 1-9), A 4- (B.70) 4- (S 1-9), A 4- (B.71) 4- (S 1-9), A 4- (B.72) + (S 1-9), A + (B.73) 4- (S 1-9), A 4- (B.74).+ (S 1-9), A 4- (B.75) 4- (S 1-9), A + (B.76) + (S 1-9), A + (B.77) 4- (S 1-9), A 4- (B.78) 4- (S 1-9), A + (B.79) 4- (S 1-9), A + (B.80) 4- (S 1-9), A 4- (B.81) + (S 1-9), A +
• (B.82) 4- (S 1-9), A 4- (B.83) 4- (S 1-9), A + (B.84) 4- (S 1-9), A 4- (B.85) 4- (S 1-9), A 4- (B.86) 4- (S 1-9), A 4- (B.87) + (S 1-9), A 4- (B.88) 4- (S 1-9), A 4- (B.89) + (S 1-9), A 4- (B.90) + (S 1-9), A + (B.91) 4- (S 1-9), A 4- (B.92) 4- (S 1-9), A 4- (B.93) 4- (S 1-9), A 4- (B.94) 4- (S 1-9), A 4- (B.95) 4- (S 1-9), A 4- (B.96) 4- (S 1-9), A 4- (B.97) 4- (S 1-9), A 4- (B.98) 4- (S 1-9), A 4- (B.99) 4- (S 1-9), A + (B.100) 4- (S 1-9), A 4- (B.101) + (S 1-9), A 4- (B.102) 4- (S 1-9), A 4- (B.103) 4- (S 1-9), A 4-. (B.104) 4- (S 1-9), A 4- (B.105) + (S 1-9), A 4- (B.106) 4- (S 1-9), A 4- (B.107) 4- (S 1-9), A + (B.108) 4- (S 1-9), A + (B.109) 4- (S 1-9), A 4- (B.llO) + (S 1-9), A 4- (B.ll l) 4- (S 1-9), A + (B.l 12) 4- (S 1-9),- A 4- (B.l 13) + (S 1-9), A + (B.l 14) 4- (S 1-9), A 4- (B.l 15) 4- (S 1-9), A + (B.116) 4- (S 1-9), A + (B.l 17) + (S 1-9), A 4- (B.l 18) + (S 1-9), A 4- (B.119) 4- (S 1-9), A + (B.120) 4- (S 1-9), A 4- (B.121) 4- (S 1-9), A + (B.122) + (S 1-9), A 4- (B.123) 4- (S 1-9), A + (B.124) 4- (S 1-9), A + (B.125) 4- (S 1-9), A 4- (B.126) 4- (S 1-9), A 4- (B.127) 4- (S 1-9), A 4- (B.128) 4- (S 1-9), A 4- (B.129) 4- ('S 1-9), A + (B.130) 4- (S 1-9), A + (B.131) + (S 1-9), A 4- (B.132) 4- (S 1-9), A + (B.133) + (S 1-9), A 4- (B.134) 4- (S 1-9), A 4- (B.135) 4- (S 1-9), A 4- (B.136) 4- (S 1-9), A 4- (B.137) 4- (S 1-9), A 4- (B.138). + (S 1-9), A 4- (B.139) 4- (S 1-9), A + (B.140) 4- (S 1-9), A 4- (B.141) 4- (S 1-9), A 4- (B.142) 4- (S 1-9), A 4- (B1.43) 4- (S 1-9), A + (B.144) 4- (S 1-9), A 4- (B.145) 4- (S 1-9), A + (B.146) 4- (S 1-9), A + (B.147) 4- (S 1-9), A + (B.148) 4- (S 1-9), A 4- (B.149) 4- (S 1-9), A 4- (B.150) 4- (S 1-9), A 4- (B.151) 4- (S 1-9), A 4- (B.152) 4- (S 1-9), A + (B.153) 4- (S 1-9), A 4- (B.154) 4- (S 1-9), A 4-'(B.155) 4- (S 1-9), A 4- (B.156) 4- (S 1-9) , A 4- (B.157) 4- (S . A 4- (B.158) 4- (S 1-9), A + (B.159) 4- (S 1-9), A + (B.160) 4- (S l-9): , A 4- (B.161) 4- (S A 4- (B.162) 4- (S 1-9), A 4- ζB.163) + (S 1-9), A + (B.164) 4- (S 1-9) , A 4- (B.165) 4- (S A 4- (B.166) 4- (S 1-9), A 4- (B.167) 4- (S 1-9), A 4- (B.168) 4- (S 1-9) , A 4- (B.169) 4- (S A 4- (B.170) 4- (S 1-9), A 4- (B.171) 4- (S 1-9), A + (B.172) 4- (S 1-9) , A 4- (B.173) 4- (S A 4- (B.174) 4- (S 1-9), A 4- (B.175) 4- (S 1-9), A + (B.176) 4- (S 1-9) , A 4- (B.177) 4- (S A 4- (B.178) 4- (S 1-9), A 4- (B.179) 4- (S 1-9), A + (B.180) 4- (S 1-9) , A 4- (B.181) + (S A 4- (B.182) 4- (S 1-9), A 4- (B.183) 4- (S 1-9), A + (B.184) 4- (S 1-9) , A 4- (B.185) 4- (S A 4- (B.186) 4- (S 1-9), A 4- (B.i87) 4- (S 1-9), A 4- (B.188) 4- (S l-9) , A 4- (B.189) 4- (S A 4- (B.190) 4- (S 1-9), A 4- (B.191) 4- (S 1-9), A + (B.192) 4- (S 1-9) , A 4- (B.193) 4- (S A 4- (B.194) 4- (S 1-9), A 4- (B.195) + (S 1-9), A + (B.196) 4- (S 1-9) , A 4- (B.197) 4- (S A 4- (B.198) 4- (S 1-9), A 4- (B.199) 4- (S 1-9), A + (B.200) 4- (S 1-9) , A 4- (B.201) 4- (S A 4- (B.202) 4- (S 1-9), A 4- (B.203) 4- (S 1-9), A + (B.204) + (S 1-9) , A 4- (B.205) 4- (S A 4- (B.206) 4- (S 1-9), A 4- (B.207) 4- (S 1-9), A + (B.208) 4- (S 1-9) , A 4- (B.209) 4- (S A 4- (B.210) 4- (S 1-9), A 4- (B.211) 4- (S 1-9), A + (B.212) 4- (S 1-9) , A 4- (B.213) 4- (S A 4- (B.214) 4- (S 1-9), A 4- (B.215) 4- (S 1-9), A + (B.216) 4- (S 1-9) , A 4- (B.217) 4- (S A 4- (B.218) 4- (S 1-9), A 4- (B.219). + (S 1-9), A + (B.220) 4- (S 1-9) , A 4- (B.221) 4- (S A 4- (B.222) 4-- (S 1-9), A 4- (B.223) 4- (S 1-9), A + (B.224) 4- (S 1-9) , A 4- (B.225) 4- (S A 4- (B.226) 4- (S 1-9), A 4- (B.227) 4- (S l-9), A + (B.228) 4- (S 1-9) , A 4- (B.229) 4- (S A 4- (B.230) 4- (S 1-9), A 4- (B.231) 4- (S 1-9), A + (B.232) + (S 1-9) , A 4- (B.233) 4- (S A 4- (B.234) 4- (S 1-9), A + (B.235) 4- (S 1-9), A + (B.236) 4- (S 1-9) , A 4- (B.237) 4- (S A + (B.238) 4- (S 1-9), A 4- (B.239) 4- (S 1-9), A + (B.240) 4- (S 1-9) ', A 4- (B.241) 4- (S A 4- (B.242) 4- (S 1-9), A 4- (B.243) 4- (S 1-9), A + (B.244) 4- (S l-9) , A 4- (B.245) 4- (S A 4- (B.246) 4- (S 1-9), A 4- (B.247) 4- (S 1-9), A + (B.248) 4- (S 1-9) , A 4- (B.249) 4- (S A 4- (B.250) + (S 1-9), A 4- (B.251) 4- (S 1-9),- A + (B.252) 4- (S 1-9) , A 4- (B.253) 4- (S A 4- (B.254) 4- (S 1-9), A 4- (B.255) 4- (S 1-9), A + (B.256) 4- (S 1-9) , A 4- (B.257) 4- (S A 4- (B.258) 4- (S 1-9), A 4- (B.259) 4- (S 1-9), A + (B.260) 4- (S 1-9) , A 4- (B.261) 4- (S A 4- (B.262) 4- (S 1-9), A 4- (B.263) 4- (S 1-9), A + (B.264) 4- (S 1-9) ,-A + (B.265) 4- (S A 4- (B.266) 4- (S 1-9), A 4- (B.267) 4- (S 1-9), A + (B.268) 4- (S 1-9) , A 4- (B.269) 4- (S A 4- (B.270) 4- (S 1-9), A 4- (B.271) 4- (S 1-9), A + (B.272) 4- (S 1-9) , A 4- (B.273) 4- (S , A 4- (B.274) 4- (S 1-9), A -4= (B.275) 4- (S 1-9), A + (B.276) 4- (S 1-9), A 4- (B.277) 4- (S 1-9), A 4- (B.278) 4- (S 1-9), A 4- (B.279) 4- (S 1-9), A + (B.280) 4- (S 1-9).
Als besonders geeignete Mittel seien die folgenden Zweier-Kombinationen mit Safener (S 2-1) besonders hervorgehob ai.. Verbindung der Formel (I) = A): A 4- (S 2-1), A 4- (B.l) 4- (S 2-1), A 4- (B.2) 4- (S 2-1), A 4- (B.3) 4- (S 2-1), A 4- (B.4) 4- (S 2-1), A + (B.5) 4- (S 2-1), A 4- (B.6) 4- (S 2-1), A 4- (B.7) 4- (S 2-1), A + (B.8) 4- (S 2-1), A 4- (B.9) 4- (S 2-1), A 4- (B.10) +'(S 2-1), A 4- (B.l 1) 4- (S 2-1), A 4- (B.12) 4- (S 2-1), A 4- (B.13) 4- (S 2-1), A 4- (B.14) •4- (S 2-1), A 4- (B.15) 4- (S 2-1), A 4- (B.16) 4- (S 2-1), A 4- (B.17) 4- (S 2-1), A 4- (B.l 8) 4- (S 2-1), A 4- (B.19) 4- (S 2-1), A + (B.20) 4- (S 2-1), A 4- (B.21) 4- (S 2-1), A 4- (B.22) 4- (S 2-1), A 4- (B.23) + (S 2-1), A 4- (B.24) 4- (S 2-1), A 4- (B.25) 4- (S 2-1), A 4- (B.26) 4- (S 2-1), A 4- (B.27) 4- (S 2-1), A 4- (B.28) 4- (S 2-1), A 4- (B.29) 4- (S 2-1), A + (B.30) + (S 2-1), A + (B.31) + (S 2-1), A 4- (B.32) 4- (S 2-1), A 4- (B.33) 4- (S 2-1), A 4- (B.34) 4- (S 2:1), A 4- (B.35) 4- (S 2-1), A 4- (B.36) 4- (S 2-1), A + (B.37) 4- (S 2-1), A 4- (B.38) 4- (S 2-1), A 4- (B.39) 4- (S 2-1), A 4- (B.40) 4- (S 2-1), A 4- (B.41) 4- (S 2-1), A 4- (B.42) 4- (S 2-1), A 4- (B.43) 4- (S 2-1), A 4- (B.44) 4- (S 2-1), A 4- (B.45) + (S 2-1), A + (B.46) 4- (S 2-1), A 4- (B.47) 4- (S 2-1), A 4- (BAS) + (S 2-1), A 4- (B.49) 4- (S 2-1), A 4- (B.50) 4- (S 2-1), A 4- (B.51) 4- (S 2-1), A 4- (B.52) 4- (S 2-1), A 4- (B.53) 4- (S 2-1), A 4- (B.54) 4- (S 2-1), A + (B.55) 4- (S 2-1), A 4- (B.56) 4- (S 2-1), A 4- (B.57) 4- (S 2-1), A 4- (B.58) 4- (S 2-1), A 4- (B.59) 4- (S 2-1), A 4- (B.60) 4- (S 2-l)i A 4- (B.61) 4- (S 2-1), A 4- (B.62) 4- (S 2-1), A 4- (B.63) 4- (S 2-1), A + (B.64) 4- (S 2-1), A 4- (B.65) 4- (S 2-1), A 4- (B.66) 4- (S 2-1), A 4- (B.67) 4- (S 2-1), A 4- (B.68) 4- (S
2-1), A 4- (B.69) 4- (S 2-1), A 4- (B.70) 4- (S 2-1), A 4- (B.71) 4- (S 2-1), A 4- (B.72) 4- (S 2-1), A 4-
(B.73) 4- (S'2-l), A 4- (B.74) 4- (S 2-1), A 4- (B.75) 4- (S 24), A 4- (B.76) 4- (S 2-1), A 4- (B.77) 4- (S 2-1), A 4- (B.78) 4- (S 2-1), A 4- (B.79) 4- (S 2-1), A 4- (B.80) 4- (S 2-1), A 4- (B.81) 4- (S 2-1), A +
(B.82) 4- (S 2-1), A 4- (B.83) 4- (S 2-1), A 4- (B.84) 4- (S 2-1), A 4- (B.85) 4- (S 2-1), A 4- (B.86) 4- (S 2-1), A 4- (B.87) 4- (S 2-1), A 4- (B.88) 4- (S 2-1), A + (B.89) 4- (S 2-1), A 4- (B.90) 4- (S 2-1), A + (B.91) 4- (S 2-1), A 4- (B.92) 4- (S 2-1), A 4- (ß.93) + (S 2-1), A 4- (B.94) 4- (S 2-1), A 4- (B.95) 4- (S 2-1), A 4- (B.96) 4- (S 2-1), A 4- (B.97) 4- (S 2-1), A + (B.98) 4- (S 2-1), A 4- (B.99) 4- (S 2-1), A 4- (B.100) 4- (S 2-1), A 4- (B.101) 4- (S 2-1), A 4- (B.102) 4- (S 2-1), A 4- (B.103) 4- (S 2-1), A + (B.104) 4- (S 2-1), A 4- (B.105) 4- (S 2-1), A 4- (B.106) 4- (S 2-1), A 4- (B.107) 4- (S 2-1), A + (B.108) 4- (S 2-1), A 4- (B.109) 4- (S 2-1), A 4- (B.l lO) 4- (S 2-1), A 4- (B.lll) 4- (S 2-1), A + (B.112) 4- (S 2-1), A 4- (B.113) + (S 2-1), A 4- (B.l 14) + (S 2-1), A 4- (B.115) 4- (S 2-1), A + (B.116) 4- (S 2-1), A 4- (B.117) 4- (S 2-1), A 4- (B.118) 4- (S 2-1), A 4- (B.119) 4- (S 2-1), A + (B.120) 4- (S 2-1), A 4-' (B.121) 4- (S 2-1), A 4- (B.122) 4- (S 2-1), A 4- (B.123) 4- (S 2-1), A 4- (B.124) + (S 2-1), A 4- (B.125) 4- (S 2-1), A 4- (B.126) 4- (S 2-1), A 4- (B.127) 4- (S 2-1), A + (B.128) 4- (S 2-1), A 4- (B.129) 4- (S 2rl), A 4- (B.130) 4- (S 2-1), A 4- (B.131) 4- (S 2-1), A + (B.132) 4- (S 2-1), A 4- (B.133) 4- (S 2-1), A 4- (B.134) 4- (S 2-1), A 4- (B.135) + (S 2-1), A + (B.136) 4- (S 2-1), A 4- (B.137) 4- (S 2-1), A 4- (B.138) 4- (S 2-1), A 4- (B.139) 4- (S 2-1), A + (B.140) 4- (S 2-1), A 4- (B.141) 4- (S 2-1), A 4- (B.142) 4- (S 2-1), A + (B1.43) 4- (S 2-1), A + (B.144) + (S 2-1), A 4- (B.145) 4- (S 2-1), A 4- (B.146) 4- (S 2-1), A + (B.147) 4- (S 2-1), A + (B.148) 4- (S 2-1), A 4- (B.149) 4- (S 2-1), A 4- (B.150) 4- (S 2-1), A 4- (B.151) 4- (S 2-1), A + (B.152) 4- (S 2-1), A 4- (B.153) 4- (S 2-1), A 4- (B.154) 4- (S 2-1), A 4- (B.155) 4- (S 2-1), A 4- (B.l 56) + (S 2-1), A 4- (B.157) 4- A 4- (B.158) 4- (S 2 -i),, A 4- (B.159) + (S 2-
(B.160) 4- (S 2-1), A 4- (B.161) 4- A 4- (B.162) 4- (S 2 -i),, A 4- (B.163) 4- (S 2-
(B.164) 4- (S 2-1), A 4- (B.165) 4- A + (B.166) 4- (S 2 -i),, A 4- (B.167) 4- (S 2-
(B.168) 4- (S 2-1), A 4- (B.169) 4- A 4- (B.170) 4- (S 2 -i),, A 4- (B.171) 4- (S 2-
(B.172) 4- (S 2-1), A 4- (B.173) 4- A 4- (B.174) 4- (S 2 -i),, A 4- (B.175) 4- (S 2-
(B.176) 4- (S 2-1), A 4- (B.177) + A 4- (B.178) 4- (S 2 -i),, A 4- (B.179) 4- (S 2-
(B.180) 4- (S 2-1), A 4- (B.181) 4- A 4- (B.182) 4- (S 2 -i)., A 4- (B.l 83) 4- (S 2-
(B.184) 4- (S 2-1), A 4- (B.185) 4- A 4- (B.186) 4- (S 2 -i),, A + (B.187) 4- (S 2-:
(B.18'8) 4- (S 2-1), A 4- (B.189) 4- A 4- (B.190) 4- (S 2 -i),, A 4- (B.191) 4- (S 2-:
(B.192) 4- (S 2-1), A 4- (B.193) 4- A 4- (B.194) 4- (S 2 -i),, A + (B.195) 4- (S 2-:
(B.196) 4- (S 2-1), A + (B.197) 4- A 4- (B.198) 4- (S 2 -i),, A + (B.199) + (S 2-:
(B.200) 4- (S 2-1), A 4- (B.201) 4- A 4- (B.202) 4- (S 2 -i),, A 4- (B.203) 4- (S 2-:
(B.204) 4- (S 2-1), A 4- (B.205) •+ A 4- (B.206) 4- (S 2 -i),, A 4- (B.207) 4- (S 2-:
(B.208) 4- (S 2-1), A 4- (B.209) 4- A 4- (B.210) 4- (S 2 -i),, A 4- (B.211) 4- (S 2-:
(B.212) 4- (S 2-1), A + (B.213) 4- A 4- (B.214) 4- (S 2 -i),, A 4- (B.215) 4- (S 2-:
(B.216) 4- (S 2-1), A 4- (B.217) + A 4- (B.218) 4- (S 2 •i),, A 4- (B.219) 4- (S 2-:
(B.220) 4- (S 2-1), A 4- (B.221) + A + (B.222) 4- (S 2 -i),, A 4- (B.223) 4- (S 2-:
(B.224) 4- (S 2-1), A 4- (B.225) 4- A + (B.226) 4- (S 2 -i),, A 4- (B.227) 4- (S 2-1
(B.228) 4- (S 2-1), A 4- (B.229) 4- A 4- (B.230) + (S 2 ■1),, A-+ (B.231) 4- (S 2-1
(B.232) 4- (S 2-1), A 4- (B.233) + A 4- (B.234) 4- (S 2 -i),, A 4- (B.235) 4- (S 2-1
(13.236) 4- (S 2-1), A 4- (B.237) 4- A 4- (B.238) + (S 2- -i , A 4- (B.239) 4- (S 2-1
(B.240) 4- (S 2-1), Ä 4- (B.241) 4- A 4- (B.242) 4- (S 2- -i)3, A 4- (B.243) 4- (S 2-1
(B.244) 4- (S 2-1), A 4- (B.245) 4- A 4- (B.246) 4- (S 2- -i),, A 4- (B.247) 4- (S 2-1
(B.248) 4- (S 2-1), A 4- (B.249) 4- A 4- (B.250) 4- (S 2- ■1),, A 4- (B.251) 4- (S 2-1
(B.252) 4- (S 2-1), A 4- (B.253) 4- A 4- (B.254) 4- (S 2- 1),, A 4- (B.255) 4- (S 2-
(B.256) + (S 2-1), A 4- (B.257) 4- A + (B.258) 4- (S 2- 1),, A 4- (B.259) 4- (S 2-
(B.260) 4- (S 2-1), A 4- (B.261) 4- A 4- (B.262) + (S 2- 1),, A 4- (B.263) 4- (S 2-
(B.264) 4- (S 2-1), A 4- (B.265) 4- A 4- (B.266) 4- (S 2-1),, A 4- (B.267) 4- (S 2-
(B.268) 4- (S 2-1), A 4- (B.269) 4- A 4- (B.270) + (S 2-1),, A 4- (B.271) 4- (S 2-
(B.272) 4- (S 2-1), A 4- (B.273) 4- A 4- (B.274) 4- (S 2- 1),, A 4- (B.275) 4- (S 2-
(B.276) 4- (S 2-1), A 4- (B.277) 4-
Figure imgf000022_0001
A 4- (B.278) 4- (S 2-1),, A 4- (B.279) 4- (S 2-l);
(B.280) 4- (S 2-1).
Als besonders geeignete Mittel seien die folgenden Zweier-Kombinationen mit Safener (S 3-1) besonders hervorgehoben (Verbindung der Formel (I) — A): A 4- (S 3-1), A 4- (B.l) 4- (S 3-1), A 4- (B.2) 4- (S 3-1), A 4- (B.3) 4- (S 3-1), A + (B.4) + (S 3-1), A + (B.5) 4- (S 3-1), A 4- (B.6) 4- (S 3-1), A 4- (B.l) + (S 3-1), A 4- (B.8) 4- (S 3-1), A 4- (B.9) 4- (S 3-1), A 4- (B.10) +'(S 3-1), A 4- (B.ll) + (S 3-1), A + (B.12) 4- (S 3-1), A 4- (B.l 3) 4- (S 3-1), A + (B.14) 4- (S 3-1), A 4- (B.15) 4- (S 3-1), A 4- (B.16) 4- (S 3-1), A 4- (B.17) 4- (S 3-1), A 4- (B.18) 4- (S 3-1), A 4- (B.19) 4- (S 3-1), A 4- (B.20) 4- (S 3-1), A 4- (B.21) 4- (S 3-1), A 4- (B.22) 4- (S 3-1), A 4- (B.23) + (S 3-1), A 4- (B.24) 4- (S 3-1), A 4- (B.25) 4- (S 3-1), A 4- (B.26) 4- (S 3-1), A 4- (B.27) 4- (S 3-1), A + (B.28) 4- (S 3-1), A 4- (B.29) 4- (S 3-1), A 4- (B.30) 4- (S 3-1), A 4- (B.31) 4- (S 3-1), A 4- (B.32) + (S 3-1), A + (B.33) 4- (S 3-1), A 4- (B.34) 4- (S 3-1), A 4- (B.35) 4- (S 3-1), A 4- (B.36) 4- (S 3-1), A 4- (B.37) 4- (S 3-1), A 4- (B.38) 4- (S 3-1), A 4- (B.39) 4- (S 3-1), A 4- (B.40) 4- (S 3-1), A 4- (BAI) 4- (S 3-1), A 4- (B.42) +-(S 3-1), A 4- (B.43) 4- (S 3-1), A 4- (B.44) 4- (S 3-1), A 4- (B.45) 4- (S 3-1), A 4- (B.46) + (S 3-1), A 4- (BAT) + (S 3-1), A 4- (BAS) + (S 3-1), A 4- (B.49) 4- (S 3-1), A 4- (B.50) 4- (S 3-1), A 4- (B.51) 4- (S 3-1), A 4- (B.52) 4- (S 3-1), A + (B.53) 4- (S 3-1), A 4- (B.54) 4- (S 3-1), A + (B.55) 4- (S 3-1), A 4- (B.56) 4- (S 3-1), A 4- (B.57) 4- (S 3-1), A 4- (B.58) 4- (S 3-1), A 4- (B.59) 4- (S 3-1), A 4- (B.60) 4- (S 3-1), A 4- (B.61) 4- (S 3-1), A 4- (B.62) 4- (S 3-1), A 4- (B.63) 4- (S 3-1), A + (B.64) 4- (S 3-1), A 4- (B.65) 4- (S 3-1), A 4- (B.66) 4- (S 3-1), A 4- (B.67) 4- (S 3-1), A 4- (B.68) 4- (S 3-1), A 4- (B.69) 4- (S 3-1), A 4- (B.70) 4- (S 3-1), A 4- (B.ll) + (S 3-1), A 4- (B.72) 4- (S 3-1), A + (B.73) 4- (S 3-1), A 4- (B.74) 4- (S 3-1), A 4- (B.75) 4- (S 3-1), A 4- (B.76) 4- (S 3-1), A 4- (B.ll) + (S 3-1), A 4- (B.78) 4- (S 3-1), A 4- (B.79) 4- (S 3-1), A 4- (B.80) + (S 3-1), A 4- (B.81) 4- (S 3-1), A + (B.82) 4- (S 3-1), A 4- (B.83) 4- (S 3-1), A 4- (B..84) 4- (S 3-1), A 4- (B.85) 4- (S 3-1), A 4- (B.86) 4- (S 3-1), A 4- (B.87) + (S 3-1),. A 4- (B.88) 4- (S 3-1), A 4- (B.89) 4- (S 3-1), A 4- (B.90) 4- (S 3-1), A + (B.91) 4- (S 3-1), A 4- (B.92) 4- (S 3-1), A 4- (B.93) 4- (S 3-1), A 4- (B.94) 4- (S 3-1), A 4- (B.95) 4- (S 3-1), A 4- (B.96) 4- (S 3-1), A 4- (B.97) 4- (S 3-1), A 4- (B.98) 4- (S 3-1), A 4- (B.99) 4- (S 3-1), A +
(B.100) 4- ((S 3-1), A 4- (B.101) 4- (S 3-1), A 4- (B.102) 4- (S 3-1), A 4- (B.103) 4- (S 3-1), A 4-
(B.104) 4- ((S 3-1), A 4- (B.105) 4- (S 3-1), A 4- (B.106) 4- (S 3-1), A 4- (B.107) 4- (S 3-1), A + ( (BB..110088)) 44-- ((S 3-1), A 4- (B.109) 4- (S 3-1), A 4- (B.l lO) 4- (S 3-1), A 4- (B.l l l) 4- (S 3-1), A +
(B.l 12) 4- ((S 3-1), A 4- (B.113) 4- (S 3-1), A 4- (B.114) 4- (S 3-1), A 4- (B.115) 4- (S 3-1), A +
(B.l 16) + ( (S 3-1), A + B.117) 4- (S 3-1), A + (B.l 18) 4- (S 3-1), A 4- (B.l 19) 4- (S 3-1), A 4-
(B.120) 4- ((S 3-1), A 4- (B.121) 4- (S 3-1), A 4- (B.122) 4- (S 3-1), A 4- (B.123) 4- (S 3-1), A +
(B.124) 4- ((S 3-1), A 4- (B.125) 4- (S 3-1), A 4- (B.126) 4- (S 3-1), A 4- (B.127) + (S 3-1), A + ( (BB..112288)) 44-- ((S 3-1), A 4- (B.129) 4- (S 3-1), A 4- (B.130) 4- (S 3-1), A 4- (B.131) 4- (S 3-1), A +
(B.132) 4- ((S> 3-1), A 4- (B.133) 4- (S 3-1), A 4- (B.134) + (S 3-1), A 4- (B.135) 4- (S 3-1), A +
(B.136) 4- (S 3-1), A 4- (B.137) 4- (S 3-1), A 4- (B.138) 4- (S 3-1), A 4- (B.139) 4- (S 3-1), A +
(B.140) 4- ( (S 3-1), A 4- (B.141) 4- (S 3-1), A 4- (B.142) + S 3-1), A 4- (B1.43) 4- (S 3-1), A +
(B.144) 4- ((Sϊ 3-1), A 4- (B.145) 4- (S 3-1), A 4- (B.146) 4- (S 3-1), A 4- (B.147) + (S 3-1), A + ( (BB..114488)) 44-- ((S! 3-1), A 4- (B.149) 4- (S 3-1), A 4- (B.150) + (S 3-1), A 4- (B.151) 4- (S 3-1), A 4-
(B.152) + ((S< 3-1), A 4- (B.153) 4- (S 3-1), A 4- (B.154) 4- (S 3-1), A 4- (B.155) 4- (S 3-1), A + (B.l 56) 4- (S 3-1) , A 4- (B.157) 4- (S 3-1) , A + (B.158) + (S 3-1 ), A 4- (B.159) 4- (S 3-1), A + (§.160) 4- (S 3-1) , A 4- (B.161) 4- (S 3-1) ,Α + (B.162) + (S 3-1 ), A + (B.163) 4- (S 3-1), A 4- (B.164) 4- (S 3-1) , A 4- (B.l 65) 4- (S 3-1) , A 4- (B.l 66) 4- (S 3-1 ), A 4- (B.167) 4- (S 3-1), A + (B.168) + .(S 3-1) , A 4- (B.169) 4- (S 3-1) , A 4- (B.llO) + (S 3-1 ), A 4- (B.171) + (S 3-1), A + (B.172) 4- (S 3-1) , A 4- (B.173) 4- (S 3-1) , A 4- (B.174) 4- (S 3-1 ), A 4- (B.175) 4-' (S 3-1), A + (B.176) 4- (S 3-1) , A + (B.lll) + (S 3-1) , A + (B.178) 4- (S 3-1 ), A 4- (B.179) 4- (S 3-1), A + (B.180) 4- (S 3-1) , A 4- (B.181) 4- (S 3-1) , A 4- (B.l 82) 4- (S 3-1 ), A 4- (B.183) + (S 3-1), A + (B.184) 4- (S 3-1} , A 4- (B.l 85) 4- (S 3-1} , A 4- (B.l 86) + (S 3-1 ), A 4- (B.187) 4- (S 3-1), A + (B.l 88) 4- (S 3-1) , A 4- (B.189) 4- (S 3-1) , A 4- (B.190) 4- (S 3-1 ), A 4- (B.191) 4- (S 3-1), A + ' (B.192) 4- (S 3-1) , A 4- (B.193) 4- (S 3-1) , A 4- (B.194) 4- (S 3-1 ), A 4- (B.195) 4- (S 3-1), A + (B.196) 4- (S 3-1) , A 4- (B.197) 4- (S 3-1) , A 4- (B.198) 4- (S 3-1 ), A + (B.199) + (S- 3-l), A 4- (B.200) 4- (S 3-1): , A 4- (B.201) + (S 3-1) , A 4- (B.202) 4- (S 3-1 ), A 4- (B.203) 4- (S 3-1), A + ■ (B.204) 4- ('s 3-1): , A 4- (B.205) 4- (S 3-1): , A 4- (B.206) 4- (S 3-1 '), A 4- (B.207) 4- (S 3-1), A 4- (B.208) 4- (S 3-1) , A 4- (B.209) 4- (S' 3-1) , A 4- (B.210) 4- (S 3-1 ), A 4- (B.211) + (S 3:1), A 4- (B.212) 4- (S 3-1) , A + (B.2'13) 4- (S 3-1) , A 4- (B.214) 4- (S 3-1 ), A 4- (B.215) 4- (S 3-1), A + (B.216) 4- (S 3-1): , A 4- .(B.217) 4- (S 3-1) , A 4- (B.218) 4- (S 3.1 ), A + (B.219) 4- (S 3-1), A + (B.220). 4- (S 3-1): , A 4- (B.221) 4- (S 3-1) , A 4- (B.222) 4- (S 3-1 ), A 4- (B.223) 4- (S 3-1), A 4- (B.224) 4- (S 3-1) , A 4- (B.225) 4- (S 3-1) , A 4- (B.226) 4- (S 3-1 ), A + (B.227) + (S 3-1), A + (B.228) + (S 3-1) , A 4- (B.229) 4- (S 3-1): , A 4- (B.230) 4- (S 3-1 ), A 4- (B.231) 4- (S 3-1), A 4- (B.232) + (S 3-1) , A 4- (B.233) 4- (S 3-1). , A 4- (B:234) 4- (S 3-1 ), A + (B.235) 4- (S 3-1), A + (B.236) 4- (S 3-1) , Ä 4- (B.237) 4- (S 3-1) , A + (B.238) + (S -3-l ), A 4- (B.239) 4- ('S 3-1), A 4- ■ (B.240) 4- (S 3-1) , A 4- (B.241) 4- (S 3-1) , A 4- (B.242) 4- (S 3-1 ), A 4- .(B.243) 4- (S 3-1), A 4- (B.244) 4- (S 3-1) , A 4- (B.245) +' (S 3-1) , A 4- (B.246) 4- (S 3-1 ), A 4- (B.247) 4- (S 3-1), A + (B.248) 4- (S 3-1) , A 4- (B.249) 4- (S 3-1) , A 4- (B.250) 4- (S 3-1 ), A 4- (B.251) 4- (S 3-1), A + (B.252) 4- (S 3-1) , A 4- (B.253) 4- (S 3-1) , A 4- (B.254) 4- (S 3-1 ), A 4- (B.255) 4- (S 3-1), A 4- (B.256) 4- (S 3-1) .:, A 4- (B.257) 4- (S 3-1) ■, A 4- (B.258) 4- (S 3-1 ), A 4- (B.259) 4- (S 3-1), A + (B.260) 4- (S 3-l): , A 4- (B.261) 4- (S 3-1) , A 4- (B.262) 4- (S 3-1 ), A 4- (B.263) 4- (S 3-1), A + (B.264) 4- (S 3-1) , A 4- (B.265) 4- (S 3-1) , A 4- (B.266) + (S 3-1 ), A + (B.267) 4- (S 3-1), A 4- (B.268) 4- (S 3-1) , A 4- (B.-269) 4- (S 3-1) , A + (B.270) -+ (S 3-1 ), A 4- (B.271) 4- (S 3-1), A 4- (B.272) 4- (S 3-1) , A 4- (B.273) 4- (S 3-1) ), A 4- (B.274) +(S 3-1 ),. A + (B.275) + (S 3-1), A 4- (B.276) 4- (S 3-1): , A 4- (B.277) 4- (S 3-1), A 4- (B.278) 4- (S 3-1 ), A 4- (B.279) 4- (S 3-1), A 4- (B.280) 4- (S 3-1) In allen oben explizit aufgezählten Zweierkombinationen mit und ohne Safenerzusatz kann die Verbindung der Formel (I). auch durch ihre Salze, bevorzugt ihr Natriumsalz der Formel (Ia) ersetzt werden.
Figure imgf000025_0001
Na
Diese Mischungen weisen zudem noch zum Teil Vorteile auf, die besseren Eigenschaften der Wirkstoffformulierung, wie z.B. Aktivität oder Lagerstabilität, zum Ausdruck kommen.
Unter allen genannten Mischungen seien diejenigen hervorgehoben, bei denen der Mischpartner ausgewählt ist aus der folgenden Gruppe von Mischpartnern:
Acetochlor, Aclonifen, Alachlor, Amidosulfuran, Atrazine, Bromoxynil, Bromoxynyl-heptanoat, Brombxynil-octanoat, Bromoxynil-potassium, Chlorsulfuron, Clodinafop-propargyl, 2,4-D und seine Salze, A-mine und Ester, Difenzoquat, Dif-ufenican, Dimethenamid, Dimthenamid-P, Ethoxy- sulfuron und dessen Natriumsalz, Flufenacet, Flupyrsulfuron-methyl und dessen Natriumsalz, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Glyphosate, Glyphosate-ammonium, Gly- phosate-isopropylammonium, Glyphosate-sodium, Glyphosate-trimesium, Imazamethabenz- methyl, hnazapic, Iodosulfuron-methyl-sodium, Isoxaflutole, MCPA, Mesotrione, Metolachlor, S- Metolachlor,- Mesosulforon-methyl und dessen Natriumsalz, Nicosulfuron, Pendimethalin, Pieolinafen, Prosulfuron, Sulcotrione, Sulfosulfuron, Terbuthylazine, Tralkoxydim und Tria- sulfuron.
Am meisten hervorgehoben sei die Kombination A 4- Pinoxaden bzw. A 4- Pinoxaden 4- Cloquintocet-mexyl. Ein herbizides Mittel bestehend aus einer Wirkstoffkombination enthaltend die Verbindung A und Pinoxaden sowie gegebenenfalls den Safener Cloquintocet-mexyl ist besonders gut geeignet in dem erfindungsgemäßen Verfahren und auch zur Bekämpfung von Avena-Arten.
Sofern die Mittel nicht bereits in WO 03/026426 konkret offenbart sind, sind alle herbiziden Mittel enthaltend die obengenannten Wirkstoffkombinationen ebenfalls Gegenstand der vorliegenden Anmeldung. . ' Die Wirkstoffe der oben explizit aufgelisteten Wirkstoffkombinationen können kombiniert (z.B. als Tankmischung), aber auch sequentiell im Vorsaat-, Vorauflauf(nach Saat)-, Nachauflauf(l-2- Blatt)-, Nachauflauf (2-4-Blatt)- und Nachaufiauf(6-Blatt)-Stadium verwendet werden, dadurch ergibt sich z.B. folgendes verallgemeinertes Anwendungsschema:
Figure imgf000026_0001
Wie bereits oben erwähnt, können mit der Verbindung der Formel (I) sowie den oben aufgeführten Kombinationspräparaten mit den herbiziden Mischpartnem und/oder Safenern alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion er- haltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevor- zugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechno- logische Methoden, gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit be- stimmten Eigenschaften ("Traits"), die durch konventionelle Züchtung, durch Mutagenese, oder auch durch rekombinant'e DNA-Techniken erhalten worden sind. Dies können Sorten, Bio- und Genotypen sein.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive ("synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel - auch in Kombination mit anderen agrochemischen Wirkstoffen, besseres Wachstum der Kulturpflanzen, erhöhte Toleranz der Kulturpflanzen gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz der Kulturpflanzen gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und oder höherer Ernährungswert der Emteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Be- • schleunigung der Reife, höhere Ernteerträge, höhere Qualität iind/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle. Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrüsfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden be- sonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryΙA(c), CryHA, CrylüA, CryIHB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren -sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise hnidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinothricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle) und NewLeaf® ' (Kartoffel) vertrieben werden. Als Beispiele für Herbizid-tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z.B! Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinothricin, z.B. Raps), IMI® (Toleranz gegen hnidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid-resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfϊeld® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften ("Traits").
Die aufgeführten Pflanzen können besonders vorteilhaft mit der Verbindung der allgemeinen Formel (I) behandelt werden, wobei zusätzlich zu der guten Bekämpfung der Unkrautpflanzen die . oben genannten synergistischen Effekte mit den transgenen Pflanzen oder Pflanzensorten auftreten. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen. Die Verbindung der Formel (I) und die diese Verbindung enthaltenen Mischungen körinen in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions- Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.
Diese Formulierungen werden in. bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: aromatische Kohlenwasserstoffe wie Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische Verbindungen wie Chlorbenzole, chlorierte aliphatische Verbindungen wie Chlor- ethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie Cyclohexan oder Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.
Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und ' synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen- Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, . Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.
Es können in den Formulierungen Haftinittel wie Carboxymethylcellulose, natürliche und syn- thetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.
Die Verbindung der Formel (I) und ihre Salze können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Streuen.
Die Verbindung der Formel (I) und ihre Salze können sowohl vor als auch nach dem Auflaufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden.
Die angewandte Wirkstoffmenge kann in einem größeren Bereich schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effektes ab. Im allgemeinen liegen die Aufwandmengen zwischen 1 g (bevorzugt 8g) und 125 g Wirkstoff der Formel (I) pro Hektar Bodenfläche, vorzugsweise zwischen 2 g und 60 g pro ha, besonders bevorzugt 10 g und 30 g pro ha. Als am meisten bevorzugte erfindungsgemäße Aufwandmenge seien 10 g bis 15 g pro ha erwähnt.
Der besonders vorteilhafte Effekt der Kulturpflanzen- Verträglichkeit der in dem erfindungsge- mäßen Verfahren einsetzbaren Wirkstoffkombinationen mit Safenerzusatz ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse von der Verbindung der Formel (I) zum Safener in relativ großen Bereichen variiert werden. Bevorzugt entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) 1 bis 25 Gewichtsteile des Safener und besonders bevorzugt 3 bis 6 Gewichtsteile Safener.
Die Verwendung der Verbindung der Formel (I) und ihrer Salze geht aus den nachfolgenden Beispielen hervor. Anwendungsbeispiele:
A. Post emergence- Versuche / Freiland
Die Verbindung der Formel (I) wurde unter Freilandbedingungen in Winterweizen in Deutschland und Polen gegen das wirtschaftlich bedeutende Unkraut Apera spica-venti geprüft. Die Anlage der Kleinparzellenversuche erfolgte auf Anbauflächen der landwirtschaftlichen Praxis, wobei die Anbau- und Witterungsbedingungen über den Untersuchungszeitrauin als repräsentativ angesehen werden können. Es wurden bevorzugt Flächen mit besonders hohem Unkrautbesatz ausgewählt.
Die Applikation des Wirkstoffs erfolgte im Nachauflauf (Frühjahr) flächig im Spritzverfahren mit mittlerer Tropfengröße. Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung wurde der Wirkstoff als 10 WP (10 % w/w wasserdispergierbares Pulver) formuliert, mit dem Safener Mefenpyr-diethyl als 15 WG (15 % w/w wasserdispergierbares Granulat) und mit Alkylether sulfate als Additiv gemischt, und mit praxisüblichen Wasseraufwandmengen ausgebracht.
Zur Beurteilung der Kulturverträglichkeit wurden 1 bis 7 Wochen nach der Behandlung Pflanzen-
• wuchshemmungen oder Aufhellungen der Blattfläche in % Schädigung im Vergleich zur Ent- Wicklung der unbehandelten Kontrolle bonitiert. Die herbizide Wirksamkeit wurde zu mehreren Terminen nach der Behandlung auf Basis der Unkrautentwicklung als % Reduktion im Vergleich zur unbehandelten Kontrolle erfasst. Es bedeuten: .
0 % = keine Schädigung der Kultur bzw. keine herbizide Wirkung, 100 % = totale Vernichtung der Kultur bzw. der Unkräuter. Die durchgeführten Versuche zeigen, dass die Verbindung der Formel (I) besonders gut zur Bekämpfung der annuellen Arten von Apera spica-venti, in Getreide geeignet ist.
["% w/w" = Gewichtsprozent]
Tabelle A
Post emergence- ersuche / Freiland
Figure imgf000032_0001

Claims

Patentansprüche
1. Verwendung der Verbindung 5-Methoxy-4-methyl-2-[(4-methoxycarbonyl-_--methyl-thien- 3 -yl)-sulfonyl-amino-carbonyl] -2,4-dihydro-3H- 1 ,-2,4-triazol-3 -on* der Formel (I)
Figure imgf000033_0001
'5 und/oder der Salze der Verbindung der Formel (I) zur selektiven Bekämpfung von Unkräutern der Gattung Apera in Nutzpflanzenkulturen.
2. Verfahren zur selektiven Bekämpfung von Unkräutern der Gattung Apera in Nutzpflanzenkulturen, welches dadurch gekennzeichnet ist, dass man die Verbindung der Formel (I) gemäß Anspruch 1 und/oder Salze der Verbindung der Formel (I) zusammen mit ober- L 0 flächenaktiven Mitteln und/oder üblichen Stteckmitteln in Nutzpflanzenkulturen appliziert.
PCT/EP2005/001735 2004-03-05 2005-02-19 Unkrautbekämpfungsverfahren WO2005087006A1 (de)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007057107A1 (de) * 2005-11-17 2007-05-24 Bayer Cropscience Ag Wässriges herbizides mittel auf basis eines suspensionskonzentrats enthaltend herbizide und safener

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004010813A1 (de) * 2004-03-05 2005-11-10 Bayer Cropscience Ag Neue Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)onen und 4-HPPD-Hemmstoffen
CN101961023B (zh) * 2010-10-12 2013-04-24 北京颖泰嘉和生物科技有限公司 一种除草剂组合物及其应用
US9367568B2 (en) * 2013-05-15 2016-06-14 Facebook, Inc. Aggregating tags in images

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003026427A1 (de) * 2001-09-21 2003-04-03 Bayer Cropscience Ag Selektive herbizide auf basis von substituierten thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und safenern
WO2003026426A1 (de) * 2001-09-21 2003-04-03 Bayer Cropscience Ag Herbizide enthaltend substituierte thien-3-yl-sulfonylamino (thio) carbonyltriazolin (thi) one

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU518216B2 (en) * 1977-09-06 1981-09-17 Hafslund Nycomed Pharma Aktiengesellschaft Thienothiazine derivatives
US4701535A (en) * 1979-11-30 1987-10-20 E. I. Du Pont De Nemours And Company Agricultural ureas and isoureas
US4659361A (en) * 1984-06-11 1987-04-21 E. I. Du Pont De Nemours And Company Herbicidal iodopyrimidines
JPS62242678A (ja) * 1986-04-10 1987-10-23 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− 除草剤性チオフエンスルホンアミド類
US5149356A (en) * 1988-05-09 1992-09-22 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5599944A (en) * 1987-03-24 1997-02-04 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5276162A (en) * 1988-05-09 1994-01-04 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
US5241074A (en) * 1988-05-09 1993-08-31 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5057144A (en) * 1988-05-09 1991-10-15 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5300480A (en) * 1989-04-13 1994-04-05 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen
US5541337A (en) * 1989-04-13 1996-07-30 Bayer Aktiengesellschaft Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones
US5238910A (en) * 1989-11-03 1993-08-24 Bayer Aktiengesellschaft Herbicidal halogenated sulphonylaminocarbonyltriazolinones
DE4029753A1 (de) * 1990-09-20 1992-03-26 Basf Ag Sulfonamide
US5534486A (en) * 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
DE19540737A1 (de) * 1995-11-02 1997-05-07 Bayer Ag Substituierte Sulfonylamino(thio)carbonylverbindungen
DE19632945A1 (de) * 1996-08-16 1998-02-19 Bayer Ag Substituierte Sulfonylamino(thio)carbonylverbindungen
DE19650196A1 (de) * 1996-12-04 1998-06-10 Bayer Ag Thienylsulfonylamino(thio)carbonylverbindungen
DE19933260A1 (de) * 1999-07-15 2001-01-18 Bayer Ag Substituierte Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)one
KR100351054B1 (ko) * 2000-06-13 2002-09-05 삼성전자 주식회사 승압 전압 레벨 안정화 회로를 구비한 반도체 메모리장치
BR0115121A (pt) * 2000-11-03 2003-09-30 Dow Agrosciences Llc Compostos n-((1,2,4)triazoloazinil)tiofenossulfonamida como herbicidas
DE10119721A1 (de) * 2001-04-21 2002-10-31 Bayer Cropscience Gmbh Herbizide Mittel enthaltend Benzoylcyclohexandione und Safener

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003026427A1 (de) * 2001-09-21 2003-04-03 Bayer Cropscience Ag Selektive herbizide auf basis von substituierten thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und safenern
WO2003026426A1 (de) * 2001-09-21 2003-04-03 Bayer Cropscience Ag Herbizide enthaltend substituierte thien-3-yl-sulfonylamino (thio) carbonyltriazolin (thi) one

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007057107A1 (de) * 2005-11-17 2007-05-24 Bayer Cropscience Ag Wässriges herbizides mittel auf basis eines suspensionskonzentrats enthaltend herbizide und safener
US8053393B2 (en) 2005-11-17 2011-11-08 Bayer Cropscience Ag Aqueous herbicidal composition based on a suspension concentrate comprising herbicides and safeners
EA015904B1 (ru) * 2005-11-17 2011-12-30 Байер Кропсайенс Аг Водное гербицидное средство на основе суспензионного концентрата, содержащее гербициды и защитное средство
EA015904B9 (ru) * 2005-11-17 2012-07-30 Байер Кропсайенс Аг Водное гербицидное средство на основе суспензионного концентрата, содержащее гербициды и защитное средство
CN101309588B (zh) * 2005-11-17 2013-07-10 拜尔作物科学股份公司 基于包含除草剂和安全剂的悬浮液浓缩物的含水除草组合物

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